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. 2020 Apr 18;25(8):1882.
doi: 10.3390/molecules25081882.

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

Elisabetta Brenna  1 , Danilo Colombo  1 , Giuseppe Di Lecce  2 , Francesco G Gatti  1 , Maria Chiara Ghezzi  1 , Francesca Tentori  1 , Davide Tessaro  1 , Mariacristina Viola  1
Affiliations

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

Elisabetta Brenna et al. Molecules. .

Abstract

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.

Keywords: biocatalysis; lipase; oxidation; oxidative cleavage; unsaturated fatty acid.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Sebacic acid (1), azelaic acid (2), pelargonic acid (3), and oleic acid (4).
Figure 2
Figure 2
Synthesis of azelaic acid (2) from oleic acid (4) according to references [19,20].
Figure 3
Figure 3
The synthesis of azelaic acid (2) from oleic acid (4) described in this paper. (i) H2O2 35%, Novozyme 435, acetonitrile, 5 h, 50 °C; (ii) NaHSO3 saturated solution, H2SO4 2 M, 3 h, r.t.; (iii) atmospheric O2, cat. Fe(NO3)3∙9 H2O/TEMPO/NaCl, toluene, 5 h, 100 °C; (iv) 35% H2O2, toluene, 3 h, 30 °C.
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