Carbonylation Patents (Class 560/97)
  • Patent number: 8703992
    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 fo
    Type: Grant
    Filed: May 25, 2009
    Date of Patent: April 22, 2014
    Assignee: BASF SE
    Inventors: Nina Challand, Ansgar Gereon Altenhoff, Joachim Schmidt-Leithoff, Kathrin Wissel-Stoll, Michael Rack, Joachim Rheinheimer
  • Publication number: 20100160632
    Abstract: The present invention relates to zinc amide bases of the general formula (I) (R1R2N)2—Zn.aMgX12.bLiX2??(I) wherein R1 and R2 are each independently selected from substituted or unsubstituted, linear or branched alkyl, alkenyl, alkynyl or silyl derivatives thereof, and substituted or unsubstituted aryl or heteroaryl, and wherein R1 and R2 can form together a ring structure, or R1 and/or R2 can be part of a polymer structure; X12 is a divalent anion or two monovalent anions that are independent from each other; X2 is a monovalent anion; a is >0; and b is >0. The zinc amide bases can be used, amongst other things, for deprotonation and metallization of aromatics.
    Type: Application
    Filed: May 14, 2008
    Publication date: June 24, 2010
    Inventors: Paul Knochel, Stefan Wunderlich
  • Patent number: 7098363
    Abstract: A process for the production of a product comprising a carboxylic acid having n+1 carbon atoms which process comprises reacting in the liquid phase at elevated temperature and pressure a composition comprising an alcohol having n carbon atoms and/or a reactive derivative thereof, a halogen and/or a halogen compound promoter, water and carbon monoxide in the presence of hydrogen and a heterogeneous catalyst comprising a Group VIII noble metal species on a polymeric resin having a functional group selected from nitrogen-containing heterocycles.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: August 29, 2006
    Assignee: BP Chemicals Limited
    Inventor: Michael David Jones
  • Patent number: 6653502
    Abstract: A process for preparing phenylacetic acid derivatives of the formula (I) by reacting benzyl chlorides of the formula (II) with a compound of the formula R6OH and with carbon monoxide in a dipolar aprotic solvent in the presence of a catalyst which comprises at least one compound of a transition metal of subgroup VIII of the Periodic Table of the Elements, where R1, R2, R3, R4, and R5 independently of one another are the following radicals: a hydrogen or fluorine atom; a CH2Cl radical; a HO2CCH═CH—, NC— or CF3— group; an alkyl, alkoxy or acyloxy radical having in each case 1 to 18 carbon atoms; or a C6-C18-aryloxy, aryl or heteroaryl radical.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: November 25, 2003
    Assignee: Clariant GmbH
    Inventor: Holger Geissler
  • Publication number: 20030191339
    Abstract: The invention relates to a catalyst system for carbonylating olefinically or acetylenically unsaturated compounds with carbon monoxide and a nucleophile compound, containing (a) palladium; (b) a phosphine and (c) a polymer containing nitrogen which is soluble in the reaction mixture, with the exception of polyvinyl polymers with aromatic radicals containing nitrogen on the polymer chain. The invention also relates to a method for carbonylation in the presence of one such catalyst system.
    Type: Application
    Filed: March 25, 2003
    Publication date: October 9, 2003
    Inventors: Martin Schfer, Michael Slany, Edgar Zeller, Michael Rper, Michael Schulz, G?uuml;nter Grimm
  • Patent number: 6521783
    Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: February 18, 2003
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
  • Patent number: 6355702
    Abstract: Compounds containing unsaturated aliphatic moieties which are linked to each other by a tertiary oxycarbonyl containing acyclic moiety are basis for compositions which are cured to polymer networks which are thermally decomposable to provide residue which can be dissolved to allow repair of inoperative assemblies by replacement of inoperative components or recovery or recycling of operative elements which are affixed in assemblies by the cured compositions.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: March 12, 2002
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Kenji Ogino
  • Patent number: 6355711
    Abstract: A plasticizer ester prepared from the catalytic reaction of (1) at least one branched C7-C11 oxo alcohol prepared from C6-C10 olefins via hydroformylation and having at least 50% methyl branching at the beta carbon, and (2) at least one acid or anhydride.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: March 12, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Allen David Godwin, Dwight McLean Lyman
  • Patent number: 6127574
    Abstract: A process for the production of a carboxylic acid and/or a carboxylic acid anhydride which process comprises contacting a reaction composition comprising an alcohol and/or a carboxylic acid ester, optionally water, a first hydrocarbyl halide and/or a hydrocarbyl ether reactant and a second hydrocarbyl halide promoter, the first and second hydrocarbyl halides being the same or different, with carbon monoxide in the presence of a catalyst comprising an insoluble imidazole-containing resin supporting a Group VIII metal species.
    Type: Grant
    Filed: June 16, 1998
    Date of Patent: October 3, 2000
    Assignee: BP Chemicals Limited
    Inventors: Mark Julian Howard, Michael David Jones
  • Patent number: 5719313
    Abstract: The invention relates to a novel carbonylation catalyst system and a process for the carbonylation of acetylenically unsaturated compounds, whereby a feedstock, comprising an acetylenically unsaturated compound and a relatively minor amount of an 1,2-alkadiene compound, is contacted under carbonylation conditions with carbon monoxide and a hydroxylated co-reactant in the presence of the novel carbonylation catalyst system that is based on:a) a source of cations of one or more metals of Group VIII of the Periodic Table;b) a phosphine of the general formulae PR.sup.1 R.sup.2 R.sup.3, R.sup.1 R.sup.2 M--R--PR.sup.3 R.sup.3, or R.sup.2 R.sup.3 M--R--PR.sup.1 R.sup.3, wherein R.sup.1 represents a substituted or non-substituted 6-membered heteroaryl group having at least one imino nitrogen atom next to the carbon atom that is attached to the phosphorus atom; R.sup.2 represents a halogenated aryl group; R.sup.3 or each of the R.sup.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: February 17, 1998
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 5414109
    Abstract: A process for the carbonylation of acetylenically unsaturated compounds in the presence of a nucleophilic compound having one or more removable hydrogen atoms and a catalyst system based on a source of platinum, a bisphosphine of the formula R.sub.1 R.sub.2 PRPR.sub.3 R.sub.4 wherein each of R.sub.1,R.sub.2,R.sub.3 and R.sub.4 independently represents a hydrocarbyl group and R represents a bivalent bridging group and a source of anions from a conjugated base of an acid having a pKa of less than 4.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: May 9, 1995
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Eric Kragtwijk
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5258546
    Abstract: The invention relates to a catalyst system, which comprises a source of a Group VIII metal and a polyphosphine. The invention further relates to a process for the preparation of alpha, beta-olefinically unsaturated compounds utilizing this catalyst system.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: November 2, 1993
    Assignee: Shell Oil Company
    Inventors: Peter A. Klusener, Hans A. Stil, Fit Drent, Peter Arnoldy
  • Patent number: 5245072
    Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula -(C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.
    Type: Grant
    Filed: February 24, 1992
    Date of Patent: September 14, 1993
    Assignee: Mobil Oil Corporation
    Inventors: Thomas J. Giacobbe, George A. Ksenic
  • Patent number: 5233075
    Abstract: A process comprising preparing an aromatic carboxylic ester and an alkyl iodide by carboxylating an aromatic iodide in the presence of an alkylating agent and a catalytic amount of a transition metal under aromatic carboxylic ester and alkyl iodide forming conditions of temperature, pressure and ultrasound.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: August 3, 1993
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Andrew J. Matosky
  • Patent number: 5189198
    Abstract: A process for efficiently preparing an unsaturated dicarboxylic acid diester, which comprises reacting a conjugated diene, carbon monoxide, an alcohol and oxygen in the presence of a catalyst comprising (a) a platinum metal, a salt thereof or a complex compound of a platinum metal, (b) at least one metal salt selected from the group consisting of a copper salt, an iron salt and a manganese salt and (C) at least one compound selected from the group consisting of (1) an alkali metal compound or an alkaline earth metal compound, (2) a rare earth metal compound, (3) a metal compound of the groups IIIA, IVA, IVB, VA, VB or VIA, and (4) a metal carbonyl complex. The unsaturated dicarboxylic acid diester is useful as an intermediate material in industrial chemical processes and can be efficiently prepared without the use of a dehydrating agent.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: February 23, 1993
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Takashi Kumazawa, Tetsuo Ishibashi, Mitsugu Kanzawa
  • Patent number: 5158921
    Abstract: A catalyst system, which containsa) a source of a group VIII metal, andb) a phosphine of general formula: ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are independently selected from an optionally substituted aryl group and a group of general formula: ##STR2## wherein eachh of A, X, Y and Z is independently selected from a nitrogen atom, a CH group and a group of formula CR wherein R represents a hydroxyl group, an amino group, an amido group, a cyano group, an aryl group, an aryloxy group, a halogen atom, an optionally substituted hydrocarbyl group or an optionally substituted hydrocarbyloxy group, it also being possible for two adjacent CR groups to form a ring, provided that at least one of R.sup.1, R.sup.2 and R.sup.3 represents a group of formula (II) in which at least one of A and Z represents a group of formula CR; or an acid addition salt thereof.Also disclosed is the use of the catalyst system in the selective carbonylation of unsaturated hydrocarbons.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: October 27, 1992
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Petrus H. M. Budzelaar, Willem W. Jager
  • Patent number: 5028734
    Abstract: A process for the selective carbonylation of a conjugated diene by contacting with carbon monoxide in the presence of a hydroxyl-group-containing compound such as water, alcohol, phenol or carboxylic acid in liquid phase using a catalyst system formed by the combination of:(a) a palladium compound and(b) at least one organic bidentate phosphine.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: July 2, 1991
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5003104
    Abstract: This invention involves a process for the carbonylation of a carbonylatable reactant, e.g., an alkyl ester, a dialkyl ether or mixtures thereof by reacting the same with carbon monoxide. The process comprises effecting the carbonylation in the presence of a solution of a catalyst system containing a rhodium compound, an iodide and a lithium component at a temperature of from 50.degree. C. to 400.degree. C. at a carbon monoxide partial pressure of 1 psig to 15,000 psig. Hydrogen may also be present. The invention also concerns a carbonylation catalyst system effective for the addition of carbon monoxide to a carbonylatable reactant which comprises a solution containing as essential components a rhodium containing active component, an iodide and a lithium component.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: March 26, 1991
    Assignee: BP Chemicals Limited
    Inventors: Frank E. Paulik, Arnold Hershman, Walter R. Knox, Robert G. Schultz, James F. Roth
  • Patent number: 4990657
    Abstract: A process for the preparation of an aromatic acid comprising the step of combining an aromatic halide having at least one iodine or bromine substituent with:a. a water-immiscible organic solvent,b. a palladium-based catalyst,c. a palladium-complexing agent,d. a tertiary nitrogen-containing organic base,e. water andf. carbon monoxide.The process is performed in a two-phase liquid medium and in the substantial absence of a phase transfer agent.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: February 5, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Norbert Bluthe, Robert Perron
  • Patent number: 4933468
    Abstract: Amide-imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide having an isolated halogen function, and with an amine, in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: June 12, 1990
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, S. Richard Turner
  • Patent number: 4933467
    Abstract: Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amide in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: June 12, 1990
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, S. R. Turner
  • Patent number: 4933466
    Abstract: Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amine in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.Acyclic imides are prepared by reacting CO with an activated halide and an amide (primary or secondary) in the presence of a Pd catalyst and a base.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: June 12, 1990
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, Sam R. Turner
  • Patent number: 4912250
    Abstract: Disclosed is a process for the co-production of an aromatic carboxylic esters and alkyl iodide by the carbonylation of an aromatic iodide in the absence of a Bronsted base and in the presence of an ether and a nickel catalyst.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: March 27, 1990
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanny C. Treece
  • Patent number: 4904817
    Abstract: Disclosed is an improved process for the manufacture of aromatic carboxylic acid esters by the carbonylation of aromatic iodides wherein the amount of the corresponding unesterified carboxylic acid in the product obtained from the process is minimized. The process comprises carbonylating an aromatic iodide in the presence of carbon monoxide, a Group VIII metal catalyst, an inorganic adsorbent and an alkanol to co-produce an aromatic carboxylic acid ester and an alkyl iodide.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: February 27, 1990
    Assignee: Eastman Kodak Company
    Inventor: Guy R. Steinmetz
  • Patent number: 4868328
    Abstract: Process for the selective oxidative carbonylation of a conjugated diene with carbon monoxide and an alcohol in a quantity of at least 2 mol equivalents per mol diene, in the presence of a catalyst system which comprises the following components:(a) a compound of a metal, selected from one or more platinum group metals,(b) an oxidizing agent in the form of quinone and/or derivatives thereof, and(c) a compound of a metal, selected from manganese or vanadium.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: September 19, 1989
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4866200
    Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a palladium catalyst.
    Type: Grant
    Filed: August 4, 1988
    Date of Patent: September 12, 1989
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
  • Patent number: 4851564
    Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a rhodium catalyst.
    Type: Grant
    Filed: February 22, 1988
    Date of Patent: July 25, 1989
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule
  • Patent number: 4847406
    Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a ruthenium catalyst.
    Type: Grant
    Filed: January 12, 1987
    Date of Patent: July 11, 1989
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule
  • Patent number: 4827018
    Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a nickel catalyst.
    Type: Grant
    Filed: October 22, 1987
    Date of Patent: May 2, 1989
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
  • Patent number: 4806676
    Abstract: A process for preparing an aromatic carboxylic ester and an alkyl iodide by carbonylating an aromatic iodide in the presence of an ether, a catalytic amount of a transition metal and a strong acid promoter.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: February 21, 1989
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule
  • Patent number: 4803296
    Abstract: A process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and an iridium catalyst.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: February 7, 1989
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
  • Patent number: 4790963
    Abstract: A process for producing an ester is disclosed comprising contacting a gaseous reactant containing at least one organic hydroxy compound and a mixture of carbon monoxide and hydrogen with an ester synthesis catalyst of the formulaM.sub.a A.sub.b RuCu.sub.c N.sub.z O.sub.xwhereinM is selected from the group consisting of Ce, Cr, Fe, Mn and mixtures thereof,A is an alkali metal, alkaline earth metal or mixture thereof,a is from 0 to about 1,b is from 0.002 to about 10,c is from 0.2 to about 20,z is from 0 to about 196 by weight,x is the number of oxygens needed to fulfill the valence requirements of the other elements.The organic hydroxy compound can be provided separately or formed by contacting a mixture of carbon monoxide and hydrogen with an alcohol synthesis catalyst at an elevated temperature and pressure. The alcohol synthesis catalyst and ester synthesis catalyst can be in tandem or mixed.
    Type: Grant
    Filed: August 20, 1984
    Date of Patent: December 13, 1988
    Assignee: The Standard Oil Company
    Inventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
  • Patent number: 4780563
    Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and a palladium catalyst.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: October 25, 1988
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
  • Patent number: 4778918
    Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and a rhodium catalyst.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: October 18, 1988
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
  • Patent number: 4778917
    Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and a ruthunium catalyst.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: October 18, 1988
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
  • 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: 4739107
    Abstract: Process for the preparation of dicarboxylate esters by reacting an optionally substituted ethylenically unsaturated hydrocarbon having two carbon atoms less than said dicarboxylic acid, CO and an alcohol in the presence of a Group VIII noble metal or a compound thereof, a quinone and optionally, a redox agent and molecular oxygen.
    Type: Grant
    Filed: January 12, 1987
    Date of Patent: April 19, 1988
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4733006
    Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) and iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases and unreacted olefin, alcohol or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the carbon monoxide deficient zones of the system of a catalyst stabilizer which is a germanium (IV) compound, an alkali metal compound, and mixtures thereof.
    Type: Grant
    Filed: August 18, 1983
    Date of Patent: March 22, 1988
    Assignee: Monsanto Company
    Inventors: Thomas C. Singleton, Frank E. Paulik
  • Patent number: 4691047
    Abstract: A process for the carbonylation of a conjugated diene with CO and an alcohol or water in the presence of an aprotic solvent is carried out in the presence of a dissolved catalytic system prepared by combining a Pd(II) compound, at least 5 mol of a triarylphosphine per gram atom of Pd and at least 1 mol of HC1 per gram atom of trivalent P.
    Type: Grant
    Filed: March 26, 1986
    Date of Patent: September 1, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4681707
    Abstract: Carboxylic acid esters are produced by reacting an unsaturated hydrocarbon, for example an olefin or an alkyne, with carbon monoxide and an alcohol in the presence of a protonic acid and as catalyst (a) at least one of the metals palladium, rhodium, ruthenium, iridium and cobalt, and (b) copper. In a modification of the invention carboxylic acids are produced by omitting the alcohol reactant and replacing it with water in an amount up to 8 mole equivalents based on the unsaturated hydrocarbon and a solvent other than an alochol, for example tetrahydrofuran.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: July 21, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, Bertrand Despeyroux, David J. H. Smith, James B. Woell
  • Patent number: 4654436
    Abstract: This invention relates to a novel carbonylation process for the production of aromatic carboxylic acids or esters of aromatic. More particularly, this invention relates to a process for the carbonylation of aromatic iodides or bromides with carbon monoxide in the presence of a palladium catalyst promoted with a Group VIB carbonyl and in the presence of an alcohol or water in a base reaction medium having a pKa greater than about 8. When the alcohol is used the product is the ester. When water is used the product is the carboxylic acid.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: March 31, 1987
    Assignee: Eastman Kodak Company
    Inventors: Donald W. Lane, Thomas H. Larkins, Jr., Mark Rule
  • Patent number: 4642371
    Abstract: Preparation of a diester of a dicarboxylic acid by reacting an unsaturated hydrocarbon having two carbon atoms less than the dicarboxylic acid, carbon monoxide and a nitrite ester with a solvent in the presence of a catalyst system formed by combining (1) a Group VIII noble metal compound and (2) a vanadium salt and/or a titanium salt.
    Type: Grant
    Filed: May 14, 1986
    Date of Patent: February 10, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4625049
    Abstract: A process for the preparation of carboxylic acids, alcohols, aldehydes or the secondary products thereof which comprises reacting an alcohol having from one to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising nickel in admixture with a co-catalyst selected from the elements of Groups V-B, VI-B and the Actinide series of the Periodic Table.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: November 25, 1986
    Assignee: Chevron Research Company
    Inventor: Steven P. Current
  • Patent number: 4585889
    Abstract: The present invention provides a process for the preparation of monoesters of dicarboxylic acids by the carbonylation of carboxyphenyl-triarylphosphonium salts. The carboxyphenyl-triarylphosphonium salts are reacted with carbon monoxide and an alcohol in a base reaction medium having a pK.sub.b greater than about 8.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: April 29, 1986
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, James R. Overton, David D. Cornell
  • Patent number: 4537970
    Abstract: This invention relates to the preparation of esters or salts of aromatic or etheroaromatic acids having formula Y--Ar--CO--OR (I), where:Ar represents an aromatic group constituted by one or more benzene rings, optionally condensed, or an etheroaromatic nucleus optionally condensed with one or more benzene rings;Y represents from zero to more substituents, equal or different, chosen among a halogen; an alkyl group having up to 6 carbon atoms; an alkoxy group having up to 5 carbon atoms; an ester group --COOR', where R' contains up to 5 carbon atoms; a hydroxyl group; a phenyloxy group, optionally substituted with groups inert under reaction conditions; a trifluoromethyl group; a nitrile group; an amidic group (--CONH.sub.2); an acetamidic group (--NH--CO--CH.sub.3); or an acyl group --CO--R", where R" represents a hydrocarbon group having up to 8 carbon atoms;R represents an alkyl group R.sub.1 having up to 5 carbon atoms or an alkali metal or alkaline earth metal M.
    Type: Grant
    Filed: December 12, 1983
    Date of Patent: August 27, 1985
    Assignee: Montedison S.p.A.
    Inventors: Marco Foa, Franco Francalanci, Andrea Gardano, Elena Bencini
  • Patent number: 4450285
    Abstract: .beta.,.gamma.-Unsaturated esters are prepared by the reaction of the corresponding .beta.,.gamma.-unsaturated carbonate with carbon monoxide in the presence of a group VIII metal catalyst.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: May 22, 1984
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Daniel J. Murray
  • Patent number: 4435575
    Abstract: A process is herein described for preparing carboxylated organic compounds (acids, esters, alkaline salts) of formula ##STR1## wherein R is a hydrocarbyl group having up to 11 carbon atoms (an aliphatic, alicyclic, aryl- or heteroarylalkyl group), also substituted, in its turn, by groups inert under the reaction conditions (alkyl, aryl, etheric, thioetheric, halogen, nitrile, ester, amide, ketonic groups), and R' is a hydrogen atom or an alkyl C.sub.1 -C.sub.8 group, by reaction of carbon monoxide with the corresponding hydrocarbyl halides, having the halogen bound to a non-tertiary carbon atom, in the presence of catalysts which are salts of cobalt hydrocarbonyl, or precursors thereof, in a hydro-alcoholic or alcoholic solvent and in the presence of bases.The process is characterized in that the catalytic system composed by the salt of cobalt hydrocarbonyl is supported on an anion exchange resin.
    Type: Grant
    Filed: June 30, 1981
    Date of Patent: March 6, 1984
    Assignee: Montedison S.p.A.
    Inventors: Gianfranco Cainelli, Marco Foa', Achille U. Ronchi, Andrea Gardano
  • Patent number: 4433165
    Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer component selected from N,N,N',N'-tetramethyl-o-phenylenediamine and 2,3'-dipyridyl.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: February 21, 1984
    Assignee: Monsanto Company
    Inventor: Thomas C. Singleton
  • Patent number: 4433166
    Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system containing a rhodium component and an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer which is a tin component which may be tin or a tin compound.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: February 21, 1984
    Assignee: Monsanto Company
    Inventors: Thomas C. Singleton, Frank E. Paulik