Improved synthesis and characterization of saturated branched-chain fatty acid isomers

• Published in: European journal of lipid science and technology Vol. 114; no. 2; pp. 213 - 221
• Main Authors: Ngo, Helen L., Hoh, Eunha, Foglia, Thomas A.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2012; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Biological and medical sciences; Fat industries; Ferrierite zeolite; Food industries; Fundamental and applied biological sciences. Psychology; Mordenite; Saturated branched-chain fatty acids; Skeletal isomerization; Triphenylphosphine; Characterization; Oils and fats industry; Saturated fatty acid; Isomerization; Ferrierite zeolite; Mordenite; Saturated branched-chain fatty acids; Triphenylphosphine; Skeletal isomerization; Isomer
• ISSN: 1438-7697; 1438-9312
• DOI: 10.1002/ejlt.201000471

The development of viable technologies for producing green products from renewable fats and oils is highly desirable since such materials can serve as replacements for non‐renewable and poorly biodegradable petroleum‐based products. Mixtures of saturated branched‐chain fatty acid isomers (sbc‐FAs), commonly referred to as isostearic acid, are important intermediates for the production of biodegradable lubricants, cosmetics, emollients, and hydraulic fluids. Present methods for producing sbc‐FAs, however, often give low yields of sbc‐FAs or sbc‐FA preparations with a high content of dimer acid fatty acid co‐products. This study reports an improved route to synthesizing sbc‐FAs from monounsaturated fatty acids using a modified H‐Ferrierite zeolite catalyst in conjunction with small amounts of triphenylphosphine additive. The yields of sbc‐FAs (up to 80 wt%) and co‐products (up to15 wt%) were determined using a modification of a previously reported GC method. A more detailed analysis of the distribution of sbc‐FA isomers in the products was made by the combined use of GC × GC‐TOF‐MS. Additionally, it was found that the H‐Ferrierite zeolite catalyst was recyclable and reusable up to 10 times without significant loss of activity and selectivity for sbc‐FAs. Fatty acid isomerization of oleic acid using H‐Ferrierite zeolites.