GB300503A - Manufacture of n-oxyethyl-derivatives of nucleal substitution products and homologues of 4-amino-1-oxybenzene - Google Patents

Abstract

300,503. I. G. Farbenindustrie Akt.- Ges. Nov. 12, 1927, [Convention date]. Oxyethylamino derivatives of 1-oxy-2-chlor-4- aminobenzene, 1-oxy-2-carboxy-4-aminobenzene and 1-oxy-3-methyl-4-aminobenzene.-A nuclear substitution product of 4-amino-1-oxybenzene is treated with glycolhalogenhydrin or with ethylene oxide at ordinary or raised temperature and pressure, and, if necessary, in the presence of an acid binding agent, a diluent, a solvent and/or a catalyst, in order to obtain the N-mono and dioxyethyl derivatives. The products are suitable as photographic developers. According to examples :-(1) 2-chlor-4-amino-1-oxybenzene is heated with ethylene chlorhydrin in the presence of water and calcium carbonate, sodium carbonate is added, the calcium carbonate filtered off, and the dioxyethylamino derivative extracted, after cooling, with ethylaoetate; (2) the mono oxyethylamino derivative is similarly obtained by using the requisite quantity of chlorhydrin, it is finally precipitated as sulphate by means of concentrated sulphuric acid from an alcoholic solution; (3) the dioxyethylamino derivative is obtained by passing ethylene oxide into a water suspension of the 2- chlor-4-amino-1-oxybenzene and evaporating in vacuo; (4) in order to obtain the corresponding mono oxyethylamino derivative, ethylene oxide is passed into a sulphuric acid suspension of the parent body until the dioxyethyl compound can be detected; the liquid is neutralized with sodium carbonate and extracted with ethylacetate; (5) 4- amino-1-oxybenzene-3-carboxylic acid is warmed with ethylenechlorhydrin, caustic soda is added, and the whole brought to the boil; after just acidifying and evaporating in vacuo, the dioxyethylamino derivative is extracted from the residue by means of hot alcohol; the same product is obtained by treating the parent body with ethylene oxide in the presence of sodium hydroxide and then proceeding in a similar manner; (6) the monooxyethylamino derivative of 4- amino-1-oxybenzene-2-carboxylic acid is obtained by heating the parent body with ethylenechlorhydrin in the presence of sodium carbonate and water; after neutralizing with acid, and evaporating in vacuo the product is extracted by means of alcohol the same compound is obtained by passing ethylene oxide into the sodium carbonate suspension of the parent body, until the dioxyethylamino derivative can be detected; (7) 4- amino-3-methyl-1-oxybenzene is treated with ethyleneoxide or ethylenechlorhydrin in order to give the dio-exyethylamino derivative ; (8) 4-amino- 3-methyl-1-oxybenzene is heated with ethylenechlorhydrin in the presence of calcium carbonate, sodium carbonate is added, the calcium carbonate filtered off, and the monooxyethylamino derivative extracted by means of ethylacetate from the filtrate; a solution of the product in alcohol is precipitated as oxalate by adding the calculated quantity of oxalic acid in alcohol. Specifications 280,873, 290,997; and 300,970, [Class 98 (ii), Photographic processes &c.], are referred to.