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Thionyl chloride is an inorganic compound with the chemical formula SOCl 2.It is a moderately volatile, colourless liquid with an unpleasant acrid odour.Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes (50,000 short tons) per year being produced during the early 1990s, [5] but is occasionally also used as a solvent.
Darzens halogenation is the chemical synthesis of alkyl halides from alcohols via the treatment upon reflux of a large excess of thionyl chloride or thionyl bromide (SOX 2) in the presence of a small amount of a nitrogen base, such as a tertiary amine or pyridine or its corresponding hydrochloride or hydrobromide salt.
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite, actually forming an intimate ion pair. The second step is the loss of a sulfur dioxide molecule and its replacement by the chloride, which was attached to the sulphite group.
In oxychlorination, the combination of hydrogen chloride and oxygen serves as the equivalent of chlorine, as illustrated by this route to 1,2-dichloroethane: 4 HCl + 2 CH 2 =CH 2 + O 2 → 2 Cl−CH 2 −CH 2 −Cl + 2 H 2 O Structure of a bromonium ion. The addition of halogens to alkenes proceeds via intermediate halonium ions. In special ...
The Beckmann rearrangement is often catalyzed by acid; however, other reagents have been known to promote the rearrangement. These include tosyl chloride, thionyl chloride, phosphorus pentachloride, phosphorus pentoxide, triethylamine, sodium hydroxide, trimethylsilyl iodide among others. [3]
Thionyl chloride is a crucial chemical intermediate in pharmaceutical synthesis, with the pharmaceutical industry's growth and demand for new drugs driving its consumption. The agricultural industry's need for pesticides and agrochemicals also fuels the demand for thionyl chloride, as it plays a significant role in producing these compounds.
It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. In 2013, about 75–80 % of global phosgene was consumed for isocyanates , 18% for polycarbonates and about 5% for other fine chemicals .
The thionyl group is SO, a sulfur atom plus an oxygen atom. It occurs in compounds such as thionyl fluoride , SOF 2 . Thionyl chloride , SOCl 2 , is a common reagent used in organic synthesis to convert carboxylic acids to acyl chlorides .