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Thionyl Chloride

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thionyl chloride

[′thī·ən·əl ′klȯr‚īd]
(inorganic chemistry)
SOCl2 A toxic, yellowish to red liquid with a pungent aroma, soluble in benzene, decomposes in water and at 140°C; boils at 79°C; used as a chemical intermediate and catalyst. Also known as sulfur oxychloride; sulfurous oxychloride.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.
The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Thionyl Chloride

 

(SOCl2), a colorless liquid that fumes upon exposure to air. Thionyl chloride is prepared commercially by the direct reaction of S, O2 and Cl2 at 180°–200°C (using activated carbon as a catalyst) or by the action of excess SO2 on CCl 4in the presence of AlCl3 at 150°C and pressure of about 4 meganewtons per sq m, or 40 kilograms-force per sq cm. It is used for the preparation of sulfochlorinated polymer derivatives, and also as a chlorinating agent—for example, in the manufacture of dyes and pharmaceuticals.

Thionyl chloride is toxic; it irritates the mucous membranes, causing severe burns.

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.
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Then, 1.2 molar equivalence of thionyl chloride (0.406 mL, 0.662 g) was diluted with anhydrous DCM in a syringe (4 mL) and added dropwise by syringe to the solution.
Cinnamic acid dissolved in refluxing thionyl chloride with catalytic DMF was the preferred route for the synthesis of acyl chlorides destined for the synthesis of the ester, while the acyl chloride synthesized from cold oxalyl chloride in C[H.sub.2][Cl.sub.2] yielded much cleaner crude reaction mixtures and higher yields in the synthesis of the cinnamyl amide.
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