Difference between revisions of "Thionyl chloride"
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[[Category:Schedule 3 chemicals]]
[[Category:Schedule 3 chemicals]]
Revision as of 00:00, 13 February 2019
| IUPAC name
| Other names
Sulfur monoxide dichloride
Sulfur oxide dichloride
|Molar mass||118.97 g/mol|
|Appearance|| Colorless fuming liquid (fresh)|
Yellowish fuming liquid (old)
|Odor||Suffocating, sulfur dioxide-like|
|Density||1.638 g/cm3 (at 20 °C)|
|Melting point||−104.5 °C (−156.1 °F; 168.7 K)|
|Boiling point||74.6 °C (166.3 °F; 347.8 K)|
|Solubility|| Reacts with alcohols, aldehydes, carboxylic acids, ketones, DMF, DMSO|
Miscible with benzene, carbon tetrachloride, chloroform, ethers, toluene
|Vapor pressure|| 15.7 kPa (25 °C)|
4.7 kPa (0 °C)
384 Pa (-40 °C)
|309.8 kJ/mol (gas)|
Std enthalpy of
|-245.6 kJ/mol (liquid)|
|Safety data sheet||ScinceLab|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is an extremely useful compound in chemistry, but it is extremely dangerous and toxic.
Thionyl chloride is sometimes confused with sulfuryl chloride, SO2Cl2, but the properties of these compounds differ significantly: Thionyl chloride is a source of chloride ions, while sulfuryl chloride is a source of chlorine.
- SOCl2 + H2O → 2 HCl + SO2
- SOCl2 + RCO2H → RC(O)Cl + SO2 + HCl
This reaction can be used to synthesize acetic anhydride.
Thionyl chloride is a colorless oily liquid that fumes in air. Old samples have a yellowish color, due to decomposition. Light accelerates its decomposition. Thionyl chloride reacts with water, carboxylic acids, alcohols and all protic solvents. It is however miscible and soluble in most aprotic solvents, such as benzene, carbon tetrachloride, chloroform, diethyl ether, toluene, xylene. Thionyl chloride melts at −104.5 °C and boils at 74.6 °C. It has a density of 1.638 g/cm3 at 20 °C.
Thionyl chloride is sold by various chemical suppliers, but due to its hazards it's not available to the amateur chemist. Its sale is regulated in many places.
Certain batteries contain small amounts of thionyl chloride, but it's impractical to extract it.
Thionyl chloride is listed on schedule 3 of the Chemical Weapons Convention and ordering large amounts may draw attention of the authorities.
Unlike its similar compound sulfuryl chloride, thionyl chloride is much more difficult to synthesize.
- SO3 + SCl2 → SOCl2 + SO2
Oleum can be used instead of sulfur trioxide, and this is usually preferred, as pure sulfur trioxide is a nightmare to produce, purify, store and use, while oleum is much easier to handle, even though it's not a pleasant experience either. The higher the sulfur trioxide concentration, the better the reaction yield is.
The resulting thionyl chloride is extracted via fractional distillation, best in low light conditions, under dry atmosphere.
SM user Magpie has made a small amount of thionyl chloride.
- SO2 + COCl2 → SOCl2 + CO2
However, due to phosgene's extreme toxicity, it's best to avoid this reaction all together.
- Make acyl chloride
- Make anhydrous metal chlorides
- Make anhydrous alcoholic solutions of HCl
Thionyl chloride is extremely toxic and should not be handled unless you're a professional. It reacts violently with water to give sulfur dioxide and hydrochloric acid, which are toxic and corrosive.
Thionyl chloride is best stored in sealed bottles, in a special cabinet, away from any light and moisture.
Thionyl chloride can be safely neutralized with an alkaline slurry or with dry calcium or sodium carbonate or bicarbonate.