Thiodiglycol
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(2-hydroxyethyl) sulfide
bis(β-hydroxyethyl) sulfide
Glyecine A
Kromfax Solvent
Tedegyl
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.523
UNII
  • InChI=1S/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2 checkY
    Key: YODZTKMDCQEPHD-UHFFFAOYSA-N checkY
  • InChI=1/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2
    Key: YODZTKMDCQEPHD-UHFFFAOYAC
  • OCCSCCO
Properties
C4H10O2S
Molar mass 122.18 g·mol−1
Appearance colorless 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).
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Infobox references

Thiodiglycol, or bis(2-hydroxyethyl)sulfide (also known as 2,2-thiodiethanol or TDE), is the organosulfur compound with the formula S(CH2CH2OH)2. It is miscible with water and polar organic solvents. It is a colorless liquid. It is structurally similar to diethylene glycol.

Thiodiglycol is manufactured by reaction of 2-chloroethanol with sodium sulfide.[1]

Thiodiglycol is a polar protic solvent. 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 used 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).[2]

Thiodiglycol is a Chemical Weapons Convention schedule 2 chemical used in the production of sulfur-based mustard gases. Thiodiglycol is also a product of the hydrolysis of the "mustard gas" bis(2-chloroethyl)sulfide and can be detected in the urine of casualties.

References

  1. ↑ E. M. Faber and G. E. Miller (1932). "β-Thiodiglycol". Organic Syntheses. 12: 68. doi:10.15227/orgsyn.012.0068.
  2. ↑ 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. PMID 17131355. S2CID 13553493.
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