Thiodiglycol

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The skeletal structure of thiodiglycol

A space-filling model of thiodiglycol

Thiodiglycol (bis(2-hydroxyethyl)sulfide) is a viscous, clear to pale-yellow liquid used as a solvent. Its chemical formula is C₄H₁₀O₂S, or HOCH₂CH₂SCH₂CH₂OH. Its melting point is -16 °C, its boiling point is 165 °C at 14 mm Hg (1.9 kPa) or decomposition at 282 °C at normal pressure. It is miscible with acetone, alcohols, and chloroform. It is soluble in benzene, ether, and tetrachloromethane. Its CAS number is [111-48-8] and its SMILES structure is OCCSCCO.

It is also known as 2,2'-thiodiethanol, β,β'-dihydroxydiethyl sulfide, β-thiodiglycol, thiodiethylene glycol, β-hydroxyethyl sulfide, 2-hydroxyethyl sulfide, bis(β-hydroxyethyl)sulfide, Glyecine A, Kromfax Solvent, Tedegyl.

Thiodiglycol is manufactured by reaction of 2-chloroethanol with sodium sulfide. It is structurally similar to diethylene glycol.

Thiodiglycol has both polar and nonpolar solvent properties. It is used as a solvent in dyeing textile. In chemical synthesis it is used as a building block for protection products, dispersants, fibers, plasticizers, rubber accelerators, pesticides, dyes, and various other organic chemicals. In manufacture of polymers, it is used as a chain transfer agent. It is an antioxidant. It is used as an additive to lubricants.

Thiodiglycol is used as a solvent for inks in ballpoint pens.

Thiodiglycol is a Chemical Weapons Convention schedule 2 chemical used in the production of sulfur-based blister agents, e.g. mustard gas.

Thiodiglycol is also a product of hydrolysis of mustard gas. It can be detected in the urine of casualties.