Xanthate

Xanthate usually refers to a salt with the formula ROCS−2M+ (R = alkyl; M+ = Na+, K+), thus O-esters of dithiocarbonate. The name xanthates is derived from Greek ξανθός xanthos, meaning “yellowish, golden”, and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and (in mining) for extraction of certain ores. They are also versatile intermediates in organic synthesis. Xanthates also refer to esters of xanthic acid. These esters have the structure ROC(=S)SR′. Xanthate usually refers to a salt with the formula ROCS−2M+ (R = alkyl; M+ = Na+, K+), thus O-esters of dithiocarbonate. The name xanthates is derived from Greek ξανθός xanthos, meaning “yellowish, golden”, and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and (in mining) for extraction of certain ores. They are also versatile intermediates in organic synthesis. Xanthates also refer to esters of xanthic acid. These esters have the structure ROC(=S)SR′. Xanthate salts are produced by the reaction of an alkoxide salt with carbon disulfide. The reaction involves the attack of the alkoxide nucleophile on the electrophile CS2. Often the alkoxide is generated in situ by treating the alcohol with sodium or potassium hydroxide: For example, sodium ethoxide gives sodium ethyl xanthate. Many alcohols can be used in this reaction. Technical grade xanthate salts are usually of 90–95% purity. Impurities include alkali-metal sulfides, sulfates, trithiocarbonates, thiosulfates, sulfites, or carbonates as well as residual raw material such as alcohol and alkali hydroxide. These salts are available commercially as powder, granules, flakes, sticks, and solutions are available.