Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1979-12-19
1982-01-19
Garner, Vivian
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
203 63, 203 66, 2604109R, 423206R, 423293, 560214, 560248, 562521, 568 6, C07C 6738
Patent
active
043118518
ABSTRACT:
The invention includes a process wherein an olefin is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, and the catalyst is recovered from the desired reaction product and the reaction by-products and is recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed to form a reaction mass containing the BF.sub.3, the alcohol, and carboxylic acid esters in a 2:1:1 molar ratio. In the first step, the one mole of free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. An azeotrope of the product carboxylic acid ester and the alcohol and residual alcohol are removed by the distillation, leaving a residue containing a 1:2 BF.sub.3 / alcohol complex and the by-product carboxylic acid esters, which are heavier than the product carboxylic acid ester. The by-products are removed from the residue via solvent extraction and the remaining complex may be combined with an additional mole of BF.sub. 3 to form the 1:1:1 catalyst complex used in the carbonylation. The additional mole of BF.sub.3 is preferably that initially separated from the reaction mass; however, it may be obtained from an external source. The reconstituted catalyst is then preferably recycled to the carbonylation reaction. The carboxylic acid ester/alcohol mixture may be separated by azeotropic distillation using an azeotroping agent, such as octane, to recover the alcohol-octane as overhead product and the carboxylic acid ester as bottoms product.
REFERENCES:
patent: 2378009 (1945-06-01), Hanford et al.
patent: 2967873 (1961-01-01), Koch et al.
patent: 3349107 (1967-10-01), Pawlenko
Pawlenko, Chemie Ing. Techn., 40,52 (1968).
Moller, Bernstoff-Chemie, 45,129 (1964).
Jung John A.
Peress Jimmy
Chem Systems Inc.
Garner Vivian
Lewen Bert J.
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