Method for hydroxylating aromatic compounds
AssigneeGeneral Electric Company
InventorsTerence Michael Barnhart, Annah Waswa Hughes
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Abstract
Aromatic compounds such as benzene, toluene and xylene are hydroxylated by reaction with oxygen and hydroquinone or a substituted hydroquinone in the presence of a vanadium compound, typically a pentavalent vanadium oxy chelate with picolinic acid or a substituted picolinic acid. The vanadium compound may be produced in situ by reaction of the chelating agent with a tetravalent or pentavalent precursor vanadium compound.
Claims22
A method for converting an aromatic compound to a hydroxyaromatic compound which comprises contacting said aromatic compound with molecular oxygen in the presence of a vanadium compound and hydroquinone or an alkyl- or halogen-substituted hydroquinone,
- wherein said aromatic compound is capable of conversion to the hydroxyaromatic compound with a turnover greater than 1 in the presence of said vanadium compound, where turnover is a ratio of moles of hydroxyaromatic compound to gram-atoms of vanadium at a time of completion of a reaction, and
- wherein said vanadium compound is capable of conversion to a hydroxylation reagent in the presence of molecular oxygen and hydroquinone or the alkyl- or halogen-substituted hydroquinone.
A method for converting an aromatic compound to a hydroxyaromatic compound which comprises contacting said aromatic compound with molecular oxygen in the presence of a vanadium compound and hydroquinone or an alkyl- or halogen-substituted hydroquinone,
- wherein said aromatic compound is capable of conversion to the hydroxyaromatic compound with a turnover greater than 1 in the presence of said vanadium compound, where turnover is a ratio of moles of hydroxyaromatic compound to gram-atoms of vanadium at a time of completion of a reaction,
- wherein said vanadium compound is present at a level of about 10 to about 7,500 ppm based on the aromatic compound and said vanadium compound is capable of conversion to a hydroxylation reagent in the presence of molecular oxygen and hydroquinone or the alkyl- or halogen-substituted hydroquinone, and
- wherein a weight ratio of said hydroquinone or the alkyl- or halogen-substituted hydroquinone to the vanadium compound is in a range of about 40:1 to about 1000:1.
A method for converting an aromatic compound to a hydroxyaromatic compound which comprises contacting said aromatic compound with molecular oxygen in the presence of a vanadium compound and hydroquinone or an alkyl- or halogen-substituted hydroquinone in a polar aprotic solvent under a pressure of about 2 MPa to about 5 MPa at a temperature of about 30.degree. C. to about 120.degree. C.,
- wherein said aromatic compound is capable of conversion to the hydroxyaromatic compound with a turnover greater than 1 in the presence of said vanadium compound, where turnover is a ratio of moles of hydroxyaromatic compound to gram-atoms of vanadium at a time of completion of a reaction,
- wherein said vanadium compound is present at a level of about 10 to about 7,500 ppm based on the aromatic compound and said vanadium compound is capable of conversion to a hydroxylation reagent in the presence of molecular oxygen and hydroquinone or the alkyl- or halogen-substituted hydroquinone, and
- wherein a weight ratio of said hydroquinone or the alkyl- or halogen-substituted hydroquinone to the vanadium compound is in a range of about 40:1 to about 1000:1.
Dependencies are inferred from the claim text.