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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 most common and practical synthesis, hence used in industrial manufacturing, is directly reacting phosphorus trichloride with excess sulfur at 180 °C. [6] PCl 3 + S → PSCl 3. Using this method, yields can be very high after purification by distillation. Catalysts facilitate the reaction at lower temperatures, but are not usually necessary.
Such species arise via alcoholysis reactions of the corresponding phosphonous and phosphinous chlorides ((PCl 2 R') and (PClR' 2) , respectively). The latter are produced by reaction of a phosphorus trichloride with a poor metal-alkyl complex, e.g. organomercury, organolead, or a mixed lithium-organoaluminum compound. [8]
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] It is mainly used to make ...
Phosphorus trichloride is a major industrial chemical and widely used starting material for phosphorus chemistry. Phosphorus tribromide is used in organic chemistry to convert alcohols to alkyl bromides and carboxylic acids to acyl bromides ( e.g. in the Hell-Volhard-Zelinsky reaction ).
This reaction is a variant of the Michael addition: CH 2 =CHCO 2 R + 3 H 3 PO 3 → (HO) 2 P(O)CH 2 CH 2 CO 2 R. In the Hirao coupling dialkyl phosphites (which can also be viewed as di-esters of phosphonic acid: (O=PH(OR) 2) undergo a palladium-catalyzed coupling reaction with an aryl halide to form a phosphonate.
Methyldichlorophosphine is produced by alkylation of phosphorus trichloride with methyl iodide followed by reduction of the resulting phosphonium salt with iron powder: [2] [3] CH 3 I + PCl 3 + AlCl 3 → [CH 3 PCl 3 ] + AlCl 3 I −
Phosphite esters are typically prepared by treating phosphorus trichloride with an alcohol. For alkyl alcohols the displaced chloride ion can attack the phosphite, causing dealkylation to give a dialkylphosphite and an organochlorine compound. [1] [2] The overall reaction is as follows: PCl 3 + 3 C 2 H 5 OH → (C 2 H 5 O) 2 P(O)H + 2 HCl + C 2 ...