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Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route

A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolati...

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Autores principales: Brenna, Elisabetta, Colombo, Danilo, Di Lecce, Giuseppe, Gatti, Francesco G., Ghezzi, Maria Chiara, Tentori, Francesca, Tessaro, Davide, Viola, Mariacristina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7221618/
https://www.ncbi.nlm.nih.gov/pubmed/32325747
http://dx.doi.org/10.3390/molecules25081882
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author Brenna, Elisabetta
Colombo, Danilo
Di Lecce, Giuseppe
Gatti, Francesco G.
Ghezzi, Maria Chiara
Tentori, Francesca
Tessaro, Davide
Viola, Mariacristina
author_facet Brenna, Elisabetta
Colombo, Danilo
Di Lecce, Giuseppe
Gatti, Francesco G.
Ghezzi, Maria Chiara
Tentori, Francesca
Tessaro, Davide
Viola, Mariacristina
author_sort Brenna, Elisabetta
collection PubMed
description A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H(2)O(2) is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO(3))(3)∙9∙H(2)O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H(2)O(2) in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.
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spelling pubmed-72216182020-05-22 Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route Brenna, Elisabetta Colombo, Danilo Di Lecce, Giuseppe Gatti, Francesco G. Ghezzi, Maria Chiara Tentori, Francesca Tessaro, Davide Viola, Mariacristina Molecules Article A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H(2)O(2) is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO(3))(3)∙9∙H(2)O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H(2)O(2) in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid. MDPI 2020-04-18 /pmc/articles/PMC7221618/ /pubmed/32325747 http://dx.doi.org/10.3390/molecules25081882 Text en © 2020 by the authors. 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/).
spellingShingle Article
Brenna, Elisabetta
Colombo, Danilo
Di Lecce, Giuseppe
Gatti, Francesco G.
Ghezzi, Maria Chiara
Tentori, Francesca
Tessaro, Davide
Viola, Mariacristina
Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route
title Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route
title_full Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route
title_fullStr Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route
title_full_unstemmed Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route
title_short Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route
title_sort conversion of oleic acid into azelaic and pelargonic acid by a chemo-enzymatic route
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7221618/
https://www.ncbi.nlm.nih.gov/pubmed/32325747
http://dx.doi.org/10.3390/molecules25081882
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