Processes Of Forming 2-pyrrolidone Which Is Unsubstituted Or Alkyl Or Alkenyl Substituted Only Patents (Class 548/552)
  • Publication number: 20150065731
    Abstract: The present invention relates to a process for microwave assisted synthesis of N-methyl pyrrolidone (NMP). Particularly the process relates to the synthesis of N-methyl succinimide or corresponding analogues by using microwave irradiation which on hydrogenation in the presence of a hydrogenating catalyst gives N-methyl pyrrolidone. Compared to the conventional heating microwave process requires less energy inputs and reduces the reaction time drastically from 5-6 h to 2-5 min.
    Type: Application
    Filed: September 4, 2014
    Publication date: March 5, 2015
    Inventors: Praveen Kumar KHATRI, Suman Lata JAIN, Alok Kumar CHATERJEE, Sain BIR
  • Publication number: 20150065339
    Abstract: Catalysts prepared from abundant, cost effective metals, such as cobalt, nickel, chromium, manganese, iron, and copper, and containing one or more neutrally charged ligands (e.g., monodentate, bidentate, and/or polydentate ligands) and methods of making and using thereof are described herein. Exemplary ligands include, but are not limited to, phosphine ligands, nitrogen-based ligands, sulfur-based ligands, and/or arsenic-based ligands. In some embodiments, the catalyst is a cobalt-based catalyst or a nickel-based catalyst. The catalysts described herein are stable and active at neutral pH and in a wide range of buffers that are both weak and strong proton acceptors. While its activity is slightly lower than state of the art cobalt-based water oxidation catalysts under some conditions, it is capable of sustaining electrolysis at high applied potentials without a significant degradation in catalytic current. This enhanced robustness gives it an advantage in industrial and large-scale water electrolysis schemes.
    Type: Application
    Filed: July 2, 2014
    Publication date: March 5, 2015
    Inventors: Aaron J. Bloomfield, Stafford W. Sheehan, Samuel L. Collom, Robert H. Crabtree, Paul T. Anastas
  • Patent number: 8501963
    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: Grant
    Filed: July 1, 2011
    Date of Patent: August 6, 2013
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 8466297
    Abstract: The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compounds of general formula I used for treatment of epilepsy, neuropathic pain, anxiety and social phobia. The invention describes preparation of enantiomerically pure (S)-Pregabalin from chiral pyrrolidin-2-one of formula IV.
    Type: Grant
    Filed: November 1, 2010
    Date of Patent: June 18, 2013
    Inventor: Milan Soukup
  • Publication number: 20120123134
    Abstract: The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compounds of general formula I used for treatment of epilepsy, neuropathic pain, anxiety and social phobia. The invention describes preparation of enantiomerically pure (S)-Pregabalin from chiral pyrrolidin-2-one of formula IV.
    Type: Application
    Filed: November 1, 2010
    Publication date: May 17, 2012
    Applicant: Drug Process Licensing Associates LLC
    Inventor: Milan Soukup
  • Publication number: 20110263874
    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: July 1, 2011
    Publication date: October 27, 2011
    Inventors: Todd A. Werpy, John G. Frye, JR., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7973177
    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-methylpyrrolidinone (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: Grant
    Filed: February 9, 2010
    Date of Patent: July 5, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7939676
    Abstract: A process for the manufacturing of levetiracetam, wherein said process comprises the steps of: (1) reacting the (?)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid with a substoichiometric amount of an activating agent in an alcoholic solvent, and (2) subjecting the resulting reaction solution of step (1) to an ammonolysis process with gaseous ammonia.
    Type: Grant
    Filed: September 17, 2009
    Date of Patent: May 10, 2011
    Assignee: Zach System S.p.A.
    Inventors: Corrado Colli, Massimiliano Forcato, Livius Cotarca
  • Publication number: 20110034706
    Abstract: A process for preparing N-vinylpyrrolidone by reacting 2-pyrrolidone with acetylene, wherein the 2-pyrrolidone used as a starting material (referred to hereinafter as starting 2-pyrrolidone) comprises less than 1 part by weight of ?-butyrolactone per 100 parts by weight of 2-pyrrolidone.
    Type: Application
    Filed: November 26, 2008
    Publication date: February 10, 2011
    Applicant: BASF SE
    Inventors: Wolfgang Staffel, Stefan Kaeshammer, Roland Kessinger, Regina Vogelsang, Axel Paul, Lembit Tuttelberg
  • Publication number: 20100286399
    Abstract: A process for preparing an N-alkyllactam with improved color quality, wherein from 0.01 to 10% by weight of a C1-10-alcohol or a compound which releases from 0.01 to 10% by weight of a C1-10-alcohol is added to the N-alkyllactam. A mixture comprising at least 99.0% by weight of an N-alkyllactam and in the range from 100 to 5000 ppm by weight of a C1-10-alcohol or of an acetal, aminal or of an orthoester which releases in the range from 100 to 5000 ppm by weight of a C1-10-alcohol.
    Type: Application
    Filed: July 23, 2010
    Publication date: November 11, 2010
    Applicant: BASF SE
    Inventors: Tobias Wabnitz, Rolf Pinkos, Karl Ott
  • Publication number: 20100145072
    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-methylpyrrolidinone (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: February 9, 2010
    Publication date: June 10, 2010
    Applicant: BATTELLE MEMORIAL INSTITUTE
    Inventors: Todd A. Werpy, John G. Frye, JR., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7674916
    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: Grant
    Filed: March 19, 2007
    Date of Patent: March 9, 2010
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frey, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • 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
  • Publication number: 20090182139
    Abstract: A process for preparing an N-alkyllactam with improved color quality, wherein from 0.01 to 10% by weight of a C1-10-alcohol or a compound which releases from 0.01 to 10% by weight of a C1-10-alcohol is added to the N-alkyllactam. A mixture comprising at least 99.0% by weight of an N-alkyllactam and in the range from 100 to 5000 ppm by weight of a C1-10-alcohol or of an acetal, aminal or of an orthoester which releases in the range from 100 to 5000 ppm by weight of a C1-10-alcohol.
    Type: Application
    Filed: March 29, 2007
    Publication date: July 16, 2009
    Applicant: BASF SE
    Inventors: Tobias Wabnitz, Rolf Pinkos, Karl Ott
  • Patent number: 7524980
    Abstract: Compounds expressed by the following formula (1) or pharmaceutically permissible solvate thereof which is effective for treating Paget's disease of bone, hypercalcemia or osteoporosis. In the formula, R1 is a C2-C10 alkyl group, or a C7-C15 aralkyl group whose aromatic ring is optionally substituted with a C1-C6 alkyl group, a C1-C6 alkoxyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group; and R2 is a C1-C10 alkyl group, or a C7-C15 aralkyl group whose aromatic ring is optionally substituted with a C1-C6 alkyl group, a C1-C6 alkoxyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group.
    Type: Grant
    Filed: November 4, 2004
    Date of Patent: April 28, 2009
    Assignee: Teijin Pharma Limited
    Inventors: Kazuo Nagasawa, Yuichi Hashimoto, Yuko Kato
  • Publication number: 20070219265
    Abstract: A compound comprising or a pharmaceutically acceptable salt thereof, or a prodrug thereof is disclosed herein. Y, A, and B are as described herein. Methods, compositions, and medicaments related to these compounds are also disclosed.
    Type: Application
    Filed: March 20, 2007
    Publication date: September 20, 2007
    Inventors: David W. Old, Danny T. Dinh
  • Patent number: 7199250
    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: Grant
    Filed: December 10, 2003
    Date of Patent: April 3, 2007
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7193091
    Abstract: A process for coproducing alkyl-substituted or unsubstituted THF and pyrrolidones by catalytically hydrogenating C4-dicarboxylic acids and/or derivatives thereof in the gas phase in the presence of copper catalysts and reacting GBL with ammonia or primary amines to give pyrrolidones.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: March 20, 2007
    Assignee: Basf Aktiengesellschaft
    Inventors: Rolf-Hartmuth Fischer, Markus Rösch, Nils Bottke, Alexander Weck, Gunther Windecker, Michael Hesse, Holger Borchert, Stephan Schlitter
  • Patent number: 7164031
    Abstract: A process for continuously preparing 2-pyrrolidone by reacting gamma-butyrolactone with ammonia in the liquid phase in the presence of water, wherein the reaction is carried out at a temperature of from 275 to 300° C. and an absolute pressure of from 140 to 180 bar.
    Type: Grant
    Filed: August 30, 2002
    Date of Patent: January 16, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Rudloff, Peter Stops, Erhard Henkes, Helmut Schmidtke, Rolf-Hartmuth Fischer, Manfred Julius, Rolf Lebkücher, Karl-Heinz Ross
  • Patent number: 7129362
    Abstract: This invention relates to a process for producing 5-methyl-N-aryl-2-pyrrolidone, 5-methyl-N-alkyl-2-pyrrolidone, and 5-methyl-N-cycloalkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl amines utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: February 4, 2005
    Date of Patent: October 31, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 7030074
    Abstract: This invention relates to a process for producing 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl cyano compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: October 15, 2004
    Date of Patent: April 18, 2006
    Assignee: E I. duPont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 7015320
    Abstract: The present invention relates generally to processes for the efficient production optically active 3-substituted lactams of formula (I) process, comprising: contacting a compound of formula (II): with hydrogen under a suitable pressure in the presence of an iridium complex of the formula (R2)IrL+X? wherein L is a chelating diene, X is a non coordinating anion, and R2 is selected from
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: March 21, 2006
    Assignee: Bristol-Myers Squibb Company
    Inventors: William A. Nugent, Tai Yue
  • Patent number: 7014697
    Abstract: This invention relates to a process for producing 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl cyano compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: October 15, 2004
    Date of Patent: March 21, 2006
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 7002024
    Abstract: This invention relates to a process for producing N-aryl-2-lactams and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl amines utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: February 21, 2006
    Assignee: E. I. duPont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6995275
    Abstract: This invention relates to a process for producing N-aryl-2-lactams, N-alkyl-2-lactams, and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl or alkyl nitro compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: September 8, 2004
    Date of Patent: February 7, 2006
    Assignee: E.I. duPont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6992195
    Abstract: This invention relates to a process for producing N-aryl-2-lactams and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl amines utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: January 31, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6987191
    Abstract: A process for the production of N-methyl pyrrolidone using gamma butyrolactone and mixed methylamines as starting materials, in a continuous process, in such operating conditions as to allow the production of high purity N-methyl pyrrolidone in high yields.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: January 17, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Aldo Bertola, Salvatore Cassarino, Philippe Raucq
  • Patent number: 6987192
    Abstract: This invention relates to a process for producing N-aryl-2-lactams, N-alkyl-2-lactams, and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl or alkyl nitro compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: September 8, 2004
    Date of Patent: January 17, 2006
    Assignee: E.I. duPont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6984736
    Abstract: This invention relates to a process for producing N-aryl-2-lactams, N-alkyl-2-lactams, and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl or alkyl nitro compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: September 8, 2004
    Date of Patent: January 10, 2006
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6982339
    Abstract: This invention relates to a process for producing N-aryl-2-lactams and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl amines utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: January 3, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6930126
    Abstract: This invention relates to a process for producing 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl cyano compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: October 15, 2004
    Date of Patent: August 16, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6916842
    Abstract: This invention relates to a process for producing 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl cyano compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: July 12, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6906200
    Abstract: N-vinyl pyrrolidone is produced by dehydration of N-hydroxyethyl pyrrolidone in the presence of an amorphous mixed oxide catalyst such as an amorphous Ca/Zn oxide catalyst.
    Type: Grant
    Filed: October 1, 2002
    Date of Patent: June 14, 2005
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Andrew P. Kahn
  • Patent number: 6828277
    Abstract: This invention relates to a process for producing N-aryl-2-lactams, N-alkyl-2-lactams, and N-cycloalky-2-lactams by reductive amination of lactones with aryl or alkyl nitro compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: December 7, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6828278
    Abstract: This invention relates to a process for producing N-aryl-2-lactams and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl amines utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: December 7, 2004
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Publication number: 20040242900
    Abstract: A process for continuously preparing 2-pyrrolidone by reacting gamma-butyrolactone with ammonia in the liquid phase in the presence of water, wherein the reaction is carried out at a temperature of from 275 to 300° C. and an absolute pressure of from 140 to 180 bar.
    Type: Application
    Filed: February 24, 2004
    Publication date: December 2, 2004
    Inventors: Martin Rudloff, Peter Stops, Erhard Henkes, Helmut Schmidtke, Rolf-Hartmuth Fischer, Manfred Julius, Rolf Lebkucher, Karl-Heinz Ross
  • Patent number: 6818593
    Abstract: This invention relates to a process for producing 5-methyl-N-aryl-2-pyrrolidone, 5-methyl-N-cycloalkyl-2-pyrrolidone, and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with nitro compounds utilizing a metal catalyst, which is optionally supported.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: November 16, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Publication number: 20040192932
    Abstract: This invention relates to a process for producing N-(methyl aryl)-2-lactams, N-alkyl-2-lactams, and N-(methyl cycloalkyl)-2-lactams by reductive amination of lactones with aryl or alkyl cyano compounds utilizing a metal catalyst, which is optionally supported.
    Type: Application
    Filed: March 24, 2003
    Publication date: September 30, 2004
    Inventor: Leo Ernest Manzer
  • Patent number: 6726811
    Abstract: A method for obtaining high purity N-(2-hydroxyethyl)-2-pyrrolidone satisfactory for use as an intermediate material for N-vinyl-2-pyrrolidone from a reaction liquid formed of a reaction between y-butyrolactone and 2-aminoethanol, i.e., a liquid containing N-(2-hydroxyethyl)-2-pyrrolidone, compounds having boiling points lower than that of N-(2-hydroxyethyl)-2-pyrrolidone and compounds having boiling points higher than that of N-(2-hydroxyethyl)-2-pyrrolidone. The method is characterized by distilling said reaction liquid using a distillation column, whereby obtaining a liquid containing the compounds having the lower boiling points than that of N-(2-hydroxyethyl)-2-pyrrolidone and N-(2-hydroxyethyl)-2-pyrrolidone as a distillate liquid from the column top and a liquid containing compounds having boiling points higher than that of N-(2-hydroxyethyl)-2-pyrrolidone as a bottom liquid.
    Type: Grant
    Filed: March 26, 2002
    Date of Patent: April 27, 2004
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Shukichi Ugamura, Hideto Sugiura, Hitoshi Yano
  • Patent number: 6706893
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: March 16, 2004
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6673920
    Abstract: A process for preparing N-alkenyl-amides by reacting the corresponding NH-amides with acetylenes in the liquid phase in the presence of basic alkali metal compounds and of a cocatalyst comprises using as the cocatalyst diols of the general formula (I) where X is branched or unbranched alkylene selected from the group consisting of where R1 to R6 are independently hydrogen or C1- to C4-alkyl; or branched or unbranched cyclic alkylene of 3 to 14 carbon atoms including 3 to 12 ring carbon atoms, their monoalkenyl ethers, their dialkenyl ethers or mixtures thereof.
    Type: Grant
    Filed: June 19, 2002
    Date of Patent: January 6, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Preiss, Arnd Böttcher, Rolf Pinkos, Rudolf Erich Lorenz
  • Patent number: 6670483
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: December 30, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6632951
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: October 14, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6624303
    Abstract: A process for preparing N-alkenyl-amides by reacting the corresponding NH-amides with acetylenes in the liquid phase in the presence of basic alkali metal compounds and of a cocatalyst comprises using as the cocatalyst compounds of the general formulae (Ia) and/or (Ib) R1O—(CH2CH2CH2CH2O)n—H  (Ia): R1O—(CH2CH2CH2CH2O)n—R2,  (Ib): where n is 1, 2 or 3 and R1 and R2 are independently C1- to C6-alkyl or C2- to C6-alkenyl, or together a butenyl unit.
    Type: Grant
    Filed: June 19, 2002
    Date of Patent: September 23, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Böttcher, Rolf Pinkos, Thomas Preiss, Rudolf Erich Lorenz
  • Patent number: 6603021
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: August 5, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Publication number: 20030125570
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Application
    Filed: October 25, 2002
    Publication date: July 3, 2003
    Inventors: Todd Werpy, John G. Frye, Yong Wang, Alan H. Zacher
  • Publication number: 20030120087
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Application
    Filed: October 25, 2002
    Publication date: June 26, 2003
    Inventors: Todd Werpy, John G. Frye, Yong Wang, Alan H. Zacher
  • Publication number: 20030097006
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Application
    Filed: June 18, 2001
    Publication date: May 22, 2003
    Inventors: Todd Werpy, John G. Frye, Yong Wang, Alan H. Zacher
  • 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: RE39744
    Abstract: In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2): wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n=1 to 3; or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.
    Type: Grant
    Filed: March 5, 1998
    Date of Patent: July 24, 2007
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai