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Open AccessArticle

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

Dipartimento di Chimica, Materiali ed Ingegneria Chimica “Giulio Natta”, Politecnico di Milano, Via Mancinelli 7, 20131 Milano, Italy
Oleificio Zucchi S.p.A., Via Acquaviva, 26100 Cremona, Italy
Author to whom correspondence should be addressed.
The authors are listed in alphabetical order.
Academic Editor: Josefina Aleu
Molecules 2020, 25(8), 1882;
Received: 30 March 2020 / Revised: 15 April 2020 / Accepted: 16 April 2020 / Published: 18 April 2020
(This article belongs to the Special Issue Biocatalytic Synthesis of Bioactive Compounds)
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% H2O2 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(NO3)3∙9∙H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid. View Full-Text
Keywords: lipase; biocatalysis; unsaturated fatty acid; oxidative cleavage; oxidation lipase; biocatalysis; unsaturated fatty acid; oxidative cleavage; oxidation
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MDPI and ACS Style

Brenna, E.; Colombo, D.; Di Lecce, G.; Gatti, F.G.; Ghezzi, M.C.; Tentori, F.; Tessaro, D.; Viola, M. Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route. Molecules 2020, 25, 1882.

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