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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.
Phosphorus trichloride is commonly used to convert primary and secondary alcohols to the corresponding chlorides. [14] As discussed above, the reaction of alcohols with phosphorus trichloride is sensitive to conditions. The mechanism for the ROH →RCl conversion involves the reaction of HCl with phosphite esters: P(OR) 3 + HCl ⇌ HP(OR) + 3 ...
The von Braun amide degradation is the chemical reaction of a monosubstituted amide with phosphorus pentachloride or thionyl chloride to give a nitrile and an organohalide. [1] It is named after Julius Jacob von Braun, who first reported the reaction. [2] [3] The von Braun amide degradation
Thionyl chloride [11] is a well-suited reagent as the by-products (HCl, SO 2) are gases and residual thionyl chloride can be easily removed as a result of its low boiling point (76 °C). Phosphorus chlorides
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]
Methylphosphonyl dichloride is produced by oxidation of methyldichlorophosphine, with sulfuryl chloride: [3] CH 3 PCl 2 + SO 2 Cl 2 → CH 3 P(O)Cl 2 + SOCl 2. It can also be produced from a range of methylphosphonates (e.g. dimethyl methylphosphonate) via chlorination with thionyl chloride. Various amines catalyse this process. [4]
Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula P O Cl 3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride . It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide . [ 4 ]
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid: [8] C 6 H 5 CCl 3 + H 2 O → C 6 H 5 COCl + 2 HCl C 6 H 5 CCl 3 + C 6 H 5 CO 2 H → 2 C 6 H 5 COCl + HCl. As with other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride or thionyl chloride.