Processes Of Forming 2-pyrrolidone Which Is Unsubstituted Or Alkyl Or Alkenyl Substituted Only Patents (Class 548/552)
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Publication number: 20020128301Abstract: 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 phType: ApplicationFiled: August 10, 2001Publication date: September 12, 2002Inventors: Xiao-Xiong Zhou, Nils-Gunnar Johansson, Horst Wahling, Christian Sund, Lourdes Salvador, Stefan Lindstrom, Hans Wallberg, Christer Sahlberg
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Patent number: 6436243Abstract: 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: GrantFiled: October 18, 2000Date of Patent: August 20, 2002Assignee: Nippon Shokubai Co LTDInventors: Yoshinari Yamaguchi, Hitoshi Yano, Akira Kurusu, Yuuji Shimasaki
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Patent number: 6392104Abstract: 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: GrantFiled: November 10, 1998Date of Patent: May 21, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai
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Patent number: 6348601Abstract: 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: GrantFiled: February 1, 2001Date of Patent: February 19, 2002Assignee: BASF AktiengesellschaftInventors: Frank Ohlbach, Johann-Peter Melder, Karl-Heinz Ross, Martin Rudloff, Jörg Liebe
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Publication number: 20010018528Abstract: 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: ApplicationFiled: February 1, 2001Publication date: August 30, 2001Inventors: Frank Ohlbach, Johann-Peter Melder, Karl-Heinz Ross, Martin Rudloff, Jorg Liebe
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Patent number: 6248902Abstract: 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: GrantFiled: February 4, 2000Date of Patent: June 19, 2001Assignee: Pantochim S. A.Inventor: Aldo Bertola
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Patent number: 6008375Abstract: 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: GrantFiled: March 19, 1999Date of Patent: December 28, 1999Assignee: Akzo Nobel NVInventors: Manfred J. Bergfeld, Kurt Uihlein
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Patent number: 5994562Abstract: 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: GrantFiled: January 14, 1999Date of Patent: November 30, 1999Assignee: BASF AktiengesellschaftInventors: Klaus Ebel, Matthias Eiermann, Thomas Narbeshuber, Eugen Gehrer
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Patent number: 5958821Abstract: 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: GrantFiled: September 24, 1997Date of Patent: September 28, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 5945544Abstract: 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: GrantFiled: August 27, 1998Date of Patent: August 31, 1999Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Hideki Ohmori, Toshiyuki Fukudome, Tomonori Hakozaki, Tomo Oikawa, Satoshi Kakuta, Hidenobu Oda
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Patent number: 5847213Abstract: 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: GrantFiled: March 3, 1997Date of Patent: December 8, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Akira Kurusu, Yuuji Shimasaki
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Patent number: 5700946Abstract: 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: GrantFiled: April 17, 1996Date of Patent: December 23, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Yuuji Shimasaki, Hideyuki Kanbe, Akira Kurusu
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Patent number: 5670639Abstract: 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: GrantFiled: March 13, 1996Date of Patent: September 23, 1997Assignee: BASF AktiengesellschaftInventors: Martin Schmidt-Radde, Marc Heider, Albrecht Dams, Harald Rust
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Patent number: 5665889Abstract: 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: GrantFiled: January 22, 1996Date of Patent: September 9, 1997Assignee: Industrial Technology Research InstituteInventors: Shiao-Jung Chu, Pine-Sci Kuo, Chu-Chang Dai, Hsi-Yen Hsu, Ching-Tang Lin
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Patent number: 5641881Abstract: 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: GrantFiled: August 10, 1995Date of Patent: June 24, 1997Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider
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Patent number: 5625076Abstract: 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: GrantFiled: September 18, 1995Date of Patent: April 29, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Yuuji Shimasaki, Hitoshi Yano, Kimio Ariyoshi
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Patent number: 5571913Abstract: 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: GrantFiled: August 19, 1994Date of Patent: November 5, 1996Assignee: DSM N.V.Inventor: Petrus J. H. Thomissen
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Patent number: 5569770Abstract: 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: GrantFiled: January 31, 1996Date of Patent: October 29, 1996Assignee: Industrial Technology Research InstituteInventors: Pine-Sci Kuo, Shiao-Jung Chu, Chu-Chang Dai, Hsi-Yen Hsu, Ching-Tang Lin, Yi-Yun Lin
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Patent number: 5539102Abstract: 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: GrantFiled: February 18, 1993Date of Patent: July 23, 1996Assignee: Shionogi Seiyaku Kabushiki KaishaInventors: Yuji Sendo, Makoto Kii, Yasuhiro Nishitani, Tadashi Irie, Yutaka Nishino
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Patent number: 5508396Abstract: 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: GrantFiled: April 13, 1995Date of Patent: April 16, 1996Assignee: Huels AktiengesellschaftInventor: Klaus-Dieter Steffen
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Patent number: 5496958Abstract: 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: GrantFiled: June 27, 1994Date of Patent: March 5, 1996Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Werner Hoffmann, Ernst Langguth, Hardo Siegel
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Patent number: 5478950Abstract: 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: GrantFiled: August 8, 1994Date of Patent: December 26, 1995Assignee: Akzo Nobel N.V.Inventors: Manfred Bergfeld, Gunter Wiesgickl
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Patent number: 5434273Abstract: 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: GrantFiled: February 4, 1994Date of Patent: July 18, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer
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Patent number: 5410070Abstract: 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: GrantFiled: January 27, 1994Date of Patent: April 25, 1995Assignee: BASF AktiengesellschaftInventors: Lothar Franz, Michael Huellmann
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Patent number: 5401856Abstract: 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: GrantFiled: February 28, 1994Date of Patent: March 28, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Roger A. Grey, Diandre Armstead
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Patent number: 5399712Abstract: 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: GrantFiled: November 4, 1992Date of Patent: March 21, 1995Assignee: Hoffmann-La Roche Inc.Inventor: Christopher H. Hill
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Patent number: 5342964Abstract: 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: GrantFiled: March 31, 1993Date of Patent: August 30, 1994Assignee: ISP Investments Inc.Inventors: Susan Y. Tseng, Philip F. Wolf
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Patent number: 5338861Abstract: 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: GrantFiled: July 24, 1992Date of Patent: August 16, 1994Assignee: Bayer AktiengesellschaftInventors: Artur Botta, Hans-Josef Buysch, Otto Immel, Lothar Puppe
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Patent number: 5286876Abstract: 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: GrantFiled: March 31, 1993Date of Patent: February 15, 1994Assignee: ISP Investments Inc.Inventors: Susan Y. Tseng, Philip F. Wolf
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Patent number: 5276165Abstract: 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: GrantFiled: November 25, 1992Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer
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Patent number: 5200527Abstract: 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: GrantFiled: April 1, 1992Date of Patent: April 6, 1993Assignee: Lonza Ltd.Inventors: Gareth Griffiths, Felix Previdoli
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Patent number: 5157127Abstract: 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: GrantFiled: June 4, 1991Date of Patent: October 20, 1992Inventors: Hans-Juergen Weyer, Rolf Fischer, Wolfgang Harder
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Patent number: 5136051Abstract: 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: GrantFiled: October 8, 1991Date of Patent: August 4, 1992Assignee: BASF AktiengesellschaftInventors: Ludwig Schuster, Ulrich Koehler
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Patent number: 5101044Abstract: 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: GrantFiled: September 4, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Ludwig Schuster, Ulrich Koehler
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Patent number: 5101045Abstract: 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: GrantFiled: June 4, 1991Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich Koehler, Hardo Siegel
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Patent number: 4956476Abstract: 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: GrantFiled: March 1, 1990Date of Patent: September 11, 1990Assignee: Phillips Petroleum CompanyInventors: Alan D. Eastman, Marvin M. Johnson, Richard D. Skinner
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Patent number: 4873336Abstract: 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: GrantFiled: March 28, 1988Date of Patent: October 10, 1989Assignee: GAF CorporationInventors: Kou-Chang Liu, Paul D. Taylor
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Patent number: 4851546Abstract: 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: GrantFiled: October 28, 1988Date of Patent: July 25, 1989Assignee: The Standard Oil CompanyInventors: Anne M. Graham, Thomas G. Attig
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Patent number: 4847411Abstract: 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: GrantFiled: May 3, 1985Date of Patent: July 11, 1989Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4841078Abstract: 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: GrantFiled: August 9, 1984Date of Patent: June 20, 1989Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence Sherman
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Patent number: 4824967Abstract: 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: GrantFiled: June 27, 1988Date of Patent: April 25, 1989Assignee: GAF CorporationInventors: Kou-Chang Liu, Paul D. Taylor
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Patent number: 4814464Abstract: 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: GrantFiled: March 30, 1987Date of Patent: March 21, 1989Assignee: Amoco CorporationInventor: Robert J. Olsen
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Patent number: 4801719Abstract: 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: GrantFiled: June 8, 1987Date of Patent: January 31, 1989Assignee: Ciba-Geigy CorporationInventors: Konrad Oertle, Hansjurg Wetter
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Patent number: 4780547Abstract: 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: GrantFiled: July 6, 1987Date of Patent: October 25, 1988Assignee: Huels AktiengesellschaftInventors: Manfred zur Hausen, Werner Otte
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Patent number: 4731454Abstract: 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: GrantFiled: May 29, 1987Date of Patent: March 15, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Masayuki Otake, Isamu Fukushima
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Patent number: 4692523Abstract: 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: GrantFiled: October 7, 1986Date of Patent: September 8, 1987Assignee: Hoechst AktiengesellschaftInventors: Manfred Schorr, Wilfried Schmitt
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Patent number: 4520206Abstract: 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: GrantFiled: February 27, 1984Date of Patent: May 28, 1985Assignee: Ashland Oil, Inc.Inventor: Stephen S. Hupp
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Patent number: 4404391Abstract: 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: GrantFiled: April 1, 1981Date of Patent: September 13, 1983Assignee: Stamicarbon B.V.Inventors: Peter J. N. Meyer, Josef M. Penders