Preparing Directly From Carbon Monoxide Or Carbon Dioxide Patents (Class 564/132)
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Patent number: 12037746Abstract: A method for manufacturing a compound comprising at least one imine group, the method comprising a step of reaction between a first compound comprising at least one amine group and a second compound comprising at least one carbonyl group, the reaction step being carried out in the presence of at least one supercritical fluid.Type: GrantFiled: October 20, 2020Date of Patent: July 16, 2024Assignee: COMMISSARIAT À L'ÉNERGIE ATOMIQUE ET AUX ÉNERGIES ALTERNATIVESInventors: Olivier Poncelet, Aurélien Auger
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Publication number: 20150105571Abstract: The invention relates to a method for converting carbon dioxide or bicarbonates into formic acid derivatives, i.e. formate salts, formate esters, and formamides, using molecular hydrogen and a catalytic system comprising a cobalt complex of cobalt salt and at least one tripodal, tetradentate ligand. The catalyst complex can be used as a homogeneous catalyst. The invention further relates to the cobalt complexes per se.Type: ApplicationFiled: November 26, 2012Publication date: April 16, 2015Inventors: Ralf Jackstell, Carolin Ziebart, Christopher Federsel, Matthias Beller
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Patent number: 8877971Abstract: The present invention relates to a method for preparing formamide compounds using carbon dioxide, and to the use of said method for manufacturing vitamins, pharmaceutical products, adhesives, acrylic fibers, synthetic leathers, pesticides and fertilizers. The invention also relates to a method for manufacturing vitamins, pharmaceutical products, adhesives, acrylic fibers, synthetic leathers, pesticides and fertilizers which includes a step of preparing formamide compounds by the method according to the invention.Type: GrantFiled: April 4, 2012Date of Patent: November 4, 2014Assignee: Commissariat a l'Energie Atomique et aux Energies AlternativesInventors: Thibault Cantat, Christophe Gomes, Olivier Jacquet
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Patent number: 8829226Abstract: A new compound is provided, which is used for preparing lacosamide. A novel method for preparing lacosamide is also provided. During the reaction, iodomethane and silver oxide that are cost expensive are not used, nor a Pd-c catalyst is used, so the production cost is low, the raw materials and accessory materials are cheap and easily available, and the process is simple, so that industrial production is easy to realize; and moreover, the yield is high, and good economic efficiency can be achieved.Type: GrantFiled: January 28, 2011Date of Patent: September 9, 2014Assignee: Zhejiang Jiuzhou Pharmaceutical Co., LtdInventors: Xianyi Zhang, Shaoqing Ge, Daqing Che
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Publication number: 20140018576Abstract: The present invention relates to a method for preparing formamide compounds using carbon dioxide, and to the use of said method for manufacturing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides and fertilisers. The invention also relates to a method for manufacturing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides and fertilisers which includes a step of preparing formamide compounds by the method according to the invention.Type: ApplicationFiled: April 4, 2012Publication date: January 16, 2014Applicant: Commissariat A L'Energie Atomique Et Aux Energies AlternativesInventors: Thibault Cantat, Christophe Gomes, Olivier Jacquet
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Patent number: 8513463Abstract: A process is described for the production of one or more of linear nitriles, amides and formamides which includes reacting a nitrogen containing compound, such as ammonia or NOx, and a synthesis gas over a catalyst at a temperature of between 160° C. and 400° C. and a pressure of between 1 bar and 50 bar. A further process for the production of one or more of linear phosphorous containing compounds is also described, which includes reacting a phosphorous containing compound, such as a phosphine, and a synthesis gas over a catalyst at a temperature of between 160° C. and 400° C. and a pressure of between 1 bar and 50 bar. A supported cobalt, iron, ruthenium or rhodium catalyst or an unsupported (bulk) promoted iron catalyst, modified with a promoter is used. The synthesis gas is a mixture of hydrogen and carbon monoxide, in a ratio from 0.5:1 to 5:1; or a mixture of hydrogen and carbon dioxide; or a mixture of water and carbon monoxide.Type: GrantFiled: April 15, 2009Date of Patent: August 20, 2013Assignees: The University of Cape Town, Carl Von Ossietzky Universitat OldenburgInventors: Michael Christian Maximilian Claeys, Eric Wilhelmus Josephus Van Steen, Frank Roessner, Tawanda Stephen Sango
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Publication number: 20130102807Abstract: A process for preparing carboxylic acid derivatives of the formula H—(C?O)—R, R is OR1 or NR2R3, R1 is optionally substituted C1-C15-alkyl, C5-C10-cycloalkyl, C5-C10-heterocyclyl, C5-C10-aryl or C5-C10-heteroaryl, substituents are C1-C15-alkyl, C1-C6-alkoxy, C5-C10-cycloalkyl or C5-C10-aryl; R2 and R3 are independently hydrogen or optionally substituted C1-C15-alkyl, C5-C10 cycloalkyl, C5-C10-heterocyclyl, C5-C10-aryl or C5-C10-heteroaryl, substituents are selected from the group consisting of C1-C15-alkyl, C5-C10-cycloalkyl and C5-C10-aryl or R2 and R3 together with the nitrogen atom form a five- or six-membered ring which optionally comprises one or more heteroatoms selected from O, S and N and bearing the substituent R4, R4 is hydrogen or C1-C6-alkyl; by reacting a reaction mixture comprising carbon dioxide, hydrogen and an alcohol of the formula R1—OH or an amine of the formula NHR2R3 in the presence of a catalyst comprising gold at a pressure from 0.2 to 30 MPa and a temperature from 20 to 200° C.Type: ApplicationFiled: July 26, 2012Publication date: April 25, 2013Applicant: BASF SEInventors: Thomas Schaub, Rocco Paciello, Marek Pazicky, Giuseppe Fachinetti, Debora Preti
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Publication number: 20130066102Abstract: A new compound is provided, which is used for preparing lacosamide. A novel method for preparing lacosamide is also provided. During the reaction, iodomethane and silver oxide that are cost expensive are not used, nor a Pd-c catalyst is used, so the production cost is low, the raw materials and accessory materials are cheap and easily available, and the process is simple, so that industrial production is easy to realize; and moreover, the yield is high, and good economic efficiency can be achieved.Type: ApplicationFiled: January 28, 2011Publication date: March 14, 2013Applicant: ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTDInventors: Xianyi Zhang, Shaoqing Ge, Daqing Che
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Publication number: 20120071690Abstract: A process is proposed for production of formamides by reaction of carbon dioxide with hydrogen in a hydrogenation reactor I in the presence of a catalyst comprising an element from group 8, 9 or 10 of the periodic table, a tertiary amine comprising at least 6 carbon atoms per molecule, and also a polar solvent, to form formic acid-amine adducts as intermediates, which are subsequently reacted with ammonia or amines in a reactor to obtain a two-phase liquid reaction effluent from which the liquid phase enriched with the formamides is distillatively separated to recover the formamide.Type: ApplicationFiled: September 16, 2011Publication date: March 22, 2012Applicant: BASF SEInventors: Marek Pazicky, Thomas Schaub, Ansgar Gereon Altenhoff, Donata Maria Fries, Rocco Paciello
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Publication number: 20110172456Abstract: Process for the preparation of aromatic and heteroaromatic carboxylic acids, carboxylic acid esters and carboxamides by the reaction of aromatic or heteroaromatic halides R—Xn, in which n=integer from 1 to 6, R=substituted or unsubstituted and aromatic or heteroaromatic radical and X=chlorine, bromine or iodine atom, with carbon monoxide and water, ammonia, alcohols or amines in the presence of bases and zero-valent or divalent palladium compounds and bidentate diphosphanes or complexes of zero-valent or divalent palladium with bidentate diphosphanes, in which use is made of bidentate diphosphanes (R1—)(R2—)P—Y—P(—R3)(—R4) in which R1 to R4=unsubstituted aryl radicals or aryl radicals substituted with at least one radical exhibiting a positive resonance effect or a positive inductive effect, or unsubstituted or substituted cycloalkyl radicals, and Y=hydrocarbon group with a total of 2 to 20 carbon atoms, in which at least one of the carbon atoms carries only one or no hydrogen atom as substituent; except fType: ApplicationFiled: May 25, 2009Publication date: July 14, 2011Applicant: BASF SEInventors: Nina Challand, Ansgar Gereon Altenhoff, Joachim Schmidt-Leithoff, Kathrin Wissel-Stoll, Michael Rack, Joachim Rheinheimer
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Patent number: 7960585Abstract: The present invention relates to a process for preparing secondary amides with good selectivity by carbonylating a corresponding tertiary amine with carbon monoxide in a reaction mixture in the presence of a metal catalyst and in the presence of a halogen containing promoter. The metal catalyst comprises palladium. A same or even a much better catalytic activity can be obtained with palladium than with the much more expensive rhodium, especially when the palladium is used in a low concentration. Moreover, also a good selectivity can be achieved.Type: GrantFiled: April 1, 2009Date of Patent: June 14, 2011Assignee: TamincoInventors: Mondher Srasra, Pierre Jacobs, Bert Sels, Maria Christina Jacoba Tielen, Kristof Moonen, Peter Roose, Ivan Vanden Eynde
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Publication number: 20110092728Abstract: A process is described for the production of one or more of linear nitriles, amides and formamides which includes reacting a nitrogen containing compound, such as ammonia or NOx, and a synthesis gas over a catalyst at a temperature of between 160° C. and 400° C. and a pressure of between 1 bar and 50 bar. A further process for the production of one or more of linear phosphorous containing compounds is also described, which includes reacting a phosphorous containing compound, such as a phosphine, and a synthesis gas over a catalyst at a temperature of between 160° C. and 400° C. and a pressure of between 1 bar and 50 bar. A supported cobalt, iron, ruthenium or rhodium catalyst or an unsupported (bulk) promoted iron catalyst, modified with a promoter is used. The synthesis gas is a mixture of hydrogen and carbon monoxide, in a ratio from 0.5:1 to 5:1; or a mixture of hydrogen and carbon dioxide; or a mixture of water and carbon monoxide.Type: ApplicationFiled: April 15, 2009Publication date: April 21, 2011Applicants: THE UNIVERSITY OF CAPE TOWN, CARL VON OSSIETZKY UNIVERSITAT OLDENBURGInventors: Michael Christian Maximilian Claeys, Eric Wilhelmus Josephus Van Steen, Frank Roessner, Tawanda Stephen Sango
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Publication number: 20090247744Abstract: The invention relates to an improved process for the preparation of an advanced synthetic intermediate of ACE inhibitors. In one aspect, the present invention is based on a novel process for the preparation of an aldehyde of formula (I), wherein (N)PrG is a protected amino group, R is an alkyl or aralkyl group and X1-4 are each independently H or a non-reacting substituent, which comprises hydroformylation of an ?-olefin of formula (II), by reaction with syngas (CO/H2) in the presence of, as catalyst, a group VII transition metal complex of a phosphorus-containing ligand. Aldehyde (I), the product of linear hydroformylation, is formed in preference to aldehyde (III). In another aspect of the invention, ?-olefin (II) is a novel composition. The process to convert (II) to (I) enables an efficient manufacturing route to MDL 28,726 and analogues.Type: ApplicationFiled: June 10, 2009Publication date: October 1, 2009Inventors: Edward D Daugs, Wei-Jun Peng, Cynthia L Rand
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Patent number: 6642420Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in theType: GrantFiled: February 7, 2001Date of Patent: November 4, 2003Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Armin Ulonska, Rocco Paciello
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Patent number: 6441234Abstract: In the process for preparing formamide by reaction of ammonia and carbon monoxide in the presence of at least one catalyst, sodium diformylamide is used as catalyst. If sodium methoxide is used as further active component, sodium diformylamide can be formed from this. In this process, sodium diformylamide is a particularly active and stable catalyst which can be recycled.Type: GrantFiled: July 17, 2001Date of Patent: August 27, 2002Assignee: Abbott LaboratoriesInventors: Jürgen Dahlhaus, Jörn Karl, Michael Schulz, Anne Wenzel, Wolfgang Harder, Arthur Höhn
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Patent number: 6441233Abstract: A process for the preparation of primary aromatic carboxamides by the carbonylation of an aromatic compound, which contains at least one leaving group, with carbon monoxide, in the presence of a homogeneous or heterogeneous Pd catalyst and at least stoichiometric amounts of an amidation agent at elevated temperatures, which is characterized in that a primary carboxamide or a primary urethane is used as the amidation agent, and the reaction is carried out in the presence of an acylation catalyst.Type: GrantFiled: June 21, 2001Date of Patent: August 27, 2002Assignee: Solvias AGInventors: Anita Schnyder, Adriano Indolese, Gerald Mehltretter
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Patent number: 6388085Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the characteristic optical and other properties of polyacetylenes.Type: GrantFiled: August 23, 2000Date of Patent: May 14, 2002Assignee: Board of Trustees of Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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Patent number: 6326517Abstract: A method of producing benzamides represented by the following general formula (1): where R is trifluoromethyl group, trifluoromethyloxy group, halogen (fluorine, chlorine, bromine or iodine), nitro group, acetyl group, cyano group, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or a alkoxycarbonyl group having 2 to 5 carbon atoms; and n is 0 or an integer ranging from 1 to 3.Type: GrantFiled: December 10, 1999Date of Patent: December 4, 2001Assignee: Central Glass Company, LimitedInventors: Takashi Kume, Michio Ishida, Satoru Narizuka, Yuzuru Morino, Makoto Koide
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Patent number: 5919979Abstract: This invention relates to an improvement in a process for the production of an alkyl formamide, wherein a gas-containing carbon monoxide is reacted at elevated temperature and pressure in reaction zone with a nitrogen-containing compound selected from the group consisting of ammonia, a primary or secondary alkylamine, in the presence of a solvent and a catalyst. The improvement comprises utilizing a solvent comprising a polyethylene glycol, polypropylene glycol, polyethylenepropylene glycol, or mixtures, and an alkali metal or alkaline earth metal alkoxide of a polyethylene glycol, polypropylene glycol, polyethylenepropylene glycol or mixtures as the catalyst.Type: GrantFiled: September 28, 1993Date of Patent: July 6, 1999Assignee: Air Products and Chemicals, Inc.Inventors: John William Mitchell, Thomas Albert Johnson
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Patent number: 5763662Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.Type: GrantFiled: November 20, 1996Date of Patent: June 9, 1998Assignees: Research Development Corporation of Japan, NKK CorporationInventors: Takao Ikariya, Philip Gregory Jessop, Yi Hsiao, Ryoji Noyori
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Patent number: 5672750Abstract: The present invention is directed to a process for preparing an aromatic amide. More specifically, the process involves reacting carbon monoxide, an amine and an aromatic chloride in the presence of an iodide or bromide salt, a catalyst, and a base.Type: GrantFiled: May 31, 1996Date of Patent: September 30, 1997Assignee: Eastman Chemical CompanyInventor: Robert James Perry
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Patent number: 5436356Abstract: A process for the carbonylation of ethylenically unsaturated compounds by reaction with carbon monoxide and a co-reactant in the presence of a substantially non-acidic catalyst system based on a palladium compound and a bidentate ligand of the formulaR.sub.1 R.sub.2 M.sub.1 RM.sub.2 R.sub.3 R.sub.4in which M.sub.1 and M.sub.2 may be phosphorus, arsenic or antimony atom, R is a bivalent organic bridging group, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently substituted or non-substituted aliphatic groups, with the proviso that R.sub.1 together with R.sub.2, and/or R.sub.3 together with R.sub.4 form a bivalent cyclic group with at least 5 ring atoms whereby the two free valencies are linked to M.sub.1 or M.sub.2, respectively.Catalytic compositions employing the bidentate ligands used in this method in which M.sub.1 and M.sub.2 are phosphorous are also presented.Type: GrantFiled: January 14, 1994Date of Patent: July 25, 1995Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello, Melis Hasselaar
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Patent number: 5312984Abstract: A continuous process for making N,N-dimethylacrylamide (NNDMA) is disclosed which uses a commodity chemical, namely vinyl chloride (VCl), which is amidated with dimethylamine (DMA) and carbon monoxide in the presence of a supported palladium(O) triorganophosphine catalyst used under conditions where the ratio of P/Pd is critical. The continous process unexpectedly provides the catalyst with long life because the reaction can be carried out in a moving bed of catalyst in the presence of enough acetonitrile solvent to prevent deposition of DMA.HCl, formed during the reaction, in the pores of the catalyst support.Type: GrantFiled: September 23, 1992Date of Patent: May 17, 1994Assignee: The B. F. Goodrich CompanyInventor: Paul P. Nicholas
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Patent number: 5241048Abstract: Chemical reactions are readily carried out using supercritical carbon dioxide as the reaction medium. Supercritical carbon dioxide is of special value as a reaction medium in reactions for synthesizing polypeptides, for sequencing polypeptides, or for amino acid analysis.Type: GrantFiled: November 6, 1990Date of Patent: August 31, 1993Assignee: Protein Technologies, Inc.Inventors: Leon E. Barstow, Glen D. Ward, Milan Bier
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Patent number: 5189221Abstract: A mixture of C.sub.1 -C.sub.4 mono-, di- and trialkylamines is separated by adding at least about an equimolar amount, based on the amine mixture, of a formyldialkanolamine selected from the group consisting of formyldiethanolamine, formyl aminoethylethanolamine and formyl 2-(2-aminoethylamino)-ethanol to the alkyl amine mixture, at a temperature of about 120.degree. to about 160.degree. C. and a pressure of about 500 to about 3,000 psig to provide a reaction mixture comprising the trialkylamine, the formyl dialkylamine and the formyl monoalkylamine, together with unreacted formyldialkanolamine and the corresponding alkanolamine, by separately recovering the trialkyl amine, the formyl dialkylamine and the formyl monoalkylamine from the reaction mixture, by reacting the dialkyl amine with said alkanolamine at atmospheric pressure at temperature of about 120.degree. to about 140.degree. C.Type: GrantFiled: November 19, 1990Date of Patent: February 23, 1993Assignee: Texaco Chemical CompanyInventors: Roger G. Duranleau, Robert L. Zimmerman
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Patent number: 5159113Abstract: A unique two-step process is disclosed for the surprisingly high rate of amidation of vinyl chloride (VCl) with carbon monoxide and certain amines catalyzed by an effective amount of monodentate tertiary phosphonium complexes of Pd(0). The rate is orders of magnitude faster than that of other monochloroalkenes. When compared with the three chloropropenes, the simplest alkyl-substituted derivatives of VCl, rates differ by a factor of about 40 to 70 with ammonia as the amine. The reaction product with VCl is mainly the Michael adduct of the amine with the acrylamide produced. However, the chloroprenes give the propenamides with retention of configuration in the case of cis- and trans-1-chloropropene, and no adduct formation. The formation of this adduct has an important influence on catalyst stability since it can compete with the addition of the tertiary-phosphonium ligand from the catalyst complex.Type: GrantFiled: February 29, 1988Date of Patent: October 27, 1992Assignee: The B. F. Goodrich CompanyInventor: Peter P. Nicholas
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Patent number: 5128475Abstract: A process for the preparation of an amide, which comprises reacting an acetylenically or olefinically unsaturated compound with carbon monoxide and a nitrogen compound selected from ammonia and a primary or secondary amine or amide, in the presence of a catalyst system which comprises:a) a source of a Group VIII metal,b) a phosphine having an aromatic substituent which contains an imino nitrogen atom, andc) a protonic acid.Type: GrantFiled: June 11, 1990Date of Patent: July 7, 1992Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5001224Abstract: Chemical reactions are readily carried out using supercritical carbon dioxide as the reaction medium. Supercritical carbon dioxide is of special value as a reaction medium in reactions for synthesizing polypeptides, for sequencing polypeptides, or for amino acid analysis.Type: GrantFiled: March 11, 1988Date of Patent: March 19, 1991Assignee: Protein Technologies, Inc.Inventors: Leon E. Barstow, Glen D. Ward, Milan Bier
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Patent number: 5001268Abstract: The N-arylsubstituted amides, e.g.Type: GrantFiled: May 23, 1990Date of Patent: March 19, 1991Assignee: Rhone-Poulenc ChimieInventor: Francois Metz
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Patent number: 4937380Abstract: 1,3-butadienes are catalytically hydrocarbamylated to make 3-pentenamides.Type: GrantFiled: October 14, 1986Date of Patent: June 26, 1990Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4918222Abstract: An N-acetylglycine is manufactured by reacting paraformaldehyde with an acetamide and carbon monoxide in the present of a cobalt-containing catalyst promoted by a sulfoxide or dinitride compounds. The presence of sulfoxide or dinitrile ligands are essential for the high yield synthesis of N-acetylglycine and good cobalt recovery.Type: GrantFiled: August 10, 1987Date of Patent: April 17, 1990Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton, Ernest L. Yeakey
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Patent number: 4892687Abstract: A process is disclosed for producing N-acetyl-aminoacid which comprises reacting a feedstock from the group consisting of simple olefins, acetamide and synthesis gas with a catalyst comprising a cobalt-containing compound promoted by a bidental-phosphine ligand in a solvent at a pressure of 500 psi or greater and a temperature of 50.degree. C. or greater. The presence of the ligand increases both reaction rate and cobalt catalyst stability.Type: GrantFiled: October 8, 1986Date of Patent: January 9, 1990Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4866177Abstract: A N-alkyl amide derivative is synthesized in one-step by reacting an olefin, nitrogen-containing compound and carbon monoxide with a catalyst comprising a rhodium-containing compound in the presence of water at a pressure of at least 500 psi and a temperature of at least 50.degree. C.Type: GrantFiled: November 24, 1986Date of Patent: September 12, 1989Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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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: 4761499Abstract: High yields of olefinic esters and amides, and the like are derived from a process wherein vinyl dihalides are carbonylated in the presence of a palladium catalyst and a primary or secondary amine base or tertiary amine, depending on the desired product, and a solvent.Type: GrantFiled: June 2, 1987Date of Patent: August 2, 1988Assignee: Akzo America Inc.Inventor: Ronald A. Epstein
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Patent number: 4704409Abstract: A process for preparing a poly(alkylene amido-ether) polyols by reaction of a bicyclic amide acetal with a polyol at a temperature in the range of from 140.degree.-240.degree. C. and the use of these poly(alkylene amidoether) polyols in the formation of polyurethanes are described.Type: GrantFiled: January 20, 1987Date of Patent: November 3, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4691048Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.Type: GrantFiled: May 10, 1985Date of Patent: September 1, 1987Assignee: Institut Francais du PetroleInventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
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Patent number: 4613684Abstract: A commercially economical process for preparing a carboxylic acid ester from a carboxylic acid amide is disclosed. The process is very meritorious, since it produces neither ammonia nor ammonium sulfates. Rather, the process by-produces formamides which are very useful compounds as solvents. Further, formamide can easily be converted to hydrogen cyanide by dehydration. The process comprises reacting a carboxylic acid amide with a formic acid ester and/or methanol and carbon monoxide in the presence of a bicyclic amidine or tertiary amine catalyst and optionally in the co-existence of a metal carbonyl. An industrial process for preparing methyl methacrylate which is a materialization of the process shown above is described in detail referring to a figure.Type: GrantFiled: September 27, 1984Date of Patent: September 23, 1986Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tetsuo Aoyama, Koichi Kida, Takako Uchiyama
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Patent number: 4594445Abstract: The present invention provides a process for the preparation of aryl carboxylic acids and derivatives thereof by the carbonylation of diaryliodonium salts. The diaryliodonium salts are reacted with carbon monoxide and water or an alcohol or amine in a base reaction medium having a pK.sub.b greater than about 8.Type: GrantFiled: January 7, 1985Date of Patent: June 10, 1986Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, James R. Overton, David D. Cornell
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Patent number: 4588833Abstract: Substituted succinic acid amides, in particular substituted succinic acid amides containing differing derivative groups, are prepared by reacting unsaturated carboxamides with carbon monoxide and with a nucleophilic component containing at least one mobile hydrogen atom, in the presence of cobalt compounds and, if appropriate, in the presence of one or more tertiary nitrogen bases, under an elevated pressure and at an elevated temperature.Type: GrantFiled: October 26, 1984Date of Patent: May 13, 1986Assignee: Bayer AktiengesellschaftInventors: Jurgen Kadelka, Hans-Helmut Schwarz
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Patent number: 4582929Abstract: This invention is a process for the carbonylation of an organic halide to prepare a carbonyl-containing compound, and recovery of halogen values in a useful form which comprises(a) contacting an organic halide with carbon monoxide and an esterifying agent, a primary or secondary amine, or hydrogen gas, in an inert organic solvent in the presence of a water-insoluble tertiary amine or pyridine ring-containing compound, and a catalytic amount of a Group VIII metal catalyst, under conditions such that an organic ester, amide or aldehyde is prepared and the halide generated in the process forms a salt with tertiary amine or pyridine compound wherein the halide is bromine or iodine;(b) separating the organic ester, amide or aldehyde from the reaction mixture which contains the tertiary amine or pyridine compound-halide salt;(c) contacting the reaction mixture containing the tertiary amine or pyridine compound-halide salt mixture with a concentrated aqueous solution of an alkali metal base or alkaline earth metal bType: GrantFiled: December 24, 1984Date of Patent: April 15, 1986Assignee: The Dow Chemical CompanyInventor: Robert A. DeVries
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Patent number: 4565866Abstract: The instant invention relates to a process for the preparation of formamides in which ammonia, a primary or a secondary amine is reacted with carbon monoxide at an elevated temperature and pressure in the presence of a mixture consisting of a phenol and a phenate salt from the group consisting of an alkali metal phenate and an alkaline earth metal phenate, said phenol and said phenate salt each having the radical: ##STR1## wherein R is selected from the group consisting of an alkyl radical having from 3 to 18 carbon atoms and a hydroxyaryl radical of the formula: ##STR2## in which R' is an alkylene group having from 2 to 5 carbon atoms and in which x has a value of 1 to 2 when R is said alkyl radical and x has a value of 1 when R is said hydroxyaryl radical.Type: GrantFiled: January 24, 1984Date of Patent: January 21, 1986Assignee: Texaco Inc.Inventors: Roger G. Duranleau, John F. Knifton, George P. Speranza
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Patent number: 4558157Abstract: In the catalytic reaction of ammonia or formamide with CO and H.sub.2, exceptionally high yields of mono- and di-methyl formamide are obtained among the reaction products when the reaction is carried out in the presence of a platinum group catalyst soluble in the reaction medium, particularly a compound or complex of ruthenium or rhodium, employing a relatively non-volatile polar solvent which does not contain an active methyl function and which does not enter into the reaction producing formamide compounds. The pressure employed is in the range of 3000-8000 psi with a hydrogen partial pressure of at least 1500 psi, the preferred solvent being sulfolane.Type: GrantFiled: June 5, 1984Date of Patent: December 10, 1985Assignee: Air Products and Chemicals, Inc.Inventors: John A. Marsella, Guido P. Pez
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Patent number: 4556734Abstract: A process is disclosed for the production of formamides, particularly N,N-dimethylformamide and N-methylformamide, by the reaction of synthesis gas with ammonia in the presence of a catalyst system comprising a ruthenium species coupled with quaternary phosphonium salts. The catalyst system typically produces high yields of formamides, a large percentage of which may comprise N,N-dimethylformamide, N-methylformamide or formamide itself.Type: GrantFiled: November 4, 1983Date of Patent: December 3, 1985Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4554345Abstract: This invention describes a process for preparing liquid polyamides comprising contacting a nitrile, amine and water in the presence of a carbon dioxide catalyst.Type: GrantFiled: May 2, 1983Date of Patent: November 19, 1985Assignee: The Standard Oil CompanyInventors: Janice L. Greene, Roman Loza
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Patent number: 4539427Abstract: Formamides e.g. diethylformamide are prepared by reacting a primary or secondary amine e.g. diethylamine or ammonia with (a) an alkyl formate or (b) carbon monoxide and an alkanol in the presence, as catalyst, of (i) a compound containing an amidine group or (ii) a Group V element-containing Lewis base and an epoxide. The Lewis base can be a trivalent nitrogen or phosphorus-containing compound. The amidine group which can be cyclic or acyclic can form part of a guanidine group.Type: GrantFiled: October 18, 1983Date of Patent: September 3, 1985Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4529822Abstract: This invention relates to preparing formamide compounds in a process which comprises reacting an amine with a formylalkanolamine in the presence of carbon monoxide in which the mole ratio of amine to formylalkanolamine ranges from 0.2:1 to 5:1. The reaction is conducted at a temperature ranging from about 50.degree. to 300.degree. C. and a pressure ranging from about 100 to 10,000 psig. The amine employed in the reaction has the formula: ##STR1## wherein R' is hydrogen, an alkyl group of 1 to 10 carbon atoms, cyclohexyl, or --R"--O--R'", wherein R" is a divalent alkylene group of 2 to 4 carbon atoms and R'" is an alkyl group of 1 to 3 carbon atoms; and R is hydrogen or an alkyl group of 1 to 10 carbon atoms. The formylalkanolamine employed in the reaction has the formula: ##STR2## wherein R is an alkylene group of 1 to 3 carbon atoms, z is 0 or 1 and y is 1 or 2 and the sum of y and z is 2.Type: GrantFiled: October 19, 1983Date of Patent: July 16, 1985Assignee: Texaco, Inc.Inventors: Roger G. Duranleau, Clifford L. Lambert, Jr.
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Patent number: 4510326Abstract: A process for the preparation of a formylalkanolamine which comprises reacting carbon monoxide with an alkanolamine at a temperature ranging from about 60.degree. to 300.degree. C. and at a pressure ranging from about 100 to 10,000 psig, said alkanolamine being represented by the formula:RNH.sub.x --CH.sub.2 --(X).sub.z --CH.sub.2 --OH).sub.yin which x is 0 or 1, R is hydrogen, a methyl or an aminoethyl radical with the proviso that R is hydrogen when x is 0, y is 1 or 2 and the sum of x and y is 2, X is a divalent radical from the group consisting of --CH.sub.2 -- and --CHOH--, and z is 0 or 1.Type: GrantFiled: July 18, 1983Date of Patent: April 9, 1985Assignee: Texaco Inc.Inventors: Clifford L. Lambert, Jr., Roger G. Duranleau
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Patent number: 4447640Abstract: The invention is a process for preparing .alpha.-unsaturated carboxylic esters or amides comprising contacting a 1,2-dihaloalkane, an alcohol or amine, and carbon monoxide, in the presence of a catalytic amount of a group VIII metal at elevated temperatures and pressures. The invention further includes preventing the .alpha.-unsaturated carboxylic esters or amides prepared by the addition of a free radical inhibitor capable of improving catalyst lifetime to the reaction mixture.Type: GrantFiled: May 17, 1982Date of Patent: May 8, 1984Assignee: The Dow Chemical CompanyInventor: Kathryn A. Eickholt
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Patent number: 4379928Abstract: Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.Type: GrantFiled: March 4, 1981Date of Patent: April 12, 1983Assignee: Union Carbide CorporationInventor: Spyros Theodoropulos