Dimethyl 9-Octadecenedioate and 9-Oktadecene from Methyl Oleate Via a Ruthenium-Catalyzed Homo Olefin Metathesis Reaction

Abstract

Oleic acid, one of the major components of palm oil, has attracted much interest in modern oleochemistry. The internal olefin group in oleic acid is a useful functional group in the transformation of a fatty acid to other functional chemicals and materials. In this paper, we discuss the application of the olefin metathesis reaction by preparing a long-chain dicarboxylic acid and alkene from the ester of oleic acid. The internal olefin metathesis reaction of methyl oleate produced dimethyl 9-oktadecendioate and 9-octadecene in the presence of a ruthenium Grubbs II (second generation) catalyst with a 51% yield. We also found that there was a higher amount of the E isomer products than the Z isomer products.

Morphological and molecular comparison as a useful tool for identification of the three centric marine diatoms (Bacillariophyceae: Chaetoceros)

“…5 ). The characteristic peaks were similar to the results of previous studies (Roswanda et al 2017 ; Otto et al 2014 ; Singer et al 1996 ). The correlation between proton and carbon signals observed around 1.73–1.29 ppm corresponded to arachidic acid, palmitic acid and stearic acid.…”

Escherichia coli-Derived γ-Lactams and Structurally Related Metabolites Are Produced at the Intersection of Colibactin and Fatty Acid Biosynthesis

“…The double bond geometry at C-7/C-8 in 2 was assigned as Z by observing that the pattern of the olefinic proton signals in the 1 H NMR spectrum of 2 was similar to that of methyl oleate ( Z ) rather than that of methyl elaidate ( E ) (Figure S3). − Thus, the structure of 2 was determined as shown in Figure . While characterizing the structures of 1 and 2 , we revisited our previous domain-targeted metabolomics (DTM) data wherein individual catalytic domains within the colibactin pathway were inactivated using genome editing and the resulting metabolome from each mutant was analyzed .…”