Patent GB-191104648-A (GB)
Title: Manufacture of New Compounds by the Action of Formaldehyde on Organic Bodies in Concentrated Sulphuric Acid.
Inventor: NAEF ERNEST EUGENE
IPC: C07B45/00
Filed: 1911-02-24
Granted: 1912-02-26
Abstract: 4648. Naef, E. E. Feb. 24. Samples furnished. Formaldehyde compounds containing sulphur are produced by condensing formaldehyde or its polymers or substances producing them, in the presence of concentrated or fuming sulphuric acid, with the following organic compounds: - hexanes, heptanes, octanes, benzene, toluene, xylene, cumene, and other hydrocarbons of the benzene series, naphthalene, anthracene, phenanthrene, alpha and #-nitro- and alpha-chlor-naphthalenes, alpha- and #-naphthalene sulphonic acids, carbazole, acstanilide, acet-o- and -p-toluidines, acet-p-phenetidine, p-aminoacetanilide, acet-alpha- and -#-naphthylamines, benzanilide, benzyltoluidine, alpha- and #-naphthylamines, phenyl-alpha- and -#-naphthylamines, benzyl- and benzoyl-alpha- and -#-naphthylamines, phenyl-1-naphthylamine - 8 - sulphonic acid, 2 - naphthylamine- 3 : 6-disulphonic acid, 1-naphthol-4- and - 5-sulphonic acids, 1-naphthol-3:6- and -3:8- disulphonic acids, 2-naphthol-6-sulphonic acid, 2-naphthol-3:6-, -6 : 8-, and -5:7-, disulphonic acids, 2:8:6- and 2:5:7-, 1:8:4-, and 8:1:4-, aminonaphtholsulphonic acids, 8:1:3:6- and 8 : 1 : 5 : 7 - aminonaphtholdisulphonic acids, 1: 8:3: 6-dioxynaphthalenedisulphonic acid, 1:2- and 2:1-oxynaphthoic acids, phenol, acetylphenol, phenolcarbonate, o- and p-chlorphenols and their methyl and ethyl ethers, ethyl. and methyl ethers of phenol, o- and p-phenolstilphonic acids and their alkyl ethers, phenol- and #-naphthol - benzoates, o- and p-nitrophenols, o-, m-, and p-cresols, their acetyl derivatives, their alkyl ethers, and their sulphonic acids, alpha- and #-naphtliols and their alkyl ethers and acetyl derivatives, thymol, carvacrol, guaiacol, methylguaiacol, guaiacol-p-sulphonic acid, diguaiacol, dioxybenzenes and their methyl and ethyl ethers, pyrogallic acid, gallic acid and its monomethyl and monoethyl ethers, gallamic acid, tannic acid, salicylic acid, phenylsalicylic acid, acetylsalicylic acid, methyl- and ethylsalicylic acids, cresotinic acids, isomers of salicylic acid and their alkyl derivatives, o-, m-, and p-aminophenols, o-methyl- and -ethylaminophenols, m - diethylaminophenol, 1:2- aminonaphthol, p - oxy - p<1> - dimethylaminodiphenylamine, p-oxy-p<1>-amino-o<1>-tolylphenylamine,p<1>-oxy-m<1>-tolyl-o:p-dinitrophenylamine,poxy - m - dinitrodiphenylamine, benzyl chloride, benzal chloride, urea, thiourea, phenyl-and diphenylureas, phenyl- and diphenyl-thioureas, guanidine, alpha-triphenylguanidine, phthalimide, antipyrine, saccharin, phenylhydrazine, 1-amino- and 1:2-diamino-anthraquinones, indigo and leucoindigo. The products obtained from 2- naphthol-6-sulphonic acid, 8:1:3:6-aminonaphtholdisulphonic acid, 1:2-oxynaphthoic acid, and salicylic acid, can be coupled with diazo compounds such as diazobenzene, and the product from alpha-naphthylamine can be diazotized and coupled with azo components. The products obtained from naphthalene, benzanilide, phenol, and benzyl chloride can be nitrated, and the product obtained from phenol gives a nitroso derivative when treated with nitrous acid. The Provisional Specification also mentions hydrazine as a suitable parent compound.