Di-tert-butyl peroxide → Phosphine oxide, diphenyl[3-(triethoxysilyl)propyl]-

HRID 1287964Notes

Reaction equation

HRID 1287964 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([Si:17]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[CH:15]=[CH2:16].C([O:31]OC(C)(C)C)(C)(C)C.P.C([SiH3])C=C>>[C:8]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:16][CH2:15][CH2:14][Si:17]([O:24][CH2:25][CH3:26])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23])=[O:31])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 8033Di-tert-butyl peroxide2×HCID 24404PhosphineHCID 70017Diphenylphosphine2×HCID 75692AllyltriethoxysilaneHCID 140349Silane, 2-propenyl-

Product 1

HCID 12058652Phosphine oxide, diphenyl[3-(triethoxysilyl)propyl]-Yield 216.6%

Procedure

To diphenylphosphine (18.0 g, 0.097 mol) heated to 140° C under a nitrogen atmosphere, a mixture of allyl triethoxysilane (19.8 g, 0.97 mol) and di-t-butyl peroxide (1.86 g) is added during 3/4 hour. Heating is continued for 1 hour after the addition is complete. Analysis of the liquid shows the presence of unreacted phosphine and allyl silane, so di-t-butyl peroxide (2.0 g) is added and heating continued 2 hours more. This analysis, addition, and heating is repeated once more, after which only a trace of diphenylphosphine is present. The liquid reaction mixture is distilled giving the product (11.2 g, 30 percent yield), b.p. 180- 184° C/0.7 mm, nD27 1.5340.

Workup

  1. additionis added during 3/4 hour
  2. temperatureHeating
  3. additionafter the addition
  4. additionis added
  5. temperatureheating
  6. waitcontinued 2 hours
  7. additionThis analysis, addition
  8. temperatureheating
  9. customThe liquid reaction mixture
  10. distillationis distilled

Sources & evidence

ORD record
ord-306191b9d355431cbda0c928b166c8b4
Source dataset
uspto-grants-1976_10
Patent number
US03987009

Reaction notes

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