GB711122A - Improvements in or relating to the production of bis(hydroxyphenyl) compounds - Google Patents

Abstract

Bis (hydroxyphenyl) compounds are prepared by reacting phenolic compounds with carbonyl compounds in an aqueous acidic medium containing at least twice as much water by weight as phenolic compound. The products may be represented by the formula <FORM:0711122/IV (b)/1> where each R, which may be the same or different, is hydrogen or an alkyl, cycloalkyl, aryl, alkaryl or aralkyl radical. The phenolic radicals may be further substituted by similar radicals. Examples of carbonyl compounds are formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, n-valeraldehyde, trimethylacetaldehyde and benzaldehyde. In addition to phenol and alkyl substituted phenols, such compounds as o- and p - phenyl phenols, naphthols, phenanthrol, cresylic acid and compounds having more than one hydroxy group in the nucleus are mentioned. Examples of acidic catalysts are sulphuric, hydrochloric, acetic, p-toluene sulphonic, alkane sulphonic, phosphoric, sulphamic and hydrofluoric acids and boron trifluoride complexes. Emulsifying agents are preferably employed. The reaction temperature may be from 20 DEG to 150 DEG C. The products are obtained in a high state of purity as fine spheroidal particles which generally become smaller as the ratio of water to phenol is increased up to about 9. They may comprise isomeric forms of a compound, and when using two or more different phenolic compounds, the resulting mixture will contain proportions of compounds wherein two different phenolic radicals are attached to a single carbon atom. The process may be batch, continuous or semi-continuous, employing one or more reactors provided with stirrers. In the examples: bis-(3-tert.-butyl-5-methyl-2-hydroxyphenyl)-methane is prepared from tert.-butyl cresol and formaldehyde; bis-(4-hydroxyphenyl) methane from phenol and formaldehyde; bis-(3,4-dimethyl-2-hydroxy-phenyl) methane from 2,3-dimethyl-phenol and formaldehyde; 1,1-bis-(3-tert.-butyl-6-methyl-4-hydroxyphenyl) propane from 2-tert.-butyl-5-methyl-phenol and propionaldehyde; 1,1-bis-(3 - tert. - butyl - 5 - methyl - 4 - hydroxyphenyl) ethane from 2-methyl-6-tert.-butylphenol and acetaldehyde; bis-(3 - tert. - octyl - 6 - methyl-4 - hydroxyphenyl) methane from 2 - tert. - octyl - 5 - methylphenol and formaldehyde; bis - (3 - tert. - butyl - 6 - methyl - 4 - hydroxy-phenyl) benzylidene from 2 - tert. - butyl - 5 - methylphenol and benzaldehyde; and bis-(3-tert. - butyl - 5 - isopropyl - 2 - hydroxyphenyl) methane from 2-tert.-butyl-4-isopropylphenol and formaldehyde.