Chloroethane → Ethylene

HRID 1060201Notes

Reaction equation

HRID 1060201 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH2:7][O:8][C:9](=[O:12])[CH2:10]Cl)=[O:4].[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].[CH2:23](Cl)[CH3:24]>>[CH2:15]([O:14][P:13]([CH2:2][C:3]([O:5][CH2:6][CH2:7][O:8][C:9](=[O:12])[CH2:10][P:13]([O:14][CH2:15][CH3:16])([O:17][CH2:18][CH3:19])=[O:20])=[O:4])([O:20][CH2:23][CH3:24])=[O:17])[CH3:16].[CH2:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6337ChloroethaneHCID 31215Triethyl phosphiteHCID 81365Ethylene bis(chloroacetate)

Product 2

HCID 6325EthyleneHCID 12103002HCID 12103002, compound

Conditions

Temperature
150 °C

Procedure

Ethylene bis[(diethyl phosphono)acetate] was prepared by a modification of the procedure described in U.S. Pat. No. 3,943,200 employing a shorter reaction time and lower final temperature. To ethylene bis(chloroacetate) (107.5 g, 0.5 mol) under nitrogen at 150° C. triethyl phosphite (166.0 g, 1.0 mol) was slowly added over 60 minutes with stirring, and the reaction mixture was maintained at 150° C. for a further 3 hours. Continuous evolution of ethyl chloride occurred throughout the reaction. Removal of volatiles under vacuum gave ethylene bis [(diethyl phosphono) acetates as a straw-coloured liquid (197.5 g, 95%), identified by NMR.

Workup

  1. custom3,943,200 employing a shorter reaction time
  2. customRemoval of volatiles under vacuum

Sources & evidence

ORD record
ord-89ce86b6db8c4c0abe2e0e7e8367c588
Source dataset
uspto-grants-2003_02
Patent number
US06521716B1

Reaction notes

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