Ethylene Oxide → Bis(2-chloroethyl) P-(2-chloroethyl)phosphonate

HRID 2394934

Reaction equation

[CH:1](P(=O)(O)O)=[CH2:2].P(Cl)(Cl)[Cl:8].C1OC1.[P:14]([O:23][CH2:24][CH2:25][Cl:26])([O:19][CH2:20][CH2:21][Cl:22])[O:15]CCCl>>[Cl:8][CH2:1][CH2:2][P:14](=[O:15])([O:19][CH2:20][CH2:21][Cl:22])[O:23][CH2:24][CH2:25][Cl:26]

Participants

Reactant 4

HCID 6354Ethylene Oxide

HCID 8783Tris(2-chloroethyl) phosphite

HCID 24387Phosphorus trichloride

HCID 168725Poly(vinylphosphonic acid)

Product 1

HCID 80518Bis(2-chloroethyl) P-(2-chloroethyl)phosphonate

Procedure

Vinylphosphonic acid, CH2 =CH--PO(OH)2, can be prepared in a known manner by the following method: Phosphorus trichloride is reacted with ethylene oxide, the resulting tris(2-chloroethyl) phosphite is rearranged to give bis(2-chloroethyl) 2-chloroethylphosphonate, followed by reaction of the bis(2-chloroethyl) 2-chloroethylphosphonate with phosgene in the presence of suitable catalysts to give 2-chloroethylphosphonic dichloride (German Patent No. 2,132,962). The 2-chloroethylphosphonic dichloride can then be converted into vinylphosphonic acid by eliminating HCl in the presence of suitable catalysts (BaCl2) and subsequent hydrolysis of the vinylphosphonic dichloride formed (Chem. Abstr. 54, page 265 (1960)).

Sources & evidence

ORD record: ord-ce39076527824958b65322ad92167cbb
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811575

Linked notes

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