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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.
Maleic anhydride is a classic substrate for Diels-Alder reactions. [7] It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride is converted to many pesticides and pharmaceuticals.
A typical representative organic reaction displaying this mechanism is the chlorination of alcohols with thionyl chloride, or the decomposition of alkyl chloroformates, the main feature is retention of stereochemical configuration. Some examples for this reaction were reported by Edward S. Lewis and Charles E. Boozer in 1952. [2]
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
Thionyl chloride can be used in place of acetic anhydride to trigger the elimination for forming the electrophilic intermediate and supplying chloride as the nucleophile to give an α-chloro-thioether: [6] Example of the Pummerer rearrangement using thionyl chloride. Other anhydrides and acyl halides can give similar products. Inorganic acids ...
The reaction proceeds with about 70% selectivity. About 10% of maleic anhydride is also produced: C 6 H 4 (CH 3) 2 + 7 + 1 / 2 O 2 → C 4 H 2 O 3 + 4 H 2 O + 4 CO 2. Phthalic anhydride and maleic anhydride are recovered by distillation by a series of switch condensers.
Density: 1.27 g/mL, liquid Melting point: 14.4 °C (57.9 °F; 287.5 K) ... Thionyl chloride and phosgene, the latter of which is also a choking agent, have also been ...
Dimethyl sulfite is prepared from a 1:2 ratio of thionyl chloride and methanol. [4] The reaction can be catalyzed by tertiary amine bases and likely proceeds via the chlorosulfinate (MeOS(O)Cl), [5] this intermediate will exist only fleetingly in the presence of methanol and as such its decomposition to methyl chloride and sulfur dioxide (via the slower SNi mechanism) is not observed to any ...
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