The preparation of 1-chloro-2-butene by the reaction of butadiene and hydrogen chloride is taught in U.S. Pat. No. 3,055,954 to Montagna et al.
The preparation of unsaturated carboxylic acid halides by the reaction of 1-chloro-2-butene (crotyl chloride) and carbon monoxide and a palladium catalyst is taught in U.S. Pat. No. 3,338,961 to Closson et al. See Example 8 in particular. Journal of the Chemical Society, 1964, pages 1588-1594, describes the use of palladium chloride complexes to react 3-chloro-1-butene with carbon monoxide to form 3-pentenoyl chloride. See Table 2, Page 1589.
The preparation of 3-pentenoic acid from pentenoyl chloride is disclosed in Bunel et al. U.S. Pat. No. 5,288,903.
The reaction of acyl halides with water to form acids is taught in standard organic chemistry textbooks.
3-pentenoic acid is an intermediate in the preparation of adipic acid from butadiene. See Burke U.S. Pat. No. 4,788,333. Adipic acid is a monomer used in the preparation of 6,6 nylon.
It is an object of the present invention to provide a process for the production of 3-pentenoic acid and 3-chloro-1-butene and 1-chloro-2-butene by a process in which there is less yield loss than when these desired products are formed in separate reactions.
USPTO Backgrounds
USPTO Backgrounds