Daicel Chemical Industries, Ltd.

Naruhisa Hirai

Yasutaka Ishii

Tatsuya Nakano

Takahiro Iwahama

Masahiko Terada

Jun Kuwana

Hiroyuki Miura

Yasuteru Kajikawa

Hitoshi Watanabe

Akihiro Kuwana

Minoru Takano

Mami Shimamura

Disclosed is a process for the production of an oxygen-containing organic compound by oxidizing an organic compound with molecular oxygen in a liquid phase in the presence both of a catalytic nitrogen-containing cyclic compound and a catalyst including a solid superacid and, supported thereon, a transition metal compound, in which the nitrogen-containing cyclic compound contains, as a ring constituent, a skeleton represented by following Formula (1), wherein X represents an &#x2014;OR group, and wherein R represents hydrogen atom or a hydroxyl-protecting group. The process gives the oxygen-containing organic compound in a high yield and enables easy recovery and reuse of the catalyst. 

Process for production of oxygen-containing organic compound

It is desirable to provide a method for easily removing catalyst-derived impurities from a product of a reaction by the catalysis of a compound having a dicarboximide skeleton and thereby efficiently yielding a target compound with high purity. Disclosed is a method for producing an organic compound through a reaction of a substrate in the presence of a catalyst, the catalyst including a compound having a dicarboximide skeleton represented by following Formula (i): wherein R represents hydrogen atom or a hydroxyl-protecting group. The method includes the step of treating a reaction product with hot water so as to decompose and remove an impurity derived from the catalyst. The temperature of the hot water is preferably 100&#xb0; C. or higher.

Method for producing organic compound and method for decomposing compound having dicarboximide skeleton

A method oxidizes an organic compound with oxygen in the presence of a catalyst, in which the catalyst contains a N-hydroxy- or N-(substituted oxy)-imide compound derivable from at least one selected from a target product, a reaction intermediate, and a reaction byproduct, and the catalyst is produced from at least one component selected from the target product, reaction intermediate, and reaction byproduct each formed as a result of the reaction and is used in the oxidation reaction so as to make up for a loss of the catalyst due to denaturation in the reaction. The method can easily and inexpensively make up for a loss of the catalyst denaturated in the course of reaction.

Methods for oxidizing organic compounds

A catalyst of the invention includes an imide compound having a N-substituted cyclic imide skeleton represented by following Formula (I): wherein R is a hydroxyl-protecting group. Preferred R is a hydrolyzable protecting group. R may be a group obtained from an acid by eliminating an OH group therefrom. Such acids include, for example, carboxylic acids, sulfonic acids, carbonic acid, carbamic acid, sulfuric acid, nitric acid, phosphoric acids and boric acids. The catalyst may include the imide compound and a metallic compound in combination. In the presence of the catalyst, (A) a compound capable of forming a radical is allowed to react with (B) a radical scavenging compound and thereby yields an addition or substitution reaction product of the compound (A) and the compound (B) or a derivative thereof. This catalyst can produce an organic compound with a high selectivity in a high yield as a result of, for example, an addition or substitution reaction under mild conditions.

Catalyst comprising N-substituted cyclic imide compound and process for producing organic compounds using the catalyst

Catalyst comprising N-substituted cyclic imide compound and process for producing organic compound using the catalyst

A method of this invention produces an aromatic carboxylic acid, by oxidizing an aromatic compound B with oxygen in the presence of a catalytic nitrogen-containing cyclic compound A to thereby yield a corresponding aromatic carboxylic acid, the aromatic compound B having one or more hydrocarbon groups alone as substituents on its aromatic ring, and the catalytic nitrogen-containing cyclic compound A having a skeleton represented by following Formula (i): wherein X represents oxygen atom or an &#x2014;OR group, and wherein R represents hydrogen atom or a hydroxyl-protecting group, as a constitutive member of its ring. The method includes the step of carrying out a reaction at a concentration of the aromatic compound B in the reaction system of 3.0 percent by weight or less, while continuously feeding the catalytic nitrogen-containing cyclic compound A, the aromatic compound B, a reaction solvent, and oxygen to a reactor and continuously extracting a reaction mixture from the reactor. This method can produce aromatic carboxylic acids with industrially good productivity without the need for special reaction facilities and without undergoing many steps.

Methods for producing aromatic carboxylic acids

A catalyst of the invention includes a cyclic acylurea compound having a cyclic acylurea skeleton represented by following Formula (I): wherein R is a hydrogen atom or a hydroxyl-protecting group; n is 1 or 2; G is a carbon atom or a nitrogen atom, where two Gs are the same or different when n is 2. The catalyst may include the cyclic acylurea compound and a metallic compound in combination. In the presence of the catalyst, (A) a compound capable of forming a radical is allowed to react with (B) a radical scavenging compound and thereby yields an addition or substitution reaction product of the compound (A) and the compound (B) or a derivative thereof. This catalyst can produce an organic compound with a high selectivity in a high yield as a result of, for example, an addition or substitution reaction under mild conditions.

Catalyst comprising cyclic acylurea compound and process for producing organic compounds using the catalyst

A reaction mixture obtained by reacting a substrate in the presence of an imide compound having an imide unit represented by the formula () can be efficiently separated through crystallization and/or extraction with a specific solvent into the imide compound and a reaction product. (In the formula, X represents oxygen, hydroxyl, or acyloxy.) Furthermore, a mixture comprising the imide compound and a metal catalyst can be efficiently separated through crystallization, adsorption, and/or extraction into the imide compound and the metal catalyst.

Process for separating imide compounds

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2):

Adamantane derivatives and process for producing them

Catalyst comprising n-substituted cyclic imides and processes for preparing organic compounds with the catalyst

Catalyst comprising cyclic acylurea compounds and processes for production organic compounds with the same

Process for separating an oxidation reaction product and an oxidation catalyst

An acylating agent of the invention includes (A) a 1,2-dicarbonyl compound or its hydroxy reductant, (B) oxygen, and (C) at least one compound selected from (c1) a metallic compound and (C2) N-hydroxyphthalimide or another imide compound. As the 1,2-dicarbonyl compound or its hydroxy reductant (A), biacetyl, 2,3-butanediolor the like canbeused. As the metallic compound (c1), cobalt acetate, or another cobalt compound, for example, can be employed. By reacting an adamantane derivative or another compound having a methine carbon atom with the acylating agent, an acyl group can be introduced to the methine carbon atom with efficiency.

Methods of acylating adamantane, tricyclo&lsqb;5.2.1.02,6&rsqb;, and decalin compounds

A compound shown by the following formula:

Growing community of inventors

Himeji, Japan

Naruhisa Hirai