Catalyst – solid sorbent – or support therefor: product or process – Catalyst or precursor therefor – Organic compound containing
Patent
1997-09-24
1999-09-28
Richter, Johann
Catalyst, solid sorbent, or support therefor: product or process
Catalyst or precursor therefor
Organic compound containing
548545, 548549, 548551, 548552, 502152, B01J 3112, C07D207404, C07D207448, C07D20712
Patent
active
059588217
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to an oxidation catalytic system, which is useful for oxidation of a substrate with oxygen to produce a corresponding oxide with high efficiency, and to a process for oxidation (or a process for producing a ketone, an alcohol, an aldehyde or a carboxylic acid) using this catalytic system.
BACKGROUND TECHNOLOGY
An oxidation reaction is a most basic reaction in the field of industrial organic chemistry, and there are a variety of known oxidation processes, in particular an oxidation process for a substrate using nitric acid. By way of illustration, adipic acid that is a raw material for the production of nylon 66 is prepared by a process of oxidizing cyclohexanol and no other, or a mixture of cyclohexanol and cyclohexane (KA oil) with nitric acid. A long-chain dicarboxylic acid (e.g., suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid) is produced by a process of oxidizing a corresponding macrocyclic (large-ring) cycloalkane (e.g., cyclooctane, cyclononane, cyclodecane, cyclododecane) with the use of nitric acid, and such a long-chain dicarboxylic acid is employed as a raw material for the production of polyesters or polyamides.
Each of these processes, however, requires an expensive exhaust gas treatment plant for treatment of N.sub.2 O and NO.sub.x produced by the oxidation with nitric acid.
In view of these problems, production processes for adipic acid by oxidative carbonylation of butadiene or carbon monoxide (CO) insertion technology have been investigated. These technologies, however, are insufficient for commercial production.
A preferred oxidation process from the viewpoints of resources and environment is a catalytic oxidation, which is conducted with direct use of molecular oxygen or air as an oxidizing agent. Therefore, there has been investigated an oxidation process, which comprises contacting a substrate catalytically and directly with molecular oxygen in the presence of a cobalt catalyst or a boric acid catalyst. By way of example, an oxidation process has been examined, which comprises direct and catalytic contact of cyclohexane, a macrocyclic cycloalkane, or other cycloalkanes or cycloalkenes with molecular oxygen in the presence of a cobalt catalyst or a boric acid catalyst. The use of the cobalt catalyst in the catalytic system, however, requires recovery of the expensive cobalt catalyst, or results in precipitation of the cobalt catalyst. Further, such a catalytic oxidation requires a high temperature and/or a high pressure for activation of oxygen, and the process has still insufficient transformation rate and selectivity. Moreover, to retain the selectivity in a high level, the production process of adipic acid requires to form adipic acid with suppressing the transformation rate or conversion at about 10%. Therefore, according to the catalytic oxidation, commercially satisfactory conversion and selectivity would not be expected in the production of an oxide (e.g., adipic acid, cyclohexenol, cyclohexene) from a corresponding substrate (e.g., cyclohexane or other cycloalkanes, cycloalkenes) under mild conditions.
As for oxidation of a macrocyclic cycloalkane, Japanese Patent Publication No. 3100/1968 (JP-B-43-3100) discloses a production process of lactam, which is used as a raw material for the production of nylon 12. This process comprises the steps of oxidizing cyclododecane with air in the presence of a boric acid catalyst, dehydrogenating cyclododecanol of the products to give cyclododecanone, and reacting cyclododecanone with nitrosylsulfuric acid by Beckmann's rearrangement. However, the macrocyclic cycloalkane is stabler and less reactive than cyclohexane. Accordingly, the conversion of cyclododecane is so small, in the above oxidation process using air, that a yield of cyclododecanone is still insufficient even inclusive of cyclododecanol. In particular, according to the catalytic oxidation commercial production of an oxide (e.g., a carbonyl compound or a carboxylic acid) would not be expected with high yield and high ef
REFERENCES:
patent: 5030739 (1991-07-01), Foricher et al.
Ozaki, Shigeko et al., Epoxidation Catalysed by MnIIITPPCL, J. Chem. Soc., Perkin Trans. II, pp. 951-956, Dec. 1989.
Kouichi et al, "Aerobic Oxidation Using Vanadomolybdophosphate (NPV.sub.6 Mo.sub.6 ) N-Hydroxyphthalimide System", the 67th Spring Annual Meeting of Chemical Society of Japan (1994) pp. 1-4.
Ishii Yasutaka
Nakano Tatsuya
Daicel Chemical Industries Ltd.
Keating Dominic
Richter Johann
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