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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.
The thionyl group is SO, a sulfur atom plus an oxygen atom. 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 oxychlorination, the combination of hydrogen chloride and oxygen serves as the equivalent of chlorine, as illustrated by this route to 1,2-dichloroethane: 4 HCl + 2 CH 2 =CH 2 + O 2 → 2 Cl−CH 2 −CH 2 −Cl + 2 H 2 O Structure of a bromonium ion. The addition of halogens to alkenes proceeds via intermediate halonium ions. In special ...
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]
The hydroxyl group on carboxylic acids may be replaced with a chlorine atom using thionyl chloride to give acyl chlorides. In nature, carboxylic acids are converted to thioesters. Thionyl chloride can be used to convert carboxylic acids to their corresponding acyl chlorides. First, carboxylic acid 1 attacks thionyl chloride, and chloride ion ...
Thionyl chloride [11] is a well-suited reagent as the by-products ... Carbon nucleophiles such as Grignard reagents, convert acyl chlorides to ketones, ...
NEWARK, Del, Nov. 01, 2024 (GLOBE NEWSWIRE) -- The thionyl chloride market is expected to reach a value of USD 518.7 million in 2024 and USD 829.9 million by 2034, registering a CAGR of 4.8% from 2024 to 2034.
Darzens halogenation is the chemical synthesis of alkyl halides from alcohols via the treatment upon reflux of a large excess of thionyl chloride or thionyl bromide (SOX 2) in the presence of a small amount of a nitrogen base, such as a tertiary amine or pyridine or its corresponding hydrochloride or hydrobromide salt.