Use of Halogenated Benzoates and Other Halogenated Aromatic Compounds To Stimulate the Microbial Dechlorination of PCBs
We recently reported that certain polychlorinated biphenyl (PCB) congeners and bromobiphenyl congeners activate or “prime” dechlorination of the Aroclor 1260 in Housatonic River sediments. In this study, we tested the ability of halogenated benzoates and other halogenated aromatic compounds to prime...
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description | We recently reported that certain polychlorinated biphenyl (PCB) congeners and bromobiphenyl congeners activate or “prime” dechlorination of the Aroclor 1260 in Housatonic River sediments. In this study, we tested the ability of halogenated benzoates and other halogenated aromatic compounds to prime PCB dechlorination in the same sediments. We found that none of the fluorinated or chlorinated benzoates primed PCB dechlorination, but several brominated and iodinated benzoates initiated this activity. Of the halogenated benzoates tested, 4-bromobenzoate, 4-iodobenzoate, and 2,5-dibromobenzoate primed the most extensive PCB dechlorination, decreasing the hexa- through nonachlorobiphenyl fraction of Aroclor 1260 by 40−70%, 10−50%, and 10−50%, respectively. None of the halogenated benzoates were as effective at priming PCB dechlorination as 2,6-dibromobiphenyl, which primed a 60−80% decrease of the hexa- through nonachlorobiphenyl fraction of Aroclor 1260. Several other brominated aromatic compounds were also tested for their ability to prime PCB dechlorination. Monobrominated isomers of acetophenone, phenol, or toluene did not prime PCB dechlorination, but all monobrominated isomers of benzonitrile, 2-bromo-, 4-bromo-, and 2,5-dibromonitrobenzene, 4-bromobenzamide, 4-bromobenzophenone, 4-bromobenzoic hydrazide, 4-bromobenzoic methyl ester, and 2,5-dibromobenzene sulfonate primed PCB dechlorination in Housatonic River sediments. All of the compounds primed PCB Dechlorination Process N (primarily flanked meta dechlorination) except 4-bromonitrobenzene, which primed Dechlorination Process P (flanked para dechlorination). These results indicate that halogenated aromatic compounds that are not structural analogues to PCBs can prime PCB dechlorination. |
doi_str_mv | 10.1021/es9812498 |
format | Article |
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In this study, we tested the ability of halogenated benzoates and other halogenated aromatic compounds to prime PCB dechlorination in the same sediments. We found that none of the fluorinated or chlorinated benzoates primed PCB dechlorination, but several brominated and iodinated benzoates initiated this activity. Of the halogenated benzoates tested, 4-bromobenzoate, 4-iodobenzoate, and 2,5-dibromobenzoate primed the most extensive PCB dechlorination, decreasing the hexa- through nonachlorobiphenyl fraction of Aroclor 1260 by 40−70%, 10−50%, and 10−50%, respectively. None of the halogenated benzoates were as effective at priming PCB dechlorination as 2,6-dibromobiphenyl, which primed a 60−80% decrease of the hexa- through nonachlorobiphenyl fraction of Aroclor 1260. Several other brominated aromatic compounds were also tested for their ability to prime PCB dechlorination. Monobrominated isomers of acetophenone, phenol, or toluene did not prime PCB dechlorination, but all monobrominated isomers of benzonitrile, 2-bromo-, 4-bromo-, and 2,5-dibromonitrobenzene, 4-bromobenzamide, 4-bromobenzophenone, 4-bromobenzoic hydrazide, 4-bromobenzoic methyl ester, and 2,5-dibromobenzene sulfonate primed PCB dechlorination in Housatonic River sediments. All of the compounds primed PCB Dechlorination Process N (primarily flanked meta dechlorination) except 4-bromonitrobenzene, which primed Dechlorination Process P (flanked para dechlorination). These results indicate that halogenated aromatic compounds that are not structural analogues to PCBs can prime PCB dechlorination.</description><identifier>ISSN: 0013-936X</identifier><identifier>EISSN: 1520-5851</identifier><identifier>DOI: 10.1021/es9812498</identifier><identifier>CODEN: ESTHAG</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>540320 - Environment, Aquatic- Chemicals Monitoring & Transport- (1990-) ; Applied sciences ; Aroclor 1260 ; AROMATICS ; benzoate ; BENZOIC ACID ; BIODEGRADATION ; Biodegradation of pollutants ; Biological and medical sciences ; Biotechnology ; CARBOXYLIC ACIDS ; CHEMICAL REACTIONS ; Chemistry ; CHLORINATED AROMATIC HYDROCARBONS ; DECHLORINATION ; DECOMPOSITION ; Decontamination. Miscellaneous ; DEHALOGENATION ; Earth sciences ; Earth, ocean, space ; Engineering and environment geology. Geothermics ; Environment and pollution ; ENVIRONMENTAL SCIENCES ; Exact sciences and technology ; Freshwater ; Fundamental and applied biological sciences. Psychology ; HALOGENATED AROMATIC HYDROCARBONS ; Industrial applications and implications. Economical aspects ; MONOCARBOXYLIC ACIDS ; ORGANIC ACIDS ; ORGANIC CHLORINE COMPOUNDS ; ORGANIC COMPOUNDS ; ORGANIC HALOGEN COMPOUNDS ; PCB ; POLLUTION ; Pollution, environment geology ; POLYCHLORINATED BIPHENYLS ; REMEDIAL ACTION ; Soil and sediments pollution ; USA, Housatonic R ; USA, New York, Housatonic R ; WATER POLLUTION</subject><ispartof>Environmental science & technology, 1999-06, Vol.33 (12), p.2057-2063</ispartof><rights>Copyright © 1999 American Chemical Society</rights><rights>1999 INIST-CNRS</rights><rights>Copyright American Chemical Society Jun 15, 1999</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a535t-3e6447ad57ca30f9950185e804b59993a2350e748c5bcff4ea249e57931d654b3</citedby><cites>FETCH-LOGICAL-a535t-3e6447ad57ca30f9950185e804b59993a2350e748c5bcff4ea249e57931d654b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/es9812498$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/es9812498$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1855440$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/6481559$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>DeWeerd, Kim A</creatorcontrib><creatorcontrib>Bedard, Donna L</creatorcontrib><title>Use of Halogenated Benzoates and Other Halogenated Aromatic Compounds To Stimulate the Microbial Dechlorination of PCBs</title><title>Environmental science & technology</title><addtitle>Environ. Sci. Technol</addtitle><description>We recently reported that certain polychlorinated biphenyl (PCB) congeners and bromobiphenyl congeners activate or “prime” dechlorination of the Aroclor 1260 in Housatonic River sediments. In this study, we tested the ability of halogenated benzoates and other halogenated aromatic compounds to prime PCB dechlorination in the same sediments. We found that none of the fluorinated or chlorinated benzoates primed PCB dechlorination, but several brominated and iodinated benzoates initiated this activity. Of the halogenated benzoates tested, 4-bromobenzoate, 4-iodobenzoate, and 2,5-dibromobenzoate primed the most extensive PCB dechlorination, decreasing the hexa- through nonachlorobiphenyl fraction of Aroclor 1260 by 40−70%, 10−50%, and 10−50%, respectively. None of the halogenated benzoates were as effective at priming PCB dechlorination as 2,6-dibromobiphenyl, which primed a 60−80% decrease of the hexa- through nonachlorobiphenyl fraction of Aroclor 1260. Several other brominated aromatic compounds were also tested for their ability to prime PCB dechlorination. Monobrominated isomers of acetophenone, phenol, or toluene did not prime PCB dechlorination, but all monobrominated isomers of benzonitrile, 2-bromo-, 4-bromo-, and 2,5-dibromonitrobenzene, 4-bromobenzamide, 4-bromobenzophenone, 4-bromobenzoic hydrazide, 4-bromobenzoic methyl ester, and 2,5-dibromobenzene sulfonate primed PCB dechlorination in Housatonic River sediments. All of the compounds primed PCB Dechlorination Process N (primarily flanked meta dechlorination) except 4-bromonitrobenzene, which primed Dechlorination Process P (flanked para dechlorination). These results indicate that halogenated aromatic compounds that are not structural analogues to PCBs can prime PCB dechlorination.</description><subject>540320 - Environment, Aquatic- Chemicals Monitoring & Transport- (1990-)</subject><subject>Applied sciences</subject><subject>Aroclor 1260</subject><subject>AROMATICS</subject><subject>benzoate</subject><subject>BENZOIC ACID</subject><subject>BIODEGRADATION</subject><subject>Biodegradation of pollutants</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>CARBOXYLIC ACIDS</subject><subject>CHEMICAL REACTIONS</subject><subject>Chemistry</subject><subject>CHLORINATED AROMATIC HYDROCARBONS</subject><subject>DECHLORINATION</subject><subject>DECOMPOSITION</subject><subject>Decontamination. Miscellaneous</subject><subject>DEHALOGENATION</subject><subject>Earth sciences</subject><subject>Earth, ocean, space</subject><subject>Engineering and environment geology. Geothermics</subject><subject>Environment and pollution</subject><subject>ENVIRONMENTAL SCIENCES</subject><subject>Exact sciences and technology</subject><subject>Freshwater</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HALOGENATED AROMATIC HYDROCARBONS</subject><subject>Industrial applications and implications. Economical aspects</subject><subject>MONOCARBOXYLIC ACIDS</subject><subject>ORGANIC ACIDS</subject><subject>ORGANIC CHLORINE COMPOUNDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC HALOGEN COMPOUNDS</subject><subject>PCB</subject><subject>POLLUTION</subject><subject>Pollution, environment geology</subject><subject>POLYCHLORINATED BIPHENYLS</subject><subject>REMEDIAL ACTION</subject><subject>Soil and sediments pollution</subject><subject>USA, Housatonic R</subject><subject>USA, New York, Housatonic R</subject><subject>WATER POLLUTION</subject><issn>0013-936X</issn><issn>1520-5851</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNplkU9v1DAQxSMEEkvhwDewECBxCNixncTHdhdapFZdqVtpb5bXmVCXxF48jvjz6XGValeIky3N7715M1MUrxn9yGjFPgGqllVCtU-KBZMVLWUr2dNiQSnjpeL19nnxAvGeUlpx2i6Kn7cIJPTkwgzhG3iToCNn4P-E_ENifEeu0x3Ef-qnMYwmOUuWYdyHyXdINoHcJDdOQwZIFpArZ2PYOTOQFdi7IUSXtS74h17r5Rm-LJ71ZkB49fieFLdfPm-WF-Xl9fnX5ellaSSXqeRQC9GYTjbWcNorJSlrJbRU7KRSipuKSwqNaK3c2b4XYPLsIBvFWVdLseMnxZvZN2ByGq1LOY4N3oNNuhYtk1Jl6P0M7WP4MQEmPTq0MAzGQ5hQs4Y3NPc8uh3A-zBFnwfQeZ2sqlXTZOjDDOUNIEbo9T660cTfmlH9cCR9OFJm3z4aGrRm6KPx1uFR0EopBM1YOWMOE_w6lE38ruucTerN-kZvV_Rqvdqe6zrz72beWDxG_L_9X6coqpM</recordid><startdate>19990615</startdate><enddate>19990615</enddate><creator>DeWeerd, Kim A</creator><creator>Bedard, Donna L</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7ST</scope><scope>7T7</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>SOI</scope><scope>7TV</scope><scope>7UA</scope><scope>F1W</scope><scope>H97</scope><scope>L.G</scope><scope>OTOTI</scope></search><sort><creationdate>19990615</creationdate><title>Use of Halogenated Benzoates and Other Halogenated Aromatic Compounds To Stimulate the Microbial Dechlorination of PCBs</title><author>DeWeerd, Kim A ; Bedard, Donna L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a535t-3e6447ad57ca30f9950185e804b59993a2350e748c5bcff4ea249e57931d654b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>540320 - Environment, Aquatic- Chemicals Monitoring & Transport- (1990-)</topic><topic>Applied sciences</topic><topic>Aroclor 1260</topic><topic>AROMATICS</topic><topic>benzoate</topic><topic>BENZOIC ACID</topic><topic>BIODEGRADATION</topic><topic>Biodegradation of pollutants</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>CARBOXYLIC ACIDS</topic><topic>CHEMICAL REACTIONS</topic><topic>Chemistry</topic><topic>CHLORINATED AROMATIC HYDROCARBONS</topic><topic>DECHLORINATION</topic><topic>DECOMPOSITION</topic><topic>Decontamination. 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Economical aspects</topic><topic>MONOCARBOXYLIC ACIDS</topic><topic>ORGANIC ACIDS</topic><topic>ORGANIC CHLORINE COMPOUNDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC HALOGEN COMPOUNDS</topic><topic>PCB</topic><topic>POLLUTION</topic><topic>Pollution, environment geology</topic><topic>POLYCHLORINATED BIPHENYLS</topic><topic>REMEDIAL ACTION</topic><topic>Soil and sediments pollution</topic><topic>USA, Housatonic R</topic><topic>USA, New York, Housatonic R</topic><topic>WATER POLLUTION</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>DeWeerd, Kim A</creatorcontrib><creatorcontrib>Bedard, Donna L</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><collection>Pollution Abstracts</collection><collection>Water Resources Abstracts</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>OSTI.GOV</collection><jtitle>Environmental science & technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>DeWeerd, Kim A</au><au>Bedard, Donna L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Use of Halogenated Benzoates and Other Halogenated Aromatic Compounds To Stimulate the Microbial Dechlorination of PCBs</atitle><jtitle>Environmental science & technology</jtitle><addtitle>Environ. Sci. Technol</addtitle><date>1999-06-15</date><risdate>1999</risdate><volume>33</volume><issue>12</issue><spage>2057</spage><epage>2063</epage><pages>2057-2063</pages><issn>0013-936X</issn><eissn>1520-5851</eissn><coden>ESTHAG</coden><abstract>We recently reported that certain polychlorinated biphenyl (PCB) congeners and bromobiphenyl congeners activate or “prime” dechlorination of the Aroclor 1260 in Housatonic River sediments. In this study, we tested the ability of halogenated benzoates and other halogenated aromatic compounds to prime PCB dechlorination in the same sediments. We found that none of the fluorinated or chlorinated benzoates primed PCB dechlorination, but several brominated and iodinated benzoates initiated this activity. Of the halogenated benzoates tested, 4-bromobenzoate, 4-iodobenzoate, and 2,5-dibromobenzoate primed the most extensive PCB dechlorination, decreasing the hexa- through nonachlorobiphenyl fraction of Aroclor 1260 by 40−70%, 10−50%, and 10−50%, respectively. None of the halogenated benzoates were as effective at priming PCB dechlorination as 2,6-dibromobiphenyl, which primed a 60−80% decrease of the hexa- through nonachlorobiphenyl fraction of Aroclor 1260. Several other brominated aromatic compounds were also tested for their ability to prime PCB dechlorination. Monobrominated isomers of acetophenone, phenol, or toluene did not prime PCB dechlorination, but all monobrominated isomers of benzonitrile, 2-bromo-, 4-bromo-, and 2,5-dibromonitrobenzene, 4-bromobenzamide, 4-bromobenzophenone, 4-bromobenzoic hydrazide, 4-bromobenzoic methyl ester, and 2,5-dibromobenzene sulfonate primed PCB dechlorination in Housatonic River sediments. All of the compounds primed PCB Dechlorination Process N (primarily flanked meta dechlorination) except 4-bromonitrobenzene, which primed Dechlorination Process P (flanked para dechlorination). These results indicate that halogenated aromatic compounds that are not structural analogues to PCBs can prime PCB dechlorination.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/es9812498</doi><tpages>7</tpages></addata></record> |
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subjects | 540320 - Environment, Aquatic- Chemicals Monitoring & Transport- (1990-) Applied sciences Aroclor 1260 AROMATICS benzoate BENZOIC ACID BIODEGRADATION Biodegradation of pollutants Biological and medical sciences Biotechnology CARBOXYLIC ACIDS CHEMICAL REACTIONS Chemistry CHLORINATED AROMATIC HYDROCARBONS DECHLORINATION DECOMPOSITION Decontamination. Miscellaneous DEHALOGENATION Earth sciences Earth, ocean, space Engineering and environment geology. Geothermics Environment and pollution ENVIRONMENTAL SCIENCES Exact sciences and technology Freshwater Fundamental and applied biological sciences. Psychology HALOGENATED AROMATIC HYDROCARBONS Industrial applications and implications. Economical aspects MONOCARBOXYLIC ACIDS ORGANIC ACIDS ORGANIC CHLORINE COMPOUNDS ORGANIC COMPOUNDS ORGANIC HALOGEN COMPOUNDS PCB POLLUTION Pollution, environment geology POLYCHLORINATED BIPHENYLS REMEDIAL ACTION Soil and sediments pollution USA, Housatonic R USA, New York, Housatonic R WATER POLLUTION |
title | Use of Halogenated Benzoates and Other Halogenated Aromatic Compounds To Stimulate the Microbial Dechlorination of PCBs |
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