Ethanol → Ethyl diphenylphosphinite

HRID 500039Notes

Reaction equation

HRID 500039 reaction equation
CN1C=CN=C1.Cl[P:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][P:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 13901-MethylimidazoleHCID 66180Chlorodiphenylphosphine

Product 1

HCID 69754Ethyl diphenylphosphinite

Procedure

The following feed streams were mixed continuously in a reaction mixing pump: 1) mixture of 159.2 g of 1-methylimidazole and 85.4 g of ethanol and 2) 372.8 g of chlorodiphenylphosphine (99.1% strength). Stream 1) was added at 1257 g/h and stream 2) was added at 1928 g/h. The volume of the mixing chamber was 3.3 ml. The top of the reaction mixing pump was thermostated to 120° C. The system was brought to equilibrium over a period of 5 minutes. The output was subsequently collected for 11 minutes in order to carry out a mass balance. During the mass balance run, the amount of starting materials was determined by weighing the reservoirs. 372.8 g of chlorodiphenylphosphine were added. The output consisted of two liquid phases. During the 11 minutes, 392.2 g of upper phase and 218.3 g of lower phase were collected. The upper phase comprised 96.5% of EODPP, so that the yield determined by gas chromatography was 98.2%. The residence time of the reactants in the mixing chamber was 4 s, so that the space-time yield was 0.69×106 kgm−3h−1.

Workup

  1. additionThe following feed streams were mixed continuously in a reaction
  2. additionmixing pump
  3. additionStream 1) was added at 1257 g/h and stream 2)
  4. additionwas added at 1928 g/h
  5. additionThe top of the reaction mixing pump
  6. customwas thermostated to 120° C
  7. customThe output was subsequently collected for 11 minutes in order
  8. addition372.8 g of chlorodiphenylphosphine were added
  9. customDuring the 11 minutes, 392.2 g of upper phase and 218.3 g of lower phase were collected
  10. waitThe residence time of the reactants in the mixing chamber was 4 s, so that the space-time yield was 0.69×106 kgm−3h−1

Sources & evidence

ORD record
ord-c6b8b44f7dae43a39b54c99b317fbfc2
Source dataset
uspto-grants-2010_08
Patent number
US07767852B2

Reaction notes

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