Reaction of Perfluorooctanoic Acid with Criegee Intermediates and Implications for the Atmospheric Fate of Perfluorocarboxylic Acids
The reaction of perfluorooctanoic acid with the smallest carbonyl oxide Criegee intermediate, CH2OO, has been measured and is very rapid, with a rate coefficient of (4.9 ± 0.8) × 10–10 cm3 s–1, similar to that for reactions of Criegee intermediates with other organic acids. Evidence is shown for the...
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| Veröffentlicht in: | Environmental science & technology 2019-02, Vol.53 (3), p.1245-1251 |
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| creator | Taatjes, Craig A Khan, M. Anwar H Eskola, Arkke J Percival, Carl J Osborn, David L Wallington, Timothy J Shallcross, Dudley E |
| description | The reaction of perfluorooctanoic acid with the smallest carbonyl oxide Criegee intermediate, CH2OO, has been measured and is very rapid, with a rate coefficient of (4.9 ± 0.8) × 10–10 cm3 s–1, similar to that for reactions of Criegee intermediates with other organic acids. Evidence is shown for the formation of hydroperoxymethyl perfluorooctanoate as a product. With such a large rate coefficient, reaction with Criegee intermediates can be a substantial contributor to atmospheric removal of perfluorocarboxylic acids. However, the atmospheric fates of the ester product largely regenerate the initial acid reactant. Wet deposition regenerates the perfluorocarboxylic acid via condensed-phase hydrolysis. Gas-phase reaction with OH is expected principally to result in formation of the acid anhydride, which also hydrolyzes to regenerate the acid, although a minor channel could lead to destruction of the perfluorinated backbone. |
| doi_str_mv | 10.1021/acs.est.8b05073 |
| format | Article |
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Anwar H ; Eskola, Arkke J ; Percival, Carl J ; Osborn, David L ; Wallington, Timothy J ; Shallcross, Dudley E</creator><creatorcontrib>Taatjes, Craig A ; Khan, M. Anwar H ; Eskola, Arkke J ; Percival, Carl J ; Osborn, David L ; Wallington, Timothy J ; Shallcross, Dudley E ; Sandia National Lab. (SNL-CA), Livermore, CA (United States)</creatorcontrib><description>The reaction of perfluorooctanoic acid with the smallest carbonyl oxide Criegee intermediate, CH2OO, has been measured and is very rapid, with a rate coefficient of (4.9 ± 0.8) × 10–10 cm3 s–1, similar to that for reactions of Criegee intermediates with other organic acids. Evidence is shown for the formation of hydroperoxymethyl perfluorooctanoate as a product. With such a large rate coefficient, reaction with Criegee intermediates can be a substantial contributor to atmospheric removal of perfluorocarboxylic acids. However, the atmospheric fates of the ester product largely regenerate the initial acid reactant. Wet deposition regenerates the perfluorocarboxylic acid via condensed-phase hydrolysis. Gas-phase reaction with OH is expected principally to result in formation of the acid anhydride, which also hydrolyzes to regenerate the acid, although a minor channel could lead to destruction of the perfluorinated backbone.</description><identifier>ISSN: 0013-936X</identifier><identifier>EISSN: 1520-5851</identifier><identifier>DOI: 10.1021/acs.est.8b05073</identifier><identifier>PMID: 30589541</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Acidic oxides ; Acids ; Anhydrides ; Carbonyls ; Chemical industry ; INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY ; Intermediates ; Organic acids ; Perfluoro compounds ; Perfluorooctanoic acid ; Wet deposition</subject><ispartof>Environmental science & technology, 2019-02, Vol.53 (3), p.1245-1251</ispartof><rights>Copyright American Chemical Society Feb 5, 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a466t-8dcc5d150c6badfdf3651bf7a70e505f1a159c5d99303f8691108294a458b2103</citedby><cites>FETCH-LOGICAL-a466t-8dcc5d150c6badfdf3651bf7a70e505f1a159c5d99303f8691108294a458b2103</cites><orcidid>0000-0002-9271-0282 ; 0000-0002-2249-2726 ; 0000-0002-9810-6326 ; 0000-0001-7836-3344 ; 0000000178363344 ; 0000000292710282 ; 0000000298106326 ; 0000000222492726</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.est.8b05073$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.est.8b05073$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30589541$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/servlets/purl/1492346$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Taatjes, Craig A</creatorcontrib><creatorcontrib>Khan, M. 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| source | ACS Publications |
| subjects | Acidic oxides Acids Anhydrides Carbonyls Chemical industry INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Intermediates Organic acids Perfluoro compounds Perfluorooctanoic acid Wet deposition |
| title | Reaction of Perfluorooctanoic Acid with Criegee Intermediates and Implications for the Atmospheric Fate of Perfluorocarboxylic Acids |
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