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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Diethyl dixanthogen disulfide 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]

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Sodium ethyl xanthate (SEX) is an organosulfur compound with the chemical formula CH3CH2OCS2Na. It is a pale yellow powder, which is usually obtained as the dihydrate. Sodium ethyl xanthate is used in the mining industry as a flotation agent. A closely related potassium ethyl xanthate (KEX) is obtained as the anhydrous salt.

<span class="mw-page-title-main">Potassium ethyl xanthate</span> Chemical compound

Potassium ethyl xanthate (KEX) is an organosulfur compound with the chemical formula CH3CH2OCS2K. It is a pale yellow powder that is used in the mining industry for the separation of ores. It is a potassium salt of ethyl xanthic acid.

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.