Cyclization To Form The Hetero Ring Patents (Class 540/538)
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Patent number: 12134711Abstract: The present disclosure provides a PVC or CPVC solvent cement and a composition for forming a PVC or CPVC coating on an object. The solvent cement and the coating composition each include one or more caprolactam-derived solvents and a polymer selected from the group of polyvinyl chloride and chlorinated polyvinyl chloride. The one or more caprolactam-derived solvents include a linear alkyl group of 1, 2 or 4 unsubstituted carbons or an alkoxymethyl group of 2 or 3 unsubstituted carbons bonded to a nitrogen heteroatom.Type: GrantFiled: December 9, 2019Date of Patent: November 5, 2024Assignee: AdvanSix Resins & Chemicals LLCInventors: Jaime A. Flores-Vasquez, Edward Asirvatham, Karttikay Moudgil
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Patent number: 11753372Abstract: A new process for the production of epsilon caprolactam (CPL) from 6-aminocaproic acid (6-ACA) can be obtained either from traditional petro chemical processes or can be obtained from biochemical processes. With the proposed process, the reaction time for conversion of 6-aminocaproic acid to the Nylon 6 monomer is shorter and significant energy savings are possible which is advantageous for industrial scale production. The conversion of 6-aminocaproic acid to the Nylon 6 monomer runs at atmospheric pressure and in the final product epsilon caprolactam with no oligomers formation of significance is obtained.Type: GrantFiled: December 23, 2019Date of Patent: September 12, 2023Assignees: AQUAFIL S.P.A., GENOMATICA INC.Inventors: Michele Cecchetto, Anacleto Dal Moro, Lauri Hannunpoika Suominen, Michael Japs
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Patent number: 8946411Abstract: Processes are disclosed for the conversion of adipic acid to caprolactam employing a chemocatalytic reaction in which an adipic acid substrate is reacted with ammonia and hydrogen, in the presence of particular heterogeneous catalysts and employing unique solvents. The present invention also enables the conversion of other adipic acid substrates, such as mono-esters of adipic acid, di-esters of adipic acid, mono-amides of adipic acid, di-amides of adipic acid, and salts thereof to caprolactam. Solvents useful in the process that do not react with ammonia are also disclosed. Catalyst supports are disclosed which catalyze the reaction of the substrate with ammonia in the absence of added metal. Metals on the catalyst supports comprise ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), and/or platinum (Pt). Heterogeneous catalysts comprising ruthenium (Ru) and rhenium (Re) on titania and/or zirconia supports are also disclosed.Type: GrantFiled: February 13, 2013Date of Patent: February 3, 2015Assignee: Rennovia, Inc.Inventors: Eric L. Dias, Vincent J. Murphy, James Longmire, Hong Jiang
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Publication number: 20140134681Abstract: The invention relates to a method for preparing 6-aminocaproic acid (hereinafter also referred to as ‘6-ACA’) using a biocatalyst. The invention further relates to a method for preparing e-caprolactam (hereafter referred to as ‘caprolactam’) by cyclising such 6-ACA. The invention further relates to a host cell, a micro-organism, or a polynucleotide which may be used in the preparation of 6-ACA or caprolactam.Type: ApplicationFiled: December 13, 2013Publication date: May 15, 2014Inventors: Petronella Catharina RAEMAKERS-FRANKEN, Martin SCHURMANN, Axel Christoph TREFZER, Stefaan Marie Andre DE WILDEMAN
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Publication number: 20140056803Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to nitrogen based hydrocarbon compounds such as pyridines. The method includes the reaction of acetylene with ammonia and controlling the ratio of acetylene to ammonia to generate the desired nitrogen based hydrocarbon compound.Type: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin, Debarshi Majumder
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Publication number: 20130237698Abstract: The invention is directed to a method for preparing 6-aminocaproic acid, comprising decarboxylating alpha-aminopimelic acid, using at least one biocatalyst comprising an enzyme having alpha-aminopimelic acid decarboxylase activity. The invention is further directed to a method for preparing caprolactam from 6-aminocaproic acid prepared by said method, to a host cell suitable for use in a method according to the invention and to a polynucleotide encoding a decarboxylase that may be used in a method according to the invention.Type: ApplicationFiled: August 26, 2011Publication date: September 12, 2013Applicant: DSM IP ASSETS B.V.Inventors: Stefanus Cornelis Hendrikus Turk, Martin Schürmann, Axel Christoph Trefzer, Petronella Catharina Raemakers-Franken, Hildegard Henna Menke
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Publication number: 20130225785Abstract: Processes are disclosed for the conversion of adipic acid to caprolactam employing a chemocatalytic reaction in which an adipic acid substrate is reacted with ammonia and hydrogen, in the presence of particular heterogeneous catalysts and employing unique solvents. The present invention also enables the conversion of other adipic acid substrates, such as mono-esters of adipic acid, di-esters of adipic acid, mono-amides of adipic acid, di-amides of adipic acid, and salts thereof to caprolactam. Solvents useful in the process that do not react with ammonia are also disclosed. Catalyst supports are disclosed which catalyze the reaction of the substrate with ammonia in the absence of added metal. Metals on the catalyst supports comprise ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), and/or platinum (Pt). Heterogeneous catalysts comprising ruthenium (Ru) and rhenium (Re) on titania and/or zirconia supports are also disclosed.Type: ApplicationFiled: February 13, 2013Publication date: August 29, 2013Applicant: Rennovia, Inc.Inventor: Rennovia, Inc.
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Publication number: 20130131306Abstract: Processes for producing caprolactam (CL) and derivatives thereof from adipic acid (AA) obtained from fermentation broths containing diammonium adipate (DAA) or monoammonium adipate (MAA).Type: ApplicationFiled: June 10, 2011Publication date: May 23, 2013Applicant: BIOAMBER S.A.S.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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Publication number: 20130116398Abstract: Processes for making caprolactam (CL) from monoammonium adipate (MAA) and/or adipic aicd (AA) obtained from a clarified diammonium adipate-containing (DAA-containing) fermentation broth or MAA-containing fermentation broth and converting the MAA or AA to the CL with hydrogen in the presence of a catalyst at selected temperatures and pressures.Type: ApplicationFiled: June 10, 2011Publication date: May 9, 2013Applicant: BIOAMBER S.A.S.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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Publication number: 20130085255Abstract: Provided herein are processes for preparing caprolactam from a starting material such as one or more of the cis,cis-, cis,trans- and trans,trans-double-bond isomers of muconamide, muconic acid ester, or muconic acid. The starting material, intermediates, and caprolactam prepared therefrom can contain carbon atoms derived from biomass containing detectable 14C content determined according to ASTM D6866 and optionally containing a 14C content up to 0.0000000001% (one part per trillion). Caprolactam so prepared can be used to make various polyamides.Type: ApplicationFiled: April 9, 2012Publication date: April 4, 2013Applicant: Amyris, Inc.Inventors: Laetitia Coudray, Vu Bui, John W. Frost, Dirk Schweitzer
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Publication number: 20130030146Abstract: The invention relates to a method for preparing caprolactam comprising recovering a mixture containing 6-aminocaproic acid, from a culture medium comprising biomass, and thereafter cyclising the 6-aminocaproic acid in the presence of superheated steam, thereby forming caprolactam, wherein the weight to weight ratio carbohydrate to 6-aminocaproic acid in said mixture is 0.03 or less.Type: ApplicationFiled: December 22, 2010Publication date: January 31, 2013Applicant: DSM IP ASSETS B.V.Inventors: Rudolf Philippus Maria Guit, Thomas Van Der Does, Lourina Madeleine Raamsdonk
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Publication number: 20120264908Abstract: The present invention generally relates to processes for the conversion of glucose to caprolactam employing chemocatalytic oxidation and reduction reactions. The present invention also includes processes for the conversion of glucose to caprolactam via amido polyhydroxy acid products and amidocaproic acid or derivatives thereof. The present invention also includes processes that catalytically oxidize an amidopolyol to amidopolyhydroxy acid or derivatives thereof, and processes that catalytically hydrodeoxygenate amino or amido polyhydroxy acid or derivatives thereof to an amino or amidocaproic acid product. The amino or amidocaproic acid product may then be converted to caprolactam. The present invention also includes products produced by such processes and products producable from such products.Type: ApplicationFiled: March 29, 2012Publication date: October 18, 2012Applicant: Rennovia, Inc.Inventors: Vincent J. MURPHY, Eric L. DIAS, James A. W. SHOEMAKER, Thomas R. BOUSSIE, Zachary M. FRESCO
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Patent number: 8283466Abstract: Catalytic processes for preparing caprolactam, pipecolinic acid, and their derivatives, from lysine or alpha-amino-epsilon-caprolactam starting materials, and products produced thereby. A process for preparing caprolactam or a derivative thereof, the process comprising contacting a reactant comprising lysine or alpha aminocaprolactam with a catalyst and a gas comprising hydrogen gas, in the presence of a solvent. The catalyst may be provided on a support material, such as a transition metal.Type: GrantFiled: February 20, 2008Date of Patent: October 9, 2012Assignee: Board of Trustees of Michigan State UniversityInventor: John W. Frost
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Patent number: 8231765Abstract: A method and a plant are disclosed for purifying lactams, particularly lactams obtained by cyclizing hydrolysis of aminonitrile. The purification of ?-caprolactam obtained by cyclizing hydrolysis of aminocapronitrile is described which includes eliminating the ammonia from the reaction medium of the hydrolysis, then recovering the lactam from the medium in purified form. The recovery is carried out by performing at least a distillation of the lactam in the presence of a base producing optionally a fronts fraction having compounds more volatile than the lactam, a fraction having the lactam to be recovered to the degree of desired purity and a distillation tails having the lactam and compounds less volatile than the lactam. The distillation tails are treated by various processes such as evaporation in thin layers to recover the major part of the caprolactam and recycling the latter in the purification process.Type: GrantFiled: May 29, 2008Date of Patent: July 31, 2012Assignee: Rhodia Polyamide IntermediatesInventors: Daniel Amoros, Philippe Leconte, Pierre Coqueret
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Publication number: 20110257358Abstract: The invention relates to a method for preparing ?-caprolactam comprising deacylating N-acyl-6-aminocaproic acid and forming ?-caprolactam. The deacylation may be carried out chemically or biocatalytically. The invention further relates to a host cell, comprising a recombinant vector comprising a nucleic acid sequence encoding an enzyme capable of catalysing the formation of 6-aminocaproic acid from N-acyl-6-aminocaproic acid.Type: ApplicationFiled: October 9, 2009Publication date: October 20, 2011Inventors: Daniel Mink, Rudolf Philippus Maria Guit, Monika Muller, Petronella Catharina Raemakers-Franken
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Publication number: 20110190488Abstract: The present invention relates to methods of making a cyclic amide. The methods include the step of heating a fermentation broth in a manner effective to produce a cyclic amide, wherein the fermentation broth includes an amino acid or salt thereof. The cyclic amide monomers can be polymerized in a manner effective to form a polyamide. One advantage of the present invention is that lysine and/or salt thereof can be heated to form ?-amino-?-caprolactam while the lysine is still in the fermentation broth. The lysine and/or salt thereof do not need to be purified from the fermentation broth prior to being heated to form ?-amino-?-caprolactam. For example, the fermentation broth does not need to be subjected to an ion exchange process prior to being heated to form ?-amino-?-caprolactam. Avoiding such an ion exchange process can substantially reduce manufacturing costs.Type: ApplicationFiled: July 24, 2009Publication date: August 4, 2011Inventor: Douglas A. Wicks
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Publication number: 20110171699Abstract: The invention relates to a method for preparing 6-aminocaproic acid (hereinafter also referred to as ‘6-ACA’) using a biocatalyst. The invention further relates to a method for preparing e-caprolactam (hereafter referred to as ‘caprolactam’) by cyclising such 6-ACA. The invention further relates to a host cell, a micro-organism, or a polynucleotide which may be used in the preparation of 6-ACA or caprolactam.Type: ApplicationFiled: March 11, 2009Publication date: July 14, 2011Inventors: Petronella Catharina Raemakers-Franken, Martin Schurmann, Axel Christoph Trefzer, Stefaan Marie Andre De Wildeman
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Publication number: 20100317822Abstract: The present invention generally relates to processes for the chemocatalytic conversion of a carbohydrate source to an adipic acid product. The present invention includes processes for the conversion of a carbohydrate source to an adipic acid product via a furanic substrate, such as 2,5-furandicarboxylic acid or derivatives thereof. The present invention also includes processes for producing an adipic acid product comprising the catalytic hydrogenation of a furanic substrate to produce a tetrahydrofuranic substrate and the catalytic hydrodeoxygenation of at least a portion of the tetrahydrofuranic substrate to an adipic acid product. The present invention also includes products produced from adipic acid product and processes for the production thereof from such adipic acid product.Type: ApplicationFiled: June 11, 2010Publication date: December 16, 2010Applicant: RENNOVIA, INC.Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy
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Patent number: 7829654Abstract: A process for continuous or discontinuous synthesis of elastomeric copolyesters from polybutylene terephthalate (PBT) and polyoxytetramethylene glycol is described in which the tetrahydrofuran (THF) obtained as a byproduct in synthesis of polybutylene terephthalate from 1,4-butanediol is rectified and then reacted by ring-opening polymerization to form polyoxytetramethylene glycol which condenses with the free or esterified carboxyl groups of PBT to form the copolyester, whereby chain termination and catalyst deactivation are accomplished by adding 1,4-butanediol without separating the catalyst.Type: GrantFiled: February 23, 2005Date of Patent: November 9, 2010Assignee: Lurgi Zimmer GmbHInventor: Rudolf Kämpf
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Publication number: 20100216958Abstract: Isobutene, isoprene, and butadiene are obtained from mixtures of C4 and/or C5 olefins by dehydrogenation. The C4 and/or C5 olefins can be obtained by dehydration of C4 and C5 alcohols, for example, renewable C4 and C5 alcohols prepared from biomass by thermochemical or fermentation processes. Isoprene or butadiene can be polymerized to form polymers such as polyisoprene, polybutadiene, synthetic rubbers such as butyl rubber, etc. in addition, butadiene can be converted to monomers such as methyl methacrylate, adipic acid, adiponitrile, 1,4-butadiene, etc. which can then be polymerized to form nylons, polyesters, polymethylmethacrylate etc.Type: ApplicationFiled: February 24, 2010Publication date: August 26, 2010Inventors: Matthew W. Peters, Joshua D. Taylor, Leo E. Manzer, David E. Henton
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Publication number: 20100145003Abstract: Catalytic processes for preparing caprolactam, pipecolinic acid, and their derivatives, from lysine or alpha-amino-epsilon-caprolactam starting materials, and products produced thereby. A process for preparing caprolactam or a derivative thereof, the process comprising contacting a reactant comprising lysine or alpha aminocaprolactam with a catalyst and a gas comprising hydrogen gas, in the presence of a solvent. The catalyst may be provided on a support material, such as a transition metal.Type: ApplicationFiled: February 20, 2008Publication date: June 10, 2010Applicant: BOARD of Trustees of Michigan State UniversityInventor: John W. Frost
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Patent number: 7674934Abstract: A process for preparing N-alkenyl compounds by reacting the corresponding NH compounds with alkynes in the liquid phase in the presence of a catalyst, wherein the reaction is carried out in the presence of at least one stabilizer, and the use of stabilizers for increasing the selectivity in a process for preparing N-alkenyl compounds by reacting the corresponding NH compounds with alkynes in the liquid phase in the presence of a catalyst.Type: GrantFiled: August 4, 2005Date of Patent: March 9, 2010Assignee: BASF AktiengesellschaftInventors: Frank Hoefer, Alexandra Brand, Arnd Boettcher, Katrin Baumann, Regina Vogelsang
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Patent number: 7384518Abstract: A method and a plant are disclosed for purifying lactams, particularly lactams obtained by cyclizing hydrolysis of aminonitrile. The purification of ?-caprolactam obtained by cyclizing hydrolysis of aminocapronitrile is described which includes eliminating the ammonia from the reaction medium of the hydrolysis, then recovering the lactam from said medium in purified form. The recovery is carried out by performing at least a distillation of the lactam in the presence of a base producing optionally a fronts fraction comprising compounds more volatile than the lactam, a fraction comprising the lactam to be recovered to the degree of desired purity and a distillation tails comprising the lactam and compounds less volatile than the lactam. The distillation tails are treated by various processes such as evaporation in thin layers to recover the major part of the caprolactam and recycling the latter in the purification process.Type: GrantFiled: May 28, 2001Date of Patent: June 10, 2008Assignee: Rhodia Polyamide IntermediatesInventors: Daniel Amoros, Philippe Leconte, Pierre Coqueret
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Patent number: 6841709Abstract: The present invention is to provide a technology to establish a new cycle-based organic chemical industry, which may be called a polymer cascade (polymer reflux industry) wherein the polymer substances shall not remain the final products, but still give birth to synthetic materials as raw materials for chemical industry and produce useful organic compounds.Type: GrantFiled: October 30, 2001Date of Patent: January 11, 2005Inventor: Masaaki Yoshida
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Patent number: 6838577Abstract: Processes are disclosed for the manufacture of lactones, e.g., caprolactone, from hydoxy acids, e.g., 6-hydroxycaproic acid. The reaction is conducted over a suitable catalyst in the presence of water.Type: GrantFiled: April 17, 2001Date of Patent: January 4, 2005Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Richard A. Galley
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Patent number: 6828413Abstract: The invention relates to a process for the preparation of a polyamide comprising at least a step in which a composition that comprises at least (a) a primary aminocarbonamide and (b) an aminocarboxylic acid and/or a lactam is polymerised, said composition comprising at least (a) 10-90 wt. % primary aminocarbonamide; (b) 10-90 wt. % aminocarboxylic acid and/or lactam; (c) 0-4 wt. % water; the amounts being relative to the sum of the compounds (a+b+c). Preferably the sum of the compounds (a+b+c) is at least 75 wt. % of the total composition, more preferably 85 wt. %, most preferably 90 wt. %. The polyamide obtained with the process has a &eegr;rel of more than 2.2. The process is eminently suitable for the preparation of polyamide-6 (polycapronamide) from a composition comprising 6-aminocapronamide, 6-aminocaproic acid and/or &egr;-caprolactam. This composition is preferably obtained via the reductive amination of a 5-formylyalerate ester, preferably 5-formylmethylvalerate in water.Type: GrantFiled: June 24, 2002Date of Patent: December 7, 2004Assignee: OSM IP Asseta, B.V.Inventors: Cornelis E. Koning, Rudy Rulkens, Nicolaas F. Haasen, Albert A. Van Geenen
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Publication number: 20040176589Abstract: The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.Type: ApplicationFiled: December 10, 2003Publication date: September 9, 2004Inventors: Todd A. Werpy, John G. Frye, James F. White, Johnathan E. Holladay, Alan H. Zacher
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Publication number: 20040030128Abstract: Process for the preparation of a mixture of &egr;-caprolactam and &egr;-caprolactam precursors by reductively aminating 5-formylvaleric acid and/or 5-formylvalerate ester(s) in water with hydrogen and an excess of ammonia in the presence of a hydrogenation catalyst, wherein the process is conducted in a reactor of which the inside reactor wall material is a material containing at most 8 wt. % nickel.Type: ApplicationFiled: July 31, 2003Publication date: February 12, 2004Inventors: Rudolf Philippus Maria Guit, Mathieu Johannes Guillaume Notten, Robert Pestman
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Publication number: 20040024204Abstract: This invention relates to a continuous and efficient method for the manufacture of highly pure caprolactam suitable for the polycondensation of Polyamide 6 (polycaprolactam) from polyamide waste. In particular the invention relates to a method for the manufacture of caprolactam from waste containing polyamides, including the steps a) depolymerisation of the waste containing polyamides, whereby a caprolactam raw material and a flow containing secondary constituents or additives is obtained, b) at least one distillation of the caprolactam raw material, and c) at least one crystallisation of the caprolactam material obtained in step b), by which means caprolactam is obtained, whereby at least part of the caprolactam obtained in step c) with a permanganate number of <10000 sec. and a UV transmission of <85% is added to the waste containing polyamides before and/or during the depolymerisation.Type: ApplicationFiled: June 9, 2003Publication date: February 5, 2004Applicant: ZIMMER AKTIENGESELLSCHAFTInventors: Claus Born, Rudolf Kampf, Joachim Seelig, Reinhard Wolf
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Publication number: 20040014965Abstract: The invention concerns a method for purifying lactams, more particularly lactams obtained by cyclizing hydrolysis of aminonitrile. More particularly, the invention concerns the purification of &egr;-caprolactam obtained by cyclizing hydrolysis of aminocapronitrile which consists in eliminating the ammonia from the reaction medium of the hydrolysis then in recuperating the lactam from said medium in purified form. Said recuperation is carried out by performing at least a distillation of the lactam in the presence of a base producing optionally a fronts fraction comprising compounds more volatile than the lactam, a fraction comprising the lactam to be recuperated to the degree of desired purity and a distillation tails comprising the lactam and compounds less volatile than the lactam. The distillation tails are treated by various processes such as evaporation in thin layers to recuperate the major part of the comprised caprolactam and recycling the latter in the purification process.Type: ApplicationFiled: July 30, 2003Publication date: January 22, 2004Inventors: Daniel Amoros, Philippe Leconte, Pierre Coqueret
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Patent number: 6660857Abstract: A process for the preparation of &egr;-caprolactam starting from 6-aminocaproic acid, 6-aminocaproamide, 6-aminocaproic ester, 6-aminocapronitrile, oligomers or polymers of these compounds or mixtures comprising at least two of these compounds, which process is performed in the presence of N-(5-carboxypentyl)-&egr;-caprolactam and/or derivative thereof in an amount of less than 50 wt. % and more than 0.1 wt. % (based on the total reaction mixture).Type: GrantFiled: August 2, 2002Date of Patent: December 9, 2003Assignee: DSM N.V.Inventors: Frank P. W. Agterberg, Rudolf P. M. Guit, Matthias R. J. Offermanns
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Publication number: 20030225170Abstract: The invention relates to a process for recovering monomeric units of a nylon from carpet material, said carpet material comprising fibres containing said nylon bound to a backing containing one or more non-nylon components, the carpet material containing between 15 and 35 wt.Type: ApplicationFiled: June 3, 2002Publication date: December 4, 2003Inventors: Antonius J.F.M. Courage, Marco J.A. Houben, Mathieu H.M. Mertens, Leonardus J.G. Raets
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Patent number: 6632964Abstract: A process of producing an aliphatic aldehyde-acid (e.g., adipaldehyde-acid) and/or an aliphatic dicarboxylic acid (e.g., adipic acid) comprising oxidizing a cyclic ketone (e.g., cyclohexanone) with molecular oxygen in the presence of a fixed catalyst which comprises a composite of a carrier and at least one metal element belonging to the groups 4 to 11 of the Periodic Table supported on the carrier and has an acid amount of 0.06 mmol/g or more per unit weight of the carrier.Type: GrantFiled: June 22, 2001Date of Patent: October 14, 2003Assignee: Mitsubishi Chemical CorporationInventors: Masaru Fujii, Tohru Setoyama
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Publication number: 20030187249Abstract: The present invention relates to a method and catalysts for the stereoselective addition of a nucleophile to a reactive &pgr;-bond of a substrate. The chiral, non-racemic catalysts of the present invention constitute the first examples of catalysts for nucleophilic additions that comprise a main-group metal and a tri- or tetra-dentate ligand.Type: ApplicationFiled: December 20, 2002Publication date: October 2, 2003Inventors: Eric N. Jacobsen, Matthew S. Sigman
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Publication number: 20030125544Abstract: A process is provided for the preparation of cyclic lactams of formula (II): 1Type: ApplicationFiled: October 29, 2002Publication date: July 3, 2003Inventors: Frank Ohlbach, Andreas Ansmann, Peter Bassler, Rolf-Hartmuth Fischer, Hermann Luyken, Stefan Maixner, Johann-Peter Melder
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Publication number: 20030114664Abstract: The invention relates to a method for producing cyclic lactams of formula (II) by reacting a compound (I) of formula (I) with water in the presence of an organic, liquid dilution agent in the liquid phase. In formula (II), n and m respectively can have the values 0, 1, 2, 3, 4, 5, 6, 7, 8 and 9 and the sum of n+m is at least 3, preferably at least 4 and R1 and R2 represent C1-C6 alkyl, C5-C7 cycloalkyl or C6-C12 aryl groups. In formula (I), R1, R2, m and n are defined as above and R represents nitrile, carboxylic acid amide and carboxylic acid groups. The inventive method is characterized in that a) compound (I) is reacted with water in the liquid phase in the presence of an organic, liquid dilution agent (III) to form a mixture (IV) containing a lactam (II) and said mixture (IV) is subjected to an aqueous treatment to obtain a two-phase system.Type: ApplicationFiled: October 17, 2002Publication date: June 19, 2003Inventors: Frank Ohlbach, Andreas Ansmann, Peter Bassler, Rolf-Hartmuth Fischer, Hermann Luyken, Stefan Maixner, Johann-Peter Melder
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Publication number: 20030065169Abstract: A process for the preparation of &egr;-caprolactam starting from 6-aminocaproic acid, 6-aminocaproamide, 6-aminocaproic ester, 6-aminocapronitrile, oligomers or polymers of these compounds or mixtures comprising at least two of these compounds, which process is performed in the presence of N-(5-carboxypentyl)-&egr;-caprolactam and/or derivative thereof in an amount of less than 50 wt. % and more than 0.1 wt. % (based on the total reaction mixture).Type: ApplicationFiled: August 2, 2002Publication date: April 3, 2003Applicant: DSM N.V.Inventors: Frank P.W. Agterberg, Rudolf P.M. Guit, Matthias R.J. Offermanns
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Patent number: 6521752Abstract: The invention relates to a process to separate linear 5-formylvalerate compound from a crude mixture comprising 5-formylvalerate compound and 2-, 3- and/or 4-formylvalerate compound by vacuum distillation, wherein the distillation is performed in the presence of a phenolic compound with a boiling point which is at least 10° C. higher than the boiling point of the 5-formylvalerate at 0.1-100 kPa.Type: GrantFiled: August 16, 2001Date of Patent: February 18, 2003Assignees: DSM N.V., E.I. Dupont de Nemours and Co.Inventors: Onko J. Gelling, Peter C. Borman
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Patent number: 6452002Abstract: Process for preparing an aqueous mixture of &egr;-caprolactam and 6-aminocaproic acid and/or 6-aminocaproamide which involves, as the reductive amination step, contacting 5-formylvaleric acid and/or an alkyl 5-formylvalerate in water as solvent with hydrogen and an excess of ammonia in the presence of a ruthenium on carrier, as a catalyst, wherein the carrier is titanium oxide, zirconium oxide, graphite or carbon and the catalyst also contains at least one of the metals of group 8-11, or a compound of these metals. The aqueous mixture can be used to prepare &egr;-caprolactam.Type: GrantFiled: March 1, 2001Date of Patent: September 17, 2002Assignees: DSM N.V., E.I. du Pont de Nemours and CompanyInventors: Robert Pestman, Lambertus H. W. M. Van Lieshout
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Patent number: 6392037Abstract: Process for the preparation of &egr;-caprolactam comprising treating 6-aminocaproic acid 6-aminocaproate ester, 6-aminocaproamide, oligomers or polymers of these compounds or mixtures comprising at least two of these compounds in a cyclisation reactor in the presence of superheated steam in which a gaseous product stream comprising &egr;-caprolactam, lights and heavies is obtained, wherein the product stream, after condensation and at least partial removal of water and lights, is split into a &egr;-caprolactam stream and a heavies stream containing heavies and &egr;-caprolactam and the heavies stream is recycled to a cyclisation reactor.Type: GrantFiled: August 10, 2001Date of Patent: May 21, 2002Assignee: DSM N.V.Inventors: Frank P. W. Agterberg, Nicolaas F. Haasen, Rudolf P. M. Guit
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Publication number: 20020058808Abstract: The present invention relates to a process for purifying an impure stream of caprolactam while recovering not only pure caprolactam but also medium-to-high pressure steam. Preferably, the stream of impure or crude caprolactam, which comprises at a minimum a substantial portion of water, is obtained from depolymerization of a polyamide-containing composition. The resulting purified caprolactam will have a purity greater than 90 weight percent and the recovered steam will have a temperature sufficiently high to provide a driving force for use with other equipment, for instance, heat exchange equipment.Type: ApplicationFiled: August 23, 2001Publication date: May 16, 2002Inventors: Peter W.H. Cheng, Jan A.J. Hendrix, Leonardus J.G. Raets
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Publication number: 20020038023Abstract: The invention relates to a process for nylon depolymerization, in which process a multi-component material, comprising nylon and one or more non-nylon components, is fed to a depolymerization zone in which depolymerization of at least part of said nylon is effected, resulting in a product stream and a residue, said product stream containing monomers of said nylon, said residue containing non-nylon components, wherein the nylon content in the residue is measured and used to control the depolymerization process.Type: ApplicationFiled: October 23, 2001Publication date: March 28, 2002Inventors: Leonardus J.G. Raets, Marco J.A. Houben, Michael J.G. Huys, Antonius C. Berghmans
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Publication number: 20020038047Abstract: The invention relates to a process to separate linear 5-formylvalerate compound from a crude mixture comprising 5-formylvalerate compound and 2-, 3- and/or 4-formylvalerate compound by vacuum distillation, wherein the distillation is performed in the presence of a phenolic compound with a boiling point which is at least 10° C. higher than the boiling point of the 5-formylvalerate at 0.1-100 kPa.Type: ApplicationFiled: August 16, 2001Publication date: March 28, 2002Inventors: Onko J. Gelling, Peter C. Borman
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Publication number: 20020038022Abstract: Process for the preparation of &egr;-caprolactam comprising treating 6-aminocaproic acid, 6-aminocaproate ester, 6-aminocaproamide, oligomers or polymers of these compounds or mixtures comprising at least two of these compounds in a cyclization reactor in the presence of superheated steam in which a gaseous product stream comprising &egr;-caprolactam, lights and heavies is obtained, wherein the product stream, after condensation and at least partial removal of water and lights, is split into a &egr;-caprolactam stream and a heavies stream containing heavies and &egr;-caprolactam and the heavies stream is recycled to a cyclization reactor.Type: ApplicationFiled: August 10, 2001Publication date: March 28, 2002Inventors: Frank P.W. Agterberg, Nicolaas F. Haasen, Rudolf P.M Guit
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Patent number: 6362332Abstract: A cyclic lactam and a cyclic amine are coproduced by reacting an aliphatic alpha, omega-diamine with water in the gas phase in the presence of a heterogeneous catalyst.Type: GrantFiled: March 12, 2001Date of Patent: March 26, 2002Assignee: BASF AktiengesellschaftInventors: Martin Merger, Rolf Fischer, Andreas Ansmann
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Patent number: 6353100Abstract: Process for the preparation of &egr;-caprolactam, in which in a step (a) a compound with the general formula: O=CH—(CH2)4—C(O)—R (1) in which R is —OH, —NH2 or O—R′, in which R′ is an organic group with 1 to 10 carbon atoms, is contacted with ammonia and hydrogen in a suitable solvent at elevated pressure in the presence of a hydrogenation catalyst to a mixture of primary amino compounds and &egr;-caprolactam, followed by a separate second step (b) in which the primary amino compounds are reacted to &egr;-caprolactam, wherein the solvent in step (a) is an aqueous medium, including water, the yield to &egr;-caprolactam in step (a) is more than 10%, calculated on the initial molar amount of the compound according to formula (1), that &egr;-caprolactam is separated from the aqueous mixture obtained in step (a) by extraction and that the aqueous mixture resulting from the extraction, containing the primary amino compounds, is used in step (b).Type: GrantFiled: March 1, 1999Date of Patent: March 5, 2002Assignees: DSM N.V., Du Pont de Nemours and CompanyInventors: Rudolf P. M. Guit, Wim Buijs
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Patent number: 6333412Abstract: Process to prepare &egr;-caprolactam starting from a starting mixture containing a 6-aminocaproate ester, in which in a first step (1) the 6-aminocaproate ester is converted into 6-aminocaproic acid and 6-aminocaproamide by reaction with water in the presence of ammonia at a temperature of between 50 and 250° C., with a separate or simultaneous removal of alcohol(s), and in a subsequent step (2) the 6-aminocaproic acid and 6-aminocaproamide are cyclizised at an elevated temperature, wherein in step (1) the 6-aminocaproate ester is converted into 6-aminocaproic acid and 6-aminocaproamide in the presence of an amount higher than 2 wt. % and less than or equal to 25 wt. % NH3 (relative to the total amount of organic compounds, water and ammonia present in step (1)).Type: GrantFiled: August 9, 2000Date of Patent: December 25, 2001Assignees: DSM N.V., E.I. Dupont de Nemours and CompanyInventors: Rudolf P. M. Guit, Samuel L. Lane
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Patent number: 6331624Abstract: A process for the production of 6-aminocaproamide comprising reacting 5-cyanovaleramide with hydrogen in the presence of a metal catalyst. The 6-aminocaproamide is useful, for example, in the production of caprolactam and nylon 6.Type: GrantFiled: April 5, 2000Date of Patent: December 18, 2001Assignee: E.I. du Pont de Nemours and CompanyInventors: Theodore Augur Koch, Alan Martin Allgeier, Mark Jay Harper, Sourav Kumar Sengupta
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Patent number: 6303837Abstract: Using the process according to the invention, it is possible to provide, with few reaction steps, a novel route to &agr;-substituted ring systems, which optionally have further substituents.Type: GrantFiled: August 31, 1999Date of Patent: October 16, 2001Assignee: Bayer AktiengesellschaftInventors: Christoph Gürtler, Manfred Jautelat
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Patent number: 6300496Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) converting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, optionally in the presence of a catalyst or a catalyst and promoter, to one or more substituted or unsubstituted hydroxyamides, e.g. 6-hydroxycaproamide, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g.Type: GrantFiled: October 6, 1999Date of Patent: October 9, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Kurt Damar Olson, Thomas Carl Eisenschmid, David Robert Bryant, Arthur Roy Doumaux, Jr.