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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).
Density: 1.2659 g /cm 3 (15 °C) 1.0749 ... from benzoyl chloride. Dehydration to benzoic anhydride is induced with ... by the reaction of alcohols under acidic water ...
The usage of α-acyl sulfoxides and Lewis acids, such as TiCl 4 and SnCl 4, allow the reaction to proceed at lower temperatures (0 °C). [5] 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]
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It is also more expensive than thionyl chloride so it tends to be used on a smaller scale. This reaction involves conversion of N,N-dimethylformamide to the imidoyl chloride derivative (chloromethylene(dimethyl)ammonium ion (CH 3) 2 N + =CHCl), akin to the first stage in the Vilsmeier–Haack reaction. The imidoyl chloride is the active ...