An official website of the United States government

Ethylene glycol dibutyl ether

PubChem CID
8188
Structure
Ethylene glycol dibutyl ether_small.png
Ethylene glycol dibutyl ether_3D_Structure.png
Molecular Formula
Synonyms
  • Ethylene glycol dibutyl ether
  • 112-48-1
  • Ethylene glycol di-n-butyl ether
  • 1,2-DIBUTOXYETHANE
  • Glycol dibutyl ether
Molecular Weight
174.28 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2024-12-27
Description
Ethylene glycol dibutyl ether is a colorless liquid. (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.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Ethylene glycol dibutyl ether.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(2-butoxyethoxy)butane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H22O2/c1-3-5-7-11-9-10-12-8-6-4-2/h3-10H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCOCCOCCCC
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C10H22O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C10H22O2

C4H9OC2H4OC4H9

2.3 Other Identifiers

2.3.1 CAS

112-48-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 DSSTox Substance ID

2.3.6 ICSC Number

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
174.28 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.5
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
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
174.161979940 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
174.161979940 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
18.5Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
64.2
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

Ethylene glycol dibutyl ether is a colorless liquid. (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.
Almost colorless liquid; [Hawley]
COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.

3.2.2 Color / Form

Almost colorless liquid
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 465

3.2.3 Odor

Slight odor
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 465

3.2.4 Boiling Point

399 °F at 760 mmHg (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.
203.3 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-146
203 °C

3.2.5 Melting Point

-69.1 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-146
-69 °C

3.2.6 Flash Point

185 °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.
185 °F (open cup)
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1543
185 °F (85 °C) (CLOSED CUP)
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 325-61
85 °C o.c.

3.2.7 Solubility

In water, 2.0X10+3 mg/L at 20 °C
EPA; U.S. EPA Solubility Database (Kawai K; J Osaka Univ Dent Sch 28: 153-160 (1988)
Solubility in water: poor

3.2.8 Density

0.8 (USCG, 1999) - Less dense than water; will float
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.
0.8319 at 25 °C/25 °C
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V3: 2672
Bulk density: 7.0 lb/gal at 20 °C ... combustible
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 465
Relative density (water = 1): 0.8

3.2.9 Vapor Density

Relative vapor density (air = 1): 6

3.2.10 Vapor Pressure

0.09 [mmHg]
VP: 0.12 mm Hg at 25 °C. 0.016% in saturated air at 25 °C; 1 ppm = 7.13 mg/cu m and 1 mg/L = 140 ppm at 25 °C, 760 mm Hg
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1543
9.0X10-2 mm Hg at 20 °C
Flick, E.W. (ed.). Industrial Solvents Handbook 4 th ed. Noyes Data Corporation., Park Ridge, NJ., 1991.
Vapor pressure, Pa at 20 °C: 12

3.2.11 LogP

log Kow = 2.48
Funasaki N et al; J Phys Chem 88: 5786-5790 (1984)

3.2.12 Decomposition

When heated to decomposition it emits acrid smoke and irritating fumes.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1155

3.2.13 Refractive Index

Index of refraction: 1.4112 at 25 °C/D
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-146

3.2.14 Kovats Retention Index

Standard non-polar
1160
Semi-standard non-polar
1144, 1117, 1130
Standard polar
1359, 1348

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Solvents

Solvents -> Glycol Ethers (E Series)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian A-60
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Varian HA-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
CI-B
Ionization Mode
positive
Top 5 Peaks

175 99.99

176 27.80

119 20

101 18.32

102 17.71

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 6
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

57 99.99

29 23.83

56 23.79

41 23.61

45 14.04

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2.2 Other MS

1 of 2
Authors
HASHIMOTO K, KYOTO COLLEGE OF PHARMACY
Instrument
HITACHI M-80
Instrument Type
CI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 100 eV
Top 5 Peaks

175 999

176 278

119 200

101 183

102 177

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 2
Authors
YAMAMOTO M, DEP. CHEMISTRY, FAC. SCIENCE, NARA WOMEN'S UNIV.
Instrument
HITACHI RMU-6M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

57 999

29 238

56 238

41 236

45 140

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
CAPILLARY FILM
Source of Spectrum
SCHOLL
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
CAPILLARY CELL: 0.015 MM
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 Vapor Phase IR Spectra

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 Use and Manufacturing

7.1 Uses

Sources/Uses
Used as a high-boiling inert solvent, e.g., in extraction applications; [Hawley]
Hawley - Lewis RJ. _Hawley's Condensed Chemical Dictionary, _15th Ed. New York: John Wiley & Sons, 2007.
High-boiling point inert solvent; specialized solvent and extraction applications.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 465
Solvent
Flick, E.W. (ed.). Industrial Solvents Handbook 4 th ed. Noyes Data Corporation., Park Ridge, NJ., 1991.

7.2 Methods of Manufacturing

Ethylene glycol monoethers are usually produced by reaction of ethylene oxide with the appropriate alcohol. A mixture of homologues is obtained ... The glycol monoethers can be converted to diethers by alkylation with common alkylating agents, such as dimethyl sulfate or alkyl halides ( Williamson synthesis). Glycol dimethyl ethers are formed by treatment of dimethyl ether with ethylene oxide. /Ethers/
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V12 601 (2003)

7.3 U.S. Production

(2006) 1,612 million lb annual capacity /Glycol ethers/
SRI Consulting. 2006 Directory of Chemical Producers-United States. Menlo Park, CA. 2006, p. 657

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Note
Pictograms displayed are for 66.7% (2 of 3) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Precautionary Statement Codes

P264+P265, P280, P305+P351+P338, and P337+P317

(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 3 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 2 of 3 reports by companies with hazard statement code(s).

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.

8.1.2 Hazard Classes and Categories

Eye Irrit. 2 (66.7%)

8.1.3 NFPA Hazard Classification

NFPA 704 Diamond
1-2-0
NFPA Health Rating
1 - Materials that, under emergency conditions, can cause significant irritation.
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
0 - Materials that in themselves are normally stable, even under fire conditions.

8.1.4 Health Hazards

Moderately toxic by ingestion and skin contact. Irritates skin and eyes. (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.

8.1.5 Fire Hazards

Special Hazards of Combustion Products: On decomposition, it emits acrid smoke and irritating fumes. (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.
Combustible. Above 85 °C explosive vapour/air mixtures may be formed.

8.1.6 Hazards Summary

In animal experiments, effects include changes in erythrocyte count; [RTECS] A mild skin and eye irritant; Defats the skin; [ICSC] Oxidized by air producing unstable peroxides that can spontaneously explode; A skin and eye irritant; [CAMEO] See GLYCOL ETHERS.

8.1.7 Fire Potential

Combustible
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 465

8.2 First Aid Measures

Inhalation First Aid
Fresh air, rest.
Skin First Aid
Remove contaminated clothes. Rinse skin with plenty of water or shower.
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth.

8.2.1 First Aid

INHALATION: Call for medical aid. Remove from exposure

EYES: Flush with water for at least 15 minutes.

SKIN: Wash with copious amounts of water. (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.

8.3 Fire Fighting

Fire Extinguishing Agents Not to Be Used: Water may be ineffective.

Fire Extinguishing Agents: Dry chemical, alcohol foam, carbon dioxide. (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.
Use water spray, powder, alcohol-resistant foam, carbon dioxide.

8.4 Accidental Release Measures

8.4.1 Spillage Disposal

Collect leaking liquid in sealable containers. Wash away remainder with plenty of water.

8.4.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

8.5 Handling and Storage

8.5.1 Safe Storage

Separated from strong oxidants. Ventilation along the floor.

8.6 Exposure Control and Personal Protection

8.6.1 Inhalation Risk

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

8.6.2 Effects of Short Term Exposure

The substance is mildly irritating to the eyes and skin.

8.6.3 Effects of Long Term Exposure

The substance defats the skin, which may cause dryness or cracking.

8.6.4 Personal Protective Equipment (PPE)

Protective goggles or face shield; rubber gloves. (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.

8.6.5 Preventions

Fire Prevention
NO open flames. Above 85 °C use a closed system and ventilation.
Inhalation Prevention
Use ventilation.
Skin Prevention
Protective gloves.
Eye Prevention
Wear safety spectacles.
Ingestion Prevention
Do not eat, drink, or smoke during work.

8.7 Stability and Reactivity

8.7.1 Air and Water Reactions

Oxidizes in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164].

8.7.2 Reactive Group

Ethers

8.7.3 Reactivity Alerts

Peroxidizable Compound

8.7.4 Reactivity Profile

ETHYLENE GLYCOL DIBUTYL ETHER may react violently with strong oxidizing agents. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. May initiate the polymerization of isocyanates and epoxides. Relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond.

8.7.5 Hazardous Reactivities and Incompatibilities

Glycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 491-142

9 Toxicity

9.1 Toxicological Information

9.1.1 Symptoms

Skin Exposure
Dry skin. Redness.
Eye Exposure
Redness.

9.1.2 Adverse Effects

Neurotoxin - Acute solvent syndrome

9.1.3 Acute Effects

9.1.4 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ ...Rated 2 on rabbit eyes. /Rated... on scale of 1 to 10 according to degree of injury observed after 24 hr, paying particular attention to condition of cornea. Most severe injuries have been rated 10./
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 1147

9.1.5 Non-Human Toxicity Values

LD50 Rat oral 3250 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1155
LD50 Rabbit dermal 3560 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1155

9.2 Ecological Information

9.2.1 Environmental Fate / Exposure Summary

Ethylene glycol dibutyl ether's production and use as a solvent may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.09 mm Hg at 25 °C indicates ethylene glycol dibutyl ether will exist solely in the vapor phase in the atmosphere. Vapor-phase ethylene glycol dibutyl ether 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 10 hours. If released to soil, ethylene glycol dibutyl ether is expected to have very high mobility based upon an estimated Koc of 17. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1X10-5 atm-cu m/mole. Biodegradation data were not available. If released into water, ethylene glycol dibutyl ether is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 4.9 and 39 days, respectively. An estimated BCF of 16 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to ethylene glycol dibutyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol dibutyl ether is produced or used. (SRC)

9.2.2 Artificial Pollution Sources

Ethylene glycol dibutyl ether's production and use as a solvent(1) may result in its release to the environment through various waste streams(SRC).
(1) Flick EW; Industrial Solvents Handbook 4th ed. Park Ridge, NJ: Noyes Data Corp (1991)

9.2.3 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that ethylene glycol dibutyl ether is expected to have very high mobility in soil(SRC). Volatilization of ethylene glycol dibutyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 0.09 mm Hg(3), and water solubility, 2000 mg/L(4). Ethylene glycol dibutyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data were not available(SRC, 2007).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Flick EW; Industrial Solvents Handbook 4th ed. Park Ridge, NJ: Noyes Data Corp (1991)
(4) EPA; U.S. EPA solubility database (K, Kawai (J Osaka Univ. Dent. Sch.,) vol.28, 153-160, (1988)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that ethylene glycol dibutyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.09 mm Hg(4), and water solubility, 2000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.9 and 39 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 16(SRC), from its log Kow of 2.48(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(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) Flick EW; Industrial Solvents Handbook 4th ed. Park Ridge, NJ: Noyes Data Corp (1991)
(5) Kawai K; J Osaka Univ Dent Sch 28: 153-160 (1988)
(6) Franke C et al; Chemosphere 29: 1501-14 (1994)
(7) Funasaki N et al; J Phys Chem 88: 5786-90 (1984)
(8) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol dibutyl ether, which has a vapor pressure of 0.09 mm Hg at 20 °C(2), will exist solely in vapor phase in the ambient atmosphere. Vapor-phase ethylene glycol dibutyl ether 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 10 hours(SRC), calculated from its rate constant of 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Flick EW; Industrial Solvents Handbook 4th ed. Park Ridge, NJ: Noyes Data Corp (1991)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

9.2.4 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of ethylene glycol dibutyl ether with photochemically-produced hydroxyl radicals has been estimated as 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Ethylene glycol dibutyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

9.2.5 Environmental Bioconcentration

An estimated BCF of 16 was calculated in fish for ethylene glycol dibutyl ether(SRC), using a log Kow of 2.48(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) Funasaki N et al; J Phys Chem 88: 5786-90 (1984)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

9.2.6 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of ethylene glycol dibutyl ether can be estimated to be 17(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethylene glycol dibutyl ether is expected to have very high mobility in soil(SRC).
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)

9.2.7 Volatilization from Water / Soil

The Henry's Law constant for ethylene glycol dibutyl ether is estimated as 1X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 0.09 mm Hg(1), and water solubility, 2000 mg/L(2). This Henry's Law constant indicates that ethylene glycol dibutyl ether is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 4.9 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 39 days(SRC). Ethylene glycol dibutyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Ethylene glycol dibutyl ether is not expected to
(1) Flick EW; Industrial Solvents Handbook 4th ed. Park Ridge, NJ: Noyes Data Corp (1991)
(2) Kawai K; J Osaka Univ Dent Sch 28: 153-160 (1988)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

9.2.8 Probable Routes of Human Exposure

Occupational exposure to ethylene glycol dibutyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol dibutyl ether is produced or used. (SRC)

10 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Solvents, acute toxic effect [Category: Acute Poisoning]

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Taxonomy

14 Classification

14.1 ChemIDplus

14.2 CAMEO Chemicals

14.3 UN GHS Classification

14.4 NORMAN Suspect List Exchange Classification

14.5 EPA DSSTox Classification

14.6 EPA Substance Registry Services Tree

14.7 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. 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
  2. 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/
    Poly(oxy-1,2-ethanediyl), α-butyl-ω-butoxy-
    https://commonchemistry.cas.org/detail?cas_rn=31885-97-9
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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
  7. Hazardous Substances Data Bank (HSDB)
  8. ILO-WHO International Chemical Safety Cards (ICSCs)
  9. 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
    Ethylene glycol dibutyl ether
    https://haz-map.com/Agents/5215
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. MassBank Europe
  12. 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
  13. 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
  14. SpectraBase
    Butane, 1,1'-[1,2-ethanediylbis(oxy)]bis-
    https://spectrabase.com/spectrum/COGoSPtvZ1N
    ETHYLENE GLYCOL DI-n-BUTYL ETHER
    https://spectrabase.com/spectrum/4mW1fsZjHOy
  15. Natural Product Activity and Species Source (NPASS)
  16. Springer Nature
  17. SpringerMaterials
  18. Wikidata
    ethylene glycol dibutyl ether
    https://www.wikidata.org/wiki/Q27252436
  19. PubChem
  20. GHS Classification (UNECE)
  21. 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/
  22. EPA Substance Registry Services
  23. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  24. PATENTSCOPE (WIPO)
CONTENTS