Patent GB-796508-A (GB)
Title: A process for the reaction of organic compounds containing hydroxyl groups with ethylene oxide
IPC: C08G65/28
Filed: 1955-08-31
Abstract: Hydroxy ethyl ethers are prepared by reacting ethylene oxide with an organic compound which contains at least one alcoholic hydroxy group and is free of aliphatic unsaturation, in the presence of at least 0.05 per cent by weight of antimony pentachloride based on the weight of organic hydroxy compound. The reaction is preferably effected at temperatures from about 60 DEG  C. upwards under atmospheric or elevated pressure using 0.1 to 1 per cent of catalyst.  The organic hydroxy compounds utilizable include mono-and poly-hydric alcohols, amino-alcohols, carboxylic acid alkylol amides, partial esters of carboxylic acids with polyhydric alcohols, and partial ethers of polyhydric alcohols including partial ethers of phenols with polyhydric alcohols.  The hydroxy compounds may contain from 1 to 30 or more carbon atoms and may be saturated aliphatic, cycloaliphatic or aromatic in nature; the alcohols are preferably primary or secondary.  The amount of ethylene oxide used may vary.  Reaction between lower hydroxy compounds and 1-4 mols. of ethylene oxide yields ethers useful as solvents.  Lower and higher alcohols reacted with 4-30 mols. of ethylene oxide yield polyethers useful as hydraulic liquids, surfaceactive materials and glycerine substitutes. Larger quantities of ethylene oxide may be used to obtain resins (see Group IV (a)).  Examples describe the reaction of the following compounds with various amounts of ethylene oxide at 100-130 DEG  C. under atmospheric or raised pressure to yield mixtures of ethers comprising generally mono- and poly-(up to tetra) glycol ethers but also higher polyethers: (1) lauryl alcohol, (4) n-octyl alcohol, (5) sec. C7 alcohols from cracked olefines, (6) stearyl alcohol, (7) alcohols obtained by reduction of coconut fatty acids, (8) n-decanol, (9) ethylene chlorhydrin, (10) glycerol, (11) ethylene glycol, (12) n-butanol, (13) monoethanol amine and (14) 2-phenyl ethanol.  In (11) the product obtained with 5 mols. ethylene oxide is reacted in stages with more ethylene oxide to form higher polyethoxy ethers. Examples (5) and (7) include comparative experiments using sodium methylate as catalyst.ALSO:Polyoxyethylene ethers are prepared by reacting ethylene oxide with an organic compound containing at least one alcoholic hydroxy group and which is free from aliphatic unsaturation, in the presence of at least 0.05 per cent by weight of hydroxy compound, as catalyst.  By using sufficient ethylene oxide, wax-like to resin-like compounds may be obtained having molar weights of up to 4000-12,000.  The hydroxy compounds may be mono- or polyhydric alcohols, amino-alcohols, carboxylic acid alkylol amides, partial esters of carboxylic acids with polyhydric alcohols and partial ethers of polyhydric alcohols, e.g. partial phenol ethers thereof, and may contain from 1-30 or more carbon atoms and be saturated aliphatic, cycloaliphatic or aromatic in structure. Reaction may be effected at 60 DEG  C. or higher under ordinary or raised pressure using up to 30 mols. or more of ethylene oxide per mol. of hydroxy compound.  In examples, higher polyglycol ethers are obtained from (6) stearyl alcohol and 6.6 mols. ethylene oxide; (7) alcohols obtained by reduction of coconut fatty acids and 7-8 mols. ethylene oxide; (9) ethylene chlorhydrin and 12 mols. ethylene oxide; (10) glycerol and 6.6 mols. ethylene oxide; (11) ethylene glycol and amounts of ethylene oxide added in stages to give products of M.W. from 284 up to 1096; and (13) monoethanolamine and 6.7 mols. ethylene oxide.  Lauryl alcohol, n-octyl alcohol, mixed C7 sec.-alcohols, n-decanol, n-butanol and 2-phenyl-ethanol are other specified hydroxylic reagents which are used in further examples to obtain low M.W. mono- and poly-ethoxy ethers (see Group IV(b)).  Example 7 includes a comparative experiment using sodium methylate as catalyst.