Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1986-07-21
1988-06-14
Evans, J. E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
549326, C07C 29136, C07C 3120
Patent
active
047513349
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a process for the production of butane-1,4-diol, more particularly to a process for the production of butane-1,4-diol by hydrogenolysis of a dialkyl ester, usually a di-(C.sub.1 to C.sub.4 alkyl) ester, of a C.sub.4 dicarboxylic acid, such as maleic acid, fumaric acid, or succinic acid.
Butane-1,4-diol is used as a monomer in the production of plastics such as polybutylene terephthalate. It is also used as an intermediate for manufacture of butyrolactone and of the important solvent, tetrahydrofuran.
The most commonly adopted present method of manufacturing butane-1,4-diol involves reacting acetylene and formaldehyde by the Reppe reaction to give but-2-yne-1,4-diol which is then hydrogenated to form butane-1,4-diol.
Alternatively it has been proposed in EP-B-0018163 to react allyl alcohol, which can be produced from propylene, with iso-butylene to form allyl t-butyl ether. This compound is then hydroformylated using, for example a rhodium complex hydroformylaton catalyst, to give 4-t-butoxybutyraldehyde, which is then hydrogenated and cleaved under mild conditions with the aid of an acid catalyst to give butane-1,4-diol and iso-butylene which is recycled for reaction with further allyl alcohol.
There have also been a number of proposals to produce butane-1,4-diol from maleic anhydride. According to these proposals maleic anhydride, which is produced by oxidation of butane or benzene, is esterified to give a diester of maleic acid which is then hydrogenated in one or more stages to give butane-1,4-diol. Alternatively it is proposed that, maleic acid or anhydride should be directly hydrogenated. In some of these proposals butyrolactone is an intermediate product.
U.S. Pat. No. 4,001,282 describes a process for production of butyrolactone by passing vaporised maleic acid, maleic anhydride, or a mixture thereof together with water and hydrogen over a metallic catalyst capable of hydrogenolysing a carboxylic group to a hydroxymethyl group. Typical catalysts include copper-zinc catalysts (such as Girdler G-66 ARS and G-66-BRS) and copper chromite catalysts (such as Girdler G-13). Besides butyrolactone the reported products include succinic acid anhydride, propionic acid, butyric acid, propanol and n-butanol, but no mention is made of butane-1,4-diol.
U.S. Pat. No. 4,048,196 teaches production of butane-1,4-diol and/or tetrahydrofuran by multi-stage catalytic hydrogenaton of maleic anhydride or succinic anhydride. In a first liquid phase hydrogenation step maleic anhydride or succinic anhydride is hydrogenated over a nickel catalyst to give butyrolactone. This is then hydrogenated in the liquid phase over a copper/zinc oxide or hydroxide catalyst to give butane-1,4-diol and tetrahydrofuran.
In U.S. Pat. No. 4,083,809, U.S. Pat. No. 4,105,674 and GB-A-1534136 there is described a process for producing butyrolactone using a Cu-Pd catalyst for vapour phase hydrogenation of maleic acid, succinic acid, their anhydrides, and mixtures of two or more thereof.
U.S. Pat. No. 2,079,414 describes use of copper chromite as a catalyst for effecting hydrogenation of esters. It is recommended that, in operating in the vapour phase, temperatures within the range of 300.degree. C. to 400.degree. should be used. Diethyl succinate is mentioned.
U.S. Pat. No. 2,040,944 recommends use of temperatures of 230.degree. to 400.degree. C. for hydrogenation of esters of non-aromatic polybasic acids with a monohydric aliphatic alcohol containing at least four carbon atoms. it recommends copper chromite as catalyst and teaches that the catalyst can be prepared by ignition of a copper ammonium chromate precipitate and used without further treatment or after reduction by hydrogen at a temperature of 500.degree. C. or higher. It goes on to mention that either the liquid phase or vapour phase can be used, depending largely upon the ester to be hydrogenated. Pressures of 100 to 250 bar are recommended, as well as use of about 5 to 20 moles of hydrogen per mole of ester. Example 1 describes a liquid phase batch reaction in
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Carter Anthony B.
Harris Norman
Kippax John W.
Rathmell Colin
Reason Arthur J.
Davy McKee (London) Limited
Evans J. E.
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