Patent GB-766771-A (GB)
Title: Process for the manufacture of epoxide compounds
IPC: C07D301/30
Filed: 1953-08-24
Abstract: Synthetic resins containing epoxide groups are made by reacting a salt of a polybasic organic acid with an epoxide containing replaceable halogen at an elevated temperature and at a pressure which exceeds atmospheric pressure by an amount equal at least to the pressure of said epoxide at said temperature.  Specified acids are oxalic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, dichlorosuccinic, nitrilotriacetic, thiodiglycollic, maleic, fumaric, citraconic, itaconic, mesaconic, phthalic, isophthalic, terephthalic, mellitic, pyromellitic, naphthalic, 2 : 6-naphthylene dicarboxylic, tetrachlorphthalic, cyanuric, diphenyl - o - o1- dicarboxylic, diphenyl - p - p1-dicarboxylic, ethylene glycol bis(p-carboxy phenyl)ether, trimethylene and tetramethylene glycol-(p-carboxy phenyl)ether and beta-bis-(p-carboxy phenyl)ethane. Also salts of polyesters derived from these acids and glycol, glycerine, pentaerythritol or mannitol may be used.  Specified salts are the lithium, potassium and sodium salts.  Specified halo-epoxy compounds are epichlorhydrin, epibromhydrin and 1-chlor-3 : 4-epoxy butane.  Reaction is preferably effected at 115-180 DEG  C. and 5-50 atmos., and may be effected in presence of a solvent (e.g. dioxan) or a small amount of water.  In examples, resins are made by reacting epichlorhydrin with (1)-(4) dipotassium phthalate, the resin of Example (1) being soluble in acetone, methylene chloride and ethyl acetate; (5) disodium phthalate; (6) dipotassium adipate; (7) dipotassium maleate; (8) the potassium salt of poly-1 : 4-butanediol phthalate; (9) the potassium salt of poly-1 : 4-butanediol adipate; (10) disodium adipate; (11) dipotassium phthalate and glycerine-alpha-gamma-dichlorhydrin (12) the reaction product of dipotassium phthalate with glycerine-alpha-gamma dichlorhydrin; and (13) dipotassium terepthalate.ALSO:Compounds containing epoxide groups are made by reacting a salt of a polybasic organic acid with an epoxide containing replaceable halogen at an elevated temperature and at a pressure which exceeds atmospheric by an amount equal at least to the pressure of said epoxide at said temperature.  Specified acids are oxalic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, dichlorosuccinic, nitrilotriacetic, thiodiglycollic, maleic, fumaric, citraconic, itaconic, mesaconic, phthalic, isophthalic, terephthalic, mellitic, pyromellitic, naphthalic, 2 : 6 - naphthalene dicarboxylic, tetrachlorophthalic, cyanuric, diphenyl-o-o1-dicarboxylic, diphenyl - p - p1 - dicarboxylic, ethylene glycol bis-(p-carboxy phenyl) ether, trimethylene and tetramethylene glycol bis-(p-carboxy phenyl) ether and beta-bis-(p-carboxy phenyl) ethane.  Specified salts are the lithium, potassium and sodium salts.  Specified halo-epoxy compounds are epichlorhydrin, epibromhydrin and 1 - chlor - 3 : 4 - epoxy butane.  Reaction is preferably effected at 115-180 DEG  C. and 5-50 atmos., and may be effected in presence of a solvent (e.g. dioxan) or a small amount of water.  Formul  are given of monomeric compounds obtainable from salts of phthalic acid and epichlorhydrin.  Other products obtained are resinous (see Group IV (a)).