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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of Chloro Alkoxy Eicosanoic and Docosanoic Acids from Meadowfoam Fatty Acids by Oxidation with Aqueous Sodium Hypochlorite

item Mund, Melissa
item Isbell, Terry

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 10, 1999
Publication Date: N/A

Interpretive Summary: Vegetable oils and their fatty acids are environmentally sound starting materials for industrial products such as lubricants, cleansers, greases, detergents, fabric softeners, cosmetics, and shampoos. Meadowfoam is a new crop in the U.S. with a unique oil. Unfortunately, the commercial markets are not fully exploiting meadowfoam and other oils. In order to develop new industrial quality products from vegetable oils, we have developed a simple, environmentally-friendly process for converting meadowfoam oil fatty acids to chloro alkoxy fatty acids (CAOFA). This process uses household bleach and alcohol and works with other vegetable oil fatty acids as well. We expect interest in the new CAOFA product to be high, and we will work with industry to test CAOFA as a new ingredient in several applications.

Technical Abstract: Chloro alkoxy substituted C20 and C22 fatty acids can be synthesized from the unsaturated fatty acids in meadowfoam oil by reaction of the fatty acids with primary or secondary alcohols and an aqueous sodium hypochlorite solution (commercial bleach). The reactions are conducted at room temperature for three hours. Chlorohydroxy fatty acid derivatives are formed as by-products due to the presence of water in the reaction mixture. Chlorinated delta lactones are also produced by direct reaction of sodium hypochlorite with the five unsaturated fatty acids present in meadowfoam or by ring closure of the 6-chloro-5-hydroxy fatty acids. The product yield of chloro alkoxy fatty acids is dependent on the nature and volume of the alcohol used in the reaction, as well as the concentration and pH of the sodium hypochlorite solution. Primary alcohols, such as methanol and butanol, produce maximum yields (50-60%) of chloro alkoxy fatty acids while the secondary alcohol, 2-propanol, gives a 30% yield. Chloro alkoxy fatty acid yields can be increased to 75-80% by elimination of water from the reaction mixture through a procedure which partitions sodium hypochlorite from water into hexane/ethyl acetate mixtures. All of the reaction products were fully characterized using NMR and GC-MS.

Last Modified: 4/22/2015
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