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Oxidation of methyl formylstearate with molecular oxygen
Author(s) -
Friedrich J. P.
Publication year - 1976
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/bf02586348
Subject(s) - hydroformylation , rhodium , chemistry , catalysis , methyl oleate , methyl acetate , oxygen , distillation , organic chemistry , calcination , calcium
Methyl formylstearate, containing soluble rhodium complex from rhodium‐catalyzed hydroformylation of methyl oleate, is oxidized in an emulsion to methyl carboxystearate. The reaction is carried out in a closed system at 20–25 C in the presence of either air or oxygen (1–3 atm). Conversion to methyl carboxystearate is 87–89% in 2–3 hr; when catalytic amounts of calcium acetate are present, 93–95% is converted. The principal byproduct of oxidation is methyl formyloxystearate, formation of which is suppressed by calcium acetate. Distillation of crude methyl carboxystearate yields a residue containing soluble rhodium (and calcium acetate if used), which after calcining in the presence of a refractory support produces an effective hydroformylation catalyst. Recovery and regeneration of this catalyst provide an economically feasible batch process for methyl carboxystearate.