Carbon Monoxide Reactant Patents (Class 568/387)
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Patent number: 11555140Abstract: This invention provides a composition comprising I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and II. at least one reaction product between a nitrogen-free sugar alcohol and an aldehyde or ketone, and optionally III. at least one reaction product from III.a) formaldehyde, and III.b) an amine, selected from the group consisting of primary alkyl amines having 1 to 4 carbon atoms, and primary hydroxy alkyl amines having 2 to 4 carbon atoms, and optionally IV. at least one solid suppression agent selected from the group consisting of IV(a). alkali or alkaline earth metal hydroxides IV(b). mono-, di- or tri-hydroxy alkyl, aryl or alkylaryl amines, IV(c). mono-, di- or tri-alkyl, aryl or alkylaryl primary, secondary and tertiary amines or IV(d). multifunctional amines and IV(e). mixtures of compounds of groups IV(a) to IV(c). wherein alkyl is C1 to C15, aryl is C6 to C15 and alkylaryl is C7 to C15.Type: GrantFiled: December 22, 2017Date of Patent: January 17, 2023Assignee: CLARIANT INTERNATIONAL LTDInventors: Antonio Pedro de Oliveira Filho, Aline Yae Kina, Grahame N. Taylor, Fabian Schneider, Julie Murison, Stefan Hauck, Mike Sahl, Matthias Krull, Jonathan James Wylde
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Patent number: 11118097Abstract: This invention provides a composition comprising I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and II. at least one reaction product between a nitrogen-free sugar alcohol and an aldehyde or ketone, and optionally III. at least one reaction product from III.a) formaldehyde, and III.b) an amine, selected from the group consisting of primary alkyl amines having 1 to 4 carbon atoms, and primary hydroxy alkyl amines having 2 to 4 carbon atoms, and optionally IV. at least one solid suppression agent selected from the group consisting of IV(a). alkali or alkaline earth metal hydroxides IV(b). mono-, di- or tri-hydroxy alkyl, aryl or alkylaryl amines, IV(c). mono-, di- or tri-alkyl, aryl or alkylaryl primary, secondary and tertiary amines or IV(d). multifunctional amines and IV(e). mixtures of compounds of groups IV(a) to IV(c). wherein alkyl is C1 to C15, aryl is C6 to C15 and alkylaryl is C7 to C15.Type: GrantFiled: December 22, 2017Date of Patent: September 14, 2021Assignee: Clariant International Ltd.Inventors: Antonio Pedro de Oliveira Filho, Aline Yae Kina, Grahame N. Taylor, Fabian Schneider, Julie Murison, Stefan Hauck, Mike Sahl, Matthias Krull, Jonathan James Wylde
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Publication number: 20150018576Abstract: The invention relates to a method for producing a product mixture (2) by means of the technical hydroformylation of a hydrocarbon stream (1) that contains isobutene, and for separating the product mixture (2) that is obtained, as well as to a device for the claimed method and to the use of a claimed device. The problem addressed thereby is that of providing a method and an associated device that allow the amount of high-boiling substances in the product mixture (2) to be kept as low as possible and thus the yield of the reaction to be increased. The problem is solved by the use of a nano-filtration device (M) for separating the catalyst from the product mixture (2), said device having especially high permeability to 3-methylbutanoic acid.Type: ApplicationFiled: February 11, 2013Publication date: January 15, 2015Applicant: Evonik Degussa GmbHInventors: Goetz Baumgarten, Michael Grass, Alfred Kaizik, Markus Winterberg, Hans-Gerd Lueken, Bart Hamers, Markus Priske, Dirk Fridag, Robert Franke, Dieter Hess
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Patent number: 8859821Abstract: The invention relates to polyketone compounds and the at least partially hydrogenated products thereof, the use of said polyketone compounds and/or the at least partially hydrogenated products thereof as plasticizers, processes of making polyketone compounds and the at least partially hydrogenated products thereof, compositions comprising the polyketone compounds and/or the at least partially hydrogenated products thereof, and to articles formed from products of the invention.Type: GrantFiled: January 6, 2012Date of Patent: October 14, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Allen D. Godwin, Kenneth J. Buturla, Karla S. Colle, Gabor Kiss, Kirk C. Nadler, Abhimanyu O. Patil, Edris Eileen Pike, Ramzi Y. Saleh, Jon E. Stanat, Manika Varma-Nair, Stephen Zushma
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Publication number: 20120108726Abstract: The invention relates to polyketone compounds and the at least partially hydrogenated products thereof, the use of said polyketone compounds and/or the at least partially hydrogenated products thereof as plasticizers, processes of making polyketone compounds and the at least partially hydrogenated products thereof, compositions comprising the polyketone compounds and/or the at least partially hydrogenated products thereof, and to articles formed from products of the invention.Type: ApplicationFiled: January 6, 2012Publication date: May 3, 2012Inventors: Allen D Godwin, Kenneth J. Buturla, Karla S. Colle, Gabor Kiss, Kirk C. Nadler, Abhimanyu O. Patil, Edris Eileen Pike, Ramzi Y. Saleh, Jon E. Stanat, Manika Varma-Nair, Stephen Zushma
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Patent number: 8148579Abstract: Methods are disclosed for forming heptan-4-one, and, optionally, heptan-4-ol, from fermentable sugars. The sugars are fermented using a bacteria or yeast that predominantly forms butyric acid. The butyric acid is subjected to catalytic ketonization conditions to form heptan-4-one, with concomitant loss of water and carbon dioxide. The heptan-4-one can be subjected to catalytic hydrogenation to form heptan-4-ol, an either of these can be included in gasoline compositions. In one aspect, the fermentable sugars are derived from lignocellulosic materials such as wood products, switchgrass, or agricultural wastes, which are delignified to form lignin, cellulose and hemicellulose. The cellulose and hemicellulose can be depolymerized to form glycose and xylose, either or both of which can be fermented by the bacteria.Type: GrantFiled: June 12, 2008Date of Patent: April 3, 2012Assignee: CPS Biofuels, Inc.Inventor: David Bradin
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Patent number: 8115034Abstract: The invention relates to polyketone compounds and the at least partially hydrogenated products thereof, the use of said polyketone compounds and/or the at least partially hydrogenated products thereof as plasticizers, processes of making polyketone compounds and the at least partially hydrogenated products thereof, compositions comprising the polyketone compounds and/or the at least partially hydrogenated products thereof, and to articles formed from products of the invention.Type: GrantFiled: March 28, 2008Date of Patent: February 14, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Allen D. Godwin, Kenneth J. Buturla, Karla S. Colle, Gabor Kiss, Kirk C. Nadler, Abhimanyu O. Patil, Edris Eileen Pike, Ramzi Y. Saleh, Jon E. Stanat, Manika Varma-Nair, Stephen Zushma
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Publication number: 20110269995Abstract: A reactor (1) for preparing phosgene by gas-phase reaction of carbon monoxide and chlorine in the presence of a solid-state catalyst, which is provided in the catalyst tubes (2) of a bundle of catalyst tubes (2) which are arranged parallel to one another in the longitudinal direction of the reactor (1) and are welded at each of their two ends into a tube plate (3), with introduction of the starting materials at the upper end of the catalyst tubes (2) and discharge of the gaseous reaction mixture at the lower end of the catalyst tubes (2), in each case via a cap, and also with introduction and discharge facilities for a liquid heat transfer medium (6) in the intermediate space (4) between the catalyst tubes (2) , where the flow of the heat transfer medium (6) in the space (4) between the catalyst tubes (2) is guided by deflection plates (5), which leave alternating openings (7) free on opposite sides at the interior wall of the reactor, in which openings the deflection plates (5) have cutouts having the shapeType: ApplicationFiled: December 16, 2009Publication date: November 3, 2011Applicant: BASF SEInventors: Gerhard Olbert, Wolfgang Gerlinger, Byoung-Yeon Kim
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Patent number: 7935849Abstract: Saturated aliphatic ketones, e.g. hexahydropseudoionone, may be prepared by hydrogenating an olefinically unsaturated ketone, e.g. pseudoionone in a continuous fixed-bed mode in the absence of a solvent in the presence of a catalyst comprising a noble metal deposited on a carrier.Type: GrantFiled: September 14, 2005Date of Patent: May 3, 2011Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Thomas Kircher, Rolf Kuenzi, Johannes Tschumi
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Publication number: 20110028746Abstract: The present invention relates to a process for preparing aldehydes by reacting an ?,?-unsaturated carboxylic acid or a salt thereof with carbon monoxide and hydrogen in the presence of a catalyst comprising at least one complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one compound of the formula (I), where Pn is pnicogen; W is a divalent bridging group having from 1 to 8 bridge atoms between the flanking bonds; R1 is a functional group capable of forming at least one intermolecular, noncovalent bond with the —X(?O)OH group of the compound of the formula (I); R2, R3 are each in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl or together with the pnicogen atom and together with the groups Y2 and Y3 if present form an optionally fused and optionally substituted 5- to 8-membered heterocycle; a, b and c are each 0 or 1; and Y1,2,3 are each, independently of one another, O, S, NRa or SiRbRc, where Ra,b,c are each H or in each cType: ApplicationFiled: March 25, 2009Publication date: February 3, 2011Applicant: BASF SEInventors: Jens Rudolph, Joachim Schmidt-Leithoff, Rocco Paciello, Bernhard Breit, Thomas Smejkal
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Patent number: 7659431Abstract: Methods and systems for preparing dialkyl ketones are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of carbon monoxide and hydrogen with the olefins (e.g. ethylene) in a liquid solvent. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time.Type: GrantFiled: June 19, 2008Date of Patent: February 9, 2010Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7485739Abstract: A catalyst suitable for carbonylating ethylenically unsaturated compounds comprising a Group VIIIB metal or compound thereof and a metallocene.Type: GrantFiled: September 10, 2003Date of Patent: February 3, 2009Assignee: Lucite International UK Ltd.Inventors: Graham Eastham, Ian Butler, Kevin Fortune
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Publication number: 20080242895Abstract: The invention relates to polyketone compounds and the at least partially hydrogenated products thereof, the use of said polyketone compounds and/or the at least partially hydrogenated products thereof as plasticizers, processes of making polyketone compounds and the at least partially hydrogenated products thereof, compositions comprising the polyketone compounds and/or the at least partially hydrogenated products thereof, and to articles formed from products of the invention.Type: ApplicationFiled: March 28, 2008Publication date: October 2, 2008Inventors: Allen D. Godwin, Kenneth J. Buturla, Karla S. Colle, Gabor Kiss, Kirk C. Nadler, Abhimanyu O. Patil, Edris Eileen Pike, Ramzi Y. Saleh, Jon E. Stanat, Manika Varma-Nair, Stephen Zushma
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Publication number: 20040249218Abstract: Process for preparing 6-methylheptan-2-one, which comprisesType: ApplicationFiled: March 24, 2004Publication date: December 9, 2004Inventors: Klaus-Diether Wiese, Guido Protzmann
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Patent number: 6723882Abstract: Dialkyl ketones are prepared by reductive carbonylation of &agr;-olefins by means of carbon monoxide and hydrogen in the presence of a catalyst system comprising (a) palladium or a palladium compound; (b) a phosphine; (c) a protic acid having a pKa of ≦4.5, measured in aqueous solution at 25° C.; and (d) a solubilizable carboxamide.Type: GrantFiled: July 18, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Michael Slany, Martin Schäfer, Michael Röper
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Patent number: 6359179Abstract: A process for the direct carbonylation of saturated hydrocarbons has been developed. The process involves contacting the saturated hydrocarbons, which contain at least one primary, secondary or tertiary carbon atom, with carbon monoxide in the presence of a solid strong acid catalyst to produce an oxygenated saturated hydrocarbon. In a specific embodiment isobutane is reacted with carbon monoxide using sulfated zirconia as the catalyst to produce methylisopropyl ketone. The oxygenated hydrocarbon can subsequently be hydrogenated to give a reduced oxygenated saturated hydrocarbon. The hydrogenation can also be done simultaneously with the carbonylation, i.e., reductive carbonylation.Type: GrantFiled: December 22, 1999Date of Patent: March 19, 2002Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffrey C. Bricker, Jules Rabo, Ralph D. Gillespie
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Patent number: 6288281Abstract: A process for the carbonylation of saturated hydrocarbons to give an oxygenated saturated hydrocarbon is disclosed and claimed. The process involves using an acidic ionic liquid catalyst to catalyze the carbon monoxide addition to the saturated hydrocarbon at reaction conditions to form an oxygenate. The acidic ionic liquid comprises a Lewis or Bronsted acid in combination with a quaternary nitrogen-containing compound. A specific example is a mixture of aluminum chloride and n-butylpyridinium chloride.Type: GrantFiled: November 16, 2000Date of Patent: September 11, 2001Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffery C. Bricker, Jennifer S. Holmgren, Lyle E. Monson
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Patent number: 5955562Abstract: A alternating aliphatic polyketone polymer is surface derivatized to alter the surface properties of an article without affecting the bulk properties of the polymer it is made from. Derivitization may be done with reducing agents and/or silylating agents. Articles so produced display a range of improved properties including reduced wettability and improved tribological properties such as lubricity and wear resistance.Type: GrantFiled: December 22, 1997Date of Patent: September 21, 1999Assignee: Shell Oil CompanyInventors: Carlton Edwin Ash, Donald Ross Kelsey
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Patent number: 5776865Abstract: Emulsifiable oil, suitable for use as oil phase in oil-based drilling fluids, having one or more ketones with a flashpoint of at least 55.degree. C., in particular oligoketones obtainable by co-oligomerization of carbon monoxide and olefins.Type: GrantFiled: May 17, 1995Date of Patent: July 7, 1998Assignee: Shell Oil CompanyInventors: Maria Manuel De Castro Loureiro Barreto Rosa, Arend Kuindert Van Helden, Herman Mathieu Muijs
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Patent number: 5763672Abstract: Catalyst compositions for preparing polyketones comprising(a) a Group VIII metal compound, containing at least one ligand capable of coordinating to the Group VIII metal, and(b) a boron hydrocarbyl compoundare disclosed, in particular catalyst compositions wherein the boron hydrocarbyl compound is a Lewis acid of the formula BXYZ where at least one of X, Y and Z is a monovalent hydrocarbyl group. A preferred catalyst composition comprises a palladium complex and B(C.sub.6 F.sub.5).sub.3.Type: GrantFiled: November 4, 1996Date of Patent: June 9, 1998Assignee: BP Chemical LimitedInventors: Neil Andrew Cooley, Adrian Peter Kirk
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Patent number: 5741939Abstract: A process for the copolymerization of carbon monoxide with an olefinically unsaturated compound comprising contacting the monomers in the presence of a liquid diluent with a catalyst composition which is based on(a) a source of a Group VIII metal,(b) a bidentate ligand of the general formulaR.sup.1 R.sup.2 M.sup.1 --R--M.sup.2 R.sup.3 R.sup.4 wherein M.sup.1 and M.sup.2 independently represent a phosphorus, arsenic or antimony atom, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent unsubstituted or substituted hydrocarbyl groups on the understanding that at least one of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represents a polar substituted aryl group and R represents a bivalent bridging group containing at least two carbon atoms in the bridge, and(c) a boron hydrocarbyl compound,with application of a stirring power transmitted to the polymerization mixture of at least 0.25 kW/m.sup.3.Type: GrantFiled: March 21, 1996Date of Patent: April 21, 1998Assignee: Shell Oil CompanyInventors: Frank Baardman, Arleen Marie Bradford, Jayne Jubb, Pieter Scheerman, Rudolf Jacobus Wijngaarden
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Patent number: 5654487Abstract: Catalyst compositions for preparing polyketones comprising (a) a Group VIII metal compound, containing at least one ligand capable of coordinating to the Group VIII metal, and (b) a boron hydrocarbyl compound are disclosed, in particular catalyst compositions wherein the boron hydrocarbyl compound is a Lewis acid of the formula BXYZ where at least one of X, Y and Z is a monovalent hydrocarbyl group. A preferred catalyst composition comprises a palladium complex and B(C.sub.6 F.sub.5).sub.3.Type: GrantFiled: June 6, 1995Date of Patent: August 5, 1997Assignee: BP Chemicals LimitedInventors: Neil Andrew Cooley, Adrian Peter Kirk
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Patent number: 5599913Abstract: New chromoionophores of the formula IV ##STR1## wherein a=0-3, b=0 or 1, c =0 or 1, x=0 or 1, y=0 or 1, z=0 or 1,R', which may be the same or different in each aryl group, is H, halogen, hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;R, which may be the same or different, is hydrocarbyl, aryl, hydrocarbylaryl, or a substituted derivative thereofare useful in optical sensors or colourmetric reagents for clinical use particularly for lithium, When complexed with lithium, the chromoionophores of the invention and other calixarene derivatives can be used for detecting amines, particularly trimethylamine, as an indicator of fish spoilage.Type: GrantFiled: March 28, 1995Date of Patent: February 4, 1997Inventors: Stephen J. Harris, Dermot Diamond, Michael A. McKervey
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Patent number: 5346873Abstract: A catalyst active in the preparation of alternating olefin/carbon monoxide (CO) copolymers is constituted by:(a) at least one salt of a metal of Group IB of the Periodic System,(b) a mono or bidentate ligand base containing one or two nitrogen or phosphorus atoms capable of linking to the metal atom by means of dative bonds,(c) a mineral or organic oxidizer agent.Also disclosed are the preparation of the catalyst and the use of said catalyst in alternated copolymerization of ethylene (C2) and/or other olefins with carbon monoxide (CO).Type: GrantFiled: March 11, 1993Date of Patent: September 13, 1994Assignee: Enichem S.p.A.Inventors: Anna Sommazzi, Gabriele Lugli, Fabio Garbassi, Fausto Calderazzo
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Patent number: 5244545Abstract: Disclosed is an improved process for the removal of acetone from a production system wherein acetic anhydride is produced by contacting a mixture comprising methyl iodide and methyl acetate and/or dimethyl ether with carbon monoxide in the presence of a carbonylation catalyst or catalyst system. The process comprises two distillation steps wherein acetone is separated from a mixture of methyl acetate, methyl iodide and acetone.Type: GrantFiled: October 9, 1991Date of Patent: September 14, 1993Assignee: Eastman Kodak CompanyInventors: Steven L. Cook, Robert M. Schisla, Jr., Charles E. Outlaw, Joseph R. Zoeller
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Patent number: 5225523Abstract: A process for the preparation of low molecular weight polyketone polymers, wherein polymers of carbon monoxide with ethene and/or propene and optionally in addition with one or more other .alpha.-olefins are prepared by contacting the monomers in the presence of hydrogen with a catalyst containing a Group VIII metal and a tetraalkylbisphosphine ligand. The process may also be conducted in the presence of a liquid .alpha.-olefin diluent.Type: GrantFiled: June 19, 1992Date of Patent: July 6, 1993Assignee: Shell Oil CompanyInventors: Eit Drent, Johannes J. Keijsper
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Patent number: 5099047Abstract: A method for recovering a Group VIII metal solid complex from an organic compound-containing solution containing a Group VIII metal complex, wherein the Group VIII metal complex is precipitated in the presence of a trialkyl phosphine of the following formula (I): ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3 is an alkyl group and they may be the same or different from one another, and the sum of the carbon numbers of R.sub.1, R.sub.2 and R.sub.3 is at least 42.Type: GrantFiled: November 13, 1990Date of Patent: March 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Yuji Kawaragi
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Patent number: 4945185Abstract: A hydrocarbonylation process for producing an aldehyde or a mixture of a ketone and an aldehyde which comprises:(I) forming a reaction mixture comprising:(a) a catalytic amount of a complex catalyst consisting essentially of rhodium in complex combination with:(i) a triorganophosphine, and(ii) a carboxylic acid having a phenyl group substituted at the para position with a non-reactive electron-withdrawing group, said phenyl group being free of further substitution and said electron withdrawing group being substantially non-reactive in said process;(b) an alpha-olefin having 2 to 5 carbon atoms,(c) carbon monixide, and(d) hydrogenwith the proviso that the reaction mixture has mole ratio of said carbxoylic acid to rhodium of at least about 2; and(II) maintaining the reaction mixture at a temperature and pressure at which said (b), (c) and (d) react to form an aldehyde or a mixture of an aldehyde and a ketone.Type: GrantFiled: December 5, 1989Date of Patent: July 31, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Anthony J. Papa, David R. Bryant
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Patent number: 4879417Abstract: A process for the preparation of ketones by carbonylation of alkenes with carbon monoxide, using a catalyst system comprising: component (a) a ruthenium compound, and component (b) at least one acid selected from hydrohalogenic acids and carboxylic acids having a pK.sub.a value.gtoreq.3 (measured at 25.degree. C. in aqueous solution), with said process being carried out in a water miscible solvent, at a operational pressure in the range of from about 20 bar to about 100 bar and at a temperature in the range of about 70.degree. C. to about 200.degree. C.Type: GrantFiled: July 25, 1988Date of Patent: November 7, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4851582Abstract: Carbon monoxide and at least one olefinically unsaturated organic compound may be polymerized by contacting the monomers in the presence of a catalyst which comprises a Group VIII metal compound of palladium, cobalt or nickel, a halide of tin or germanium, a nitrogen bidentate ligand and an organic oxidant. The polymers prepared are linear alternating polymers which consist of units with the formula ##STR1## where A is the residue of an alkenically unsaturated organic compound monomer.Type: GrantFiled: May 13, 1987Date of Patent: July 25, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4788325Abstract: A process for making a carbonyl-containing compound is disclosed. In this process an allylic ether is contacted with water in the presence of a cobalt-containing material under an atmosphere of carbon monoxide gas.Type: GrantFiled: May 29, 1987Date of Patent: November 29, 1988Assignee: National Distillers and Chemical CorporationInventor: Biau-Hung Chang
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Patent number: 4788338Abstract: A process for preparing ketones comprises reacting an alkene with carbon monoxide and a secondary alcohol at elevated temperature in the presence of a rhodium catalyst and an aminoalcohol or aminoether promoter. A preferred catalyst is Rh.sub.6 (CO).sub.16 and a preferred promoter is N(CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3).sub.3.Type: GrantFiled: June 12, 1987Date of Patent: November 29, 1988Assignee: The British Petroleum Company p.l.c.Inventor: Robert G. Beevor
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Patent number: 4769496Abstract: A process for producing higher ketones comprises the step of contacting under suitable conditions a feed comprising at least one C.sub.2 -C.sub.6 aliphatic aldehyde, and preferably also carbon monoxide, with a catalyst composition comprising (i) copper and/or an oxide thereof and (ii) zinc oxide. Preferably, the feed aldehyde is propanal, and the product comprises at least one C.sub.5 ketone. Ketones are substantially absent from the aldehyde feed.Type: GrantFiled: June 12, 1987Date of Patent: September 6, 1988Assignee: Phillips Petroleum CompanyInventors: David J. Elliott, Filippo Pennella
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Patent number: 4740625Abstract: Carbon monoixide, ethylene and optionally at least one olefinically unsaturated organic compound may be polymerized by contacting the monomers in the presence of a catalyst which comprises a Group VIII metal compound of palladium, cobalt or nickel, a bidentate phosphorus, arsenic or antimony ligand and a halide of tin or germanium. The tin or germanium halide is not required when a palladium halide is used as the Group VIII metal compound. The polymers prepared are linear alternating polymers which consist of units with the formula ##STR1## and units having the formula ##STR2## where A is the residue of an alkenically unsaturated organic compound monomer.Type: GrantFiled: May 13, 1987Date of Patent: April 26, 1988Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4727195Abstract: A process for preparing compounds of the general formula:R--C.tbd.C--C(O)--C(R).dbd.CH.sub.2 (I)R represents an H atom or an optionally substituted hydrocarbyl group, by reacting a compound R--C.tbd.CH with CO in the presence of a Pd(II) compound, an organic phosphine and a protonic acid having a pK.sub.a below 3.0.Compounds of formula I in which R represents an optionally substituted hydrocarbyl group are novel.Type: GrantFiled: August 22, 1986Date of Patent: February 23, 1988Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4694108Abstract: A process of producing higher ketones comprises the step of contacting under suitable conditions a feed comprising (a) at least one C.sub.3 -C.sub.6 aliphatic ketone, (b) at least one C.sub.2 -C.sub.6 aliphatic aldehyde and, preferably, also (c) carbon monoxide with a catalyst composition comprising (i) copper or an oxide thereof and (ii) zinc oxide. Preferably, the feed ketone is methyl ethyl ketone, the feed aldehyde is propanal, and the product comprises at least one C.sub.7 ketone.Type: GrantFiled: August 1, 1986Date of Patent: September 15, 1987Assignee: Phillips Petroleum CompanyInventor: David J. Elliott
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Patent number: 4605775Abstract: Higher ketones prepared by contacting under suitable reaction conditions a feed stream comprising (a) a lower ketone having 3-5 carbon atoms per molecule and (b) carbon monoxide with a catalyst composition comprising copper oxide, zinc oxide and, optionally, alumina. The formed higher ketones contain at least one carbon atom per molecule more than the lower feed ketone, preferably methyl ethyl ketone.Type: GrantFiled: April 22, 1985Date of Patent: August 12, 1986Assignee: Phillips Petroleum CompanyInventor: David J. Elliott
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Patent number: 4602116Abstract: The present invention provides a process for the selective production of ketones under hydroformylation conditions. In particular, the process comprises the hydroformylation of at least one olefin in the presence of hydrogen, carbon monoxide, and a catalyst which consists essentially of triruthenium dodecacarbonyl. The olefin preferably comprises propylene. The reaction is conducted under conditions such that the ratio of olefin:ruthenium is about 200:1 to 3000:1, the ratio of carbon monoxide:hydrogen:olefin to about 1:1.4:4 to 1:6:100, the total pressure is about 500 to 10,000 psig, the carbon monoxide partial pressure is about 50 to 500 psig, and the reaction temperature is about 60.degree. to 250.degree. C.Type: GrantFiled: April 9, 1985Date of Patent: July 22, 1986Assignee: Eastman Kodak CompanyInventor: James L. Cooper
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Patent number: 4599454Abstract: Higher ketones are prepared by contacting, under suitable reaction conditions, a feed stream comprising (a) a primary alcohol of 2-6 carbon atoms per molecule (preferably ethanol, 1-propanol or 1-butanol) and (b) carbon monoxide with a catalyst composition containing copper oxide, zinc oxide and, optionally, alumina.Type: GrantFiled: April 22, 1985Date of Patent: July 8, 1986Assignee: Phillips Petroleum CompanyInventors: David J. Elliott, Filippo Pennella
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Patent number: 4599453Abstract: A process for the single-stage production in the liquid or gaseous phase, of higher aliphatic ketones starting from ketones of lower molecular weight, characterized in that the starting ketones are reacted with carbon monoxide in the presence of a catalyst in the form of cooper supported on a metal oxide.The catalyst is prepared by depositing on the metal oxide the product obtained from hydrolyzing a cuprammonium solution, then calcining the solid system obtained in air and reducing the calcined product by means of hydrogen.Type: GrantFiled: February 25, 1985Date of Patent: July 8, 1986Assignee: Consiglio Nazionale Delle RicercheInventors: Carlo Fragale, Michele Gargano, Michele Rossi
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Patent number: 4595784Abstract: A compound having the general formula R.sub.x COH[COR].sub.y, wherein R is a lower alkyl hydrocarbon radical, y is 0 or 1, and x is 2 when y is 1 and 3 when y is 0, is prepared by admixing carbon monoxide, a transition metal halide, and an organomonolithium compound or an anionic equivalent thereof.Type: GrantFiled: November 7, 1984Date of Patent: June 17, 1986Assignee: Board of Control of Michigan Technological UniversityInventors: G. David Mendenhall, Hsiang T. Chen
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Patent number: 4590298Abstract: This invention provides a process for the production of C.sub.4 -C.sub.5 hydroxyketones by reaction of formaldehyde and synthesis gas in a basic organic solvent in the presence of a tungsten and Group VIII metal-containing catalyst composition.Type: GrantFiled: March 5, 1985Date of Patent: May 20, 1986Assignee: Celanese CorporationInventor: Tessie M. Che
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Patent number: 4585897Abstract: A process for hydration and condensation of acetylene in a crude acetylene stream containing water in the presence of a zirconia-alumina catalyst containing water to prepare aliphatic, aromatic and oxygenated compounds suitable for use as high octane liquid water fuels and as octane improvers for motor fuels is disclosed.Type: GrantFiled: August 24, 1984Date of Patent: April 29, 1986Assignee: Standard Oil Company (Indiana)Inventors: Ellis K. Fields, Mark L. Winzenburg, David A. De Marco
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Patent number: 4536597Abstract: A process for the selective hydrocarboxylation of propylene to produce predominantly isobutyric acid in the liquid phase is provided. The reaction of propylene, carbon monoxide and water wherein a water to propylene ratio is maintained of from about 0.01 to a value less than 1.0 is effected at a temperature of about 75.degree. C. to about 150.degree. C. and at a pressure of about 250 psi to about 5000 psi in the presence of a carboxylic acid solvent and a catalyst comprising a coordinating palladium compound, an organo-arsine and a hydrogen halide.Type: GrantFiled: December 31, 1979Date of Patent: August 20, 1985Assignee: The Standard Oil Company (Ohio)Inventors: Frederick A. Pesa, Thomas A. Haase
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Patent number: 4510320Abstract: A process is provided for the production of aliphatic acetate esters and gaseous alkanes comprising contacting acetic acid and synthesis gas in the vapor phase at elevated temperature and pressure in the presence of a catalyst containing the mixed oxides of ruthenium and nickel, and optionally an alkali metal oxide and the oxides of cobalt, cadmium, zinc or mixtures thereof. Other carboxylic acids may be substituted for acetic acid as desired.Type: GrantFiled: December 24, 1981Date of Patent: April 9, 1985Assignee: The Standard Oil Co. (Ohio)Inventors: Frederick A. Pesa, Anne M. Graham
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Patent number: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4444624Abstract: The disclosure relates to a process for separating acetone from reaction mixtures originating from the reaction of methyl acetate and/or dimethylether with carbon monoxide and optionally hydrogen in the presence of a catalyst system consisting of carbonyl complexes of noble metals of group VIII of the Periodic System of the elements, acetic acid, an organophosphorus or organonitrogen compound, methyl iodide and optionally carbonyl-yielding compounds of common metals.Type: GrantFiled: August 27, 1982Date of Patent: April 24, 1984Assignee: Hoechst AktiengesellschaftInventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
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Patent number: 4390734Abstract: Propylene glycol monoalkyl ethers are prepared in good yield by reacting acetaldehyde and an alkanol (or by reacting an acetal) with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt-containing compound and a cocatalyst comprising a member of the group consisting of rhodium-containing compounds, ruthenium-containing compounds and nickel-containing compounds, and heating the resulting mixture at moderate temperatures and pressures for sufficient time to produce the desired glycol monoalkyl ether, and then recovering the same from the reaction mixture.Type: GrantFiled: January 13, 1982Date of Patent: June 28, 1983Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4356327Abstract: Propylene glycol monoalkyl ethers and alkoxyacetones are formed by contacting a mixture of carbon monoxide and hydrogen and (a) acetaldehyde or (b) an acetal and an alcohol, with a catalyst comprising a cobalt-containing compound and at least one tin- or germanium-containing promoter.Type: GrantFiled: October 29, 1981Date of Patent: October 26, 1982Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4289911Abstract: Methylisobutylketone is produced from acetone in a high yield with a good selectivity through one-step reaction by contacting acetone together with at least one of water and hydrogen with an element of Group VIII of the periodic table, a halogen and a phosphorus compound as a catalyst under a super atmospheric pressure in a carbon monoxide atmosphere.Type: GrantFiled: June 9, 1980Date of Patent: September 15, 1981Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuo Isogai, Takashi Okawa, Natsuko Wakui