Preparing From Carbonyl Containing Compound Patents (Class 568/876)
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Patent number: 7169959Abstract: Unsaturated palm oil fatty alcohols with an iodine number in the range from 65 to 85, which contain substantially unsaturated fatty alcohols and mixtures of saturated fatty alcohols of the formula (I): R1OH ??(I) in which R1 is a saturated or unsaturated, linear or branched alkyl radical having 14 to 20 carbon atoms, are obtained by (a) fractionating palm oil fatty acid methyl esters into a mainly saturated C16-distillate and a mainly unsaturated C16/18-bottom product; and (b) hydrogenating the bottom product with retention of the double bonds to give the corresponding alcohols.Type: GrantFiled: June 12, 2001Date of Patent: January 30, 2007Assignee: Cognis Deutschland GmbH & Co. KGInventors: Stephan Heck, Norbert Klein, Horst-Dieter Komp, Christiane Boehr, Norbert Huebner, Alfred Westfechtel
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Patent number: 7164049Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.Type: GrantFiled: March 27, 2003Date of Patent: January 16, 2007Assignee: The Nutrasweet CompanyInventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark Paster, Indra Prakash
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Patent number: 7161048Abstract: Methanol is produced from bacterially oxidized waste methane by reaction with Pd+2, Cu+2, air, and molten phthalic anhydride in an entrained oxidizer generating half ester of methyl phthalate which is reaction distilled to produce methanol and recycle phthalic anhydride containing the Pd+2, Cu+2 phthalate catalyst.Type: GrantFiled: May 11, 2006Date of Patent: January 9, 2007Assignee: Rinnovi, L.L.C.Inventors: Carol Knox, legal representative, Walter R. Knox, deceased
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Patent number: 7138552Abstract: The present invention relates to a process for preparing a C13-alcohol mixture which is suitable, in particular, as precursor for the preparation of compounds having surfactant properties and of plasticizers.Type: GrantFiled: March 25, 2003Date of Patent: November 21, 2006Assignee: OXENO Olefinchemie GmbHInventors: Alfred Kaizik, Walter Tötsch, Wilhelm Droste, Wilfried Büschken, Dirk Röttger, Klaus-Diether Wiese
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Patent number: 7098369Abstract: A process for producing primary alcohols from secondary alcohols and/or tertiary alcohols and/or ketones, wherein the process comprises reacting a compound selected from a secondary alcohol, a tertiary alcohol, a ketone, or mixtures thereof, with carbon monoxide and hydrogen in the presence of a catalyst based on: (i) a source of Group VIII metal, (ii) a bidentate ligand having the general formula (I): R1R2M1-R-M2R3R4??(I) wherein M1 and M2 are independently P, As or Sb; R1 and R2 together represent a bivalent substituted or unsubstituted cyclic aliphatic group whereby the two free valencies are linked to M1; R3 and R4 independently represent a substituted or unsubstituted hydrocarbyl group, or together represent a bivalent or non-substituted cyclic group whereby the two free valencies are linked to M2; and R represents a bivalent aliphatic bridging group; and (iii) an acid having a pKa of 3 or less which is in excess over the Group VIII metal.Type: GrantFiled: September 24, 2003Date of Patent: August 29, 2006Assignee: Shell Oil CompanyInventors: Eit Drent, Renata Helena Van Der Made
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Patent number: 7084312Abstract: A process for the hydrogenation of an organic compound containing at least one carbonyl group comprises bringing the organic compound in the presence of hydrogen into contact with a shaped body which can be produced by a process in which (i) an oxidic material comprising copper oxide, zinc oxide and aluminum oxide is made available, (ii) pulverulent metallic copper or pulverulent cement or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to form a shaped body.Type: GrantFiled: August 22, 2000Date of Patent: August 1, 2006Assignee: BASF AktiengesellschaftInventors: Sylvia Huber, Michael Jolyon Sprague, Boris Breitscheidel, Joachim Wulff-Döring, Michael Hesse, Rolf Pinkos, Shelue Liang, Otto Kumberger, Marc Walter
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Patent number: 7041857Abstract: This invention relates to an improvement in a liquid phase process for producing isopropanol by the hydrogenation of acetone in the presence of a hydrogenation catalyst; the improvement comprising; contacting acetone with hydrogen under continuous liquid phase conditions; and, employing a sponge metal catalyst promoted with an effective amount of chromium.Type: GrantFiled: September 7, 2005Date of Patent: May 9, 2006Assignee: Air Products and Chemicals, Inc.Inventors: Kathryn Sue Hayes, John William Mitchell, Anita Niak, Michael Gerard Turcotte
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Patent number: 6919488Abstract: A process for producing saleable liquids from organic material comprising the following steps. Providing organic material and separating it into solids, liquids and vapor. Reacting the liquids, combining it with water vapor and producing a volatized gas stream. Removing nitrogen dioxide from the gas stream to produce a scrubbed volatized gas stream. Reacting the scrubbed volatized gas stream with water vapor to produce a combined volatized gas stream. Removing carbon dioxide from the combined volatized gas stream to produce a subtracted volatized gas stream. Reacting the subtracted volatized gas stream with methanol to produce an enhanced volatized gas stream. Distilling the enhanced volatized gas stream to produce ethanol.Type: GrantFiled: May 20, 2003Date of Patent: July 19, 2005Assignee: Woodland Chemical Systems, Inc.Inventors: Larry Jack Melnichuk, Karen Venita (Sue) Kelly
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Patent number: 6916964Abstract: The present invention relates to a continuous process for the selective hydrogenation of olefinically unsaturated carbonyl compounds to give unsaturated alcohols in particular of citral to give a mixture of geraniol and nerol, in a reactor containing a liquid phase, in which at least one catalyst is suspended, and which can additionally contain a gas phase, wherein the liquid phase and, if present, the gas phase are passed through a device in the reactor having openings or channels.Type: GrantFiled: December 4, 2002Date of Patent: July 12, 2005Assignee: BASF AGInventors: Hans-Georg Göbbel, Till Gerlach, Frank Funke, Klaus Ebel, Signe Unverricht, Gerd Kaibel
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Patent number: 6911567Abstract: Guerbet alcohols of the formula (I) CH3(CH2)nCHR1CH2OH??(I) wherein R1 is a linear alkyl radical having n-1 carbon atoms and n is a number of from 5 to 11 are produced by a process which comprises contacting a fatty alcohol of the formula (II) R2OH??(II) wherein R2 is a linear alkyl radical having from 6 to 12 carbon atoms with a carbonyl compound and an alkall metal hydroxide. The use of heavy metal catalysts usually associated with the production of Guerbet alcohols is avoided thereby reducing the potential for heavy metal pollution of the environment.Type: GrantFiled: September 11, 2001Date of Patent: June 28, 2005Assignee: Cognis Deutschland and GmbH & Co. KGInventors: Sabine Both, Georg Fieg, Erich Reuter, Frank Bartschick, Bernhard Gutsche
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Patent number: 6906228Abstract: In a process for preparing alcohols by catalytic hydrogenation of carbonyl compounds over a catalyst comprising rhenium on activated carbon, the catalyst used comprises rhenium (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5, platinum (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5 and, if appropriate, at least one further metal selected from among Zn, Cu, Ag, Au, Ni, Fe, Ru, Mn, Cr, Mo, W and V in a weight ratio to the activated carbon of from 0 to 0.25, and the activated carbon has been nonoxidatively pretreated It is also possible to prepare ethers and lactones if the hydrogen pressure is not more than 25 bar. In this case, the activated carbon in the catalyst may also have been nonoxidatively pretreated.Type: GrantFiled: March 1, 2001Date of Patent: June 14, 2005Assignee: BASF AGInventors: Rolf Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Döring, Frank Stein, Thomas Nöbel, Sylvia Huber
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Patent number: 6867323Abstract: Improved methods for generating a —C—C— bond by cross-coupling of a transferable group with an acceptor group. The transferable group is a substituent of an organosilicon nucleophile and the acceptor group is provided as an organic electrophile. The reaction is catalyzed by a Group 10 transition metal complex (e.g., Ni, Pt or Pd), particularly by a palladium complex. Certain methods of this invention use improved organosilicon nucleophiles which are readily prepared, can give high product yields and exhibit high stereoselectivity. Methods of this invention employ activating ions such as halides, hydroxide, hydride and silyloxides. In specific embodiments, organosilicon nucleophilic reagents of this invention include siloxanes, particularly cyclic siloxanes. The combination of the cross-coupling reactions of this invention with ring-closing metathesis, hydrosilylation and intramolecular hydrosilylation reactions provide useful synthetic strategies that have wide application.Type: GrantFiled: June 6, 2001Date of Patent: March 15, 2005Assignee: The Board of Trustees of the University of IllinoisInventors: Scott E. Denmark, Jun Young Choi, Daniel Wehrli, Zhicai Wu, Luc Neuville, Weitao Pan, Ramzi F. Sweis, Zhigang Wang, Shyh-Ming Yang
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Patent number: 6855851Abstract: The present invention relates to a process for producing aliphatic C3-C10-alcohols, in particular 2-ethylhexanol, from high boilers by thermal treatment in the presence of an alkali metal compound and subsequent hydrogenation of the volatile products.Type: GrantFiled: October 30, 2003Date of Patent: February 15, 2005Assignee: Celanese Chemicals Europe GmbHInventors: Wolfgang Zgorzelski, Wilhelm Glick
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Publication number: 20040225157Abstract: The present invention relates to a process for the reduction of aliphatic, aromatic or heterocyclic organic compounds by means of hydrides and/or derivatives thereof.Type: ApplicationFiled: January 8, 2003Publication date: November 11, 2004Inventors: Hanns Wurziger, Guido Pieper
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Patent number: 6790999Abstract: Disclosed is a process for the continuous, semi-continuous or batch production of 3-buten-1-ol from 3,4-epoxy-1-butene wherein 3,4-epoxy-1-butene and formic acid are fed to a reaction zone having a catalyst solution comprising a palladium(0) compound, a tertiary phosphine, a trialkylamine and an organic solvent. Preferably in the operation of this invention, 3-buten-1-ol product and reaction side products serve as the organic solvent for the process. The preferred mode of operation is continuous addition of reactants to the reaction mixture with simultaneous, continuous distillation of a reaction product comprising 3-buten-1-ol.Type: GrantFiled: February 28, 2003Date of Patent: September 14, 2004Assignee: Eastman Chemical CompanyInventor: Stephen Neal Falling
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Patent number: 6765119Abstract: The invention relates to a process for the preparation of saturated C3-C20-alcohols in which a liquid hydrogenation feed comprising at least one C3-C20-aldehyde is passed over a bed of a hydrogenation catalyst in the presence of a hydrogen-containing gas, which comprises adding to the hydrogenation feed an amount, homogeneously soluble therein, of a salt-like base. The addition of base suppresses side reactions, such as acetalization, aldolization, Tischtschenko reaction or ether formation.Type: GrantFiled: November 14, 2002Date of Patent: July 20, 2004Assignee: BASF AktiengesellschaftInventors: Herwig Hoffmann, Michael Röper, Heinrich-Josef Blankertz, Max Strohmeyer, Helmut Walz, Helmut Zinke-Allmang
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Patent number: 6759561Abstract: The present invention relates to a process for the preparation of tetrahydrogeraniol, wherein the product mixtures and distillation residues from linalool, citronellal, citronellol or geraniol/nerol synthesis are fed directly to catalytic hydrogenation.Type: GrantFiled: December 4, 2002Date of Patent: July 6, 2004Assignee: BASF AktiengesellschaftInventors: Frank Funke, Till Gerlach, Klaus Ebel, Signe Unverricht, Frank Haese, Kirsten Burkart, Hans-Georg Göbbel
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Patent number: 6723886Abstract: An apparatus and method is disclosed for producing alcohols, particularly methanol, according to an alcohol synthesis process. The apparatus comprises a catalytic distillation reactor where reactants are fed into the catalytic distillation reactor to undergo catalytic reaction to form methanol. Methanol production beyond the thermodynamic limit is achieved in the apparatus through use of multiple distillation stages, preferably at least three.Type: GrantFiled: May 16, 2002Date of Patent: April 20, 2004Assignee: ConocoPhillips CompanyInventors: Joe D. Allison, Harold A. Wright, Todd H. Harkins, Doug S. Jack
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Publication number: 20040030200Abstract: The present invention relates to an alcohol mixture which substantively comprises alcohols having 13 or 15 carbon atoms, to a process for its preparation, to a process for functionalizing these alcohol mixtures, and to the resultant functionalized alcohol mixtures and their use.Type: ApplicationFiled: December 18, 2002Publication date: February 12, 2004Inventors: Edgar Zeller, Jurgen Tropsch
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Publication number: 20040015017Abstract: A process for the hydrogenation, using molecular hydrogen (H2), of a catalytic system, wherein the catalytic system comprises a base and a complex of formula; (II) wherein Y represents simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and N2P2 is a tetradentate diimine-diphosphino ligand.Type: ApplicationFiled: April 25, 2003Publication date: January 22, 2004Inventors: Valentin Rautenstrauch, Raphael Churlaud, Robert Harold Morris, Kamaluddin Abdur-Rashid
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Patent number: 6617470Abstract: In a process for esterifying (meth)acrylic acid with an alkanol in the presence of an esterification catalyst, in which unconverted starting compounds and (meth)acrylic ester to be formed are separated off by distillation and an oxyester-containing bottom product is formed, the bottom product is first separated off and then the oxyesters contained in it are cleaved in the presence of a relatively long-chain alkylbenzenesulfonic acid at elevated temperatures.Type: GrantFiled: May 11, 2001Date of Patent: September 9, 2003Assignee: BASF AktiengesellschaftInventors: Heinrich Aichinger, Holger Herbst, Gerhard Nestler, Jürgen Schröder, Stefan Beckmann
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Patent number: 6610888Abstract: A method of reacting a solution comprising a mixture of chemical compounds which are in chemical equilibrium with one another with at least one further chemical compound (9) is provided. The method comprises the following steps: fractionation of the solution by means of a separation method to give at least two fractions (5, 6) which are enriched in different chemical compounds of the mixture; and reaction of a fraction (5) with the further chemical compound or compounds (9). The fractionation is advantageously carried out using a film evaporator (1). Unreacted fractions (6) can be recirculated via a residence time vessel (3) back to the fractionation step. The method is particularly suitable for reactions of an aqueous formaldehyde solution in which various components of the solution (formaldehyde, methylene glycol, polyoxymethylene glycols) react in different ways.Type: GrantFiled: May 31, 2000Date of Patent: August 26, 2003Assignee: BASF AktiengesellschaftInventors: Eckhard Ströfer, Stephan Scholl, Hans Hasse
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Publication number: 20030069455Abstract: Disclosed is a method for preparing a substantially pure mixture of cyclododecanediol isomers. The isomers include 1,4-cyclododecanediol, 1,5-cyclododecanediol, and 1,6-cyclododecanediol. Also disclosed is a method for using a substantially pure mixture of cyclododecanediol isomers, which include the preparation of diamines; esters; diesters, such as diacetates and diacrylates; bis-phenol cyclododecane; and cyclododecanediol-based polyester polymers and polyester polyols.Type: ApplicationFiled: September 16, 2002Publication date: April 10, 2003Inventors: Samuel Livingston Lane, Edward Francis Moran, John Joseph Ostermaier
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Publication number: 20020177737Abstract: A composition and a process for using the composition in hydroformylation of unsaturated organic compounds are disclosed. The composition comprises a Group VIII metal and a phosphite-containing polymer having repeat units derived from (1) a carbonyl compound, a monomer, and phosphochloridite; (2) phosphorus trichloride, a polyhydric alcohol, and an aromatic diol; or (3) combinations of (1) and (2). The process comprises contacting an unsaturated compound, in the presence of the composition disclosed herein, with a fluid comprising hydrogen.Type: ApplicationFiled: May 17, 2002Publication date: November 28, 2002Inventors: Wilson Tam, Kathryn Eileen Schwiebert, Joe Douglas Druliner
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Publication number: 20020111520Abstract: A process for the production of 1,4-butanediol is described. The process comprises hydroformylating allyl alcohol in the presence of a solvent and a catalyst system comprising a rhodium complex, a ruthenium complex and a diphosphine ligand and hydrogenating the resulting 4-hydroxybutyraldehyde using the same catalyst system. The process gives high yield of 1,4-butanediol compared to 2-methyl-1,3-propanediol.Type: ApplicationFiled: December 13, 2000Publication date: August 15, 2002Inventor: Wilfred P. Shum
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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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Publication number: 20020019574Abstract: A process for producing alcohols, to obtain a straight-chain alcohol having a carbon number of n (where n=3 to 6), a branched chain alcohol having a carbon number of n (where n=3 to 6) and a branched chain alcohol having a carbon number of 2n (where n=3 to 6) from a mixed aldehyde comprising a straight-chain aldehyde having a carbon number of n (where n=3 to 6) and a branched chain aldehyde having a carbon number of n (where n=3 to 6) in an optional proportion, which comprises supplying the mixed aldehyde to a distillation column, withdrawing from the bottom of the column an aldehyde rich in the straight-chain aldehyde, dimerizing the straight-chain aldehyde, followed by hydrogenation to obtain the branched chain alcohol having a carbon number of 2n, while obtaining, as a fraction from the top of the column, an aldehyde rich in the branched chain aldehyde and having a straight-chain aldehyde concentration in the fraction of at least 30 wt %, subjecting the fraction to hydrogType: ApplicationFiled: May 20, 1999Publication date: February 14, 2002Inventors: AKIO UEDA, ATSUHIRO ADACHI
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Patent number: 6333441Abstract: A cis-olefin of the formula: R1—CH═CH—R2 is prepared by reducing an alkyne of the formula: R1—C≡C—R2 with formic acid in the presence of a palladium catalyst. R1 and R2 are independently selected from the group consisting of a hydrogen atom, ester group, substituted silyl group, carboxyl group, cyano group, aliphatic C1-C20 hydrocarbon group, and phenyl group. The cis-olefin which is a useful intermediate for the synthesis of fine chemicals is selectively produced in high yields.Type: GrantFiled: March 4, 1993Date of Patent: December 25, 2001Assignees: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Katsuaki Miyaji, Takehiro Amano
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Patent number: 6316680Abstract: In a process for isolating &agr;-ethynyl carbinols from the liquid reaction mixture from the addition of acetylene onto &agr;,&bgr;-unsaturated carbonyl compounds by distillation, the distillation is carried out continuously, the feed stream is introduced into the middle section of a distillation column (K), the major part of the water is distilled off azeotropically together with the solvent at the top of the column, and the &agr;-ethynyl carbinol target product is taken off below the feed point to the column.Type: GrantFiled: December 6, 1999Date of Patent: November 13, 2001Assignee: BASF AktiengesellschaftInventors: Ralf-Thomas Rahn, Harald Rust, Thomas Rühl, Jochem Henkelmann, Susanne Stutz
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Publication number: 20010034464Abstract: A reductive system including a silane, preferably PMHS, and an active zinc compound, which is monomeric and not a hydride, wherein a reduction of a carbonyl substrate to a corresponding alcohol is achievable.Type: ApplicationFiled: April 6, 2001Publication date: October 25, 2001Applicant: FIRMENICH SAInventor: Hubert Mimoun
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Publication number: 20010023553Abstract: A Fischer-Tropsch reaction is conducted using a synthesis gas (mixture of carbon monoxide and hydrogen) as a raw material to synthesize hydrocarbons containing a large amount of olefin. These hydrocarbons are separated into a light fraction and a heavy fraction by means of a heat exchanger and an oxo process is conducted with respect to the olefin contained in the light fraction with a cobalt catalyst. As a result, an oxygenated fuel containing alcohol, aldehyde, etc. is manufactured. The oxygenated fuel made by such a manufacturing method is excellent in lubricity and oxidation stability, has a high cetane number, and is also capable of suppressing generation of soot when the oxygenated fuel is combusted.Type: ApplicationFiled: March 12, 2001Publication date: September 27, 2001Inventors: Kaoru Fujimoto, Noritatsu Tsubaki
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Patent number: 6229056Abstract: The proposal is for unsaturated fatty substances with improved cold behavior obtained by (a) transesterifying a new low stearic (LS) sunflower oil with an oleic acid content of over 85 wt. % and a stearic acid content of under 3 wt. %, and (b) hydrogenating the resultant methyl esters in the prior art manner into the corresponding unsaturated fatty alcohols in the iodine number range from 90 to 100. The fatty substances are also distinguished by improved color and odor and are suitable for making fatty chemical products, e.g. alkoxylates, ether sulphates, sulphates and esters.Type: GrantFiled: May 8, 1997Date of Patent: May 8, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Achim Ansmann, Guenther Demmering, Georg Assmann, Fritz Schuster, Alfred Westfechtel, Michael Koehler
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Patent number: 6054628Abstract: In a process for carrying out an exothermal reaction, selected from the addition reaction of organomagnesium halide compounds to carbonyl compounds and the ensuing hydrolysis of the addition product, a considerable fraction of the heat liberated during the reaction is removed by evaporation of the solvent.Type: GrantFiled: October 21, 1997Date of Patent: April 25, 2000Assignee: BASF AktiengesellschaftInventors: Manfred Stroezel, Udo Rheude, Ralf-Thomas Rahn, Gerd Kaibel
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Patent number: 6022982Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids such as oleic acid is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.9 to .DELTA..sup.15 unsaturated fatty acids in the presence of an acid catalyst and at a temperature between about 20 to 70.degree. C. Moreover, yields of the .delta.-lactones may be increased even further by reaction in the presence of dipolar, non-participating, non-aqueous solvents. The unsaturated fatty acids may be free or esterified with glycerol or other aliphatic alcohols, and the .delta.-lactones may be produced by reacting mono-, di- or triglycerides of the unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the instant process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification or steam splitting.Type: GrantFiled: December 14, 1998Date of Patent: February 8, 2000Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Terry A. Isbell, Steven C. Cermak
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Patent number: 5962711Abstract: A typical traditional reactor for hydrogenation consists of a tank filled with a liquid and a gas and a small particle catalyst. The reaction is carried out at high pressures and high temperatures. Lack of gas on the catalyst surface limits the velocity of reaction. Much work has been done to increase the quantity of gas on the catalyst. It has not been possible to solve this problem effectively with the techniques of today. According to the invention an extra solvent is added to the reaction mixture. By bringing the whole mixture (solvent, substrate, hydrogen and reaction products) to super-critical or near-critical state, a substantially homogeneous mixture can be obtained. By this method it is possible to control the concentration of gas on the catalyst to the desired level. The velocity of reaction is thereby increased considerably. The hydrogenation reactions principally involved comprise hydrogenation of carbon-carbon double bonds (C.dbd.Type: GrantFiled: December 27, 1996Date of Patent: October 5, 1999Assignee: Poul Moller Ledelses- OG Ingeniorradgivning APSInventors: Magnus Harrod, Poul M.o slashed.ller
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Patent number: 5917097Abstract: A process for producing unsaturated fatty compounds having improved low-temperature properties bya) splitting lauric oils into fatty acids and glycerol,b) subjecting the fatty acids to fractional crystallization to obtain a fraction of unsaturated fatty acids, andc) hydrogenating the unsaturated fatty acids, optionally after converting the unsaturated fatty acids into their lower alkyl esters, to form unsaturated fatty alcohols having an iodine value of from about 85 to about 100.Type: GrantFiled: June 10, 1997Date of Patent: June 29, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Michael Koehler, Alfred Westfechtel, Guenter Demmering, Horst-Dieter Komp, Christiane Boehr, Achim Ansmann, Udo Steinberner
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Patent number: 5849935Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids which are free or esterified with glycerol is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids in the presence of an acid, clay or zeolite catalyst. Alternatively, the .delta.-lactones may be produced by reacting one or more triglycerides which are esters of glycerol with .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification. Optionally, the .delta.-lactones so formed may be further reacted with an alkali in an aqueous solution to produce 5-hydroxy fatty acids.Type: GrantFiled: September 27, 1995Date of Patent: December 15, 1998Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Terry A. Isbell, Beth A. Plattner, Robert Kleiman
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Patent number: 5847239Abstract: Dihydromyrcene is reacted with a carboxylic acid, eg acetic acid, to produce an ester which is then reacted with an alcohol in a transesterification reaction to produce (dihydro)myrcenol and another ester. The preferred alcohol is 4-tertiarybutylcyclohexanol. Myrcenol can be produced in a similar way.Type: GrantFiled: January 15, 1997Date of Patent: December 8, 1998Assignee: Quest International B.V.Inventors: Paul Nicolas Davey, Clive Derek Richardson, Christopher Paul Newman, Barrie R. Hart
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Patent number: 5696299Abstract: A process for producing an optically active alcohol comprising carrying out interesterification between a racemic alcohol and an ester selected from the group consisting of (a) a diester between a lower monohydric alcohol and a saturated dicarboxylic acid having 14 or more carbon atoms, (b) a triglyceride of a saturated fatty acid having 16 or more carbon atoms, and (c) a monoester between a lower monohydric alcohol and a saturated fatty acid having 18 or more carbon atoms in the presence of lipase, preferably heat-resistant lipase, and in the presence or absence of a solvent, preferably in the absence of a solvent, under a substantially water-free condition, separating an optically active alcohol rich in either one of R- and S-forms from the reaction mixture, and adding an optically inactive non-racemic alcohol to the residue of the previous step to carry out interesterification under the same conditions as in the previous reaction to separate the other enantiomer.Type: GrantFiled: September 15, 1995Date of Patent: December 9, 1997Assignee: The Nisshin Oil Mills, Ltd.Inventors: Satoshi Negishi, Seiichi Shirasawa, Junko Suzuki, Yukie Masuda
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Patent number: 5495055Abstract: A deactivated supported ruthenium catalyst which has been used to continuously hydrogenate an aqueous acetone stream is regenerated by contacting with steam at an elevated temperature. Periodic regeneration in this manner serves to maintain a high rate of reaction in a process which converts acetone to isopropanol.Type: GrantFiled: February 13, 1995Date of Patent: February 27, 1996Assignee: Arco Chemical Technology, L.P.Inventor: Michael A. Rueter
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Patent number: 5334779Abstract: Disclosed are catalyst compositions comprised of the oxides of copper, zinc, and a third element selected from the group consisting of aluminum, magnesium, zirconium, and mixtures thereof, and the use of such catalyst compositions in the hydrogenation of carbonyl compounds such as carboxylate esters to obtain the alcohol corresponding to the acid residue of the ester.Type: GrantFiled: June 1, 1993Date of Patent: August 2, 1994Assignee: Eastman Kodak CompanyInventor: Yeong-Jen Kuo
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Patent number: 5254758Abstract: In a hydrogenation process, an organic feedstock, such as an unsaturated organic compound containing at least one unsaturated linkage selected from >C.dbd.C<, >C.dbd.O, --C.tbd.C--, and --C.tbd.Type: GrantFiled: February 12, 1992Date of Patent: October 19, 1993Assignee: Davy McKee (London) LimitedInventors: Andrew G. Hiles, Michael W. M. Tuck
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Patent number: 5243095Abstract: In one embodiment, the invention relates to a catalyst in powdered form comprising the oxides of copper, iron, aluminum and manganese wherein the atomic ratio of copper to iron is at least 1:1. In another embodiment, the invention relates to a process for preparing such hydrogenation catalysts which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt, at least one water-soluble iron salt, and at least one water-soluble manganese salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions wherein an insoluble solid is formed;(D) recovering the soluble solid; and(E) calcining the recovered solid to form the desired catalyst.The invention also relates to a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters.Type: GrantFiled: April 24, 1992Date of Patent: September 7, 1993Assignee: Engelhard CorporationInventors: Brian D. Roberts, Deepak S. Thakur, Thomas J. Sullivan, Robert A. Plundo
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Patent number: 5214220Abstract: The invention relates to a process for the preparation of an alcohol by hydrogenation of an aldehyde at elevated temperature and superatmospheric pressure in the presence of a homogeneous catalytic system comprising a source of a Group VIII metal compound and a bidentate phosphine.Type: GrantFiled: August 10, 1992Date of Patent: May 25, 1993Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5198592Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.Type: GrantFiled: October 15, 1990Date of Patent: March 30, 1993Assignee: Engelhard De Meern B.V.Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
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Patent number: 5149889Abstract: A process is disclosed for the preparation of tertiary alcohols, alpha-alkyl substituted nitriles, alkyl-substituted imines or tertiary amines by alkylation of a starting material that is a carbonyl compound or a nitrile followed by hydrolysis wherein the alkylation is carried out with the aid of a reaction system formed by suspending a mixture of:substantially 15 to 25% by weight of methyllithium or ethyllithium;substantially 35 to 45% by weight of an inorganic compound selected from the group which consists of at least one metal oxide selected from the group which consists of SiO.sub.2, Al.sub.2 O.sub.3, and CaO, and synthetic anhydrous aluminum silicate; andsubstantially 35 to 45% by weight of a paraffin oil or wax; in an organic solvent selected from the group which consists of:C.sub.5 to C.sub.10 saturated aliphatic hydrocarbons, C.sub.5 to C.sub.Type: GrantFiled: October 30, 1990Date of Patent: September 22, 1992Assignee: Metallgesellschaft AktiengesellschaftInventors: Jurgen Deberitz, Wilfried Weiss
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Patent number: 5112984Abstract: A process for preparing cyclic nitrogen-containing compounds which comprises contacting an acyclic nitrogen-containing compound with a CO.sub.2 synthon at an elevated temperature for a period of time sufficient to produce the cyclic nitrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: May 12, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Forrest A. Richey, Jr., Arthur R. Doumaux, Jr.
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Patent number: 5004844Abstract: A process for the preparation of a primary or secondary alcohol, which comprises hydrogenating respectively an aldehyde or ketone in the presence of a catalyst system comprising a platinum compound, an acid having a pKa in the range from about 2 to about 10.5 and a phosphorus compound of the formula R.sup.1 R.sup.2 POH, wherein R.sup.1 and R.sup.2 each independently represents an alkyl group or a phenyl group, at a temperature in the range from about 20.degree. to about 150.degree. C. and at a pressure in the range from about 1 to about 100 bar.Type: GrantFiled: June 28, 1989Date of Patent: April 2, 1991Assignee: Shell Oil CompanyInventors: Petrus W. N. M. Van Leeuwen, Cornelis F. Roobeek
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Patent number: 4999177Abstract: A process is disclosed for the preparation of high purity carbon monoxide by heating methyl formate in the presence of a catalyst of a precious metal compound with or without a promoter of alkali or alkaline earth metal compound.Type: GrantFiled: April 10, 1989Date of Patent: March 12, 1991Assignee: Dairen Chemical CorporationInventors: Shien-Chang Chen, Wan-Jy Cheng, Fu-Shen Lin, Fu-Juh Huang
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Patent number: 4997978Abstract: Alkyl carboxylates of the formula:R--CO--O--CH.sub.2 R'are prepared by hydrocarbonylating a compound of the formula:R--CO--O--R'in the simultaneous presence, in the reaction medium, of cobalt, ruthenium, an alkyl iodide and an ionic iodide, the atomic ratio Co/Ru being less than or equal to 1, and the total amount of iodine-containing promoters present in the medium being such that I/Ru is greater than or equal to 5.Type: GrantFiled: October 24, 1988Date of Patent: March 5, 1991Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron