Abstract:
A process of the present invention produces a corresponding dicarboxylic acid by oxidative cleavage of a cycloalkane with oxygen and performs a reaction in the presence of a catalyst including an imide compound and a metallic compound, the imide compound having a cyclic imide skeleton represented by following Formula (I): wherein X is an oxygen atom or an-OR group, and wherein R is a hydrogen atom or a hydroxyl-protecting group, under conditions of a reaction temperature of 80 DEG C or higher and a concentration of the cycloalkane in a system of 21% by weight or more. The imide compound includes, for example, N-hydroxyphthalimide. The amount of the imide compound is, for example, from about 0.000001 to about 0.01 mole per mole of the cycloalkane. In the production of a corresponding dicarboxylic acid by catalytic oxidation of a cycloalkane with oxygen, the present invention can yield the dicarboxylic acid in a high space time yield even using a small amount of the catalyst.
Abstract:
A process for producing dicarboxylic acids by oxidative cleavage of cycloalkanes with oxygen, characterized in that the oxidative cleavage is conducted in the presence of a catalyst constituted of both an imido compoun d having a cyclic imide skeleton represented by the general formula (I): (I) [wherein X is oxygen or OR (wherein R is hydrogen or a hydroxyl-protecting group)] and a metal compound at a temperature of 80 ~C or above in a reactio n system having a cycloalkane concentration of 21 wt% or above. The imido compound is N-hydroxyphthalimide or the like, and is used in an amount of about 0.000001 to 0.01 mol per mol of the cycloalkane. In producing dicalboxylic acids by catalytic oxygenation of cycloalkanes, this process attains high space time yield even with a reduced amount of a catalyst.
Abstract:
A catalyst comprised of an imide compound having an N-substituted cyclic imide skeleton represented by the general formula (I): (I) (wherein R is a hydroxyl-protecting group). The hydroxyl-protecting group (R) is preferably a hydrolyzable one and examples thereof include groups derived from carboxylic acid, sulfonic acid, carbonic acid, carbamic acid, sulfuric acid, nitric acid, phosphoric acid, boric acid, and so on by the removal of a hydroxyl group. The catalyst may be comprised of a combination of the above imide compound and a metal compound. Reactions of (A) radical-forming compounds with (B) radical -scavenging compounds in the presence of the above catalyst give products of addition or substitution reaction between the compounds (A) and (B) or derivatives thereof. According to the invention, organic compounds can be prepared through addition or substitution reaction or the like under mild conditions with high selectivity in high yield.
Abstract:
An oxidation catalyst system comprising (A) a ruthenium compound and (B) a dihydroxybenzene or an oxidation product thereof. Examples of the ruthenium compound (A) include ruthenium complexes, e.g., dichlorotris(triphenylphosphine)ruthenium(II), and Ru/C. Examples of the dihydroxybenzene or oxidation product (B) include hydroquinone. When an alcohol is oxidized with molecular oxygen in the presence of the oxidation catalyst system, the corresponding carbonyl compound is obtained in a high yield. Primary alcohols are more selectively oxidized than secondary alcohols.
Abstract:
An adamantane derivative having a functional group such as nitro, amino, hydroxyl, carboxyl, hydroxymethyl or isocyanato is oxidized with oxygen in the presence of an imide compound of general formula (2) (such as N-hydroxyphthalimide) or both of this imide compound and a cocatalyst (such as a transition metal compound). This process can efficiently provide an adamantane derivative having a hydroxyl group in addition to the functional group such as nitro, amino, hydroxyl, carboxyl, hydroxymethyl or isocyanato; wherein R?1 and R2¿ each represent hydrogen, halogen, alkyl, aryl or cycloalkyl, or R?1 and R2¿ may be bonded together to form a double bond, or an aromatic or non-aromatic ring; Y represents O or OH; and n represents 1 to 3.
Abstract:
Catalysts comprising imide compounds having N-substituted cyclic imide skeletons as represented by the general formula (I) [wherein R is a hydroxyl-protecting group]. R is preferably a hydrolyzable protective group, e.g., a group derived by removing OH from an acid such as carboxylic acid, sulfonic acid, carbonic acid, carbamic acid, sulfuric acid, nitric acid, phosphoric acid, or boric acid. The catalysts may be constituted of the imide compounds and metal compounds. The reaction of (A) a radical forming compound with (B) a radical scavenging compound in the presence of a catalyst described above can give a product of addition or substitution of the compound (A) with the compound (B) or a derivative thereof. The catalysts enable the production of organic compounds by addition, substitution, or the like under mild conditions with high selectivity in high yield.
Abstract:
A catalyst comprising a cyclic acylurea compound having a cyclic acylurea skeleton represented by the general formula (I): (I) [wherein R is hydrogen or a hydroxyl-protecting group; G is carbon or nitrogen; and n is 1 or 2, with the proviso that when n is 2, two G’s may be the same or different]. The catalyst may consist of a combination of the above cyclic acylurea compound and a metal compound. Reaction of (A) a radical-forming compound with (B) a radical-capturing compound in the presence of the above catalyst gives an addition or replacement product of the compound (B) with the compound (A) or derivatives thereof. According to the invention, organic compounds can be produced through addition or replacement reaction under mild conditions at high selectivity and in high yield.