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US 4,301,307 AGranted
Process for the hydroxylation of aromatic compounds
AssigneeRhone-Poulenc Industries
InventorMichel Jouffret
Life of this patent
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Abstract
Aromatic hydrocarbons and particularly phenols and phenol ethers can be hydroxylated by reacting the aromatic compound with hydrogen peroxide in a reaction medium comprising trifluoromethanesulfonic acid. High yields of hydroxylated aromatic compounds are obtained by this process which avoids the use of extremely corrosive and difficult to handle agents. Phenol is hydroxylated predominantly to hydroquinone by this process.
Claims17
A process for the hydroxylation of an aromatic compound having the structural formula:
- ##STR3## wherein R is selected from the group consisting of hydrogen, lower alkyl having from 1 to 3 carbon atoms, and lower alkoxy having from 1 to 3 carbon atoms, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, lower alkyl having from 1 to 3 carbon atoms and hydroxy, with the proviso that, when either R.sub.1 or R.sub.2 is hydroxy, then R is lower alkoxy, which process comprises reacting such organic compound with hydrogen peroxide at a reaction temperature between about -40.degree. and 10.degree. C., in a reaction medium comprising trifluoromethanesulfonic acid, wherein the volume ratio between the trifluoromethanesulfonic acid and the aromatic compound is at least about 0.25, the molar ratio of hydrogen perioxide/aromatic compound is between about 0.025 and 0.3, and the weight of the trifluoromethanesulfonic acid is between about 1 and 30%, to thereby form the hydroxylated aromatic compound reaction product of the following formulae:
- ##STR4## wherein R, R.sub.1, and R.sub.2 are as defined before.
Dependencies are inferred from the claim text.