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Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans

Mercaptocarboxylic acids and their esters, a class of difunctional compounds bearing both a mercapto and a carboxylic acid or ester functional group, are industrial chemicals of potential environmental concern. Biodegradation of such compounds was systematically investigated here, both by literature...

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Autores principales: Rücker, Christoph, Mahmoud, Waleed M. M., Schwartz, Dirk, Kümmerer, Klaus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Berlin Heidelberg 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6061509/
https://www.ncbi.nlm.nih.gov/pubmed/29667058
http://dx.doi.org/10.1007/s11356-018-1812-x
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author Rücker, Christoph
Mahmoud, Waleed M. M.
Schwartz, Dirk
Kümmerer, Klaus
author_facet Rücker, Christoph
Mahmoud, Waleed M. M.
Schwartz, Dirk
Kümmerer, Klaus
author_sort Rücker, Christoph
collection PubMed
description Mercaptocarboxylic acids and their esters, a class of difunctional compounds bearing both a mercapto and a carboxylic acid or ester functional group, are industrial chemicals of potential environmental concern. Biodegradation of such compounds was systematically investigated here, both by literature search and by experiments (Closed Bottle Test OECD 301D and Manometric Respirometry Test OECD 301F). These compounds were found either readily biodegradable or at least biodegradable to a significant extent. Some related compounds of divalent sulfur were tested for comparison (mercaptans, sulfides, disulfides). For the two relevant monofunctional compound classes, carboxylic acids/esters and mercaptans, literature data were compiled, and by comparison with structurally similar compounds without these functional groups, the influence of COOH/COOR’ and SH groups on biodegradability was evaluated. Thereby, an existing rule of thumb for biodegradation of carboxylic acids/esters was supported by experimental data, and a rule of thumb could be formulated for mercaptans. Concurrent to biodegradation, abiotic processes were observed in the experiments, rapid oxidative formation of disulfides (dimerisation of monomercaptans and cyclisation of dimercaptans) and hydrolysis of esters. Some problems that compromise the reproducibility of biodegradation test results were discussed. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s11356-018-1812-x) contains supplementary material, which is available to authorized users.
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spelling pubmed-60615092018-08-09 Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans Rücker, Christoph Mahmoud, Waleed M. M. Schwartz, Dirk Kümmerer, Klaus Environ Sci Pollut Res Int Research Article Mercaptocarboxylic acids and their esters, a class of difunctional compounds bearing both a mercapto and a carboxylic acid or ester functional group, are industrial chemicals of potential environmental concern. Biodegradation of such compounds was systematically investigated here, both by literature search and by experiments (Closed Bottle Test OECD 301D and Manometric Respirometry Test OECD 301F). These compounds were found either readily biodegradable or at least biodegradable to a significant extent. Some related compounds of divalent sulfur were tested for comparison (mercaptans, sulfides, disulfides). For the two relevant monofunctional compound classes, carboxylic acids/esters and mercaptans, literature data were compiled, and by comparison with structurally similar compounds without these functional groups, the influence of COOH/COOR’ and SH groups on biodegradability was evaluated. Thereby, an existing rule of thumb for biodegradation of carboxylic acids/esters was supported by experimental data, and a rule of thumb could be formulated for mercaptans. Concurrent to biodegradation, abiotic processes were observed in the experiments, rapid oxidative formation of disulfides (dimerisation of monomercaptans and cyclisation of dimercaptans) and hydrolysis of esters. Some problems that compromise the reproducibility of biodegradation test results were discussed. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s11356-018-1812-x) contains supplementary material, which is available to authorized users. Springer Berlin Heidelberg 2018-04-17 2018 /pmc/articles/PMC6061509/ /pubmed/29667058 http://dx.doi.org/10.1007/s11356-018-1812-x Text en © The Author(s) 2018 Open Access This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Research Article
Rücker, Christoph
Mahmoud, Waleed M. M.
Schwartz, Dirk
Kümmerer, Klaus
Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
title Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
title_full Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
title_fullStr Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
title_full_unstemmed Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
title_short Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
title_sort biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6061509/
https://www.ncbi.nlm.nih.gov/pubmed/29667058
http://dx.doi.org/10.1007/s11356-018-1812-x
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