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Open AccessArticle

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

1
Dipartimento di Chimica, Materiali ed Ingegneria Chimica “Giulio Natta”, Politecnico di Milano, Via Mancinelli 7, 20131 Milano, Italy
2
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; https://doi.org/10.3390/molecules25081882
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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