Process for producing a cycloalkanol and cycloalkanone

Details Process for producing a cycloalkanol and cycloalkanone Process for producing a cycloalkanol and cycloalkanone

1996-01-30

1998-03-17

Ivy, C. Warren

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

Organic compounds

Oxygen containing

568821, 568835, 568838, 556136, 556137, C07C 4553, C07C 3508, C07F 1500, C07F 1702

Patent

active

057288909

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This is the national stage application of PCT/JP95/01165 filed Jun. 9, 1995 published as WO95/34523 on Dec. 21, 1995.
The present invention relates to a process for producing a cycloalkanol and cycloalkanone at a high yield by decomposing a cycloalkylhydroperoxide in the presence of a catalyst.
The cycloalkanol and cycloalkanone are compounds very useful as materials for producing polyamide polymers, for example, nylon, as intermediates for synthesizing chemical reagents and as organic solvents.


BACKGROUND ART

As a process for producing a cycloalkanol and cycloalkanone by decomposing a cycloalkylhydroperoxide in the presence of a ruthenium catalyst, the process disclosed in Japanese Unexamined Patent Publication (Kokai) No. 61-167631 wherein chromium and ruthenium compounds soluble in the reaction system are used as a decomposition reaction, catalyst, and the process disclosed in Japanese Unexamined Patent Publication (Kokai) No. 63-156735 wherein a ruthenium compound soluble in the reaction system is used together with an isoindolin derivative as a decomposition reaction catalyst, are known.
However, among the conventional processes, the former process is disadvantageous in that where a soluble ruthenium compound such as ruthenium acetylacetonate or ruthenium carboxylate is used alone, the catalyst is degraded during reaction and converted to a precipitate having a low activity, and particularly in a continuous reaction procedure, the reaction rate is significantly reduced. To solve the above-mentioned problems, the ruthenium compound must be used together with a chromium compound which is toxic and thus difficult to handle, and of which the waste liquid requires a complicated treatment to maintain the catalyst at a soluble state. Also, in the latter conventional process, there is a problem that to the above-mentioned soluble ruthenium compound must be added a ligand consisting of an isoindolin derivative, which is expensive. Further, in these conventional processes there is a further problem that the expensive ruthenium catalyst must be employed at a considerably high concentration.
Furthermore, these conventional process have other disadvantages in that when these processes are carried out industrially, since these processes use a soluble ruthenium catalyst, the catalyst must be recovered by a complicated procedure in which a reaction liquid is withdrawn from the reaction system, portions of the residual materials and reaction products are separated by distillation, and thereafter the catalyst contained in the reaction liquid is recycled and reused. In addition to the above-mentioned disadvantage, the conventional processes have another disadvantage in that during the distillation and recycling of the reaction liquid, the catalyst is inevitably deteriorated or precipitated, and thus lost in a great amount, and the continuous reaction by recycling and reusing of the catalyst in the soluble in an activated condition becomes difficult.
In consideration of the above-mentioned technical background, an object of the present invention is to provide a process for forming a cycloalkanol and cycloalkanone from a cycloalkylhydroperoxide in the presence of a small amount of a ruthenium catalyst insoluble in the reaction system and having a high activity at a high reaction rate at a high yield and at a high selectivity (the percentage of the produced target compound based on the total amount of the reaction products).


DISCLOSURE OF THE INVENTION

The process of the present invention for producing a cycloalkanol and cycloalkanone comprises decomposing a cycloalkylhydroperoxide by bringing it into contact with a ruthenium complex represented by the general formula (I): ruthenium atom, n represents an integer of 1 to 4, and m represents an integer of 1 or more.


BEST MODE OF CARRYING OUT THE INVENTION

In the process of the present invention, a cycloalkylhydroperoxide is decomposed by contacting with a catalyst consisting of the specific ruthenium complex of the formula (I), to produce a correspo

REFERENCES:
patent: 3925316 (1975-12-01), Brunie
patent: 4482746 (1984-11-01), Hermolin
patent: 5120886 (1992-06-01), Lyons

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