Thiodiglycol
From Wikipedia, the free encyclopedia
| Thiodiglycol | |
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| IUPAC name | 2-(2-Hydroxy-ethylsulfanyl)-ethanol |
| 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 |
| Identifiers | |
| CAS number | [111-48-8] |
| PubChem | |
| SMILES | OCCSCCO |
| Properties | |
| Molecular formula | C4H10O2S |
| Molar mass | 122.19 g/mol |
| Appearance | Clear to pale-yellow liquid |
| Melting point |
-16 °C, 257 K, 3 °F |
| Boiling point |
165 °C at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure |
| 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.
