Patent ID: 8766017

Claim:
A process for the preparation of a 1,4-cyclohexanedimethanol from terephthalic acid, comprising: (i). contacting terephthalic acid and (4-methylcyclohexyl)methanol in a mole ratio of alcohol to acid of at least 2:1, in a reaction zone at a temperature of about 200° C. to about 300° C. under superatmospheric pressure, while removing water from the reaction zone, to form an esterification product mixture comprising bis(4-methylcyclohexyl)methyl) terephthalate and unreacted (4-methylcyclohexyl)methanol; (ii). contacting the esterification product mixture with hydrogen in a first hydrogenation zone in the presence of a catalyst effective for hydrogenation of an aromatic ring to produce a liquid effluent comprising bis(4-methylcyclohexyl)methyl)cyclohexane-1,4-dicarboxylate; (iii). contacting the effluent from the first hydrogenation zone with hydrogen in the presence of an ester hydrogenation catalyst in a second hydrogenation zone to produce a hydrogenation product comprising 1,4-cyclohexanedimethanol, 4,4′-oxybis(methylene)bis(methylcyclohexane), and (4-methylcyclohexyl)methanol; (iv). distilling the hydrogenation product from step (iii) to recover a distillate comprising a majority of the (4-methylcyclohexyl)methanol in the hydrogenation product and a distillation bottoms comprising a majority of the 1,4-cyclohexanedimethanol and 4,4′-oxybis(methylene)bis(methylcyclohexane) in the hydrogenation product; (v). allowing the distillation bottoms to form an lower layer comprising a majority of the 1,4-cyclohexanedimethanol in the distillation bottoms and a upper layer comprising a majority of the 4,4′-oxybis(methylene)-bis(methylcyclohexane) in the distillation bottoms; (vi). separating the upper and lower layers of step (v) and recovering the 1,4-cyclohexanedimethanol from the lower layer by distillation; and (vii). recycling at least a portion of the (4-methylcyclohexyl)methanol to step (i).