Sulfur dichloride

From WikiChem
Jump to: navigation, search
Sulfur dichloride
IUPAC name sulfur dichloride
Other names dichlorosulfane
Identifiers
InChI InChI=1/Cl2S/c1-3-2
InChIKey FWMUJAIKEJWSSY-UHFFFAOYAS
Standard InChI InChI=1S/Cl2S/c1-3-2
Standard InChIKey FWMUJAIKEJWSSY-UHFFFAOYSA-N
CAS number [10545-99-0]
EC number 234-129-0
ChemSpider 23682
Properties[1]
Chemical formula SCl2
Molar mass 102.97 g mol−1
Appearance red liquid
Density 1.621 g cm−3
Melting point

−122 °C

Boiling point

59 °C decomp.

Solubility in water reacts violently
Structure[1]
Molecular geometry bent; S–Cl = 201 pm, Cl–S–Cl = 103°
Thermochemistry[2]
Std enthalpy of formation ΔfHo298 −49.79 kJ mol−1
Standard molar entropy So298 183.68 J K−1 mol−1
Hazards[3]
Material safety data sheet (MSDS) ICSC 1661
EU index number 016-013-00-X
GHS pictograms Skin Corr. 1BSTOT SE 3Aquatic Acute 1
GHS signal word DANGER
GHS hazard statements H314, H335, H400
Related compounds
Other anions Sulfur difluoride
Sulfur dibromide
Sulfur diiodide
Other cations Tellurium dichloride
Polonium dichloride
Other chlorides of sulfur Disulfur dichloride
Sulfur tetrachloride
Thionyl chloride
Sulfuryl chloride
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Sulfur dichloride, SCl2, is the highest thermally stable chloride of sulfur. It is also the first in a homologous series of dichlorosulfanes, SnCl2.

Preparation and purification

Sulfur dichloride is prepared by the chlorination of elemental sulfur, with disulfur dichloride as an intermediate.

S8 + 4 Cl2 → 4 S2Cl2
S2Cl2 + Cl2 → 2 SCl2

Sulfur dichloride is often contaminated with S2Cl2, but can be stabilized with a small amount of phosphorus pentachloride.[1] It is purified by distillation, often as an azeotrope with phosphorus trichloride (99% SCl2).[4]

Reactions

Sulfur dichloride is used as a precursor to organosulfur compounds, as it adds easily to C=C double bonds:[4] a well-known example is in the manufacture of mustard gas from SCl2 and ethylene.[1]

SCl2 + 2 H2C=CH2 → ClCH2CH2SCH2CH2Cl

It is also used in the industrial preparation of thionyl chloride.[1]

SCl2 + SO3 → SOCl2 + SO2

Fluorination of SCl2 with sodium fluoride leads to disproportionation, and provides a convenient synthesis of sulfur tetrafluoride, a versatile fluorinating agent.[5][6][7]

3 SCl2 + 4 NaF → SF4 + S2Cl2 + 4 NaCl

The reaction of sulfur dichloride with water is vigorous, and leads to extensive disproportionation and a variety of products.[1]

Notes and references

Notes

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 Greenwood, Norman N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, 1984; pp 815–16, 820. ISBN 0-08-022057-6.
  2. Sulfur dichloride. In NIST Chemistry WebBook; National Institute for Standards and Technology, <http://webbook.nist.gov/cgi/inchi/InChI%3DInChI=1S/Cl2S/c1-3-2>. (accessed 17 September 2010).
  3. Index no. 016-013-00-X of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 399.
  4. 4.0 4.1 Bishop, Roger 9-Thiabicyclo[3.3.1]nonane-2,6-dione. Org. Synth. 1992, 70, 120, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0692>; Coll. Vol., 9, 692.
  5. Tullock, C. W.; Fawcett, F. S.; Smith, W. C.; Coffman, D. D. The Chemistry of Sulfur Tetrafluoride. I. The Synthesis of Sulfur Tetrafluoride. J. Am. Chem. Soc. 1960, 82 (3), 539–42. DOI: 10.1021/ja01488a011.
  6. Tullock, Charles W. (Du Pont) Synthesis of sulfur tetrafluoride. US Patent 2992073, issued 11 July 1961.
  7. Fawcett, F. S.; Tullock, C. W. Inorg. Synth. 1963, 7, 119.

External links

Error creating thumbnail: Unable to save thumbnail to destination
This page is currently licensed under the Creative Commons Attribution 3.0 Unported license and any later versions of that license.