Cargando…
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...
Autores principales: | , , , , , , , |
---|---|
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 |
_version_ | 1783533402102693888 |
---|---|
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. |
format | Online Article Text |
id | pubmed-7221618 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT brennaelisabetta conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT colombodanilo conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT dileccegiuseppe conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT gattifrancescog conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT ghezzimariachiara conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT tentorifrancesca conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT tessarodavide conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute AT violamariacristina conversionofoleicacidintoazelaicandpelargonicacidbyachemoenzymaticroute |