Benzenesulfonic Acid → 4-Aminostyrene

HRID 1858057Notes

Reaction equation

HRID 1858057 reaction equation
N[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:10]([O-])=O.[Na+].C1(S(O)(=O)=O)C=CC=CC=1.C=CC1C=CC=CC=1>C(O)C.O>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH:3]=[CH2:2])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 7501StyreneHCID 155076Ethenamine, 2-phenyl-HCID 23668193Sodium Nitrite

Product 1

HCID 737004-Aminostyrene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The diazonium salt of 4-aminostyrene is prepared as above from 3.6 g aminostyrene, 2.1 g sodium nitrite, and 150 g water. Ethanol, 10 g, is added to completely dissolve the diazonium salt. A solution of SA-treated MMC is added to the diazonium salt solution, and it is allowed to react for 18 hours under mixing. The solution is filtered to provide MMC solution at about 11 wt %. This MMC contains both benzenesulfonic acid and styrene functionalities covalently attached to the MMC particle. Purification through soxhlet extraction enable higher levels of 4-aminostyrene to be added to the MMC surface.

Workup

  1. customto react for 18 hours
  2. additionunder mixing
  3. filtrationThe solution is filtered
  4. customto provide MMC solution at about 11 wt %
  5. customPurification
  6. extractionthrough soxhlet extraction
  7. additionto be added to the MMC surface

Sources & evidence

ORD record
ord-9880e214866b413eb41201addda6a3c6
Source dataset
uspto-grants-2000_11
Patent number
US06150433

Reaction notes

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