Preparation of 1,2-butylene oxide

Details Preparation of 1,2-butylene oxide Preparation of 1,2-butylene oxide

1996-12-27

1998-06-23

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30100

Patent

active

057707472

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 PCT/EP95/02337 , Jun. 16, 1995.
The present invention relates to a process for the preparation of 1,2-butylene oxide by the catalytic hydrogenation of vinyl oxirane
The catalytic hydrogenation of vinyl oxirane over catalysts consisting of palladium on aluminum oxide or palladium on activated charcoal is described in U.S. Pat. No. 5,077,418 and U.S. Pat. No. 5,117,013 and also in Neftekhimiya 33, 131 (1993). The yields, selectivities and conversions in this process are unsatisfactory.
It was the object of the present invention to provide a process for the preparation of 1,2-butylene oxide, which makes it possible to prepare 1,2-butylene oxide from vinyloxirane with better conversions, yields, and selectivities than in the prior art.
Accordingly, we have found a process for the preparation of 1,2-butylene oxide by the catalytic hydrogenation of vinyl oxirane, wherein use is made of a palladium catalyst on a support of barium sulfate, zirconium dioxide or titanium dioxide or a rhenium-containing supported palladium catalyst.
When carrying out the process of the invention, the vinyl oxirane or solutions of vinyl oxirane are hydrogenated in a solvent which is inert under the reaction conditions in the presence of the catalysts to be used in the invention at temperatures generally of from -10.degree. to 100.degree. C., preferably from -5.degree. to 50.degree. C. and more preferably from 0.degree. to 30.degree. C. under a pressure of from 1 to 100 bar, preferably from 1 to 50 bar, in particular from 1 to 30 bar.
The process of the invention can be carried out without the use of solvents or, advantageously, in the presence of a solvent inert under the reaction conditions, for example, in the presence of alcohols, such as methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol or tert-butanol, hydrocarbons, such as petroleum ether, benzene, toluene or xylene, or dipolar-aprotic solvents, such as N-alkyllactams, eg N-methylpyrrolidone or N-octylpyrrolidone, or, in particular, ethers, such as tetrahydrofuran, dioxane, methyl-tert-butyl ether, di-butyl ether, dimethoxy ethane, diethyl ether or diisopropyl ether.
The process of the invention can be carried out either continuously or batchwise, in the gas phase or in the liquid phase. When the process is carried out continuously, tubular reactors or cascades of reactors can be used for example, which can be operated in the upward-flow mode or downward-flow mode.
Advantageously, the catalysts are arranged in these reactors in the form of a fixed bed. When the process is carried out batchwise, the catalyst can be used, eg, in stirred reactors in the form of a suspension or, advantageously, as a fixed bed, eg, when use is made of recycle reactors.
The palladium content of the catalysts which can be used in the invention is generally from 0.1 to 5 wt %, preferably from 0.3 to 3 wt % and more preferably from 0.5 to 2 wt %, calculated as Pd and based on the total weight of the catalyst.
The rhenium-containing supported palladium catalysts which can be used in the invention contain rhenium in a ratio, by weight, in relation to palladium, generally of 1 to 99, preferably 10 to 90, and more preferably 40 to 60.
Apart from the support materials which can be advantageously used for the catalysts containing only palladium as active ingredient ie barium sulfate, zirconium dioxide, or titanium dioxide, other support materials, such as activated charcoal, silicon dioxide, silica gel, or kieselguhr can also be used to advantage.
The preparation of the palladium catalysts or the catalysts containing palladium and rhenium can be effected in conventional manner, for example, by impregnating the support materials with aqueous solutions of water-soluble compounds of palladium or of palladium and rhenium, for example, with the nitrates, sulfates, halides, or carboxylates of palladium and rhenium, drying the impregnated supports, eg, at temperatures of from 50.degree. to 200.degree. C., preferably from 100.degree. to 150.degree. C., then effecting calcination

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