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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.
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 ...
Such species arise from the alcoholysis of phosphorus trichloride: PCl 3 + 3 ROH → P(OR) 3 + 3 HCl. The reaction is general, thus a vast number of such species are known. Phosphites are employed in the Perkow reaction and the Michaelis–Arbuzov reaction. They also serve as ligands in organometallic chemistry.
On an industrial scale, the acid is prepared by hydrolysis of phosphorus trichloride with water or steam: [5] PCl 3 + 3 H 2 O → HPO(OH) 2 + 3 HCl. HPO(OH) 2 could be produced by the hydrolysis of phosphorus trioxide: P 4 O 6 + 6 H 2 O → 4 HPO(OH) 2
Ph 3 PCl 2 can also be obtained by the reaction of iodobenzene dichloride (PhICl 2) and triphenylphosphine. [5] Alternatively, Ph 3 PCl 2 can be obtained by chlorination of triphenylphosphine oxide with, for example, phosphorus trichloride, as in Grignard's original 1931 synthesis. [1]
Tributylphosphine can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride although, as it is commercially available at reasonable prices, it is rare to have to perform the small-scale preparation. 3 CH 3 CH 2 CH 2 CH 2 MgCl + PCl 3 → P(CH 2 CH 2 CH 2 CH 3) 3 + 3 MgCl 2
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 ...