Thionyl chloride
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| Thionyl chloride | ||||
|---|---|---|---|---|
 
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| General | ||||
| Systematic name | Thionyl dichloride | |||
| Other names | Sulfurous oxychloride Sulfurous dichloride Sulfinyl chloride Sulfinyl dichloride Dichlorosulfoxide | |||
| Molecular formula | SOCl2 | |||
| Molar mass | 118.97 g/mol | |||
| Appearance | clear to yellow odorous liquid | |||
| CAS number | 7719-09-7 | |||
| Properties | ||||
| Density | 1.638 g/ml, liquid | |||
| Solubility in water | Reactive | |||
| Melting point | −104.5 °C | |||
| Boiling point | 76 °C | |||
| Viscosity | ? cP at ? °C | |||
| Structure | ||||
| Molecular shape | pyramidal | |||
| Dipole moment | ? D | |||
| Hazards | ||||
| MSDS | External MSDS | |||
| EU classification | Corrosive (C) | |||
| NFPA 704 |
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| R-phrases | R14, R20/22, R29, R35 | |||
| S-phrases | S1/2, S26, S36/37/39, S45 | |||
| Flash point | non flammable | |||
| Supplementary data page | ||||
| Structure and properties | n, εr, etc. | |||
| Thermodynamic data | Phase behaviour Solid, liquid, gas | |||
| Spectral data | UV, IR, NMR, MS | |||
| Related compounds | ||||
| Other anions | Thionyl bromide Thionyl iodide | |||
| Related compounds | Sulfuryl chloride Selenium oxydichloride | |||
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | ||||
Thionyl chloride (or thionyl dichloride) is an inorganic compound with the formula SOCl2. SOCl2 is a reactive chemical reagent used in chlorination reactions. It is a colorless, distillable liquid at room temperature and pressure that decomposes above 140 °C. SOCl2 is sometimes confused with 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 (HCl) and sulfur dioxide (SO2).
Because of its high reactivity toward water, SOCl2 would not be expected to occur in nature.
Industrial usage
Thionyl chloride is used inside lithium-thionyl chloride batteries as the positive active material with lithium as the negative active material. It is also used as a reagent for the production of other chemical compounds or materials.In military usage, thionyl chloride is used in the "di-di" method of producing G-series nerve agents.
Organic chemistry usage
Preparation of acid chlorides
Thionyl chloride is widely used both in the laboratory and on an industrial scale. It reacts with carboxylic acids to produce acyl chlorides.[#endnote_Allen1957][#endnote_Rutenberg1950]Sulfonic acids react with thionyl chloride to produce sulfonyl chlorides.[#endnote_Weinreb1998][#endnote_Hazen1996] Likewise, thionyl chloride will transform sulfinic acids into sulfinyl chlorides[#endnote_Hulce1986][#endnote_Kurzer1954] and phosphonic acids into phosphoryl chlorides.
Chlorination of alcohols
Thionyl chloride also reacts with alcohols to produce alkyl chlorides.[#endnote_Mondanaro1998][#endnote_Krakowiak1992]A milder alternative is the Appel reaction.
Miscellanous reactions
Thionyl chloride will react with primary formamides to form isocyanides.[#endnote_Niznik1971]Amides will react with thionyl chloride to form imidoyl chlorides. However, primary amides under heating with thionyl chloride will continue on to form nitriles.[#endnote_Krynitsky1952]
Synthesis of thionyl chloride
The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride:[#endnote_Greenwood1984]Other methods include:
The first of the above three reactions also makes phosphorus oxychloride (or phosphoryl chloride), which resembles thionyl chloride in many of its reactions.
Safety and toxity considerations
SOCl2 is toxic, corrosive, and lachrymatory. It is a skin and inhalation hazard, as well as being odorous,Industrial production of thionyl chloride is controlled under the Chemical Weapons Convention, where it is listed in schedule 3.
References
- ↑ Allen, C. F. H.; Byers, Jr., J. R.; Humphlett, W. J. Org. Syn., Coll. Vol. 4, p.739 (1963); Vol. 37, p.66 (1957). ([Article])
- ↑ Rutenberg, M. W.; Horning, E. C. Org. Syn., Coll. Vol. 4, p.620 (1963); Vol. 30, p.62 (1950). ([Article])
- ↑ Weinreb, S. M.; Chase, C. E.; Wipf, P.; Venkatraman, S. Org. Syn., Coll. Vol. 10, p.707 (2004); Vol. 75, p.161 (1998). ([Article])
- ↑ Hazen, G. G.; Bollinger, F. W.; Roberts, F. E.; Russ, W. K.; Seman, J. J.; Staskiewicz, S. Org. Syn., Coll. Vol. 9, p.400 (1998); Vol. 73, p.144 (1996). ([Article])
- ↑ Hulce, M.; Mallomo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. H. Org. Syn., Coll. Vol. 7, p.495 (1990); Vol. 64, p.196 (1986). ([Article])
- ↑ Kurzer, F. Org. Syn., Coll. Vol. 4, p.937 (1963); Vol. 34, p.93 (1954). ([Article])
- ↑ Mondanaro, K. R.; Dailey, W. P. Org. Syn., Coll. Vol. 10, p.212 (2004); Vol. 75, p.89 (1998). ([Article])
- ↑ Krakowiak, K. E.; Bradshaw, J. S. Org. Syn., Coll. Vol. 9, p.34 (1998); Vol. 70, p.129 (1992). ([Article])
- ↑ Niznik, G. E.; Morrison, III, W. H.; Walborsky, H. M. Org. Syn., Coll. Vol. 6, p.751 (1988); Vol. 51, p.31 (1971). ([Article])
- ↑ Krynitsky, J. A.; Carhart, H. W. Org. Syn., Coll. Vol. 4, p.436 (1963); Vol. 32, p.65 (1952). ([Article])
- ↑ N. N. Greenwood, A. Earnshaw, Chemistry of the Elements, Pergamon Press, 1984.
External links
- Usage of [thionyl chloride] in Organic Syntheses
- [International Chemical Safety Card 1409] -->
- [NIOSH Pocket Guide to Chemical Hazards]
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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