US 5,387,752 AGranted

Process for the production of cyclohexanedimethanol

AssigneeEastman Chemical Company

InventorsJohn Scarlett, Michael A. Wood, Colin Rathmell

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Abstract

A process is described for the production of cyclohexanedimethanol by hydrogenation of a dialkyl cyclohexanedicarboxylate which comprises: (a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst; (b) forming a vaporous feed stream of a hydrogen-containing gas,and a hydrogenatable material comprising a dialkyl cyclohexanedicarboxylate at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure in the range of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.90 bar), said vaporous feed stream having a known hydrogen-containing gas:dialkyl cyclohexanedicarboxylate ratio; (c) supplying the vaporous feed stream to the hydrogenation zone; (d) maintaining hydrogenation conditions in the hydrogenation zone which are effective to maintain the reaction mixture in contact with the hydrogenation catalyst above its dew point; (e) passing the vaporous feed stream through the hydrogenation zone; and (f) recovering from the hydrogenation zone a product stream containing cyclohexanedimethanol. In this process it is preferred to use dimethyl 1,4-cyclohexanedicarboxylate to produce 1,4-cyclohexanedimethanol.

Claims18

Dependent claims

A process for the production of cyclohexanedimethanol by hydrogenation of dialkyl cyclohexanedicarboxylate which comprises:

(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst selected from copper-containing catalysts and Group VIII metal-containing catalysts;
(b) forming a vaporous feed stream of a hydrogen-containing gas and a hydrogenatable material comprising dialkyl cyclohexanedicarboxylate at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure in the range of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.90 bar), said vaporous feed stream having a known hydrogen-containing gas:dialkyl cyclohexanedicarboxylate ratio;
(c) supplying the vaporous feed stream to the hydrogenation zone;
(d) maintaining hydrogenation conditions in the hydrogenation zone which are effective to maintain the reaction mixture in contact with the hydrogenation catalyst above its dew point, said hydrogenation conditions comprising a temperature which is 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 about 2000 psia (about 137.90 bar);
(e) passing the vaporous feed stream through the hydrogenation zone:
and
(f) recovering from the hydrogenation zone a product stream comprising cyclohexanedimethanol;
wherein the dialkyl cyclohexanedicarboxylate is selected from di-(C.sub.1 to C.sub.4 alkyl) cyclohexanedicarboxylates.

5 more elements

A process for the production of 1,4-cyclohexanedimethanol by hydrogenation of dimethyl 1,4-cyclohexanedicarboxylate which comprises the steps of:

(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst 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) forming a vaporous feed stream of a hydrogen-containing gas and a hydrogenatable material comprising dimethyl 1,4-cyclohexanedicarboxylate at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure in the range of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.90 bar), said vaporous mixture having a known hydrogen-containing gas:dialkyl cyclohexanedicarboxylate ratio;
(c) supplying the vaporous feed stream to the hydrogenation zone;
(d) maintaining hydrogenation conditions in the hydrogenation zone which are effective to maintain the reaction mixture in contact with the catalyst above its dew point, said hydrogenation conditions comprising a temperature which is 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 about 2000 psia (about 137.90 bar);
(e) passing the vaporous feed stream through the hydrogenation zone;
and
(f) recovering from the hydrogenation zone a product stream comprising 1,4-cyclohexanedimethanol.

6 more elements

Dependencies are inferred from the claim text.