Patent GB-444239-A (GB)
Title: Improvements in or relating to the manufacture of compounds of heteropolar constitution of high molecular weight
IPC: C07C309/08
Filed: 1934-06-15
Abstract: An aliphatic compound having an uninterrupted chain of at least six carbon atoms, and a terminal halogen atom and a terminal hydroxy group at opposite ends of the chain, is reacted (a) with an alkali salt of a monobasic fatty acid containing at least eight carbon atoms, whereby the halogen atom is eliminated, and with sulphuric acid, chlorosulphonic acid, or an alkylene oxide, whereby the hydroxy group is converted into a sulphuric ester or polyglycol ether group, or (b) with an alkali sulphite, whereby the halogen atom is replaced by a sulphonic group, and with a monobasic fatty acid containing at least eight carbon atoms, whereby the hydroxy group is esterified. The products, if soluble in water, are useful as wetting, dispersing and cleansing agents; the water-insoluble products are useful as greasing agents for leather and textiles or, in conjunction with soaps or other dispersing agents, as dispersing agents for fatty substances.  In the examples: (1) 6-chlorohexanol-1, prepared from hexane-1 : 6-diol and hydrochloric acid, is heated with sodium sulphite to yield 6-oxyhexane-1-sulphonic acid, which is then esterified with decylic or octoic acid; (2) 10-chlorodecanol-1, prepared from decane-1 : 10-diol and hydrochloric acid, is treated with ethylene oxide in the presence of sulphuric acid to yield a polyglycol ether of 10-chlorodecanol-1, which is then heated with the sodium salt of a fatty acid containing at least eight carbon atoms. The Specification as open to inspection under Sect. 91 describes generally the manufacture of compounds containing a hydrophobe and a hydrophile group by elimination of halogen and hydroxylic hydrogen from halogenated alcohols prepared from glycols containing more than four carbon atoms.  The specified hydrophile groups are the sulphonic group, the sulphuric ester group, ester groups of polybasic acids, glycol, glycerol, polyglycol and polyglycerol residues, neutralized amino groups, and residues of aromatic sulphonic acids; the specified hydrophobe groups are residues of fatty acids and fatty alcohols and of the analogous sulphur compounds; the products may apparently contain any of the specified hydrophile groups in association with any of the specified hydrophobe groups.  An example is given in which 10-chlorodecanol-1 is heated with dodecyl mercaptan and caustic soda to yield 10-oxydecyldodecyl sulphide, which is then converted into a sulphuric ester by treatment with sulphuric or chlorosulphonic acid. This subject-matter does not appear in the Specification as accepted.ALSO:An aliphatic compound having an uninterrupted chain of at least six carbon atoms, and a terminal halogen atom and a terminal hydroxy group at opposite ends of the chain, is reacted (a) with an alkali salt of a monobasic fatty acid containing at least eight carbon atoms, whereby the halogen atom is eliminated, and with sulphuric acid, chlorosulphonic acid, or an alkylene oxide, whereby the hydroxy group is converted into a sulphuric ester or polyglycol ether group, or (b) with an alkali sulphite, whereby the halogen atom is replaced by a sulphonic group, and with a monobasic fatty acid containing at least eight carbon atoms, whereby the hydroxy group is esterified.  The products, if soluble in water are useful as dispersing agents; the water-insoluble products are useful, in conjunction with soaps or other dispersing agents, as dispersing agents for fatty substances.  In the examples: (1) 6-chloro-hexanol-1 is heated with sodium sulphite to yield 6-oxyhexane-1-sulphonic acid, which is then esterified with decylic or octoic acid; (2) 10-chlorodecanol-1 is treated with ethylene oxide in the presence of sulphuric acid to yield a polyglycol ether of 10-chlorodecanol-1, which is then heated with the sodium salt of a fatty acid containing at least eight carbon atoms.  The Specification as open to inspection under Sect. 91 describes generally the manufacture of compounds containing a hydrophobe and a hydrophile group by elimination of halogen and hydroxylic hydrogen from halogenated alcohols prepared from glycols containing more than four carbon atoms.  The specified hydrophile groups are the sulphonic group, the sulphuric ester group, ester groups of polybasic acids, glycol, glycerol, polyglycol and polyglycerol residues, neutralized amino groups, and residues of aromatic sulphonic acids; the specified hydrophobe groups are residues of fatty acids and fatty alcohols and of the analogous sulphur compounds; the products may apparently contain any of the specified hydrophile groups in association with any of the specified hydrophobe groups.  An example is given in which 10-chlorodecanol-1 is heated with dodecyl mercaptan and caustic soda to yield 10-oxydecyldodecyl sulphide, which is then converted into a sulphuric ester by treatment with sulphuric or chlorosulphonic acid.  This subject-matter does not appear in the Specification as accepted.