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Abstract
AbstractA sequential one‐pot chemoenzymatic procedure for the conversion of diol 1, easily obtained from oleic acid, into pelargonic and azelaic acids is herein described. The oxidation of diol 1 into a mixture of the corresponding regioisomeric hydroxyketones was promoted by an alcohol dehydrogenase from Micrococcus luteus, selected after an extensive screening of commercial enzyme kits and strain collections. The stereochemistry of the oxidation process of chiral diol 1 was also investigated. The hydroxyketones obtained by the biocatalyzed oxidation were submitted to further oxidative cleavage by a mild treatment with aqueous NaClO in a biphasic mixture, affording pelargonic and azelaic acids in high yield (76 and 71 %, respectively) with no need of column chromatography.
Highlights
The limited availability of non-renewable petroleum-based sources and the increasing drive to reduce waste and energy consumption have prompted the scientific community to move towards the optimization of greener manufacturing processes
We describe the development of the synthetic strategy shown in Scheme 2b, along with the results obtained by studying the stereochemical course of the oxidation of rac-threo-1 with recombinant alcohol dehydrogenase (ADH) from M. luteus NCTC2665
A screening of selected whole-cell microorganisms belonging to the Polish Collection of Microorganisms (PCM) Institute of Immunology and Experimental Therapy of the Polish Academy of Sciences in Wroclaw, and the German Collection of Microorganisms and Cell Cultures (DSMZ) was performed
Summary
The limited availability of non-renewable petroleum-based sources and the increasing drive to reduce waste and energy consumption have prompted the scientific community to move towards the optimization of greener manufacturing processes. Soapstock is the by-product obtained from the neutralization step of the refining process to which vegetable seed oil is submitted after extraction.[2] It consists of an alkaline aqueous emulsion of lipids, the composition of which depends on the botanical origin of the seeds and the conditions of refining and storage. It usually contains water (45–50 %, percentages vary according to the operating conditions), fatty acid sodium salts (determined as free acids, 10 %), triacylglycerols and diacylglycerols (12 %), residual phospholipids (9 %), pigments and other minor components (24 %).[3] During the refining process, soapstock is collected by centrifugation and submitted to a socalled splitting step: it is treated with sulfuric or hydrochloric acid, to recover free fatty acids with concomitant partial hydrolysis of residual oil, affording oleins, a mixture of free fatty acids in triglycerides.[4]
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