Daicel Chemical Industries, Ltd.

Other

Yasutaka Ishii

Daicel Corporation

Diacel Chemical Industries, Ltd.

Daicel Corporation Industries, Ltd.

San-petrochemicals Co., Ltd.

Tatsuya Nakano

Naruhisa Hirai

Takahiro Iwahama

Keizo Inoue

Satoshi Sakaguchi

Shinya Nagano

Masahiko Terada

Naoto Okuyama

Takamasa Suzuki

Yoshinori Funaki

Yasuteru Kajikawa

Ichiro Takase

Yoshiya Narasaki

Atsuo Tatsumi

Minoru Takano

Naruhisa Hiral

Tatsuya Research Center Daicel Chemical IndLtd Nakano

Provided is a method of oxidizing a substrate with excellent oxidizing power to yield a corresponding oxide. The method can employ a commercially available imide compound as intact as a catalyst and can produce the oxide in a high yield under mild conditions. A method for producing an oxide according to the present invention includes performing oxidation of a substrate in the presence of oxygen and ozone under catalysis of an imide compound to yield a corresponding oxide. The imide compound has a cyclic imide skeleton represented by Formula (I). In the formula, n is selected from 0 and 1; and X is selected from an oxygen atom and an &#x2014;OR group, where R is selected from hydrogen and a hydroxy-protecting group. 

Method for producing oxide

A process produces an amide or lactam by subjecting an oxime compound to rearrangement in a solvent in the presence of: at least one catalyst selected from the group consisting of an aromatic compound (A1) containing a leaving group bound to a carbon atom constituting the aromatic ring, the aromatic ring including, as a constitutive atom thereof, a heteroatom or including, as a constitutive atom thereof, a carbon atom bound to an electron-withdrawing group, and a compound (A2) containing a structure of Formula (1): -G-L(1) wherein G represents P, N, S, B or Si atom; and Lrepresents a leaving group, wherein G is bound to one or more atoms or groups in addition to L; and a co-catalyst including a halogen-containing organic acid, to give the corresponding amide or lactam, wherein, when the aromatic compound (A1) alone is used as the catalyst, the solvent is at least one solvent selected typically from hydrocarbon solvents. The production process can yield amides or lactams simply in high yields without causing large amounts of by-products such as ammonium sulfate.

Process for producing amide or lactam

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

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

A vinyl- or allyl-containing compound represented by following Formula (3): wherein R, R, R, R, and Reach represent hydrogen atom or a nonmetallic atom-containing group; Rrepresents a nonmetallic atom-containing group; Y represents a group selected from the group consisting of &#x2014;Si(R)(R)&#x2014;, &#x2014;Si(R)(R)&#x2014;O&#x2014;, the left hand of which is combined with R, and &#x2014;NR&#x2014;, wherein R, R, R, R, and Reach represent hydrogen atom or a nonmetallic atom-containing group; and 'n' represents 0 or 1, is prepared by reacting a vinyl or allyl ester compound represented by following Formula (1): wherein Rrepresents hydrogen atom or a nonmetallic atom-containing group; R, R, R, R, R, and 'n' are as defined above, with a compound represented by following Formula (2):R&#x2014;Y&#x2014;H &#x2003;&#x2003;(2)wherein Rand Y are as defined above, in the presence of a transition element compound.

Process for the preparation of vinyl- or allyl-containing compounds

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

A carbonyl compound represented by following Formula (1): wherein Rrepresents hydrogen atom or an organic group; and Rrepresents hydrogen atom or an organic group having a carbon atom at a bonding site with the carbonyl group in Formula (1), wherein Rand Rmay be combined to form a ring with adjacent two carbon atoms, or an equivalent thereof is reacted with an unsaturated compound represented by following Formula (2): wherein each of R, R, and Rrepresents hydrogen atom, a halogen atom, hydroxyl group, or an organic group and wherein Rand Rmay be combined to form a ring with adjacent two carbon atoms, or a precursor thereof, to yield a furan compound represented by following Formula (3): wherein R' represents R, Ror hydrogen atom; and R, R, R, R, are Rare as defined above.

Process for the preparation of furan compounds

A process produces an aromatic compound by bringing an aromatic compound (B) into contact with molecular oxygen (C) in the presence of a catalyst (A) comprising at least one of (A1) a heteropolyacid and/or a salt thereof, and (A2) a mixture of oxoacids and/or salts thereof containing, as a whole, one of P and Si and at least one selected from V, Mo and W to thereby yield another aromatic compound (G) than the aromatic compound (B). The process can produce, for example, a corresponding aromatic hydroxy compound (G1) by allowing the aromatic compound (B) to react with the molecular oxygen (C) further in the presence of a reducing agent (D).

Process for producing aromatic compounds

A catalyst includes a cyclic imide compound having an N-substituted cyclic imide skeleton represented by following Formula (I): wherein X is an oxygen atom or a hydroxyl group, and having a solubility parameter of less than or equal to 26 [(MPa)] as determined by Fedors method. The catalyst may further comprise a metallic compound. By allowing (A) a compound capable of forming a radical to react with (B) a radical scavenging compound in the presence of the catalyst, an addition or substitution reaction product between the compound (A) and the compound (B) or a derivative thereof can be obtained.

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

An allyl-containing compound represented by following Formula (3): wherein R, R, R, Rand Rmay be the same as or different from one another and each represent hydrogen atom or an organic group; Rrepresents an organic group; and Y represents oxygen atom or sulfur atom, is produced by reacting an allyl ester compound represented by following Formula (1): wherein Rrepresents hydrogen atom or an organic group; and R, R, R, Rand Rare as defined above, with a compound represented by following Formula (2):R&#x2014;Y&#x2014;H&#x2003;&#x2003;(2)wherein Ris an organic group; and Y is as defined above, in the presence of at least one transition element compound.

Process for producing allyl-containing compounds

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

An aromatic compound (C) is reacted with carbon monoxide (D) and molecular oxygen (E) in the presence of a palladium compound catalyst (A) and a catalyst (B) and thereby yields a aromatic carboxylic acid corresponding to the aromatic compound (C) except with one or more carboxyl groups bonded to its aromatic ring. The catalyst (B) contains a heteropolyacid or a salt thereof (B) or a mixture of oxo acids and/or salts thereof (B), and the mixture (B) contains, as a whole, one of P and Si and at least one selected from V, Mo and W.

Process for producing aromatic carboxylic acids

A process produces vinyl ether compounds and includes allowing a vinyl ester compound represented by following Formula (1): wherein R, R, Rand Rare the same or different and are each a hydrogen atom or an organic group, to react with a hydroxy compound represented by following Formula (2):ROH&#x2003;&#x2003;(2)wherein Ris an organic group, in the presence of at least one transition element compound to thereby yield a vinyl ether compound represented by following Formula (3): wherein R, R, Rand Rhave the same meanings as defined above. Such transition element compounds include iridium compounds and other compounds containing Group VIII elements.

Process for producing vinyl ether compounds

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

Adamantane derivatives and process for producing them

(A) A compound capable of forming a stable radical and selected from (A1) oxygen-atom-containing compounds each having a carbon-hydrogen bond at the adjacent position to an oxygen atom, (A2) carbonyl-group-containing compounds, and (A3) compounds each having a hydrocarbon group with a methine carbon atom is allowed to react with (B) a radical scavenging compound selected from, for example, (B1) unsaturated compounds, and (B2) compounds each having a hydrocarbon group with a methine carbon atom, in the presence of molecular oxygen by catalysis of, for example, an imide compound shown by the following formula (1): wherein each of Rand Ris a hydrogen atom or the like, where Rand Rmay be combined to form a double bond, or an aromatic or non-aromatic ring; X is an oxygen atom or a hydroxyl group, to yield a product of an addition or substitution reaction of the compound (A) and the compound (B) or its oxidized product. The process can efficiently produce a variety of organic compounds by an addition or substitution reaction using molecular oxygen under mild conditions.

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Takatsuki, Japan

Yasutaka Ishii