Ethanol → Ethyl diphenylphosphinite

HRID 500038Notes

Reaction equation

HRID 500038 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 diphenylphosphiniteYield 96.7%

Conditions

Temperature
80 °C

Procedure

The following starting materials were fed continuously at 80° C. into a reactor which was equipped with a three-stage inclined-blade stirrer and had been made inert with nitrogen: 1) mixture of 110.7 g of ethanol and 205.8 g of 1-methylimidazole and 2) chlorodiphenylphosphine (99.4% strength). Stream 1) was added at 330 ml/h and stream 2) was added at 380 ml/h. Both streams were introduced below the surface of the liquid. The reactor was equipped with an overflow from which reaction mixture could flow out continuously. The reactor volume up to the overflow was 710 ml. The reaction temperature was maintained at 80° C. To bring the system to equilibrium, the output obtained over the first 4 hours was discarded. The output was subsequently collected over a period of 1 hour and a mass balance was carried out. The output consisted of two liquid phases. Over a period of one hour, 497.2 g of upper phase and 280.8 g of lower phase were collected. The upper phase comprised 96.8% of EODPP. The upper phase was subsequently distilled under reduced pressure via a column filled with Raschig rings, giving 438.2 g of 99.74% strength EODPP. Together with the EODPP in the first fraction, the total yield was 96.7%.

Workup

  1. customThe following starting materials were fed continuously at 80° C. into a reactor
  2. customwhich was equipped with a three-stage inclined-blade stirrer
  3. additionStream 1) was added at 330 ml/h and stream 2)
  4. additionwas added at 380 ml/h
  5. additionBoth streams were introduced below the surface of the liquid
  6. customThe reactor was equipped with an overflow from which reaction mixture
  7. customthe output obtained over the first 4 hours
  8. customThe output was subsequently collected over a period of 1 hour
  9. custom497.2 g of upper phase and 280.8 g of lower phase were collected
  10. distillationThe upper phase was subsequently distilled under reduced pressure via a column
  11. additionfilled with Raschig rings
  12. customgiving 438.2 g of 99.74% strength EODPP

Sources & evidence

ORD record
ord-709d0caaf7e64e66a064ef34738196b8
Source dataset
uspto-grants-2010_08
Patent number
US07767852B2

Reaction notes

Loading…