U.S. EPA Contaminated Site Cleanup Information (CLU-IN)


U.S. Environmental Protection Agency
U.S. EPA Technology Innovation and Field Services Division

Dense Nonaqueous Phase Liquids (DNAPLs)

Treatment Technologies

Bioremediation

Halogenated Alkanes


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Bromoform | Bromochloromethane | Dibromochloromethane | Bromodichloromethane | Methylene Chloride | Chloroform | Carbon Tetrachloride | Trichlorofluoromethane | Ethylene Dibromide | 1,1-Dichloroethane | 1,2-Dichloroethane | 1,1,1-Trichloroethane | 1,1,2-Trichloroethane | 1,1,2,2- Tetrachloroethane | 1,1,2-Trichlorotrifluoroethane | 1,2-Dibromo-3-chloropropane | 1,2-Dichloropropane

Bromoform

Review of bioremediation approaches indicates that bromoform is subject to anaerobic biodegradation but is sparingly degradable under aerobic conditions (ATSDR 2005).

References

Toxicological Profile for Bromoform and Chlorodibromomethane
Agency for Toxic Substances and Disease Registry (ATSDR), 273 pp, 2005

Bromochloromethane

Review of bioremediation approaches indicates that BCM can be degraded under anaerobic conditions (Howard 1993). Based on limited data, the compound possibly undergoes aerobic biodegradation (HSDB).

References

Chlorobromomethane, CASRN: 74-97-5
Hazardous Substances Data Bank (HSDB)
TOXNET, National Library of Medicine Web site.

Handbook of Environmental Fate and Exposure Data for Organic Chemicals, Volume IV: Solvents
Howard, P.
CRC Press, 578 pp, 1993

Dibromochloromethane

Review of bioremediation approaches indicates that DBCM is subject to anaerobic biodegradation and is sparingly degradable under aerobic conditions (ATSDR 2005).

References

Toxicological Profile for Bromoform and Chlorodibromomethane
Agency for Toxic Substances and Disease Registry (ATSDR), 273 pp, 2005

Bromodichloromethane

Review of bioremediation approaches indicates that BDCM can be degraded under anaerobic conditions (Howard 1990) but is not likely to undergo aerobic biodegradation (Fram et al. 2003). The compound can be degraded cometabolically (Wahman et al. 2003).

References

Cometabolism of Trihalomethanes by Nitrosomonas europaea
Wahman, D., L. Katz, and G. Speitel, Jr.
Applied and Environmental Microbiology 71(12):7980-7986(2005)

Handbook of Environmental Fate and Exposure Data for Organic Chemicals, Volume 2: Solvents
Howard, P. (ed).
CRC Press, 546 pp, 1990

Processes Affecting the Trihalomethane Concentrations Associated with the Third Injection, Storage, and Recovery Test at Lancaster, Antelope Valley, California, March 1998 through April 1999
Fram, M., B. Bergamaschi, K. Goodwin, R. Fujii, and J. Clark.
U.S. Geological Survey Water-Resources Investigations Report 03-4062, 83 pp, 2003

Methylene Chloride

Review of bioremediation approaches indicates that MC is subject to both anaerobic (FRTR 2000) and aerobic biodegradation (ITRC 1999).

References

In Situ Anaerobic Bioremediation at DOE's Pinellas Northeast Site, Largo, Florida (2000)
Federal Remediation Technologies Roundtable (FRTR) Cost and Performance Report Database.

Natural Attenuation of Chlorinated Solvents in Groundwater: Principles and PracticesAdobe PDF Logo
Interstate Technology and Regulatory Council (ITRC), ISB-3, 117 pp, 1999

Chloroform

Review of bioremediation approaches indicates that chloroform is degraded under anaerobic conditions; however it can be toxic to microbes at relatively low (0.1 mg/L) levels. Although the compound does not degrade readily under aerobic conditions (Watts et al. 2004), cometabolic degradation can be achieved under aerobic conditions (Seprini et al. 2001).

References

ChloroformAdobe PDF Logo
Watts, P., G. Long, and M. Meek.
World Health Organization, Geneva, Concise International Chemical Assessment Document 58, 64 pp, 2004

Final Report: Aerobic Cometabolism of Chloroform, 1,1,1-Trichloroethane, 1,1-Dichloroethylene, and Other Chlorinated Aliphatic Hydrocarbons by Microbes Grown on Butane and Propane
Semprini, L. and D. Arp.
U.S. EPA, National Center For Environmental Research, Grant R825689C019, Subproject 19, 2001

Carbon Tetrachloride

Review of bioremediation approaches indicates that CT is subject to anaerobic biodegradation through both reductive dechlorination and cometabolic action (ITRC 2002); however, the compound is very recalcitrant to aerobic biodegradation (ITRC 1999).

References

Natural Attenuation of Chlorinated Solvents in Groundwater: Principles and PracticesAdobe PDF Logo
Interstate Technology and Regulatory Cooperation (ITRC) Work Group, ISB-3, 123 pp, 1999

Trichlorofluoromethane

Review of bioremediation approaches indicates that TCFM can be degraded under anaerobic conditions; however, the process stops at dichlorofluoromethane under some anaerobic conditions (Scheutz et al. 2009, Brigmon et al. 2000, Sonier et al. 1994, Shana et al. 2010). Although TCFM is not likely to undergo aerobic biodegradation (Plummer and Busenberg 2000), it can be degraded cometabolically (Blackert and Cibrik 2009).

References

Dechlorination of Trichlorofluoromethane (CFC-11) by Sulfate-Reducing Bacteria from an Aquifer Contaminated with Halogenated Aliphatic Compounds.
Sonier, D.N. Duran, and G. Smith
Applied and Environmental Microbiology 60(12):4567-4572(1994)

In an anaerobic environment, TCFM was degraded to dichlorofluoromethane. View abstract

Evaluation of Strategies for Anaerobic Bioremediation of High Concentrations of Halomethanes
Shana, H., H.D. Kurtz Jr., and D.L. Freedman.
Water Research 44(5):1317-1328(2010)

Lactate and corn syrup electron donors were effective in completely reducing TCFM. View abstract

Chlorofluorocarbons Background
Plummer, L. and E. Busenberg.
Excerpted from Environmental Tracers in Subsurface Hydrology (P. Cook and A. Herczeg eds.), Kluwer Acadmic Press, Chapter 15: Chlorofluorocarbons 441-478(2000)

The authors state that TCFM does not degrade aerobically.

Compilation of Case Histories from More Than Eight Years of Successful Testing and Remediation Using Aerobic Soy Based Co-Metabolism For Removal of Chlorinated Hydrocarbons from GroundwaterAdobe PDF Logo
Blackert, D. and J. Cibrik.
The Business of Brownfields: 2009 Conference Proceedings, 15-17 April, Pittsburgh, PA. 8 pp, 2009

This paper discusses the development and testing of a soy methyl ester and a biodegradable surfactant blend to bring about aerobic cometabolic destruction of various organic compounds, including TCFM. The process uses air sparging to maintain aerobic conditions.

Biodegradation of Trichlorofluoromethane by Sediment Associated Anaerobic Bacteria from an Aquifer Contaminated by Landfill Leachate
Brigmon, R.L., D.J. Altman, A.J. Tien, M.M. Franck, and P.C. McKinsey.
WSRC-MS-2000-00311, 4 pp, 2000

Biodegradation of Methane and Halocarbons in Simulated Landfill Biocover Systems Containing Compost Materials
Scheutz, C., G. Pedersen, G. Costa, and P. Kjeldsen.
Journal of Environmental Quality 38:1363-1371(2009)

TCFM was anaerobically degraded to dichlorofluoromethane (DCFM). DCFM is subject to aerobic degradation. View longer abstract

Ethylene Dibromide

Review of bioremediation approaches indicates that EDB can be degraded under both aerobic conditions (ATSDR 1992 and DNR 2003) and anaerobic conditions (DNR 2003 and Henderson et al. 2008); however, it is persistent in the subsurface.

References

Toxicological Profile for 1,2-Dibromoethane
Agency for Toxic Substances and Disease Registry (ATSDR), 173 pp, 1992

Understanding Chlorinated Hydrocarbon Behavior in Groundwater: Investigation, Assessment and Limitations of Monitored Natural AttenuationAdobe PDF Logo
Wisconsin Department of Natural Resources (DNR), RR-699, 104 pp, 2003

Anaerobic Biodegradation of Ethylene Dibromide and 1,2-Dichloroethane in the Presence of Fuel Hydrocarbons
Henderson, J.K., D. Freedman, R. Falta, T. Kuder, and J. Wilson.
Environmental Science & Technology 42(3):864-870(2008)
View abstract

1,1-Dichloroethane

Review of bioremediation approaches indicates that 1,1-DCA is degraded poorly to not at all under aerobic conditions (van Agteren et al. 1998); however, there is evidence that the chemical can be degraded using aerobic cometabolism with a butane substrate (Semprini et al. 2007). 1,1-DCA can be degraded using anaerobic biostimulation and/or bioaugmentation, although the rate is slow, and the process potentially can stall at chloroethane (Ferris, et al. 2006, Best 1999, Grostern and Edwards 2006).

References

Handbook on Biodegradation and Biological Treatment of Hazardous Organic Compounds
van Agteren, M.H., S. Keuning, and D. Janssen.
Springer, 504 pp, 1998

Proceedings of the Fifth International Conference on Remediation of Chlorinated and Recalcitrant Compounds (Monterey, CA; May 2006)Adobe PDF Logo
Ferris, S., B. Henry, C. Coker, and R. Lantzy.
Battelle Press, Columbus, OH. Paper B-25, 2006

This paper documents the destruction of 1,1,1-TCA and 1,1-DCA at a site with the very slow degradation of chloroethane under anaerobic conditions.

Bioaugmentation of Butane-Utilizing Microorganisms for the In Situ Cometabolic Treatment of 1,1-Dichloroethene, 1,1-Dichloroethane, and 1,1,1-Trichloroethane
Semprini, L., M.E. Dolan, M.A. Mathias, G.D. Hopkins, and P.L. McCarty.
European Journal of Soil Biology 43(5-6):322-327(2007)
View abstract

A 1,1,1-Trichloroethane-Degrading Anaerobic Mixed Microbial Culture Enhances Biotransformation of Mixtures of Chlorinated Ethenes and Ethanes
Grostern, A. and E.A. Edwards.
Applied and Environmental Microbiology 72(12):7849-7856(2006)

Anaerobic Transformation of Chlorinated Hydrocarbons in a Packed-Bed Reactor
Best, Jappe Hinco de, Ph.D. dissertation, University of Groningen, 138 pp, 1999

This dissertation in part studies the anaerobic degradation of 1,1,1-TCA under methanogenic conditions and concludes that 1,1,1-TCA and degradation product 1,1-DCA are destroyed, but chloroethane is not.

1,2-Dichloroethane

Review of bioremediation approaches indicates that the compound can be degraded under anaerobic conditions (Dyer et al. 2000, De Wildeman et al. 2002, Grostern and Edwards 2009) and is also subject to aerobic biodegradation (Michiels 1994, Davis et al. 2009).

Example Site

Bridgeport Rental and Oil Services, New Jersey
U.S. EPA, Superfund Site Progress Profile.

The BROS site, a 30-acre parcel of land formerly used as a waste oil storage and recovery facility, is contaminated with LNAPL, PCBs, and many solvents, including 1,2-DCA. Treatment technologies chosen for remediation include on-site incineration, pump and treat, phytohydraulics, in situ bioremediation, bioslurping, and in situ chemical oxidation.

References

Aerobic Bioremediation of 1,2-Dichloroethane and Vinyl Chloride at Field Scale
Davis, G.B., B.M. Patterson, and C.D. Johnston.
Journal of Contaminant Hydrology 107(1-2):91-100(2009)
View abstract

Characterization of a Dehalobacter Coculture That Dechlorinates 1,2-Dichloroethane to Ethene and Identification of the Putative Reductive Dehalogenase Gene
Grostern, A. and E.A. Edwards
Applied and Environmental Microbiology 75(9): 2684-2693(2009)
View abstract

In Situ Bioremediation of 1,2-Dichloroethane Under Anaerobic Conditions
Dyer, M., E. van Heiningen, and J. Gerritse.
Geotechnical and Geological Engineering 18(4):313-334(2000)
View abstract

In-Situ Bioremediation of an Aquifer Contaminated with 1,2-Dichloroethane
Michiels, T. and D. Breugelmans.
Remediation Journal 5(1):101-110(1994)
View abstract

Reductive Biodegradation of 1,2-Dichloroethane by Methanogenic Granular Sludge: Perspectives for In Situ Remediation
De Wildeman, S., H. Nollet, H. Van Langenhove, G. Diekert, and W. Verstraete.
Water Science & Technology 45(10):43-48(2002)
View abstract

1,1,1-Trichloroethane

Review of bioremediation approaches indicates that 1,1,1-TCA is poorly degraded under aerobic conditions (ATSDR 2006 and Parkin 2000), whereas it can be degraded readily using anaerobic biostimulation and/or bioaugmentation (Parkin 2000). Its degradation products 1,1-dichloroethane and chloroethane are more recalcitrant, however, with some evidence that stalling could occur at chloroethane (Ferris et al. 2006, Best 1999, Grostern and Edwards 2006). Scheutz et al. (2011) reviewed the state of the science of TCA degradation in aquifers with an examination of results from lab experiments and 22 field case studies.

References

A 1,1,1-Trichloroethane-Degrading Anaerobic Mixed Microbial Culture Enhances Biotransformation of Mixtures of Chlorinated Ethenes and Ethanes
Grostern, A. and E.A. Edwards.
Applied and Environmental Microbiology 72(12):7849-7856(2006)
View abstract

Final Report: Application of Anaerobic and Multiple-Electron-Acceptor Bioremediation to Chlorinated Aliphatic Subsurface Contamination
Parkin, G.F.
U.S. EPA, National Center for Environmental Research, Grant R825549C053, Subproject 53, 2000

This research looked at the anaerobic biodegradation of PCE, 1,1,1-TCA, and carbon tetrachloride. All three can be degraded anaerobically.

Natural and Enhanced Anaerobic Degradation of 1,1,1-Trichloroethane and its Degradation Products in the Subsurface: A Critical Review
Scheutz, C., N.D. Durant, M.H. Hansen, and P.L. Bjerg.
Water Research 45(9):2701-2723(2011)
View abstract

Pilot Test Evaluation for Enhanced Anaerobic Bioremediation of Chlorinated Ethanes Adobe PDF Logo
Ferris, S., B. Henry, C. Coker, and R. Lantzy.
Proceedings of the Fifth International Conference on Remediation of Chlorinated and Recalcitrant Compounds (Monterey, CA; May 2006)

This paper documents the destruction of 1,1,1-TCA and 1,1-DCA at a site with the very slow degradation of chloroethane under anaerobic conditions.

Toxicological Profile for 1,1,1-Trichloroethane
Agency for Toxic Substances and Disease Registry (ATSDR), 371 pp, 2006

Anaerobic Transformation of Chlorinated Hydrocarbons in a Packed-Bed Reactor
Best, Jappe Hinco de, Ph.D. dissertation, University of Groningen, 138 pp, 1999

This dissertation in part studies the anaerobic degradation of 1,1,1-TCA under methanogenic conditions and concludes that 1,1,1-TCA and degradation product 1,1-DCA are destroyed, but chloroethane is not.

1,1,2-Trichloroethane

Review of bioremediation approaches indicates that 1,1,2-TCA is subject to anaerobic biodegradation (Ferguson and Pietari 2000, Lorah and Voytek 2004) but does not degrade readily under aerobic conditions (HSDB and ATSDR 1989).

References

Anaerobic Transformations and Bioremediation of Chlorinated Solvents
Ferguson, J. and J.M.H. Pietari.
Environmental Pollution 107(2):209-215(2000)

The anaerobic degradation of TeCA provides examples of reductive dechlorination, dehydrochlorination and dichloroelemination. A lab study using anaerobic sludge that had been fed chlorinated compounds showed that TeCA was transformed to four products and that these were further transformed, suggesting that it might be possible to degrade TeCA to innocuous products. 1,1,2-TCA was one of the degradation products. View abstract

Degradation of 1,1,2,2-Tetrachloroethane and Accumulation of Vinyl Chloride in Wetland Sediment Microcosms and In Situ Porewater: Biogeochemical Controls and Associations with Microbial Communities
Lorah, M.M. and M.A. Voytek.
Journal of Contaminant Hydrology 70(1-2):117-145(2004)

This paper investigates the degradation of TeCA and 1,1,2-TCA under different anaerobic conditions. View abstract

Toxicological Profile for 1,1,2-Trichloroethane
Agency for Toxic Substances and Disease Registry (ATSDR), 120 pp, 1989

1,1,2,2- Tetrachloroethane

Review of bioremediation approaches indicates that 1,1,2,2-TetCA can be degraded under anaerobic conditions; however, without a suitable mix of microbes, vinyl chloride will accumulate (Jones et al. 2006, ATSDR 2008). The compound might degrade under aerobic conditions, but the evidence is mixed (ATSDR 2008).

References

Characterization of a Microbial Consortium Capable of Rapid and Simultaneous Dechlorination of 1,1,2,2-Tetrachloroethane and Chlorinated Ethane and Ethene Intermediates
Jones, E., M. Voytek, M. Lorah, and J. Kirshtein.
Bioremediation Journal 10(4):153-168(2006)
View abstract Description of WBC-2 Culture

Toxicological Profile for 1,1,2,2-Tetrachloroethane
Agency for Toxic Substances and Disease Registry (ATSDR),258 pp, 2008

1,1,2-Trichlorotrifluoroethane

Review of bioremediation approaches indicates that under anaerobic conditions, TCTFE is readily degraded by microbial action to chlorotrifluoroethene, a vinyl chloride analog (van Agteren et al. 1998, Bagley et al. 2004, HSDB); however, the compound does not degrade readily under aerobic conditions (HSDB, Reinhard and McCarty 1993). Cometabolic degradation of TCTFE to various lower halogenated compounds by Pseudomonas putida under anaerobic conditions has been observed (van Agteren et al. 1998).

References

Handbook on Biodegradation and Biological Treatment of Hazardous Organic Compounds
van Agteren, M., S. Keuning, and D. Janssen.
Springer, 504 pp, 1998

1,1,2-Trichloro-1,2,2-Trifluoroethane (76-13-1)
Hazardous Substances Data Bank (HSDB)
TOXNET, National Library of Medicine Web site.

Non-Enzymatic Degradation of Chlorofluorocarbon 113 Using Cyanocobalamin under Anaerobic Conditions
Bagley, D., I. Sutherland, and B. Sleep.
Journal of Environmental Engineering & Science 3(4):295-299(2004)

Freon 113 was degraded rapidly and completely in systems containing cyanocobalamin with titanium(III) citrate as the reductant. 1,2-Dichloro-1,1,2-trifluoroethane accounted for up to 25% of the degraded Freon 113. Chlorotrifluoroethene was also detected. View longer abstract

Long-term Chemical Transformation of 1,1,1-Trichloroethane (TCA) and Freon 113 under Aquifer Conditions
Reinhard, M. and P. McCarty.
U.S. EPA, National Center For Environmental Research, Grant R825689C044, Subproject 44, 1993. View project summary

1,2-Dibromo-3-chloropropane

Review of bioremediation approaches indicates that DBCP can be degraded under anaerobic conditions (methanogenesis, denitrification, and sulfate respiration) (Howard 1991), but the compound does not degrade readily under naturally found aerobic conditions (ATSDR 1992 and Williams et al. 1989).

References

Biodegradation of DIMP, Dieldrin, Isodrin, DBCP, and PCPMSO in Rocky Mountain Arsenal SoilsAdobe PDF Logo
Williams, R.T., P.S. Ziegenfuss, and P.J. Marks.
U.S. Army Toxic and Hazardous Materials Agency, CETHA-TE-CR-007, 92 pp, 1989

This laboratory study found that DBCP undergoes minimal aerobic biodegradation and is expected to persist in aerobic soils.

Handbook of Environmental Fate and Exposure Data for Organic Chemicals, Volume III: Pesticides
Howard, P., ed.
Lewis Publishers, 684 pp, 1991

Toxicological Profile for 1,2-Dibromo-3-Chloropropane
Agency for Toxic Substances and Disease Registry (ATSDR), 164 pp, 1992

1,2-Dichloropropane

Review of bioremediation approaches indicates that 1,2-DCP can be degraded under anaerobic conditions (Ritalaht 2004), but the compound is very recalcitrant to aerobic biodegradation (Haggbloom 2003 and Ritalaht 2004).

References

Dehalogenation: Microbial Processes and Environmental Applications
Haggblom, M.M. and I.D. Bossert.
Kluwer Academic Publishers, ISBN: 1402074069, 520 pp, 2003

Populations Implicated in Anaerobic Reductive Dechlorination of 1,2-Dichloropropane in Highly Enriched Bacterial Communities
Ritalahti, K. and Frank E. Loeffler.
Applied and Environmental Microbiology 70(7):4088-4095(2004)
View abstract