Iodine → Triphenyl Phosphate

HRID 2417576Notes

Reaction equation

HRID 2417576 reaction equation
[P:1]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.II.[O:25]=O>[Fe](Cl)(Cl)Cl>[P:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:25]

Participants

5

Reactant 3

HCID 807IodineHCID 977OxygenHCID 7540Triphenyl phosphite

Product 1

HCID 8289Triphenyl Phosphate

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Procedure

To a one-liter, stainless steel Parr autoclave vessel equipped for agitation, heating/cooling, and gas pressurization were charged 710 grams (2.29 moles) of triphenyl phosphite, 1.78 grams (0.0070 mole; 0.31 mole %) of iodine, and 2.34 grams (0.0144 mole; 0.63 mole %) of anhydrous iron (III) chloride. The mixture was heated to 115°-120° C. with efficient agitation and pressurized with oxygen at 55 psig. These conditions were maintained by applying sufficient cooling to control the accompanying exotherm which subsided after about 2.5 hours. The oxygenation was continued until no oxygen pressure drop was observed when the reaction vessel was isolated from the outside pressure line. The total reaction time was 5 hours. When the reaction vessel was vented, there was obtained 747 grams of triphenyl phosphate, an amber liquid that solidified upon cooling to room temperature. Gas chromatography showed the absence of triphenyl phosphite, thus demonstrating that the conversion of the phosphite to the phosphate was quantitative.

Workup

  1. temperatureheating/cooling
  2. temperatureThe mixture was heated to 115°-120° C. with efficient agitation
  3. temperatureThese conditions were maintained
  4. temperatureby applying sufficient cooling
  5. customThe oxygenation
  6. customwas isolated from the outside pressure line
  7. waitThe total reaction time was 5 hours

Sources & evidence

ORD record
ord-aa787d67c679432794782f51fd152add
Source dataset
uspto-grants-1984_09
Patent number
US04469644

Reaction notes

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