Process for the preparation of a tetraalkycyclobutane-1,3-diol using a promoted-copper catalyst
AssigneeEastman Chemical Company
InventorsJennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Jr., Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
Life of this patent
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Abstract
The present disclosure relates to the production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a promoted copper-based catalyst.
Claims32
A process for producing a 2,2,4,4-tetraalkylcyclobutane-1,3-diol of Formula II, comprising contacting a 2,2,4,4-tetraalkylcyclobutane-1,3-dione with hydrogen in the presence of a promoted copper-based catalyst under conditions of temperature and pressure sufficient to form a 2,2,4,4-tetraalkylcyclobutane-1,3-diol,
- wherein each of the alkyl radicals R1, R2, R3 and R4 has, independently from each other, 1 to 8 carbon atoms and wherein the promoted copper-based catalyst comprises a silica support and wherein the promoter metal is chosen from cobalt or a Group 1 metal.
A process for producing 2,2,4,4-tetramethylcyclobutane-1,3-diol, comprising contacting 2,2,4,4-tetramethylcyclobutane-1,3-dione, a promoted copper-based catalyst comprising a silica support, a non-protic solvent, and hydrogen in a hydrogenation zone under conditions of temperature and pressure sufficient to form 2,2,4,4-tetramethylcyclobutane-1,3-diol support wherein the promoter metal is chosen from cobalt or a Group 1 metal.
A process for producing 2,2,4,4-tetramethylcyclobutane-1,3-diol comprising:
- (a) feeding isobutyric anhydride to a pyrolysis zone, wherein the isobutyric anhydride is heated at a temperature of 350° C. to 600° C. to produce a vapor effluent comprising dimethylketene, isobutyric acid, and unreacted isobutyric anhydride;
- (b) cooling the vapor effluent to condense isobutyric acid and isobutyric anhydride and separating the condensate from the dimethylketene vapor;
- (c) feeding the dimethylketene vapor to an absorption zone, wherein the dimethylketene vapor is contacted with a solvent comprising an ester containing 4 to 20 carbon atoms to produce an absorption zone effluent comprising a solution of dimethylketene in the solvent;
- wherein the ester comprises residues of an aliphatic carboxylic acid and an alkanol;
- (d) feeding the absorption zone effluent to a dimerization zone wherein the effluent is heated at a temperature of from 70° C. to 140° C. to convert dimethylketene to 2,2,4,4-tetramethylcyclobutane-1,3-dione to produce a dimerization zone effluent comprising a solution of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the solvent;
- and
- (e) contacting the 2,2,4,4-tetramethylcyclobutane-1,3-dione with hydrogen in the presence of a promoted copper-based catalyst comprising a silica support under conditions of temperature and pressure sufficient to form a 2,2,4,4-tetramethylcyclobutane-1,3-diol,
- wherein the promoter metal is chosen from cobalt or a Group 1 metal.
A process for producing a 2,2,4,4-tetraalkylcyclobutane-1,3-diol of Formula II, comprising contacting a 2,2,4,4-tetraalkylcyclobutane-1,3-dione with hydrogen in the presence of a promoted copper-based catalyst under conditions of temperature and pressure sufficient to form a 2,2,4,4-tetraalkylcyclobutane-1,3-diol,
- wherein each of the alkyl radicals R1, R2, R3 and R4 has, independently from each other, 1 to 8 carbon atoms and wherein the promoted copper-based catalyst comprises a zinc oxide support.
A process for producing 2,2,4,4-tetramethylcyclobutane-1,3-diol, comprising contacting 2,2,4,4-tetramethylcyclobutane-1,3-dione, a promoted copper-based catalyst comprising a zinc oxide support, a non-protic solvent, and hydrogen in a hydrogenation zone under conditions of temperature and pressure sufficient to form 2,2,4,4-tetramethylcyclobutane-1,3-diol.
A process for producing 2,2,4,4-tetramethylcyclobutane-1,3-diol comprising:
- (a) feeding isobutyric anhydride to a pyrolysis zone, wherein the isobutyric anhydride is heated at a temperature of 350° C. to 600° C. to produce a vapor effluent comprising dimethylketene, isobutyric acid, and unreacted isobutyric anhydride;
- (b) cooling the vapor effluent to condense isobutyric acid and isobutyric anhydride and separating the condensate from the dimethylketene vapor;
- (c) feeding the dimethylketene vapor to an absorption zone, wherein the dimethylketene vapor is contacted with a solvent comprising an ester containing 4 to 20 carbon atoms to produce an absorption zone effluent comprising a solution of dimethylketene in the solvent;
- wherein the ester comprises residues of an aliphatic carboxylic acid and an alkanol;
- (d) feeding the absorption zone effluent to a dimerization zone wherein the effluent is heated at a temperature of from 70° C. to 140° C. to convert dimethylketene to 2,2,4,4-tetramethylcyclobutane-1,3-dione to produce a dimerization zone effluent comprising a solution of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the solvent;
- and
- (e) contacting the 2,2,4,4-tetramethylcyclobutane-1,3-dione with hydrogen in the presence of a promoted copper-based catalyst comprising a zinc oxide support under conditions of temperature and pressure sufficient to form a 2,2,4,4-tetramethylcyclobutane-1,3-diol.
A process for producing a 2,2,4,4-tetraalkylcyclobutane-1,3-diol of Formula II, comprising contacting a 2,2,4,4-tetraalkylcyclobutane-1,3-dione with hydrogen in the presence of a promoted copper-based catalyst under conditions of temperature and pressure sufficient to form a 2,2,4,4-tetraalkylcyclobutane-1,3-diol,
- wherein each of the alkyl radicals R1, R2, R3 and R4 has, independently from each other, 1 to 8 carbon atoms and wherein the promoted copper-based catalyst comprises a barium chromate support, and
- wherein the 2,2,4,4-tetramethylcyclobutane-1,3-diol has a cis/trans molar ratio greater than about 0.5.
A process for producing 2,2,4,4-tetramethylcyclobutane-1,3-diol, comprising contacting 2,2,4,4-tetramethylcyclobutane-1,3-dione, a promoted copper-based catalyst comprising a barium chromate support, a non-protic solvent, and hydrogen in a hydrogenation zone under conditions of temperature and pressure sufficient to form 2,2,4,4-tetramethylcyclobutane-1,3-diol and
- wherein the 2,2,4,4-tetramethylcyclobutane-1,3-diol has a cis/trans molar ratio greater than about 0.5.
A process for producing 2,2,4,4-tetramethylcyclobutane-1,3-diol comprising:
- (a) feeding isobutyric anhydride to a pyrolysis zone, wherein the isobutyric anhydride is heated at a temperature of 350° C. to 600° C. to produce a vapor effluent comprising dimethylketene, isobutyric acid, and unreacted isobutyric anhydride;
- (b) cooling the vapor effluent to condense isobutyric acid and isobutyric anhydride and separating the condensate from the dimethylketene vapor;
- (c) feeding the dimethylketene vapor to an absorption zone, wherein the dimethylketene vapor is contacted with a solvent comprising an ester containing 4 to 20 carbon atoms to produce an absorption zone effluent comprising a solution of dimethylketene in the solvent;
- wherein the ester comprises residues of an aliphatic carboxylic acid and an alkanol;
- (d) feeding the absorption zone effluent to a dimerization zone wherein the effluent is heated at a temperature of from 70° C. to 140° C. to convert dimethylketene to 2,2,4,4-tetramethylcyclobutane-1,3-dione to produce a dimerization zone effluent comprising a solution of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the solvent;
- and
- (e) contacting the 2,2,4,4-tetramethylcyclobutane-1,3-dione with hydrogen in the presence of a promoted copper-based catalyst comprising a barium chromate support under conditions of temperature and pressure sufficient to form a 2,2,4,4-tetramethylcyclobutane-1,3-diol and
- wherein the 2,2,4,4-tetramethylcyclobutane-1,3-diol has a cis/trans molar ratio greater than about 0.5.
Dependencies are inferred from the claim text.