Acrylonitrile → Ethyl(2-cyanoethyl)phosphinic acid

HRID 576008Notes

Reaction equation

HRID 576008 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-neck flask equipped with thermometer, reflux condenser, high-performance stirrer and dropping funnel. The reaction mixture is heated to 100° C. and 371 g (7 mol) of acrylonitrile and 500 g of a 5% sodium peroxodisulfate solution (1.5 mol % based on acrylonitrile) are added dropwise at atmospheric pressure. Then, the water is distilled off, and the residue is taken up in THF, extracted and filtered. The solvent of the filtrate is removed in vacuo to leave 732 g (83% of theory) of ethyl(2-cyanoethyl)phosphinic acid as oil.

Workup

  1. additioninitially charged to a 5 l five-neck flask
  2. customequipped with thermometer
  3. temperaturereflux condenser, high-performance stirrer
  4. distillationThen, the water is distilled off
  5. extractionextracted
  6. filtrationfiltered
  7. customThe solvent of the filtrate is removed in vacuo

Sources & evidence

ORD record
ord-8c087ff8509648dcae71cd92a1e1d70f
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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