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Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process

The present article describes the one-pot synthesis of double- and single-tailed surfactants by a cascade process that involves the hydrolysis/butanolysis of pectins into butyl galacturonate monosaccharides followed by transesterification/transacetalisation processes with fatty alcohols, and subsequ...

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Autores principales: Milliasseau, Damien, Jeftić, Jelena, Pessel, Freddy, Plusquellec, Daniel, Benvegnu, Thierry
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8036317/
https://www.ncbi.nlm.nih.gov/pubmed/33807131
http://dx.doi.org/10.3390/molecules26071956
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author Milliasseau, Damien
Jeftić, Jelena
Pessel, Freddy
Plusquellec, Daniel
Benvegnu, Thierry
author_facet Milliasseau, Damien
Jeftić, Jelena
Pessel, Freddy
Plusquellec, Daniel
Benvegnu, Thierry
author_sort Milliasseau, Damien
collection PubMed
description The present article describes the one-pot synthesis of double- and single-tailed surfactants by a cascade process that involves the hydrolysis/butanolysis of pectins into butyl galacturonate monosaccharides followed by transesterification/transacetalisation processes with fatty alcohols, and subsequent aqueous basic and acid treatments. The cascade mode allows the depolymerisation to proceed more efficiently, and the purification conditions are optimised to make the production of single-tailed surfactants more manufacturable. These products in a pure form or as mixtures with alkyl glycosides resulting from butanolysis and transglycosylation of pectin-derived hexoses, exhibit attractive surface-tension properties, especially for the n-oleyl ᴅ-galactosiduronic acid products. In addition, a readily biodegradability and an absence of aquatic ecotoxicity are shown for the galacturonic acid derivatives possessing an oleyl alkyl chain at the anomeric position.
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spelling pubmed-80363172021-04-12 Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process Milliasseau, Damien Jeftić, Jelena Pessel, Freddy Plusquellec, Daniel Benvegnu, Thierry Molecules Article The present article describes the one-pot synthesis of double- and single-tailed surfactants by a cascade process that involves the hydrolysis/butanolysis of pectins into butyl galacturonate monosaccharides followed by transesterification/transacetalisation processes with fatty alcohols, and subsequent aqueous basic and acid treatments. The cascade mode allows the depolymerisation to proceed more efficiently, and the purification conditions are optimised to make the production of single-tailed surfactants more manufacturable. These products in a pure form or as mixtures with alkyl glycosides resulting from butanolysis and transglycosylation of pectin-derived hexoses, exhibit attractive surface-tension properties, especially for the n-oleyl ᴅ-galactosiduronic acid products. In addition, a readily biodegradability and an absence of aquatic ecotoxicity are shown for the galacturonic acid derivatives possessing an oleyl alkyl chain at the anomeric position. MDPI 2021-03-31 /pmc/articles/PMC8036317/ /pubmed/33807131 http://dx.doi.org/10.3390/molecules26071956 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ).
spellingShingle Article
Milliasseau, Damien
Jeftić, Jelena
Pessel, Freddy
Plusquellec, Daniel
Benvegnu, Thierry
Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process
title Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process
title_full Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process
title_fullStr Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process
title_full_unstemmed Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process
title_short Transformation of Pectins into Non-Ionic or Anionic Surfactants Using a One-Pot and Cascade Mode Process
title_sort transformation of pectins into non-ionic or anionic surfactants using a one-pot and cascade mode process
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8036317/
https://www.ncbi.nlm.nih.gov/pubmed/33807131
http://dx.doi.org/10.3390/molecules26071956
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