Design and Synthesis of Sebacic Acid from Castor Oil by New Alternate Route

• Published in: European journal of lipid science and technology 2022-05, Vol.124 (5), p.n/a
• Main Authors: Bhukya, Gandhi, Kaki, Shiva Shanker
• Format: Article
• Language: English
• Subjects: Acids; Castor oil; Chemical synthesis; Dicarboxylic acids; Esters; fatty acids; Hydroxyl groups; Isomerization; Mass spectrometry; Mass spectroscopy; Methylation; NMR; Nuclear magnetic resonance; Oil; oleochemicals; Raw materials; Ricinoleic acid; Sebacic acid; Spectral analysis; Spectrum analysis; synthesis
• ISSN: 1438-7697; 1438-9312
• DOI: 10.1002/ejlt.202100244

A simple and alternate organic synthetic route for sebacic acid, a high value ten‐carbon aliphatic dicarboxylic acid from castor oil is described in this study. Castor oil methyl esters are purified to obtain methyl ester of ricinoleic acid that is used as the starting material for the preparation of sebacic acid. The hydroxyl group of methyl ricinoleate is oxidized to corresponding 12‐oxo derivative followed by isomerization of the cis 9, 10 olefinic bond to trans 10, 11 isomer. The isomerized compound is subjected to dihydroxylation followed by oxidative cleavage and subsequent methylation to obtain dimethyl decanedioate. The dimethyl decanedioate is finally hydrolyzed to obtain sebacic acid. The intermediate compounds and final product are purified and characterized by chromatographic and spectral analysis. The final compound is analyzed by 1H and 13C‐NMR as well as high resolution mass spectrometry and compared with standard compound for the confirmation of the structure. Practical Applications: The design and preparation of sebacic acid by the novel alternate route is described. Castor oil, a renewable source, is utilized as the raw material for the preparation of sebacic acid. Isomerization of the 9, 10 cis bond to 10, 11 trans bond is the key step in the synthesis of sebacic acid. The chemical transformation of castor oil to sebacic acid by newer route is investigated. The design and preparation of sebacic acid by the novel alternate route is described. Castor oil, a renewable source, is utilized as the raw material for the preparation of sebacic acid. Isomerization of the 9, 10 cis bond to 10, 11 trans bond is the key step in the synthesis of sebacic acid. The chemical transformation of castor oil to sebacic acid by newer route is investigated.