Acetophenone → Styrylphosphonic acid

HRID 1957372Notes

Reaction equation

HRID 1957372 reaction equation
[P:1]([OH:4])([OH:3])[OH:2].[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)[CH3:6]>>[CH:6]([P:1]([OH:4])(=[O:3])[OH:2])=[CH:5][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 7410AcetophenoneHCID 107909Phosphorous acid

Product 1

HCID 74355Styrylphosphonic acid

Procedure

In this Example, an acid catalyst (ZSM-5-40 zeolite) was used for both the reaction of phosphorous acid (24.6 gm) with 36 gm of acetophenone (at 75° C.) and the subsequent reaction (at 80° C.) to crack the acyl derivative to form SPA. The amount of catalyst used in the first reaction was 12 gm. It was determined that the product contained 77 wt % styrene phosphonic acid (SPA), 17 wt % unreacted phosphorous acid, and 6 wt % Diels-Alder dimer phosphorus compound. The yield of SPA in this reaction was therefore 65% of theory.

Workup

  1. customthe subsequent reaction (at 80° C.)

Sources & evidence

ORD record
ord-f26bbcdfeffa49eab25bf7fd731e638e
Source dataset
uspto-grants-1998_07
Patent number
US05783730

Reaction notes

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