Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1999-08-03
2001-02-20
Vollano, Jean F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S367000, C568S361000
Reexamination Certificate
active
06191312
ABSTRACT:
The present invention relates to a catalytic process for the selective oxidation of a bicyclooctanol to give a bicyclooctanone using an active-carbon-supported heteropolymetallate anion catalyst. In particular, the invention relates to oxidizing 1,5-dimethylbicyclo[3.2.1]octan-8-ol to the ketone using oxygen, oxygen-containing gases or air.
BACKGROUND OF INVENTION
Various processes are known for oxidizing secondary alcohols to give ketones. However, these conventional oxidation processes are associated with numerous disadvantages, e.g.
the use of relatively expensive oxidizing agents in stoichiometric quantities or even in excess,
the separation and disposal of used and unused oxidizing agent,
the production of salts, creating disposal costs and making isolation of the product more difficult,
high pressures,
low selectivity, and
lack of complete conversion.
Examples of known established processes are the Oppenauer oxidation using Al systems and the H
2
O
2
oxidation using Ti, Mo and V systems, and transfer (de)hydrogenations.
The conventional processes are therefore frequently expensive and energy-intensive and burdened by considerable material separation problems in the isolation of the product from a complex reaction mixture. It is often difficult to dispose of oxidizing agents and auxiliary chemicals without harming the environment.
An object of the present invention was to provide a process for the selective oxidation of bicyclooctanols to the ketones which avoids the disadvantages of conventional oxidations, has low costs and is environmentally acceptable.
An oxidation process has now been found which uses an active-carbon-supported catalyst comprising a heteropolymetallate anion and which, under mild reaction conditions and even at atmospheric pressure, can use inexpensive oxidizing agents, such as oxygen-containing gases and even air,
and can achieve high conversions and even complete conversion with high selectivities
and without producing salts.
SUMMARY OF THE INVENTION
The present invention therefore provides a process for preparing a bicyclooctanone, in particular 1,5-dialkylbicyclo[3.2.1]octan-8-one, by reacting a bicyclooctanol, in particular 1,5-dialkylbicyclo[3.2.1]octan-8-ol, with
a. a catalyst applied to an active-carbon support and comprising heteropolyoxometallate anions of vanadium, molybdenum and phosphorus, and also a corresponding alkali-metal, alkaline-earth-metal and/or ammonium counter ion, and
b. a gaseous, oxygen-containing oxidizing agent.
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Alexander Heinz
Dingerdissen Uwe
Hagemeyer Alfred
Kuhlein Klaus
Schulz Rolf Peter
Aventis Research & Technologies GmbH & Co. KG
Frommer & Lawrence & Haug LLP
Vollano Jean F.
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