The Dow Chemical Company

Robert T Klun

Dennis A Hucul

Craig B Murchison

Thomas W Regulski

The invention is a process for preparing a 2-halo-1-alkene comprising contacting a hydrocarbon stream with a hydrogen halide, in the presence of water and an effective amount of a catalyst, at a temperature between about 100.degree. C. and about 400.degree. C., wherein; the hydrocarbon stream comprises a 1,2-diene, a terminal acetylene or mixtures thereof, represented by the formulas CH.sub.2 .dbd.C.dbd.CH--R or CH.tbd.C--CH.sub.2 --R wherein R is hydrogen, alkyl, cycloalkyl or aryl and may be substituted or unsubstituted; the water is present in an amount of between about 1,000 and 100,000 parts per million by weight; and the catalyst comprises carbon, silica alumina, aluminosilicates, silica gel, silica, silica magnesia, silicalite, group IIIA, IIIB, IVA, IVB or V metal oxides or rare earth oxides.

Preparation of 2-halo-1-alkenes from hydrocarbon streams

The invention is a process for preparing a 2-halo-1-alkene comprising contacting a hydrocarbon stream with a hydrogen halide, in the presence of water and an effective amount of a catalyst, at a temperature between about 20.degree. C. and about 400.degree. C., wherein; the hydrocarbon stream comprises a 1,2-diene, a terminal acetylene or mixtures thereof, represented by the formulas CH.sub.2 .dbd.C.dbd.CH--R or CH.tbd.C--CH.sub.2 --R wherein R is hydrogen, alkyl, cycloalkyl or aryl and may be substituted or unsubstituted; the water is present in an amount capable of maintaining the selectivity of the catalyst for the insertion of the halide on the 2 carbon of the 1,2-diene or terminal acetylene; and the catalyst comprises carbon, silica alumina, aluminosilicates, silica gel, silica, silica magnesia, silicalite, group IIIA, IIIB, IVA, IVB or V metal oxides or rare earth oxides. The invention further includes the additional step of preparing an acrylate ester by contacting the 2-halo-1-alkene, with carbon monoxide and an esterifying agent such as an alcohol, phenol, carbonate, or (poly)glycol monoether, in the presence of a group VIII metal catalyst and a halogen acceptor.

Preparation of 2-halo-1-alkenes and acrylate esters from hydrocarbon

This invention is a process for the preparation of acrylate esters comprising contacting a vinyl halide with carbon monoxide and an organic carbonate in the presence of an effective amount of a group VIII metal catalyst.

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Midland, MI, United States of America

Robert T Klun