Methyl Chloride → Tris(2-chloroethyl)Phosphate Dimethyl Methylphosphonate

HRID 28091

Reaction equation

HRID 28091 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][P:5]([O:11][CH2:12][CH2:13][Cl:14])([O:7][CH2:8][CH2:9][Cl:10])=[O:6].[CH3:15][P:16](=[O:21])([O:19][CH3:20])[O:17][CH3:18].CCl.C1OC1>CO>[Cl:1][CH2:2][CH2:3][O:4][P:5]([O:7][CH2:8][CH2:9][Cl:10])([O:11][CH2:12][CH2:13][Cl:14])=[O:6].[CH3:15][P:16](=[O:21])([O:19][CH3:20])[O:17][CH3:18]

Participants

6

Reactant 4

HCID 6327Methyl ChlorideHCID 6354Ethylene OxideHCID 8295Tris(2-chloroethyl) phosphateHCID 12958Dimethyl methylphosphonate

Product 1

HCID 6455455Tris(2-chloroethyl)Phosphate Dimethyl Methylphosphonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 571 g. of tris(2-chloroethyl)phosphate and 531 g. of dimethyl methylphosphonate was heated at 181°-197° C. until 287.5 of methylchloride was evolved; this required 26 hours. The product was then heated at 95° with 28.2 g. of methanol, and finally treated with ethylene oxide at 90°-100° until substantially neutral. The product was useful as a flame retardant at 5-10 phr. in a styrenated polyester.

Workup

  1. additionA mixture of 571 g
  2. custom26 hours
  3. temperatureThe product was then heated at 95° with 28.2 g

Sources & evidence

ORD record
ord-6c0dd0c71ba34c3496def7881425f232
Source dataset
uspto-grants-1980_09
Patent number
US04225522

Linked notes

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