Triphenyl phosphite is the
organophosphorus compound with the
formula P(OC
6H
5)
3. It is a colourless viscous liquid.
Preparation
Triphenylphosphite is prepared from
phosphorus trichloride
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxi ...
and
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...
in the presence of a catalytic amount of base:
:PCl
3 + 3 HOC
6H
5 → P(OC
6H
5)
3 + 3 HCl
Reactions
Triphenylphosphite is a precursor to
trimethylphosphine
Trimethylphosphine is a neutral organophosphorus compound with the formula P(CH3)3, commonly abbreviated as PMe3. This colorless liquid has a strongly unpleasant odor, characteristic of alkylphosphines. The compound is a common ligand in coordin ...
, it serves as a source of P
3+ that is less electrophilic than phosphorus trichloride:
: (C
6H
5O)
3P + 3CH
3MgBr → P(CH
3)
3 + 3"MgBrOC
6H
5"
Triphenylphosphite is quaternized by
methyl iodide:
: (C
6H
5O)
3P + CH
3I →
H3(C6H5O)3Psup>+I
−
Coordination complexes
Triphenylphosphite is a common
ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
in
coordination chemistry. It forms zero-valent complexes of the type M
(OC6H5)3sub>4 (M = Ni, Pd, Pt). The nickel complex can be prepared by displacement of the diene from
bis(cyclooctadiene)nickel:
: Ni(COD)
2 + 4 P(OC
6H
5)
3 → Ni
(OC6H5)3sub>4 + 2 COD
Related complexes are
homogeneous catalyst
In chemistry, homogeneous catalysis is catalysis by a soluble catalyst in a solution. Homogeneous catalysis refers to reactions where the catalyst is in the same phase as the reactants, principally in solution. In contrast, heterogeneous catalysis ...
s for the
hydrocyanation
In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of ...
of
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s. It also forms a variety of Fe(0) and Fe(II) complexes such as the di
hydride
In chemistry, a hydride is formally the anion of hydrogen( H−). The term is applied loosely. At one extreme, all compounds containing covalently bound H atoms are called hydrides: water (H2O) is a hydride of oxygen, ammonia is a hydride ...
H
2Fe
(OC6H5)3sub>4.
Polyamorphism
Triphenylphosphite is a notable example of
polyamorphism
Polyamorphism is the ability of a substance to exist in several different amorphous modifications. It is analogous to the polymorphism of crystalline materials. Many amorphous substances can exist with different amorphous characteristics (e.g ...
in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K. One polymorphic modification of triphenyl phosphite was obtained by means of crystallization in
ionic liquid
An ionic liquid (IL) is a salt in the liquid state. In some contexts, the term has been restricted to salts whose melting point is below a specific temperature, such as . While ordinary liquids such as water and gasoline are predominantly made of ...
s.
[D.G. Golovanov, K.A. Lyssenko, M.Yu. Antipin, Ya.S. Vygodskii, E.I. Lozinskaya, A.S. Shaplov. ”Long-awaited polymorphic modification of triphenyl phosphite“, Cryst. Eng. Comm., 2005, v. 7, no. 77, P.465 – 468]
doi: 10.1039/b505052a
/ref>
References
{{reflist
Phenol ethers
Organophosphites