The Reactant Is A Cyclic Oxime Patents (Class 540/535)
  • Patent number: 11208380
    Abstract: The present invention relates to a process for purifying caprolactam from solutions of crude caprolactam by a direct treatment with one or more alkaline compounds of polyvalent metals, preferably bivalent and trivalent, without resorting to organic solvent extraction as used in the usual purification process. A further subject of the present invention is a facility devoid of a unit for organic solvent extraction and designed to carry out the caprolactam purification process described herein.
    Type: Grant
    Filed: August 21, 2020
    Date of Patent: December 28, 2021
    Assignee: AquafilSLO d.o.o.
    Inventors: Anacleto Dal Moro, Michele Cecchetto, Denis Jahic, Vid Margon
  • Patent number: 11140475
    Abstract: The present disclosure provides a sound absorbing material. The sound absorbing material comprising MFI-structural-type molecular sieves, the MFI-structural-type molecular sieves comprises frameworks and extra-framework cations, the framework comprising SiO2 and a metal oxide MxOy containing a metal element M, wherein a molar ratio of Si/M is between 220 and 600 in the framework, the metal element M comprises aluminum, and the extra-framework cations are at least one of hydrogen ions, alkali metal ions and alkaline earth metals. The present also provides a method for preparing a sound absorbing material and a speaker box using the sound absorbing material.
    Type: Grant
    Filed: July 26, 2019
    Date of Patent: October 5, 2021
    Assignee: AAC ACOUSTIC TECHNOLOGIES (SHENZHEN) CO., LTD.
    Inventors: Kun Tang, Hongshu Feng, Jiqiang Dai, Hezhi Wang
  • Publication number: 20150126732
    Abstract: Methods for producing lactams from oximes by performing a Beckmann rearrangement using a silicoaluminophosphate catalyst are provided. These catalysts may be used in gas phase or liquid phase reactions to convert oximes into lactams. High conversion of oxime and high selectivity for the desired lactams are produced using the disclosed methods, including high conversion and selectivity for ?-caprolactam produced from cyclohexanone oxime and high conversion and selectivity for ?-laurolactam produced from cyclododecanone oxime.
    Type: Application
    Filed: May 9, 2014
    Publication date: May 7, 2015
    Applicants: Honeywell International Inc., University of Southampton
    Inventors: Alan B. Levy, Robert Raja, Matthew E. Potter
  • Publication number: 20150119569
    Abstract: The present invention relates to a full-Si molecular sieve, wherein the full-Si molecular sieve has a Q4/Q3 of (10-90):1.
    Type: Application
    Filed: October 29, 2014
    Publication date: April 30, 2015
    Inventors: Xingtian SHU, Changjiu XIA, Min LIN, Bin ZHU, Xinxin PENG, Aiguo ZHENG, Mudi XIN, Yanjuan XIANG, Chunfeng SHI
  • Patent number: 8962826
    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.
    Type: Grant
    Filed: December 27, 2013
    Date of Patent: February 24, 2015
    Assignee: Ube Industries, Ltd.
    Inventors: Junichi Kugimoto, Joji Kawai, Kazuo Yamato, Masahide Okada, Tsunemi Sugimoto, Hiroshi Matsumoto
  • Patent number: 8865892
    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.
    Type: Grant
    Filed: December 21, 2011
    Date of Patent: October 21, 2014
    Assignee: China Petroleum Development Corporation, Taipei (Taiwan)
    Inventors: Tung-Han Tsai, Cheng-Fa Hsieh, Hung-Hung Hseuh, Chien-Chuan Shih
  • Patent number: 8779125
    Abstract: A redox ammoximation process in which a ketone or aldehyde is reacted with ammonia and oxygen in the presence of a catalyst; wherein the catalyst is an aluminophosphate based redox catalyst having at least two different redox catalytic sites comprising different transition metal atoms.
    Type: Grant
    Filed: May 8, 2013
    Date of Patent: July 15, 2014
    Assignee: University of Southampton
    Inventors: Robert Raja, John Meurig Thomas
  • Patent number: 8779124
    Abstract: A redox ammoximation process in which a ketone or aldehyde is reacted with ammonia and oxygen in the presence of a catalyst, wherein: the catalyst is an aluminophosphate based redox catalyst having the qualitative general formula (I) M1M2AlPO-5 (I) in which M1 is at least one transition metal atom having redox catalytic capability; M2 is at least one metal atom in the (IV) oxidation state; M1 and M2 are different from each other; and a proportion of the phosphorous atoms in the M1M2AlPO-5 type structure are replaced by M2 atoms.
    Type: Grant
    Filed: May 8, 2013
    Date of Patent: July 15, 2014
    Assignee: University of Southampton
    Inventors: Robert Raja, Alexander James Patterson
  • Patent number: 8772476
    Abstract: Methods for producing lactams from oximes by performing a Beckmann rearrangement using a silicoaluminophosphate catalyst are provided. These catalysts may be used in gas phase or liquid phase reactions to convert oximes into lactams. High conversion of oxime and high selectivity for the desired lactams are produced using the disclosed methods, including high conversion and selectivity for ?-caprolactam produced from cyclohexanone oxime and high conversion and selectivity for ?-laurolactam produced from cyclododecanone oxime.
    Type: Grant
    Filed: October 23, 2012
    Date of Patent: July 8, 2014
    Assignee: Honeywell International Inc.
    Inventors: Alan B. Levy, Robert Raja, Matthew E. Potter
  • Patent number: 8552180
    Abstract: The present invention provides a method for separating an amide from an amino acid ionic liquid. The method includes the step of providing a polar solvent and an extracting agent to the amino acid ionic liquid, so as to separate the amide from the amino acid ionic liquid. In the method of the present invention, there is no need to add ammonium for neutralization, such that no byproduct, ammonium sulfate, is formed. In addition, after the amide is separated from the amino acid ionic liquid, the amino acid ionic liquid can be recycled.
    Type: Grant
    Filed: December 14, 2009
    Date of Patent: October 8, 2013
    Assignee: China Petrochemical Development Corporation
    Inventors: Cheng-Fa Hsieh, Chien-Chuan Shih, Chi-Yuan Chen
  • Publication number: 20130109851
    Abstract: Methods for producing lactams from oximes by performing a Beckmann rearrangement using a silicoaluminophosphate catalyst are provided. These catalysts may be used in gas phase or liquid phase reactions to convert oximes into lactams. High conversion of oxime and high selectivity for the desired lactams are produced using the disclosed methods, including high conversion and selectivity for ?-caprolactam produced from cyclohexanone oxime and high conversion and selectivity for ?-laurolactam produced from cyclododecanone oxime.
    Type: Application
    Filed: October 23, 2012
    Publication date: May 2, 2013
    Applicants: Honeywell International Inc.
    Inventors: Honeywell International Inc., University of Southampton
  • Publication number: 20120184733
    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.
    Type: Application
    Filed: December 21, 2011
    Publication date: July 19, 2012
    Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)
    Inventors: Tung-Han Tsai, Cheng-Fa Hsieh, Hung-Hung Hseuh, Chien-Chuan Shih
  • Patent number: 8022201
    Abstract: The present invention is directed to a process for preparing amides. In particular, the process is directed to a process performable on the industrial scale, in which a ketoxime can be converted to a cyclic or acyclic amide by means of a Beckmann rearrangement using 2,4,6-trichloro-1,3,5-triazine as a catalyst in a nonpolar organic solvent.
    Type: Grant
    Filed: April 3, 2007
    Date of Patent: September 20, 2011
    Assignee: Evonik Degussa GmbH
    Inventors: Martin Roos, Stephanie Schauhoff, Martin Trageser, Hans-Peter Krimmer
  • Patent number: 8003825
    Abstract: The present invention provides a process for producing a cycloalkanone oxime by conducting a continuous ammoximation reaction in the presence of a titanosilicate catalyst with supplying a cycloalkanone, hydrogen peroxide, ammonia and an organic solvent into the reaction system, wherein the reaction temperature is from 90° C. to 120° C. and the supplying amount of the organic solvent is not more than 2 times by weight of that of the cycloalkanone.
    Type: Grant
    Filed: April 21, 2006
    Date of Patent: August 23, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Miyuki Oikawa
  • Publication number: 20110092699
    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.
    Type: Application
    Filed: June 10, 2009
    Publication date: April 21, 2011
    Inventors: Takahiro Iwahama, Tatsuya Nakano
  • Publication number: 20100179317
    Abstract: A redox ammoximation process in which a ketone or aldehyde is reacted with ammonia and oxygen in the presence of a catalyst; wherein the catalyst is an aluminophosphate based redox catalyst having at least two different redox catalytic sites comprising different transition metal atoms.
    Type: Application
    Filed: July 2, 2008
    Publication date: July 15, 2010
    Applicant: University of Southampton
    Inventor: Robert RAJA
  • Publication number: 20100029932
    Abstract: Disclosed is a process for producing an amide or lactam in a high yield in a simple manner by allowing a rearrangement reaction of an oxime compound to proceed without causing large amounts of by-products such as ammonium sulfate. Specifically, disclosed is a process for producing an amide or lactam in which a corresponding amide or lactam is produced by rearranging an oxime compound in the presence of a compound containing a structure represented by following Formula (1): —Z—X ??(1) wherein Z represents P, N, S, B, or Si atom; and X represents a leaving group, where Z is bonded to one or more atoms or groups besides X. In the process, X may be a halogen atom.
    Type: Application
    Filed: December 20, 2007
    Publication date: February 4, 2010
    Inventors: Yasutaka Ishii, Takahiro Iwahama, Tatsuya Nakano
  • Patent number: 7482446
    Abstract: Methods are disclosed of producing and purifying at least one amide. In accordance with one of the methods disclosed herein, the at least one amide is produced by providing an organic liquid comprising at least one oxime, providing at least one catalyst, adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises at least one amide, at least one impurity, and the at least one catalyst, and heating the rearrangement mass to a temperature of at least about 115° C. for a period of time in order to sulfonate, break down and/or reduce the concentration of some of the at least one impurity in the rearrangement mass.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: January 27, 2009
    Assignee: Honeywell International Inc.
    Inventors: Alan Levy, Gregory Cleotelis, II, James Sawyer, Nolan Henrich, III, Mohammed Loya, Matthew Warren, Gregory Moore
  • Patent number: 7449600
    Abstract: A process for producing cyclohexanone oxime is provided: (1) reacting cyclohexanone, hydrogen peroxide and ammonia in the presence of a titanosilicate catalyst to give a reaction solution containing cyclohexanone oxime, water, unreacted ammonia and unreacted cyclohexanone, (2) distilling off ammonia, (3) an extraction step, (4) mixing the organic layer obtained in step (3) with water followed by separating into an organic and aqueous layers, (5) distilling off organic solvent and water to obtain a bottom product containing cyclohexanone oxime and cyclohexanone, and (6) distilling off cyclohexanone and to obtain a bottom product containing cyclohexanone oxime; wherein a compound selected from an oxide, an oxo acid, an oxo acid salt, an oxo acid ester and an oxo acid amide of boron or phosphorous is added to at least one of the water used in the step (4) and the organic layer obtained in step (4) to be subjected to step (5).
    Type: Grant
    Filed: February 24, 2006
    Date of Patent: November 11, 2008
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Shinichi Kawase
  • Patent number: 7358357
    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 ?·V·D/?, wherein ?=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) ?=viscosity of th
    Type: Grant
    Filed: May 17, 2004
    Date of Patent: April 15, 2008
    Assignee: DSM IP Assets B.V.
    Inventors: Theodorus Maria T. M. Smeets, Joannes Albertus Wihelmus J. A. W. Lemmens, Frank F. Mostert, Peter Wei-Hae P. W-H. Cheng
  • Patent number: 7351820
    Abstract: The invention relates to a process for preparing caprolactam by Beckmann rearrangement of cyclohexanone oxime by feeding cyclohexanone oxime to a reaction mixture comprising (i) sulfuric acid (ii) SO3 and (iii) caprolactam , wherein the SO3 content of the reaction mixture is between 9 and 20 wt. % and the molar ratio M of the reaction mixture defined as (nso3+nH2SO4)/ncap is between 1 and 1.4, wherein nso3=quantity of SO3 in reaction mixture, in mol nso3=quantity of H2SO4 in reaction mixture, in mol ncap=quantity of caprolactam in reaction mixture, in mol.
    Type: Grant
    Filed: May 17, 2004
    Date of Patent: April 1, 2008
    Assignee: DSM IP Assets B.V.
    Inventors: Petrus Jozef Hubertus Thomissen, Joannes Albertus Wilhelmus Lemmens, Theodorus Maria Smeets
  • Patent number: 7339056
    Abstract: The invention relates to a continuous process for preparing caprolactam by Beckmann rearrangement of cyclohexanone oxime, said process comprising a) feeding (i) oleum and (ii) cyclohexanone oxime into a first reaction mixture comprising caprolactam, sulfuric acid and SO3, b) feeding (iii) a portion of the first reaction mixture and (iv) cyclohexanone oxime into a second reaction mixture comprising caprolactam, sulfuric acid and SO3, c) withdrawing a portion of the second reaction mixture, wherein the process further comprises obtaining the cyclohexanone oxime that is fed to the reaction mixtures by: 1) preparing an organic medium comprising cyclohexanone oxime dissolved in an organic solvent 2) separating, by distillation, cyclohexanone oxime from said organic medium.
    Type: Grant
    Filed: May 17, 2004
    Date of Patent: March 4, 2008
    Assignee: DSM IP Assets B.V.
    Inventors: Joannes Albertus Wilhelmus J. A. W. Lemmens, Frank F. Mostert, Theodorus Maria T. M. Smeets
  • Patent number: 7189845
    Abstract: The invention provides a method for producing ?-caprolactam comprising the steps of: a reaction process which subjects cyclohexanone oxime to a Beckmann rearrangement reaction in the presence of a solid catalyst; and a catalyst regeneration process which regenerates the solid catalyst used in the reaction process by heat treatment under an atmosphere comprising an oxygen-containing gas, wherein the solid catalyst heat-treated in the catalyst regeneration process is used in the reaction process, the carbon contents in the solid catalyst in the reaction process and the catalyst regeneration process are maintained in a range of 0.5 to 2% by weight, and the nitrogen contents in the solid catalyst in the reaction process and the catalyst regeneration process are maintained in a range of 0.01 to 0.2% by weight. According to the invention, ?-caprolactam can be produced in a high production yield for a long period of time by enhancing persistence of the catalytic activity for producing ?-caprolactam.
    Type: Grant
    Filed: March 25, 2005
    Date of Patent: March 13, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keisuke Sugita, Masaru Kitamura, Masahiro Hoshino
  • Patent number: 7090817
    Abstract: The invention relates to a process for the preparation of hydroxylammonium, said process comprising the steps of: a) feeding gaseous hydrogen to a reaction mixture, said reaction mixture comprising an aqueous reaction medium and a gaseous phase; b) catalytically reducing, in said reaction mixture, nitrate or nitrogen oxide with hydrogen to form the hydroxylammonium; c) withdrawing a gas mixture from the reaction mixture, said gas mixture comprising gaseous hydrogen and gaseous non-hydrogen compounds; d) separating at least part of the gaseous non-hydrogen compounds from the gas mixture to obtain a hydrogen-enriched gas; and e) passing the hydrogen-enriched gas to a hydrogenation zone.
    Type: Grant
    Filed: July 11, 2002
    Date of Patent: August 15, 2006
    Assignee: DSM IP Assets B.V.
    Inventors: Arno Herald Benneker, Johannes A. L. Brouwers, Godefridus M. Van Dortmont
  • Patent number: 7084269
    Abstract: It is an object of the present invention to provide an efficient method of continuously producing a lactam in high-temperature high-pressure water, and the present invention relates to a method of producing a lactam characterized by efficiently synthesizing the lactam while suppressing oxime hydrolysis by introducing an oxime as a reaction substrate and an acid into a reaction zone through which high-temperature high-pressure water is flowing, or introducing an oxime into flowing high-temperature high-pressure water containing an acid, thus raising the temperature of the reaction substrate to put the reaction substrate into a prescribed high-temperature high-pressure state within a short time and subjecting the reaction substrate to reaction; through the method, the lactam can be efficiently and continuously synthesized at a high rate from the oxime using an acid catalyst in water at a high temperature of at least 250° C. and a high pressure of at least 15 MPa.
    Type: Grant
    Filed: March 5, 2002
    Date of Patent: August 1, 2006
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Kiyotaka Hatakeda, Osamu Sato, Yutaka Ikushima, Kazuo Torii
  • Patent number: 7045622
    Abstract: It is an object of the present invention to provide a method of continuously producing a lactam in high-temperature high-pressure water, and the present invention relates to a method for producing a lactam characterized by selectively synthesizing the lactam without bringing about hydrolysis by introducing an oxime into flowing high-temperature high-pressure water, wherein the lactam is continuously synthesized at a high rate from the oxime in water at a high temperature of at least 250° C. and a high pressure of at least 12 MPa.
    Type: Grant
    Filed: March 23, 2001
    Date of Patent: May 16, 2006
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Kiyotaka Hatakeda, Osamu Sato, Yutaka Ikushima, Kazuo Torii
  • Patent number: 7022844
    Abstract: Methods are disclosed of producing and purifying at least one amide. In accordance with one of the methods disclosed herein, the at least one amide is produced by providing an organic liquid comprising at least one oxime, providing at least one catalyst, adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises at least one amide, at least one impurity, and the at least one catalyst, and heating the rearrangement mass to a temperature of at least about 115° C. for a period of time in order to sulfonate, break down and/or reduce the concentration of some of the at least one impurity in the rearrangement mass.
    Type: Grant
    Filed: September 21, 2002
    Date of Patent: April 4, 2006
    Assignee: Honeywell International Inc.
    Inventors: Alan Levy, Gregory Cleotelis, II, James Sawyer, Nolan Henrich, III, Mohammed Loya, Matthew Warren, Gregory Moore
  • Publication number: 20040176592
    Abstract: A method for producing cyclohexanone oxime, which comprises the steps of (1) subjecting to an amination reaction a starting material selected from the group consisting of cyclohexanol, cyclohexanone and a mixture thereof, thereby obtaining cyclohexylamine, and (2) subjecting the obtained cyclohexylamine to a partial oxidation reaction, thereby obtaining cyclohexanone oxime, wherein a by-product (&agr;) formed in the step (1) and/or a by-product (&bgr;) formed in the step (2) are/is recycled to a reaction system of the amination reaction in the step (1).
    Type: Application
    Filed: January 6, 2004
    Publication date: September 9, 2004
    Inventors: Ken Suzuki, Hajime Nagahara
  • Patent number: 6750336
    Abstract: A method for producing a lactam by using an organic solvent as a substrate solution, which makes it possible to introduce a high-concentration oxime into flowing high-temperature and high-pressure water, thereby allowing the high-concentration lactam to be synthesized with a high efficiency. With this method, the lactam is continuously synthesized at a high rate from the oxime under high-temperature and high-pressure water mixture conditions within a temperature range of no less than 250° C. and a pressure range of no less than 15 MPa.
    Type: Grant
    Filed: November 1, 2002
    Date of Patent: June 15, 2004
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Osamu Sato, Kiyotaka Hatakeda, Yutaka Ikushima, Kazuo Torii
  • Publication number: 20040097727
    Abstract: It is an object of the present invention to provide an efficient method of continuously producing a lactam in high-temperature high-pressure water, and the present invention relates to a method of producing a lactam characterized by efficiently synthesizing the lactam while suppressing oxime hydrolysis by introducing an oxime as a reaction substrate and an acid into a reaction zone through which high-temperature high-pressure water is flowing, or introducing an oxime into flowing high-temperature high-pressure water containing an acid, thus raising the temperature of the reaction substrate to put the reaction substrate into a prescribed high-temperature high-pressure state within a short time and subjecting the reaction substrate to reaction; through the method, the lactam can be efficiently and continuously synthesized at a high rate from the oxime using an acid catalyst in water at a high temperature of at least 250° C. and a high pressure of at least 15 MPa.
    Type: Application
    Filed: September 25, 2003
    Publication date: May 20, 2004
    Inventors: Kiyotaka Hatakeda, Osamu Sato, Yutaka Ikushima, Kazuo Torii
  • Patent number: 6713036
    Abstract: A novel process for continuously mixing and reacting at least two fluids are disclosed. Excellent mixing and superior pressure drop characteristics are achieved using cyclone mixing where at least two supply channels feed a mixing chamber to create a vortex of the fluids to be mixed. The alignment of the supply channels is such that fluids are introduced into the chamber at both tangential and radial directions. In the case of gas/liquid mixing, particularly advantageous is the injection of the liquid stream tangentially and the gas stream radially. Reaction of the fluids can take place within the mixing chamber or in a separate reactor in fluid communication with the mixing chamber outlet. The process is especially useful for reacting potentially explosive mixtures of reactants where a homogeneous reactor feed mixture is critical to maintaining a non-explosive environment.
    Type: Grant
    Filed: May 7, 2001
    Date of Patent: March 30, 2004
    Assignee: UOP LLC
    Inventors: Kurt M. Vanden Bussche, Suheil F. Abdo, Anil R. Oroskar
  • Publication number: 20040059108
    Abstract: Methods are disclosed of producing and purifying at least one amide. In accordance with one of the methods disclosed herein, the at least one amide is produced by providing an organic liquid comprising at least one oxime, providing at least one catalyst, adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises at least one amide, at least one impurity, and the at least one catalyst, and heating the rearrangement mass to a temperature of at least about 115° C. for a period of time in order to sulfonate, break down and/or reduce the concentration of some of the at least one impurity in the rearrangement mass.
    Type: Application
    Filed: September 21, 2002
    Publication date: March 25, 2004
    Inventors: Alan Levy, Gregory Cleotelis, James Sawyer, Nolan Henrich, Mohammed Loya, Matthew Warren, Gregory Moore
  • Patent number: 6489474
    Abstract: Object of the present invention is to provide a process for producing an amide compound with high efficiency by subjecting an oxime compound to Beckmann rearrangement in a liquid phase under mild reaction conditions. Namely, the invention relates to a process for producing an amide compound such as &egr;-caprolactam by subjecting an oxime compound such as cyclohexanone oxime to Beckmann rearrangement in a liquid phase, characterized in that the reaction is carried out in the presence of (1) a non-fluorine-containing sulfonic anhydride and an N,N-disubstituted amide compound or (2) at least one compound selected from the group consisting of sulfonic acids and anhydrides thereof, an N,N-disubstituted amide compound, and a carboxylic anhydride.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: December 3, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yuuji Kawaragi, Tohru Setoyama
  • Patent number: 6469163
    Abstract: An improvement in the conventional process for the production of caprolactam. The process involves: (a) reacting air with ammonia gas in an ammonia conversion zone to produce nitric oxide; (b) oxidizing a portion of the nitric oxide to nitrogen dioxide to produce an NOx-rich process gas stream; (c) reacting the NOx-rich stream with ammonium carbonate in a nitriting zone to produce ammonium nitrite; (d) reducing the ammonium nitrite to hydroxylamine diammonium sulfate; (e) hydrolyzing the hydroxylamine diammonium sulfate to hydroxylamine sulfate; (f) oximating the hydroxylamine sulfate with cyclohexanone to produce cyclohexanone oxime; and (g) converting the cyclohexanone oxime to caprolactam. The process is improved by adding supplemental oxygen downstream of the ammonia conversion zone to increase the quantity and rate of formation of nitrogen dioxide in the NOx-rich process gas stream.
    Type: Grant
    Filed: December 24, 1998
    Date of Patent: October 22, 2002
    Assignee: Praxair Technology Inc.
    Inventors: Diego Fernandez Echegaray, Antonio Augusto M. Velloso, Matthew Lincoln Wagner
  • Patent number: 6359128
    Abstract: Free-flowing flakes of vinyl caprolactam monomer usable below its melting point of 34° C. without developing coloration.
    Type: Grant
    Filed: July 18, 2000
    Date of Patent: March 19, 2002
    Assignee: ISP Investments Inc.
    Inventors: Arvind M. Mathur, James A. Dougherty, Philip F. Wolf
  • Patent number: 6333411
    Abstract: A method for production of caprolactam. The method involves: (a) reacting air with ammonia gas in an ammonia conversion zone to produce nitric oxide; (b) oxidizing at least a portion of the nitric oxide to nitrogen dioxide to produce an NOx-rich process gas stream; (c) reactively absorbing the NOx-rich gas stream with phosphoric acid containing solution in an absorption zone to form nitrate ions; (d) contacting the nitrate ions with air in a degassing zone to produce a nitrate-rich aqueous process stream; (e) reducing the nitrate-rich aqueous stream with hydrogen in the presence of phosphoric acid to produce hydroxylammonium phosphate; (f) oximating the hydroxylammonium phosphate with cyclohexanone to produce cyclohexanone oxime; and (g) converting the cyclohexanone oxime to caprolactam. According to the invention, supplemental oxygen is added downstream of the ammonia conversion zone to increase the quantity and rate of formation of nitrogen dioxide in the NOx-rich process gas stream.
    Type: Grant
    Filed: December 24, 1998
    Date of Patent: December 25, 2001
    Assignee: Praxair Technology, Inc.
    Inventors: Diego Fernandez Echegaray, Antonio Augusto M. Velloso, Matthew Lincoln Wagner
  • Patent number: 6252065
    Abstract: For the preparation of lactams comprising 6 to 12 carbon atoms from the corresponding cycloalkanone oximes by rearrangement according to the Beckmann reaction in the presence of acid, the process is characterized in that use is made of methanesulphonic acid.
    Type: Grant
    Filed: September 21, 1999
    Date of Patent: June 26, 2001
    Assignee: Elf Atochem, S.A.
    Inventor: Jean Ollivier
  • Patent number: 6245907
    Abstract: Disclosed is a process for producing a high purity caprolactam which comprises converting cyclohexene obtained by the partial hydrogenation of benzene into cyclohexanol through hydration, converting the cyclohexanol into cyclohexanone through dehydrogenation, converting the cyclohexanone into cyclohexanone oxime through oximation and converting the cyclohexanone oxime into caprolactam through the Beckman rearrangement, characterized by comprising isolating and purifying the methylcyclopentanol from the cyclohexanol prior to use of such cyclohexanol in dehydrogenation and feeding the isolated methylcyclopentanol directly to oximation in order that the methylcyclopentanol is not fed to dehydrogenation. The process of the invention advantageously provides an economic method for producing a caprolactam with greater purity.
    Type: Grant
    Filed: December 4, 1998
    Date of Patent: June 12, 2001
    Assignee: Hyosung Corporation
    Inventors: Myung Suk Suh, Seung Eon Park, Chang Hwang Lee, Myeong Hong Lee, Si Geun Lee, Jung Ho Kim
  • Patent number: 5900482
    Abstract: The present invention provides a method for producing .epsilon.-caprolactam, which comprises subjecting cyclohexene to a hydration reaction to obtain cyclohexanol, subjecting the cyclohexanol to a dehydrogenation reaction to obtain cyclohexanone, subjecting the cyclohexanone to an oxime-forming reaction to obtain cyclohexanone oxime, and subjecting the cyclohexanone oxime to a Beckmann rearrangement reaction to obtain .epsilon.-caprolactam, wherein methylcyclopentanones contained in the cyclohexanone subjected to the oxime-forming reaction are controlled to be not more than 400 ppm.According to the present invention, it is possible to produce .epsilon.-caprolactam having a quality not inferior to conventional quality at a low cost.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: May 4, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Kouji Teramoto, Yu Kanda, Makoto Tezuka, Toshio Uchibori, Hidefumi Sano
  • Patent number: 5594137
    Abstract: A process for the preparation of caprolactam by reacting cyclohexanone oxime with a cationic or nonionic surfactant and a cosurfactant in dilute sulfuric acid at a temperature in the range of 15.degree. C. to 40.degree. C., neutralizing excess acid present in the solution and recovering the caprolactam from the solution by filtration.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: January 14, 1997
    Assignee: Council of Scientific and Industrial Research
    Inventors: Brajesh K. Jha, Ajay S. Chhatre, Bhaskar D. Kulkarni, Subramanian Sivasanker
  • Patent number: 5502184
    Abstract: The invention provides a process for producing high quality .epsilon.-caprolactam which comprises allowing crude .epsilon.-caprolactam obtained by gas phase Beckmann rearrangement of cyclohexanone oxime to contact with hydrogen at 100.degree.-200.degree. C. in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: March 26, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Kajikuri, Hideto Tojima, Tomokazu Nakamura, Masaru Kitamura
  • Patent number: 5455346
    Abstract: Caprolactam is obtained from mixtures which contain polymers or thermoplastic molding materials having the repeating unit--N(H)--(CH.sub.2).sub.5 --C(O)--(a) by cleavage at elevated temperatures in the presence of a base under reduced pressure or (b) in the presence of water, by using a mixture essentially comprisingfrom 50 to 99.9% by weight of a polymer or of a thermoplastic molding material having the repeating unit--N(H)--(CH.sub.2).sub.5 --C(O)--from 0.1 to 50% by weight of additives selected from the group consisting of inorganic fillers, organic and inorganic pigments and dyes,from 0 to 10% by weight of organic and/or inorganic additives,from 0 to 40% by weight of non-polyamide-containing polymers andfrom 0 to 20% by weight of polyamides, with the exception of polycaprolactam and copolyamides prepared from caprolactam,and carrying out the cleavage in the presence of a base under reduced pressure, the water content of the mixture used being not more than 0.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: October 3, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Kopietz, Ulrich Kalck, Simon Jones, Peter Bassler, Claus-Ulrich Priester
  • Patent number: 5440032
    Abstract: Disclosed is a method for purifying a lactam-containing organic solution which comprises processing an organic solution containing at least one lactam with an anion exchange resin to remove an anionic surface active substance contained in said organic solution, and then extracting with water to separate an objective component contained in the organic solution to an aqueous solution.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: August 8, 1995
    Assignee: Ube Industries, Ltd.
    Inventors: Kazuhiko Hirosawa, Yasuhiro Kurokawa, Tomohiko Yamamoto, Masaru Matsunishi, Yoshihiro Nawata
  • Patent number: 5401843
    Abstract: A process for the preparation of caprolactam by reacting cyclohexanone oxime with an anionic surfactant and a cosurfactant in dilute sulfuric acid at a temperature in the range of 15.degree. C. to 40.degree. C., neutralising excess acid present in the solution and from the solution by filtration.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: March 28, 1995
    Assignee: Council of Scientific and Industrial Research
    Inventors: Brajesh K. Jha, Ajay S. Chhatre, Bhaskar D. Kulkarni, Subramanian Sivasanker
  • Patent number: 5362870
    Abstract: A process for producing a high purity caprolactam is disclosed in which a crude caprolactam obtained by a catalytic rearrangement of cyclohexanone oxime is subjected(1) to mixing, while stirring, with at least one hydrocarbon selected from the group consisting of aliphatic hydrocarbons and alicyclic hydrocarbons to form a liquid-liquid, two-layer liquid mixture, and then crystallizing caprolactam out of the liquid mixture;(2) to mixing with both at least one hydrocarbon selected from the group consisting of aliphatic hydrocarbons and alicyclic hydrocarbons, and water to form a liquid mixture, separating the liquid mixture into a hydrocarbon layer and a water layer, and then recovering caprolactam from the water layer; or(3) to distillation in the co-presence of at least one aliphatic saturated hydrocarbon of 10 to 18 carbon atoms.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: November 8, 1994
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Yasuhiko Higashio, Hiroshi Kajikuri, Keisuke Sugita, Hideki Doi, Masanobu Matsubara
  • Patent number: 5354859
    Abstract: .epsilon.-Caprolactam is prepared by bringing cyclohexanone oxime into contact in gas phase with solid catalysts such as a zeolite catalyst in the presence of at least one nitrogen-containing compound selected from the group consisting of ammonia, methylamines and .epsilon.-caprolactam.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: October 11, 1994
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Hiroshi Ichihashi, Masaru Kitamura, Hiroshi Kajikuri, Eiji Tasaka
  • Patent number: 5304643
    Abstract: .epsilon.-Caprolactam is prepared by subjecting cyclohexanone oxime in a gas phase to a catalytic reaction using zeolite catalysts in the presence of water and at least one compound selected from alcohols and ether compounds.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: April 19, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Kajikuri, Masaru Kitamura, Yasuhiko Higashio
  • Patent number: 5264571
    Abstract: A process for preparing caprolactam by Beckmann rearrangement of cyclohexanone oxime with oleum at from 85.degree. to 125.degree. C. in a plurality of rearrangement stages arranged in series entails returning a portion of the reaction mixture leaving the last rearrangement stage to at least one of the preceding rearrangement stages.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: November 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hugo Fuchs, Gerald Neubauer, Josef Ritz
  • Patent number: 5254684
    Abstract: A process for producing an amide which comprises subjecting an oxime to liquid phase rearrangement in the presence of phosphorus pentoxide and at least one compound selected from the group consisting of N,N-dialkyl amides, N-alkyl cyclic amides and dialkyl sulfoxides and optionally a fluorine-containing strong said or its derivative. Said process can rearrange an oxime to a corresponding amide in a good yield under mild reaction conditions in the presence of a less stoichiometric amount of a catalyst.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: October 19, 1993
    Assignees: Sumitomo Chemical Company, Limited, Yusuke Izumi
    Inventors: Yusuke Izumi, Hiroshi Sato, Hiroshi Yoshioka, Yoshisaburou Nomura
  • Patent number: 5227482
    Abstract: A method for preparing a lactam, which comprises subjecting a cycloalkanone oxime to a Beckmann rearrangement reaction in a gas phase in the presence of a carrier-supported catalyst containing tantalum, wherein the carrier-supported catalyst is the one prepared by contacting an organic compound containing tantalum to a silica carrier having pores with pore diameters of from to 150,000 .ANG. wherein the pore volume of pores with pore diameters of from 40 to 2,000 .ANG. is at least 80% of the total pore volume of pores with pore diameters of from 40 to 150,000 .ANG..
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: July 13, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventor: Takashi Ushikubo