Acrylonitrile → Ethyl(2-cyanoethyl)phosphinic acid

HRID 1028248Notes

Reaction equation

HRID 1028248 reaction equation
[CH2:1]([P:3]([OH:5])[OH:4])[CH3:2].[C:6](#[N:9])[CH:7]=[CH2:8].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>O>[CH2:1]([P:3]([CH2:8][CH2:7][C:6]#[N:9])(=[O:5])[OH:4])[CH3:2]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 62655Sodium PersulfateHCID 13411864Ethylphosphonous acid

Product 1

HCID 46929271Ethyl(2-cyanoethyl)phosphinic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

564 g (6 mol) of ethylphosphonous acid (produced as in Example 1) are dissolved in 860 g of water and initially charged to a 5 l five-necked flask equipped with thermometer, reflux condenser, high-performance stirrer and dropping funnel. After heating the reaction mixture to 100° C., 371 g (7 mol) of acrylonitrile and 500 g of a 5% strength sodium peroxodisulfate solution (1.5 mol % based on acrylonitrile) are added dropwise at atmospheric pressure over 1 h. The water is then distilled off in vacuo. The residue is taken up in tetrahydrofuran and extracted. The insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo and the residue is recrystallized from acetone to leave 732 g (83% of theory) of ethyl-(2-cyanoethyl)phosphinic acid as oil.

Workup

  1. additioninitially charged to a 5 l five-necked flask
  2. customequipped with thermometer
  3. temperaturereflux condenser, high-performance stirrer
  4. distillationThe water is then distilled off in vacuo
  5. extractionextracted
  6. filtrationThe insoluble salts are filtered off
  7. customThe solvent of the filtrate is removed in vacuo
  8. customthe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-684351a4d0654d07a5715e72baae0f41
Source dataset
uspto-grants-2014_05
Patent number
US08735477B2

Reaction notes

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