1,2-Diethenylbenzene → Tetraisopropyl methylenediphosphonate

HRID 727424Notes

Reaction equation

HRID 727424 reaction equation
C(C1C=CC=CC=1C=C)=C.[CH2:11]([P:22](=[O:31])([O:27][CH:28]([CH3:30])[CH3:29])[O:23][CH:24]([CH3:26])[CH3:25])[P:12](=[O:21])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15].[Na].[P]>C1(C)C=CC=CC=1>[CH2:11]([P:12](=[O:21])([O:13][CH:14]([CH3:16])[CH3:15])[O:17][CH:18]([CH3:20])[CH3:19])[P:22](=[O:31])([O:27][CH:28]([CH3:29])[CH3:30])[O:23][CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 666661,2-DiethenylbenzeneHCID 5462309PhosphorusHCID 86751980HCID 86751980, compound

Product 1

HCID 74266Tetraisopropyl methylenediphosphonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Insoluble, cross-linked copolymer beads (70.7 g) obtained by suspension polymerization of 90.5 weight percent vinylbenzyl chloride, 2.0 weight percent divinylbenzene, and 0.5 weight percent benzoyl peroxide (with the ethylstyrenes present in the technical grade divinylbenzene) were placed in a three neck found bottom flash and preswollen with 500 mL of toluene for two hours at room temperature. To this flask, a solution of sodium tetraisopropyl methylenediphosphonate, prepared as in Example 1, was added. The mixture was reacted at reflux for 20 hours. After that time, beads were separated and washed with toluene, and dried. The polymer contained 3.34 mmol of phosphorus/g of dry weight as determined by elemental analysis.

Workup

  1. customfor two hours
  2. customat room temperature
  3. additionwas added
  4. customThe mixture was reacted
  5. temperatureat reflux for 20 hours
  6. customAfter that time, beads were separated
  7. washwashed with toluene
  8. customdried

Sources & evidence

ORD record
ord-f91723fec8e5405dacfed4a47f0fab72
Source dataset
uspto-grants-1998_01
Patent number
US05712347

Reaction notes

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