Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 5/14/1997
Publication Date: N/A
Citation: Interpretive Summary:
Technical Abstract: The viability of a fatty acid derivative in a commercial or industrial application is dependent on the physical properties of the derivatized fatty acid and the practicality of synthesizing the derivative. Industry has shown interest in synthesizing branched-chain fatty acids which exhibit different viscosities, melting points, and oxidative stabilities than their normal chain counterparts. The unique physical properties of these branched compounds increase their potential for use in lubricants, cosmetics, and other applications. Most branched chain fatty acids have branching sites alpha to the carboxylic acid or on the terminus of the chain. The synthesis of these compounds usually involve multiple steps or high pressure rearrangement of straight chain fatty acids with heterogeneous catalysts. In an effort to explore the potential uses of fatty acids derived from meadowfoam seed, we decided to investigate a more practical synthesis of fatty acid derivatives with physical propertie similar to those of the branched chain fatty acids. We have synthesized several different oxygenated branched chain fatty acids. We have found that addition of a NaOCl solution (bleach), pH adjusted with acetic acid, to a mixture of meadowfoam fatty acids and methanol produces positional isomers of chloromethoxy eicosanoic acid. When the reaction is carried out at room temperature a 60% yield of chloro ether is obtained after 30 min. The pH of the solution, temperature, alcohol concentration, and alcohol chain length all play a role in the product distribution. The chloro ethers and all reaction byproducts were separated chromatographically and characterized by 1H NMR, 13C NMR, DEPT and GC-MS.