Patent GB-474465-A (GB)
Title: A process for the preparation of condensation products
IPC: C08G8/30
Filed: 1936-05-21
Abstract: Condensation products are prepared by reacting phenols (such as phenol, cresols, naphthols, polyhydroxybenzenes or alkoxyphenols) with halogen compounds obtained from halogens or hydrogen halides and terpenes or derivatives thereof or acyclic compounds which can easily be converted into alicyclic compounds, such as the olefinic terpenes or terpenogenes or those compounds of indefinite nature which are formed from terpene compounds of high molecular weight, such as natural resins, especially copals, by a simple treatment, for example, by heating, the reaction being effected in the presence of halides of the metals aluminium, zinc or iron or substances which form the same under the reaction conditions, such as zinc dust. Suitable substances include borneol, pinene, limonene, terpineol, terpene hydrate, sesquiterpenes, cadinene, cedrene, resin acids, resin alcohols, isoprene, geraniol, citral, and readily available materials such as oil of bergamot, lemon-grass oil, oil of turpentine, technical dipentenes, camphor, oil of camphor, cumin oil, conifer oils, pine oil, colophony, neutral natural soft resins, tall oil, and resin oils.  Soft or even oily products are obtained when a small amount of phenol is used and with larger amounts harder and sometimes crystalline bodies are obtained, but soft products may be converted into hard by heating.  In examples: (1) technical dipentene that has been saturated with hydrogen chloride is condensed with phenol in the presence of aluminium chloride to yield a crystalline dihydroxydiphenylmenthane which is converted on heating into a resinous product that has a polymerization-delaying action on drying oils; (2) dipentene hydrochloride is condensed with o-cresol or guaiacol in the presence of zinc chloride; (3) American oil of turpentine treated with hydrogen chloride is separated by steaming into the isomeric bornyl chlorides and each isomer is condensed with phenol; (4) a mixture of m- and p-cresol p  is condensed with dipentene hydrochlorides in the presence of aluminium chloride; (5) American pine oil treated with hydrogen chloride is condensed with phenol in the presence of zinc chloride, excess phenol in the product being removed or alkylated by tert-butyl chloride; (6) cumin oil treated with hydrogen chloride is condensed with phenol in the presence of zinc chloride; (7) geraniol treated with hydrogen chloride is condensed with phenol in the presence of one of the specified catalysts; (8) a mixture of xylenol and American root extraction rosin is treated with hydrogen chloride and then condensed in the presence of aluminium or zinc chloride; (9) a chlorinated dipentene dihydrochloride is condensed with phenol in the presence of aluminium or zinc chloride, excess phenol being, if desired, converted into derivatives as by treatment with methyl butyl ketone, ethyl propyl ketone, acetone, cyclohexanone or methyl cyclohexanone; (10) a mixture of phenol and dipentene is treated with a small amount of hydrogen chloride or tert-amyl chloride and then condensed in the presence of zinc chloride; (11) a mixture of phenol and copal oil is treated with hydrogen chloride and then condensed in the presence of zinc chloride.