Preparing Directly From Carbon Monoxide Or Carbon Dioxide Patents (Class 564/132)
  • Publication number: 20150105571
    Abstract: 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: Application
    Filed: November 26, 2012
    Publication date: April 16, 2015
    Inventors: Ralf Jackstell, Carolin Ziebart, Christopher Federsel, Matthias Beller
  • Patent number: 8877971
    Abstract: 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: Grant
    Filed: April 4, 2012
    Date of Patent: November 4, 2014
    Assignee: Commissariat a l'Energie Atomique et aux Energies Alternatives
    Inventors: Thibault Cantat, Christophe Gomes, Olivier Jacquet
  • Patent number: 8829226
    Abstract: 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: Grant
    Filed: January 28, 2011
    Date of Patent: September 9, 2014
    Assignee: Zhejiang Jiuzhou Pharmaceutical Co., Ltd
    Inventors: Xianyi Zhang, Shaoqing Ge, Daqing Che
  • Publication number: 20140018576
    Abstract: 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: Application
    Filed: April 4, 2012
    Publication date: January 16, 2014
    Applicant: Commissariat A L'Energie Atomique Et Aux Energies Alternatives
    Inventors: Thibault Cantat, Christophe Gomes, Olivier Jacquet
  • Patent number: 8513463
    Abstract: 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: Grant
    Filed: April 15, 2009
    Date of Patent: August 20, 2013
    Assignees: The University of Cape Town, Carl Von Ossietzky Universitat Oldenburg
    Inventors: Michael Christian Maximilian Claeys, Eric Wilhelmus Josephus Van Steen, Frank Roessner, Tawanda Stephen Sango
  • Publication number: 20130102807
    Abstract: 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: Application
    Filed: July 26, 2012
    Publication date: April 25, 2013
    Applicant: BASF SE
    Inventors: Thomas Schaub, Rocco Paciello, Marek Pazicky, Giuseppe Fachinetti, Debora Preti
  • Publication number: 20130066102
    Abstract: 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: Application
    Filed: January 28, 2011
    Publication date: March 14, 2013
    Applicant: ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD
    Inventors: Xianyi Zhang, Shaoqing Ge, Daqing Che
  • Publication number: 20120071690
    Abstract: 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: Application
    Filed: September 16, 2011
    Publication date: March 22, 2012
    Applicant: BASF SE
    Inventors: Marek Pazicky, Thomas Schaub, Ansgar Gereon Altenhoff, Donata Maria Fries, Rocco Paciello
  • Publication number: 20110172456
    Abstract: 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 f
    Type: Application
    Filed: May 25, 2009
    Publication date: July 14, 2011
    Applicant: BASF SE
    Inventors: Nina Challand, Ansgar Gereon Altenhoff, Joachim Schmidt-Leithoff, Kathrin Wissel-Stoll, Michael Rack, Joachim Rheinheimer
  • Patent number: 7960585
    Abstract: 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: Grant
    Filed: April 1, 2009
    Date of Patent: June 14, 2011
    Assignee: Taminco
    Inventors: Mondher Srasra, Pierre Jacobs, Bert Sels, Maria Christina Jacoba Tielen, Kristof Moonen, Peter Roose, Ivan Vanden Eynde
  • Publication number: 20110092728
    Abstract: 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: Application
    Filed: April 15, 2009
    Publication date: April 21, 2011
    Applicants: THE UNIVERSITY OF CAPE TOWN, CARL VON OSSIETZKY UNIVERSITAT OLDENBURG
    Inventors: Michael Christian Maximilian Claeys, Eric Wilhelmus Josephus Van Steen, Frank Roessner, Tawanda Stephen Sango
  • Publication number: 20090247744
    Abstract: 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: Application
    Filed: June 10, 2009
    Publication date: October 1, 2009
    Inventors: Edward D Daugs, Wei-Jun Peng, Cynthia L Rand
  • Patent number: 6642420
    Abstract: 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 the
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: November 4, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Armin Ulonska, Rocco Paciello
  • Patent number: 6441233
    Abstract: 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: Grant
    Filed: June 21, 2001
    Date of Patent: August 27, 2002
    Assignee: Solvias AG
    Inventors: Anita Schnyder, Adriano Indolese, Gerald Mehltretter
  • Patent number: 6441234
    Abstract: 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: Grant
    Filed: July 17, 2001
    Date of Patent: August 27, 2002
    Assignee: Abbott Laboratories
    Inventors: Jürgen Dahlhaus, Jörn Karl, Michael Schulz, Anne Wenzel, Wolfgang Harder, Arthur Höhn
  • Patent number: 6388085
    Abstract: 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: Grant
    Filed: August 23, 2000
    Date of Patent: May 14, 2002
    Assignee: Board of Trustees of Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6326517
    Abstract: 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: Grant
    Filed: December 10, 1999
    Date of Patent: December 4, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Takashi Kume, Michio Ishida, Satoru Narizuka, Yuzuru Morino, Makoto Koide
  • Patent number: 5919979
    Abstract: 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: Grant
    Filed: September 28, 1993
    Date of Patent: July 6, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John William Mitchell, Thomas Albert Johnson
  • Patent number: 5763662
    Abstract: 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: Grant
    Filed: November 20, 1996
    Date of Patent: June 9, 1998
    Assignees: Research Development Corporation of Japan, NKK Corporation
    Inventors: Takao Ikariya, Philip Gregory Jessop, Yi Hsiao, Ryoji Noyori
  • Patent number: 5672750
    Abstract: 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: Grant
    Filed: May 31, 1996
    Date of Patent: September 30, 1997
    Assignee: Eastman Chemical Company
    Inventor: Robert James Perry
  • Patent number: 5436356
    Abstract: 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: Grant
    Filed: January 14, 1994
    Date of Patent: July 25, 1995
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Dennis H. L. Pello, Melis Hasselaar
  • Patent number: 5312984
    Abstract: 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: Grant
    Filed: September 23, 1992
    Date of Patent: May 17, 1994
    Assignee: The B. F. Goodrich Company
    Inventor: Paul P. Nicholas
  • Patent number: 5241048
    Abstract: 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: Grant
    Filed: November 6, 1990
    Date of Patent: August 31, 1993
    Assignee: Protein Technologies, Inc.
    Inventors: Leon E. Barstow, Glen D. Ward, Milan Bier
  • Patent number: 5189221
    Abstract: 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: Grant
    Filed: November 19, 1990
    Date of Patent: February 23, 1993
    Assignee: Texaco Chemical Company
    Inventors: Roger G. Duranleau, Robert L. Zimmerman
  • Patent number: 5159113
    Abstract: 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: Grant
    Filed: February 29, 1988
    Date of Patent: October 27, 1992
    Assignee: The B. F. Goodrich Company
    Inventor: Peter P. Nicholas
  • Patent number: 5128475
    Abstract: 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: Grant
    Filed: June 11, 1990
    Date of Patent: July 7, 1992
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5001268
    Abstract: The N-arylsubstituted amides, e.g.
    Type: Grant
    Filed: May 23, 1990
    Date of Patent: March 19, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventor: Francois Metz
  • Patent number: 5001224
    Abstract: 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: Grant
    Filed: March 11, 1988
    Date of Patent: March 19, 1991
    Assignee: Protein Technologies, Inc.
    Inventors: Leon E. Barstow, Glen D. Ward, Milan Bier
  • Patent number: 4937380
    Abstract: 1,3-butadienes are catalytically hydrocarbamylated to make 3-pentenamides.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: June 26, 1990
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 4918222
    Abstract: 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: Grant
    Filed: August 10, 1987
    Date of Patent: April 17, 1990
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton, Ernest L. Yeakey
  • Patent number: 4892687
    Abstract: 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: Grant
    Filed: October 8, 1986
    Date of Patent: January 9, 1990
    Assignee: Texaco Inc.
    Inventor: Jiang-Jen Lin
  • Patent number: 4866177
    Abstract: 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: Grant
    Filed: November 24, 1986
    Date of Patent: September 12, 1989
    Assignee: Texaco Inc.
    Inventor: Jiang-Jen Lin
  • Patent number: 4847411
    Abstract: A process for making a diamide of the formula ##STR1## by reacting a monoamide compound of the formula ##STR2## with CO and an amine or ammonia of the formula R.sub.7 R.sub.8 NH in the liquid phase under essentially anhydrous conditions at a temperature in the range from 120.degree. to 210.degree. C., where each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 is selected independently from H and a C.sub.1 to C.sub.12 hydrocarbyl containing no ethylenic or acetylenic unsaturation.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: July 11, 1989
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 4761499
    Abstract: 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: Grant
    Filed: June 2, 1987
    Date of Patent: August 2, 1988
    Assignee: Akzo America Inc.
    Inventor: Ronald A. Epstein
  • Patent number: 4704409
    Abstract: 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: Grant
    Filed: January 20, 1987
    Date of Patent: November 3, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4691048
    Abstract: 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: Grant
    Filed: May 10, 1985
    Date of Patent: September 1, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
  • Patent number: 4613684
    Abstract: 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: Grant
    Filed: September 27, 1984
    Date of Patent: September 23, 1986
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tetsuo Aoyama, Koichi Kida, Takako Uchiyama
  • Patent number: 4594445
    Abstract: 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: Grant
    Filed: January 7, 1985
    Date of Patent: June 10, 1986
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, James R. Overton, David D. Cornell
  • Patent number: 4588833
    Abstract: 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: Grant
    Filed: October 26, 1984
    Date of Patent: May 13, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Kadelka, Hans-Helmut Schwarz
  • Patent number: 4582929
    Abstract: 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 b
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: April 15, 1986
    Assignee: The Dow Chemical Company
    Inventor: Robert A. DeVries
  • Patent number: 4565866
    Abstract: 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: Grant
    Filed: January 24, 1984
    Date of Patent: January 21, 1986
    Assignee: Texaco Inc.
    Inventors: Roger G. Duranleau, John F. Knifton, George P. Speranza
  • Patent number: 4558157
    Abstract: 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: Grant
    Filed: June 5, 1984
    Date of Patent: December 10, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John A. Marsella, Guido P. Pez
  • Patent number: 4556734
    Abstract: 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: Grant
    Filed: November 4, 1983
    Date of Patent: December 3, 1985
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4554345
    Abstract: 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: Grant
    Filed: May 2, 1983
    Date of Patent: November 19, 1985
    Assignee: The Standard Oil Company
    Inventors: Janice L. Greene, Roman Loza
  • Patent number: 4539427
    Abstract: 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: Grant
    Filed: October 18, 1983
    Date of Patent: September 3, 1985
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4529822
    Abstract: 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: Grant
    Filed: October 19, 1983
    Date of Patent: July 16, 1985
    Assignee: Texaco, Inc.
    Inventors: Roger G. Duranleau, Clifford L. Lambert, Jr.
  • Patent number: 4510326
    Abstract: 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: Grant
    Filed: July 18, 1983
    Date of Patent: April 9, 1985
    Assignee: Texaco Inc.
    Inventors: Clifford L. Lambert, Jr., Roger G. Duranleau
  • Patent number: 4447640
    Abstract: 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: Grant
    Filed: May 17, 1982
    Date of Patent: May 8, 1984
    Assignee: The Dow Chemical Company
    Inventor: Kathryn A. Eickholt
  • Patent number: 4379928
    Abstract: Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: April 12, 1983
    Assignee: Union Carbide Corporation
    Inventor: Spyros Theodoropulos
  • Patent number: 4331612
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen oxide compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: July 16, 1980
    Date of Patent: May 25, 1982
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase