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1. 发明授权

US08163899B2 Process for producing laurolactam 有权
标题翻译：生产月桂内酰胺的方法
公开(公告)号：US08163899B2
公开(公告)日：2012-04-24
申请号：US12526494
申请日：2008-02-08
申请人： Kazuaki Ishihara , Junichi Kugimoto , Joji Kawai
发明人： Kazuaki Ishihara , Junichi Kugimoto , Joji Kawai
IPC分类号： C07D201/04
CPC分类号： C07D201/04 , C07D225/02 , Y02P20/582
摘要： Disclosed is a method for producing laurolactam from cyclododecanone and hydroxylamine in a simple process and with high efficiency. The method comprises the following steps (a) to (e): (a) reacting cyclododecanone with hydroxylamine in an aqueous solution in the presence of an excess amount of cyclododecanone or a solvent to produce cyclododecanone oxime; (b) separating the reaction mixture obtained after the oxime-forming step into an oil and an aqueous phases and collecting a solution of cyclododecanone oxime of the oil phase as; (c) removing dissolved water from the solution of cyclododecanone oxime which is collected as an oily phase in the oil/aqueous phase separation step; (d) producing laurolactam from cyclododecanone oxime by rearrangement reaction using an aromatic-ring containing compound as a rearrangement catalyst; and (e) separating the produced laurolactam from the reaction mixture after the rearrangement step and purifying the laurolactam.
摘要翻译：公开了一种以简单的工艺和高效率从环十二酮和羟胺制备月桂内酰胺的方法。该方法包括以下步骤（a）至（e）：（a）在过量的环十二烷酮或溶剂的存在下，使环十二酮与羟胺在水溶液中反应，生成环十二酮肟; （b）将在肟形成步骤后获得的反应混合物分离成油和水相，并收集油相的环十二酮肟溶液; （c）从在油/水相分离步骤中以油相收集的环十二酮肟溶液中除去溶解的水; （d）使用含芳环的化合物作为重排催化剂，通过重排反应从环十二酮肟生产月桂内酰胺; 和（e）在重排步骤之后将所生产的月桂内酰胺与反应混合物分离并纯化十二内酰胺。

2. 发明申请

US20100324283A1 PROCESS FOR PRODUCING LAUROLACTAM 有权
标题翻译：生产乳酸菌的方法
公开(公告)号：US20100324283A1
公开(公告)日：2010-12-23
申请号：US12526494
申请日：2008-02-08
申请人： Kazuaki Ishihara , Junichi Kugimoto , Joji Kawai
发明人： Kazuaki Ishihara , Junichi Kugimoto , Joji Kawai
IPC分类号： C07D225/02
CPC分类号： C07D201/04 , C07D225/02 , Y02P20/582
摘要： Disclosed is a method for producing laurolactam from cyclododecanone and hydroxylamine in a simple process and with high efficiency. The method comprises the following steps (a) to (e): (a) reacting cyclododecanone with hydroxylamine in an aqueous solution in the presence of an excess amount of cyclododecanone or a solvent to produce cyclododecanone oxime; (b) separating the reaction mixture obtained after the oxime-forming step into an oil and an aqueous phases and collecting a solution of cyclododecanone oxime of the oil phase as; (c) removing dissolved water from the solution of cyclododecanone oxime which is collected as an oily phase in the oil/aqueous phase separation step; (d) producing laurolactam from cyclododecanone oxime by rearrangement reaction using an aromatic-ring containing compound as a rearrangement catalyst; and (e) separating the produced laurolactam from the reaction mixture after the rearrangement step and purifying the laurolactam.
摘要翻译：公开了一种以简单的工艺和高效率从环十二酮和羟胺制备月桂内酰胺的方法。该方法包括以下步骤（a）至（e）：（a）在过量的环十二烷酮或溶剂存在下，使环十二酮与羟胺在水溶液中反应，生成环十二酮肟; （b）将在肟形成步骤后获得的反应混合物分离成油和水相，并收集油相的环十二酮肟溶液; （c）从在油/水相分离步骤中以油相收集的环十二酮肟溶液中除去溶解的水; （d）使用含芳环的化合物作为重排催化剂，通过重排反应从环十二酮肟生产月桂内酰胺; 和（e）在重排步骤之后将所生产的月桂内酰胺与反应混合物分离并纯化十二内酰胺。

3. 发明申请

US20130338364A1 IODOARENE DERIVATIVE, METHOD FOR MANUFACTURING OPTICALLY ACTIVE SPIROLACTONE COMPOUND BY USING THE SAME, AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CYCLOADDUCT 有权
标题翻译：异恶唑衍生物，使用它们制造光学活性螺旋体化合物的方法和制造光学活性环糊精的方法
公开(公告)号：US20130338364A1
公开(公告)日：2013-12-19
申请号：US14002574
申请日：2012-03-06
申请人： Kazuaki Ishihara , Muhammet Uyanik , Takeshi Yasui
发明人： Kazuaki Ishihara , Muhammet Uyanik , Takeshi Yasui
IPC分类号： B01J31/02 , C07D491/107 , C07D307/94
CPC分类号： B01J31/0209 , C07C217/20 , C07C233/69 , C07C233/70 , C07C235/48 , C07C271/16 , C07C311/17 , C07D307/94 , C07D317/72 , C07D491/107
摘要： An optically active spirolactone compound is highly enantioselectively produced by using an iodoarene derivative which can be synthesized easily and which is not racemized easily. A hypervalent iodine compound precursor (iodoarene derivative) which was able to be designed flexibly was synthesized from 2,6-dihydroxyiodoarene by using 1,2-aminoalcohol as a chiral source in short steps, a hypervalent iodine compound was prepared in a reaction system (in situ) by using a catalyst quantity of the resulting precursor in the presence of a stoichiometric quantity of m-CPBA, and a spirolactonization reaction of 3-(1-hydroxy-2-naphthyl)propionic acid was induced. As a result, a corresponding spirolactone compound was obtained at a high enantiomeric excess.
摘要翻译：通过使用可以容易地合成并且不容易外消旋化的碘代芳烃衍生物，高度对映选择性地制备光学活性的己内酯化合物。通过使用1,2-氨基醇作为手性来源，通过短时间步骤，可以从2,6-二羟基碘代芳烃合成出能够灵活设计的高价碘化合物前体（碘代芳烃衍生物），在反应体系中制备了高价碘化合物通过在化学计量的m-CPBA的存在下使用所得前体的催化剂量，并引发3-（1-羟基-2-萘基）丙酸的反式己内酯化反应。结果，以高对映体过量获得相应的己内酯化合物。

4. 发明授权

US07339082B2 Arylbis (perfluoroalkylsulfonyl)methane and metallic salt thereof, and methods for producing the same 失效
标题翻译：芳基（全氟烷基磺酰基）甲烷及其金属盐及其制备方法
公开(公告)号：US07339082B2
公开(公告)日：2008-03-04
申请号：US10996216
申请日：2004-11-22
申请人： Kazuaki Ishihara , Hisashi Yamamoto
发明人： Kazuaki Ishihara , Hisashi Yamamoto
IPC分类号： C07C315/04
CPC分类号： B01J31/0224 , B01J31/0244 , B01J31/122 , B01J2231/326 , B01J2231/40 , C07C45/69 , C07C67/08 , C07C317/10 , C07C47/445 , C07C69/78
摘要： The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmetric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfinic acid anhydride, and an arylbis (trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.
摘要翻译：本发明提供了高效率地生产具有庞大的芳基和电子接受芳基的各种类型的芳基双（全氟烷基磺酰基）甲烷的方法，其中通常被认为难以合成; 可广泛应用于不对称催化剂，各种功能材料等的新型芳基双（全氟烷基磺酰基）甲烷; 及其金属盐。此外，还提供优异的催化剂。将芳基卤代甲烷与三氟甲磺酸钠反应，由此得到的芳基甲基三氟甲基与t-BuLi等反应，得到的芳基甲基三氟甲基锂盐与三氟甲磺酸亚磺酸酐反应，并将芳基双（三氟甲磺酸）以高产率获得甲烷如五氟苯基双（三氟甲基）甲烷，{4-（五氟苯基）-2,3,5,6-四氟苯基}双（三氟甲基）甲烷等。

5. 发明授权

US07301045B2 Method for preparing ester condensate 失效
标题翻译：制备酯缩合物的方法
公开(公告)号：US07301045B2
公开(公告)日：2007-11-27
申请号：US10399233
申请日：2001-08-23
申请人： Kazuaki Ishihara , Hisashi Yamamoto
发明人： Kazuaki Ishihara , Hisashi Yamamoto
IPC分类号： C07C69/74 , C07C69/76 , C07C321/00
CPC分类号： B01J31/0212 , B01J27/135 , B01J31/2208 , B01J2231/40 , B01J2531/40 , C07C67/08 , C07C327/22 , C07D309/30 , C08G63/81 , C08G63/85 , C07C69/007 , C07C69/013 , C07C69/017 , C07C69/003 , C07C69/612 , C07C69/618 , C07C69/75 , C07C69/24 , C07C69/734 , C07C69/78
摘要： The present invention provides a method for preparing ester or thioester that can conduct catalytic esterification reaction with an equimolar amount of carboxylic acid and alcohol, or catalytic thioesterification reaction with carboxylic acid and an equimolar amount or small amount of thiol, and can be expected as an industrial method that needs an enormous amount of synthesis in the light of green chemistry. By using hafnium chloride (IV), especially tetravalent hafnium compounds represented by hafnium chloride (IV)·(THF)2 or hafnium (IV)t-butoxide as a (poly) condensation catalyst, direct condensation reaction is conducted from carboxylic acid and an equimolar amount of alcohol or a little smaller amount of thiol, in the nonpolar solvent such as toluene and the like, in a deoxidization atmosphere and under heating reflux, and the reaction synthesizes ester monomer or thioester monomer, polyester or polythioester. When heating reflux is conducted by using a nonpolar solvent, it is preferable to remove azeotropic water from the reaction system.
摘要翻译：本发明提供了一种制备可与等摩尔量的羧酸和醇进行催化酯化反应或与羧酸和等摩尔量或少量硫醇进行催化酯基酯化反应的酯或硫酯的方法，并且可以作为在绿色化学方面需要大量合成的工业方法。通过使用氯化铪（IV），特别是作为（多）缩合催化剂的氯化铪（IV）（THF）2 H 2或叔（叔丁醇）铪代表的四价铪化合物，直接缩合反应在脱氧气氛和加热回流下，在非极性溶剂如甲苯等中，从羧酸和等摩尔量的醇或少量的硫醇进行反应，合成酯单体或硫酯单体，聚酯或聚硫酯。当使用非极性溶剂进行加热回流时，优选从反应体系中除去共沸水。

6. 发明申请

US20130338371A1 METHOD FOR PRODUCING AROMATIC COMPOUND HAVING RING STRUCTURE THAT INCLUDES NITROGEN ATOM OR OXYGEN ATOM 有权
标题翻译：生产包含氮原子或氧原子的环状结构的芳族化合物的方法
公开(公告)号：US20130338371A1
公开(公告)日：2013-12-19
申请号：US13982424
申请日：2012-02-02
申请人： Kazuaki Ishihara , Uyanik Muhammet
发明人： Kazuaki Ishihara , Uyanik Muhammet
IPC分类号： C07D403/06 , C07D307/94 , C07D209/42 , C07D209/12
CPC分类号： C07D403/06 , C07D209/12 , C07D209/42 , C07D307/94
摘要： The invention is a method for efficiently producing an aromatic compound by an intramolecular cyclization reaction, the aromatic compound having a ring structure that includes a nitrogen atom or oxygen atom. An aromatic compound composed of tert-butyl-2-(3-oxo-3-phenylpropyl)phenyl carbamate or another aniline derivative or the like, or an aromatic compound composed of 3-(1-hydroxynaphthalene-2-yl)propionic acid or another naphthol derivative or the like is made to react in a system to which an oxidizing agent and a quaternary ammonium salt represented by general formula (1) are fed. In the formula, X is an iodine atom; and R1, R2, R3 and R4 are each independently a C1-30 hydrocarbon group in which some hydrogen atoms are optionally substituted with halogen atoms, or R1 and R2 may be combine to form a divalent organic group bonded to a nitrogen atom, and R3 and R4 may combine to form a divalent organic group bonded to a nitrogen atom.
摘要翻译：本发明是通过分子内环化反应有效制备芳族化合物的方法，所述芳族化合物具有包含氮原子或氧原子的环结构。由叔丁基-2-（3-氧代-3-苯基丙基）苯基氨基甲酸酯或其它苯胺衍生物等构成的芳族化合物或由3-（1-羟基萘-2-基）丙酸或使另一种萘酚衍生物等在通过通式（1）表示的氧化剂和季铵盐的系统中反应。在该式中，X是碘原子; 并且R 1，R 2，R 3和R 4各自独立地为C 1〜C 30烃基，其中一些氢原子任选被卤素原子取代，或者R 1和R 2可以结合形成与氮原子键合的二价有机基团，R 3 并且R 4可以结合形成键合到氮原子上的二价有机基团。

7. 发明申请

US20130217898A1 METHOD FOR MANUFACTURING ESTER 有权
标题翻译：制造方法
公开(公告)号：US20130217898A1
公开(公告)日：2013-08-22
申请号：US13881544
申请日：2011-10-11
申请人： Kazuaki Ishihara , Muhammet Uyanik
发明人： Kazuaki Ishihara , Muhammet Uyanik
IPC分类号： C07D313/04 , C07D307/83 , C07D307/935 , C07D307/33 , C07D309/30
CPC分类号： C07D313/04 , C07B33/00 , C07C37/56 , C07C67/42 , C07D307/33 , C07D307/77 , C07D307/79 , C07D307/83 , C07D307/88 , C07D307/935 , C07D309/30 , C07D323/04 , C07C69/24 , C07C39/28
摘要： The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ε-caprolactone was obtained at an isolated yield of 82%.
摘要翻译：本发明涉及通过使用过氧化氢的Baeyer-Villiger氧化反应从作为反应性底物的酮或醛制造酯的方法，在该方法中，作为催化剂M（BAr4）n，使用金属硼酸盐（M表示碱金属或碱土金属; Ar表示芳基; n表示与M的化合价相同的数）。例如，当使用环己酮作为反应性底物，并且使用Sr [B（3,5-CF 3 C 6 H 3）4] 2作为催化剂时，以82％的分离收率得到ε-己内酯。

8. 发明申请

US20120323014A1 METHOD FOR PRODUCING ALPHA-ACYLOXYCARBONYL COMPOUND AND NOVEL ALPHA-ACYLOXYCARBONYL COMPOUND 有权
标题翻译：用于生产α-羟基碳酰亚胺化合物的方法和新型α-丙烯酰氧基化合物
公开(公告)号：US20120323014A1
公开(公告)日：2012-12-20
申请号：US13581734
申请日：2011-03-04
申请人： Kazuaki Ishihara , Muhammet Uyanik
发明人： Kazuaki Ishihara , Muhammet Uyanik
IPC分类号： C07C67/42 , C07D233/90 , C07C69/533 , C07D309/30 , C07C69/602 , C07D213/78 , C07D333/38
CPC分类号： C07D213/50 , B01J31/0239 , B01J31/0268 , B01J2231/49 , B01J2231/70 , C07C67/00 , C07C205/57 , C07C2601/14 , C07C2602/08 , C07C2602/10 , C07D233/64 , C07D309/30 , C07D333/22 , C07C69/24 , C07C69/14 , C07C69/78 , C07C69/54 , C07C69/007
摘要： A method for producing an α-acyloxycarbonyl compound of the present invention includes performing an intermolecular reaction between a carboxylic acid and a carbonyl compound selected from the group consisting of ketones, aldehydes, and esters, which have a hydrogen atom at the α-position, using a hydroperoxide as an oxidizer and an iodide salt as a catalyst precursor, thereby introducing an acyloxy group derived from the carboxylic acid into the α-position of the carbonyl compound.
摘要翻译：本发明的α-酰氧基羰基化合物的制造方法包括在羧酸和选自由α-位上具有氢原子的酮，醛和酯组成的组中的羰基化合物进行分子间反应，使用氢过氧化物作为氧化剂和碘化物盐作为催化剂前体，由此将衍生自羧酸的酰氧基引入羰基化合物的α-位。

9. 发明授权

US07193113B2 Arylbis(perfluoroalkylsulfonyl) methane and metallic salt thereof, and methods for producing the same 失效
标题翻译：芳基（全氟烷基磺酰基）甲烷及其金属盐及其制备方法
公开(公告)号：US07193113B2
公开(公告)日：2007-03-20
申请号：US10450349
申请日：2001-12-14
申请人： Kazuaki Ishihara , Hisashi Yamamoto
发明人： Kazuaki Ishihara , Hisashi Yamamoto
IPC分类号： C07C317/14
CPC分类号： B01J31/0224 , B01J31/0244 , B01J31/122 , B01J2231/326 , B01J2231/40 , C07C45/69 , C07C67/08 , C07C317/10 , C07C47/445 , C07C69/78
摘要： The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis(trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.
摘要翻译：本发明提供了高效率地生产具有庞大的芳基和电子接受芳基的各种类型的芳基双（全氟烷基磺酰基）甲烷的方法，其中通常被认为难以合成; 可广泛应用于非均相催化剂，各种功能材料等的新型芳基双（全氟烷基磺酰基）甲烷; 及其金属盐。此外，还提供优异的催化剂。将芳基卤代甲烷与三氟甲磺酸钠反应，将由此产生的芳基甲基三氟甲基与t-BuLi等反应，将得到的芳基甲基三氟甲磺酸的锂盐与三氟甲磺酸酐反应，并将芳基双（三氟甲磺酸）以高产率获得甲烷如五氟苯基双（三氟甲基）甲烷，{4-（五氟苯基）-2,3,5,6-四氟苯基}双（三氟甲基）甲烷等。

10. 发明授权

US09018394B2 Method for producing aromatic compound having ring structure that includes nitrogen atom or oxygen atom 有权
标题翻译：含有氮原子或氧原子的具有环结构的芳香族化合物的制造方法
公开(公告)号：US09018394B2
公开(公告)日：2015-04-28
申请号：US13982424
申请日：2012-02-02
申请人： Kazuaki Ishihara , Uyanik Muhammet
发明人： Kazuaki Ishihara , Uyanik Muhammet
IPC分类号： C07D403/06 , C07D209/12 , C07D209/42 , C07D307/94
CPC分类号： C07D403/06 , C07D209/12 , C07D209/42 , C07D307/94
摘要： The invention is a method for efficiently producing an aromatic compound by an intramolecular cyclization reaction, the aromatic compound having a ring structure that includes a nitrogen atom or oxygen atom. An aromatic compound composed of tert-butyl-2-(3-oxo-3-phenylpropyl)phenyl carbamate or another aniline derivative or the like, or an aromatic compound composed of 3-(1-hydroxynaphthalene-2-yl)propionic acid or another naphthol derivative or the like is made to react in a system to which an oxidizing agent and a quaternary ammonium salt represented by general formula (1) are fed. In the formula, X is an iodine atom; and R1, R2, R3 and R4 are each independently a C1-30 hydrocarbon group in which some hydrogen atoms are optionally substituted with halogen atoms, or R1 and R2 may be combine to form a divalent organic group bonded to a nitrogen atom, and R3 and R4 may combine to form a divalent organic group bonded to a nitrogen atom.
摘要翻译：本发明是通过分子内环化反应有效制备芳族化合物的方法，所述芳族化合物具有包含氮原子或氧原子的环结构。由叔丁基-2-（3-氧代-3-苯基丙基）苯基氨基甲酸酯或其它苯胺衍生物等构成的芳族化合物或由3-（1-羟基萘-2-基）丙酸或使另一种萘酚衍生物等在通过通式（1）表示的氧化剂和季铵盐的系统中反应。在该式中，X是碘原子; 并且R 1，R 2，R 3和R 4各自独立地为C 1〜C 30烃基，其中一些氢原子任选被卤素原子取代，或者R 1和R 2可以结合形成与氮原子键合的二价有机基团，R 3 并且R 4可以结合形成键合到氮原子上的二价有机基团。

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