Premium
Conversion of methyl 9(10)‐formylstearate to carboxymethylstearate
Author(s) -
Dufek E. J.
Publication year - 1978
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/bf02669924
Subject(s) - hydroformylation , methylene , chemistry , pyrolysis , methanol , yield (engineering) , methyl acetate , hydroxymethyl , methyl group , organic chemistry , alcohol , medicinal chemistry , polymer chemistry , catalysis , group (periodic table) , materials science , rhodium , metallurgy
Methyl 9(10)‐formylstearate was converted to methyl 9(10)‐carboxymethylstearate. The reactions to prepare the intermediates methyl 9(10)‐hydroxymethyl‐, 9(10)‐ace toxymethyl‐, 9(10)‐methylene‐, and 9(10)‐formylmethylstearate are described. Methyl 9(10)‐hydroxy methylstearate readily loses methanol and forms a trimeric polymer. The acetate of the primary alcohol when pyrolyzed gives 59% yield of methyl 9(10)‐methylenestearate. Hydroformylation of the methylene compound followed by permanganate oxidation gave methyl carboxymethylstearate. Evidence is presented to show that pyrolysis of the acetate ester and hydroformylation of the pyrolysis product produce, respectively, only the methylene and formylmethylstearates. Rates of esterification‐transes terification of methyl 9(10)‐carboxymethyl sterate show that the carboxymethyl group is 2–3 times as active as the carboxyl group in methyl 9(10)‐carboxystearate and that the terminal carboxyl group is about 10 times more active towards esterification than the branched carboxymethyl group.