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Concept
Phosphite ester
Summary
In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of an unobserved tautomer phosphorous acid, H3PO3, with the simplest example being trimethylphosphite, P(OCH3)3. Some phosphites can be considered esters of the dominant tautomer of phosphorous acid (HP(O)(OH)2). The simplest representative is dimethylphosphite with the formula HP(O)(OCH3)2. Both classes of phosphites are usually colorless liquids.
From PCl3
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. The overall reaction is as follows:
PCl3 + 3 C2H5OH → (C2H5O)2P(O)H + 2 HCl + C2H5Cl
Alternatively, when the alcoholysis is conducted in the presence of proton acceptors (typically an amine base), one obtains the C3-symmetric trialkyl derivatives:
PCl3 + 3 C2H5OH + 3 R3N → (C2H5O)3P + 3 R3NHCl
A base is not essential when using aromatic alcohols such as phenols, as they are not susceptible to attack by chloride, however it does catalyse the esterification reaction and is therefore often included.
By transesterification
Phosphite esters can also be prepared by transesterification, as they undergo alcohol exchange upon heating with other alcohols. This process is reversible and can be used to produce mixed alkyl phosphites. Alternatively, if the phosphite of a volatile alcohol is used, such as trimethyl phosphite, then the by product (methanol) can be removed by distillation, allowing the reaction to be driven to completion.
Phosphites are oxidized to phosphate esters:
P(OR)3 + [O] → OP(OR)3
This reaction underpins the commercial use of some phosphite esters as stabilizers in polymers.
Alkyl phosphite esters are used in the Perkow reaction for the formation of vinyl phosphonates, and in the Michaelis–Arbuzov reaction to form phosphonates.
Official source
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