Patent GB-1084433-A (GB)
Title: Manufacture of biphenols
IPC: C07C39/15
Filed: 1964-08-28
Abstract: The new compounds 2,21,6,61-tetraphenyl-p,p1-diphenol and 2,21-diphenyl-p,p1-diphenol (see Division C2) are used as components in the manufacture of polycarbonate, polyester and polyepoxide resins by the known methods for making such resins, of which methods various details are given.  The polyesters are those of aromatic dicarboxylic acid, e.g. ortho-, iso- or tere-phthalic acids.ALSO:A phenol, which may be substituted in one or two of the 2-, 4- and 6-positions with one or two alkyl, alkoxy, aryl or aryloxy groups, is reacted in the liquid phase with a diphenoquinone (cf. Specification 930,993) carrying alkyl, alkoxy, aryl or aryloxy substituents in the 3-, 31-, 5- and 51-positions, whereby biphenols or mixtures of biphenols are obtained. A typical reaction is <FORM:1084433/C2/1> in which R and R1 are substituents, as defined above.  The reaction may be effected in the presence of an acid or basic catalyst, pyridine and homologous bases being the preferred catalysts.  A solvent may also be present, and this may be an excess of the phenol.  The reaction may be effected at atmospheric pressure at a temperature from 100 DEG  C. up to the reflux temperature.  Alternatively, the reaction may be effected in a sealed tube.  The biphenols produced in the reaction may be dealkylated, if desired.  In typical examples: (1) 2,6-di-t-butyl-phenol and 3,31,5,51-tetra-t-butyldiphenoquinone yield 2,21,6,61-tetra-t-butyl-p,p1-biphenol, (2) phenol and 3,31,5,51-tetra-t-butyldiphenoquinone yield a mixture containing p,p1, o,p1- and o,o1-biphenols and 2,21,6, 61-tetra - t - butyl - p,p1 - biphenol, (3) 2,6 - diphenylphenol and 3,31,5,51 - tetraphenyldiphenoquinone yield 2,21,6,61 - tetraphenyl-p, p1-biphenol, the purification of which by way of the diacetate (by treatment with acetic anhydride) is described, (4) 2-t-butyl-6-phenyl-phenol and 3,31-di-t-butyl-5,51-diphenyldiphenoquinone yield 2,21-di-t-butyl-6,61-diphenyl-p, p1-biphenol, which is then dealkylated by treatment with aluminium phenoxide or isopropoxide to yield 2,21-diphenyl-p,p1-biphenol, which is purified by way of its diacetate (by treatment with acetic anhydride), and (5) the product of Example 1 is dealkylated by treatment with aluminium isopropoxide to yield p,p1-biphenol.  The use of 2,21,6,61 - tetraphenyl - p,p1 - biphenol in the manufacture of polycarbonate, polyester and epoxy resins is described (see Division C3). Examples are given also of the preparation of the following intermediates.  2 - t - Butyl - 6 - phenylphenol is prepared from o-phenylphenol and isobutylene in the presence of aluminium o-phenylphenoxide. 2 - t - Butyl - 6 - methylphenol and 2,6 - di - t-butylphenol are prepared similarly. 3,31 - Di - t - butyl - 5,51 - diphenyldiphenoquinone is prepared from 2-t-butyl-6-phenyl-phenol by treatment with oxygen in the presence of cuprous chloride and tetramethylethylene diamine. 3,31,5,51-Tetra-t-butyldiphenoquinone is prepared similarly.  3,31 - Di - t - butyl - 5,51 - dimethyldiphenoquinone is prepared from 2-t-butyl-6-methylphenol by treatment with oxygen in the presence of cuprous chloride and dimethylacetamide or pyridine.