Patent GB-837980-A (GB)
Title: A process for the continuous preparation of epoxyalkyl esters of carboxylic acids
IPC: C07D303/16
Filed: 1957-05-10
Abstract: An epoxyalkyl ester is made continuously by passing a suspension of a salt of a carboxylic acid in an excess of an epoxyalkyl halide through a reaction tube having a diameter of about 0.7-3 cms. at a temperature of 80-200 DEG  C., and preferably at an increased pressure.  Specified salts are the lithium, sodium and potassium salts of acetic, propionic, valeric, caproic, caprylic, pelargonic, lauric, myristic, palmitic, stearic, oxalic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, dichlorosuccinic, nitrilotriacetic, thiodiglycolic, maleic, fumaric, citraconic, itaconic, mesaconic, benzoic, salicylic, phthalic, isophthalic, terephathalic, tetrahydrophthalic, mellitic, pyro-mellitic, naphthalic, 2,6-naphthalene dicarboxylic, tetrachlorophthalic, biphenyl-o,o1-dicarboxylic and biphenyl-p,p1-dicarboxylic acids. Specified epoxyalkyl halides are epichlorhydrin, epibromhydrin and 1-chloro-3,4-epoxybutane.  Reaction may be effected in the presence of an organic solvent (e.g. dioxan, acetone or methylethyl ketone) or a small amount of water.  Catalysts for the reaction are amines, quaternary ammonium compounds, Friedel-Crafts catalysts, and free carboxylic acids.  The carboxylic acid salts are preferably used in finely-divided form, e.g. by subjecting the suspension to mechanical or supersonic vibration or to high-speed stirrers, or by using the salt in spray-dried form.  Examples describe the manufacture of unspecified products from epichlorhydrin and (1) sodium benzoate; (2) the sodium salt of C8-C10 fatty acids; (3) disodium tetrahydrophthalate; (4) disodium phthalate; (5) a mixture of disodium phthalate and the sodium salts of C8-C10 fatty acids.ALSO:Synthetic resins containing epoxy groups are made continuously by passing a suspension of a salt of a carboxylic acid in an excess of an epoxyalkyl halide through a reaction tube having a diameter of about 0.7-3 cms. at a temperature of 80-200 DEG  C., and preferably at an increased pressure.  Specified salts are the lithium, sodium and potassium salts of acetic, propionic, valeric, caproic, caprylic, pelargonic, lauric, myristic, palmitic, stearic, oxalic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, dichlorosuccinic, nitrilotriacetic, thiodiglycolic, maleic, fumaric, citraconic, itaconic, mesaconic, benzoic, salicylic, phthalic, isophthalic, terephthalic, tetrahydrophthalic, mel litic, pyromellitic, naphthalic, 2.6-naphthalene dicarboxylic, tetrachlorophthalic, biphenyl-o-o1-dicarboxylic and biphenyl-p-p1-dicarboxylic.  Specified epoxyalkyl halides are epichlorhydrin, epibromhydrin and 1-chloro-3.4-epoxybutane. Reaction may be effected in the presence of an organic solvent (e.g. dioxan, acetone or methylethyl ketone) or a small amount of water.  Catalysts for the reaction are amines, quaternary ammonium compounds, Friedel-Crafts catalysts and free carboxylic acids.  The carboxylic acid salts are preferably used in a fine state of division, e.g. by subjecting the suspension to mechanical or supersonic vibration or to high-speed stirrers, or by using the salt in spray-dried form. Examples describe the manufacture of products from epichlorhydrin and (1) sodium benzoate; (2) the sodium salt of C8-C10 fatty acids; (3) disodium tetrahydrophthalate; (4) disodium phthalate; (5) a mixture of disodium phthalate and the sodium salts of C8-C10 fatty acids.