Patent GB-481557-A (GB)
Title: Manufacture of isocyclic compounds
Filed: 1936-06-05
Abstract: A polybasic mineral acid or halide or anhydride thereof or amidosulphonic acid is reacted with a compound having the formula R.O.X. wherein R is an aromatic radicle containing as substituent at least one aromatic, aliphatic-aromatic or straight chain aliphatic radicle with at least three carbon atoms and X is a hydroxyalkyl or polyhydroxyalkyl radicle.  The salts of the products with alkalies, ammonia or amines are dispersing agents. They may be used in association with phosphates, bleaching agents and washing agents.  In admixture with common salt or sodium sulphate pulverulent products are obtained.  In examples, chlorsulphonic acid is used to sulphonate diphenylmonoglycolether and an alkylphenylmonoglycolether prepared by condensing phenol with the chlorides of coconut oil acids and treating the product, after reduction with ethylenechlorhydrin. Butylphenylglycol ether, hexylphenyl - b  - hydroxypropylether, octadecylphenyl-b -hydroxypropylether, butylnaphthyl - b  : g  - dihydroxypropylether, benzylphenylglycolether and p - hydroxydiphenylglycerol ether are specified starting materials. Ethers derived from 1 : 12-octodecyleneglycol, sorbite and pentaerythrite are also mentioned.  Specification 452,577 is referred to.  Samples have been furnished under Sect. 2 (5) of products obtained by treating: (a) dodecylphenylglycolether with sulphuric acid, amidosulphonic acid and with phosphorus pentoxide followed by neutralization with caustic soda to give the sodium salts of the resulting acid esters; (b) p-butylphenylglycolether with chlorsulphonic acid, followed by neutralization with caustic soda. The Provisional Specification includes the treatment of the compounds having the formula R.O.X. wherein R is a hydroaromatic radicle which contains an aromatic, hydroaromatic aliphatic-aromatic or straight chain aliphatic radicle as substituent and mentions n-dodecylcyclohexylglycolether as a starting material.ALSO:A polybasic mineral acid or halide or anhydride thereof or amidosulphonic acid is reacted with a compound having the formula R.O.X wherein R is an aromatic radicle containing as substituent at least one aromatic, aliphatic-aromatic or straight chain aliphatic radicle with at least three carbon atoms and X is a hydroxyalkyl or polyhydroxyalkyl radicle.  The salts of the products with alkalies, ammonia or amines are wetting, foaming, cleansing and dispersing agents.  They may be used in association with phosphates, bleaching agents and washing agents.  In admixture with common salt or sodium sulphate pulverulent products are obtained.  In examples, chlorsulphonic acid, in the presence of ether is used to sulphonate diphenylmonoglycolether (prepared from ethylenechlorhydrin and p-oxydiphenyl) and an alkylphenylmonoglycolether prepared by condensing phenol with the chlorides of coconut oil acids and treating the product, after reduction with ethylenechlorhydrin. Butylphenylglycol ether, hexylphenyl-b  - hydroxypropylether, octadecylphenyl - b  - hydroxypropylether, butylnaphthyl - b :g  - dihydroxypropylether, benzylphenylglycolether and p-hydroxydiphenyl-glycerol ether are specified starting materials. Ethers derived from 1 : 12-octodecyleneglycol, sorbite and pentaerythrite are also mentioned.  Specification 452,577 is referred to.  Samples have been furnished under Sect. 2 (5) of products obtained by treating (a) dodecylphenylglycolether with sulphuric acid, amidosulphonic acid and with phosphorus pentoxide followed by neutralization with caustic soda to give the sodium salts of the resulting acid esters; (b) p-butylphenylglycolether with chlorsulphonic acid in either, followed by neutralization with caustic soda.  p-Butylphenylglycolether is prepared by condensing butyrylchloride with phenol, reducing and treating the product with ethylenechlorhydrin.  p-Dodecylphenylglycolether is prepared by condensing phenol with lauric acid in the presence of borontrifluoride, reducing and treating the product with ethylenechlorhydrin.  The Provisional Specification includes the treatment of the compounds having the formula R.O.X, wherein R is a hydroaromatic radicle which contains an aromatic, hydroaromatic, aliphatic-aromatic or straight chain aliphatic radicle as substituent and mentions n-dodecylcyclohexylglycolether as a starting material.