GB710036A - The metal xanthates of the haloaryloxyalkanols - Google Patents

Abstract

The invention comprises metal xanthates of haloaryloxyalkanols, particularly those of formula: <FORM:0710036/IV (b)/1> wherein n represents 2 or 3, X represents a metal and R represents a haloaryl radical. Such compounds are prepared by reacting together a haloarylalkanol, a hydroxide of an alkali or alkaline-earth metal (including magnesium), e.g. sodium, calcium or potassium hydroxide, and carbon bisulphide. Products in which X represents sodium or potassium may be reacted with an aqueous solution of an alkaline earth metal salt or heavy metal salt, e.g. barium acetate, zinc chloride, copper sulphate or aluminium acetate, to produce the corresponding metal xanthate. Reaction temperatures of 20 DEG to 40 DEG C. are suitable. In examples (1) and (2) potassium 2-(2,4-dichlorophenoxy) ethyl xanthate is produced by adding potassium hydroxide to a solution of 2-(2,4-dichlorophenoxy) ethanol and carbon bisulphide in diethyl ether and normal pentane respectively, the reactants being in approximately equimolecular amounts. Similarly prepared are (3) potassium 1-(4-chlorophenoxy)-2 - propyl - xanthate; (4) potassium 1 - (4-chloro - 2 - methyl - phenoxy) - 2 - propyl xanthate; (5) potassium 1-(2,4,5-trichlorophenoxy)-2-propyl xanthate; (6) sodium 2-(2,4-dichlorophenoxy) ethyl xanthate; (7) sodium 2 - (2,4,5 - trichlorophenoxy) ethyl xanthate. There are also listed additional compounds of the above general formula, where R-O- represents a 4-choro-2-methylphenoxy-, 2,4-dibromophenoxy-, 2,4,5-trichlorophenoxy-, pentachlorophenoxy-, 2 - chlorophenoxy-, or 2 - bromo - 4 - chlorophenoxy radical, n is 2 or 3 and X is sodium, potassium or calcium. Zinc 1-(4-chlorophenoxy)-2-propyl xanthate is prepared by reacting potassium 1 - (4 - chlorophenoxy) - 2 - propyl xanthate with zinc chloride. The haloaryloxyalkanols used as starting materials may be prepared by reacting an alkali metal salt of the appropriate phenol with a monohaloaliphatic alcohol such as ethylene chlorhydrin, propylene chlorhydrin, 2 - chloro - 1 - propanol, 3 - bromo - 1 - propanol, 1 - chloro - 2 - propanol, 3 - chloro - 2 - butanol, and 3-chloro-2-pentanol. A list is given of ethanols and propanols substituted by the halophenoxy radicals specified above.