Journal ArticleDOI
Catalytic carboxylation of fats. Carboxy acids and esters from monounsaturates
E. N. Frankel,F. L. Thomas +1 more
TLDR
In this article, a highly selective catalytic, one-step synthesis of oleic acid into 9(10)-carboxystearic acid in high yields is described.Abstract:
A highly selective catalytic, one-step synthesis converts oleic acid into 9(10)-carboxystearic acid in high yields (85–99%). Hydrocarboxylation with water and carbon monoxide under pressure (3000–4000 psi) is catalyzed with a mixture of palladium chloride and triphenylphosphine at 120–150 C with or without acetone or acetic acid solvents. Palladium supported on carbon is also an effective hydrocarboxylation catalyst in the presence of triphenylphosphine and HCl. Methyl 9(10)-carbomethoxystearate was prepared by catalytic carbomethoxylation of methyl oleate with methanol and carbon monoxide but in lower yields. The carboxystearic acids and esters consisted of the 9 and 10 isomers (87–94%) in approximately equal proportions. This catalytic carboxylation procedure is a more efficient route to carboxystearic acid and ester than the two-step hydroformylation-oxidation process reported previously. Carboxylated acids, methyl esters and triglycerides of potential industrial importance have been prepared.read more
Citations
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Journal ArticleDOI
Palladium-catalyzed Reppe carbonylation.
TL;DR: Although hydroesterification yields esters from alkenes, alkynes, and dienes in fewer steps than hydroformylation does, the latter has some advantages at the current state of the art; thus, continued effort in the field is warranted.
Journal ArticleDOI
Dicarboxylic acid esters from the carbonylation of unsaturated esters under mild conditions
TL;DR: The methoxycarbonylation of unsaturated acids or esters catalysed by Pd complexes of bis(ditertiarybutyl-phosphinomethyl)benzene (DTBPMB) produces α,ω-diesters with selectivities >95%, even if the double bond is deep in the chain or conjugated to the carbonyl group.
Journal ArticleDOI
Catalytic hydroformylation and hydrocarboxylation of unsaturated fatty compounds
E. N. Frankel,E. H. Pryde +1 more
TL;DR: The two catalyst systems rhodium-triphenylphosphine (RTPH) and palladium chloride-triphensylphophosphine were investigated for the respective hydroformylation and hydrocarboxylation of oleic acid or ester to produce C-19 bifunctional compounds as mentioned in this paper.
Journal ArticleDOI
Recyclable homogeneous catalyst for the hydroesterification of methyl oleate in thermomorphic solvent systems
TL;DR: In this paper, an atom economic hydroesterification of methyl oleate to linear and branched diesters is described, where a high selectivity of 94% towards linear products was obtained if no solvent was used.
Journal ArticleDOI
The mission of addition and fission – catalytic functionalization of oleochemicals
TL;DR: In this paper, the authors describe the mission of the scientific work that is performed at the chair of Technical Chemistry at the TU Dortmund towards selective and atom economic functionalization of oleochemicals.
References
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Journal ArticleDOI
Organic Syntheses by Means of Noble Metal Compounds. VIII.1 Catalytic Carbonylation of Allylic Compounds with Palladium Chloride
Journal ArticleDOI
Homogeneous catalytic hydrogenation of unsaturated fats: Group VIB metal carbonyl complexes
E. N. Frankel,F. L. Little +1 more
TL;DR: In this article, Carbonell complexes of Cr, Mo and W have been studied as soluble catalysts for the hydrogenation of methyl sorbate and of methyl esters from soybean oil.
Journal ArticleDOI
Carbonylation of Olefins under Mild Temperature Conditions in the Presence of Palladium Complexes
TL;DR: In this paper, a search for catalysts that allow carbonylation reactions on olefins to proceed below 100 °C was conducted, and complex palladium(II) compounds having the formula LmPdXn were found to be catalytically active.