Acrylonitrile → Phosphinic acid, (2-cyanoethyl)methyl-, ethyl ester

HRID 1604074Notes

Reaction equation

HRID 1604074 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([O:7][P:8]([CH3:10])[OH:9])[CH3:6]>>[C:1]([CH2:2][CH2:3][P:8]([CH3:10])(=[O:9])[O:7][CH2:5][CH3:6])#[N:4]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 13145048O-ethyl-P-methyl-phosphonous acid

Product 1

HCID 10397098Phosphinic acid, (2-cyanoethyl)methyl-, ethyl esterYield 90.6%

Procedure

120 g (2.26 mol) of acrylonitrile are added dropwise over 12 hours at 160° C. to 324 g (3.0 mol) of methanephosphonous monoethylester with vigorous stirring and under an inert-gas atmosphere. The excess monoester is then distilled off at 0.4 mbar. The residue is distilled using a Vigreux column at 142-143° C. at 0.4 mbar, giving 330 g of ethyl 2-cyanoethylmethylphosphinate (refractive index nD22 : 1.4554). This corresponds to a yield of 90% of theory.

Workup

  1. distillationThe excess monoester is then distilled off at 0.4 mbar
  2. distillationThe residue is distilled
  3. customat 142-143° C.

Sources & evidence

ORD record
ord-77f4d1aed3464e558627823ce611c329
Source dataset
uspto-grants-1999_11
Patent number
US05990337

Reaction notes

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