Thiodiglycol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Thiodiglycol
Thiodiglycol-2D-skeletal.png
Thiodiglycol-3D-vdW.png
Names
IUPAC name
2-(2-Hydroxyethylsulfanyl)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
111-48-8 YesY
ChEBI CHEBI:75184 N
ChEMBL ChEMBL444480 YesY
ChemSpider 13881956 YesY
Jmol-3D images Image
PubChem 5447
UNII 9BW5T43J04 YesY
Properties
C4H10O2S
Molar mass 122.19 g/mol
Appearance Clear to pale-yellow liquid
Melting point −16 °C (3 °F; 257 K)
Boiling point 165 °C (329 °F; 438 K) at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Thiodiglycol, or bis(2-hydroxyethyl)sulfide (also known as 2,2-thiodiethanol or TDE), 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.

A relatively recent use (as of 2006) of thiodiglycol is as a mounting medium in microscopy. The ability to vary the refractive index of the medium by varying the concentration of TDE in an aqueous solution, plus its relative lack of toxicity makes it highly desirable for such use. The refractive index of the solution can be varied anywhere from near that of water (1.333) to that of glass (1.518).[1]

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.

References[edit]

  1. ^ Staudt T et al. (2006). "2,2′-Thiodiethanol: A new water soluble mounting medium for high resolution optical microscopy". Microscopy Research and Technique 70: 1–9. doi:10.1002/jemt.20396. 

External links[edit]