Diethyl dixanthogen disulfide

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Diethyl dixanthogen disulfide
Diethyldixanthogendisulfide.svg
Names
Preferred IUPAC name
O1,O3-Diethyl 2-(dithioperoxy)-1,3-dithiodicarbonic acid
Other names
Auligen, Antigal, Dixanthogen
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C6H10O2S4/c1-3-7-5(9)11-12-6(10)8-4-2/h3-4H2,1-2H3 Yes check.svgY
    Key: FVIGODVHAVLZOO-UHFFFAOYSA-N Yes check.svgY
  • S=C(SSC(=S)OCC)OCC
Properties
C6H10O2S4
Molar mass 242.38 g·mol−1
Appearanceyellow solid
Density 1.23 g/cm3 [1]
Melting point 30 °C (86 °F; 303 K)
Pharmacology
P03AA01 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diethyl dixanthogen disulfide (DEXD) is the organosulfur compound with the formula (C2H5OC(S)S)2. It is one of the most common dixanthogen disulfides, compounds of the type (ROC(S)S)2 (R = alkyl). A yellow solid, It is obtained by oxidation of sodium ethylxanthate or potassium ethylxanthate. [2] [3]

According to X-ray crystallography, the two C2H5OC(S)S) groups in solid diethyl dixanthogen disulfide are planar and are linked by a disulfide bond. The C-S-S-C dihedral angle is near 90°, as is common for acyclic disulfides. [1]

Occurrence and reactions

Diethylxanthogen reacts with aqueous base to regenerate the xanthate, at least partially. [4]

Diethylxanthogen arises by oxidation of xanthates during froth flotation. Diethylxanthogens are thought to participate in the flotation of certain sulfide minerals. [5]

References

  1. 1 2 Watanabe, Y. (1971). "The crystal structure of diethyldixanthogen". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27 (3): 644–649. doi:10.1107/S056774087100270X.
  2. ↑ Weber, Wolfgang G.; McLeary, James B.; Sanderson, Ron D. (2006). "Facile Preparation of Bis(thiocarbonyl)disulfides via Elimination". Tetrahedron Letters. 47 (27): 4771–4774. doi:10.1016/j.tetlet.2006.04.031.
  3. ↑ Schroll, Alayne L.; Barany, George (1986). "Novel Symmetrical and Mixed Carbamoyl and Aminopolysulfanes by Reactions of (Alkoxydichloromethyl)polysulfanyl Substrates with N-Methylaniline". The Journal of Organic Chemistry. 51 (10): 1866–1881. doi:10.1021/jo00360a039.
  4. ↑ Jones, M.H.; Woodcock, J.T. (1983). "Decomposition of Alkyl Dixanthogens in Aqueous Solutions". International Journal of Mineral Processing. 10: 1–24. doi:10.1016/0301-7516(83)90030-3.
  5. ↑ Leppinen, J.O. (1990). "FTIR and Flotation Investigation of the Adsorption of Ethyl Xanthate on Activated and Non-Activated Sulfide Minerals". International Journal of Mineral Processing. 30 (3–4): 245–263. doi:10.1016/0301-7516(90)90018-T.
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