Research Article

Synthesis and Characterization of Branched-Chain Derivatives of Methyl Oleate

  1. Oliver D. Dailey Jr.,
  2. Nicolette T. Prevost1,
  3. Gary D. Strahan2

Article first published online: 5 AUG 2008

DOI: 10.1002/clen.200800058

Issue

CLEAN – Soil, Air, Water

CLEAN – Soil, Air, Water

Special Issue: Feedstocks for the Future: Renewables in Green Chemistry

Volume 36, Issue 8, pages 687–693, August 2008

Additional Information

How to Cite

Dailey, O. D., Prevost, N. T. and Strahan, G. D. (2008), Synthesis and Characterization of Branched-Chain Derivatives of Methyl Oleate. Clean Soil Air Water, 36: 687–693. doi: 10.1002/clen.200800058

Author Information

  1. 1

    USDA, ARS, Southern Regional Research Center, New Orleans, LA, USA.

  2. 2

    USDA, ARS, Eastern Regional Research Center, Wyndmoor, PA, USA.

Publication History

  1. Issue published online: 5 AUG 2008
  2. Article first published online: 5 AUG 2008
  3. Manuscript Revised: 15 MAY 2008
  4. Manuscript Received: 4 MAR 2008

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Keywords:

  • Branched-chain fatty acids;
  • Differential Scanning Calorimetry (DSC);
  • Low-temperature properties;
  • NMR;
  • Organocuprate reagents

Abstract

Oleic acid is one of the most abundant fatty acid components of the triglycerides in many vegetable oils, such as cottonseed oil. As part of a project to develop new and expanded uses of oilseed products and by-products (such as biodiesel, fuel additives, and lubricants), studies were conducted on the synthetic conversion of oleic acid (in ester form) to branched-chain fatty acid esters. In these studies, methyl oleate was brominated in the allylic position and subsequently treated with organocuprate reagents to produce novel branched-chain derivatives (ethyl, n-butyl, n-hexyl, phenyl). Details of the syntheses, characterization (GC/MS and NMR), and the properties of the products (with emphasis on low-temperature properties) are discussed. Several of the synthesized products exhibited significantly lower re-crystallization temperatures in comparison with methyl oleate and may prove useful as additives to biodiesel for use at low temperatures.

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