| Title: | Conversion of Methyl Oleate to Branched-Chain Derivatives. |
| Authors: | Dailey, Oliver D. Jr.
Prevost, Nicolette
USDA, ARS |
| Source: | Journal of the American Oil Chemists' Society. 2007 June, v. 84, no. 6 Berlin/Heidelberg : Springer-Verlag, p. 565-571. |
| NALT Subjects: | vegetable oil
oleic acid
methylation
branched chain fatty acids
bromination
chemical analysis
chemical structure
spectral analysis
biodiesel |
| Issue Date: | Jun-2007 |
| Abstract: | Studies were conducted in the synthetic conversion of oleic acid to mid-chain branched fatty acids. Methyl oleate was brominated in the allylic positions. Reaction of the allylic bromides with lithium dimethylcuprate gave primarily the desired branched-chain derivatives (93% of product mixture). The product had a significantly lower crystallization temperature in comparison with methyl oleate. Reaction of the allylic bromides with lithium di-n-butylcuprate or lithium di-sec-butylcuprate also gave branched-chain derivatives, but in this instance there was the complication of attack on the ester functionality in the fashion of a Grignard reagent. Details of the syntheses and the properties of the products (with emphasis on low-temperature properties) are discussed. |
| URI: | http://hdl.handle.net/10113/2927 |
| Appears in Collections: | USDA Research and Information
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