Of Olefins Patents (Class 560/233)
-
Patent number: 11773049Abstract: Ru-catalysed domino hydroformylation/hydrogenation/esterification using phosphine ligands.Type: GrantFiled: November 19, 2021Date of Patent: October 3, 2023Assignee: EVONIK OPERATIONS GMBHInventors: Peter Kucmierczyk, Robert Franke, Matthias Beller, Ricarda Dühren, Ralf Jackstell
-
Patent number: 11542221Abstract: The present invention relates to the use of an ?,?-disubstituted carboxylic acid ester of the general formula (I) wherein the variables are as defined in the claims and the description, or of mixtures of two or more of these ?,?-disubstituted carboxylic acid esters or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ?,?-disubstituted carboxylic acid ester of the general formula (I) or a mixture of two or more of said ?,?-disubstituted carboxylic acid esters or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific mixtures of ?,?-disubstituted carboxylic acid esters of the general formula (I).Type: GrantFiled: July 19, 2019Date of Patent: January 3, 2023Assignee: BASF SEInventors: Manuel Danz, Ralf Pelzer, Miriam Bru Roig, Florian Garlichs
-
Patent number: 8969613Abstract: A system and method for removing acetaldehyde from an acetic acid system, including providing a solution from the acetic acid system, the stream having methyl iodide and acetaldehyde, and contacting the solution with an ion-exchange resin and/or liquid catalyst.Type: GrantFiled: October 31, 2012Date of Patent: March 3, 2015Assignee: LyondellBasell Acetyls, LLCInventors: Noel C. Hallinan, Brian A. Salisbury
-
Publication number: 20140303387Abstract: The invention relates to a process for the manufacture of ?,?-branched carboxylic acids vinyl esters comprising the following steps: isomerising and converting an olefin feed with CO and water under Koch reaction conditions to make an acid with a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, wherein a blocking isomer has always a tertiary carbon atom in alpha position of the carboxylic acid and in the beta position of the carboxylic acid, whereas a non-blocking isomer has primary carbon atoms in the beta position of the carboxylic acid converting the resulting acid into a vinyl ester.Type: ApplicationFiled: April 3, 2012Publication date: October 9, 2014Applicant: Momentive Specialty Chemicals Inc.Inventor: Denis Heymans
-
Patent number: 8815992Abstract: Tetraesters of a C4-C5 aliphatic tetracarboxylic acid and OXO-alcohols and plasticized compositions containing said tetraesters are provided.Type: GrantFiled: April 13, 2011Date of Patent: August 26, 2014Assignee: ExxonMobil Research and Engineering CompanyInventors: Lisa Saunders Baugh, Enock Berluche, Karla Schall Colle, Manika Varma-Nair, Ramzi Yanni Saleh, Jon Edmond Randolph Stanat, Stephen Zushma, Victor DeFlorio
-
Patent number: 8785678Abstract: A continuous process for carbonylation of ethylene in a liquid phase using carbon monoxide, a co-reactant and a suitable catalyst system, including: (i) forming a liquid phase comprising the co-reactant and a suitable catalyst system obtainable by combining: (a) a group VIII metal/compound; (b) a ligand of general formula (I) and c) optionally, a source of anions; wherein Q1 is optionally phosphorous; (ii) forming a gaseous phase in contact with the liquid phase by providing at least an ethylene gas input feed stream and a carbon monoxide gas input feed stream wherein the ethylene:CO molar ratio entering the liquid phase from the input feed streams is greater than 2:1; (iii) reacting ethylene with carbon monoxide in the presence of the co-reactant, and of the suitable catalyst system in the liquid phase; wherein the ethylene:CO gas molar ratio in the gaseous phase is between 20:1 and 1000:1 or wherein the molar ratio of ethylene:CO in the liquid phase is greater than 10:1.Type: GrantFiled: December 15, 2010Date of Patent: July 22, 2014Assignee: Lucite International UK LimitedInventors: Eastham Graham Ronald, Neil Tindale
-
Patent number: 8686183Abstract: The invention provides a method for the hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylation or thiocarbonylation of an unsaturated molecule. The method includes a hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylationor thiocarbonylation reaction on the unsaturated molecule in which a complex including a ligand comprising a [n,n?] cyclophane comprising two non-fused monocyclic aromatic rings bridged by two linear and aliphatic linkages, in which each of the non-fused monocyclic aromatic rings is substituted with a phosphorus atom-containing substituent, is used to catalyse the reaction.Type: GrantFiled: September 10, 2010Date of Patent: April 1, 2014Assignee: University Court Of The University of St AndrewsInventors: Matthew Lee Clarke, Tina Marie Konrad
-
Patent number: 8604236Abstract: A continuous carbonylation process for high turnover carbonylation, and a carbonylation reaction medium and product stream thereof. The process comprises carbonylating an ethlenically unsaturated compound with carbon monoxide in the presence of a source of hydroxyl groups and a catalyst system. The catalyst system comprising: (a) a bidentate phosphine, arsine or stibine ligand; and (b) a catalytic metal selected from a group VIB or group VIIIB metal or a compound thereof. The catalytically active concentration of said catalytic metal, measured as the ACCF (product Kg·hr?1·Dm?3), is maintained at less than 0.5.Type: GrantFiled: August 4, 2006Date of Patent: December 10, 2013Assignee: Lucite International UK LimitedInventors: Ronald Graham Eastham, Neil Tindale
-
Publication number: 20110137059Abstract: A novel bidentate catalytic ligand of general formula (I) is described. R represents a hydrocarbyl aromatic structure having at least one aromatic ring to which Q1 and Q2 are each linked, via the respective linking group, if present, on available adjacent atoms of the at least one aromatic ring. The groups X3 and X4 represent radicals joined via tertiary carbon atoms to the respective atom Q1 and the groups X1 and X2 represent radicals joined via primary, or substituted aromatic ring carbon atom(s) to the respective atom Q2. A and B represent an optional lower alkylene linking group. Q1 and Q2 each represent phosphorus, arsenic or antimony. A process for the carbonylation of ethylenically unsaturated compounds comprising reacting the compound with carbon monoxide in the presence of a source of hydroxyl groups, optionally, a source of anions and catalyst system obtainable by combining a metal of Group 8, 9 or 10 or a compound thereof and the bidentate ligand of general formula (I) is also described.Type: ApplicationFiled: July 2, 2009Publication date: June 9, 2011Applicant: LUCITE INTERNATIONAL UK LIMITEDInventors: Graham Ronald Eastham, Mark Waugh, Paul Pringle, Tamara Fanjul Solares
-
Publication number: 20100197958Abstract: A process for the carbonylation of an ethylenically unsaturated compound comprising the step of reacting said compound with carbon monoxide in the presence of a co-5 reactant having a mobile hydrogen atom and a catalyst system is described. The catalyst system is obtainable by combining: (a) a metal of Group 8, 9 or 10 or a suitable compound thereof; (b) a ligand of general formula (I): and c) optionally, a source of anions. The invention is characterised in that the catalyst system includes an enhancer compound comprising an aromatic ring or ring system substituted by at least one hydroxyl group wherein the hydroxyl group pKa at 25° C. is greater than 3.0 and less than 9.1, the said enhancer compound excluding 3-quinolinol.Type: ApplicationFiled: July 8, 2008Publication date: August 5, 2010Applicant: LUCITE INTERNATIONAL UK LIMITEDInventors: Graham Ronald Eastham, Philip Ian Richards
-
Patent number: 7767770Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source with a catalyst comprising synthetic cryptomelane or octahedral molecular sieve. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.Type: GrantFiled: September 17, 2009Date of Patent: August 3, 2010Assignee: Rohm and Haas CompanyInventors: Scott Han, Daniel J. Martenak, Lei Jin, Steven Lawrence Suib
-
Publication number: 20100087615Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source with a catalyst comprising synthetic cryptomelane or octahedral molecular sieve. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.Type: ApplicationFiled: September 17, 2009Publication date: April 8, 2010Inventors: Scott Han, Daniel J. Martenak, Lei Jin, Steven Lawrence Suib
-
Publication number: 20090048411Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene and carbon monoxide. A method for producing an alkyl propionate by steps of: (a) contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene; (b) contacting an alcohol, ethylene and carbon monoxide with an ethylene carbonylation catalyst to produce the alkyl propionate; and (c) separating the alkyl propionate from byproducts and starting materials. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.Type: ApplicationFiled: August 5, 2008Publication date: February 19, 2009Inventors: Abraham Benderly, Scott Han, Mark Anthony Silvano, Donald Lee Zolotorofe
-
Patent number: 7208635Abstract: The invention relates to a hydroformylation process in which at least one olefin having from 2 to 6 carbon atoms is reacted continuously with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst in a reaction zone in which a liquid phase is present and a stream S) is taken from the liquid phase, heat is removed from this stream and the stream is subsequently returned to the reaction zone without removal of a material component.Type: GrantFiled: January 16, 2003Date of Patent: April 24, 2007Assignee: BASF AktiengesellschaftInventors: Wolfgang Richter, Rolf Müller, Roland Krokoszinski
-
Patent number: 7005537Abstract: Disclosed is a process for the production of esters. In particular, the process includes contacting an olefin or an ether with carbon monoxide and an acid composition comprising BF3.2CH3OH to from a product composition, adding an alcohol to the product composition, and separating the BF3.2CH3OH from the ester. The separated BF3.2CH3OH may then be recycled to the reaction unit.Type: GrantFiled: December 26, 2000Date of Patent: February 28, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Edmund J. Mozeleski, Carl R. Beck, Kirk C. Nadler, Richard H. Schlosberg
-
Patent number: 6998026Abstract: A tert-C4–C8-alkyl (meth)acrylate is prepared by reacting (meth)acrylic acid with an olefin of the formula where R1 and R2, which may be identical or different, are methyl or ethyl and R3 is H, methyl or ethyl, in homogeneous phase in the presence of an acidic catalyst and isolating the tert-C4–C8-alkyl (meth)acrylate from the reaction mixture, by a process in which the catalyst is separated off as residue by a two-stage distillation of the reaction mixture and the tert-C4–C8-alkyl (meth)acrylate is isolated from the distillates. The novel process makes it possible to use acetic acid-containing (meth)acrylic acid. The danger of cleavage of the ester and of polymerization of (meth)acrylic compounds is reduced.Type: GrantFiled: July 27, 2001Date of Patent: February 14, 2006Assignee: BASF AktiengesellschaftInventors: Ruprecht Kroker, Gerhard Nestler, Werner Schmitt, Winfried Schumm
-
Patent number: 6984668Abstract: A liquid-phase chemical reaction medium comprises one or more reactants, optionally in the presence of a reaction product(s) and one or more solvents, diluents or other form of liquid carrier, a catalyst system comprising at least a metal or metal compound and optionally further compounds such as ligands or complexing agents; characterized in that the reaction medium further comprises a polymeric dispersant dissolved in said liquid carrier, said polymeric dispersant being capable of stabilizing a colloidal suspension of particles of said metal or metal compound within the liquid carrier. The presence of the polymeric dispersant enables metal formed by catalyst deactivation to be more easily recovered and recycled. Preferably, the polymeric dispersant has sufficiently acidic or basic functionality to stabilize the colloidal suspension of said metal or metal compound.Type: GrantFiled: August 2, 2000Date of Patent: January 10, 2006Assignee: Lucite International UK LimitedInventors: Graham Ronald Eastham, Raymond Anthony Hadden, David William Johnson
-
Patent number: 6919474Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.Type: GrantFiled: March 31, 2003Date of Patent: July 19, 2005Assignee: ExxonMobil Chemical Patents Inc.Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
-
Patent number: 6756506Abstract: The tert-butyl ester of an aliphatic C1-C4-carboxylic acid is prepared by reacting the carboxylic acid with isobutene in the liquid phase in the presence of an acidic catalyst by a continuous process in which the reaction is carried out in a reactor divided into a plurality of sections, the carboxylic acid, the isoolefin and the catalyst are fed into the first section of the reactor, the reaction mixture obtained is removed from the last section of the reactor and the ester is isolated therefrom, the reaction temperature in the reactor being controlled so that it is from 10 to 40° C. and is highest in the first section of the reactor. The novel process permits the technically simple, economical and environmentally friendly preparation of tertiary butyl esters of saturated and unsaturated C1-C4-carboxylic acids.Type: GrantFiled: January 27, 2003Date of Patent: June 29, 2004Assignee: BASF AktiengesellschaftInventors: Ruprecht Kroker, Gerhard Nestler, Werner Schmitt, Winfried Schumm
-
Patent number: 6737542Abstract: The present invention relates to a process for the carbonylation of conjugated dienes, whereby a conjugated diene is reacted with carbon monoxide and a hydroxyl group containing compound in the presence of a catalyst system including: (a) a source of palladium cations, (b) a phosphorus-containing ligand, (c) a source of anions, wherein the phosphorus-containing ligand is a ligand having the general formula (I): X1—R—X2 wherein X1 and X2 represent a substituted or non-substituted cyclic group with at least 5 ring atoms, of which one is a phosphorus atom, and R represents a bivalent organic bridging group, connecting both phosphorus atoms, containing from 1 to 4 atoms in the bridge, whereby the carbonylation process can be performed batch wise, semi-continuously or continuously.Type: GrantFiled: September 20, 2001Date of Patent: May 18, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
-
Patent number: 6706912Abstract: Process for the carbonylation of ethylenically unsaturated compounds having 3 or more carbon atoms by reaction with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system. The catalyst system includes (a) a source of palladium cations; (b) a bidentate diphosphine of formula I, R1R2>P—R3—R—R4—P<R5R6 (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. The process is carried out in the presence of an aprotic solvent.Type: GrantFiled: March 13, 2001Date of Patent: March 16, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
-
Patent number: 6646159Abstract: Long chain alcohols and acids or other similar oxygenates such as esters are produced from paraffins of similar carbon number by a process comprising paraffin dehydrogenation, carbonylation, and separation. Preferably a mixture of paraffins extending over several carbon numbers and recovered from a kerosene fraction is processed, and unconverted paraffins are recycled to a dehydrogenation zone. Alternative reaction zone configurations, catalyst systems and product recovery methods are disclosed.Type: GrantFiled: December 21, 2000Date of Patent: November 11, 2003Assignee: UOP LLCInventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
-
Patent number: 6639091Abstract: Bidentate ligand of formula II, R1R2M1—R—M2R3R4 (II) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent tertiary alkyl groups, or R1 and R2 together and/or R3 and R4 together represent an optionally substituted bivalent cycloaliphatic group whereby the two free valencies are linked to M1 or M2, and R represents a bivalent aliphatic bridging group containing from 2 to 6 atoms in the bridge, which is substituted with two or more substituents. A catalyst system comprising: a) a source of group VIII metal cations; b) a source of such a bidentate ligand; and c) a source of anions, and use of such a catalyst system in a process for the carbonylation of optionally substituted ethylenically or acetylenically unsaturated compounds by reaction with carbon monoxide and a coreactant is provided.Type: GrantFiled: May 17, 2001Date of Patent: October 28, 2003Assignee: Shell Oil CompanyInventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
-
Patent number: 6570040Abstract: The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).Type: GrantFiled: March 16, 2001Date of Patent: May 27, 2003Assignee: The Regents of the University of CaliforniaInventors: Eliana Saxon, Carolyn Bertozzi
-
Patent number: 6541660Abstract: A process is proposed for preparing C5 acetate for Vitamin A synthesis by hydroformylation of 3,4-diacetoxybut-1-ene (3,4-DABE), according to which a 3,4-DABE is used which is obtained by acetoxylation of 1,3-butadiene with acetic acid and air in the presence of a catalyst and removing by distillation the 3,4-DABE formed in this case as by-product.Type: GrantFiled: March 27, 2002Date of Patent: April 1, 2003Assignee: BASF AktiengesellschaftInventors: Udo Rheude, Maximilian Vicari, Werner Aquila, Günter Wegner, Jörg Niekerken
-
Patent number: 6521801Abstract: A process for preparing an 1,3-alkanediol through carbonylation of an epoxide derivative includes the steps of (a) reacting an epoxide derivative with alcohol and carbon monoxide in a solvent at a temperature from about 30 to about 150° C. and at a pressure from about 50 to about 3000 psig in the presence of a catalyst system including an effective amount of a cobalt catalyst and an effective amount of a promoter to afford a reaction mixture including a 3-hydroxyester or derivative thereof in an amount of from 2 to about 95% by weight, (b) separating the reaction product and solvent from the catalyst and promoter, (c) reacting said reaction product and solvent with hydrogen at a temperature from about 30 to about 350° C. and at a pressure from about 50 to about 5000 psig in the presence of a catalyst system for hydrogenation to prepare a hydrogenation product mixture including a 1,3-alkanediol, and (d) recovering the 1,3-alkanediol from the hydrogenation product mixture.Type: GrantFiled: December 7, 2001Date of Patent: February 18, 2003Assignee: Samsung Electronics Co., Ltd.Inventors: Byeong-No Lee, Byung-Soon Chen
-
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
-
Patent number: 6489506Abstract: A process for the liquid-phase carbonylation of ethylene, according to the equation C2H4+CO+ROH→C2H5CO2R, in the presence of a catalyst system comprising a Group VIII metal or compound thereof, a phosphine ligand and a source of anions, and in the presence of water or a source of organic hydroxyl groups, is carried out in conditions in which the molar ratio of ethylene to carbon monoxide in the gaseous phase of the reactor is greater than 1:1. The higher ratios of ethylene to carbon monoxide are beneficial in increasing the turnover number of the catalyst system.Type: GrantFiled: June 21, 2001Date of Patent: December 3, 2002Assignee: Lucite International UK LimitedInventors: Jean Margaret Pearson, Raymond Anthony Hadden
-
Patent number: 6476255Abstract: A process for the manufacture of an alkyl ester of an aliphatic carboxylic acid comprises the steps of supplying a first feed stream comprising carbon monoxide and an alkene of formula CnH2n to a reactor, supplying a second feed stream comprising an alkyl alcohol, having a formula R—OH where R is an optionally substituted alkyl group, to the reactor, and reacting together said first and second feed streams in the reactor in the presence of a carbonylation catalyst, which catalyses the carbonylation reaction between carbon monoxide and the alkene, to form a product comprising an alkyl alkanoate having the formula CnH2n+1COOR, such that the ratio of alkyl alcohol to alkyl alkanoate present in the reactor is greater than the ratio of alkyl alcohol to alkyl alkanoate present in an azeotropic mixture of the alkyl alcohol and alkyl alkanoate. The process is particularly useful for the manufacture of methyl propionate by the methoxycarbonylation of ethylene.Type: GrantFiled: November 1, 2000Date of Patent: November 5, 2002Assignee: Lucite International UK LimitedInventors: Raymond A Hadden, Jean M Pearson
-
Patent number: 6452043Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.Type: GrantFiled: April 5, 2000Date of Patent: September 17, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
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
-
Publication number: 20010041808Abstract: Disclosed is a process for the production of esters. In particular, the process includes contacting an olefin or an ether with carbon monoxide and an acid composition comprising BF3.2CH3OH to from a product composition, adding an alcohol to the product composition, and separating the BF3.2CH3OH from the ester. The separated BF3.2CH3OH may then be recycled to the reaction unit.Type: ApplicationFiled: December 26, 2000Publication date: November 15, 2001Inventors: Edmund J. Mozeleski, Carl R. Beck, Kirk C. Nadler, Richard H. Schlosberg
-
Patent number: 6294687Abstract: The present invention discloses this invention relates to a process for the conversion of olefinically unsaturated compounds to corresponding carboxylic acids and their esters of formula III wherein R1, R2, R3 and R4 may independently be hydrogen, alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, R and R5 may be H and COOR′ or vice versa wherein R′ may be H in the case of acids and may be alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, in the case of esters, wherein said conversion is carried out in the presence of a transition metal complex catalyst of the formula.Type: GrantFiled: December 30, 1999Date of Patent: September 25, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vitthal Chaudhari, A. Seayad, Jayasree Seayad
-
Patent number: 6284919Abstract: A process for the liquid-phase carbonylation of ethylene, according to the equation C2H4+CO+ROH→C2H5CO2R, in the presence of a catalyst system comprising a Group VIII metal or compound thereof, a phosphine ligand and a source of anions, and in the presence of water or a source of organic hydroxyl groups, is carried out in conditions in which the molar ratio of ethylene to carbon monoxide in the gaseous phase of the reactor is greater than 1:1. The higher ratios of ethylene to carbon monoxide are beneficial in increasing the turnover number of the catalyst system.Type: GrantFiled: September 15, 1999Date of Patent: September 4, 2001Assignee: Imperial Chemical Industries PLCInventors: Jean Margaret Pearson, Raymond Anthony Hadden
-
Patent number: 6274096Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The plant is retrofitted to feed carbon dioxide into a reformer to which natural gas and steam (water) are fed. Syngas is formed in the reformer wherein both the natural gas and the carbon dioxide are reformed to produce syngas with a large proportion of carbon monoxide relative to reforming without added carbon dioxide. The syngas is split into a first part and a second part. The first syngas part is converted to methanol in a conventional methanol synthesis loop that is operated at about half of the design capacity of the original plant. The second syngas part is processed to separate out carbon dioxide and carbon monoxide, and the separated carbon dioxide is fed back into the feed to the reformer to enhance carbon monoxide formation. The separated carbon monoxide is then reacted with the methanol to produce acetic acid or an acetic acid precursor by a conventional process.Type: GrantFiled: November 1, 1999Date of Patent: August 14, 2001Assignee: Acetex (Cyprus) LimitedInventors: Daniel Marcel Thiebaut, Kenneth Ebenes Vidalin
-
Patent number: 6049011Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.Type: GrantFiled: October 15, 1997Date of Patent: April 11, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
-
Patent number: 6037506Abstract: A process is presented in which ethylenically unsaturated compounds are reacted with carbon monoxide and hydrogen to form reaction products. The reactants are contacted in the presence of a catalyst system made by combining: (a) a source of palladium, platinum, or nickel,(b) a bidentate ligand of the formula R.sub.1 R.sub.2 M.sub.1 RM.sub.2 R.sub.3 R.sub.4 in which M.sub.1 and M.sub.2 independently may be phosphorus, arsenic, or antimony atoms, R is a bivalent organic bridging group and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are unsubstituted or substituted aliphatic groups, wherein one or more combinations of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 form a bivalent cyclic group, and(c) an acid,and a promoter which is a formate, formic acid, or formic acid forming reagent provided that it is not an orthoformate.Type: GrantFiled: September 18, 1998Date of Patent: March 14, 2000Assignee: Shell Oil CompanyInventor: Cornelius Mark Bolinger
-
Patent number: 6011171Abstract: The present invention provides a process for synthesizing tertiary carboxylic acids or the esters thereof having one or two more carbon atoms than the raw material has, comprising reacting in a strong acid (e.g., sulfuric acid, sulfuric acid-phosphoric acid, hydrogen fluoride, fluorosulfuric acid, boron trifluoride.water complex and trifluoromethanesulfonic acid) a raw material compound (i.e., olefin, alcohol, diene, diol or saturated hydrocarbon) with carbon monoxide in the presence of a specific metal carbonyl catalyst (i.e., platinum carbonyl catalyst, palladium carbonyl catalyst and gold dicarbonyl catalyst).The metal carbonyl catalyst is formed by reacting in a strong acid at least one specific metal compounds (e.g., platinum compound such as platinum (II, IV) oxide, platinum (II, IV) hydroxide, a platinum powder, etc.; palladium compound such as palladium (II, III, IV) oxide, palladium (II) hydroxide, palladium (II) sulfate, palladium (II) carboxylate, a palladium powder, etc.Type: GrantFiled: November 4, 1997Date of Patent: January 4, 2000Assignee: Jiro Hiraishi, Director-General, Agency of Industrial Science and TechnologyInventors: Qiang Xu, Yoshie Souma
-
Patent number: 5936117Abstract: Disclosed is a process for the preparation of aliphatic carbonyl compounds selected from aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by the carbonylation of olefins in the presence of a catalyst system comprising (1) a primary component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a secondary component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic. The process constitutes and improvement over known processes since it can be carried out at moderate carbonylation conditions without the necessity of using an expensive noble metal catalyst, volatile, toxic materials such as nickel tetracarbonyl, formic acid or a formate ester.Type: GrantFiled: July 28, 1995Date of Patent: August 10, 1999Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Elizabeth MacGowan West, Horace Lawrence Browning, Jr., George Geiger Mayfield
-
Patent number: 5932761Abstract: It is provided a process for industrially advantageously producing a branched aldehyde represented by the formula; ##STR1## ?wherein Y represents an acyl group of two or more carbon atoms; and X represents an acyloxymethyl group represented by --CH.sub.2 OY' (where Y' represents an acyl group of two or more carbon atoms), cyano group or an alkoxycarbonyl group! which is useful as an intermediate for pharmaceuticals and agricultural chemicals, comprising subjecting an olefinic compound represented by the following formula; ##STR2## (wherein Y and X are the same as defined above), to the reaction with hydrogen and carbon monoxide in the presence of a rhodium compound and a tertiary organic phosphorus compound with an electronic parameter (.upsilon.-value) of 2080 to 2090 cm.sup.-1 or with a steric parameter (.theta.-value) of 150 to 180.degree..Type: GrantFiled: March 23, 1998Date of Patent: August 3, 1999Assignee: Kuraray Co., Ltd.Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
-
Patent number: 5834622Abstract: A process for the carbonylation of a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof which process comprises contacting said carbonylatable reactant and/or a reactive derivative thereof with carbon monoxide in a liquid reaction composition in a carbonylation reactor characterized in that the liquid reaction composition comprises: (a) an iridium catalyst, (b) a halide, (c) at least a finite concentration of water, (d) a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof and (e) as promoter, at least one of ruthenium and osmium.Type: GrantFiled: July 5, 1996Date of Patent: November 10, 1998Assignee: BP Chemicals LimitedInventor: John Glenn Sunley
-
Patent number: 5760284Abstract: Disclosed is an improved catalyst system and process for preparing aliphatic carbonyl compounds such as aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by carbonylating olefins in the presence of a catalyst system comprising (1) a first component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a second component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic, and (3) as a third component, a polar, aprotic solvent. The process employing the improved catalyst system is carried out under carbonylating conditions of pressure and temperature discussed herein.Type: GrantFiled: April 10, 1997Date of Patent: June 2, 1998Assignee: Eastman Chemical CompanyInventor: Joseph Robert Zoeller
-
Patent number: 5705683Abstract: The process for carbonylating olefins with carbon monoxide in the presence of water, an alcohol or a carboxylic acid and a halogen-free catalyst comprises using a catalyst comprising nickel or a nickel compound and at least one of the metals of the group consisting of chromium, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver and gold, or a compound of these metals.Type: GrantFiled: January 13, 1997Date of Patent: January 6, 1998Assignee: BASF AktiengesellschaftInventors: Ferdinand Lippert, Arthur Hohn, Martin Schafer, Leopold Hupfer
-
Patent number: 5698722Abstract: A Koch functionalized product which is the reaction product of at least one polymer having a number average molecular weight of at least 500 and at least ethylenic double bond per polymer chain, with carbon monoxide and a nucleophilic trapping agent. The invention includes functionalized polymer, derivatives thereof and methods of making the same.Type: GrantFiled: June 6, 1995Date of Patent: December 16, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Joseph Victor Cusumano, William Daniel Diana, Jacob Emert, Keith Raymond Gorda, Richard H. Schlosberg, David A. Young, William Bernard Eckstrom, Edris Eileen Manry, Michael John Keenan
-
Patent number: 5679831Abstract: Process for the preparation of a terminal ester by carbonylation of an internally unsaturated organic compound in the presence of an alcohol, carbon monoxide, palladium, an acid with a pK.sub.a of less than 2 (measured at 18.degree. C. in an aqueous solution) and a bidentate organic phosphorus, antimony or arsenic ligand compound having a bridging group, wherein the bridging group comprises a bis(.eta.-cyclopentadienyl) coordination group of a transition metal.Type: GrantFiled: January 5, 1995Date of Patent: October 21, 1997Assignees: DSM N.V., E. I. Du Pont de Nemours and CompanyInventor: Otto E. Sielcken
-
Patent number: 5650536Abstract: A continuous process for functionalizing olefins, especially polymer olefins in a CSTR or pipe reactor. Esters are preferably produced by continuous reaction of the olefin with carbon monoxide and a nucleophilic trapping agent. The liquid-filled pipe reactor operates in plug flow with static mixers and the CSTR is operated in the substantial absence of air at constant liquid level.Type: GrantFiled: June 17, 1994Date of Patent: July 22, 1997Assignee: Exxon Chemical Patents Inc.Inventors: David C. Dankworth, William H. Cross, Joseph V. Cusumano, William D. Diana, William B. Eckstrom, Jacob I. Emert, Keith R. Gorda, Robert M. Koros, Harold W. Margo, Jon E. Stanat
-
Patent number: 5463095Abstract: A process for the production of esters, comprising allowing an olefin, carbon monoxide and an alcohol to react in the presence of hydrogen fluoride, in which the esters can be produced at high yields at a low temperature for a short period of time, the esters can be easily separated from a reaction solution, hydrogen fluoride can be recycled, the esters can be produced at a low cost, a mixture of esters can be easily produced, the kinetic viscosity of the mixture of the esters can be easily adjusted and the coloring of, and an increase in the viscosity of, the esters can be prevented.Type: GrantFiled: June 14, 1994Date of Patent: October 31, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yoshihiro Shiokawa, Tadayoshi Takefumi, Shunichi Matsumoto, Yoshifumi Sato
-
Patent number: 5364957Abstract: The invention relates to a process for the carbonylation of an olefinically or acetylenically unsaturated hydrocarbon compound by reaction with carbon monoxide and a hydroxy compound in the presence of a catalyst system comprising a source of cationic palladium, a source of phosphine and a protonic acid, which reaction is carried out in the presence of a free radical inhibitor.Type: GrantFiled: April 8, 1993Date of Patent: November 15, 1994Assignee: Shell Oil CompanyInventors: Peter Arnoldy, Antoon P. M. Kremers
-
Patent number: 5324856Abstract: Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.Also disclosed is a process for making an .alpha.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
-
Patent number: 5321155Abstract: Cyclohexyladipates are produced by reacting a mixture containing a major amount of benzene and minor amounts of cyclohexene, adipic acid and an acid catalyst.Type: GrantFiled: April 15, 1993Date of Patent: June 14, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: William C. Drinkard, Gerald C. Grunewald