An official website of the United States government

Adiponitrile

PubChem CID
8128
Structure
Adiponitrile_small.png
Adiponitrile_3D_Structure.png
Adiponitrile__Crystal_Structure.png
Molecular Formula
Synonyms
  • ADIPONITRILE
  • Hexanedinitrile
  • 1,4-Dicyanobutane
  • 111-69-3
  • Adipyldinitrile
Molecular Weight
108.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Adiponitrile appears as a colorless to light yellow liquid which is fairly soluble and is less dense than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption.
Adiponitrile is a chemical compound of cyanide. It is is an important precursor to the polymer nylon 66. (L584)
L584: Wikipedia. Adiponitrile. Last Updated 15 February 2009. http://en.wikipedia.org/wiki/Adiponitrile

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Adiponitrile.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
View All
COD Number
Associated Article
Seidel, Rüdiger W.; Goddard, Richard; Nöthling, Nils; Lehmann, Christian W.. Adiponitrile at 100K. Acta Crystallographica Section C 2017;73(11):937-940. DOI: 10.1107/S2053229617014620
Crystal Structure Depiction
Crystal Structure Depiction
Hermann-Mauguin space group symbol
P 1 21/c 1
Hall space group symbol
-P 2ybc
Space group number
14
a
4.5031 Å
b
6.5860 Å
c
10.572 Å
α
90 °
β
96.540 °
γ
90 °
Z
2
Z'
0.5
Residual factor
0.0456

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

hexanedinitrile
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

BTGRAWJCKBQKAO-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C(CCC#N)CC#N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H8N2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C6H8N2

CN(CH2)4CN

2.3 Other Identifiers

2.3.1 CAS

111-69-3
68411-90-5

2.3.2 Deprecated CAS

55462-97-0
68511-79-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 UN Number

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 ICSC Number

2.3.10 Nikkaji Number

2.3.11 NSC Number

2.3.12 RTECS Number

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • adiponitrile
  • hexanedinitrile

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
108.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
108.068748264 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
108.068748264 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
47.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
113
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Adiponitrile appears as a colorless to light yellow liquid which is fairly soluble and is less dense than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption.
Liquid
Water-white, practically odorless, oily liquid;[Note: A solid below 34 degrees F; Forms cyanide in the body; [NIOSH]
ODOURLESS OILY COLOURLESS LIQUID.
Water-white, practically odorless, oily liquid.
Water-white, practically odorless, oily liquid. [Note: A solid below 34 °F. Forms cyanide in the body.]

3.2.2 Color / Form

NEEDLES FROM ETHER
Lide, D.R. (ed). CRC Handbook of Chemistry and Physics. 72nd ed. Boca Raton, FL: CRC Press, 1991-1992., p. 3-29
Colorless liq
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152
Water-white, oily liquid
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8

3.2.3 Odor

Practically odorless.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8

3.2.4 Boiling Point

563 °F at 760 mmHg (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
295 °C @ 760 mm Hg
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 23
295 °C
563 °F

3.2.5 Melting Point

36.1 °F (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
1-3 °C
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 23
1 °C
34 °F

3.2.6 Flash Point

199.4 °F (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
93 °C
200 °F (93 °C) (OPEN CUP)
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-11
159 °C c.c.
199 °F (open cup)
(oc) 199 °F

3.2.7 Solubility

50 to 100 mg/mL at 73 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Sol in alc, chloroform
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 23
Sol in methanol, ethanol, chloroalkanes, and aromatics but has low solubility in carbon disulfide, ethyl ether, and aliphatic hydrocarbons.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 444
In water, 8.0X10+4 mg/l @ 20 °C.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 444
Solubility in water, g/l at 20 °C: 50-100 (good)
4.5%

3.2.8 Density

0.965 at 68 °F (EPA, 1998) - Less dense than water; will float
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
0.9676 g/ml @ 20 °C
Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-187
Relative density (water = 1): 0.97
0.97

3.2.9 Vapor Density

3.73 (EPA, 1998) - Heavier than air; will sink (Relative to Air)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
3.73 (air= 1)
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152
Relative vapor density (air = 1): 3.7
3.73

3.2.10 Vapor Pressure

2 mmHg at 246 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
0.000679 [mmHg]
6.8X10-4 mm Hg at 25 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.
Vapor pressure, Pa at 20 °C: 0.3
0.002 mmHg

3.2.11 LogP

log Kow= -0.32
Tanii H, Hashimoto K; Arch Toxicol 57: 88-93 (1985)
-0.32

3.2.12 Autoignition Temperature

1022 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
1022 °F (550 °C)
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-13
550 °C

3.2.13 Decomposition

WHEN HEATED TO DECOMP RELEASES VAPORS CONTAINING HYDROCYANIC ACID.
Winek, C.L. Drug and Chemical Blood-Level Data 1985. Pittsburgh, PA: Allied Fischer Scientific, 1985., p. 938
When heated to decomp it emits highly toxic fumes of CN- /cyanides/.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 73

3.2.14 Viscosity

9.1 cP @ 20 °C; 2.6 cP @ 70 °C
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 445
58 mPa*s at 30 °C

3.2.15 Heat of Combustion

-40.4X10+6 J/kg
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 445

3.2.16 Heat of Vaporization

70.4X10+4 J/kg
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 445

3.2.17 Refractive Index

Index of refraction: 1.4380 @ 20 °C/D
Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-187

3.2.18 Kovats Retention Index

Standard non-polar
1090

3.2.19 Other Experimental Properties

Vap: 2 mm Hg @ 119 °C
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Nitrogen Compounds -> Nitriles

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
1H NMR: SAD 6702 (Sadtler Research Laboratories spectral collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
JEOL
Frequency
90 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
2.33:109.00, 2.48:238.00, 2.46:296.00, 2.39:322.00, 2.37:414.00, 2.42:503.00, 1.83:1000.00, 1.99:70.00, 1.90:366.00, 1.80:323.00, 2.56:47.00, 2.44:966.00, 1.89:283.00, 1.83:933.00, 1.84:318.00, 2.53:153.00, 2.32:68.00, 1.75:212.00, 2.40:321.00, 1.98:56.00, 1.88:294.00, 2.50:249.00, 2.51:221.00, 1.94:88.00, 1.77:176.00, 1.79:469.00, 1.86:444.00, 2.47:263.00, 2.37:366.00
Thumbnail
Thumbnail
2 of 3
View All
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
24.32:995.00, 119.23:423.00, 16.56:1000.00
Thumbnail
Thumbnail
2 of 3
View All
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI RMU-7M
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

41 99.99

68 41.16

54 40.53

55 18.66

39 16.85

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 7
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI RMU-6M
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

41 99.99

68 82.95

54 68.04

55 38.27

27 19.52

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2.2 Other MS

1 of 3
View All
Other MS
MS: NIST 1422 (NIST/EPA/MSDC Mass Spectral database, 1990 version); WILEY 510 (Atlas of Mass Spectral Data, John Wiley and Sons, New York)
2 of 3
View All
Authors
TAJIMA S, GUNMA COLLEGE OF TECHNOLOGY
Instrument
HITACHI RMU-7M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

41 999

68 412

54 405

55 187

39 169

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 IR Spectra

IR Spectra
IR: SADG 1875 (Sadtler Research Laboratories IR grating Collection)

4.3.1 FTIR Spectra

1 of 2
Technique
NEAT
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker IFS 85
Technique
Cell
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Technique
ATR-Cylindrical Internal Reflectance (CIR)
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
D77001
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.3 Vapor Phase IR Spectra

1 of 2
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Reported Fatal Dose

205 to 300 milligrams for an adult human (cyanide salts). (T86)
T86: Baselt RC and Cravey RH (1989). Disposition of Toxic Drugs and Chemicals in Man. 3rd ed. Chicago, IL.: Year Book Medical Publishers.

8 Pharmacology and Biochemistry

8.1 Absorption, Distribution and Excretion

Seventy nine percent of dose /about 50 mg/kg sc admin to guinea pigs/ was eliminated as thiocyanate in urine. ... Skin penetration was suggested by incr in thiocyanate in urine ... after application to depilated skin. Greater quantities were absorbed when skin was abraded.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152
The concentrations of thiocyanate in the blood and urine of guinea pigs injected with adiponitrile were proportional to the doses administered. Following administration of adiponitrile, 79% was eliminated as thiocyanate in the urine of guinea pigs. Of the cyanide antidotes, thiosulfate was most effective. However, on the basis of the ratio between administered adiponitrile dose and quantity of cyanide detected, /it was/ concluded that a greater part of the dose was metabolized to cyanide.
Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 325

8.2 Metabolism / Metabolites

... In guinea pigs ... it is hydrolyzed to hydrogen cyanide in the body giving rise to thiocyanate in urine.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152
Male ddY mice were pretreated with carbon tetrachloride or olive oil and administered adiponitrile orally in concentrations sufficient to determine its median lethal dose (LD50). Brain cyanide concentrations were determined. The distribution coefficient (P) for partitioning adiponitrile between water and n-octanol was measured. Mice were pretreated as before and dosed with adiponitrile at 3 to 5 times its LD50. Mean survival times were determined. Hepatic microsomes were obtained from mice pretreated with carbon tetrachloride or olive oil and incubated with adiponitrile. The rate of release of free cyanide was investigated. The oral LD50 for animals pretreated with olive oil was 1.592 mmol/kg. The LD50 for the carbon tetrachloride treated mice was 2.652 mmol/kg. Brain cyanide concentrations in olive oil pretreated mice ranged from 0.35 to 0.74 ug/g. Carbon tetrachloride pretreatment lengthened survival and reduced brain cyanide concentrations. Dinitriles are metabolized to cyanides in vivo and in vitro.
Tanii H, Hashimoto K; Archives of Toxicol 57 (2): 88-93 (1985)
Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
L96: ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp8.html

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used to manufacture hexamethylenediamine that is used to make nylon 66; [HSDB]
Intermediate in the manufacture of nylon; organic synthesis
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 23
Preparation of adipoquanamine; extractant for aromatic hydrocarbons
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 447

9.1.1 Use Classification

Hazard Classes and Categories -> Flammable - 2nd degree, Reactive - 1st degree

9.1.2 Industry Uses

  • Other (specify)
  • Intermediates
  • Intermediate

9.2 Methods of Manufacturing

Chlorination of butadiene to dichlorobutylene, which is reacted with 35% sodium cyanide soln to yield 1,4-dicyanobutylene; which is hydrogenated to adiponitrile. Also by electroorganic synthesis from acrylonitrile.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 23
Reaction of adipic acid with ammonia (either liquid or vapor phase) produces adipamide as intermediate, which is subsequently dehydrated to adiponitrile.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 444
Prepared by dimerization of acrylonitrile at the cathode of an electrolytic cell (propionitrile and bis(cyanoethyl) ether are by-products).
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 446
Prepared by direct addition of hydrogen cyanide to butadiene catalyzed by soluble, air and moisture sensitive, triarylphosphite nickel(0) complexes.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 446

9.3 Impurities

Impurities that may be present /such as propionitrile and bis(cyanoethyl) ether in the butadiene process and acrylonitrile in the electrolytic process/ depend on the method of manufacture and, thus, vary depending on the source.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 446

9.4 Formulations / Preparations

Typical concentration is 99.5 wt% adiponitrile
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 446

9.5 U.S. Production

Aggregated Product Volume

2019: 1,000,000,000 - <5,000,000,000 lb

2018: 1,000,000,000 - <5,000,000,000 lb

2017: 1,000,000,000 - <5,000,000,000 lb

2016: 1,000,000,000 - <5,000,000,000 lb

(1972) 3.6X10+11 GRAMS
SRI
(1991) 1415 million lb (capacity)
SRI. 1992 Directory of Chemical Producers-United States of America. Menlo Park, CA: SRI International, 1992., p. 444
U.S. production capacity = 625,000 metric tons in 1992
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 447

9.6 General Manufacturing Information

Industry Processing Sectors
  • All Other Basic Organic Chemical Manufacturing
  • All Other Chemical Product and Preparation Manufacturing
  • Services
EPA TSCA Commercial Activity Status
Hexanedinitrile: ACTIVE

10 Identification

10.1 Analytic Laboratory Methods

A GC method ... using a flame ionization detector and SP1000 column.
Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 325

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 3
View All
Pictogram(s)
Acute Toxic
Irritant
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H315 (19.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (20.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H330 (20.4%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H332 (77.7%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (19.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 206 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Skin Irrit. 2 (19.9%)

Eye Irrit. 2 (20.4%)

Acute Tox. 2 (20.4%)

Acute Tox. 4 (77.7%)

STOT SE 3 (19.9%)

Acute toxicity (Oral) - Category 3

Acute toxicity (Dermal) - Category 3

Acute toxicity (Inhalation: Dusts and mists) - Category 4

Serious eye damage/eye irritation - Category 2B

Specific target organ toxicity - Single exposure - Category 1 (nervous system)

Specific target organ toxicity - Repeated exposure - Category 2 (blood)

11.1.3 NFPA Hazard Classification

1 of 2
View All
NFPA 704 Diamond
2-2-1
NFPA Health Rating
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
NFPA Fire Rating
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
NFPA Instability Rating
1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

11.1.4 Health Hazards

This material is toxic by ingestion and inhalation. It produces disturbances of the respiration and circulation, irritation of the stomach and intestine, and loss of weight. It is irritating to skin and eyes. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
ERG 2024, Guide 153 (Adiponitrile)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).

· Contact with molten substance may cause severe burns to skin and eyes.

· Avoid any skin contact.

· Fire may produce irritating, corrosive and/or toxic gases.

· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

11.1.5 Fire Hazards

Combustion products may contain hydrogen cyanide (hydrocyanic acid, HCN). Vapor may explode if ignited in an enclosed area. When heated to decomposition, it emits highly toxic fumes. Avoid oxidizing material. Hazardous polymerization may not occur. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
ERG 2024, Guide 153 (Adiponitrile)

· Combustible material: may burn but does not ignite readily.

· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.

· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.

· Corrosives in contact with metals may evolve flammable hydrogen gas.

· Containers may explode when heated.

· Runoff may pollute waterways.

· Substance may be transported in a molten form.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

11.1.6 Hazards Summary

Toxic by ingestion; Skin burns in workers reported; [ACGIH] See NITRILES.
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.

11.1.7 Fire Potential

FLAMMABLE WHEN EXPOSED TO HEAT OR FLAME.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 73

11.1.8 Skin, Eye, and Respiratory Irritations

Immediately irritating to the eye. /Cyanides/
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS(NIOSH) Publication No. 90-117. Washington, DC: U.S. Government Printing Office, June 1990, p. 76
... HUMAN SKIN EXPOSURES TO ADIPONITRILE RESULT IN SKIN IRRITATION ...
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3153

11.2 Safety and Hazard Properties

11.2.1 Flammable Limits

LOWER 1.0% @ 200 °C
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
Flammability
Class IIIA Combustible Liquid: Fl.P. at or above 140 °F and below 200 °F.

11.2.2 Lower Explosive Limit (LEL)

1 % at 392F (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
1.7%

11.2.3 Upper Explosive Limit (UEL)

5 % (NIOSH, 2024)
5.0%

11.2.4 Critical Temperature & Pressure

Critical temperature: 507 °C; Critical pressure: 2.8 MPa (27.6 atm)
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. SUPP (1998) 445

11.2.5 Explosive Limits and Potential

Explosive limits , vol% in air: 1.7-4.9

11.2.6 NIOSH Recommendations

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 4 ppm (18 mg/cu m).
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8

11.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. Administration of oxygen may be needed. No mouth-to-mouth artificial respiration. Refer immediately for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap. Administration of oxygen may be needed. Refer immediately for medical attention.
Eye First Aid
Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.
Ingestion First Aid
Rinse mouth. Administration of oxygen may be needed. Give one or two glasses of water to drink. Refer for medical attention .

11.3.1 First Aid

Warning: Effects may be delayed. Caution is advised. Vital signs should be monitored closely.

Signs and Symptoms of Acute Adiponitrile Exposure: Signs and symptoms of acute exposure to adiponitrile may include tightness of the chest and tachypnea (rapid respiratory rate). Tachycardia (rapid heart rate), hypotension (low blood pressure), and cyanosis (blue tint to skin and mucous membranes) may also occur. Victims may experience headache, weakness, dizziness, difficulty in standing, dilated pupils, confusion, and seizures. Vomiting has been reported. Adiponitrile may irritate or burn the skin, eyes, and mucous membranes.

Emergency Life-Support Procedures: Acute exposure to adiponitrile may require decontamination and life support for the victims. All exposed persons should be transported to a health care facility as quickly as possible. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.

Inhalation Exposure:

1. Move victims to fresh air. Emergency personnel should avoid self-exposure to adiponitrile.

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. IMMEDIATELY begin administering 100% oxygen to all victims. Monitor victims for respiratory distress.Warning: To prevent self-poisoning, avoid mouth-to-mouth breathing; use a forced-oxygen mask. Direct oral contact with adiponitrile-contaminated persons or their gastric contents can result in self-poisoning.

3. RUSH to a health care facility!

4. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

Dermal/Eye Exposure:

1. Remove victims from exposure. Emergency personnel should avoid self- exposure to adiponitrile.

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. IMMEDIATELY begin administering 100% oxygen to all victims. Monitor victims for respiratory distress.Warning: To prevent self-poisoning, avoid mouth-to-mouth breathing; use a forced-oxygen mask. Direct oral contact with adiponitrile-contaminated persons or their gastric contents can result in self-poisoning.

3. RUSH to a health care facility!

4. Remove contaminated clothing as soon as possible.

5. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.

6. Wash exposed skin areas twice with soap and water.

7. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

Ingestion Exposure:

1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. IMMEDIATELY begin administering 100% oxygen to all victims. Monitor victims for respiratory distress.Warning: To prevent self-poisoning, avoid mouth-to-mouth breathing; use a forced-oxygen mask. Direct oral contact with adiponitrile-contaminated persons or their gastric contents can result in self-poisoning.

2. RUSH to a health care facility!

3. DO NOT induce vomiting. Ipecac is not recommended for ingestion of adiponitrile.

4. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

5. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water.

6. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
ERG 2024, Guide 153 (Adiponitrile)

General First Aid:

· Call 911 or emergency medical service.

· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.

· Move victim to fresh air if it can be done safely.

· Administer oxygen if breathing is difficult.

· If victim is not breathing:

-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingestedor inhaled the substance.

-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).

-- If no pulse detected or no respiratory medical device available, provide continuouscompressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.

· Remove and isolate contaminated clothing and shoes.

· For minor skin contact, avoid spreading material on unaffected skin.

· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.

· For severe burns, immediate medical attention is required.

· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.

· Keep victim calm and warm.

· Keep victim under observation.

· For further assistance, contact your local Poison Control Center.

· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.

Specific First Aid:

· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

· Removal of solidified molten material from skin requires medical assistance.

In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section.

(See general first aid procedures)

Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.

Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.

Breathing: Respiratory support

Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

11.4 Fire Fighting

Wear chemical protective suit with self-contained breathing apparatus. Cool exposed containers with water.

Use dry chemical, carbon dioxide, water spray, fog or foam. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

11.4.1 Fire Fighting Procedures

USE WATER SPRAY, DRY CHEMICAL, FOAM OR CARBON DIOXIDE. USE WATER SPRAY TO KEEP FIRE-EXPOSED CONTAINERS COOL. APPROACH FIRE FROM UPWIND TO AVOID HAZARDOUS VAPORS AND TOXIC DECOMPOSITION PRODUCTS.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-13
If material on fire or involved in fire: Use water in flooding quantities as fog. use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. Cool all affected containers with flooding quantities of water. Apply water form as far a distance as possible.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 18

11.5 Accidental Release Measures

Public Safety: ERG 2024, Guide 153 (Adiponitrile)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep unauthorized personnel away.

· Stay upwind, uphill and/or upstream.

· Ventilate closed spaces before entering, but only if properly trained and equipped.

Spill or Leak: ERG 2024, Guide 153 (Adiponitrile)

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

· Stop leak if you can do it without risk.

· Prevent entry into waterways, sewers, basements or confined areas.

· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.

· DO NOT GET WATER INSIDE CONTAINERS.

11.5.1 Isolation and Evacuation

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Evacuation: ERG 2024, Guide 153 (Adiponitrile)

Immediate precautionary measure

· Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

Spill

· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.

· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.

Fire

· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

11.5.2 Spillage Disposal

Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

11.5.3 Cleanup Methods

Stop or control the leak, if this can be done without undue risk. Use water spray to cool and disperse vapors, and protect personnel. Approach release from upwind. Absorb in noncombustible material for proper disposal.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-13

11.5.4 Disposal Methods

A poor candidate for incineration. /Cyanides/
USEPA; Engineering Handbook for Hazardous Waste Incineration p.3-8 (1981) EPA 68-03-3025

11.5.5 Preventive Measures

The worker should immediately wash the skin when it becomes contaminated.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
Work clothing that becomes wet or significantly contaminated should be removed oand replaced.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
For more Preventive Measures (Complete) data for ADIPONITRILE (9 total), please visit the HSDB record page.

11.6 Handling and Storage

11.6.1 Nonfire Spill Response

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

11.6.2 Safe Storage

Separated from strong oxidants, strong acids and food and feedstuffs. Ventilation along the floor.

11.6.3 Storage Conditions

Separate from strong acids and oxidizing materials. Store in a cool, dry, well-ventilated location. Outside or detached storage is preferred.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-13

11.7 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 153 (Adiponitrile)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.

· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

11.7.2 Permissible Exposure Limit (PEL)

none

11.7.3 Immediately Dangerous to Life or Health (IDLH)

N.D.

See: IDLH INDEX

11.7.4 Threshold Limit Values (TLV)

2.0 [ppm]
8 hr Time Weighted Avg (TWA): 2 ppm, skin.
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH, 2008, p. 11
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH, 2008, p. 5
2 ppm as TWA; (skin)
TLV-TWA (Time Weighted Average)
2 ppm [1990]

11.7.5 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 153 (Adiponitrile)

Small Fire

· Dry chemical, CO2 or water spray.

Large Fire

· Dry chemical, CO2, alcohol-resistant foam or water spray.

· If it can be done safely, move undamaged containers away from the area around the fire.

· Dike runoff from fire control for later disposal.

Fire Involving Tanks, Rail Tank Cars or Highway Tanks

· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.

· Do not get water inside containers.

· Cool containers with flooding quantities of water until well after fire is out.

· Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

· ALWAYS stay away from tanks in direct contact with flames.

11.7.6 Inhalation Risk

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

11.7.7 Effects of Short Term Exposure

The substance is irritating to the eyes and skin. Exposure could cause convulsions, unconsciousness and death. Medical observation is indicated.

11.7.8 Effects of Long Term Exposure

The substance may have effects on the blood and adrenals. This may result in anaemia and tissue lesions.

11.7.9 Personal Protective Equipment (PPE)

Excerpt from NIOSH Pocket Guide for Adiponitrile:

Skin: PREVENT SKIN CONTACT - Wear appropriate personal protective clothing to prevent skin contact.

Eyes: PREVENT EYE CONTACT - Wear appropriate eye protection to prevent eye contact.

Wash skin: WHEN CONTAMINATED - The worker should immediately wash the skin when it becomes contaminated.

Remove: WHEN WET OR CONTAMINATED - Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Change: DAILY - Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. (NIOSH, 2024)

RUBBER GLOVES & CLOTHING GIVING FULL BODY & FACE PROTECTION TO AVOID CONTACT WITH SKIN. AIR OR OXYGEN MASK.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
Wear appropriate personal protective clothing to prevent skin contact.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
Wear appropriate eye protection to prevent eye contact.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
Recommendations for respirator selection. Max concn for use: 40 ppm. Respirator Class(es): Any supplied-air respirator.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
For more Personal Protective Equipment (PPE) (Complete) data for ADIPONITRILE (9 total), please visit the HSDB record page.

(See personal protection and sanitation codes)

Skin: Prevent skin contact - Wear appropriate personal protective clothing to prevent skin contact.

Eyes: Prevent eye contact - Wear appropriate eye protection to prevent eye contact.

Wash skin: When contaminated

Remove: When wet or contaminated

Change: Daily - Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

11.7.10 Respirator Recommendations

NIOSH

Up to 40 ppm:

(APF = 10) Any supplied-air respirator

Up to 100 ppm:

(APF = 25) Any supplied-air respirator operated in a continuous-flow mode

Up to 200 ppm:

(APF = 50) Any self-contained breathing apparatus with a full facepiece

(APF = 50) Any supplied-air respirator with a full facepiece

Up to 250 ppm:

(APF = 2000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode

Emergency or planned entry into unknown concentrations or IDLH conditions:

(APF = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode

(APF = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus

Escape:

(APF = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister

Any appropriate escape-type, self-contained breathing apparatus

Important additional information about respirator selection

11.7.11 Preventions

Fire Prevention
NO open flames.
Exposure Prevention
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear face shield.
Ingestion Prevention
Do not eat, drink, or smoke during work. Wash hands before eating.

11.8 Stability and Reactivity

11.8.1 Air and Water Reactions

No rapid reaction with air. No rapid reaction with water.

11.8.2 Reactive Group

Nitriles

11.8.3 Reactivity Profile

ADIPONITRILE is incompatible with strong oxidizers. It is also incompatible with strong acids, strong bases and strong reducing agents. (NTP, 1992).
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.8.4 Hazardous Reactivities and Incompatibilities

Oxidizers (e,g., perchlorates, nitrates), strong acids (e.g., sulfuric acid) [Note: Decomposes above 194 degrees F, forming hydrogen cyanide].
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 8
... 18 Month old bottles of iminodipropionitrile exploded, probably owing to slow hydrolysis and release of ammonia.
Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 636

11.9 Transport Information

11.9.1 DOT Emergency Guidelines

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
For more DOT Emergency Guidelines (Complete) data for ADIPONITRILE (8 total), please visit the HSDB record page.

11.9.2 DOT ID and Guide

11.9.3 Shipping Name / Number DOT/UN/NA/IMO

UN 2205; Adiponitrile
IMO 6.1; Adiponitrile

11.9.4 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 15, 2006: https://www.ecfr.gov
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
International Air Transport Association. Dangerous Goods Regulations. 47th Edition. Montreal, Quebec Canada. 2006., p. 133
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
International Maritime Organization. International Maritime Dangerous Goods Code. London, UK. 2004., p. 102

11.9.5 DOT Label

Poison

11.9.6 Packaging and Labelling

Do not transport with food and feedstuffs.

11.9.7 UN Classification

UN Hazard Class: 6.1; UN Pack Group: III

11.10 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Hexanedinitrile
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Adiponitrile: Does not have an individual approval but may be used under an appropriate group standard

11.10.1 Atmospheric Standards

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Adiponitrile is produced, as an intermediate or a final product, by process units covered under this subpart.
40 CFR 60.489 (7/1/2000)

11.10.2 CERCLA Reportable Quantities

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Adiponitrile is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1000 lbs.
40 CFR 355 (7/1/2000)

11.10.3 TSCA Requirements

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hexanedinitrile is included on this list.
40 CFR 716.120 (7/1/2000)

11.11 Other Safety Information

11.11.1 Toxic Combustion Products

Products of combustion may be more hazardous than the material itself. By-products include hydrogen cyanide and irritants.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-13

11.11.2 Special Reports

Kaplita PV and Smith RP; Toxicol Appl Pharmacol 84 (3): 533-540 (1986). Pathways for the bioactivation of aliphatic nitriles to free cyanide in mice.
Homan ER; Clinical and Experimental Toxicol of Cyanides, Bristol, UK 1-21 pages (1987). Reactions, industrial processes, and materials with potential for exposure to cyanide compounds were discussed in this overview on the toxicology of cyanides.

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
L97: Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. http://en.wikipedia.org/wiki/Cyanide_poisoning

12.1.2 EPA IRIS Information

Substance
Toxicity Summary
EPA IRIS Summary PDF (Update: Feb-01-1991 )

12.1.3 EPA Provisional Peer-Reviewed Toxicity Values

Chemical Substance
Reference Concentration (RfC), Chronic
6 x 10^-3 mg/m^3
Reference Concentration (RfC), Subchronic
6 x 10^-2 mg/m^3
PPRTV Assessment
Weight-Of-Evidence (WOE)
Inadequate information to assess carcinogenic potential
Last Revision
2005

12.1.4 RAIS Toxicity Values

Inhalation Chronic Reference Concentration (RfC) (mg/m^3)
0.006
Inhalation Chronic Reference Concentration Reference
PPRTV Current
Inhalation Subchronic Reference Concentration (RfCs) (mg/m^3)
0.06
Inhalation Subchronic Reference Concentration Reference
PPRTV Current

12.1.5 NIOSH Toxicity Data

12.1.6 Evidence for Carcinogenicity

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: No human and no animal cancer data were available. Adiponitrile was negative for mutagenicity in Salmonella with and without activation. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: None.
U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS). Summary on Adiponitrile (111-69-3). Available from, as of March 15, 2000: https://www.epa.gov/iris/

12.1.7 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

12.1.8 Health Effects

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
L96: ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp8.html
L97: Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. http://en.wikipedia.org/wiki/Cyanide_poisoning

12.1.9 Exposure Routes

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Oral (L96) ; inhalation (L96) ; dermal (L96)
L96: ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp8.html

12.1.10 Symptoms

Inhalation Exposure
Headache. Vomiting. Dizziness. Nausea. Laboured breathing. Confusion. Convulsions.
Skin Exposure
MAY BE ABSORBED! Redness. Pain.
Eye Exposure
Redness. Blurred vision.
Ingestion Exposure
Abdominal pain. Further see Inhalation.
irritation eyes, skin, respiratory system; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; blurred vision; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting
Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
L96: ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp8.html
L97: Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. http://en.wikipedia.org/wiki/Cyanide_poisoning

12.1.11 Target Organs

Eyes, skin, respiratory system, central nervous system, cardiovascular system

12.1.12 Adverse Effects

Other Poison - Chemical Asphyxiant

Dermatotoxin - Skin burns.

12.1.13 Acute Effects

12.1.14 Toxicity Data

LC50 (rat) = 1,710 mg/m3/4h
LD50: 155 mg/kg (Oral, Rat) (T14) LD50: 40 mg/kg (Intraperitoneal, Mouse) (T14) LD50: 50 mg/kg (Subcutaneous, Guinea pig) (T32) LC50: 1.71 mg/L over 4 hours (Inhalation, Rat) (T88)
T14: Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
T32: Verschueren K (1983). Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co.
T88: Snyder, R (1990). Ethyl Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier.

12.1.15 Treatment

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
L97: Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. http://en.wikipedia.org/wiki/Cyanide_poisoning

12.1.16 Interactions

The toxic mechanism of nitriles (including adiponitrile) and the effect of metabolic modifiers in mice were studied in relation to their physicochemical properties. All the test nitriles liberated cyanide both in vivo and in vitro, with the exception of benzonitrile, although the extent of liberation and the effect of carbon tetrachloride pretreatment on the mortality of animals differed among nitriles. From these results, test compounds were tentatively divided into 3 groups. In group 1, acute toxicity was greatly reduced by carbon tetrachloride pretreatment, in group 2, toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced. The amount of cyanide was higher at death in the brains of mice given group 1 compounds, the level being comparable to that found in mice killed by dosing with potassium cyanide. The relation between log (1/LD50) and log p for the compounds in group 1 fitted a parabolic plot, while that for compounds in group 2 was linear. For most nitriles, the in vitro metabolism was inhibited when the incubation mixture contained either SKF-525A, carbon monoxide, or microsomes from mice treated with carbon tetrachloride. When mice were closed with ethyl alcohol, metabolic enhancement of nitriles was seen compared with the control. However, ethyl alcohol, when added to the incubation mixture, inhibited the in vitro metabolism of nitriles.
Tanii H; Juzen Igakkai Zasshi 94 (4): 664-77 (1985)

12.1.17 Antidote and Emergency Treatment

A person who has inhaled the vapors should be moved to an uncontaminated environment, and cardiopulmonary resuscitation should be administered. If the victim breathes with difficulty, oxygen should be given. In case of eye contact, flush with copious water for at least 20 min and call a physician. In case of ingestion, induce vomiting and call a physician. For skin contact, wash with plenty of soap and water.
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V15 900 (1981)
Rapid support of respiration & circulation is essential to successful treatment of cyanide intoxication. Massive cyanide overdoses have survived with only good supportive care. Immediate attention should be directed toward assisted ventilation, admin of 100% oxygen, insertion of iv lines, & institution of cardiac monitoring. Obtain an arterial blood gas immediately & correct any severe metabolic acidosis (pH below 7.15). Oxygen (100%) should be used routinely in moderate or severely symptomatic patients even in the presence of a normal pO2, since 100% O2 incr O2 delivery, may reactivate cyanide-inhibited mitochondrial enzymes, & potentiates the effect of thiosulfate. Avoid mouth to mouth resuscitation during CPR in order to prevent self poisoning. /Cyanides/
Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1480
Amyl nitrite perles are designed to produce 3% to 5% methemoglobinemia while an iv line is established for iv sodium nitrite. As a temporizing measure, the patient inhales the vapors until the sodium nitrite is ready. Because of the variability in methemoglobin production & the potential for cardiovascular collapse, this step may be omitted if sodium nitrite is readily available & the patient is not in extremis. Adequate ventilation & oxygenation are more important than admin of amyl nitrite. One perle (0.2 ml) is crushed & inhaled for 30 sec every min until iv nitrite is given. Sodium nitrite (3% soln), as 10 ml of a 3% soln (eg, 300 mg), is admin iv slowly over 4 min to produce a 20% methemoglobin level in adults. Children should receive 0.33 ml of the 3% soln/kg initially at an infusion rate of 2.5 ml/min, up to a maximum of 10 ml. Administer sodium nitrite doses to children on the basis of body weight, since fatal methemoglobinemia has occurred in children. /Cyanides/
Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1481
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilation if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Administer amyl nitrite ampules as per protocol and physician order ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Cyanide and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 388
For more Antidote and Emergency Treatment (Complete) data for ADIPONITRILE (6 total), please visit the HSDB record page.

12.1.18 Human Toxicity Excerpts

A case history of human exposure ... reported the effects of drinking "a few milliliters" of adiponitrile by an 18 yr old male. About 20 min after ingestion he experienced tightness in the chest, headache, weakness with difficulty in standing, and vertigo. He became cyanotic, respirations were rapid, & he had low blood pressure & tachycardia. The pupils were dilated & barely reacted to light. He exhibited mental confusion & tonic-clonic contractions of limbs & facial muscles.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152-3
... Human skin exposure to adiponitrile result in skin irritation and inflammation ... one case in which adiponitrile caused massive destruction of the skin on one foot.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3153
HIGHLY TOXIC BY INGESTION, INHALATION & SKIN ABSORPTION. IT PRODUCES DISTURBANCES OF RESPIRATORY & CIRCULATORY SYSTEMS.
National Fire Protection Guide. Fire Protection Guide on Hazardous Materials. 10 th ed. Quincy, MA: National Fire Protection Association, 1991., p. 49-20
POISONING BY ADIPONITRILE RESEMBLES POISONING WITH HYDROCYANIC ACID ... .
Lefaux, R. Practical Toxicology of Plastics. Cleveland: CRC Press Inc., 1968., p. 108
For more Human Toxicity Excerpts (Complete) data for ADIPONITRILE (6 total), please visit the HSDB record page.

12.1.19 Non-Human Toxicity Excerpts

A 2 yr drinking water exposure of Wistar rats at 0.5, 5.0, & 50 ppm adiponitrile produced significant adrenal degeneration in female rats at all 3 conc & at 50 ppm in male rats. All body wt & organ wt ratios of spleen, liver, & kidney were within normal ranges.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152
Exposures of pregnant Sprague Dawley rats at 10, 100, & 500 ppm in drinking water did not change ... gestation, or viability of offspring. Exposure of mongrel dogs to approx 10, 100, 500, & 1000 ppm adiponitrile in the diet resulted in greatly decr food intake & vomiting at 1000 ppm. No hematologic abnormalities were found. Kidney & liver function were normal at 500 ppm & below.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152
MEDIAN LETHAL CONCN WAS 1.71 MG/L FOR ACUTE (4 HR) INHALATION OF ADULT MALE CHR-CD RATS. RATS WERE EXPOSED TO 0 (CONTROL), 0.03, 0.1 OR 0.3 MG VAPORIZED ADIPONITRILE/L FOR 10 6-HR PERIODS (5 EXPOSURE DAYS, 2 REST DAYS, 5 EXPOSURE DAYS). CLINICAL SIGNS DURING EXPOSURE INCL IRREGULAR RESPIRATION & MILD SALIVATION. AT 0.3 MG/L RATS SHOWED WT LOSS DURING 1ST 5 EXPOSURES FOLLOWED BY NORMAL RATE OF WT GAIN. AFTER 10 EXPOSURES, RATS IN THIS GROUP SHOWED INCR BLOOD GLUCOSE, UREA NITROGEN, CREATININE & URINE GLUCOSE; DECR ERYTHROCYTES COUNT, HEMOGLOBIN, LEUKOCYTE COUNT, RELATIVE NUMBER OF EOSINOPHILS, & URINE OSMOLALITY. RATS EXPOSED TO 0.1 MG/L HAD INCR UREA NITROGEN & LYMPHOCYTES & DECR NUMBER OF NEUTROPHILS & EOSINOPHILS. RATS FROM ALL GROUPS HAD NORMAL VALUES 14 DAYS AFTER LAST EXPOSURE.
SMITH LW, KENNEDY GL JR; TOXICOL APPL PHARMACOL 65 (2): 257 (1982)
Adiponitrile was evaluated for embryotoxic and teratogenic potential in rats. Mated Sprague Dawley rats were administered adiponitrile by gavage on gestation days 6-19, inclusive. Daily dosage levels (mg/kg body wt) were 0, 20, 40, and 80. There was evidence of maternal toxicity in the high dose group. Some maternal effects also were seen at the middle dosage. Slight fetotoxicity was observed at the highest dosage. No teratogenic effects were observed at any dosage level.
Johannsen FR et al; Fundam Appl Toxicol 7 (1): 33-40 (1986)
For more Non-Human Toxicity Excerpts (Complete) data for ADIPONITRILE (7 total), please visit the HSDB record page.

12.1.20 Non-Human Toxicity Values

LD50 Guinea pig sc 50 mg/kg
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 166
LD50 Rat oral 155 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 73
LD50 Mouse ip 40 mg/kg
Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 326
LC50 Rat inhalation 1.71 mg/l/4 hr
Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 326
For more Non-Human Toxicity Values (Complete) data for ADIPONITRILE (6 total), please visit the HSDB record page.

12.2 Ecological Information

12.2.1 Ecotoxicity Values

TLm Pimephales promelas (fathead minnow) 820 mg/l/96 hr (hard water) /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 166
TLm Pimephales promelas (fathead minnow) 1250 mg/l/96 hr (soft water) /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 166
TLm Bluegill sunfish 1250 mg/l/24 hr (soft water) /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 166
TLm Guppies 775 mg/l/96 hr (soft water) /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 166

12.2.2 US EPA Regional Screening Levels for Chemical Contaminants

Resident Soil (mg/kg)
8.50e+06
Industrial Soil (mg/kg)
3.60e+07
Resident Air (ug/m3)
6.30e+00
Industrial Air (ug/m3)
2.60e+01
Chronic Inhalation Reference Concentration (mg/m3)
6.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

12.2.3 US EPA Regional Removal Management Levels for Chemical Contaminants

Resident Soil (mg/kg)
2.60e+07
Industrial Soil (mg/kg)
1.10e+08
Resident Air (ug/m3)
1.90e+01
Industrial Air (ug/m3)
7.90e+01
Chronic Inhalation Reference Concentration (mg/m3)
6.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

12.2.4 Environmental Fate / Exposure Summary

Adiponitrile's production and use as an intermediate in the manufacture of nylon, organic synthesis, and as an extractant for aromatic hydrocarbons may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 6.79X10-4 mm Hg at 25 °C indicates adiponitrile will exist solely as a vapor in the ambient atmosphere. Vapor-phase adiponitrile will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 23 days. If released to soil, adiponitrile is expected to have very high mobility based upon an estimated Koc of 16. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.21X10-9 atm-cu m/mole. Microorganisms isolated from soil were able to use adiponitrile as their sole source of carbon. If released into water, adiponitrile is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Adiponitrile had a 5-day theoretical BOD of 40% in a river die-away study using unacclimated river water with a sewage inocula; the 12-day theoretical BOD was >100%. Thus, adiponitrile is expected to biodegrade in aquatic systems. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Chemical hydrolysis of adiponitrile is expected to be slow based on a chemical hydrolysis half-life of >150,000 yrs for acetonitrile. Occupational exposure to adiponitrile may occur by dermal contact with this compound at workplaces where adiponitrile is produced or used. (SRC)

12.2.5 Artificial Pollution Sources

Adiponitrile's production and use as an intermediate in the manufacture of nylon(1), organic synthesis(1), and as an extractant for aromatic hydrocarbons(2) may result in its release to the environment through various waste streams(SRC).
(1) Lewis RJ Sr, ed; Hawley's Condensed Chemical Dictionary 13th ed. NY, NY: John Wiley and Sons Inc, p. 23 (1997)
(2) McKinney RJ, DeVito SC; Kirk-Othmer Encycl Chem Tech 4th ed. NY, NY: John Wiley and Sons, Supp: 447 (1998)

12.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a log Kow of -0.32(2) and a regression-derived equation(3), indicates that adiponitrile is expected to have very high mobility in soil(SRC). Volatilization of adiponitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.21X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 6.79X10-4 mm Hg(4), and water solubility, 8.00X10+4 mg/l(5). Adiponitrile is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). In water, adiponitrile had a 5-day theoretical BOD of 40% in a river die-away study using unacclimated Ohio River water, 0.5-10 mg/l substrate concn and sewage inocula(6); the 12-day theoretical BOD was >100%(6); negligible degradation was observed after 2 days(6). In addition, microorganisms (Aeromonas sp.) isolated from soil were able to use adiponitrile as its sole source of carbon(7). Thus, adiponitrile may be expected to biodegrade in soil systems(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Tanii H, Hashimoto K; Arch Toxicol 57: 88-93 (1985)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(4) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng NY, NY: Hemisphere Pub Corp 5 Vol (1989)
(5) McKinney RJ, DeVito SC; Kirk-Othmer Encycl Chem Tech 4th ed. NY, NY: John Wiley and Sons, Supp: 444 (1998)
(6) Ludzack FJ et al; Sewage Ind Wastes 31: 33-44 (1959)
(7) Kuwahara M et al; Hakkokogaku Kaishi 58: 441-8 (1980)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a log Kow of -0.32(2) and a regression-derived equation(3), indicates that adiponitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.21X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 6.79X10-4 mm Hg(4), and water solubility, 8.00X10+4 mg/l(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Adiponitrile had a 5-day theoretical BOD of 40% in a river die-away study using unacclimated Ohio River water, 0.5-10 mg/l substrate concn and sewage inocula(8); the 12-day theoretical BOD was >100%(8); negligible degradation was observed after 2 days(8). Thus, adiponitrile is expected to biodegrade in aquatic systems(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Tanii H, Hashimoto K; Arch Toxicol 57: 88-93 (1985)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng NY, NY: Hemisphere Pub Corp 5 Vol (1989)
(5) McKinney RJ, DeVito SC; Kirk-Othmer Encycl Chem Tech 4th ed. NY, NY: John Wiley and Sons, Supp: 444 (1998)
(6) Franke C et al; Chemosphere 29: 1501-14 (1994)
(7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(8) Ludzack FJ et al; Sewage Ind Wastes 31: 33-44 (1959)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), adiponitrile, which has a vapor pressure of 6.79X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase adiponitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 23 days(SRC), calculated from its rate constant of 7.12X10-13 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng NY, NY: Hemisphere Pub Corp 5 Vol (1989)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

12.2.7 Environmental Biodegradation

AEROBIC: Adiponitrile had a 5-day theoretical BOD of 40% in a river die-away study using unacclimated Ohio River water, 0.5-10 mg/l substrate concn and sewage inocula(1); a 12-day theoretical BOD was >100%(1); negligible degradation was observed after 2 days(1). At a substrate concn of 40 mg/l and 20 °C, adiponitrile had theoretical CO2 evolutions of 10 and 60% after 2 and 9 days, respectively, in river die-away studies using unacclimated Ohio River water and sewage inocula(1); at 5 °C, theoretical CO2 evolution was 10 and 60% after 7.5 and 33 days, respectively(1). At 20 °C, effects of acclimation were examined by redosing at an initial substrate concn of 40 mg/l; the ratio of time it took to achieve 60% oxidation on 1st and 2nd feeding was 2.1 to 1(1). Adiponitrile was found to be toxic to one activated sludge unit after 72 hrs with a metal substrate concn of 500 mg/l; the other two sludge units had 2.2-2.8% theoretical BOD(2). Using a bench scale activated sludge unit, 93-98% BOD removal of adiponitrile was achieved using an influent concn equivalent to 275-350 mg/l BOD and a mean aeration retention time of 7-13 hours(3). Adiponitrile, present at 30 mg/l, reached 85% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 100 mg/l and the Japanese MITI test(4). Microorganisms (Aeromonas sp.) isolated from soil were able to use adiponitrile as their sole source of carbon(5).
(1) Ludzack FJ et al; Sewage Ind Wastes 31: 33-44 (1959)
(2) Lutin PA; J Water Poll Contr Fed 42: 1632-42 (1970)
(3) Ludzack FJ et al; Proc of the 14th Industrial Waste Conf, Eng Ext Ser 104: 547-65 (1959)
(4) CITI; Biodegradation and Bioaccumulation Data of Existing Chemicals Database on Adiponitrile (111-69-3). Available from the Database Query page at https://www.cerij.or.jp/ceri_en/index_e4.shtml as of Jan 1, 2001.
(5) Kuwahara M et al; Hakkokogaku Kaishi 58: 441-8 (1980)

12.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of adiponitrile with photochemically-produced hydroxyl radicals has been estimated as 7.12X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 23 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chemical hydrolysis is expected to be slow, based on a chemical hydrolysis half-life of >150,000 yrs for acetonitrile(2). Adiponitrile is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Ellington JJ et al; Measurement of Hydrolysis Rate Constants for Evaluation of Hazardous Waste Land Disposal. Vol 3 USEPA/600/3-88/028 p. 18 (1988)

12.2.9 Environmental Bioconcentration

An estimated BCF of 3 was calculated for adiponitrile(SRC), using a log Kow of -0.32(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Tanii H, Hashimoto K; Arch Toxicol 57: 88-93 (1985)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.10 Soil Adsorption / Mobility

The Koc of adiponitrile is estimated as 16(SRC), using a measured log Kow of -0.32(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that adiponitrile is expected to have very high mobility in soil(SRC).
(1) Tanii H, Hashimoto K; Arch Toxicol 57: 88-93 (1985)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 17-28 (1983)

12.2.11 Volatilization from Water / Soil

The Henry's Law constant for adiponitrile is estimated as 1.21X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 6.79X10-4 mm Hg(1), and water solubility, 8.00X10+4 mg/l(2). This Henry's Law constant indicates that adiponitrile is expected to be essentially nonvolatile from moist soil and water surfaces(3). Adiponitrile is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng NY, NY: Hemisphere Pub Corp 5 Vol (1989)
(2) McKinney RJ, DeVito SC; Kirk-Othmer Encycl Chem Tech 4th ed. NY, NY: John Wiley and Sons, Supp: 444 (1998)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

12.2.12 Environmental Water Concentrations

DRINKING WATER: Adiponitrile was tentatively identified in drinking water collected in New Orleans, LA on Jan 14, 1976(1).
(1) Lucas SV; GC/MS Analysis of Organics in Drinking Water Concentrates and Advanced Waste Treatment Concentrates: Vol 2. Computer-Printed Tabulations of Compound Identification Results for Large-Volume Concentrates USEPA-600/1-84- 020B NTIS PB-128239 p.10 (1984)

12.2.13 Effluent Concentrations

Identified in effluent from a nylon manufacturing plant during Aug 1973(1).
(1) Shackelford WM, Keith LH; Frequency of Organic Compounds Identified in Water USEPA-600/4-76-062 p. 56 (1976)

12.2.14 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 478 workers (41 of these are female) are potentially exposed to adiponitrile in the US(1). Occupational exposure to adiponitrile may occur by dermal contact(2) with this compound at workplaces where adiponitrile is produced or used(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)
(2) Parmeggiani L, ed; Encycl of Occup Health and Safety 3rd ed Geneva, Switzerland: Intern Labour Organ 2: 1446-7 (1983)

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 ChemIDplus

17.3 CAMEO Chemicals

17.4 UN GHS Classification

17.5 NORMAN Suspect List Exchange Classification

17.6 EPA DSSTox Classification

17.7 EPA TSCA and CDR Classification

17.8 EPA Substance Registry Services Tree

17.9 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. ILO-WHO International Chemical Safety Cards (ICSCs)
  4. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. EPA Chemical Data Reporting (CDR)
    LICENSE
    The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes.
    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
  8. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. EPA Integrated Risk Information System (IRIS)
  11. EPA Provisional Peer-Reviewed Toxicity Values (PPRTVs)
  12. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  13. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  14. Hazardous Substances Data Bank (HSDB)
  15. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  16. NJDOH RTK Hazardous Substance List
  17. Occupational Safety and Health Administration (OSHA)
    LICENSE
    Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license.
    https://www.dol.gov/general/aboutdol/copyright
  18. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  19. The National Institute for Occupational Safety and Health (NIOSH)
    LICENSE
    The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations.
    https://www.cdc.gov/Other/disclaimer.html
  20. Emergency Response Guidebook (ERG)
  21. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  22. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  23. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  24. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  25. EPA Regional Screening Levels for Chemical Contaminants at Superfund Sites
  26. NITE-CMC
    Adiponitrile - FY2009 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/09-mhlw-2059e.html
    Adiponitrile - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-0005e.html
  27. NMRShiftDB
  28. MassBank Europe
  29. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  30. SpectraBase
  31. Japan Chemical Substance Dictionary (Nikkaji)
  32. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  33. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  34. Springer Nature
  35. SpringerMaterials
  36. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  37. Wikidata
  38. Wikipedia
  39. PubChem
  40. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  41. GHS Classification (UNECE)
  42. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  43. EPA Substance Registry Services
  44. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  45. PATENTSCOPE (WIPO)
CONTENTS