# PHYSICAL-CHEMICAL PROPERTIES AND FATE CHARACTERIZATION

Chemical Category Name

Glycol Ethers (Glymes)

Triethylene glycol dibutyl ether (CASRN: 63512-36-7)

[CA Name: 5,8,11,14-Tetraoxaoctadecane]

Pentaethylene glycol dibut yl ether (CASRN: 51105-00-1)

[CA Name: 5,8,11,14,17,20-Hexaoxatetracosane]

Polyethylene glycol dibutyl ether (CASRN: 31885-97-9)

[CA Name: Poly(oxy-1,2-ethanediyl ), .alpha.-butyl-.omega.-butoxy-]

3,6,9,12,15,18-Hexaoxaeicosane (CASRN: 23601-39-0)

[CA Name: 3,6,9,12,15,18-Hexaoxaeicosane]

3,6,9,12,15-Pentaoxaheptadecane (CASRN: 4353-28-0)

[CA Name: 3,6,9,12,15-Pentaoxaheptadecane]

Ethylene glycol diethy l ether (CASRN: 629-14-1)

[CA Name: Ethane, 1,2-diethoxy-]

5,8,11,14,17-Pentaoxaheneicosane (CASRN: 112-98-1)

[CA Name: 5,8,11,14,17-Pentaoxaheneicosane]

Triethylene glycol dimethyl ether (CASRN: 112-49-2)

[CA Name: 2,5,8,11-Tetraoxadodecane]

Diethylene glycol diethy l ether (CASRN: 112-36-7)

[CA Name: Ethane, 1,1'-oxybis[2-ethoxy-]

Diethylene glycol dimethyl ether (CASRN: 111-96-6)

[CA Name: Ethane, 1,1'-oxybis[2-methoxy-]

Ethylene glycol dimethyl ether (CASRN: 110-71-4)

[CA Name: Ethane, 1,2-dimethoxy- ]

August 2009

Prepared by

Exposure Assessment Branch

Economics Exposure and Technology Division

Office of Pollution Prevention and Toxics

Environmental Protection Agency

1200 Pennsylvania Avenue, NW

Washington, DC 20460-0001

# Summary-Conclusion

Glycol ethers (glymes) are liquids at room temperature with moderate to high water solubility and low to high vapor

pressure. Water solubility and vapor pressure tend to d ecrease with increasing chain length. The members of the

glycol ethers (glymes) are expected to possess high mobilit y in soil. Volatilization is considered low to moderate

based on the estimated Henry’s Law cons tants, with the expected rate of volatilization decreasing with increasing

chain length. The rate of hydrolysis is considered neglig ible. The members of glycol ethers (glymes) are expected

to have moderate persistence (P2) and low bioaccumulation potential (B1).

1. Physical-Chemical Properties and Environmental Fate

The physical-chemical properties of glycol ethers (glymes) are summarized in Table 1a, while the environmental

fate properties are provided in Table 1b. The chemical stru ctures of the members of glyc ol ethers (glymes) category

are provided in the Appendix.

Physical-Chemical Properties Characterization

Glycol ethers (glymes) are liquids at room temperature with moderate to high water solubility and low to high vapor

pressure. Water solubility and vapor pressure tend to decrease with increasing chain length.

Environmental Fate Characterization

The members of the glycol ethers (glymes) are expected to possess high mobility in soil. Based on the results from

a ready biodegradation test for ethane, 1,1'-oxybis[2-methoxy-] (CASRN 111-96-6), the members of this category

are not expected to be readily biod egradable. Various aerobic studies for members of this category and the

supporting chemical 2,5,8,11-tetraoxadodecane (CASRN 112-49-2) indicate that the rate of biodegradation is

moderate. An acclimation period of up to 35 days may occur before degradation is observed. Volatilization is

considered low to moderate based on the estimated Henry’ s Law constants, with the expected rate of volatilization

decreasing with increasing chain length. The rate of hydrolysis is considered negligible. The members of glycol

ethers (glymes) are expected to have moderate pe rsistence (P2) and low bioaccumulation potential (B1).

Conclusion: Glycol ethers (glymes) are liquids at room temperat ure with moderate to high water solubility and low

to high vapor pressure. Water solubility and vapor pressu re tend to decrease with increasing chain length. The

members of the glycol ethers (glymes) are expected to po ssess high mobility in soil. Volatilization is considered

low to moderate based on the estimated Henry’s Law consta nts, with the expected rate of volatilization decreasing

with increasing chain length. The rate of hydrolysis is considered negligible. The members of glycol ethers

(glymes) are expected to have moderate persis tence (P2) and low bioaccumulation potential (B1)Table 1a. Physical-Chemical Properties of Glycol Ethers (Glymes)Chemical Name CASRN MolecularWeightPhysical State MeltingPoint Boiling Point VaporPressureWaterSolubilityDissociationConstant(pKa)Henry’s LawConstantLog KowSponsored ChemicalsEthane, 1,2-dimethoxy-1110-71-4 90.12 Liquid -58oC(measured)85oC(measured)48 mm Hg at20oC(measured)1×106mg/L at20oC(miscible)(measured)Not applicable 5.7×10-6atmm3/mole at25oC(estimated)2-0.21(measured)Ethane, 1,2-diethoxy-1629-14-1 118.8 Liquid -74oC(measured)119.4oC(measured)33.7 mm Hg at25oC(measured)8.37×104mg/Lat 25oC(miscible)(measured)Not applicable 6.3×10-5atmm3/mole at25oC(estimated)20.66(measured)Ethane, 1,1'-oxybis[2-methoxy-3111-96-6 134.18 Liquid -68oC(measured)162oC(measured)2.96 mm Hg at25oC(measured)>1×106mg/Lat 25oC(miscible)(measured)Not applicable 5.2×10-7atmm3/mole at25oC(estimated)2-0.36(measured)Ethane, 1,1'-oxybis[2-ethoxy-1112-36-7 162.23 Liquid -45oC(measured)188oC(measured)0.521 mm Hgat 25oC(measured)1×106mg/L at20oC(miscible)(measured)Not applicable 1.1×10-7atmm3/mole at25oC(estimated)20.39(measured)3,6,9,12,15-Pentaoxaheptadecane4353-28-0 250.34 No data No data 296oC(estimated)2.1×10-3mmHg at 25oC(estimated)2.6×104mg/Lat 25oC(estimated)Not applicable <1×10-10atmm3/mole at25oC(estimated)-0.05(estimated)5,8,11,14-Tetraoxa-octadecane163512-36-7 262.39 No data No data 310oC(estimated)9.3×10-4mmHg at 25oC(estimated)270 mg/L at25oC(estimated)Not applicable 1.8×10-8atmm3/mole at25oC(estimated)2.2 (estimated)3,6,9,12,15,18-Hexaoxaeicosane123601-39-0 294.39 No data No data 340oC(estimated)1.1×10-4mmHg at 25oC(estimated)2.5×104mg/Lat 25oC(estimated)Not applicable <1×10-10atmm3/mole at25oC(estimated)-0.32(estimated)5,8,11,14,17-Pentaoxaheneicosane1112-98-1 306.45 No data No data 350oC(estimated)5.8×10-5mmHg at 25oC(estimated)260 mg/L at25oC(estimated)Not applicable 2.8×10-10atmm3/mole at25oC(estimated)1.9 (estimated)5,8,11,14,17, 20-Hexaoxa-tetracosane151105-00-1 350.50 No data No data 380oC(estimated)4.8×10-6mmHg at 25oC(estimated)240 mg/L at25oC(estimated)Not applicable <1×10-10atmm3/mole at25oC(estimated)1.6 (estimated)Poly(oxy-1,2-ethanediyl), .alpha.-butyl-.omega.-butoxy-131885-97-9 >300 Liquid -44oC(MW~300)4>300oC(MW~300)49.3×10-4to4.8×10-6mm Hg at25oC(estimated)2,5240–270 mg/Lat 25oC(estimated)2,5Not applicable 1.8×10-8to<1×10-10atmm3/mole at25oC(estimated)2,51.6–2.2(estimated)2,5Table 1a. Physical-Chemical Properties of Glycol Ethers (Glymes)Chemical Name CASRN MolecularWeightPhysical State MeltingPoint Boiling Point VaporPressureWaterSolubilityDissociationConstant(pKa)Henry’s LawConstantLog Kow2,5,8,11-Tetraoxadodecane1112-49-2 178.23 Liquid -45oC(measured)216oC(measured)4.03×10-2mmHg at 25oC(measured)1×106mg/L at25oC(miscible)(estimated)2Not applicable 3.2×10-9atmm3/mole at25oC(estimated)2-0.76(estimated)21SRC. 2009. The Physical Properties Database(PHYSPROP). SRC: Syracuse, NY. Available fromhttp://www.srcinc.com/what-we-do/free-demos.aspxas of July 13, 2009.2U.S. EPA. 2009. Estimation Programs Interface SuiteTM for Microsoft® Windows, v4.00.U.S. Environmental Protection Agency, Washington, DC, USA. Available from:http://www.epa.gov/opptintr/exposure/pubs/episuitedl.htmas of July 13, 2009.3Ferro Corporation. January12, 2004. Revised Roust Summary and Test Plan for Diglyme. Available from:http://epa.gov/chemrtk/pubs/summaries/diglyme/c15023tc.htmas of July 13, 2009.4Clariant. Ethylene glycoldibutyl ethers (butyl glymes). Available from:http://www.glymes.com/businesses/glymes/internet.nsf/vwWebPagesByID/951BA3D1E4E4EFAAC125722C003AE2B6asof July 10, 2009.5Estimations based on commercial polymer Polyglycol BB 300 (n = 3–5).Table 1b. Environmental Fate Characteristics of Glycol Ethers (Glymes)Chemical Name CASRN Photodegradation Half-life2,3HydrolysisHalf-lifeBiodegradation Bioaccumula-tion Factor2Log Koc2Fugacity(Level IIIModel)2Air (%)Water (%)Soil (%)Sediment (%)Persistence1Bioaccumulation1Sponsored ChemicalsEthane, 1,2-dimethoxy- 110-71-4 4.7 hours(estimated)Stable No data BAF = 0.94(estimated)0.38 (estimated) 1.34653<0.1P2 B1Ethane, 1,2-diethoxy- 629-14-1 2.2 hours(estimated)Stable 70% after 8 daysin river water, ~35day acclimationperiod;40.10 g/g 10-dayBOD4BAF = 1.3(estimated)0.90 (estimated) 1.14356<0.1P2 B1Ethane, 1,1'-oxybis[2-methoxy111-96-6 7.3 hours(estimated)Stable 0.1% after 5 days(OECD 301D)(not readilybiodegradable)5;0% after 28 days(OECD 301C)(not readilybiodegradable)6;31–42% after28 days (OECD302B) (notinherentlybiodegradable);Not detected after51-week SAGALcontinuous reactortest;37.0% removalafter 33-weekbatch culture test7;33% after 25days, 7 day lagperiod in activatedsludge4BAF = 0.92(estimated)0.29 (estimated)20.50560.438.90.113P2 B1Ethane, 1,1'-oxybis[2-ethoxy-2112-36-7 4.8 hours(estimated)Stable 21.7% after 33week batchculture test4;0.10 g/g 10-dayBOD (4.2%thBOD) at 20oC4BAF = 1.1(estimated)1.0 (estimated) 0.83762<0.1P2 B1Table 1b. Environmental Fate Characteristics of Glycol Ethers (Glymes)Chemical Name CASRN Photodegradation Half-life2,3HydrolysisHalf-lifeBiodegradation Bioaccumula-tion Factor2Log Koc2Fugacity(Level IIIModel)2Air (%)Water (%)Soil (%)Sediment (%)Persistence1Bioaccumulation13,6,9,12,15-Pentaoxaheptadecane4353-28-0 1.9 hours(estimated)Stable No data BAF = 0.95(estimated)1.0 (estimated) <0.13565<0.1P2 B15,8,11,14-Tetraoxaoctadecane63512-36-7 1.9 hours(estimated)Stable No data BAF = 13(estimated)1.8 (estimated) <0.121790.089P2 B13,6,9,12,15,18-Hexaoxaeicosane23601-39-0 1.6 hours(estimated)Stable No data BAF = 0.92(estimated)1.0 (estimated) <0.135650.084P2 B15,8,11,14,17-Pentaoxaheneicosane112-98-1 1.6 hours(estimated)Stable No data BAF = 7.4(estimated)1.7 (estimated) <0.122780.084P2 B15,8,11,14,17, 20-Hexaoxa-tetracosane51105-00-1 1.4 hours(estimated)Stable No data BAF = 4.3(estimated)1.6 (estimated) <0.12377<0.1P2 B1Poly(oxy-1,2-ethanediyl), .alpha.-butyl-.omega.-butoxy31885-97-9 1.4–1.9 hours(estimated)2,8Stable 10.8% after 14days in activatedsludge inoculum(MW ~1,500)Aerobic study9BAF = 4.3–13(estimated)2,81.6–1.8(estimated)1,8<0.121-2377-79<0.1P2 B1Table 1b. Environmental Fate Characteristics of Glycol Ethers (Glymes)Chemical Name CASRN Photodegradation Half-life2,3HydrolysisHalf-lifeBiodegradation Bioaccumula-tion Factor2Log Koc2Fugacity(Level IIIModel)2Air (%)Water (%)Soil (%)Sediment (%)Persistence1Bioaccumulation12,5,8,11-Tetraoxadodecane112-49-2 2.9 hours(estimated)Stable Slightdisappearanceafter 51 weeks inSAGALcontinuous reactorwith activatedsludge;<10.6%degradation after33 week batchculture7;94% after 28 days(readilybiodegradable)(measured fortetraethyleneglycolmonomethyl ether[CASRN 23783-42-8])6BAF = 0.90(estimated)1.0 (estimated) <0.13169<0.1P2 B11Federal Register. 1999. Categoryfor Persistent, Bioaccumulative, andToxic New Chemical Substances.Federal Register 64, Number 213 (November 4, 1999) pp. 60194–60204.2U.S. EPA. 2009. Estimation Programs Interface SuiteTM for Microsoft® Windows, v4.00.U.S. Environmental Protection Agency, Washington, DC, USA. Available from:http://www.epa.gov/opptintr/exposure/pubs/episuitedl.htmas of July 13, 2009.3SRC. 2009. The Physical Properties Database(PHYSPROP). SRC: Syracuse, NY. Available fromhttp://www.srcinc.com/what-we-do/free-demos.aspxas of July 13, 2009.4HSDB. 2009. Hazardous Substance Databank. National Library of Medicine. Database query available at:http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDBas of July 13, 2009.5Ferro Corporation. January12, 2004. Revised Roust Summary and Test Plan for Diglyme. Available from:http://epa.gov/chemrtk/pubs/summaries/diglyme/c15023tc.htmas of July 13, 2009.6National Institute of Technology and Evaluation. 2002. Biodegradation and Bioaccumulation of the Existing Chemical Substancesunder the Chemical SubstancesControl Law. Available from:http://www.safe.nite.go.jp/english/kizon/KIZON_start_hazkizon.htmlas of July 13, 2009.7Cowan RM, Kwon J. 1999. Aerobic biodegradation of ethylene glycol ether. In: Hazardous Industrial Wastes, 31st, Technomic Publishing Co, Inc. pp. 273-282.8Estimations based on commercial polymer Polyglycol BB 300 (n = 3–5).9Kawai, F. 1994. Biodegradation of polyethers and polyacrylate. In: Stud Polym Sci12 (Biodegradable Plastics and Polymers).pp. 24-38.

# APPENDIX

Typical Constituents of Glycol Ethers (Glymes)

Sponsored Chemical

Name CASRN Structure

Ethane, 1,2-dimethoxy110-71-4 O

O CH 3



# H 3 

# C



# Ethane, 1,2-diethoxy- 629-14-1 O

O H 3 

# C CH 3



# Ethane, 1,1'-oxybis[2-

methoxy111-96-6

O O

H 3 

# C O

CH 3



# Ethane, 1,1'-oxybis[2-

ethoxy112-36-7 O

O H 3 

# C O CH 3



# 5,8,11,14-Tetraoxaoctadecane 63512-36-7

O O

O O

H 3 

# C



# 3,6,9,12,15-Pentaoxaheptadecane 4353-28-0 O

O O

O H 3 

# C O



# 5,8,11,14,17-Pentaoxaheneicosane 112-98-1

H 3 

# C O O

O O



# 3,6,9,12,15,18-Hexaoxaeicosane 23601-39-0 O

O O

O O H 3 

# C



# 5,8,11,14,17,20-Hexaoxatetracosane 51105-00-1

O O

O O O

O H 3 

# C



# Poly(oxy-1,2-ethanediyl), .alpha.-butyl-

.omega.-butoxy31885-97-9



# H 3 

# C O O CH 3



# n

2,5,8,11-Tetraoxadodecane 112-49-2 O

O O

H 3 

# C O C