Processes Of Forming 2-pyrrolidone Which Is Unsubstituted Or Alkyl Or Alkenyl Substituted Only Patents (Class 548/552)
  • Publication number: 20020128301
    Abstract: Non-nucleoside reverse transcriptase inhibitors of formula (P-1) wherein: Ar1 is an unsaturated, optionally substituted, mono or bicyclic ring structure comprising 0 to 3 hetero atoms selected from S, O and N; Ar2 is an aromatic, optionally substituted, monocyclic ring structure comprising at least one nitrogen hetero atom and zero to two further hetero atoms selected from S, O and N; R4 and R5 are independently H or C3-C8 cycloalkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C5 alkoxy, C1-C4 alkanoyloxy, C1-C4 alkylthio, amino, carboxy, carbamoyl, cyano, halo, hydroxy, aminomethyl, hydroxymethyl, carboxymethyl, or halo substituted C1-C6 alkyl mercapto, nitro; or R4 and RS join to form a 3-6 membered, optionally substituted ring structure; R6 is 0 or S; Rx is the residue of a natural or unnatural amino acid; and L* is a linker moiety which is ether-, carbonate- or ester-bound to the adjacent oxygen and ester linked to Rx; and pharmaceutically acceptable salts thereof are anti-HIV agents with favourable ph
    Type: Application
    Filed: August 10, 2001
    Publication date: September 12, 2002
    Inventors: Xiao-Xiong Zhou, Nils-Gunnar Johansson, Horst Wahling, Christian Sund, Lourdes Salvador, Stefan Lindstrom, Hans Wallberg, Christer Sahlberg
  • Patent number: 6436243
    Abstract: A process for recovering N-vinyl-2-pyrrolidone is provided which allows to recover N-vinyl-2-pyrrolidone efficiently and steadily and in high purity by continuous distillation from a mixed liquid containing N-vinyl-2-pyrrolidone, N-(2-hydroxyethyl)-2-pyrrolidone, compounds having a higher boiling point than N-vinyl-2-pyrrolidone and water. The process includes continuously distilling the mixed liquid using a distilling column, controlling the temperature of the bottom liquid of the distilling column at 180° C. or less.
    Type: Grant
    Filed: October 18, 2000
    Date of Patent: August 20, 2002
    Assignee: Nippon Shokubai Co LTD
    Inventors: Yoshinari Yamaguchi, Hitoshi Yano, Akira Kurusu, Yuuji Shimasaki
  • Patent number: 6392104
    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: November 10, 1998
    Date of Patent: May 21, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai
  • Patent number: 6348601
    Abstract: N-Methyl-2-pyrrolidone (NMP) is prepared by preparing a mixture comprising monomethylamine, dimethylamine and trimethylamine and ammonia in a first process step by reacting ammonia with methanol at elevated temperature in the presence of a catalyst, separating 10 off the ammonia, reacting the mixture comprising the methylamines with gamma-butyrolactone (&ggr;-BL), in a molar ratio of monomethylamine to &ggr;-BL of at least 1 in a second process step at elevated temperature and superatmospheric pressure, separating NMP and unreacted methylamines from the reaction product and returning unreacted methylamines to the first process step for reaction with methanol and ammonia.
    Type: Grant
    Filed: February 1, 2001
    Date of Patent: February 19, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Ohlbach, Johann-Peter Melder, Karl-Heinz Ross, Martin Rudloff, Jörg Liebe
  • Publication number: 20010018528
    Abstract: N-Methyl-2-pyrrolidone (NMP) is prepared by preparing a mixture comprising monomethylamine, dimethylamine and trimethylamine and ammonia in a first process step by reacting ammonia with methanol at elevated temperature in the presence of a catalyst, separating off the ammonia, reacting the mixture comprising the methylamines with gamma-butyrolactone (&ggr;-BL), in a molar ratio of monomethylamine to &ggr;-BL of at least 1 in a second process step at elevated temperature and superatmospheric pressure, separating NMP and unreacted methylamines from the reaction product and returning unreacted methylamines to the first process step for reaction with methanol and ammonia.
    Type: Application
    Filed: February 1, 2001
    Publication date: August 30, 2001
    Inventors: Frank Ohlbach, Johann-Peter Melder, Karl-Heinz Ross, Martin Rudloff, Jorg Liebe
  • Patent number: 6248902
    Abstract: A process for the production of N-methyl-pyrrolidone obtained by reaction of gammabutyrolactone and mononmethylamine; wherein the synthesis is carried out by a continuous non catalytic process in liquid phase, via three distinct reaction stages connected in series.
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: June 19, 2001
    Assignee: Pantochim S. A.
    Inventor: Aldo Bertola
  • Patent number: 6008375
    Abstract: A process for manufacturing gamma-butyrolactone by the catalytic hydrogenation of maleic anhydride, succinic anhydride or their acids in the vapor phase in the presence of catalysts based on copper oxide and aluminum oxide in reduced form is described. The process is characterized in that a catalyst is employed to conduct the reaction which is formed on the basis of 50 to 95 % by weight copper oxide, 3 to 30 % by weight aluminum oxide and 0 to 25 % by weight of a binder. Preferably the catalyst is formed on the basis of 83.5 to 85.5 % by weight copper oxide, 9 to 11 % by weight aluminum oxide, and 4.5 to 6.5 % by weight graphite. The reaction mixture obtained can be used directly without separating off the water, e.g. for manufacturing N-methylpyrrolidone.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: December 28, 1999
    Assignee: Akzo Nobel NV
    Inventors: Manfred J. Bergfeld, Kurt Uihlein
  • Patent number: 5994562
    Abstract: In a process for preparing N-alkenylcarboxamides by dehydration of N-(2-hydroxyalkyl)carboxamides and/or diethers thereof in the presence of a catalyst, molecular sieves, in particular zeolites, are used as catalyst.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: November 30, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Matthias Eiermann, Thomas Narbeshuber, Eugen Gehrer
  • Patent number: 5958821
    Abstract: A substrate (e.g., a cycloalkane, a polycyclic hydrocarbon, an aromatic compound having a methyl group or methylene group adjacent to an aromatic ring) is oxidized with oxygen in the presence of an oxidation catalyst comprising an imide compound of the following formula (1) (e.g., N-hydroxyphthalimide), and a co-catalyst (except phosphovanadomolybdic acid) containing an element selected from the group consisting of Group 2A elements of the Periodic Table of Elements, transition metals (Group 3A to 7A elements, Group 8 elements, Group 1B elements and Group 2B elements of the Periodic Table of Elements) and Group 3B elements of the Periodic Table of Elements, for the formation of an oxide (e.g., a ketone, an alcohol, a carboxylic acid): ##STR1## wherein R.sup.1 and R.sup.2 represent a substituent such as a hydrogen atom or a halogen atom, or R.sup.1 and R.sup.2 may together form a double bond or an aromatic or nonaromatic 5- to 12-membered ring, X is O or OH, and n is 1 to 3.
    Type: Grant
    Filed: September 24, 1997
    Date of Patent: September 28, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 5945544
    Abstract: A process for producing an N-vinyllactam by reacting a lactam with acetylene in the presence of a particular catalyst (an alkali metal alcoholate between an alicyclic alcohol and an alkali metal) in a nonaqueous system at an acetylene partial pressure of 0 to 10 kg/cm.sup.2 .multidot.G.In the above process, the vinylation of lactam with acetylene is conducted at a low acetylene partial pressure in one step while the formation of by-product is kept minimum, whereby a high conversion and a high selectivity of lactam can be achieved.
    Type: Grant
    Filed: August 27, 1998
    Date of Patent: August 31, 1999
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Hideki Ohmori, Toshiyuki Fukudome, Tomonori Hakozaki, Tomo Oikawa, Satoshi Kakuta, Hidenobu Oda
  • Patent number: 5847213
    Abstract: There is provided a process for producing a tertiary amine compound in one step without using any subsidiary raw material or any solvent, by subjecting a secondary amine compound and an alcohol to an intermolecular dehydration reaction in a gas phase. The process uses, as a catalyst, an oxide containing an alkali metal element and/or an alkaline earth metal element and silicon.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: December 8, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Akira Kurusu, Yuuji Shimasaki
  • Patent number: 5700946
    Abstract: The present invention provides a process for producing an N-vinyl compound, which comprises subjecting an N-(-alkoxyalkyl) compound to gas phase intramolecular alcohol elimination to convert said compound to an N-vinyl compound directly in one step, wherein a solid oxide containing phosphorus and an alkali metal and/or an alkaline earth metal is used as a catalyst. This process need not use any solvent or any auxiliary raw material and consequently can produce an N-vinyl compound simply and safely without generating any waste material derived from the auxiliary raw material.
    Type: Grant
    Filed: April 17, 1996
    Date of Patent: December 23, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yuuji Shimasaki, Hideyuki Kanbe, Akira Kurusu
  • Patent number: 5670639
    Abstract: N-Vinyllactams of the general formula I ##STR1## where n is from 1 to 3, are prepared by a process which comprises reaction of a lactam of the general formula II ##STR2## where n is from 1 to 3, with from 10 to 90 percent by weight of an aqueous alkali metal hydroxide solution with distillation at from 50.degree. to 250.degree. C. and from 1 to 100 mbar and with a residence time of from 0.1 to 5 hours and subsequent reaction with acetylene at from 60.degree. to 250.degree. C. and from 1 to 100 bar.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: September 23, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Schmidt-Radde, Marc Heider, Albrecht Dams, Harald Rust
  • Patent number: 5665889
    Abstract: The present invention relates to a method for the production of N-vinyl-2-pyrrolidone with high selectivity. The method is characterized in subjecting 2-pyrrolidone and acetylene to vinylation by using hydroxy end-capped ether oligomers having a molecular weight less than 1000 or linear diols having at least 4 carbon atoms as co-catalysts under the catalyzation of alkali metal salts. At a vinylation temperature of 100.degree.-200 .degree. C., a reaction pressure of 7.5-30 atm and a reaction time period of 3-20 hours, N-vinyl-2-pyrrolidones are obtained with yields above 90%.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: September 9, 1997
    Assignee: Industrial Technology Research Institute
    Inventors: Shiao-Jung Chu, Pine-Sci Kuo, Chu-Chang Dai, Hsi-Yen Hsu, Ching-Tang Lin
  • Patent number: 5641881
    Abstract: Preparation of N-alkenylcarboxamides of the general formula I ##STR1## where at least one of the radicals R.sup.1 is hydrogen and the second radical R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 -alkyl group, the radical R.sup.2 is an aliphatic, cycloaliphatic, araliphatic or aromatic radical which can be bonded to the radical R.sup.3 to give a 3- to 10-membered bridge member, and the radical R.sup.3 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, from an alkenyl carboxylate of the general formula II ##STR2## where R.sup.1 has the meanings indicated above and R.sup.4 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, and a carboxamide of the general formula III ##STR3## where the radicals R.sup.2 and R.sup.3 have the meanings indicated above, by reacting the starting compounds in the presence of a base is described.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: June 24, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider
  • Patent number: 5625076
    Abstract: The present invention provides a catalyst which is an oxide comprising silicon and at least one element selected from the group consisting of alkali metals and alkaline earth metals and which is used for gas-phase intramolecular dehydration of a tertiary N-(2-hydroxyalkyl) carboxylic acid amide to synthesize a tertiary N-alkenyl carboxylic acid amide. This catalyst enables continuous and efficient production of a tertiary N-alkenyl carboxylic acid amide from a tertiary N-(2-hydroxyalkyl) carboxylic acid amide without using any auxiliary raw material, and consequently allows for simple and safe production of a tertiary N-alkenyl carboxylic acid amide without generating any by-product (waste product) derived from the auxiliary raw material.
    Type: Grant
    Filed: September 18, 1995
    Date of Patent: April 29, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yuuji Shimasaki, Hitoshi Yano, Kimio Ariyoshi
  • Patent number: 5571913
    Abstract: The invention relates to a process for preparing a lactam from an alicyclic ketoxime in the presence of a lactim-O-sulphonic acid and a solvent, the reaction being carried out in the presence of an acid cation exchanger. The invention relates in particular to a process in which the alicyclic ketoxime is represented by the following general formula: ##STR1## where R is a linear or branched alkylidene group containing from 3 to 20 carbon atoms.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: November 5, 1996
    Assignee: DSM N.V.
    Inventor: Petrus J. H. Thomissen
  • Patent number: 5569770
    Abstract: The present invention relates to a method for the production of N-vinyl-2-pyrrolidone by gas-phase reaction at atmospheric pressure. The method is characterized in that a gas-phase reaction is conducted by using N-.beta.-Hydroxyethyl-2-Pyrrolidones serving as raw materials, at a temperature of 300.degree.-450.degree. C., a space velocity of 500-4500 hr.sup.-1 in the presence of a mixed oxide of group IV elements, or an oxide of group IV elements, which has been modified by group I or group II elements.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: October 29, 1996
    Assignee: Industrial Technology Research Institute
    Inventors: Pine-Sci Kuo, Shiao-Jung Chu, Chu-Chang Dai, Hsi-Yen Hsu, Ching-Tang Lin, Yi-Yun Lin
  • Patent number: 5539102
    Abstract: The method for producing a sulfamide according to the present invention includes the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative. In one embodiment, the sulfamide is represented by Formula I, the alcohol is represented by Formula II, and the oxycarbonylsulfamide compound is represented by Formula III:R.sup.3 NHSO.sub.2 NR.sup.1 R.sup.2 (I)wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, a heterocyclic group, and alkyl substituted with the heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, an azetidinone ring, a cephem ring, a penem ring, and a carbapenem ring; R.sup.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: July 23, 1996
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Yuji Sendo, Makoto Kii, Yasuhiro Nishitani, Tadashi Irie, Yutaka Nishino
  • Patent number: 5508396
    Abstract: A process for preparing an N-alkyllactam, comprising the steps of:(a) reacting a lactam with an alkali metal alkoxide at 130.degree.-170.degree. C. and removing the alcohol formed by distillation;(b) reacting the product from step (a), if desired in a mixture with the product from step (e), with an alkyl halide in a solvent which is(i) an ethylene glycol dialkyl ether of the formula R--O--(CH.sub.2 --CH.sub.2 --O).sub.m R, where R in C.sub.1 -C.sub.
    Type: Grant
    Filed: April 13, 1995
    Date of Patent: April 16, 1996
    Assignee: Huels Aktiengesellschaft
    Inventor: Klaus-Dieter Steffen
  • Patent number: 5496958
    Abstract: A process for the preparation of a 5-vinylpyrrolidone of the formula ##STR1## wherein each of R.sup.1 and R.sup.2 is hydrogen or alkyl and R.sup.3 is preferably hydrogen but may further represent alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl or a 5- to 6-membered aromatic or non-aromatic heterocyclic group containing 1 to 3 nitrogen atoms and/or an oxygen or sulfur atom, the process being carried out in two steps, first to react a 3-formylpropionic acid ester of the formula ##STR2## where each of R.sup.1 and R.sup.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and R.sup.4 is hydrogen, alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl, with a vinylymagnesium halide of the formulaCH.sub.2 .dbd.CH--Mg--X V,where X is chlorine, bromine or iodine, at a temperature of from -30.degree. to 100.degree. C., under a pressure from 0.001 to 10 bar and in a molar ratio of V:IV of from 0.3:1 to 3:1 to obtain as an intermediate product a gamma-vinylbutyrolactone of the formula ##STR3## where R.sup.1 and R.sup.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: March 5, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Werner Hoffmann, Ernst Langguth, Hardo Siegel
  • Patent number: 5478950
    Abstract: The invention relates to a process for producing pyrrolidone and N-alkyl pyrrolidones from saturated or unsaturated 1,4-dicarboxylic acids or their anhydrides, hydrogen, and a primary amine, characterized in that the dicarboxylic acid or its anhydride is allowed to react in an appropriate reactor with hydrogen or ammonia via a first catalyst bed and the unisolated intermediate product is subsequently reacted with the primary amine or ammonia directly via a second, downstream catalyst bed.
    Type: Grant
    Filed: August 8, 1994
    Date of Patent: December 26, 1995
    Assignee: Akzo Nobel N.V.
    Inventors: Manfred Bergfeld, Gunter Wiesgickl
  • Patent number: 5434273
    Abstract: The preparation of N-substituted 2-pyrrolidones (I) by the reaction of maleic acid, fumaric acid, or succinic acid or functional derivatives of these acids (compounds II) with a primary amine (III) or by the reaction of amides or imides derived from II and III under hydrogenating conditions in a synthesis stage followed by isolation, by distillation, of I and other volatile components from the resulting reaction mixture, in which the residues present following distillation are subjected to further hydrogenation treatment and the compound (I) thus formed is isolated by distillation.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: July 18, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer
  • Patent number: 5410070
    Abstract: Process for the preparation of N-alkenylpyrrolidones of the general formula ##STR1## in which R denotes hydrogen or C.sub.1 -C.sub.20 alkyl, by the reaction of an N-alkylpyrrolidone of the general formula ##STR2## in which R has the aforementioned meanings, and x and Y stand for OH, C.sub.1 -C.sub.20 alkoxy or C.sub.2 -C.sub.20 alkoxycarbonyl, provided that one of the two radicals x and denotes hydrogen, at temperatures ranging from 200.degree. to 600.degree. C. and pressures ranging from 0.1 to 5 bar, wherein the process is carried out in the presence of an acid heterogenous catalyst except for an oxide of a Group IIb, Group IIIb, Group IVb, and Group VIb metal.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: April 25, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Franz, Michael Huellmann
  • Patent number: 5401856
    Abstract: A cyclocarbonylation process for making pyrrolidones under mild temperature and pressure conditions is disclosed. In the process, an allylic amine reacts with carbon monoxide in the presence of a rhodium carbonyl catalyst and an amount of a pyridine promoter effective to enhance the yield of pyrrolidone obtained in the process compared with the yield obtained in the absence of the promoter. The process can be used to make N-methyl-2-pyrrolidone from N-methylallylamine.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: March 28, 1995
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Roger A. Grey, Diandre Armstead
  • Patent number: 5399712
    Abstract: The invention relates to a process for the manufacture of substituted maleimides of the formula ##STR1## wherein R.sup.1 is alkyl, aryl or heteroaryl and R.sup.2 is hydrogen, alkyl, alkoxycarbonyl, aryl or heteroaryl, by reacting an activated glyoxylate of the formula ##STR2## wherein R.sup.1 has the above significance and X is a leaving atom or group,with an imidate of the formula ##STR3## wherein R.sup.2 has the above significance, R.sup.3 is alkyl, aryl or trialkylsilyl and Y is oxygen or sulfur, in the presence of a base and, after treating the resulting reaction product obtained in which R.sup.2 is hydrogen or alkyl with a strong base, hydrolyzing and dehydrating the resulting hydroxy-pyrrolinone of the formula ##STR4## wherein R.sup.1, R.sup.2, R.sup.3 and Y have the above significance.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: March 21, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Christopher H. Hill
  • Patent number: 5342964
    Abstract: What is provided herein is a process for obtaining the isomeric compound 1-vinyl-3(E)-ethylidene pyrrolidone in a purity of at least 95%, in the form of white, needle-shaped crystals having a melting point of 59.degree.-61.degree. C.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: August 30, 1994
    Assignee: ISP Investments Inc.
    Inventors: Susan Y. Tseng, Philip F. Wolf
  • Patent number: 5338861
    Abstract: Substituted lactams of the formula ##STR1## can be prepared from lactam N-carboxylates or lactim O-carboxylates of the formulae ##STR2## by thermal or mixed thermal and catalysed CO.sub.2 elimination at 80.degree.-450.degree. C. Lactams substituted on the N atom by aliphatic groups such as those produced herein are useful as industrial aprotic solvents.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: August 16, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Botta, Hans-Josef Buysch, Otto Immel, Lothar Puppe
  • Patent number: 5286876
    Abstract: What is provided herein is a process for obtaining the isomeric compound 1-vinyl-3(E)-ethylidene pyrrolidone in a purity of at least 95%, in the form of white, needle-shaped crystals having a melting point of 59.degree.-61.degree. C.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: February 15, 1994
    Assignee: ISP Investments Inc.
    Inventors: Susan Y. Tseng, Philip F. Wolf
  • Patent number: 5276165
    Abstract: A process for the preparation of N-substituted lactams of the formula I ##STR1## where Z is C.sub.2 - to C.sub.10 -alkylene, C.sub.7 - to C.sub.12 -aralkylene, phenylene or naphthylene, andR.sup.1 is C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 -aryl or C.sub.7 - to C.sub.12 -aralkyl,by hydrogenating a compound of the formula II ##STR2## where W is C.sub.2 - to C.sub.10 -alkylene, C.sub.2 - to C.sub.10 -alkenylene, C.sub.7 - to C.sub.12 -aralkylene, phenylene or naphthylene, andX and Y together form an oxa or imido bridge of the formula ##STR3## or alternatively are identical or different and are hydroxyl, C.sub.1 - to C.sub.20 -alkoxy, C.sub.6 - to C.sub.10 -aryloxy or C.sub.7 - to C.sub.12 -aralkoxy, and, if X and Y are different, Y, in addition to the abovementioned meanings, may also be hydrogen,at superatmospheric pressure and at elevated temperature in the presence of a catalyst and in the presence of an amine, which comprises using a secondary and/or tertiary amine of the formula IIINH.sub.n R.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: January 4, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer
  • Patent number: 5200527
    Abstract: 2-Azabicyclo[2.2.1]hept-5-en-3-one is produced by Diels-Alder reaction of cyclopentadiene and methanesulfonyl cyanide and then hydrolytic cleavage of the methanesulfonyl group.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: April 6, 1993
    Assignee: Lonza Ltd.
    Inventors: Gareth Griffiths, Felix Previdoli
  • Patent number: 5157127
    Abstract: A process for the preparation of N-substituted pyrrolidones by the catalytic hydrogenation of maleic anhydride, maleic acid and/or fumaric acid in the presence of a primary amine and a solvent, at elevated temperature and pressure, wherein a catalyst is used which contains cobalt and at least one of the elements manganese, copper, phosphorus, molybdenum and/or sodium.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: October 20, 1992
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Wolfgang Harder
  • Patent number: 5136051
    Abstract: A process for the preparation of a 2-pyrrolidinone of the general formula I ##STR1## in which R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.20 -alkyl, or C.sub.3 -C.sub.8 -cycloalkyl optionally substituted by C.sub.1 -C.sub.4 -alkyl, or phenyl optionally substituted by C.sub.1 -C.sub.4 -alkyl,by reacting a 3-cyanopropionate of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the meanings stated above and R.sup.3 denotes C.sub.1 -C.sub.8 -alkyl,with hydrogen at elevated temperature and pressure, wherein the reaction is carried out in the presence of ammonia and in contact with a catalyst containing cobalt, manganese, and phosphorus.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: August 4, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Ulrich Koehler
  • Patent number: 5101044
    Abstract: A process for the preparation of N-substituted pyrrolidin-2-ones of the general formula I ##STR1## where R.sup.1 is C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 aryl or C.sub.7 - to C.sub.12 -aralkyl comprises hydrogenolytically cleaving 5-iminopyrrolidin-2-ones of the general formula II ##STR2## in which the R.sup.1 radicals are identical or different C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 -aryl or C.sub.7 - to C.sub.12 -aralkyl, at super-atmospheric pressure and elevated temperature in the presence of a hydrogenation catalyst to give the pyrrolidin-2-ones I; specifically, the 5-iminopyrrolidin-2-ones of the formula II are obtained by reacting .beta.-cyanopropionic acid esters of the general formula III ##STR3## where R.sup.2 is C.sub.1 - to C.sub.20 -alkyl, C.sub.7 - to C.sub.12 -aralkyl or C.sub.6 - to C.sub.10 -aryl, with an amine of the general formula IVR.sup.1 --NH.sub.2 IVwhere R.sup.1 is as defined above.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Ulrich Koehler
  • Patent number: 5101045
    Abstract: A process for the preparation of N-substituted pyrrolidones by catalytic hydrogenation of maleic anhydride, maleic acid and/or fumaric acid in the presence of ammonia uses at least stoichiometric amounts of a primary alcohol or of an aldehyde and uses a catalyst which comprises cobalt and at least one of the elements manganese, copper, phosphorus, molybdenum and/or sodium.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Koehler, Hardo Siegel
  • Patent number: 4956476
    Abstract: The reaction of lactams (preferably N-methyl-2-pyrrolidone) with hydrogen sulfide to thiolactams (preferably N-methyl-2-thiopyrrolidone) is conducted in the presence of a catalyst consisting essentially of alumina.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: September 11, 1990
    Assignee: Phillips Petroleum Company
    Inventors: Alan D. Eastman, Marvin M. Johnson, Richard D. Skinner
  • Patent number: 4873336
    Abstract: The invention relates to the preparation of N-vinyl lactams having the formula ##STR1## wherein n is an integer having an value of from 1 to 3 in a one-stage, non-aqueous process which comprises reacting a lactam having the formula ##STR2## with acetylene under an acetylene partial pressure of from about 25 to about 125 psig. in the presence of an inert gas diluent and a catalyst having the formula ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 are all lower alkyl or alyl or one of R.sub.1, R.sub.2 and R.sub.3 can also be hydrogen and M is a metal selected from the group of cesium, potassium, sodium and lithium.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: October 10, 1989
    Assignee: GAF Corporation
    Inventors: Kou-Chang Liu, Paul D. Taylor
  • Patent number: 4851546
    Abstract: Disclosed is a process for making a 2-pyrrolidone and a succinimide by the vapor phase catalytic reaction of a maleimide with molecular hydrogen.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: July 25, 1989
    Assignee: The Standard Oil Company
    Inventors: Anne M. Graham, Thomas G. Attig
  • Patent number: 4847411
    Abstract: A process for making a diamide of the formula ##STR1## by reacting a monoamide compound of the formula ##STR2## with CO and an amine or ammonia of the formula R.sub.7 R.sub.8 NH in the liquid phase under essentially anhydrous conditions at a temperature in the range from 120.degree. to 210.degree. C., where each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 is selected independently from H and a C.sub.1 to C.sub.12 hydrocarbyl containing no ethylenic or acetylenic unsaturation.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: July 11, 1989
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 4841078
    Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: June 20, 1989
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence Sherman
  • Patent number: 4824967
    Abstract: This invention relates to an improved process for reacting butyrolactone and ammonia which comprises conducting the reaction in the vapor phase in the presence of a magnesium silicate catalyst to selectively produce 2-pyrrolidone in higher yield and purity.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: April 25, 1989
    Assignee: GAF Corporation
    Inventors: Kou-Chang Liu, Paul D. Taylor
  • Patent number: 4814464
    Abstract: An improved process for making N-alkylpyrrolidones from a maleic derivative or a succinic derivative which involves catalytically reducing the maleic derivative with hydrogen to succinic anhydride, if the maleic derivative is the starting point, converting succinic anhydride to a N-alkylsuccinimide by ammonolysis-alkylation with a C.sub.1 and C.sub.4 alkanol and ammonia, and catalytically reducing the resulting N-alkylsuccinimide to the N-alkylpyrrolidone.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: March 21, 1989
    Assignee: Amoco Corporation
    Inventor: Robert J. Olsen
  • Patent number: 4801719
    Abstract: Compounds of the formula Ia ##STR1## in which X and R.sup.1 to R.sup.6 are as defined in the claims, are obtainable by reacting monochlorosilanes of the formula II ##STR2## with tetrasubstituted ethylenes of the formula III ##STR3## X as Cl and Br can be replaced by ester groups of inorganic and organic acids. The compounds of the formula I and those with other ester groups are suitable especially as a protective-group reagent for hydroxyl, mercapto, carboxyl, amino and amide groups.
    Type: Grant
    Filed: June 8, 1987
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Konrad Oertle, Hansjurg Wetter
  • Patent number: 4780547
    Abstract: C.sub.1 -- to C.sub.6 -N-alkylpyrrolidones are produced from succinic anhydride and C.sub.1 -- to C.sub.6 -N-alkylamines or C.sub.1 -- to C.sub.6 --N-alkylsuccinimides. They are hydrogenated in the presence of a Ni hydrogenation catalyst containing from about 0.1-3% of one or several alkaline earth oxides and/or iron oxide and/or chromium oxide, at temperatures of from about 180.degree.-250.degree. C. and under pressures of at least about 100 bar. Preferably, a Ni catalyst is utilized which contains a total of 1.5-2% alkaline earth oxides, iron oxide and chromium oxide.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: October 25, 1988
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred zur Hausen, Werner Otte
  • Patent number: 4731454
    Abstract: A method for producing a lactam having the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, or a straight chain or branched chain alkyl group having from 1 to 5 carbon atoms, and R.sup.2 is an organic group having at least 2 carbon atoms, and connected at both ends to the cyclic acid imide group, which comprises reducing a cyclic acid imide having the formula: ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, or its precursor, with hydrogen by means of a cobalt-based catalyst comprising (a) cobalt and (b) at least one modifier component selected from the group consisting of molybdenum, tungsten and rhenium.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: March 15, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Masayuki Otake, Isamu Fukushima
  • Patent number: 4692523
    Abstract: A process for the preparation of 1-substituted azacycloalkan-2-ones of the formula I ##STR1## in which R, m and n have the meanings indicated by reaction of corresponding 1-trimethylsilylazacycloalkan-2-ones with alkali metal alcoholate or alkali metal oxide and then alkylation of the alkali metal salts which are formed.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: September 8, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Schorr, Wilfried Schmitt
  • Patent number: 4520206
    Abstract: A process for the preparation of maleimide by the vapor phase oxydehydrogenation of succinimide over a heterogeneous catalyst composed of copper, phosphorous, vanadium, molybdenum and oxygen is described.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: May 28, 1985
    Assignee: Ashland Oil, Inc.
    Inventor: Stephen S. Hupp
  • Patent number: 4404391
    Abstract: The invention relates to a process for the preparation of a N-alkyl-2-pyrrolidone by reducing the corresponding N-(.alpha.-hydroxyalkyl)-2-pyrrolidone in the liquid phase under an atmosphere of hydrogen gas and in the presence of a noble metal hydrogenation catalyst while in the absence of trifluoroacetic acid.
    Type: Grant
    Filed: April 1, 1981
    Date of Patent: September 13, 1983
    Assignee: Stamicarbon B.V.
    Inventors: Peter J. N. Meyer, Josef M. Penders