Process for the preparation of 1,4-cyclohexanedimethanol

A process for the preparation of 1,4-cyclohexanedimethanol, comprising:

• (i). feeding an esterification reaction product, comprising bis(4-methylcyclohexyl)methyl)terephthalate and (4-methylcyclohexyl)methanol, with hydrogen to a first hydrogenation zone comprising a fixed bed of a palladium on alumina catalyst at a temperature of about 180° C. to about 250° C. and a pressure of about 50 to about 170 bars gauge to produce a liquid effluent comprising bis(4-methylcyclohexyl)methyl cyclohexane-1,4-dicarboxylate;
• (ii). feeding the liquid effluent from step (i) with hydrogen to a second hydrogenation zone comprising a fixed bed comprising a copper chromite catalyst at a temperature of about 180 to about 300° C. and a pressure of about 100 to about 400 bars gauge to produce a hydrogenation product comprising 1,4-cyclohexanedimethanol, 4-methylcyclohexanemethanol, and 4,4′-oxybis(methylene)bis(methylcyclohexane);
• (iii). distilling the hydrogenation product from step (ii) 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;
• (iv). allowing the distillation bottoms to form a lower layer comprising a majority of the 1,4-cyclohexanedimethanol in the distillation bottoms and an upper layer comprising a majority of the 4,4′-oxybis(methylene)-bis(methylcyclohexane) in the distillation bottoms;
• (v). separating the upper and lower layers of step (iv) and recovering the 1,4-cyclohexanedimethanol from the lower layer by distillation;
• and
• (vi). passing the (4-methylcyclohexyl)methanol from the distillate in step (iii) to an esterification process to produce bis(4-methylcyclohexyl)methyl)terephthalate.