1,4-Butanediol from hydrogenated hydroformylated allyl acetate
AssigneeGeneral Electric Company
InventorWilliam E. Smith
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Abstract
Dehydroformylation of isomeric acetoxybutyraldehydes, with minimal dehydroacetoxylation, can be accomplished at a temperature in the range of 120.degree.-250.degree. C. in a nonoxidizing atmosphere in the presence of an essentially neutral noble metal catalyst to produce allyl acetate, 1-propenyl acetate or mixtures thereof. This reaction permits recycle of the undesired isomeric acetoxybutyraldehyde products of the hydroformylation of allyl acetate of 1-propenyl acetate to the desired 4-acetoxybutyraldehyde which is an intermediate in the production of 1,4-butanediol useful in making polyesters.
Claims6
In the process for producing 1,4-butanediol by oxidatively coupling propylene with acetic acid to produce allyl acetate which is hydroformylated under hydroformylating conditions in the presence of a cobalt hydroformylating catalyst to produce a mixture comprising 4-acetoxybutyraldehyde, as the predominant product, and its two isomers, 2-acetoxybutyraldehyde and 3-acetoxy-2-methylpropionaldehyde and hydrogenating the mixture of aldehydes under hydrogenating conditions to produce a mixture comprising the acetate esters of 1,4-butanediol and its two isomers, 1,3-butanediol and 1,2-butanediol which are de-esterified under de-esterification conditions to their corresponding diols, the improvement wherein at least some of the 4-acetoxybutyraldehyde is separated from the mixture containing its two isomers to provide feedstock for the hydrogenation reaction and the mixture containing the isomers is dehydroformylated at a temperature in the range of 120.degree.-250.degree. C. in a nonoxidizing atmosphere and in the presence of a catalyst selected from the group consisting of a Group VIII noble metal and mixtures thereof or a Group VIII noble metal and mixtures thereof on an essentially neutral support to produce feedstock for the hydroformylation reaction.
Dependencies are inferred from the claim text.