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Conversion of Methyl Oleate to Branched-Chain Derivatives
- 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.
- Author(s):
- Dailey, Oliver D. Jr. , Prevost, Nicolette
- Subject(s):
- vegetable oil , oleic acid , methylation , branched chain fatty acids , bromination , chemical analysis , chemical structure , spectral analysis , biodiesel
- Description:
- Includes references
- Source:
- Journal of the American Oil Chemists' Society 2007 June, v. 84, no. 6
- Language:
- English
- Year:
- 2007
- Publisher:
- Berlin/Heidelberg : Springer-Verlag
- Collection:
- Journal Articles, USDA Authors, Peer-Reviewed
- File:
- Download [PDF]
- Rights:
- Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.
