Patent GB-440910-A (GB)
Title: Process for the manufacture of octylphenols and ethers thereof
IPC: C07C41/05
Filed: 1934-10-31
Abstract: Octylphenols and ethers thereof are obtained by treating a phenol having a free o- or p-position to the hydroxy group, or an ether of such a phenol, in the presence of sulphuric acid of more than 90 per cent strength, with a mixture of octenes boiling at 106--123 DEG  C., preferably 106--116 DEG  C., at normal pressure and obtained by polymerizing a butene mixture produced in cracking petroleum; an octene mixture of the boiling range specified is practically free from diisobutylene.  The process may be applied to mono- or poly-cyclic phenols (or their ethers), which may be substituted in the nucleus with halogen atoms or with alkyl, aryl, alkoxy, aryloxy, carboxy or nitro groups.  Examples are given in which phenol, o-, m- and p-cresol, resorcinol and anisole are condensed with the octene mixture.  Reference is made also to the treatment of b -naphthol, pyrocatechol, hydroquinone, xylenols, isopropylphenols, m-chlorophenol, salicylic acid, p-hydroxybenzoic acid, phenetole, guaiacol, and diphenyl ether. The products are useful as germicides and antiseptics in soaps and oils; as antioxidants in rubber, soaps, gasoline and vegetable oils; as materials for making resins by condensation with formaldehyde, furfural and other aldehydes; and as plasticizers for resinous compositions.ALSO:Octylphenols and ethers thereof, useful as germicides and antiseptics in soaps and oils, and as anti-oxidants in soaps, gasoline and vegetable oils, are obtained by treating a phenol having a free o- or p-position to the hydroxy group, or an ether of such a phenol, in the presence of sulphuric acid of more than 90 per cent strength, with a mixture of octenes boiling at 106--123 DEG  C., preferably 106--116 DEG  C., at normal pressure and obtained by polymerizing a butene mixture produced in cracking petroleum; an octene mixture of the boiling range specified is practically free from diisobutylene.  The process may be applied to mono- or poly-cyclic phenols (or their ethers), which may be substituted in the nucleus with halogen atoms or with alkyl, aryl, p alkoxy, aryloxy, carboxy or nitro groups.  Examples are given in which phenol, o-, m-and p-cresol, resorcinol and anisole are condensed with the octene mixture.  Reference is made also to the treatment of b -naphthol, pyrocatechol, hydroquinone, xylenols, isopropylphenols, m-chlorophenol, salicylic acid, p-hydroxybenzoic acid, phenetole, guaiacol, and diphenyl ether.ALSO:Octylphenols and ethers thereof, useful as anti-oxidants in rubber are obtained by treating a phenol having a free o- or p-position to the hydroxy group, or an ether of such a phenol, in the presence of sulphuric acid of more than 90 per cent strength, with a mixture of octenes boiling at 106-123 DEG  C., preferably 106-116 DEG  C., at normal pressure and obtained by polymerizing a butene mixture produced in cracking petroleum; an octene mixture of the boiling range specified is practically free from di-isobutylene.  The process may be applied to mono- or poly-cyclic phenols (or their ethers), which may be substituted in the nucleus with halogen atoms or with alkyl, aryl, alkoxy, aryloxy, carboxy or nitro groups.  Examples are given in which phenol, o-, m- and p-cresol, resorcinol and anisole are condensed with the octene mixture.  Reference is made also to the treatment of b -naphthol, pyrocatechol, hydroquinone, xylenols, isopropylphenols, m-chlorophenol, salicylic acid, p-hydroxybenzoic acid, phenetole, guaiacol, and diphenyl ether.ALSO:Octylphenols and ethers thereof, useful as germicides and antiseptics in soaps and oils, are obtained by treating a phenol having a free o- or p-position to the hydroxy group, or an ether of such a phenol, in the presence of sulphuric acid of more than 90 per cent strength, with a mixture of octenes boiling at 106-123 DEG  C., preferably 106-116 DEG C., at normal pressure and obtained by polymerizing a butene mixture produced in cracking petroleum; an octene mixture of the boiling range specified is practically free from diisobutylene.  The process may be applied to mono- or poly-cyclic phenols (or their ethers), which may be substituted in the nucleus with halogen atoms or with alkyl, aryl, alkoxy, aryloxy, carboxy or nitro groups.  Examples are given in which phenol, o-, m- and p-cresol, resorcinol and anisole are condensed with the octene mixture.  Reference is made also to the treatment of b -naphthol, pyrocatechol, hydroquinone, xylenols, isopropylphenols, m - chlorophenol, salicylic acid, p-hydroxybenzoic acid, phenetole, guaiacol, and diphenyl ether.