Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1996-12-02
1998-11-24
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568390, C07C 4542
Patent
active
058409920
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a novel process for producing 6-methylheptan-2-one, which is useful as a material for synthesizing (1963)! or as a material for synthesizing fragrances such as (1955)!.
BACKGROUND ART
As processes for producing 6-methylheptan-2-one, processes (i) to (iv) shown below are known in the art. subjected to condensation in the presence of a base, followed by hydrolysis and decarboxylation reaction (see, e.g., "SYNTHETIC ORGANIC CHEMISTRY", p.327, written by Wagner, John Wiley & Sons, Inc.); 6-methyl-3,5-heptadien-2-one is subjected to a hydrogenation reaction in Ser. Knim. (5), 1052 (1972)!; Fr., 1799 (1963)!; and each other in a stream of hydrogen, in the presence of a catalyst containing nickel and/or cobalt and zinc oxide or the like as main components (Japanese Patent Application Laid-open No. 53-22186).
The above processes, however, have problems as discussed below. That is, in the case of the process (i), there are the problems that the starting material (acetoacetic acid ester) is expensive and also the process requires for the condensation the base at least in an equimolar amount with respect to the acetoacetic acid ester, resulting in a high cost for the production of the 6-methylheptan-2-one. In the case of the process (ii), there is the problem that the production of the starting material (6-methyl-5-hepten-2-one or 6-methyl-3,5-heptadien-2-one) itself is complicated. In the case of the process (iii), there are the problems that not only the production of 6-methylhepten-2-ol itself is complicated, but also 85% phosphoric acid and phosphorus pentoxide are used in a large quantity to require much labor for the disposal of waste water. In the case of the process (iv), there is the problem that the reaction must be carried out at high temperatures and under a liquid phase condition, so that it requires special production apparatus.
Thus, although some methods as above are known for the production of 6-methylheptan-2-one, all the methods have subjects to be settled in respect of starting material costs and production apparatus. Under the existing circumstances, no industrially advantageous process has been established for producing 6-methylheptan-2-one.
Objects of the present invention are to solve the problems involved in the prior art discussed above and to provide an industrially advantageous process for producing 6-methylheptan-2-one.
DISCLOSURE OF THE INVENTION
The present inventors have discovered that 6-methylheptan-2-one can be produced efficiently and in an industrially simple manner when isovaleral and acetone, which are produced in an industrial scale and available inexpensively, are used as starting materials and when these are subjected to aldol condensation and the resulting condensate is subjected to hydrogenation under a dehydration condition, and have accomplished the present invention.
More specifically, the present invention provides a process for producing 6-methylheptan-2-one, comprising subjecting isovaleral and acetone to aldol condensation in the presence of a basic substance to form a condensate which contains 4-hydroxy-6-methylheptan-2-one, and subjecting the condensate to hydrogenation reaction under a dehydration condition.
In the present invention, the "condensate which contains 4-hydroxy-6-methylheptan-2-one" refers to a single compound of 4-hydroxy-6-methylheptan-2-one, or a mixture of this compound with at least one compound selected from the group consisting of 6-methyl-3-hepten-2-one, 6-methyl-4-hepten-2-one and 6-methyl-5-hepten-2-one. Hereinafter, unless particularly noted, the "condensate which contains 4-hydroxy-6-methylheptan-2-one" is simply called "4-hydroxy-6-methylheptan-2-one-containing condensate".
BEST MODE FOR WORKING THE INVENTION
The present invention is described below in detail.
In the process for producing 6-methylheptan-2-one of the present invention, first isovaleral and acetone are allowed to react with each other to obtain a 4-hydroxy-6-methylheptan-2-one-containing condensate.
Here, from the viewpoin
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R. T. Morrison, et al., Verlag Chemie GmbH, pp. 768-773, 1978, "Lehrbuch Der Organischen Chemie".
Jerry March, John Wiley & Sons, pp. 937-939, 1992, "Advanced Organic Chemistry".
Iwasaki Hideharu
Kido Yoichi
Kitayama Masahiko
Onishi Takashi
Yoneda Koichi
Kuraray Co. Ltd.
Reamer James H.
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