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Synthesis of Chloroalkoxy eicosanoic and docosanoic acids from meadowfoam fatty acids by oxidation with aqueous sodium hypochlorite
Author(s) -
Mund Melissa S.,
Isbell Terry A.
Publication year - 1999
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf03028872
Subject(s) - chemistry , sodium hypochlorite , methanol , alcohol , organic chemistry , aqueous solution , hypochlorite , fatty acid , yield (engineering) , chromatography , metallurgy , materials science
Chloroalkoxy substituted C 20 and C 22 fatty acids can be synthesized from the unsaturated fatty acids in meadow‐foam 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 3 h. Chlorohydroxy fatty acid derivatives are formed as by‐products owing to the presence of water in the reaction mixture. Chlorinated δ‐lactones are also produced by direct reaction of sodium hypochlorite with the Δ5 unsaturated fatty acids present in meadowfoam or by ring closure of the 6‐chloro‐5‐hydroxy fatty acids. The product yield of chloroalkoxy 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 maximal yields (50–60%) of chloroalkoxy fatty acids whereas the secondary alcohol 2‐propanol gives a 30% yield. Chloroalkoxy fatty acid yields can be increased to 75–80% by elimination of water from the reaction mixture through a procedure that partitions sodium hypochlorite from water into hexane/ethyl acetate mixtures. All of the reaction products were fully characterized using nuclear magnetic resonance and gas chromatography‐mass spectrometry.