Thiodiglycol
| Thiodiglycol
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| IUPAC name
| 2-(2-Hydroxy-ethylsulfanyl)-ethanol
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| Other names
| 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
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| Identifiers
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| CAS number
| [111-48-8]
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| PubChem
| 5447
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| SMILES
| OCCSCCO
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| Properties
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| Molecular formula
| C4H10O2S
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| Molar mass
| 122.19 g/mol
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| Appearance
| Clear to pale-yellow liquid
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| Melting point
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-16 °C, 257 K, 3 °F
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| Boiling point
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165 °C at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure
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Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
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Thiodiglycol, or bis(2-hydroxyethyl)sulfide, is a viscous, clear to pale-yellow liquid used as a solvent. Its chemical formula is C4H10O2S, or HOCH2CH2SCH2CH2OH. It is miscible with acetone, alcohols, and chloroform. It is soluble in benzene, ether, and tetrachloromethane.
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 a variety of applications ranging from dyeing textiles to inks in some ballpoint pens. 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 the manufacture of polymers, it is used as a chain transfer agent. As an antioxidant, it is used as an additive in lubricants.
Thiodiglycol is a Chemical Weapons Convention schedule 2 chemical used in the production of sulfur-based blister agents such as mustard gas. Thiodiglycol is also a product of the hydrolysis of mustard gas. It can be detected in the urine of casualties.
[edit] External links
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