Carbonylation Patents (Class 560/97)
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Patent number: 8703992Abstract: 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 foType: GrantFiled: May 25, 2009Date of Patent: April 22, 2014Assignee: BASF SEInventors: Nina Challand, Ansgar Gereon Altenhoff, Joachim Schmidt-Leithoff, Kathrin Wissel-Stoll, Michael Rack, Joachim Rheinheimer
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Publication number: 20100160632Abstract: 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: ApplicationFiled: May 14, 2008Publication date: June 24, 2010Inventors: Paul Knochel, Stefan Wunderlich
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Patent number: 7098363Abstract: 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: GrantFiled: December 16, 1999Date of Patent: August 29, 2006Assignee: BP Chemicals LimitedInventor: Michael David Jones
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Patent number: 6653502Abstract: 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: GrantFiled: November 9, 2001Date of Patent: November 25, 2003Assignee: Clariant GmbHInventor: Holger Geissler
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Publication number: 20030191339Abstract: 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: ApplicationFiled: March 25, 2003Publication date: October 9, 2003Inventors: Martin Schfer, Michael Slany, Edgar Zeller, Michael Rper, Michael Schulz, G?uuml;nter Grimm
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Patent number: 6521783Abstract: 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: GrantFiled: July 10, 2000Date of Patent: February 18, 2003Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: 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
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Patent number: 6355702Abstract: 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: GrantFiled: February 2, 2000Date of Patent: March 12, 2002Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Kenji Ogino
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Patent number: 6355711Abstract: 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: GrantFiled: March 31, 1999Date of Patent: March 12, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: Allen David Godwin, Dwight McLean Lyman
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Patent number: 6127574Abstract: 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: GrantFiled: June 16, 1998Date of Patent: October 3, 2000Assignee: BP Chemicals LimitedInventors: Mark Julian Howard, Michael David Jones
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Patent number: 5719313Abstract: 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: GrantFiled: March 13, 1996Date of Patent: February 17, 1998Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
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Patent number: 5414109Abstract: 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: GrantFiled: February 18, 1994Date of Patent: May 9, 1995Assignee: Shell Oil CompanyInventors: Eit Drent, Eric Kragtwijk
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Patent number: 5360938Abstract: 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: GrantFiled: July 16, 1992Date of Patent: November 1, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, Gregory T. Whiteker
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Patent number: 5258546Abstract: 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: GrantFiled: November 20, 1992Date of Patent: November 2, 1993Assignee: Shell Oil CompanyInventors: Peter A. Klusener, Hans A. Stil, Fit Drent, Peter Arnoldy
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Patent number: 5245072Abstract: 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: GrantFiled: February 24, 1992Date of Patent: September 14, 1993Assignee: Mobil Oil CorporationInventors: Thomas J. Giacobbe, George A. Ksenic
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Patent number: 5233075Abstract: 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: GrantFiled: October 15, 1991Date of Patent: August 3, 1993Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Andrew J. Matosky
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Patent number: 5189198Abstract: 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: GrantFiled: May 6, 1991Date of Patent: February 23, 1993Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Takashi Kumazawa, Tetsuo Ishibashi, Mitsugu Kanzawa
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Patent number: 5158921Abstract: 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: GrantFiled: February 28, 1990Date of Patent: October 27, 1992Assignee: Shell Oil CompanyInventors: Eit Drent, Petrus H. M. Budzelaar, Willem W. Jager
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Patent number: 5028734Abstract: 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: GrantFiled: January 27, 1989Date of Patent: July 2, 1991Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5003104Abstract: 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: GrantFiled: October 31, 1988Date of Patent: March 26, 1991Assignee: BP Chemicals LimitedInventors: Frank E. Paulik, Arnold Hershman, Walter R. Knox, Robert G. Schultz, James F. Roth
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Patent number: 4990657Abstract: 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: GrantFiled: May 19, 1989Date of Patent: February 5, 1991Assignee: Rhone-Poulenc ChimieInventors: Norbert Bluthe, Robert Perron
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Patent number: 4933467Abstract: 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: GrantFiled: September 11, 1989Date of Patent: June 12, 1990Assignee: Eastman Kodak CompanyInventors: Robert J. Perry, S. R. Turner
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Patent number: 4933468Abstract: 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: GrantFiled: September 11, 1989Date of Patent: June 12, 1990Assignee: Eastman Kodak CompanyInventors: Robert J. Perry, S. Richard Turner
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Patent number: 4933466Abstract: 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: GrantFiled: January 17, 1989Date of Patent: June 12, 1990Assignee: Eastman Kodak CompanyInventors: Robert J. Perry, Sam R. Turner
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Patent number: 4912250Abstract: 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: GrantFiled: February 6, 1989Date of Patent: March 27, 1990Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanny C. Treece
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Patent number: 4904817Abstract: 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: GrantFiled: February 21, 1989Date of Patent: February 27, 1990Assignee: Eastman Kodak CompanyInventor: Guy R. Steinmetz
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Patent number: 4868328Abstract: 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: GrantFiled: November 20, 1987Date of Patent: September 19, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4866200Abstract: 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: GrantFiled: August 4, 1988Date of Patent: September 12, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
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Patent number: 4851564Abstract: 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: GrantFiled: February 22, 1988Date of Patent: July 25, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4847406Abstract: 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: GrantFiled: January 12, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4827018Abstract: 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: GrantFiled: October 22, 1987Date of Patent: May 2, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
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Patent number: 4806676Abstract: 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: GrantFiled: June 20, 1988Date of Patent: February 21, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4803296Abstract: 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: GrantFiled: May 11, 1988Date of Patent: February 7, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4790963Abstract: 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: GrantFiled: August 20, 1984Date of Patent: December 13, 1988Assignee: The Standard Oil CompanyInventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
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Patent number: 4780563Abstract: 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: GrantFiled: October 19, 1987Date of Patent: October 25, 1988Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4778918Abstract: 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: GrantFiled: November 2, 1987Date of Patent: October 18, 1988Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4778917Abstract: 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: GrantFiled: November 2, 1987Date of Patent: October 18, 1988Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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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: 4739107Abstract: 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: GrantFiled: January 12, 1987Date of Patent: April 19, 1988Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4733006Abstract: 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: GrantFiled: August 18, 1983Date of Patent: March 22, 1988Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
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Patent number: 4691047Abstract: 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: GrantFiled: March 26, 1986Date of Patent: September 1, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4681707Abstract: 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: GrantFiled: April 23, 1984Date of Patent: July 21, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, Bertrand Despeyroux, David J. H. Smith, James B. Woell
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Patent number: 4654436Abstract: 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: GrantFiled: July 21, 1986Date of Patent: March 31, 1987Assignee: Eastman Kodak CompanyInventors: Donald W. Lane, Thomas H. Larkins, Jr., Mark Rule
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Patent number: 4642371Abstract: 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: GrantFiled: May 14, 1986Date of Patent: February 10, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4625049Abstract: 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: GrantFiled: June 30, 1982Date of Patent: November 25, 1986Assignee: Chevron Research CompanyInventor: Steven P. Current
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Patent number: 4585889Abstract: 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: GrantFiled: January 28, 1985Date of Patent: April 29, 1986Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, James R. Overton, David D. Cornell
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Patent number: 4537970Abstract: 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: GrantFiled: December 12, 1983Date of Patent: August 27, 1985Assignee: Montedison S.p.A.Inventors: Marco Foa, Franco Francalanci, Andrea Gardano, Elena Bencini
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Patent number: 4450285Abstract: .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: GrantFiled: February 22, 1982Date of Patent: May 22, 1984Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, Daniel J. Murray
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Patent number: 4435575Abstract: 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: GrantFiled: June 30, 1981Date of Patent: March 6, 1984Assignee: Montedison S.p.A.Inventors: Gianfranco Cainelli, Marco Foa', Achille U. Ronchi, Andrea Gardano
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Patent number: 4433165Abstract: 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: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventor: Thomas C. Singleton
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Patent number: 4433166Abstract: 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: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik