Process for the simultaneous co-production of 2,2,4,4-tetramethylcyclobutane-1,3-diol and 1,4-cyclohexanedimethanol
AssigneeEastman Chemical Company
InventorsJennifer Ellen McCusker, Jerome Leonard Stavinoha, Jr., Christopher Fletcher Tomlin, Michael Wayne Salyer
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Abstract
The present disclosure pertains to processes for the simultaneous co-production of 2,2,4,4-tetramethylcyclobutane-1,3-diol and 1,4-cyclohexanedimethanol by hydrogenation 2,2,4,4-tetramethylcyclobutane-1,3-dione and dimethylcyclohexane-1,4-dicarboxylate, respectively, under hydrogenation conditions of temperature and pressure.
Claims26
A process for the co-production of 2,2,4,4-tetramethylcyclobutane -1,3-diol and cyclohexanedimethanol comprising contacting a mixture comprising 2,2,4,4-tetramethylcyclobutane-1,3-dione and dimethylcyclohexanedicarboxylate with a copper-based catalyst in the presence of hydrogen under conditions of pressure ranciinci from about 2000 to about 6000 psig and temperature ranging from about 170 to about 210°C. to yield at least about 25 wt % of the 2,2,4,4-tetramethylcyclobutane-1,3-dione into 2,2,4,4-tetramethylcyclobutane-1,3-diol and at least about 30 wt % of the dimethylcyclohexanedicarboxylate into cyclohexanedimethanol.
A process comprising
- (1) feeding isobutyric anhydride to a pyrolysis zone to produce a vapor effluent comprising dimethylketene, isobutyric acid and unreacted isobutyric anhydride;
- (2) cooling the vapor effluent to condense isobutyric acid and isobutyric anhydride and separating the condensate from the dimethylketene vapor;
- (3) feeding the dimethylketene vapor to an absorption zone wherein the dimethylketene vapor is dissolved in a dimethylcyclohexanedicarboxylate to produce an effluent comprising a solution of dimethylketene in the dimethylcyclohexanedicarboxylate;
- (4) feeding the absorption zone effluent to a dimerization zone wherein the effluent is heated to convert dimethylketene to 2,2,4,4-tetramethylcyclobutane-1,3-dione to produce an effluent comprising a solution of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the dimethylcyclohexanedicarboxylate;
- and
- (5) contacting the 2,2,4,4-tetramethylcyclobutane-1,3-dione and dimethylcyclohexanedicarboxylate with hydrogen in the presence of a copper-based catalyst under conditions of temperature ranciinci from about 170 to about 210° C. and pressure ranging from about 2000 to about 6000 psig to yield about 25 wt % of 2,2,4,4-tetramethylcyclobutane-1,3-diol and about 30 wt % of cyclohexanedimethanol.
A process for the co-production of 2,2,4,4-tetramethylcyclobutane-1,3-diol and a second diol comprising contacting a mixture comprising 2,2,4,4-tetramethylcyclobutane-1,3-dione and reactive solvent with a copper-based catalyst in the presence of hydrogen under conditions of pressure ranging from about 2000 to about 6000 psig and temperature ranging from about 170 to about 210° C. to yield at least about 25 wt % of the 2,2,4,4-tetramethylcyclobutane-1,3-dione into 2,2,4,4-tetramethylcyclobutane-1,3-diol and at least about 30 wt % of the reactive solvent into the second diol.
Dependencies are inferred from the claim text.