Biotic and Abiotic Dehalogenation of 1,1,2-Trichloro-1,2,2-trifluoroethane (CFC-113): Implications for Bacterial Detoxification of Chlorinated Ethenes

Im, Jeongdae; Mack, E. Erin; Seger, Edward S.; Löffler, Frank E.

doi:10.1021/acs.est.9b04399

Biotic and Abiotic Dehalogenation of 1,1,2-Trichloro-1,2,2-trifluoroethane (CFC-113): Implications for Bacterial Detoxification of Chlorinated Ethenes

Journal Article · Tue Sep 17 00:00:00 EDT 2019 · Environmental Science and Technology

DOI:https://doi.org/10.1021/acs.est.9b04399· OSTI ID:1819522

^[1]; Mack, E. Erin ^[2]; Seger, Edward S. ^[3]; ^[4]

Kansas State Univ., Manhattan, KS (United States)
Corteva Agriscience, Wilmington, DE (United States)
The Chemours Company, Wilmington, DE (United States)
Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Chlorofluorocarbons including 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) often occur in groundwater plumes comingled with chlorinated solvents such as trichloroethene (TCE). We show that CFC-113 inhibits reductive dechlorination by Dehalococcoides mccartyi (Dhc) in a concentration-dependent manner, causing cis-1,2-dichloroethene (cis-DCE) stalls. Following a 17-day exposure of Dhc-containing consortium SDC-9 to 76 μM CFC-113, cis-DCE dechlorination activity did not recover after CFC-113 removal. River sediment microcosms demonstrated that CFC-113 was subject to microbial degradation under anoxic conditions, and chlorotrifluoroethene (CTFE) was observed as a transformation product. No degradation of CFC-113 was observed in killed controls and in incubations with reactive minerals including mackinawite, green rust, magnetite, and manganese dioxide. In vitro experiments with reduced corrinoid (i.e., vitamin B₁₂) mediated reductive dechlorination of CFC-113 to CTFE and trifluoroethene (TFE) followed by reductive defluorination of TFE to cis-1,2-difluoroethene (cis-DFE) as an end product. This biomimetic degradation of CFC-113 to cis-DFE was also demonstrated in vivo using the corrinoid-producing homoacetogen Sporomusa ovata, suggesting the cometabolic microbial reductive dechlorination and reductive defluorination of CFC-113 to cis-DFE is feasible under anoxic in situ conditions. The CFC-113 degradation intermediates CTFE, TFE, and cis-DFE did not inhibit TCE dechlorination by Dhc, indicating that the initial reductive transformation step can overcome cis-DCE stalls.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE; USDOD; Kansas State University

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1819522

Journal Information:: Environmental Science and Technology, Journal Name: Environmental Science and Technology Journal Issue: 20 Vol. 53; ISSN 0013-936X

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (47)

Kinetics of tetrachloroethylene-reductive dechlorination catalyzed by vitamin B ₁₂ Burris, David R.; Delcomyn, Carrie A.; Deng, Baolin Environmental Toxicology and Chemistry, Vol. 17, Issue 9 https://doi.org/10.1002/etc.5620170906	journal	September 1998
An evaluation of permeable reactive barrier projects in California: An Evaluation of Permeable Reactive Barrier Projects in California Muegge, John P.; Hadley, Paul W. Remediation Journal, Vol. 20, Issue 1 https://doi.org/10.1002/rem.20228	journal	December 2009
Dehalococcoides and Reductive Dechlorination of Chlorinated Solvents Löffler, Frank E.; Ritalahti, Kirsti M.; Zinder, Stephen H. Bioaugmentation for Groundwater Remediation https://doi.org/10.1007/978-1-4614-4115-1_2	book	July 2012
Biosynthesis of para-cresolyl cobamide in Sporomusa ovata Stupperich, Erhard; Eisinger, Hans J�rgen Archives of Microbiology, Vol. 151, Issue 4 https://doi.org/10.1007/bf00406567	journal	March 1989
Reductive dechlorination of tetrachloroethylene (PCE) catalyzed by cyanocobalamin Habeck, Brian D.; Sublette, Kerry L. Applied Biochemistry and Biotechnology, Vol. 51-52, Issue 1 https://doi.org/10.1007/bf02933475	journal	September 1995
Biological degradation of VCCs and CFCs under simulated anaerobic landfill conditions in laboratory test digesters Deipser, Anna; Stegmann, Rainer Environmental Science and Pollution Research, Vol. 4, Issue 4 https://doi.org/10.1007/bf02986348	journal	December 1997
Degradation of chlorofluorocarbon-113 under anaerobic conditions Lesage, Suzanne; Brown, Susan; Hosler, Kevin R. Chemosphere, Vol. 24, Issue 9 https://doi.org/10.1016/0045-6535(92)90049-w	journal	May 1992
Reductive dechlorination of chlorofluorocarbons and hydrochlorofluorocarbons in sewage sludge and aquifer sediment microcosms Balsiger, Christian; Holliger, Christof; Höhener, Patrick Chemosphere, Vol. 61, Issue 3 https://doi.org/10.1016/j.chemosphere.2005.02.087	journal	October 2005
Changes in the levels and variability of halocarbons and the compliance with the Montreal Protocol from an urban view Ou-Yang, Chang-Feng; Chang, Chih-Chung; Chen, Shen-Po Chemosphere, Vol. 138 https://doi.org/10.1016/j.chemosphere.2015.06.070	journal	November 2015
Harnessing microbial activities for environmental cleanup Löffler, Frank E.; Edwards, Elizabeth A. Current Opinion in Biotechnology, Vol. 17, Issue 3 https://doi.org/10.1016/j.copbio.2006.05.001	journal	June 2006
Aerobic biotransformation of N-nitrosodimethylamine and N-nitrodimethylamine in methane and benzene amended soil columns Weidhaas, Jennifer; Dupont, R. Ryan Journal of Contaminant Hydrology, Vol. 150 https://doi.org/10.1016/j.jconhyd.2013.04.004	journal	July 2013
Degradation of chlorofluorocarbons using granular iron and bimetallic irons Jeen, Sung-Wook; Lazar, Snezana; Gui, Lai Journal of Contaminant Hydrology, Vol. 158 https://doi.org/10.1016/j.jconhyd.2014.01.002	journal	March 2014
Prediction of future disposal of end-of-life refrigerators containing CFC-11 Yazici, Burcu; Can, Zehra S.; Calli, Baris Waste Management, Vol. 34, Issue 1 https://doi.org/10.1016/j.wasman.2013.09.008	journal	January 2014
Enrichment, Cultivation, and Detection of Reductively Dechlorinating Bacteria Löffler, Frank E.; Sanford, Robert A.; Ritalahti, Kirsti M. Methods in Enzymology https://doi.org/10.1016/s0076-6879(05)97005-5	book	January 2005
Experimental Comparison of the Different Approaches To Estimate LOD and LOQ of an HPLC Method Vial, Jérôme; Jardy, Alain Analytical Chemistry, Vol. 71, Issue 14 https://doi.org/10.1021/ac981179n	journal	July 1999
Compound-Specific Stable Carbon Isotope Analysis of Chlorofluorocarbons in Groundwater Horst, Axel; Lacrampe-Couloume, Georges; Sherwood Lollar, Barbara Analytical Chemistry, Vol. 87, Issue 20 https://doi.org/10.1021/acs.analchem.5b02701	journal	October 2015
Effects of Aqueous Film-Forming Foams (AFFFs) on Trichloroethene (TCE) Dechlorination by a Dehalococcoides mccartyi -Containing Microbial Community Harding-Marjanovic, Katie C.; Yi, Shan; Weathers, Tess S. Environmental Science & Technology, Vol. 50, Issue 7 https://doi.org/10.1021/acs.est.5b04773	journal	March 2016
Perfluoroalkyl Acids Inhibit Reductive Dechlorination of Trichloroethene by Repressing Dehalococcoides Weathers, Tess S.; Harding-Marjanovic, Katie; Higgins, Christopher P. Environmental Science & Technology, Vol. 50, Issue 1 https://doi.org/10.1021/acs.est.5b04854	journal	December 2015
Reductive formation of carbon monoxide from carbon tetrachloride and FREONS 11, 12, and 13 catalyzed by corrinoids Krone, Ute E.; Thauer, Rudolf K.; Hogenkamp, Harry P. C. Biochemistry, Vol. 30, Issue 10 https://doi.org/10.1021/bi00224a020	journal	March 1991
Coenzyme F430 as a possible catalyst for the reductive dehalogenation of chlorinated C1 hydrocarbons in methanogenic bacteria Krone, Ute E.; Laufer, Kerstin; Thauer, Rudolf K. Biochemistry, Vol. 28, Issue 26 https://doi.org/10.1021/bi00452a027	journal	December 1989
Occurrence and fate of organic solvent residues in anoxic groundwater at the Gloucester landfill, Canada Lesage, Suzanne; Jackson, Richard E.; Priddle, Mark W. Environmental Science & Technology, Vol. 24, Issue 4 https://doi.org/10.1021/es00074a016	journal	April 1990
Field Demonstration of Successful Bioaugmentation To Achieve Dechlorination of Tetrachloroethene To Ethene Major, David W.; McMaster, Michaye L.; Cox, Evan E. Environmental Science & Technology, Vol. 36, Issue 23 https://doi.org/10.1021/es0255711	journal	December 2002
Abiotic Reductive Dechlorination of Chlorinated Ethylenes by Iron-Bearing Soil Minerals. 1. Pyrite and Magnetite Lee, Woojin; Batchelor, Bill Environmental Science & Technology, Vol. 36, Issue 23 https://doi.org/10.1021/es025836b	journal	December 2002
Abiotic Reductive Dechlorination of Chlorinated Ethylenes by Iron-Bearing Soil Minerals. 2. Green Rust Lee, Woojin; Batchelor, Bill Environmental Science & Technology, Vol. 36, Issue 24 https://doi.org/10.1021/es0258374	journal	December 2002
Bioreactive Barriers: A Comparison of Bioaugmentation and Biostimulation for Chlorinated Solvent Remediation Lendvay, J. M.; Löffler, F. E.; Dollhopf, M. Environmental Science & Technology, Vol. 37, Issue 7 https://doi.org/10.1021/es025985u	journal	April 2003
Effects of Ag ^I , Au ^III , and Cu ^II on the Reductive Dechlorination of Carbon Tetrachloride by Green Rust O'Loughlin, Edward J.; Kemner, Kenneth M.; Burris, David R. Environmental Science & Technology, Vol. 37, Issue 13 https://doi.org/10.1021/es030304w	journal	July 2003
Nonbiological Removal of cis -Dichloroethylene and 1,1-Dichloroethylene in Aquifer Sediment Containing Magnetite Ferrey, Mark L.; Wilkin, Richard T.; Ford, Robert G. Environmental Science & Technology, Vol. 38, Issue 6 https://doi.org/10.1021/es0305609	journal	March 2004
Reductive Dechlorination of Tetrachloroethylene and Trichloroethylene by Mackinawite (FeS) in the Presence of Metals: Reaction Rates Jeong, Hoon Y.; Hayes, Kim F. Environmental Science & Technology, Vol. 41, Issue 18 https://doi.org/10.1021/es0706394	journal	September 2007
Quantifying the Effects of 1,1,1-Trichloroethane and 1,1-Dichloroethane on Chlorinated Ethene Reductive Dehalogenases Chan, Winnie W. M.; Grostern, Ariel; Löffler, Frank E. Environmental Science & Technology, Vol. 45, Issue 22 https://doi.org/10.1021/es201260n	journal	November 2011
Carbon Isotopic Fractionation of CFCs during Abiotic and Biotic Degradation Archbold, Marie E.; Elliot, Trevor; Kalin, Robert M. Environmental Science & Technology, Vol. 46, Issue 3 https://doi.org/10.1021/es203386a	journal	January 2012
Environmental Fate of the Next Generation Refrigerant 2,3,3,3-Tetrafluoropropene (HFO-1234yf) Im, Jeongdae; Walshe-Langford, Gillian E.; Moon, Ji-Won Environmental Science & Technology, Vol. 48, Issue 22 https://doi.org/10.1021/es5032147	journal	October 2014
Reductive Defluorination of Perfluorooctane Sulfonate Ochoa-Herrera, Valeria; Sierra-Alvarez, Reyes; Somogyi, Arpad Environmental Science & Technology, Vol. 42, Issue 9 https://doi.org/10.1021/es702842q	journal	May 2008
Reaction of Tetrabromobisphenol A (TBBPA) with Manganese Dioxide: Kinetics, Products, and Pathways Lin, Kunde; Liu, Weiping; Gan, Jay Environmental Science & Technology, Vol. 43, Issue 12 https://doi.org/10.1021/es803622t	journal	June 2009
Reductive Elimination of Chlorinated Ethylenes by Zero-Valent Metals Roberts, A. Lynn; Totten, Lisa A.; Arnold, William A. Environmental Science & Technology, Vol. 30, Issue 8 https://doi.org/10.1021/es9509644	journal	January 1996
Reductive Dechlorination of Tetrachloroethylene and Trichloroethylene Catalyzed by Vitamin B ₁₂ in Homogeneous and Heterogeneous Systems Burris, David R.; Delcomyn, Carrie A.; Smith, Mark H. Environmental Science & Technology, Vol. 30, Issue 10 https://doi.org/10.1021/es960116o	journal	January 1996
Kinetics of the Transformation of Trichloroethylene and Tetrachloroethylene by Iron Sulfide Butler, Elizabeth C.; Hayes, Kim F. Environmental Science & Technology, Vol. 33, Issue 12 https://doi.org/10.1021/es9809455	journal	June 1999
Investigation of the Long-Term Performance of Zero-Valent Iron for Reductive Dechlorination of Trichloroethylene Farrell, James; Kason, Mark; Melitas, Nicos Environmental Science & Technology, Vol. 34, Issue 3 https://doi.org/10.1021/es990716y	journal	February 2000
Grape pomace compost harbors organohalide-respiring Dehalogenimonas species with novel reductive dehalogenase genes Yang, Yi; Higgins, Steven A.; Yan, Jun The ISME Journal, Vol. 11, Issue 12 https://doi.org/10.1038/ismej.2017.127	journal	August 2017
Detoxification of vinyl chloride to ethene coupled to growth of an anaerobic bacterium He, Jianzhong; Ritalahti, Kirsti M.; Yang, Kun-Lin Nature, Vol. 424, Issue 6944 https://doi.org/10.1038/nature01717	journal	July 2003
Worldwide Occurrence and Fate of Chlorofluorocarbons in Groundwater Höhener, Patrick; Werner, David; Balsiger, Christian Critical Reviews in Environmental Science and Technology, Vol. 33, Issue 1 https://doi.org/10.1080/10643380390814433	journal	January 2003
Resilience and recovery of Dehalococcoides mccartyi following low pH exposure Yang, Yi; Cápiro, Natalie L.; Yan, Jun FEMS Microbiology Ecology, Vol. 93, Issue 12 https://doi.org/10.1093/femsec/fix130	journal	October 2017
Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity Yan, Jun; Im, Jeongdae; Yang, Yi Philosophical Transactions of the Royal Society B: Biological Sciences, Vol. 368, Issue 1616 https://doi.org/10.1098/rstb.2012.0320	journal	April 2013
Dehalogenimonas lykanthroporepellens gen. nov., sp. nov., a reductively dehalogenating bacterium isolated from chlorinated solvent-contaminated groundwater Moe, W. M.; Yan, J.; Nobre, M. F. INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY, Vol. 59, Issue 11 https://doi.org/10.1099/ijs.0.011502-0	journal	July 2009
Chlorinated Decreasing Solvents: Physical-Chemical Properties Affecting Aquifer Contamination and Remediation Jackson, Richard E.; Dwarakanath, Varadarajan Groundwater Monitoring & Remediation, Vol. 19, Issue 4 https://doi.org/10.1111/j.1745-6592.1999.tb00246.x	journal	November 1999
Vitamin B ₁₂ and Reduced Titanium for Remediation of Residual Chlorinated Solvents: Field Experiment Sorel, Dominique; Lesage, Suzanne; Brown, Susan Groundwater Monitoring & Remediation, Vol. 21, Issue 4 https://doi.org/10.1111/j.1745-6592.2001.tb00650.x	journal	November 2001
Reductive Dehalogenase Gene Expression as a Biomarker for Physiological Activity of Dehalococcoides spp. Lee, P. K. H.; Johnson, D. R.; Holmes, V. F. Applied and Environmental Microbiology, Vol. 72, Issue 9 https://doi.org/10.1128/aem.01070-06	journal	September 2006
Complete reductive dechlorination of 1,2-dichloropropane by anaerobic bacteria Loffler, F. E.; Champine, J. E.; Ritalahti, K. M. Applied and Environmental Microbiology, Vol. 63, Issue 7 https://doi.org/10.1128/aem.63.7.2870-2875.1997	journal	July 1997

Similar Records

Palladium-assisted electrodehalogenation of 1,1,2-trichloro-1,2,2-trifluoroethane on lead cathodes combined with hydrogen diffusion anodes

Journal Article · Fri Oct 31 23:00:00 EST 1997 · Journal of the Electrochemical Society · OSTI ID:564077

Extraction of degradation rate constants from the St. Joseph, Michigan trichloroethene site

Technical Report · Mon Dec 30 23:00:00 EST 1996 · OSTI ID:422177

Reductive dechlorination of chlorinated ethenes and 1,2-dichloroethane by Dehalococcoides ethenogenes'' 195

Journal Article · Thu Jul 01 00:00:00 EDT 1999 · Applied and Environmental Microbiology · OSTI ID:6428952

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Degradation
Minerals
Nutrition
Organic compounds
Reductive dechlorination

Biotic and Abiotic Dehalogenation of 1,1,2-Trichloro-1,2,2-trifluoroethane (CFC-113): Implications for Bacterial Detoxification of Chlorinated Ethenes

Citation Formats

References (47)

Similar Records

Related Subjects