Ethanol → Ethyl diphenylphosphinite

HRID 500040Notes

Reaction equation

HRID 500040 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 156.7 g of 1-methylimidazole and 84.1 g of ethanol and 2) 370.0 g of chlorodiphenylphosphine (99.1% strength). Stream 1) was added at 167.5 g/h and stream 2) was added at 257.4 g/h. The volume of the mixing chamber was 3.3 ml. The top of the reaction mixing pump was thermostated to 80° C. The system was brought to equilibrium over a period of 60 minutes. The output was subsequently collected for 87 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. 370.0 g of chlorodiphenylphosphine were added. The output consisted of two liquid phases. During the 87 minutes, 389.3 g of upper phase and 219.2 g of lower phase were collected. The upper phase comprised 96.8% of EODPP, so that the yield determined by gas chromatography was 98.5%. The residence time of the reactants in the mixing chamber was 30 s.

Workup

  1. additionThe following feed streams were mixed continuously in a reaction
  2. additionmixing pump
  3. additionStream 1) was added at 167.5 g/h and stream 2)
  4. additionwas added at 257.4 g/h
  5. additionThe top of the reaction mixing pump
  6. customwas thermostated to 80° C
  7. customThe output was subsequently collected for 87 minutes in order
  8. addition370.0 g of chlorodiphenylphosphine were added
  9. customDuring the 87 minutes, 389.3 g of upper phase and 219.2 g of lower phase were collected
  10. waitThe residence time of the reactants in the mixing chamber was 30 s

Sources & evidence

ORD record
ord-b5955b81bf094b42abfcca51b2a76d23
Source dataset
uspto-grants-2010_08
Patent number
US07767852B2

Reaction notes

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