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Disulfur dichloride

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Disulfur dichloride
Wireframe model of disulfur dichloride
Ball and stick model of disulfur dichloride
Ball and stick model of disulfur dichloride
Spacefill model of disulfur dichloride
Spacefill model of disulfur dichloride
Names
IUPAC name Disulfur dichloride
Systematic IUPAC name Dichlorodisulfane
Other names Bis(S–S)

Dimeric sulfenic chloride

Sulfur monochloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.030.021 Edit this at Wikidata
EC Number
  • 233-036-2
MeSH Sulfur+monochloride
PubChem CID
RTECS number
  • WS4300000
UN number 3390
CompTox Dashboard (EPA)
InChI
  • InChI=1S/Cl2S2/c1-3-4-2Key: PXJJSXABGXMUSU-UHFFFAOYSA-N
  • InChI=1/Cl2S2/c1-3-4-2Key: PXJJSXABGXMUSU-UHFFFAOYAK
SMILES
  • ClSSCl
Properties
Chemical formula S2Cl2
Molar mass 135.04 g/mol
Appearance yellow liquid
Density 1.688 g/cm
Melting point −80 °C (−112 °F; 193 K)
Boiling point 137.1 °C (278.8 °F; 410.2 K)
Solubility in water decomp with loss of HCl
Solubility soluble in ethanol, benzene, ether, chloroform, CCl4
Refractive index (nD) 1.658
Structure
Coordination geometry gauche
Dipole moment 1.60 D
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2 1 1
Flash point 118.5 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Disulfur dichloride is the chemical compound with the formula S2Cl2 . Some alternative names for this compound are sulfur monochloride (the name implied by its empirical formula, SCl), disulphur dichloride (British English Spelling) and sulphur monochloride (British English Spelling). S2Cl2 has the structure implied by the formula Cl-S-S-Cl, wherein the angle between the Cl-S-S and S-S-Cl planes is 90°. This structure is referred to as gauche, and is akin to that for H2O2. A different isomer of S2Cl2 is S=SCl2; this isomer forms transiently when S2Cl2 is exposed to UV-radiation (see thiosulfoxides).

Synthesis and basic properties

Pure disulfur dichloride is a yellow liquid that smokes in air due to reaction with water:

2 S2Cl2 + 2 H2O → SO2 + 4 HCl + 3/8 S8

It is synthesized by partial chlorination of elemental sulfur. The reaction takes place at usable rates at room temperature. In the laboratory, chlorine gas is led into a flask containing elemental sulfur. As disulfur dichloride is formed, the contents become a golden yellow liquid:

S8 + 4 Cl2 → 4 S2Cl2 ΔH = −58.2 kJ/mol

Excess chlorine gives sulfur dichloride which causes the liquid to become less yellow and more orange-red:

S2Cl2 + Cl2 ↔ 2 SCl2 ΔH = −40.6 kJ/mol

The reaction is reversible, and upon standing, SCl2 releases chlorine to revert to the disulfur dichloride. Disulfur dichloride has the ability to dissolve large quantities of sulfur, which reflects in part the formation of polysulfanes:

S2Cl2 + n S → S2+nCl2

Pure disulfur dichloride is obtained by distilling the yellow-orange liquid over excess elemental sulfur.

S2Cl2 also arises from the chlorination of CS2 as in the synthesis of thiophosgene.

Applications

S2Cl2 has been used to introduce C-S bonds. In the presence of AlCl3, S2Cl2 reacts with benzene to give diphenyl sulfide:

S2Cl2 + 2 C6H6 → (C6H5)2S + 2 HCl + 1/8 S8

Anilines react with S2Cl2 in the presence of NaOH via the so-called Herz reaction to give ortho-aminothiophenolates. These species are precursors to thioindigo dyes. It is also used to prepare the sulfur mustard "gas" by reaction with ethylene at 60°C (the Levinstein process):

S2Cl2 + 2 C2H4 → (ClC2H4)2S + 1/8 S8

Other uses include manufacturing sulfur dyes, insecticides, synthetic rubbers. Also used in cold vulcanization of rubbers, as polymerization catalyst for vegetable oils and for hardening soft woods.

References

  1. ^ Pradyot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0070494398
  2. Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
  3. Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934). "Diphenylsulfide". Organic Syntheses. 14: 36; Collected Volumes, vol. 2, p. 242.
  4. R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4
  5. Garcia-Valverde M., Torroba T. (2006). "Heterocyclic chemistry of sulfur chlorides - Fast ways to complex heterocycles". European Journal of Organic Chemistry. 4 (4): 849–861. doi:10.1002/ejoc.200500786.
  6. F. Fehér "Dichlorodisulfane" in Handbook of Preparative Inorganic Chemistry, 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. 371.
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