Acrylonitrile → Butyl ethyl(2-cyanoethyl)phosphinate

HRID 576011Notes

Reaction equation

HRID 576011 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].[O-]CCCC.[Na+]>>[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 3

HCID 7855AcrylonitrileHCID 23669364Sodium n-butylateHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 19606949Butyl ethyl(2-cyanoethyl)phosphinateYield 90%

Procedure

A 1 l five-neck flask equipped with thermometer, reflux condenser, high-performance stirrer and dropping funnel was initially charged with 447 g (3 mol) of butyl ethylphosphonite (produced as in Example 2) and 159 g (3 mol) of acrylonitrile. While stirring, 15 ml of sodium butoxide (30% strength in butanol) are added dropwise at such a rate that a reaction temperature of max. 120° C. becomes established. The crude product thus obtained is distilled in vacuo to obtain 548 g (90% of theory) of butyl ethyl(2-cyanoethyl)phosphinate as colorless liquid.

Workup

  1. customA 1 l five-neck flask equipped with thermometer
  2. temperaturereflux condenser, high-performance stirrer
  3. custom120° C.
  4. customThe crude product thus obtained
  5. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-4617faedb40d4a5fa98f10c540e51397
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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