Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Thiodiglycol: Difference between pages

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| ImageFile = 2,2'-thiodiethanol 200.svg

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| OtherNames = 2,2'-Thiodiethanol<BR />β,β'-dihydroxydiethyl sulfide<BR />β-thiodiglycol<BR />thiodiethylene glycol<BR />β-hydroxyethyl sulfide<BR />2-hydroxyethyl sulfide<BR />bis(2-hydroxyethyl) sulfide<BR />bis(β-hydroxyethyl) sulfide<BR />Glyecine A<BR />Kromfax Solvent<BR />Tedegyl

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| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 75184

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| C = 4 | H = 10 | O = 2 | S = 1

| Appearance = colorless liquid

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| BoilingPtC = 165

| BoilingPt_notes = at 14 [[mmHg]] (1.9 [[kilopascal|kPa]]) or decomposition at 282 °C at normal pressure

|Section7={{Chembox Hazards

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'''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 solvent]]s. It is a colorless liquid. It is structurally similar to [[diethylene glycol]].

Thiodiglycol is manufactured by reaction of [[2-Chloroethanol|2-chloroethanol]] with [[sodium sulfide]].<ref>{{cite journal |doi=10.15227/orgsyn.012.0068|title=β-Thiodiglycol |journal=Organic Syntheses |year=1932 |volume=12 |page=68|author=E. M. Faber and G. E. Miller }}</ref>

Thiodiglycol is a polar protic solvent. It is used as a [[solvent]] in a variety of applications ranging from dyeing [[textile]]s to [[ink]]s in some [[ballpoint pen]]s. In chemical synthesis, it is used as a building block for protection products, dispersants, [[fiber]]s, [[plasticizer]]s, [[rubber accelerator]]s, [[pesticide]]s, [[dye]]s, and various other organic chemicals. In the manufacture of [[polymer]]s, it is used as a [[chain transfer agent]]. As an [[antioxidant]], it is used as an additive in [[lubricant]]s.

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).<ref>{{Cite journal| volume = 70| pages = 1–9| last = Staudt T| title = 2,2′-Thiodiethanol: A new water soluble mounting medium for high resolution optical microscopy| journal = Microscopy Research and Technique| year = 2006| issue = 1| doi = 10.1002/jemt.20396| pmid = 17131355| s2cid = 13553493|display-authors=etal| doi-access = free}}</ref>

Thiodiglycol is a [[Chemical Weapons Convention]] [[List of Schedule 2 substances (CWC)|schedule 2 chemical]] used in the production of sulfur-based [[mustard gas]]es. 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==

{{Reflist}}

==External links==

* [https://web.archive.org/web/20050418064653/http://www.cbwinfo.com/Chemical/Precursors/p1.html Blister agent degradation product/precursor: Thiodiglycol]

* [https://web.archive.org/web/20050723073434/http://www.cbwinfo.com/General/Proliferation/Thiodiglycol.html From textile sizing to poisoning: how thiodiglycol was made to lose its way]

[[Category:Solvents]]

[[Category:Thioethers]]

[[Category:Diols]]