Thioxanthate

In chemistry, a thioxanthate is an organosulfur compound with the formula RSCS₂X. When X is an alkali metal, the thioxanthate is a salt. When X is a transition metal, the thioxanthate is a ligand, and when X is an organic group, the compounds are called thioxanthate esters. They are usually yellow colored compounds that often dissolve in organic solvents. They are used as precursors to some catalysts, froth flotation agents, and additives for lubricants.

Preparation and reactions

The alkali metal thioxanthates are produced by treating a thiol with a base in the presence of carbon disulfide, as illustrated by the preparation of sodium ethyl thioxanthate:.[1]

EtSH + NaOH + CS₂ → EtSCS⁻
₂Na⁺ + H₂O

Sodium ethyl thioxanthate is similar structurally to sodium ethyl xanthate.

Alkylation of such thioxanthate anions gives thioxanthate esters, as illustrated by the preparation of ethyl methyl thioxanthate:

EtSCS⁻
₂Na⁺ + MeI → EtSCS₂Me + NaI

Thioxanthate esters are also called esters of trithiocarbonate.

References

Haiduc, I. "1,1-Dithiolato Ligands" in Comprehensive Coordination Chemistry II Edited by McCleverty, J. A.; Meyer, T. J 2004, volume 1, pp. 349-376.

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[1] Haiduc, I. "1,1-Dithiolato Ligands" in Comprehensive Coordination Chemistry II Edited by McCleverty, J. A.; Meyer, T. J 2004, volume 1, pp. 349-376.