xanthate

thumb|150px|right|Sodium salt of ethyl xanthate ([[sodium ethylxanthate or sodium O-ethyl dithiocarbonate)]] thumb|150px|Structure of a xanthate ester thumb|Cellulose xanthate. A xanthate is a salt or ester of a xanthic acid. The formula of the salt of xanthic acid is (where R is organyl group and M is usually Na or K). Xanthate also refers to the anion . The formula of a xanthic acid is , such as ethyl xanthic acid, while the formula of a xanthate ester is , where R and R' are organyl groups. The salts of xanthates are sometimes called O-organyl dithioates. The esters of xanthic acid are sometimes called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek (xanthos) meaning 'yellowish' or '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 sulphide bearing ores. They are also versatile intermediates in organic synthesis.

==Formation and structure== Xanthate salts of alkali metals are produced by the treatment of an alcohol, alkali, and carbon disulfide. The process is called xanthation. In chemical terminology, the alkali reacts with the alcohol to produce an alkoxide, which is the nucleophile that adds to the electrophilic carbon atom in CS2. Often the alkoxide is generated in situ by treating the alcohol with sodium hydroxide or potassium hydroxide: ROH + CS2 + KOH → ROCS2K + H2O 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.