Oxygen → Benzophenone

HRID 1181662Notes

Reaction equation

HRID 1181662 reaction equation
[C:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14]N1C(=O)C2=CC=CC=C2C1=O.O=O>C(O)(=O)C>[C:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:14])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 7580DiphenylmethaneHCID 10665N-Hydroxyphthalimide

Product 1

HCID 3102BenzophenoneYield 801.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing 168 g (1 mol) of diphenylmethane, 16 g (0.1 mol) of N-hydroxyphthalimide, and 1000 mL of acetic acid was allowed to react at 100° C. for 20 hours in an atmosphere of oxygen to obtain a reaction mixture containing 146 g of benzophenone (yield 80%). From the reaction mixture, acetic acid was distilled off, and to the reaction mixture were added 1000 mL of dibutyl ether and 1000 mL of 0.4N sodium hydroxide aqueous solution. After stirring at 97° C. for 1 hour, an aqueous phase and an organic phase were separated. To the resulting organic phase was further added sodium hydroxide aqueous solution, and mixed completely at 97° C. to liquid-separate into an aqueous phase and an organic phase. The aqueous and organic phases were analyzed by gas chromatography and liquid chromatography, and, as a result, the extraction ratio of benzophenone into the organic phase was 89%, the extraction ratio of the oxidation catalyst and/or the deactivated oxidation catalyst (conversion into sodium phthalate) (on basis of the amount of N-hydroxyphthalimide used in the reaction) into the aqueous phase was 83%.

Workup

  1. customto obtain a reaction mixture

Sources & evidence

ORD record
ord-a51b4fc17ee14e3a92a85dbc4e05f1d5
Source dataset
uspto-grants-2007_10
Patent number
US07285684B2

Reaction notes

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