Process for catalytic hydroxylation of aromatic hydrocarbons

Details Process for catalytic hydroxylation of aromatic hydrocarbons Process for catalytic hydroxylation of aromatic hydrocarbons

2000-04-27

2002-08-20

Barts, Samuel (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S800000

Reexamination Certificate

active

06437197

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a process for oxidizing aromatic compounds using an oxidant over an oxidizing catalyst under catalytic distillation conditions. More particularly, the present invention relates to hydroxylating aromatics using an oxidizing gas over a molecular sieve catalyst under catalytic distillation conditions.
BACKGROUND OF THE INVENTION
Various methods are known to produce hydroxylated aromatic compounds. The majority of such processes require either the purchase or the formation of an aromatic compound bearing a substituent besides a hydroxyl group. That preexisting substituent then is converted to a hydroxyl group. Direct hydroxylation of aromatic compounds theoretically should be more economical.
Known methods for directly hydroxylating aromatics—particularly for directly converting benzene to phenol—are gas phase processes. In such processes, benzene vapor is partially oxidized at high temperature, typically by reaction with nitrous oxide over a catalyst bed.
Gas phase direct conversion processes are less than ideal for a number of reasons. The energy required to supply the initial heat to begin the reaction is costly. In addition, the reaction of benzene and nitrous oxide is highly exothermic. Expensive, complex system designs may be required to handle the excess heat.
The expense of such reactions is further increased by coke formation from the decomposition products formed at such high temperatures. The average productivity of a catalyst for gas phase oxidation of benzene is only about 4 mmol phenol/g catalyst/hour. The coked catalyst must be regenerated at frequent intervals.
Finally, the reported selectivity of nitrous oxide to phenol in these gas phase processes is low. While selectivities of benzene to phenol of 97-98 mol % are reported, the reported selectivity of nitrous oxide to phenol is only about 85 mol %.
A more economical and efficient process is needed for directly oxidizing aromatic compounds.
SUMMARY OF THE INVENTION
The present invention provides a process comprising contacting an aromatic compound which is at least partially in a liquid phase with an oxidation catalyst and an oxidant under conditions effective to produce a hydroxylated product and an unhydroxylated product, while maintaining the aromatic compound at least partially in a liquid phase.


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