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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.
In oxychlorination, hydrogen chloride instead of the more expensive chlorine is used for the same purpose: CH 2 =CH 2 + 2 HCl + 1 ⁄ 2 O 2 → ClCH 2 CH 2 Cl + H 2 O. Secondary and tertiary alcohols react with hydrogen chloride to give the corresponding chlorides. In the laboratory, the related reaction involving zinc chloride in concentrated ...
Aside from the widely used reactions described above, phosgene is also used to produce acyl chlorides from carboxylic acids: R−C(=O)−OH + COCl 2 → R−C(=O)−Cl + HCl + CO 2. For this application, thionyl chloride is commonly used instead of phosgene.
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 . In organic chemistry , the thionyl group is known as a sulfoxide group or sulfinyl group, and has the general structure RS(=O)R'.
All are easily hydrolyzed. Indeed, thionyl chloride can be used as a dehydration agent as the water molecules are converted into gaseous products, leaving behind the anhydrous solid chloride. [11] MgCl 2 ·6H 2 O + 6 SOCl 2 → MgCl 2 + 6 SO 2 + 12 HCl. Selenium and tellurium form similar compounds and also the oxo-bridged species F 5 AOAF 5 (A ...
The chlorination must be controlled as excess chlorine converts trichloromethanesulfenyl chloride into carbon tetrachloride. Steam distillation separates the trichloromethanesulfenyl chloride and hydrolyzes the disulfur dichloride. Reduction of trichloromethanesulfenyl chloride with, e.g., tin [2] or dihydroanthracene [3] produces thiophosgene:
Key applications of thionyl chloride also include the pharmaceutical, pesticide, dye, and organic synthesis industries, among others. Thionyl chloride's versatile nature allows it to serve as an acylation agent and a dehydrating agent in various chemical reactions, making it indispensable in the synthesis of specialty chemicals, dyes, and reagents.
A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. [4] It was released for medical use in September 1964. [5]