Patents by Inventor Naruhisa Hirai
Naruhisa Hirai has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 8410308Abstract: 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 —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.Type: GrantFiled: February 27, 2009Date of Patent: April 2, 2013Assignee: Daicel Chemical Industries, Ltd.Inventors: Minoru Takano, Naruhisa Hirai, Yasutaka Ishii
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Patent number: 7994330Abstract: 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° C. or higher.Type: GrantFiled: March 22, 2006Date of Patent: August 9, 2011Assignee: Daicel Chemical Industries, Ltd.Inventors: Naruhisa Hirai, Jun Kuwana
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Patent number: 7910749Abstract: 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.Type: GrantFiled: February 22, 2006Date of Patent: March 22, 2011Assignee: Daicel Chemical Industrial, Ltd.Inventors: Yasuteru Kajikawa, Naruhisa Hirai, Jun Kuwana
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Publication number: 20100331569Abstract: 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 —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.Type: ApplicationFiled: February 27, 2009Publication date: December 30, 2010Inventors: Minoru Takano, Naruhisa Hirai, Yasutaka Ishii
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Publication number: 20100317869Abstract: To provide a solid catalyst containing a cyclic imide skeleton which is easily available and easily separable from reaction products and which is easily recovered and regenerated, and free from reaction inhibitory factors; and a process for oxidation of organic compounds with the solid catalyst. An immobilized cyclic imide catalyst having a structure represented by following Formula (1), wherein X is oxygen or an —OR group (wherein R is hydrogen atom or a hydroxyl-protecting group); n is 0 or 1; Z1 is a five- or six-membered cyclic imide skeleton to which an aromatic or nonaromatic ring Z2 may be adjacent; elliptically shaped moiety S is an inorganic support; A1 is a group linking silicon atom with the cyclic imide skeleton Z1 or with the ring Z2 and is either a divalent hydrocarbon group or a group composed of a divalent hydrocarbon group and an amide bond (—NHCO—); and the cyclic imide skeleton Z1 and the ring Z2 may each be substituted.Type: ApplicationFiled: February 28, 2008Publication date: December 16, 2010Inventors: Yasutaka Ishii, Minoru Takano, Naruhisa Hirai
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Patent number: 7759515Abstract: 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.Type: GrantFiled: May 16, 2006Date of Patent: July 20, 2010Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Naruhisa Hirai, Masahiko Terada
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Patent number: 7741514Abstract: 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.Type: GrantFiled: August 15, 2006Date of Patent: June 22, 2010Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano, Takahiro Iwahama, Naruhisa Hirai
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Patent number: 7524986Abstract: 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 —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.Type: GrantFiled: February 23, 2005Date of Patent: April 28, 2009Assignee: Daicel Chemical Industries, Ltd.Inventors: Naruhisa Hirai, Masahiko Terada
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Publication number: 20080269507Abstract: 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.Type: ApplicationFiled: February 22, 2006Publication date: October 30, 2008Inventors: Yasuteru Kajikawa, Naruhisa Hirai, Jun Kuwana
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Publication number: 20080171881Abstract: 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° C. or higher.Type: ApplicationFiled: March 22, 2006Publication date: July 17, 2008Inventors: Naruhisa Hirai, Jun Kuwana
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Patent number: 7288649Abstract: 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.Type: GrantFiled: September 23, 2005Date of Patent: October 30, 2007Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Naruhisa Hirai
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Patent number: 7285684Abstract: A reaction mixture obtained by reacting a substrate in the presence of an imide compound having an imide unit represented by the formula (1) 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.Type: GrantFiled: March 30, 2001Date of Patent: October 23, 2007Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroyuki Miura, Hitoshi Watanabe, Akihiro Kuwana, Mami Shimamura, Naruhisa Hirai
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Publication number: 20070191634Abstract: 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 —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.Type: ApplicationFiled: February 23, 2005Publication date: August 16, 2007Inventors: Naruhisa Hirai, Masahiko Terada
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Publication number: 20060281629Abstract: 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.Type: ApplicationFiled: August 15, 2006Publication date: December 14, 2006Inventors: Yasutaka Ishii, Tatsuya Nakano, Takahiro Iwahama, Naruhisa Hirai
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Publication number: 20060241293Abstract: A process produces an N,N?,N?-trisubstituted isocyanuric acid represented by following Formula (4): wherein R is a hydroxyl-protecting group, by heating an N-substituted carbamic acid derivative represented by following Formula (1): wherein R has the same meaning as defined above; and Z is a group represented by following Formula (2) or (3): wherein R? is a hydrocarbon group or a heterocyclic group having a carbon atom at the bonding site with the adjacent oxygen atom, wherein the heating is carried out at a temperature in a range of 95° C. to 145° C. where Z is the group represented by Formula (3). This process can easily and conveniently produce the N,N?,N?-trisubstituted isocyanuric acid in a high yield.Type: ApplicationFiled: August 12, 2004Publication date: October 26, 2006Inventor: Naruhisa Hirai
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Publication number: 20060229196Abstract: 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.Type: ApplicationFiled: May 16, 2006Publication date: October 12, 2006Inventors: Yasutaka Ishii, Naruhisa Hirai, Masahiko Terada
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Patent number: 7115541Abstract: 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.Type: GrantFiled: November 8, 2001Date of Patent: October 3, 2006Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano, Takahiro Iwahama, Naruhisa Hirai
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Patent number: 7091342Abstract: 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.Type: GrantFiled: December 5, 2002Date of Patent: August 15, 2006Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Naruhisa Hirai
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Publication number: 20060030716Abstract: 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.Type: ApplicationFiled: September 23, 2005Publication date: February 9, 2006Inventors: Yasutaka Ishii, Naruhisa Hirai
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Patent number: RE39744Abstract: In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2): wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n=1 to 3; or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.Type: GrantFiled: March 5, 1998Date of Patent: July 24, 2007Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai