公开(公告)号：US20150353478A1

公开(公告)日：2015-12-10

申请号：US14655514

申请日：2013-12-12

Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED

Inventor： Masahiro HOSHINO ,  Yuta KIKUCHI ,  Sho TSUJIUCHI

IPC: C07C249/04 ,  C07D201/04

CPC classification number: C07C249/04 ,  C07C2601/14 ,  C07D201/04 ,  C07C251/44

Abstract: Provided is a method for producing an oxime compound with satisfactory selectivity. Provide is a method for producing an oxime represented by the following formula (II): wherein R1 and R2 are respectively the same as defined below, the method including oxidizing an amine represented by the following formula (I): wherein R1 and R2 each independently represents a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group (provided that R1 and R2 are not simultaneously hydrogen atoms), orR1 and R2, together with the carbon atom to which R1 and R2 are attached, form an optionally substituted alicyclic hydrocarbon group having 3 to 12 carbon atoms [hereinafter sometimes referred to as the amine compound (I)],with oxygen in the presence of a layered silicate.

Abstract translation: 提供一种具有令人满意的选择性的肟化合物的制造方法。 提供一种生产由下式（II）表示的肟的方法：其中R1和R2分别与下述定义相同，该方法包括氧化由下式（I）表示的胺：其中R1和R2各自独立地 表示氢原子，任选取代的烃基或任选取代的杂环基（条件是R 1和R 2不同时为氢原子），或者R 1和R 2与连接R 1和R 2的碳原子一起形成 任选取代的具有3〜12个碳原子的脂环族烃基[以下有时称为胺化合物（I）]与层状硅酸盐存在下的氧。

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：US20140114062A1

公开(公告)日：2014-04-24

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: C07D201/06 ,  C07D225/02

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：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：US20110313149A1

公开(公告)日：2011-12-22

申请号：US13254217

申请日：2010-03-04

Applicant: Junichi Kugimoto ,  Tsunemi Sugimoto

Inventor： Junichi Kugimoto ,  Tsunemi Sugimoto

IPC: C07D225/02

CPC classification number: C07D225/02 ,  C07D201/04

Abstract: This invention relates to a process for producing an amide compound by Beckmann rearrangement of an oxime compound using a compound having at least two electron-withdrawing leaving groups as a rearrangement catalyst, the process comprising a pre-preparation step in which the rearrangement catalyst and at least a part of the oxime compound are mixed and reacted; and a rearrangement reaction step in which the oxime compound is rearranged at a temperature higher than that in the pre-preparation step.

Abstract translation: 本发明涉及通过使用具有至少两个吸电子离去基团的化合物作为重排催化剂的肟化合物的贝克曼重排制备酰胺化合物的方法，该方法包括预制备步骤，其中重排催化剂和 将至少一部分肟化合物混合并反应; 和重排反应步骤，其中肟化合物在比预制备步骤中高的温度下重新排列。

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：US20110065913A1

公开(公告)日：2011-03-17

申请号：US12993451

申请日：2009-05-19

Applicant: Junichi Kugimoto ,  Nobuhiro Ii ,  Takashi Doi ,  Satoru Fujitsu ,  Tadashi Gotou ,  Hideo Shimomura ,  Ryouta Yasumatsu ,  Joji Kawai

Inventor： Junichi Kugimoto ,  Nobuhiro Ii ,  Takashi Doi ,  Satoru Fujitsu ,  Tadashi Gotou ,  Hideo Shimomura ,  Ryouta Yasumatsu ,  Joji Kawai

IPC: C07D225/02

CPC classification number: C07D201/04 ,  C07D225/02

Abstract: The present invention relates to a process for producing laurolactam from cyclododecanone oxime by liquid-phase rearrangement reaction using trichlorotriazine as a rearrangement catalyst. The present invention can provide a process which can solve the problem of termination of the reaction at a certain conversion, can prevent an inactive precipitate generated from trichlorotriazine from precipitating in the course of the reaction process, and can remove an inactive precipitate, an active intermediate and a residual catalyst.

Abstract translation: 本发明涉及使用三氯三嗪作为重排催化剂通过液相重排反应从环十二酮肟生产十二内酰胺的方法。 本发明可以提供能够解决在一定转化时终止反应的问题的方法，可以防止三氯三嗪在反应过程中产生的不活泼的沉淀物沉淀，并且可以除去无活性的沉淀物，活性中间体 和残留催化剂。

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：US07358357B2

公开(公告)日：2008-04-15

申请号：US10557770

申请日：2004-05-17

Applicant: Theodorus Maria T. M. Smeets ,  Joannes Albertus Wihelmus J. A. W. Lemmens ,  Frank F. Mostert ,  Peter Wei-Hae P. W-H. Cheng

Inventor： Theodorus Maria T. M. Smeets ,  Joannes Albertus Wihelmus J. A. W. Lemmens ,  Frank F. Mostert ,  Peter Wei-Hae P. W-H. Cheng

IPC: C07D223/10

CPC classification number: B01F5/0428 ,  B01F5/0415 ,  B01J19/26 ,  B01J2219/00164 ,  C07D201/04

Abstract: The invention relates to a process for preparing caprolactam by admixture of cyclohexanone oxime to a reaction mixture comprising caprolactam and sulfuric acid using a mixing device, said mixing device comprising (i) a tube through which the reaction mixture can flow, and (ii) channels disposed around the tube, said channels opening into the tube, said process comprising: passing the reaction mixture through the tube, and feeding the cyclohexanone oxime into the reaction mixture through one or more of said channels, wherein Re>5000, Re being the Reynolds number as defined by ρ·V·D/η, wherein ρ=density (in kg/m3) of the reaction mixture that is fed to the tube V=velocity of the reaction mixture, V being defined as W/A, wherein W is the flow rate (in m3/s) of the reaction mixture that is fed into the tube and A is the cross section area of the tube (in m2) at the level where said channels open into the tube D=diameter of the tube at the level where said channels open into the tube (in m) η=viscosity of the reaction mixture that is fed into the tube (in Pa·s).

Abstract translation: 本发明涉及通过使用混合装置将环己酮肟与包含己内酰胺和硫酸的反应混合物混合来制备己内酰胺的方法，所述混合装置包括（i）反应混合物可以流过的管，以及（ii）通道 所述方法包括：使反应混合物通过管，并通过一个或多个所述通道将环己酮肟进料到反应混合物中，其中Re> 5000，Re为雷诺数 其数值由rho.VD / eta定义，其中rho =加入到管中的反应混合物的密度（单位为kg / m 3）V =反应混合物的速度，V定义为 W / A，其中W是供给到管中的反应混合物的流速（以m 3 S / s），A为管的横截面积（m / 2）在所述通道打开到管中的水平面D =在其上的管的直径 所述通道通入管中（以m计）eta =进料到管中的反应混合物的粘度（Pa.s）。