Hydrochloric Acid → Biphenyl

HRID 888648Notes

Reaction equation

HRID 888648 reaction equation
C(O[Si](OCC)(OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Si](OCC)(OCC)OCC)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)C.Cl>C(O)C>[C:8]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14951443([1,1'-Biphenyl]-4,4'-diyl)bis(triethoxysilane)

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, trimethyloctadecylammonium chloride (surfactant: 1.83 g, 5.26 mol) was dissolved in a mixed liquid of water (100 ml) and a 6 M aqueous solution of sodium hydroxide (10 g) to obtain a mixed solution. Then, 4,4′-bis(triethoxysilyl)biphenyl (2.00 g, 4.18 mol) was added dropwise into the obtained mixed solution while stirring at room temperature. Thereafter, the irradiation with ultrasonic waves for 20 minutes and the stirring were repeated to the mixed solution. Subsequently, the solution was stirred for 24 hours at room temperature to obtain a reaction solution. After that, the reaction solution was left at rest at a temperature condition of 98° C. for 48 hours. Then, the reaction solution was heated to obtain a silica porous material modified by a biphenyl group (BiPh-HMM) containing the surfactant. Subsequently, BiPh-HMM containing the surfactant was suspended in a mixed liquid containing ethanol (260 ml) and concentrated hydrochloric acid (11.7 g). Thereafter, the suspended liquid was stirred while heating at a temperature condition of 70° C. for 7 hours to extract the surfactant from the BiPh-HMM. After that, the suspended liquid was filtered. Then, the obtained white powders were washed with ethanol and dried in vacuum to obtain BiPh-HMM crystalline powders.

Workup

  1. additionmixed solution
  2. customThereafter, the irradiation with ultrasonic waves for 20 minutes
  3. stirringSubsequently, the solution was stirred for 24 hours at room temperature
  4. customto obtain a reaction solution
  5. temperatureThen, the reaction solution was heated
  6. customto obtain a silica porous material
  7. additioncontaining the surfactant
  8. additionSubsequently, BiPh-HMM containing the surfactant
  9. stirringThereafter, the suspended liquid was stirred
  10. temperaturewhile heating at a temperature condition of 70° C. for 7 hours
  11. extractionto extract the surfactant from the BiPh-HMM
  12. filtrationAfter that, the suspended liquid was filtered
  13. washThen, the obtained white powders were washed with ethanol
  14. customdried in vacuum
  15. customto obtain BiPh-HMM crystalline powders

Sources & evidence

ORD record
ord-a87b196b3a024a2baa56919927a17a85
Source dataset
uspto-grants-2012_08
Patent number
US08247680B2

Reaction notes

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