General Description
Clear, pale yellow liquid with a clean, pleasant odor.
Reactivity Profile
Organophosphates, such as TRIPHENYL PHOSPHITE(101-02-0), are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Air & Water Reactions
Insoluble in water.
Fire Hazard
This chemical is combustible.
Health Hazard
Triphenyl phosphite (TPP) is a
skin irritant and sensitizer in humans and is
neurotoxic in laboratory animals.Systemic effects have not been reported in
humans.
reaction suitability
Buchwald-Hartwig Cross-Coupling Reaction; Heck Reaction; Hiyama Coupling; Negishi Couplingp; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling.
Synthesis
1120.5 g (11.90 mol) of phenol (3.3 eq.) are placed in a 3-necked, 3-liter flask filled with nitrogen. 494.0 g (3.60 mol) of phosphorus trichloride is charged into a dropping funnel, and 864.5 g of distilled water is poured into an absorption flask for trapping hydrogen chloride. The reaction mixture is heated in an oil bath to a temperature of 45 ° C with stirring, and phosphorus trichloride is added dropwise over 240 minutes. Next, the reaction mixture is stirred for 20 minutes, heated to a temperature of 70 ° C for 10 minutes, kept at this temperature for 10 minutes, heated to a temperature of 160 ° C for 30 minutes and kept for 1.5 hours. Disconnect and weigh the absorption flask with an aqueous solution of hydrogen chloride and get 1242.0 g of hydrochloric acid (30.4 wt%). Replace the reflux condenser with a distillation nozzle with a once-through cooler and a receiving flask. The reaction flask is heated to a temperature of 170 ° C and maintained for 60 minutes under vacuum at a residual pressure of 300-350 mm RT. Art. Gradually reduce the vacuum to a residual pressure of 10 mm RT. Art. and phenol distillate 149.3 g is collected. After phenol is distilled off, triphenyl phosphite weighing 1091.3 g is obtained.
Purification Methods
Its ethereal solution is washed succesively with aqueous 5% NaOH, distilled water and saturated aqueous NaCl, then dried with Na2SO4 and distilled under vacuum after evaporating the diethyl ether. [Walsh J Am Chem Soc 81 3023 1959, Verkade & Coskren in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973, Beilstein 6 IV 695.]
