GB1449207A - Production of bis -hydroxyphenyl- alkanes - Google Patents

Abstract

1449207 Bis(hydroxyphenyl)alkanes MONSANTO AUSTRALIA Ltd 27 Dec 1973 [29 Dec 1972] 59773/73 Heading C2C The invention comprises a process for the production of bis(hydroxyphenyl)alkanes or bis(hydroxy substituted phenyl) alkanes by condensation of phenols with ketones of the formula R 1 COR 2 where R 1 and R 2 are alkyl, cycloalkyl of 5 or 6 carbon atoms, cycloalkyl substituted by halogen or alkyl of 1-6 carbon atoms, or phenyl or wherein R 1 and R 2 may together be cycloalkyl or substituted cycloalkyl as specified, in the presence of an acidic catalyst and a sulfur compound promoter or ketone precursor which is either a mercaptan of the structural formula (HS) n -R<SP>1</SP>-(X) n wherein R<SP>1</SP> is a saturated or unsaturated aliphatic hydrocarbon or aryl, X is selected from carboxyl, ester, sulfonyl, hydroxy, amino, substituted amino and salts thereof, and n is an integer from 1 to 3; or a corresponding mercaptal of the structural formula (R<SP>11</SP>CH(SR<SP>11</SP> <SP>1</SP>) 2 wherein R<SP>11</SP> conforms with R 1 and R 2 of the ketone structural formula specified above and R<SP>11</SP> <SP>1</SP> corresponds to the mercaptan structural formula specified above; or a corresponding mercaptole of the structural formula wherein R<SP>11</SP> and R<SP>11</SP> 1 are as specified above, which process comprises metering the ketone reactant into a mixture of the phenol reactant charge, acidic catalyst and sulfur compound promoter or ketone precursor in an azeotropic distillation entrainer medium at reflux temperature in a reactor equipped for azeotropic distillation, whereby water generated by reaction of the phenol and ketone is continuously removed from the reactor azeotropically to maintain the reaction mass under relatively anhydrous conditions, the metering of the ketone reactant into said reaction mixture being either continuous or intermittent and the addition rate of ketone reactant being substantially commensurate with the water of reaction removal rate from the reactor, said mixture of phenol reactant, acidic catalyst and sulfur compound promoter or ketone precursor in the reactor optionally containing a proportion of the charge of ketone reactant in amount not exceeding 0À25 mole per mole of phenol reactant and said metered ketone reactant optionally containing incremental acidic catalyst and/or incremental sulfur compound promoter or ketone precursor and/or incremental entrainer medium, the reaction being brought to the desired stage of completion by refluxing the reaction mass until the crystallization point of the end product in the entrainer medium is reached or an amount of water of reaction has been evolved which corresponds approximately with the theoretical amount generated by the charge of phenol and ketone reactants, and the end product recovered from the reaction mass.