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US 5,288,903 AGranted
Preparation of 3-pentenoic acid and a catalyst therefore
AssigneeE. I. Du Pont de Nemours and Company
InventorsEmilio E. Bunel, Chen-Chou Chiang, Michael B. D'Amore, Erik J. Schaumann, Leon S. Scott
Life of this patent
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Abstract
Preparation of 3-pentenoic acid by the reaction of 3-pentenoylchloride, water and butadiene. 3-chloro-1-butene and 1-chloro-2-butene are also formed. Preferably the 3-pentenoylchloride is formed by the reaction of chlorobutene with carbon monoxide using a palladium catalyst.
Claims13
A process for the preparation of 3-pentenoic acid which comprises:
- a) reacting a chlorobutene selected from the group consisting of 3-chloro-1-butene, and 1-chloro-2-butene, and carbon monoxide in the presence of 0.05 to 5 percent by weight of a palladium catalyst at a temperature between 90 and 190 degrees C. and at a carbon monoxide pressure of between 250 and 5,000 psig to form a reaction mixture containing 3-pentenoylchloride, carbon monoxide, 3-chloro-1-butene and 1-chloro-2-butene,
- b) separating carbon monoxide from the reaction mixture by heating the mixture at a temperature in the range of 100 to 140 degrees C. at a pressure of 25 to 1500 psig,
- c) separating a mixture containing 3-pentenoylchloride and chlorobutenes from the remaining portion of the reaction mixture by distillation, and simultaneously forming C.sub.10 H.sub.11 O.sub.4 PdCl,
- d) passing C.sub.10 H.sub.11 O.sub.4 PdCl to step a) above,
- e) combining the separated mixture containing 3-pentenoylchloride and chlorobutenes with water, butadiene, and hydrochloric acid to form a mixture where the ratio of butadiene to pentenoylchloride is 1:1 to 6:1 and the molar ratio of water to 3-pentenoylchloride is 1:1 to 15:1, and reacting this mixture at a temperature in the range of about 0 degrees C. to 100 degrees C., and at a pressure of about 50 to 600 psig, and forming a two phase mixture comprising an organic phase containing 3-pentenoic acid, chlorovaleric acid, and additional chlorobutene selected from the group consisting of 3-chloro-1-butene and 1-chloro-2-butene, and an aqueous phase,
- f) separating the two phases and separating chlorobutenes from the organic phase by distillation and passing the chlorobutenes to step a) above,
- g) separating 3-pentenoic acid from the organic phase by distilling the mixture.
4 more elements
A process for the preparation of 3-pentenoylchloride which comprises:
- a) reacting a chlorobutene selected from the group consisting of 3-chloro-1-butene and 1-chloro-2-butene, and carbon monoxide in the presence of 0.05 to 5 percent by weight palladium catalyst of formula C.sub.10 H.sub.11 O.sub.4 PdCl at a temperature between 90 and 190 degrees C. and at a carbon monoxide pressure of between 500 and 5,000 psig to form a reaction mixture containing 3-pentenoylchloride, carbon monoxide, 3-chloro-1-butene and 1-chloro-2butene,
- b) separating carbon monoxide from the reaction mixture by heating the mixture at a temperature in the range of 100 to 140 degrees C. at a pressure of 25 to 1500 psig,
- c) separating a mixture containing 3-pentenoylchloride and chlorobutene from the remaining portion of the reaction mixture by distillation.
A process for the preparation of C.sub.10 H.sub.11 O.sub.4 PdCl which comprises:
- a) reacting a chlorobutene selected from the group consisting of 3-chloro-1-butene and 1-chloro-2-butene, and carbon monoxide in the presence of 0.05 to 5 mole percent by weight palladium catalyst at a temperature between 90 and 190 degrees C. and at a carbon monoxide pressure of between 500 and 5,000 psig. to form a reaction mixture containing 3-pentenoylchloride, carbon monoxide, 3-chloro-1-butene and 1-chloro-2-butene,
- b) separating carbon monoxide from the reaction mixture by heating the mixture at a temperature in the range of 100 to 140 degrees C. at a pressure of 25 to 1500 psig,
- c) separating a mixture containing 3-pentenoylchloride and chlorobutene from the reaction mixture by distillation, and simultaneously forming C.sub.10 H.sub.11 O.sub.4 PdCl.
C.sub.10 H.sub.11 O.sub.4 PdCl having the structural formula:
- ##STR4##
A process for the simultaneous preparation of 3-pentenoic acid, 3-chloro-1-butene and 1-chloro-2-butene which comprises:
- a) combining 3-pentenoylchloride with water, butadiene, and hydrochloric acid to form a mixture where the ratio of butadiene to pentenoylchloride is 1:1 to 6:1 and the molar ratio of water to 3-pentenoylchloride is 1:1 to 15:1, and reacting this mixture at a temperature in the range of about 0 degrees C. to 100 degrees C., preferably 30 to 50 degrees C., and at a pressure of about 50 to 600 psig to form a mixture comprising an organic phase containing 3-pentenoic acid, chlorovaleric acid, 3-chloro-1-butene and 1-chloro-2-butene, and an aqueous phase,
- b) separating the two phases and separating said chlorobutenes from the organic by distillation,
- c) separating 3-pentenoic acid from the organic phase by distilling the mixture.
A process for the preparation of 3-pentenoic acid which comprises:
- a) reacting a chlorobutene selected from the group consisting of 3-chloro-1-butene, and 1-chloro-2-butene, and carbon monoxide in the presence of 0.05 to 5 percent by weight of a palladium catalyst at a temperature between 90 and 190 degrees C. and at a carbon monoxide pressure of between 250 and 5,000 psig to form a reaction mixture containing 3-pentenoylchloride, carbon monoxide, 3-chloro-1-butene and 1-chloro-2-butene,
- b) combining the reaction mixture with water, butadiene, and hydrochloric acid to form a mixture where the ratio of butadiene to pentenoylchloride is 1:1 to 6:1 and the molar ratio of water to 3-pentenoylchloride is 1:1 to 15:1, and reacting this mixture at a temperature in the range of about 0 degrees C. to 100 degrees C., and at a pressure of about 50 to 600 psig to form a mixture comprising an organic phase containing 3-pentenoic acid, chlorovaleric acid, and additional chlorobutene selected from the group consisting of 3-chloro-1-butene and 1-chloro-2-butene, and an aqueous phase,
- c) separating said additional chlorobutenes from the organic phase by distillation and passing the chlorobutene to step a) above,
- d) separating 3-pentenoic acid from the organic phase by distilling the mixture,
- e) extracting the catalyst from the aqueous phase with an organic solvent and passing the extract to step a) above.
2 more elements
Dependencies are inferred from the claim text.