Triphenyl phosphite ozonide (TPPO) is a chemical compound with the formula PO
3(C
6H
5O)
3 that is used to generate
singlet oxygen
Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemical with the formula O=O (also written as or ), which is in a quantum state where all electrons are spin paired. It is kinetically unstable at ambie ...
.
When TPPO is mixed with
amines, the
ozonide breaks down into singlet oxygen and leaves behind
triphenyl phosphite
Triphenyl phosphite is the organophosphorus compound with the formula P(OC6H5)3. It is a colourless viscous liquid.
Preparation
Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a catalytic amount of base:
...
.
is the only known amine that can effectively cause the break down of TPPO while not quenching any of the produced oxygen.
Synthesis
Triphenyl phosphite ozonide is created by bubbling dry
ozone through
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
with triphenyl phosphite being added dropwise at -78 °C.
If triphenyl phosphite is added in excess in the synthesis, TPPO can be
reduced to triphenyl phosphite oxide, PO(C
6H
5O)
3, and oxygen gas.
References
Ozonides
Organophosphites
Phenol ethers
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