Patent GB-627918-A (GB)
Title: Nitrogen containing derivatives of 3-pentadecyl phenol
Filed: 1947-07-30
Abstract: 4-Amino-3-pentadecylphenol and its salts may be used as antioxidants in lubricating oils, cutting oils and petrol. Specification 627,927 is referred to.ALSO:4-Amino-3-pentadecylphenol and its salts may be used as: (1) antioxidants for rubbery copolymers of butadiene and acrylonitrile or styrene; (2) intermediates for the production of synthetic resins by (a) condensation with aldehydes or ketones in the presence of an acid catalyst, and (b) condensation with dihalides under alkaline conditions for the production of long chain ether-amine polymers and with trihalides for the production of thermosetting cross polymers.  Specification 627,927 is referred to.ALSO:4-Amino-3-pentadecylphenol is manufactured by reducing an azo compound produced by coupling 3-pentadecylphenol (or hydrogenated cardanol) with a diazotized aromatic amine, e.g. diazotized aniline or sulphanilic acid (see Group IV (c)).  The reduction may be effected by means of chemical reducing agents (e.g. sodium hydrosulphite, zinc and hydrochloric acid, or stannous chloride), or by catalytic hydrogenation (e.g. by shaking a suspension of Raney nickel or palladium powder catalyst in a solution of the azo compound in an atmosphere of hydrogen).  Depending on the pH of the system at the end of the reduction, the product will be present as the free aminophenol, an acid salt thereof or a metal phenolate, and it may be isolated in any of these forms, which are interconvertible by the action of acids (e.g. hydrochloric, sulphuric or phosphoric acid) and alkalies.  The products are useful as antioxidants, e.g. in paints, oils, aldehydes, divinyl ether anaesthetics, petrol and natural or synthetic rubber, and as photographic developers. 4-Amino-3-pentadecylphenol may also be diazotized and the diazonium salt treated with 80 per cent sulphuric acid to form 1 : 4-dihydroxy-3-pentadecylbenzene, with cuprous cyanide to form 4-cyano-3-pentadecylphenol, which may be hydrolysed to the corresponding carboxylic acid, or with potassium cyanate in glacial acetic acid to produce substituted ureas. Specification 627,927 is referred to.ALSO:Azo dyes are manufactured by (a) coupling 3-pentadecylphenol (or hydrogenated cardanol) with a diazotized aromatic amine (e.g. aniline, sulphamilic acid, o-, m- or p-toluidine, dianisidine, a nitroaniline, an anisidine, a phenylenediamine, a chloro-, bromo- or iodo-aniline, a -or b -naphthylamine, a naphthylaminesulphonic acid or 4-amino-3-pentadecylphenol), under weakly acid, neutral or preferably alkaline conditions (e.g. in the presence of an alkali metal hydroxide); or (b) diazotizing 4-amino-3-pentadecylphenol (see Group IV (b)) and coupling with dye intermediates such as H-, J- or K-acid. Examples of process (a) are given.  Specification 627,927 is referred to.ALSO:4-Amino-3-pentadecylphenol and its salts may be used as antioxidants in natural rubber and rubbery polymers of butadiene. Specification 627,927, [Group IV (b)], is referred to.ALSO:Divinyl ether anaesthetics are protected against oxidation by the addition of 4-amino - 3 - pentadecylphenol.  Specification 627,927 is referred to.