Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1999-09-24
2000-12-26
Vollano, Jean F
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
502223, 502230, 568424, C07C 4529, B01J 2700
Patent
active
06166264&
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to an oxidation catalyst system which is useful for the production of carbonyl compounds, in particular aldehydes, from alcohols, to a process for the oxidation of alcohols using the oxidation catalyst system, and to a process for the production of carbonyl compounds.
BACKGROUND ART
Oxidizing processes of organic substrates by the use of molecular oxygen as an oxidizing agent, in particular those for oxidizing alcohols to obtain the corresponding carbonyl compounds, are very important in industries of organic chemistry, from the viewpoint of economy and of protecting environment.
Separately, processes for the oxidation of alcohols using a ruthenium compound as a catalyst to give carbonyl compounds have been investigated in different ways. By way of illustration, in J. Chem. Soc., Chem. Commun., 1987, 1625 is proposed a process for the oxidation of an alcohol to give the corresponding carbonyl compound by the use of a catalytic amount of tetrapropylammonium perruthenate and 1.5 equivalents of 4-methylmorpholine-N-oxide with respect to the alcohol. In Bull. Chem. Soc. Jpn., 61, 3607(1988) is proposed a process for the oxidation of allyl alcohol and benzyl alcohol using dichlorotris(triphenylphosphine)ruthenium(II) and two equivalents of bis (trimethylsilyl)peroxide with respect to the alcohols. These processes, however, require large amounts of co-oxidizing agents such as peroxides which need careful handling, and are economically disadvantageous.
In J. Am. Chem. Soc., 1997, 12661 is disclosed a process for the oxidation of an alcohol by molecular oxygen in the presence of a catalytic amount of tetrapropylammonium perruthenate and a molecular sieve to obtain a carbonyl compound. This process, however, requires comparatively large amounts of molecular sieves. In addition, a secondary alcohol is more liable to be oxidized than a primary alcohol in such oxidation reactions of alcohols by oxygen, and such a primary alcohol can hardly be oxidized in a selective manner (see J. Chem. Soc., Chem. Commun., 1994, 1037).
DISCLOSURE OF INVENTION
It is, therefore, an object of the present invention to provide an oxidation catalyst system and an oxidation process through which an alcohol can be efficiently oxidized by molecular oxygen using a small quantity of a catalyst.
It is another object of the invention to provide a process for the production of carbonyl compounds, through which a carbonyl compound can be obtained from the corresponding alcohol in high yield using a small quantity of a catalyst.
A further object of the invention is to provide a process for the selective oxidation of primary alcohols to obtain the corresponding aldehydes in high yields.
After intensive investigations to achieve the above objects, the present inventors found that a combination use of a ruthenium compound and a specific compound can provide, in a catalytic amount, efficient oxidation of alcohols to give the corresponding carbonyl compounds in satisfactory yields. The present invention has been accomplished based upon the above finding.
To be more specific, the present invention provides an oxidation catalyst system being composed of (A) a ruthenium compound and (B) a dioxybenzene or its oxidant.
The invention further provides a process for oxidation, which includes oxidizing an alcohol by molecular oxygen in the presence of the above oxidation catalyst system.
In addition, the invention provides a process for the production of carbonyl compounds, which includes oxidizing an alcohol by molecular oxygen in the presence of the oxidation catalyst system to give the corresponding carbonyl compound.
BEST MODE FOR CARRYING OUT THE INVENTION
The oxidation catalyst system of the invention comprises (A) a ruthenium compound and (B) a dioxybenzene or its oxidant as catalytic components.
[Ruthenium Compound (A)]
The ruthenium compound (A) includes ruthenium-containing compounds, as well as elementary ruthenium. As examples of the ruthenium compound (A), there may be mentioned metallic ruthenium, rut
REFERENCES:
CA:129:202533 abs of Tetrahedron Lett by Hanyu 39(31) pp. 5557-5560, 1998.
CA:115:48976 abs of J Chem Soc Chem Commun by Baeckvall et al (7) pp. 473-5, 1991.
CA:110:153591 abs of Chem Mater. by Stoessel et al 1(2) pp. 259-68, 1989.
CA:121:107581 abs of J Chem Soc Commun by Wang (9) pp. 1037-8, 1994.
Ishii Yasutaka
Nakano Tatsuya
Daicel Chemical Industries Ltd.
Vollano Jean F
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