Thionyl chloride



Thionyl chloride
Other names sulfurous oxychloride
sulfurous dichloride
sulfinyl chloride
sulfinyl dichloride
dichlorosulfoxide
Identifiers
CAS number 7719-09-7
Properties
Molecular formula SOCl2
Molar mass 118.97 g/mol
Appearance clear to yellow
odorous liquid
Density 1.638 g ml−1, liquid
Melting point

−104.5 °C

Boiling point

76 °C

Solubility in water Reactive
Viscosity 0.6 cP at ? °C
Structure
Molecular shape pyramidal
Dipole moment 1.4 D
Hazards
MSDS External MSDS
EU classification Corrosive (C)
NFPA 704
 
4
2
W
R-phrases R14, R20/22, R29, R35
S-phrases S45
Flash point non flammable
Related Compounds
Related compounds Sulfuryl chloride
Selenium oxydichloride
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Thionyl chloride (or thionyl dichloride) is an sulfuryl chloride, SO2Cl2, but the chemical properties of these S(IV) and S(VI) compounds differ significantly.

Properties and structure

The molecule SOCl2 is pyramidal, indicating the presence of a lone pair of electrons on the S(IV) center. In contrast, COCl2 is planar.

SOCl2 reacts with water to release hydrogen chloride and sulfur dioxide.

HCl

Because of its high reactivity toward water, SOCl2 would not be expected to occur in nature.

Production

The major industrial synthesis involves the reaction of sulfur dichloride:[1]

SCl2 → SOCl2 + SO2.

Other methods include

SO2 + PCl5 → SOCl2 + POCl3;
SO2 + Cl2 + SCl2 → 2 SOCl2;
SO3 + Cl2 + 2 SCl2 → 3 SOCl2.

The first of the above three reactions also affords phosphorus oxychloride (or phosphoryl chloride), which resembles thionyl chloride in many of its reactions.

Applications

Thionyl chloride is used inside lithium-thionyl chloride chemical compounds or materials.

In military usage, thionyl chloride is used in the "di-di" method of producing G-series nerve agents.

Organic chemistry

Thionyl chloride is widely used to convert distillation.

RC(O)Cl + SO2 + HCl
R-OH + O=SCl2 → R-Cl + SO2 + HCl

phosphoryl chlorides.

Thionyl chloride will react with primary isocyanides.[10]

nitriles.[11]

Inorganic chemistry

Anhydrous metal chlorides may be obtained from hydrated metal chlorides by refluxing in freshly distilled thionyl chloride:[12]

MCln·xH2O + x SOCl2 → MCln + x SO2 + 2x HCl

Safety

SOCl2 is toxic, corrosive, and phosphites.

Industrial production of thionyl chloride is controlled under the schedule 3.

References

  1. ^ N. N. Greenwood, A. Earnshaw, Chemistry of the Elements, Pergamon Press, 1984.
  2. ^ Allen, C. F. H.; Byers, Jr., J. R.; Humphlett, W. J. (1963). "Oleoyl chloride". Org. Synth.; Coll. Vol. 4: 739. 
  3. ^ Rutenberg, M. W.; Horning, E. C. (1963). "1-Methyl-3-ethyloxindole". Org. Synth.; Coll. Vol. 4: 620. 
  4. ^ Mondanaro, K. R.; Dailey, W. P. (2004). "3-Chloro-2-(chloromethyl)-1-propene". Org. Synth.; Coll. Vol. 10: 212. 
  5. ^ Krakowiak, K. E.; Bradshaw, J. S. (1998). "4-Benzyl-10,19-diethyl-4,10,19-triaza-1,7,13,16-tetraoxacycloheneicosane". Org. Synth.; Coll. Vol. 9: 34. 
  6. ^ Weinreb, S. M.; Chase, C. E.; Wipf, P.; Venkatraman, S. (2004). "2-Trimethylsilylethanesulfonyl chloride (SES-Cl)". Org. Synth.; Coll. Vol. 10: 707. 
  7. ^ Hazen, G. G.; Bollinger, F. W.; Roberts, F. E.; Russ, W. K.; Seman, J. J.; Staskiewicz, S. (1998). "4-Dodecylbenzenesulfonyl azides". Org. Synth.; Coll. Vol. 9: 400. 
  8. ^ Hulce, M.; Mallomo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. H. (1990). "(S)-( + )-2-(p-toluenesulfinyl)-2-cyclopentenone: Precursor for enantioselective synthesis of 3-substituted cyclopentanones". Org. Synth.; Coll. Vol. 7: 495. 
  9. ^ Kurzer, F. (1963). "p-Toluenesulfinyl chloride". Org. Synth.; Coll. Vol. 4: 937. 
  10. ^ Niznik, G. E.; Morrison, III, W. H.; Walborsky, H. M. (1988). "1-d-Aldehydes from organometallic reagents: 2-methylbutanal-1-d". Org. Synth.; Coll. Vol. 6: 751. 
  11. ^ Krynitsky, J. A.; Carhart, H. W. (1963). "2-Ethylhexanonitrile". Org. Synth.; Coll. Vol. 4: 436. 
  12. ^ Alfred R. Pray, Richard F. Heitmiller, Stanley Strycker. "Anhydrous Metal Chlorides". Inorganic Syntheses 28: 321 - 323. doi:10.1002/9780470132593.ch80.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thionyl_chloride". A list of authors is available in Wikipedia.