Patent GB-544402-A (GB)
Title: Improvements in or relating to the preparation of tetrahydrofurfuryl alcohol derivatives
IPC: C07D307/12
Filed: 1940-02-09
Abstract: 544,402. Emulsifying agents. COLGATEPALMOLIVE-PEET CO. Feb. 9, 1940, No. 2541. Convention date, Feb. 11, 1939. [Class 1 (i)] [Also in Group IV] Esters of'tetrahydrofurfuryl alcohol with aliphatic carboxylic acids, or ethers of tetrahydrofurfuryl alcohol with aliphatic alcohols or the components thereof are treated with sulphonating agents. In examples: (1) tetrahydrofurfuryl alcohol is treated with sulphuric acid and coconut oil lauric acid, caprylic acid and with myristic acid: (2) tetrahydrofurfuryl alcohol is etherified with coconut alcohols using the sodium salts of the acid sulphates of the latter and the product sulphonated, and neutralized. In the neutralization, the following may be used:-alkali metal hydroxides and carbonates, basic compounds of calcium, magnesium, mercury, ammonia, mono-, di- and tri-ethanolamines, mono-, di- and triglycerolamine, butylamine, amylamine, methylamine, aniline, nicotine, betaine, pyridine and piperidine. Instead of using sulphuric acid, sulphonation may be effected with, sulphurtrioxide, chlorsulphonic acid, amino sulphonic acid, sulphuryl chloride, ethylsulphuric acid, acetylsulphuric acid and other mono alkyl or acyl derivatives of sulphuric acid. Liquid sulphur dioxide, chloroform, ether, petroleum ether, ethylenedichloride, trichlorethylene, solid carbon dioxide, liquefied propane of butane may be used as diluents or refrigerants. For esterifying the tetrahydrofurfuryl alcohol, the following carboxylic acids and compounds yielding the same may be used; garbage grease, tallow, olive oil, castor oil, hardened fish oil, tall oil, palm oil, soyabean oil, naphthenic acid, abietic acid hydrogenated abietic acid, acids obtained by the oxidation of mineral oils and halogenated fatty acids. For etherification, dodecanol, benzyl alcohol, ceryl alcohol, cyclbhexanol, abietyl alcohol and hydrogenated abietyl alcohol may be used. The products are stated to have emulsifying properties and may be used in association with soaps, rosinates, higher alcohol sulphates, alkylated aromatic sulphonic acids, sulphonated mineral oil extracts, lecithin, glycerolamines, diethanolamine, triethanolamine soaps, glycerol amines, dyes, latex, pigments, abrasives, silica, pumice, feldspar, chalk, infusorial earth, bentonite, talc, starch, carbon tetrachloride, perchlorethylene, trichlorethylene, glycerine, tetrahydrofurfuryl alcohol, phenol, cyclohexanol, tetrahydronaphthalene, pine oil, mineral oils, perfumes, deodorants, fats, oils, fatty acids, monoglycerides, vitamin F,. waxes, gums, resins, phenyl mercury chloride, phenolmercury chloride, methysalicylate, mercurychloride, styptics, sodium sulphate, chloride, acetate, bicarbonate, hypochlorite, thiosulphate, hydrosulphate and hyposulphite and the corresponding ammonium and potassium salts, tetraphosphoric, pryophosphoric and hexametaphosphoric acids and their alkali, ammonium and amine salts and alkylesters. The products may be used in insecticides, cements, abrasives, antiseptics, water softeners, paints, polishes, adhesives, shellac and casein compositions, tooth and mouth detergents, blueing, bleaching, dyeing and discharging compositions, depilatories, dust preventers, fireextinguishing compositions, drain and radiator cleaners, anti-freezing, anti-fogging and anticorrosion compositions, wood impregnants, electrolytic baths, shampoos, fat liquors for leather, photographic solutions, paint and grease removers, dry-cleaners, de-emulsifying compositions. Specification 538,375, [Group IV], is referred to. The Specification as open to inspection under Sect. 91 includes also the .treatment of any saturated organic compound containing a butylene oxide ring with a mineral acid such as nitric or hydrochloric acid. Condensation with a mineral acid such as nitric or hydrochloric acid, a carboxylic acid, an alcohol or a phenol may also be effected. Tetrahydrofurfurylamine, tetrahydrofurfurylhalides, hydrogenated derivatives of the cyclic ethers prepared by dehydrating pentose, hexose, and higher aldehyde sugars and poly hydrogenated coumarone are specified starting materials. These may be used in association with alcohols, monoglycerides, polyglycerines, polyglycols, mannitol, erythritol, glyceric acid, pentandiol, pentantriol, napthalene, diphenyl and aromatic extracts from petroleum. In further examples, a residue obtained in the hydrogenation of furfural which contains 1 : 2-,1 : 5, and 1 : 2 : 5- pentane-di and triols is sulphonated. The chlorderivative of tetrahydrofurfurylalcobol may be treated with sodium sulphite or ammonia to obtain a sulphonate or ammo compound. The use of phosphating and borating agents is mentioned, together with esterification assistants such as acetic and propionic anhydride. This subjectmatter does not appear in the Specification as accepted.