Chloroethane → Ethylene

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

Reactant 3

HCID 6337Chloroethane

HCID 31215Triethyl phosphite

HCID 81365Acetic acid, 2-chloro-, 1,1'-(1,2-ethanediyl) ester

Product 2

HCID 6325Ethylene

HCID 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.