Processes For Preparation Of Saturated Nitriles Patents (Class 558/467)
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Patent number: 9272275Abstract: Selective, radically initiated oxidative decarboxylation may produce low viscosity renewable fuels from biologically derived fats and oils. Fatty acids and triglycerides may be decarboxylated using oxidants at a water/oil interface. The oxidants may be produced using photo-Fenton reagents. The reaction advantageously can be carried out at room temperature and pressure and has fewer unwanted byproducts than traditional decarboxylation techniques.Type: GrantFiled: October 25, 2010Date of Patent: March 1, 2016Assignee: University of Vermont and State Agricultural CollegeInventors: Bryan J. Holmes, Alexander Wurthmann
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Publication number: 20150057450Abstract: The present invention provides novel Ruthenium-based transition metal complex catalysts comprising specific ligands, their preparation and their use in hydrogenation processes. Such complex catalysts are inexpensive, thermally robust, and olefin selective.Type: ApplicationFiled: August 15, 2012Publication date: February 26, 2015Applicants: LANXESS DEUTSCHLAND GMBH, THE GOVERNING COUNCIL OF UNIVERSITY OF TORONTOInventors: Julia Maria Jeschko, Douglas Stephan, Clinton Lund, Michael Sgro, Christopher Ong, Renan Cariou
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Patent number: 8222445Abstract: The present invention relates to an industrially usable process for preparing alkali metal and alkaline earth metal tricyanomethanides in particularly high purity.Type: GrantFiled: August 15, 2008Date of Patent: July 17, 2012Assignee: Lonza LtdInventors: Harald Strittmatter, Stefan Koger
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Patent number: 8022242Abstract: The present invention relates to a process for preparing highly pure alkali metal or alkaline earth metal tricyanomethanides.Type: GrantFiled: August 16, 2007Date of Patent: September 20, 2011Assignee: Lonza AGInventors: Christoph Täschler, Andreas Breuer
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Publication number: 20110060155Abstract: The present invention relates to an industrially usable process for preparing alkali metal and alkaline earth metal tricyanomethanides in particularly high purity.Type: ApplicationFiled: August 15, 2008Publication date: March 10, 2011Inventors: Harald Strittmatter, Stefan Koger
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Patent number: 7795466Abstract: The present invention relates to a process for the preparation of saturated nitrites by catalytic hydrogenation of the corresponding olefinically unsaturated compounds in the presence of a supported transition metal catalyst at a pressure of from 1 to 95 bar. Specifically, the invention relates to a process for the preparation of tetrahydrogeranonitrile (3,7-dimethyloctanenitrile) by catalytic hydrogenation of geranonitrile.Type: GrantFiled: April 7, 2006Date of Patent: September 14, 2010Assignee: BASF AktiengesellschaftInventors: Jan Kurt Eberhardt, Wolfgang Krause
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Publication number: 20080227998Abstract: A process is described for preparing 3-pentenenitrile, characterized by the following process steps: (a) reacting 1,3-butadiene with hydrogen cyanide over at least one catalyst to obtain a stream 1 which comprises 3-pentenenitrile, 2-methyl-3-butenenitrile, the at least one catalyst and 1,3-butadiene, (b) distilling stream 1 in a column to obtain a high-1,3-butadiene stream 2 as the top product and a low-1,3-butadiene stream 3 as the bottom product which comprises 3-pentenenitrile, the at least one catalyst and 2-methyl-3-butenenitrile, (c) distilling stream 3 in a column to obtain a stream 4 as the top product which comprises 1,3-butadiene, a stream 5 which comprises 3-pentenenitrile and 2-methyl-3-butenenitrile at a side draw of the column, and a stream 6 as the bottom product which comprises the at least one catalyst, (d) distilling stream 5 to obtain a stream 7 as the top product which comprises 2-methyl-3-butenenitrile, and a stream 8 as the bottom product which comprises 3-pentenenitrile.Type: ApplicationFiled: January 27, 2005Publication date: September 18, 2008Applicant: BASF AktiengesellschaftInventors: Jens Scheidel, Tim Jungkamp, Michael Bartsch, Gerd Haderlein, Robert Baumann, Hermann Luyken
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Patent number: 7405318Abstract: The invention relates to a method for producing the nitrites of formula: R1—CN by reacting aldehyde oximes (R1CN?N—OH) with cyclic alkylphosphonic anhydrides at a temperature ranging from ?100 to +120° C., wherein R1 represents H, a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl, alkenyl or an aryl or heteroaryl group. The cyclic phosphonic anhydride preferably used is a 2,4,6-substituted 1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide of formula (I), wherein R? independently represents allyl, aryl or open-chain or branched C1 to C12 alkyl groups.Type: GrantFiled: June 4, 2005Date of Patent: July 29, 2008Assignee: Archimica GmbHInventors: Andreas Meudt, Stefan Scherer, Claudius Boehm
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Publication number: 20080177100Abstract: The present invention relates to a process for the preparation of saturated nitrites by catalytic hydrogenation of the corresponding olefinically unsaturated compounds in the presence of a supported transition metal catalyst at a pressure of from 1 to 95 bar. Specifically, the invention relates to a process for the preparation of tetrahydrogeranonitrile (3,7-dimethyloctanenitrile) by catalytic hydrogenation of geranonitrile.Type: ApplicationFiled: April 7, 2006Publication date: July 24, 2008Applicant: BASF AktiengeellschaftInventors: Jan Eberhardt, Wolfgang Krause
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Publication number: 20080154056Abstract: An improved process for the production of unsaturated carboxylic acids and unsaturated nitriles from their corresponding C3 to C5 alkanes, or mixtures of C3 to C5 alkanes and alkenes, that involves oxidation in the presence of a supported Mo-V-based mixed metal oxide catalyst in a multi-stage reaction system which employs both separation of the oxidation product from one or more intermediate effluent streams, as well as feeding additional oxygen to reaction zones subsequent to the first reaction zone.Type: ApplicationFiled: November 16, 2007Publication date: June 26, 2008Inventors: Anne Mae Gaffney, Scott Han
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Publication number: 20080139838Abstract: The invention relates to a method for producing bifunctional ammonium nitriles of the following general formulae: by reacting a tertiary diamine with a cyanomethylene-group-transferring quaternizing agent in a polar, aprotic solvent. Bifunctional ammonium nitriles may be used as bleach activators in detergents and cleaners.Type: ApplicationFiled: February 24, 2006Publication date: June 12, 2008Inventors: Gerd Reinhardt, Hans Prehler, Lars Cuypers
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Patent number: 7371890Abstract: A process for continuously preparing a compound which bears at least two functional groups which are each independently selected from the group consisting of nitrile group, carboxylic acid group, carboxylic ester group and carboxamide group.Type: GrantFiled: June 11, 2004Date of Patent: May 13, 2008Assignee: BASF AktiengesellschaftInventors: Wolfram Stüer, Jens Scheidel, Hartwig Voβ, Peter Baβler, Michael Röper
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Patent number: 6329549Abstract: A process for methylating an alpha carbon adjacent to an electron withdrawing group includes reacting dimethyl ether with a molecule containing the alpha carbon and the electron withdrawing group to substitute a methyl group on the alpha carbon. The process can be conducted in a vapor phase and can be represented by Equation I: R(CH2)nCH2-EWG+CH3OCH3→R(CH2)nCH(CH3)-EWG+CH3OH (I) where EWG is the electron withdrawing group, and R is H when n is 0, 1 or 2, and R is alkyl, EWG or aryl when n>2. For example, the molecule reacted with dimethyl ether can be acetic acid, propionic acid, methyl acetate, methyl propionate, acetonitrile, propionitrile and acetone. The process is catalyzed by an acid catalyst containing a Lewis acid functionality. When the electron withdrawing group is an acid, a methyl ester can be formed by esterifying the electron withdrawing group with methanol liberated from dimethyl ether.Type: GrantFiled: April 6, 2000Date of Patent: December 11, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Francis Joseph Waller, Gene Everad Parris
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Patent number: 5773637Abstract: A process is disclosed for preparing a perfluoroalkyl sulfonate of the formula R.sub.a MX.sub.b-c O.sub.g ?(SO.sub.3).sub.d (R.sub.f).sub.e !.sub.c. This process involves reacting a reagent of the fonnula R.sub.a MX.sub.b O.sub.g and a second reagent of the formula R'.sub.x E?(SO.sub.3).sub.d (R.sub.f).sub.e !.sub.y,whereR is selected from the group consisting of C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 perfluoroalkyl, cyclopentadienyl (i.e., C.sub.5 H.sub.5), phenyl and perfluorophenyl;M is selected from the group consisting of transistion metals of groups 3 to 12, main group elements of group 13 to 16 and lanthanide metals;X is selected from the group consisting of F, Cl and Br;R.sub.f is selected from the group consisting of C.sub.h F.sub.2h+1, C.sub.h F.sub.2h, wherein h is an integer from 0 to 10, perfluorophenyl, C.sub.6 F.sub.4 (CF.sub.2).sub.2 i, wherein i is an integer from 0 to 6, provided that when E is boron, R.sub.f is selected from the group consisting of C.sub.h' F.sub.Type: GrantFiled: September 6, 1996Date of Patent: June 30, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Walter Vladimir Cicha, Andreas Josef Kornath, Ronald James McKinney, V. N. Mallikarjuna Rao, Joseph Stuart Thrasher, Alfred Waterfeld
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Patent number: 5268509Abstract: This invention relates to a process for the preparation of an iron catalyst used for the hydrogenation of organic compounds comprising partially oxidizing iron or an iron alloy in particulate form at an elevated temperature in the presence of gaseous oxygen until a weight gain of from 5% to 32% is obtained; and then reducing the partially oxidized iron or iron alloy at an elevated temperature in a stream of hydrogen.The invention also relates to a process for the preparation of primary amines comprising catalytically hydrogenating nitriles corresponding to said primary amines in the presence of an iron catalyst of the invention.Type: GrantFiled: June 11, 1990Date of Patent: December 7, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
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Patent number: 5237088Abstract: A process for transfer hydrogenation of nitriles and amines wherein the amines are the hydrogen donors is disclosed.Type: GrantFiled: March 25, 1992Date of Patent: August 17, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 5196589Abstract: The present invention relates to novel methods of stabilizing polymers of acrylonitrile. The polymers are stabilized by the inclusion of small amounts of stable free radicals compounds which act to inhibit the homopolymerization of the acrylonitrile while promoting the reaction of the acrylonitrile with nucleophilic species such as amines and alcohols.Type: GrantFiled: September 16, 1991Date of Patent: March 23, 1993Assignee: LCE PartnershipInventors: Anthony J. O'Lenick, Jr., J. Michael Clumpner
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Patent number: 5049693Abstract: The hydrogenation of olefins containing nitrile groups in the homogeneous phase can be carried out particularly successfully using specific ruthenium complexes which are non-sensitive to air and have high catalytic activity.Type: GrantFiled: June 18, 1990Date of Patent: September 17, 1991Assignee: Bayer AktiengesellschaftInventor: Thomas Himmler
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Patent number: 4978771Abstract: The selective hydrogenation of unsaturated compounds which carry reducible groups containing nitrogen succeeds in a homogeneous phase with the preservation of the reducible groups containing nitrogen, characterized in that a compound of the formulaRuH.sub.2n L.sub.5-nis used as a catalyst, in whichL signifies a phosphane or arsane andn signifies 1 or 2.Type: GrantFiled: May 18, 1988Date of Patent: December 18, 1990Assignee: Bayer AktiengesellschaftInventors: Paul Fiedler, Hartmuth Buding, Rudolf Braden
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Patent number: 4683088Abstract: The invention provides a nickel/alumina/silicate catalyst, with an atomic ratio of nickel/aluminium between 20 and 2, a nickel/silicate ratio between 20 and 1, an active nickel surface area between 70 and 150 m.sup.2 /g nickel and an average pore size, depending on the above atomic ratio, between 4 and 20 nanometers. Preferably the nickel/aluminium atomic ratio is between 10 and 4 and the nickel/silicate ratio between 12 and 3. Preferably the catalyst has a specific porous structure.The invention also provides a method for preparing the catalyst by a two step process involving precipitating nickel ions and adding during a second, so-called ageing step a soluble aluminium compound and optionally the silicate. The silicate is preferably added during a second ageing step.The catalyst is useful for hydrogenating unsaturated organic compounds in particular oils.Type: GrantFiled: September 17, 1986Date of Patent: July 28, 1987Assignee: Internationale Octrooi Maatschappij "Octropa" BVInventors: Johannes C. Oudejans, Peter Nootenboom, Keshab L. Ganguli, Cornelis M. Lok
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Patent number: 4673757Abstract: Carbon-carbon double bonds are hydrogenated selectively in a compound containing a reducible, nitrogen-containing group if the hydrogenation is carried out in the presence of a ruthenium complex catalyst. Also disclosed are new ruthenium complexes for use in such selective hydrogenation.Type: GrantFiled: October 11, 1984Date of Patent: June 16, 1987Assignee: Bayer AktiengesellschaftInventors: Paul Fiedler, Rudolf Braden, Hartmuth Buding
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Patent number: 4609635Abstract: Regeneration of an ammoxidation catalyst which is exhausted as a result of prolonged exposure to ammoxidation conditions, containing oxides of Mo, Bi, P, Fe, Co, Ni and possibly an alkali metal, particularly K, on a granular support, particularly silica, by means of a method including:the impregnation of the granules of spent catalyst with an aqueous molybdic acid solution, or with an aqueous solution of partially or totally salified molybdic acid in the form of the ammonium salt, with a volume of impregnation solution less than the total pore volume of the catalyst subjected to regeneration;the drying of the impregnated granules at a temperature of from 100.degree. to 200.degree. C.;the calcining of the dried granules at a temperature of from 250.degree. to 450.degree. C., solely when the impregnation is with an aqueous solution of partially or totally salified molybdic acid.Type: GrantFiled: April 17, 1985Date of Patent: September 2, 1986Assignee: Enichem Sintesi S.p.A.Inventors: Roberto Canavesi, Ferdinando Ligorati, Roberto Ghezzi
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Patent number: 4575434Abstract: A process for the removal of impurities comprising amides from a solution comprising nitriles and the impurities. A reaction mixture is formed which includes the solution, a layered mineral comprising aluminum silicates having exchangeable alkaline or alkaline earth cations on the surfaces of the layers and an acid which has an acid strength sufficient to protonate the amides at amide protonation conditions, but in which the solubility of the salt of the acid and exchangeable cation at those conditions is such that the equilibrium of the protonation reaction is substantially in the direction of the amides remaining in a protonated form. The water content of the reaction mixture must be less than about 0.5 wt. % for substantially all of the reaction time. The reaction mixture is maintained for a sufficient time at the amide protonation conditions for protonation of the amides and exchange of the protonated amides and exchangeable cations to occur, the protonated amides adhering to the surfaces of the layers.Type: GrantFiled: September 28, 1984Date of Patent: March 11, 1986Assignee: Akzona IncorporatedInventors: Dieter Frank, Lincoln D. Metcalfe, John Y. G. Park
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Patent number: RE34548Abstract: The selective hydrogenation of unsaturated compounds which carry reducible groups containing nitrogen succeeds in a homogeneous phase with the preservation of the reducible groups containing nitrogen, characterized in that a compound of the formulaRuH.sub.2n L.sub.5-nis used as a catalyst, in whichL signifies a phosphane or arsane andn signifies 1 or 2.Type: GrantFiled: July 29, 1992Date of Patent: February 15, 1994Assignee: Bayer AktiengesellschaftInventors: Paul Fiedler, Hartmuth Buding, Rudolf Braden