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Comparison of the reaction products of oleic acid ozonized in BCl3-, HCl- and BF3-MeOH media

✍ Scribed by J-L. Sebedio; W.M.N. Ratnayake; R.G. Ackman

Publisher: Elsevier Science
Year: 1984
Tongue: English
Weight: 313 KB
Volume: 35
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(84)90029-x

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✦ Synopsis

In BFfMeOH medium, the principal ozonolysis reaction products of oleic acid were methyl nonanoate (MMCg) and dimethyl azelate (DMCg) in yields of 98% with formation of minor secondary reaction products (methyl octanoate, nonaldehyde with nonaldehyde dimethyl acetal and dimethyl suberate, plus the C 9 half-ester-aldehyde, with its corresponding acetal). The gas-liquid chromatographic analysis of the ozonolysis reaction products in BCI~-and HCI-MeOH revealed the existence of 4 major components with low yields of methyl nonanoate and dimethyl azelate (45-50%). The two other major reaction products, isolated by a combination of thinqayer chromatography (TLC) and high-pressure liquid chromatography (HPLC), were identified as the chlorinated acetals, 1,1-dimethoxy-2-chloro-nonane and the 8-chloro-9,9-dimethoxy methyl nonanoate.

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