Acrylonitrile → Butyl ethyl(2-cyanoethyl)phosphinate

HRID 576010Notes

Reaction equation

HRID 576010 reaction equation
[CH2:1]([P:3]([O-:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].[C:10](#[N:13])[CH:11]=[CH2:12]>C1(C)C=CC=CC=1>[CH2:1]([P:3]([CH2:12][CH2:11][C:10]#[N:13])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 19606949Butyl ethyl(2-cyanoethyl)phosphinateYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

150 g (1 mol) of butyl ethylphosphonite (produced as in Example 2) and 64 g (1.2 mol) of acrylonitrile in 217 g of toluene are heated to about 100° C. While stirring, 124 g of a 10% solution of Wako V65 in toluene are added by metered addition. The solvent is distilled off in vacuo to leave 171 g (84% of theory) of butyl ethyl(2-cyanoethyl)phosphinate.

Workup

  1. distillationThe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-d356d4fff6c448fd997496b302ae4cc0
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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