Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1991-10-17
1993-05-11
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568426, 568449, 568485, C07C 4700, C07C 4527
Patent
active
052103170
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Technical Field
The present invention relates to a method of manufacturing aldehyde by oxidizing a primary alcohol into the corresponding aldehyde, and more particularly, to an improvement in said method using a heterogeneous catalyst.
2. Background Art
In general, a serious difficulty is involved in the production of aldehyde by the oxidation reaction of primary alcohol. This difficulty is in good contrast to the ketone production by the oxidation of secondary alcohol, which can be achieved relatively easily by utilizing the Oppenauer oxidation.
Known methods of producing an aldehyde by the oxidation of a primary alcohol include, for example, the Collins oxidation disclosed in Tetrahedron Letters, p. 3363, 1968 and the DMSO-DCC method disclosed in Journal of the American Chemical Society, Vol. 85, 1963. However each of these known methods necessitates troublesome operations for purifying the product after the reaction. In addition, it is difficult to recover and re-use the reaction reagent, giving rise to serious air pollution or water contamination problems.
When it comes to the Oppenauer oxidation with a homogeneous catalyst system, a method of converting a primary alcohol into the corresponding aldehyde using aluminum isopropoxide as a catalyst in the presence of quinone acting as an oxidizing agent is known, as disclosed in Organic Reactions, Vol. 6, p. 207, 1951. However, it is difficult to re-use the catalyst in this method. Also, troublesome operations are required for the reaction and for the purifying step after the reaction.
In order to overcome the problems noted above, proposed in Published Unexamined Japanese Patent Application No. 1-151532 is a method of producing aldehyde at a high selectivity and a high yield, in which alcohol is reacted with a solid bromite in the presence of alumina or silica gel acting as a heterogeneous catalyst. However, this method is applicable only to benzyl alcohol and derivatives thereof, and thus, is not of sufficient practical value.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a method of producing an aldehyde at a high selectivity and a high yield, in which a primary alcohol is oxidized in the presence of a heterogeneous catalyst which can be used again without difficulty.
To achieve this object, the present invention provides a method of producing an aldehyde, characterized in that a primary alcohol is reacted with an oxidizing agent selected from the group consisting of ketone, aldehyde and quinone in the presence of a partially dehydrated zirconium hydroxide, said reaction being carried out in a diluent which does not participate in the reaction, so as to oxidize the primary alcohol into the corresponding aldehyde.
DETAILED DESCRIPTION OF THE INVENTION
Specifically, what is most important in the present invention is that a partially dehydrated zirconium hydroxide is used as a heterogeneous catalyst. Naturally, it is important to describe first the partially dehydrated zirconium hydroxide used in the present invention.
If heated at about 500.degree. C., zirconium hydroxide is completely dehydrated to form zirconia (ZrO.sub.2). However, if heated at about 300.degree. C. under atmospheric pressure, zircomium hydroxide is partially dehydrated to form a stable state. To be more specific, if the heat treatment is applied to zirconium hydroxide under the intermediate conditions noted above, about 17% of weight reduction takes place in the zirconium hydroxide within about 1 hour of the heat treatment. However, no substantial weight reduction takes place thereafter. The heat treatment for obtaining this particular state of the zirconium compound is not restricted to the above condition, and may be performed under a relatively wide range of conditions. For example, it is possible to apply heating at about 80.degree. C. under a reduced pressure to obtain the same result. The partially dehydrated zirconium hydroxide thus obtained is in the form of a hard, white solid particle. Since the white solid par
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Kuno Hideyuki
Matsushita Hajime
Shibagaki Makoto
Takahashi Kyoko
Japan Tobacco Inc.
Lone Werren B.
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