公开(公告)号：US08962826B2

公开(公告)日：2015-02-24

申请号：US14141916

申请日：2013-12-27

Applicant: Ube Industries, Ltd.

Inventor： Junichi Kugimoto ,  Joji Kawai ,  Kazuo Yamato ,  Masahide Okada ,  Tsunemi Sugimoto ,  Hiroshi Matsumoto

IPC: C07D225/02 ,  C07D201/04 ,  C07D201/06

CPC classification number: C07D201/06 ,  C07D201/04 ,  C07D225/02

Abstract: A method for producing a high purity, high quality amide compound, particularly a lactam. An amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol% or less based on the ketone as a starting material. One or more of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A content of impurities having a cyclic bridge structure is controlled using a cycloalkanone purified by recrystallization.

Abstract translation: 一种生产高纯度，优质酰胺化合物，特别是内酰胺的方法。 以循环到肟形成步骤的溶液中所含的卤化物，醛化合物，醇化合物和腈化合物中的每一种的量基于作为起始原料的酮被控制为0.4摩尔％以下的量。 通过氢化和/或结晶来纯化酮，肟和酰胺化合物中的一种或多种，​​以消除含有双键的杂质。 使用通过重结晶纯化的环烷酮控制具有环状桥结构的杂质含量。

公开(公告)号：US08865892B2

公开(公告)日：2014-10-21

申请号：US13332834

申请日：2011-12-21

Applicant: Tung-Han Tsai ,  Cheng-Fa Hsieh ,  Hung-Hung Hseuh ,  Chien-Chuan Shih

Inventor： Tung-Han Tsai ,  Cheng-Fa Hsieh ,  Hung-Hung Hseuh ,  Chien-Chuan Shih

IPC: C07D201/04 ,  B01J31/02 ,  C07C231/10

CPC classification number: C07D201/04 ,  B01J31/0237 ,  B01J31/0244 ,  B01J2231/52 ,  C07C231/10 ,  Y02P20/584 ,  C07C233/07 ,  C07C233/05

Abstract: The present invention provides a method for preparing an amide. The method includes the steps of performing in a reactor including a catalyst composition having a nitrogen-containing heterocyclic compound and sulfuric acid Beckman rearrangement of a ketoxime to form a product stream having the amide, wherein a molar ratio of the nitrogen-containing heterocyclic compound to the sulfuric acid is from 1:1 to 1:8; and separating an organic phase having the amide and an aqueous phase having the catalyst composition from the product stream. The present invention facilitates the regeneration of the catalyst composition with low water content, so as to increase the conversion rate of a ketoxime and the selectivity of an amide.

Abstract translation: 本发明提供一种制备酰胺的方法。 该方法包括以下步骤：在包括具有含氮杂环化合物的催化剂组合物和酮肟的硫酸贝克曼重排反应器的反应器中进行，以形成具有酰胺的产物流，其中含氮杂环化合物与 硫酸为1:1至1:8; 并从产物流中分离出具有酰胺的有机相和具有催化剂组成的水相。 本发明有助于低水含量的催化剂组合物的再生，从而提高酮肟的转化率和酰胺的选择性。

公开(公告)号：US08163899B2

公开(公告)日：2012-04-24

申请号：US12526494

申请日：2008-02-08

Applicant: Kazuaki Ishihara ,  Junichi Kugimoto ,  Joji Kawai

Inventor： Kazuaki Ishihara ,  Junichi Kugimoto ,  Joji Kawai

IPC: C07D201/04

CPC classification number: C07D201/04 ,  C07D225/02 ,  Y02P20/582

Abstract: 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.

Abstract translation: 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。

公开(公告)号：US20110092699A1

公开(公告)日：2011-04-21

申请号：US12997287

申请日：2009-06-10

Applicant: Takahiro Iwahama ,  Tatsuya Nakano

Inventor： Takahiro Iwahama ,  Tatsuya Nakano

IPC: C07D201/04

CPC classification number: C07D201/04 ,  C07D223/10 ,  Y02P20/52

Abstract: 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-LA (1) wherein G represents P, N, S, B or Si atom; and LA represents a leaving group, wherein G is bound to one or more atoms or groups in addition to LA; 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.

Abstract translation: 一种方法是通过使肟化合物在溶剂中进行重排来生成酰胺或内酰胺：在至少一种选自包含与构成芳香族的碳原子结合的离去基团的芳族化合物（A1）的催化剂的存在下， 芳环包括作为其组成原子的杂原子或其包含作为其组成原子的与吸电子基团结合的碳原子，和包含式（1）结构的化合物（A2）： -G-LA（1）其中G表示P，N，S，B或Si原子; 并且LA表示离去基团，其中除了LA之外，G与一个或多个原子或基团结合; 和包含含卤素的有机酸的助催化剂，得到相应的酰胺或内酰胺，其中当单独使用芳族化合物（A1）作为催化剂时，溶剂是通常选自烃溶剂的至少一种溶剂。 生产过程可以简单地以高产率产生酰胺或内酰胺，而不会引起大量副产物如硫酸铵。

公开(公告)号：US20100063274A1

公开(公告)日：2010-03-11

申请号：US12501699

申请日：2009-07-13

Applicant: Tung-Han Tsai ,  Pin-To Yao ,  Cheng-Fa Hsieh

Inventor： Tung-Han Tsai ,  Pin-To Yao ,  Cheng-Fa Hsieh

IPC: C07D201/04 ,  C07D223/10

CPC classification number: C07D201/04 ,  C07D223/10

Abstract: The present invention provides a method for preparing amides, in which an amino acid ionic liquid is used as both a reaction medium and a catalyst to catalyze Beckman rearrangement of a ketoxime, so as to produce an amide. In the method, the rearrangement is conducted by catalyzing a ketoxime with an amino acid ionic liquid having the asymmetric property at a moderate reaction temperature during a short reaction time, so as to produce an amide without adding other catalysts such as concentrate sulfuric acid. The method has advantages such as avoiding corrosion in equipments with pipelines, the high conversion rate of ketoximes and the high selectivity of amides.

Abstract translation: 本发明提供了一种制备酰胺的方法，其中使用氨基酸离子液体作为反应介质和催化贝克曼重排酮肟的催化剂，以产生酰胺。 在该方法中，通过在短的反应时间内在适度的反应温度下用具有不对称性质的氨基酸离子液体催化酮肟进行重排，从而在不加入其它催化剂如浓硫酸的情况下生成酰胺。 该方法具有避免管道设备腐蚀，酮肟转化率高，酰胺选择性高等优点。

公开(公告)号：US20050197499A1

公开(公告)日：2005-09-08

申请号：US10795726

申请日：2004-03-08

Applicant: Zhiping Shan ,  Chuen Yeh ,  Philip Angevine ,  Frits Dautzenberg ,  Jacobus Jansen

Inventor： Zhiping Shan ,  Chuen Yeh ,  Philip Angevine ,  Frits Dautzenberg ,  Jacobus Jansen

IPC: C07D301/12 ,  C07D201/04

CPC classification number: C07D301/19 ,  Y02P20/125

Abstract: An integrated process combines olefin epoxidation with production of cyclohexanone and cyclohexanol for nylon. Cyclohexanone and cyclohexanol normally produced by the oxidation of cyclohexane, in which cyclohexyl hydroperoxide is generated and is removed or decomposed down stream. However, this invention utilizes the intermediate of cyclohexyl hydroperoxide as an oxidant for the olefin epoxidation and meanwhile generates a valuable product.

Abstract translation: 一体化方法将烯烃环氧化与生产环己酮和环己醇用于尼龙。 通常通过环己烷氧化生成环己酮和环己醇，其中产生环己基氢过氧化物并在流下被除去或分解。 然而，本发明利用环己基氢过氧化物的中间体作为烯烃环氧化的氧化剂，同时产生有价值的产物。

公开(公告)号：US5914398A

公开(公告)日：1999-06-22

申请号：US888235

申请日：1997-07-03

Applicant: Angela Carati ,  Carlo Perego ,  Leonardo Dalloro ,  Giordano De Alberti ,  Stefano Palmery

Inventor： Angela Carati ,  Carlo Perego ,  Leonardo Dalloro ,  Giordano De Alberti ,  Stefano Palmery

IPC: B01J21/12 ,  B01J35/10 ,  C07B61/00 ,  C07C231/10 ,  C07C233/00 ,  C07D201/04

CPC classification number: B01J21/12 ,  B01J35/10 ,  C07D201/04 ,  B01J35/1023 ,  B01J35/1028 ,  B01J35/1042 ,  B01J35/1047 ,  B01J35/1061 ,  Y02P20/52

Abstract: Process for the preparation of caprolactam by the catalytic rearrangement of cyclohexanone oxime in which a vapour phase oxime is contacting a catalyst selected from an essentially amorphous, micro-mesoporous silica-alumina having a molar ratio SiO.sub.2 /Al.sub.2 O.sub.3 of 30 to 5000, a surface area of at least 500 m.sup.2 /g and a total pore volume of 0.3 to 1.3 ml/g.

Abstract translation: 通过环己酮肟的催化重排制备己内酰胺的方法，其中气相肟与选自摩尔比SiO 2 / Al 2 O 3的基本上无定形的微介孔二氧化硅 - 氧化铝的催化剂接触，催化剂肟的表面积 至少为500m 2 / g，总孔体积为0.3〜1.3ml / g。

公开(公告)号：US5599987A

公开(公告)日：1997-02-04

申请号：US414677

申请日：1995-03-31

Applicant: Guy L. Crocco ,  John C. Jubin, Jr. ,  John G. Zajacek

Inventor： Guy L. Crocco ,  John C. Jubin, Jr. ,  John G. Zajacek

IPC: C07C249/04 ,  C07D201/02 ,  C07D201/04 ,  C07D201/06

CPC classification number: C07C249/04 ,  Y02P20/125

Abstract: An integrated process for producing cyclohexanone oxime, a caprolactam precursor, is provided wherein isopropanol is utilized to generate the hydrogen peroxide oxidizing agent. The acetone produced as a co-product is recycled back to the secondary alcohol by hydrogenation. Ammoximation of cyclohexanone is performed in the presence of water and an alcohol other than isopropanol such as methanol or t-butyl alcohol.

Abstract translation: 提供了一种用于生产环己酮肟，己内酰胺前体的综合方法，其中使用异丙醇生成过氧化氢氧化剂。 作为副产物生产的丙酮通过氢化再循环回到仲醇中。 在水和除异丙醇之外的醇（如甲醇或叔丁醇）的存在下进行环己酮的接近。

公开(公告)号：US5451701A

公开(公告)日：1995-09-19

申请号：US266820

申请日：1994-06-27

Applicant: John G. Zajacek ,  John C. Jubin ,  Guy L. Crocco

Inventor： John G. Zajacek ,  John C. Jubin ,  Guy L. Crocco

IPC: C07C249/04 ,  C07C251/44 ,  C07D201/02 ,  C07D201/04 ,  C07D201/06

CPC classification number: C07C249/04 ,  C07C251/44 ,  Y02P20/125

Abstract: An integrated process for producing cyclohexanone oxime, a caprolactam precursor, is provided wherein a secondary alcohol is utilized to generate the hydrogen peroxide oxidizing agent and as a reaction medium for ammoximation. The ketone produced as a co-product is recycled back to the secondary alcohol by hydrogenation.

Abstract translation: 提供了一种用于生产环己酮肟，己内酰胺前体的综合方法，其中使用仲醇产生过氧化氢氧化剂和作为氨肟化反应的反应介质。 作为副产物生产的酮通过氢化再循环回到仲醇中。

公开(公告)号：US5312915A

公开(公告)日：1994-05-17

申请号：US118721

申请日：1993-09-10

Applicant: Tatsuaki Yashima ,  Takayuki Komatsu

Inventor： Tatsuaki Yashima ,  Takayuki Komatsu

IPC: B01J29/06 ,  C07B61/00 ,  C07D201/04 ,  E07D201/04

CPC classification number: C07D201/04 ,  Y02P20/52

Abstract: .epsilon.-Caprolactam is produced efficiently with high selectivity by contacting cyclohexanone oxime in gas phase with a solid catalyst which is a crystalline zeolite having a pore size smaller than molecular size of cyclohexanone oxime or a crystalline zeolite having closed pores.

Abstract translation: 通过使气相中的环己酮肟与具有小于环己酮肟的分子尺寸的孔结构的结晶沸石的固体催化剂或具有闭孔的结晶沸石接触，高效选择性地制备ε-己内酰胺。