Cyclization To Form The Hetero Ring Patents (Class 540/538)
  • Patent number: 12134711
    Abstract: 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: Grant
    Filed: December 9, 2019
    Date of Patent: November 5, 2024
    Assignee: AdvanSix Resins & Chemicals LLC
    Inventors: Jaime A. Flores-Vasquez, Edward Asirvatham, Karttikay Moudgil
  • Patent number: 11753372
    Abstract: 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: Grant
    Filed: December 23, 2019
    Date of Patent: September 12, 2023
    Assignees: AQUAFIL S.P.A., GENOMATICA INC.
    Inventors: Michele Cecchetto, Anacleto Dal Moro, Lauri Hannunpoika Suominen, Michael Japs
  • Patent number: 8946411
    Abstract: 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: Grant
    Filed: February 13, 2013
    Date of Patent: February 3, 2015
    Assignee: Rennovia, Inc.
    Inventors: Eric L. Dias, Vincent J. Murphy, James Longmire, Hong Jiang
  • Publication number: 20140134681
    Abstract: 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: Application
    Filed: December 13, 2013
    Publication date: May 15, 2014
    Inventors: Petronella Catharina RAEMAKERS-FRANKEN, Martin SCHURMANN, Axel Christoph TREFZER, Stefaan Marie Andre DE WILDEMAN
  • Publication number: 20140056803
    Abstract: 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: Application
    Filed: June 11, 2013
    Publication date: February 27, 2014
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin, Debarshi Majumder
  • Publication number: 20130237698
    Abstract: 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: Application
    Filed: August 26, 2011
    Publication date: September 12, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Stefanus Cornelis Hendrikus Turk, Martin Schürmann, Axel Christoph Trefzer, Petronella Catharina Raemakers-Franken, Hildegard Henna Menke
  • Publication number: 20130225785
    Abstract: 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: Application
    Filed: February 13, 2013
    Publication date: August 29, 2013
    Applicant: Rennovia, Inc.
    Inventor: Rennovia, Inc.
  • Publication number: 20130131306
    Abstract: 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: Application
    Filed: June 10, 2011
    Publication date: May 23, 2013
    Applicant: 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
  • Publication number: 20130116398
    Abstract: 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: Application
    Filed: June 10, 2011
    Publication date: May 9, 2013
    Applicant: 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
  • Publication number: 20130085255
    Abstract: 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: Application
    Filed: April 9, 2012
    Publication date: April 4, 2013
    Applicant: Amyris, Inc.
    Inventors: Laetitia Coudray, Vu Bui, John W. Frost, Dirk Schweitzer
  • Publication number: 20130030146
    Abstract: 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: Application
    Filed: December 22, 2010
    Publication date: January 31, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Rudolf Philippus Maria Guit, Thomas Van Der Does, Lourina Madeleine Raamsdonk
  • Publication number: 20120264908
    Abstract: 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: Application
    Filed: March 29, 2012
    Publication date: October 18, 2012
    Applicant: Rennovia, Inc.
    Inventors: Vincent J. MURPHY, Eric L. DIAS, James A. W. SHOEMAKER, Thomas R. BOUSSIE, Zachary M. FRESCO
  • Patent number: 8283466
    Abstract: 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: Grant
    Filed: February 20, 2008
    Date of Patent: October 9, 2012
    Assignee: Board of Trustees of Michigan State University
    Inventor: John W. Frost
  • Patent number: 8231765
    Abstract: 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: Grant
    Filed: May 29, 2008
    Date of Patent: July 31, 2012
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Daniel Amoros, Philippe Leconte, Pierre Coqueret
  • Publication number: 20110257358
    Abstract: 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: Application
    Filed: October 9, 2009
    Publication date: October 20, 2011
    Inventors: Daniel Mink, Rudolf Philippus Maria Guit, Monika Muller, Petronella Catharina Raemakers-Franken
  • Publication number: 20110190488
    Abstract: 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: Application
    Filed: July 24, 2009
    Publication date: August 4, 2011
    Inventor: Douglas A. Wicks
  • Publication number: 20110171699
    Abstract: 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: Application
    Filed: March 11, 2009
    Publication date: July 14, 2011
    Inventors: Petronella Catharina Raemakers-Franken, Martin Schurmann, Axel Christoph Trefzer, Stefaan Marie Andre De Wildeman
  • Publication number: 20100317822
    Abstract: 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: Application
    Filed: June 11, 2010
    Publication date: December 16, 2010
    Applicant: RENNOVIA, INC.
    Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy
  • Patent number: 7829654
    Abstract: 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: Grant
    Filed: February 23, 2005
    Date of Patent: November 9, 2010
    Assignee: Lurgi Zimmer GmbH
    Inventor: Rudolf Kämpf
  • Publication number: 20100216958
    Abstract: 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: Application
    Filed: February 24, 2010
    Publication date: August 26, 2010
    Inventors: Matthew W. Peters, Joshua D. Taylor, Leo E. Manzer, David E. Henton
  • Publication number: 20100145003
    Abstract: 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: Application
    Filed: February 20, 2008
    Publication date: June 10, 2010
    Applicant: BOARD of Trustees of Michigan State University
    Inventor: John W. Frost
  • Patent number: 7674934
    Abstract: 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: Grant
    Filed: August 4, 2005
    Date of Patent: March 9, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Hoefer, Alexandra Brand, Arnd Boettcher, Katrin Baumann, Regina Vogelsang
  • Patent number: 7384518
    Abstract: 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: Grant
    Filed: May 28, 2001
    Date of Patent: June 10, 2008
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Daniel Amoros, Philippe Leconte, Pierre Coqueret
  • Patent number: 6841709
    Abstract: 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: Grant
    Filed: October 30, 2001
    Date of Patent: January 11, 2005
    Inventor: Masaaki Yoshida
  • Patent number: 6838577
    Abstract: 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: Grant
    Filed: April 17, 2001
    Date of Patent: January 4, 2005
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Richard A. Galley
  • Patent number: 6828413
    Abstract: 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: Grant
    Filed: June 24, 2002
    Date of Patent: December 7, 2004
    Assignee: OSM IP Asseta, B.V.
    Inventors: Cornelis E. Koning, Rudy Rulkens, Nicolaas F. Haasen, Albert A. Van Geenen
  • Publication number: 20040176589
    Abstract: 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: Application
    Filed: December 10, 2003
    Publication date: September 9, 2004
    Inventors: Todd A. Werpy, John G. Frye, James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Publication number: 20040030128
    Abstract: 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: Application
    Filed: July 31, 2003
    Publication date: February 12, 2004
    Inventors: Rudolf Philippus Maria Guit, Mathieu Johannes Guillaume Notten, Robert Pestman
  • Publication number: 20040024204
    Abstract: 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: Application
    Filed: June 9, 2003
    Publication date: February 5, 2004
    Applicant: ZIMMER AKTIENGESELLSCHAFT
    Inventors: Claus Born, Rudolf Kampf, Joachim Seelig, Reinhard Wolf
  • Publication number: 20040014965
    Abstract: 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: Application
    Filed: July 30, 2003
    Publication date: January 22, 2004
    Inventors: Daniel Amoros, Philippe Leconte, Pierre Coqueret
  • Patent number: 6660857
    Abstract: 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: Grant
    Filed: August 2, 2002
    Date of Patent: December 9, 2003
    Assignee: DSM N.V.
    Inventors: Frank P. W. Agterberg, Rudolf P. M. Guit, Matthias R. J. Offermanns
  • Publication number: 20030225170
    Abstract: 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: Application
    Filed: June 3, 2002
    Publication date: December 4, 2003
    Inventors: Antonius J.F.M. Courage, Marco J.A. Houben, Mathieu H.M. Mertens, Leonardus J.G. Raets
  • Patent number: 6632964
    Abstract: 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: Grant
    Filed: June 22, 2001
    Date of Patent: October 14, 2003
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaru Fujii, Tohru Setoyama
  • Publication number: 20030187249
    Abstract: 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: Application
    Filed: December 20, 2002
    Publication date: October 2, 2003
    Inventors: Eric N. Jacobsen, Matthew S. Sigman
  • Publication number: 20030125544
    Abstract: A process is provided for the preparation of cyclic lactams of formula (II): 1
    Type: Application
    Filed: October 29, 2002
    Publication date: July 3, 2003
    Inventors: Frank Ohlbach, Andreas Ansmann, Peter Bassler, Rolf-Hartmuth Fischer, Hermann Luyken, Stefan Maixner, Johann-Peter Melder
  • Publication number: 20030114664
    Abstract: 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: Application
    Filed: October 17, 2002
    Publication date: June 19, 2003
    Inventors: Frank Ohlbach, Andreas Ansmann, Peter Bassler, Rolf-Hartmuth Fischer, Hermann Luyken, Stefan Maixner, Johann-Peter Melder
  • Publication number: 20030065169
    Abstract: 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: Application
    Filed: August 2, 2002
    Publication date: April 3, 2003
    Applicant: DSM N.V.
    Inventors: Frank P.W. Agterberg, Rudolf P.M. Guit, Matthias R.J. Offermanns
  • Patent number: 6521752
    Abstract: 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: Grant
    Filed: August 16, 2001
    Date of Patent: February 18, 2003
    Assignees: DSM N.V., E.I. Dupont de Nemours and Co.
    Inventors: Onko J. Gelling, Peter C. Borman
  • Patent number: 6452002
    Abstract: 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: Grant
    Filed: March 1, 2001
    Date of Patent: September 17, 2002
    Assignees: DSM N.V., E.I. du Pont de Nemours and Company
    Inventors: Robert Pestman, Lambertus H. W. M. Van Lieshout
  • Patent number: 6392037
    Abstract: 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: Grant
    Filed: August 10, 2001
    Date of Patent: May 21, 2002
    Assignee: DSM N.V.
    Inventors: Frank P. W. Agterberg, Nicolaas F. Haasen, Rudolf P. M. Guit
  • Publication number: 20020058808
    Abstract: 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: Application
    Filed: August 23, 2001
    Publication date: May 16, 2002
    Inventors: Peter W.H. Cheng, Jan A.J. Hendrix, Leonardus J.G. Raets
  • Publication number: 20020038023
    Abstract: 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: Application
    Filed: October 23, 2001
    Publication date: March 28, 2002
    Inventors: Leonardus J.G. Raets, Marco J.A. Houben, Michael J.G. Huys, Antonius C. Berghmans
  • Publication number: 20020038047
    Abstract: 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: Application
    Filed: August 16, 2001
    Publication date: March 28, 2002
    Inventors: Onko J. Gelling, Peter C. Borman
  • Publication number: 20020038022
    Abstract: 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: Application
    Filed: August 10, 2001
    Publication date: March 28, 2002
    Inventors: Frank P.W. Agterberg, Nicolaas F. Haasen, Rudolf P.M Guit
  • Patent number: 6362332
    Abstract: 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: Grant
    Filed: March 12, 2001
    Date of Patent: March 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Merger, Rolf Fischer, Andreas Ansmann
  • Patent number: 6353100
    Abstract: 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: Grant
    Filed: March 1, 1999
    Date of Patent: March 5, 2002
    Assignees: DSM N.V., Du Pont de Nemours and Company
    Inventors: Rudolf P. M. Guit, Wim Buijs
  • Patent number: 6333412
    Abstract: 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: Grant
    Filed: August 9, 2000
    Date of Patent: December 25, 2001
    Assignees: DSM N.V., E.I. Dupont de Nemours and Company
    Inventors: Rudolf P. M. Guit, Samuel L. Lane
  • Patent number: 6331624
    Abstract: 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: Grant
    Filed: April 5, 2000
    Date of Patent: December 18, 2001
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Theodore Augur Koch, Alan Martin Allgeier, Mark Jay Harper, Sourav Kumar Sengupta
  • Patent number: 6303837
    Abstract: 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: Grant
    Filed: August 31, 1999
    Date of Patent: October 16, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christoph Gürtler, Manfred Jautelat
  • Patent number: 6300496
    Abstract: 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: Grant
    Filed: October 6, 1999
    Date of Patent: October 9, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Kurt Damar Olson, Thomas Carl Eisenschmid, David Robert Bryant, Arthur Roy Doumaux, Jr.