US 5,395,990 A · Process for the production of alcohols and diols

Abstract

A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, aldehydes, olefinically unsaturated aldehydes, and mixtures of two or more thereof, which process comprises the steps of: (a) providing a hydrogenation zone containing a charge of a granular hydrogenation catalyst which has a total surface area of at least about 15 m.sup.2 /g, a pore size distribution such that more than 50% of the pore volume is provided by pores in the size range less than about 40 nm, and a surface area distribution such that more than 50% of the total surface area is provided by pores in the size range of from about 7 nm to about 40 nm; (b) supplying to the hydrogenation zone a feed stream of a mixture containing hydrogen and the hydrogenatable material; (c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of the hydrogenatable material; and (d) recovering from the hydrogenation zone a product stream comprising the hydroxylic compound. The process is exemplified by the hydrogenation of dimethyl 1,4-cyclohexanedicarboxylate to yield 1,4-cyclohexanedimethanol.

Claims21

Dependent claims

A process for the production of alcohols and diols by hydrogenation of a hydrogenatable material selected from C.sub.1 -C.sub.4 alkyl monoesters of C.sub.8 -C.sub.18 carboxylic acids, C.sub.1 -C.sub.4 alkyl monoesters of C.sub.4 -C.sub.9 dicarboxylic acids, di-C.sub.1 -C.sub.4 alkyl diesters of C.sub.4 -C.sub.9 dicarboxylic acids, lactones selected from gamma-butyrolactone and epsilon-caprolactone, aldehydes containing up to about 30 carbon atoms, 2-ethyl-hexen-2-al, 2-propylhept-2-enal, 4-methoxycarbonylcyclohexylcarboxaldehyde, and mixtures of two or more thereof, which process comprises the steps of:

(a) providing a hydrogenation zone containing a charge of a granular hydrogenation catalyst which has a total surface area of at least about 15 m.sup.2 /g, a pore size distribution such that more than 50% of the pore volume is provided by pores in the size range less than about 40 nm, and a surface area distribution such that more than 50% of the total surface area is provided by pores in the size range of from about 7 nm to about 40 nm and wherein the granular hydrogenation catalyst is selected from copper-containing catalysts and Group VIII metal-containing catalysts;
(b) supplying to the hydrogenation zone a feed stream of a mixture containing hydrogen and the hydrogenatable material;
(c) maintaining the hydrogenation zone at a temperature in the range of from about 150.degree. C. to about 350.degree. C. and a pressure in the range of from about 150 psia (about 10.34 bar) up to about 2000 psia (about 137.90 bar) to effect hydrogenation of the hydrogenatable material;
and
(d) recovering from the hydrogenation zone a product stream comprising the alcohol or diol.

2 more elements

A process for the production of cyclohexanedimethanol which comprises the steps of:

(a) providing a hydrogenation zone containing a charge of a granular hydrogenation catalyst which has a total surface area of at least about 40 m.sup.2 /g, a pore size distribution such that about 70% up to about 85% of the pore volume is provided by pores in the size range of from about 7 nm to about 40 nm, and a surface area distribution such that about 70% up to about 85% of the total surface area is provided by pores in the size range of from about 7 nm to about 40 nm, wherein not more than about 25% of the total surface area is provided by pores in the size range of about 3.7 nm to about 7 nm and wherein the granular hydrogenation catalyst is selected from reduced copper chromite catalysts wherein the Cu:Cr weight ratio is from about 0.1:1 to about 4:1;
reduced, copper chromite catalysts wherein the Cu:Cr weight ratio is from about 0.1:1 to about 4:1 promoted with from about 0.1% by weight up to 15% by weight of barium, manganese or a mixture of barium and manganese;
or reduced manganese promoted copper catalysts wherein the Cu:Mn weight ratio is from about 2:1 to about 10:1;
(b) supplying to the hydrogenation zone a feed stream of a mixture containing hydrogen and di-C.sub.1 -C.sub.4 alkyl cyclohexanedicarboxylate;
(c) maintaining the hydrogenation zone at a temperature of from about 150.degree. C. to about 350.degree. C. and a pressure of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.90 bar);
and
(d) recovering from the hydrogenation zone a product stream comprising cyclohexanedimethanol.

4 more elements

Dependencies are inferred from the claim text.

Process for the production of alcohols and diols

Life of this patent

Process for the production of alcohols and diols

Life of this patent

Abstract

Claims21