Preparing Alicyclic Ring Containing Aldehyde By Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Only Patents (Class 568/444)
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Patent number: 11141366Abstract: Described herein is a stable perfuming composition including a perfume oil, a viscosifying agent including tricyclodecanedimethanol alcohol, and a perfumery carrier including hexylene glycol. Also described herein is the use of hexylene glycol in a composition including tricyclodecanedimethanol alcohol and a perfume oil to prevent the crystallization of the composition.Type: GrantFiled: May 8, 2018Date of Patent: October 12, 2021Assignee: Firmenich SAInventors: Pascal Beaussoubre, Wolfgang Fieber, Aude Daugeron-Jouault
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Patent number: 10829716Abstract: Described herein is a process for preparing a stable perfuming composition including a perfume oil, a viscosifying agent including tricyclodecanedimethanol alcohol, and a perfumery carrier including dipropylene glycol.Type: GrantFiled: May 8, 2018Date of Patent: November 10, 2020Assignee: Firmenich SAInventors: Pascal Beaussoubre, Wolfgang Fieber, Aude Daugeron-Jouault
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Patent number: 10767004Abstract: Compositions containing Tricyclodecane Dimethanol (TCCDM) and at least a second component, wherein the composition is characterized in a gas chromatography (GC) analysis, wherein the TCDDM is eluted at a retention time ranging from 12.4 minutes to 13 minutes, the second component is eluted at a retention time ranging from 11.8 minutes to 12.4 minutes, and the ratio of the area of elution peaks indicating the second component compared to the area of the elution peaks of the TCCDM is between 0.001:1 and 0.04:1. Useful products of the composition include polymers and optical materials.Type: GrantFiled: February 14, 2020Date of Patent: September 8, 2020Assignees: DAIREN CHEMICAL CORPORATION, CHANG CHUN PLASTICS CO., LTD.Inventors: Shih-Feng Chiu, Ching-Jui Huang, Hsing-Yun Wang, June-Yen Chou
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Patent number: 8927776Abstract: The invention relates to a method for hydroformylation of unsaturated compounds such as olefins and alkynes using mixtures of synthesis gas (CO/H2), in which either the unsaturated compounds and a catalyst are heated to a reaction temperature of 60 to 200° C. and the synthesis gas is then added, or the unsaturated compounds and the catalyst are brought into contact with pure CO at normal temperature in a preformation step, then are heated to reaction temperature and on reaching the reaction temperature the CO is replaced by the synthesis gas. The pressure is 1 to 200 bar and the CO:H2 ratio in the synthesis gas is in the range from 1:1 to 50:1. The iridium catalyst used comprises a phosphorus-containing ligand in the iridium:ligand ratio in the range from 1:1 to 1:100. With high catalyst activities and low catalyst use, very high turnover frequencies are achieved.Type: GrantFiled: October 24, 2011Date of Patent: January 6, 2015Assignee: Evonik Degussa GmbHInventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
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Publication number: 20140371405Abstract: Disclosed herein are compositions and methods related to the hydroformylation of cyclododecatriene to form cyclododecatriene trialdehyde, and the conversion of the trialdehyde to the polyphenols of Formula 1: where R, m p and Q are as defined herein. Curable compositions comprising compounds of Formula 1, including powder coating compositions, and methods of curing the compositions are also disclosed.Type: ApplicationFiled: February 22, 2013Publication date: December 18, 2014Inventors: Erich J. Molitor, Robert E. Hefner, JR.
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Publication number: 20140024860Abstract: The invention relates to a method for hydroformylation of unsaturated compounds such as olefins and alkynes using mixtures of synthesis gas (CO/H2), in which either the unsaturated compounds and a catalyst are heated to a reaction temperature of 60 to 200° C. and the synthesis gas is then added, or the unsaturated compounds and the catalyst are brought into contact with pure CO at normal temperature in a preformation step, then are heated to reaction temperature and on reaching the reaction temperature the CO is replaced by the synthesis gas. The pressure is 1 to 200 bar and the CO:H2 ratio in the synthesis gas is in the range from 1:1 to 50:1. The iridium catalyst used comprises a phosphorus-containing ligand in the iridium:ligand ratio in the range from 1:1 to 1:100. With high catalyst activities and low catalyst use, very high turnover frequencies are achieved.Type: ApplicationFiled: October 24, 2011Publication date: January 23, 2014Applicant: Evonik Oxeno GmbHInventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
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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: 7683219Abstract: The disclosed is about a hydroformylation of a cyclic olefin with rhodium catalyst, and specifically about the recovering of the rhodium catalyst. Aldehyde and the cyclic olefin are added into a rhodium catalyst solution to process a hydroformylation, thereby forming the product cycloalkyl aldehyde. Afterwards, the result is divided into two layers. The upper layer is substantially rhodium catalyst solution, and the lower layer is substantially cycloalkyl aldehyde and the aldehyde. After separation, the upper layer is reserved to process next hydroformylation reaction with newly added cyclic olefin.Type: GrantFiled: March 23, 2009Date of Patent: March 23, 2010Assignee: Industrial Technology Research InstituteInventors: Mao-Lin Hsueh, Hao-Hsun Yang, Kuo-Chen Shih, Tsai-Tien Su
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Publication number: 20100069678Abstract: The disclosed is about a hydroformylation of a cyclic olefin with rhodium catalyst, and specifically about the recovering of the rhodium catalyst. Aldehyde and the cyclic olefin are added into a rhodium catalyst solution to process a hydroformylation, thereby forming the product cycloalkyl aldehyde. Afterwards, the result is divided into two layers. The upper layer is substantially rhodium catalyst solution, and the lower layer is substantially cycloalkyl aldehyde and the aldehyde. After separation, the upper layer is reserved to process next hydroformylation reaction with newly added cyclic olefin.Type: ApplicationFiled: March 23, 2009Publication date: March 18, 2010Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Mao-Lin HSUEH, Hao-Hsun YANG, Kuo-Chen SHIH, Tsai-Tien SU
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Patent number: 7638656Abstract: The disclosed is about a hydroformylation reaction of a cyclic olefin in the presence of a rhodium catalyst, and specifically about recovering the rhodium catalyst. After the cyclic olefin is hydroformylated by the rhodium catalyst, the product solution is added an extraction liquid including a cycloalkyl alcohol and separated into two layers. The upper layer is substantially made up of the rhodium catalyst solution, and the lower layer is substantially made up of the cycloalkyl aldehyde and the extraction solution including cycloalkyl alcohol.Type: GrantFiled: November 22, 2008Date of Patent: December 29, 2009Assignee: Industrial Technology Research InstituteInventors: Kuo-Chen Shih, Mao-Lin Hsueh, Hao-Hsun Yang
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Publication number: 20090171125Abstract: The disclosed is about a hydroformylation reaction of a cyclic olefin in the presence of a rhodium catalyst, and specifically about recovering the rhodium catalyst. After the cyclic olefin is hydroformylated by the rhodium catalyst, the product solution is added an extraction liquid including a cycloalkyl alcohol and separated into two layers. The upper layer is substantially made up of the rhodium catalyst solution, and the lower layer is substantially made up of the cycloalkyl aldehyde and the extraction solution including cycloalkyl alcohol.Type: ApplicationFiled: November 22, 2008Publication date: July 2, 2009Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Kuo-Chen Shih, Mao-Lin Hsueh, Hao-Hsun Yang
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Patent number: 7321068Abstract: Process for preparing tricyclodecanedialdehyde by hydroformylation of dicyclopentadiene by means of a CO/H2 mixture at elevated temperature and under superatmospheric pressure in the presence of a rhodium catalyst which has not been modified by means of a ligand and is homogeneously dissolved in the hydroformylation medium, wherein the hydroformylation is carried out at a pressure of from 200 to 350 bar in at least two reaction zones, with a reaction temperature of from 80 to 120° C. being set in a first reaction zone and a reaction temperature of from 120 to 150° C. being set in a reaction zone following this reaction zone, with the proviso that the reaction temperature in the subsequent reaction zone is at least 5° C. higher than in the preceding reaction zone.Type: GrantFiled: December 14, 2004Date of Patent: January 22, 2008Assignee: BASF AktiengesellschaftInventors: Rainer Papp, Rocco Paciello, Christoph Benisch
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Patent number: 7122706Abstract: A process for selectively hydroformylating dicyclopentadiene to 8(9)-formyltricyclo-[5.2.1.02,6]dec-3-ene in a heterogeneous reaction system using an aqueous solution of transition metal compounds, containing water-soluble organic phosphorus(III) compounds in complex-bound form, of group VIII of the Periodic Table of the Elements, wherein the water-soluble organic phosphorus(III) compounds are alkali metal or alkaline earth metal salts of sulfonated arylphosphines and aryldiphosphines.Type: GrantFiled: October 19, 2004Date of Patent: October 17, 2006Assignee: Celanese Chemicals Europe GmbHInventors: Peter Lappe, Helmut Springer, Rainer Lukas
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Patent number: 7081554Abstract: The Oxo Process that recycles its cobalt primarily as cobalt salt is improved by concentration of the cobalt salt solution from the demetalling section and the addition of a separation step for organic acid and water. This allows for a higher reuse of acid in the process and thus a lower amount of acid in the waste water. Injecting a higher concentration of cobalt salt solution to the reaction section also reduces the requirement for cobalt source.Type: GrantFiled: March 28, 2003Date of Patent: July 25, 2006Assignee: ExxonMobil Chemical Patent Inc.Inventors: Ronald D. Garton, James T. Ritchie, Raphael Frans Caers
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Patent number: 7081553Abstract: The Cobalt Flash Process is modified by replacing formic acid with acetic acid as process acid. Efficiency using acetic acid as process acid is achieved by two improvements which may be added separately and independently: (1) separation of acetic acid and water from the condensate distilled off in the cobalt salt concentration stage; and (2) removal of formic acid from the system by reaction with the product alcohol in the preformer.Type: GrantFiled: March 28, 2003Date of Patent: July 25, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Dominic T. Clausi, Eddy T. van Driessche, Ronald D. Garton, James T. Ritchie, Nico A. de Munck
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Patent number: 7015362Abstract: A process for preparing 3(4),8(9)-bisformyltricyclo[5.2.1.02.6]decane by hydroformylating dicyclopentadiene with subsequent distillation wherein the hydroformylation of dicyclopentadiene is carried out in two stages, and, in the first hydroformylation stage, the reaction is effected in a heterogeneous reaction system using an aqueous solution of transition metal compounds, containing water-soluble organic phosphorus (III) compounds in complex-bound form, of group VIII of the Period Table of the Elements to give 8(9)-bisformyltricyclo[5.2.1.02.6]dec-3-ene, and, in a second hydroformylation stage, the thus obtained 8(9)-bisformyltricyclo[5.2.1.02.6]dec-3-ene is converted, in homogeneous organic phase in the presence of transition metal compounds of group VIII of the Periodic Table of the Elements to 3(4),8(9)-bisformyltricyclo[5.2.1.02.6]decane.Type: GrantFiled: October 18, 2004Date of Patent: March 21, 2006Assignee: Celanese Chemicals Europe GmbHInventors: Peter Lappe, Helmut Springer, Rainer Lukas
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Patent number: 7015361Abstract: Olefins having at least 6 carbon atoms are hydroformylated in the presence of a homogeneous catalyst in a continuous process in which a) a vertical tall cylindrical reactor (1) whose interior space is divided by means of internals (2) into at least two reaction chambers which extend essentially in the longitudinal direction of the reactor is used, b) at least one olefin is introduced into the reactor together with synthesis gas at the lower end of the first reaction chamber, c) a partially reacted reaction mixture is conveyed from the upper end of a reaction chamber to the lower end of a next reaction chamber; and d) the hydroformylated olefin is taken off at the upper end of the last reaction chamber. The process allows a high conversion at a given reactor volume.Type: GrantFiled: February 13, 2002Date of Patent: March 21, 2006Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Michael Nilles
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Patent number: 7002044Abstract: A microemulsion containing water, a densified fluid, a surfactant, and an organometallic catalyst is used to catalyze chemical reactions. The organometallic catalyst preferably has substantial solubility in the water phase of the microemulsion. Separation of reaction products from the microemulsion is facilitated by removal of the densified fluid.Type: GrantFiled: August 15, 2003Date of Patent: February 21, 2006Assignee: The University of ConnecticutInventors: Can Erkey, Xing Dong
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Patent number: 6960695Abstract: A hydroformylation process comprising reacting a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of a cobalt catalyst, the hydroformylation process being carried out in one or more reactors, at least one of which comprises a gas cap region and a liquid-containing region while in use, characterized in that a sulphur-containing additive is present on the inside walls of the gas cap region of the at least one-reactor which comprises a gas cap region and a liquid-containing region. The sulphur-containing additive suppresses the formation of methane during the hydroformylation process.Type: GrantFiled: October 31, 2003Date of Patent: November 1, 2005Assignee: Shell Oil CompanyInventors: Robert Hardy Ellison, Eric Kragtwijk, Frederik Hendrik Van Der Steen
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Patent number: 6849769Abstract: Essentially monounsaturated polyalkylenes having from 30 to 700 carbon atoms are continuously hydroformylated by a process in which i) a hydroformylation-active cobalt carbonyl catalyst is prepared from a catalyst precursor dissolved in an aqueous phase in the absence of the polyalkylenes, ii) the polyalkylenes are hydroformylated by means of synthesis gas in the presence of the cobalt carbonyl catalyst in a reaction zone, iii) the cobalt carbonyl catalyst is separated from the output from the reaction zone with at least partial reformation of the catalyst precursor and the catalyst precursor is recirculated to step i).Type: GrantFiled: September 11, 2001Date of Patent: February 1, 2005Assignee: BASF AktiengesellschaftInventors: Michael Röper, Heinrich-Josef Blankertz, Armin Volker Grenacher, Roland Krokoszinski, Willi Schönmann
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Patent number: 6723884Abstract: Olefins having from 6 to 20 carbon atoms are hydroformylated by means of a continuous process in which a) an aqueous cobalt(II) salt solution is brought into intimate contact with hydrogen and carbon monoxide to form a hydroformylation-active cobalt catalyst, and the aqueous phase comprising the cobalt catalyst is brought into intimate contact with the olefins and, if desired, an organic solvent and also hydrogen and carbon monoxide in at least one reaction zone where the cobalt catalyst is extracted into the organic phase and the olefins are hydroformylated, b) the output from the reaction zone is treated with oxygen in the presence of acidic aqueous cobalt(II) salt solution, with the cobalt catalyst being decomposed to form cobalt(II) salts and these being backextracted into the aqueous phase; and the phases are subsequently separated, c) the aqueous cobalt(II) salt solution is recirculated in unchanged form to step a), wherein the cobalt(II) salt solution has a concentration of from 1.1 to 1.Type: GrantFiled: February 19, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Armin Volker Grenacher, Hans Stepp
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Patent number: 6720457Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.Type: GrantFiled: July 24, 2002Date of Patent: April 13, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
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Patent number: 6680414Abstract: The present invention provides a process, which includes: in a homogeneous liquid phase including water, and over a fixed-bed catalyst, continuously hydrogenating at least one hydroformylation product obtained from a hydroformylation of one or more C4-16 olefins to produce at least one output mixture; wherein the fixed-bed catalyst includes at least one element of transition group eight of the Periodic Table of the Elements; wherein the output mixture includes at least one corresponding alcohol and from 0.05 to 10% by weight of water; and wherein in a steady-state operation of the process, from 3 to 50% more hydrogen is fed to the hydrogenation than is consumed by the hydrogenation.Type: GrantFiled: December 14, 2001Date of Patent: January 20, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
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Patent number: 6639114Abstract: Ethylenically unsaturated compounds are hydroformylated in the presence of a hydroformylation catalyst comprising at least one complex of a metal of transition group VIII with at least one phosphorus-containing compound as ligand, where this compound contains two groups which contain P atoms and are bound to a molecular skeleton derived from bisphenol A.Type: GrantFiled: February 13, 2002Date of Patent: October 28, 2003Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Jarl Ivar van der Vlugt
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Patent number: 6559344Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one complex or compound of a metal of transition group VIII with at least one bidentate phosphine ligand is used as hydroformylation catalyst and at least one of the reaction steps following the hydroformylation reaction is carried out essentially in the absence of carbon monoxide and hydrogen and in the presence of at least one monodentate phosphine ligand.Type: GrantFiled: February 19, 2002Date of Patent: May 6, 2003Assignee: BASF AktiengesellschaftInventor: Thomas Mackewitz
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Patent number: 6365782Abstract: A method of producing tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde by the hydroformylation of dicyclopentadiene and/or tricyclopentadiene. The tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde in the hydroformylation product liquid are extracted with an extraction solvent comprising a polyhydric alcohol having 2 to 6 carbon atoms. With such extraction, the tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde transfer into the extraction solvent while retaining the catalyst components in the hydroformylation solvent. The controlled extraction atmosphere with an oxygen concentration of 1000 ppm or lower prevents the rhodium compound from transferring into the extraction solvent, thereby avoiding the loss of expensive rhodium.Type: GrantFiled: July 3, 2000Date of Patent: April 2, 2002Assignee: Mitsbushi Gas Chemical Company, Inc.Inventors: Kenichi Nakamura, Kazuhiro Yamada, Takashi Fujii, Takashi Motoi
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Patent number: 6353141Abstract: Functionalized cyclopentene-derived oligomer mixtures are prepared by reacting oligomer mixtures which contain ethyleneic double bonds in one or more reaction steps starting from cyclopentene-derived oligomer mixtures of the formula I R1R2C═[═CH—(CH2)3—CH═]n═CR3R4 (I) where n is an integer from 1 to 15, and R1, R2, R3 and R4 are, independently of one another, hydrogen or alkyl, and are used as described.Type: GrantFiled: June 21, 1999Date of Patent: March 5, 2002Assignee: BASF AktiengesellschaftInventors: Edgar Zeller, Gerhard Schulz, Bernhard Geissler, Michael Röper, Guido Voit
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Publication number: 20010039363Abstract: In an improved process for hydroformylation of olefinically unsaturated compounds using a catalyst based on cobalt and/or rhodium employed in a two-phase medium, a catalyst based on cobalt and/or rhodium is used dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C., in which the aldehydes formed are slightly soluble or insoluble. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion. At the end of the reaction, the organic phase is generally separated and the ionic non-aqueous solvent phase containing the catalyst can be re-used.Type: ApplicationFiled: December 7, 2000Publication date: November 8, 2001Inventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
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Patent number: 6271193Abstract: Described are carbon-containing functional groups substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, process for processes for preparing same, and uses thereof. The 4,5,6,7-tetrahydro-polyalkylated-4-indanes have the generic structure: Wherein G and R1-5 are as defined in the specification. The aforementioned materials have fragrance properties or are intermediates for materials which have fragrance properties. Also described are processes for producing the aforementioned substances.Type: GrantFiled: October 11, 2000Date of Patent: August 7, 2001Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Richard A. Weiss, Anthony T. Levorse, Jr., Howard H. Heinsohn, Jr., Charles E. J. Beck, Marie R. Hanna
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Patent number: 5919987Abstract: An industrial preparation of aldehydes and/or alcohols from olefins of more than 3 carbon atoms by a catalytic hydroformylation of the olefin reactant at a pressure of from 50 to 1000 bar and a temperature of from 50 to 180.degree. C. in the presence of an uncomplexed rhodium catalyst homogeneously dissolved in the reaction medium. The catalytic activity of the rhodium is maintained, first by extracting it from the initially discharged reaction mixture by means of an aqueous solution of a nitrogen-containing complexing agent such as sulfonated or carboxylated pyridines, quinolines or the like. In a recycle of the complexed rhodium to be reused in the hydroformylation reaction, the aqueous rhodium-containing extract is fed to a precarbonylation stage where it subjected to a required precarbonylation in the presence of an essentially water-insoluble organic liquid and in the presence of carbon monoxide, synthesis gas or another gas mixture containing carbon monoxide at from 50 to 1000 bar and from 50 to 180.Type: GrantFiled: September 13, 1996Date of Patent: July 6, 1999Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Maik Aron, Frank-Michael Korgitzsch, Michael Nilles, Wolfgang Harder, Michael Roper, Rocco Paciello
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Patent number: 5910600Abstract: A bisphosphite compound of the following formula (A): ##STR1## wherein --Ar--Ar-- is a bisarylene group represented by any one of the formulae (A-I) to (A-III) defined in the specification, and each of Z.sub.1 to Z.sub.4 is a C.sub.4-20 aromatic or heteroaromatic group which may have a substituent, wherein each of substituents on carbon atoms of an aromatic ring adjacent to the carbon atom bonded to the oxygen atom in each of Z.sub.1 to Z.sub.4, is a C.sub.0-2 group, and each pair of Z.sub.1 and Z.sub.2, and Z.sub.3 and Z.sub.4, are not bonded to each other.Type: GrantFiled: April 28, 1997Date of Patent: June 8, 1999Assignee: Mitsubishi Chemical CorporationInventors: Hisao Urata, Hiroaki Itagaki, Eitaro Takahashi, Yasuhiro Wada, Yoshiyuki Tanaka, Yasukazu Ogino
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Patent number: 5817850Abstract: The synthesis of new sterically hindered ferrocene bis(phosphonites) of formula I ##STR1## the synthesis of the corresponding transition-metal complexes and the use of these complexes in transition-metal-catalyzed reactions are described.Type: GrantFiled: October 30, 1997Date of Patent: October 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5705167Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: April 26, 1995Date of Patent: January 6, 1998Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 5492887Abstract: It was found that 8-exo-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decane having the constitution and stereochemistry of formula (I) possesses particularly useful olfactory properties which are clearly superior to those of the 8-endo-epimer and which already have an effect if compound (I) is enriched with mixtures of 8-exo- and 8-endo-epimers. Compound (I) can therefore be advantageously used, in pure or enriched form, as a scent or as a component of perfume compositions. To prepare an enriched epimer mixture, a mixture obtained in a known manner (U.S. Pat. No. 3,270,061) and having an exo/endo ratio of 1.45:1 is brought into equilibrium by base catalysis, preferably by the action of alkali hydroxides in alcoholic solution, to give an exo/endo ratio of 5.25:1. Alternatively, the enriched epimer mixture can be prepared starting from 8-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decene-3(4), catalytically hydrogenated for example with palladium coal and then optionally brought into equilibrium.Type: GrantFiled: December 11, 1992Date of Patent: February 20, 1996Assignee: Dragoco Gerberding & Co. GmbHInventors: Ernst-Joachim Brunke, Claus-Hermann Kappey, Bernd Holscher, Hartmut Struwe
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Patent number: 5481045Abstract: Sulfonated diphosphines of the formula ##STR1## in which Ar is m-C.sub.6 H.sub.4 -SO.sub.3 M, M is hydrogen, ammonium, a monovalent metal, or the chemical equivalent of a polyvalent metal; Ph is phenyl; the m's are individually 1 or 2, and the n's are individually 0, 1, or 2. A method of their preparation and the hydroformylation of olefins and olefinically unsaturated compounds using these compounds as a constituent of water-soluble catalyst systems are also disclosed.Type: GrantFiled: May 11, 1994Date of Patent: January 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Rainer Manetsberger, Helmut Bahrmann, Christian Kohlpaintner, Peter Lappe
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Patent number: 5434312Abstract: 1,3-Butadiene is hydroformylated at 60.degree. to 150.degree. C. and 1 to 20 MPa in the presence of an aqueous solution which contains, as catalyst, at least one water-soluble rhodium compound and at least one water-soluble organic phosphine. A pH of 8 to 11 is maintained in the aqueous catalyst solution to increase the selectivity of the reaction with respect to the formation of n-five carbon aldehydes and their secondary products. The latter, in particular, can be hydrogenated to 2-propylheptanol, useful as the alcohol component of phthalic ester plasticizers.Type: GrantFiled: September 2, 1994Date of Patent: July 18, 1995Assignee: Hoechst AktiengesellschaftInventors: Bernhard Fell, Peter Hermanns
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Patent number: 5364950Abstract: This invention provides a process for stabilizing a phosphite ligand against degradation in a homogeneous reaction mixture containing a Group VIII transition metal catalyst and the phosphite ligand, said process comprising adding to the reaction mixture an epoxide in an amount from 0.001 to 5 weight percent based on the total weight of the reaction mixture to reduce the degradation of the ligand.Type: GrantFiled: September 29, 1992Date of Patent: November 15, 1994Assignee: Union Carbide Chimicals & Plastics Technology CorporationInventors: James E. Babin, John M. Maher, Ernst Billig
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Patent number: 5223648Abstract: The hydroformylation of olefins and olefinically unsaturated compounds in the presence of a water-soluble rhodium complex compound Which contains, as a ligand, at least one sulfonated diphosphine, and a catalyst therefor.Type: GrantFiled: August 25, 1992Date of Patent: June 29, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
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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: 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: 4782188Abstract: The invention is a process for the hydroformylation of C.sub.2-4 alkenes, formyl-substituted C.sub.2-4 alkenes, aryl-substituted alkenes, unsaturated norbornane ring-containing compounds, and .alpha.-unsaturated acetals which comprises contacting a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, aryl-substituted alkene, an unsaturated norbornane ring-containing compound or an .alpha.-unsaturated acetal in a polar organic solvent with water and carbon monoxide in the presence of a catalytic amount of a catalyst which comprises a mixture of (a) an alkali metal iron carbonyl or alkaline earth metal iron carbonyl which corresponds to the formula M.sub.a Fe.sub.x (CO).sub.y and (b) iron pentacarbonyl under conditions such that an alcohol or aldehyde derivative of a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, an aryl-substituted alkene, unsaturated norbornane ring-containing compound or an .alpha.Type: GrantFiled: November 14, 1983Date of Patent: November 1, 1988Assignee: The Dow Chemical CompanyInventor: Susan B. Butts
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Patent number: 4604232Abstract: Described are the compounds defined according to the generic structure: ##STR1## wherein R represents hydrogen or methyl and one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds. Also described are mixtures of methyl-substituted cyclohexenyl acetaldehydes defined according to the structure: ##STR2## a sub-genus of the genus having the structure: ##STR3## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond and R represents hydrogen or methyl, and uses thereof in augmenting or enhancing the aroma or taste of consumable materials, including perfume compositions, colognes, perfumed articles, perfumed polymers, foodstuffs, chewing gums, medicinal products and toothpastes.Type: GrantFiled: March 15, 1985Date of Patent: August 5, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus J. Wiegers, Manfred H. Vock
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Patent number: 4599468Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.Type: GrantFiled: June 14, 1985Date of Patent: July 8, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4584409Abstract: Described are tertiary hydroxyl carboxaldehydes defined according to the generic structure: ##STR1## wherein the lines ##STR2## represent covalent carbon-carbon bonds when m does not=0; and wherein the lines ##STR3## do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1; wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines ##STR4## represents carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line ##STR5## represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines ##STR6## represent carbon-carbon bonds and with the line ##STR7## representing no bond; and wherein when m is 0, X represents an alkylene moiety, processes for preparing same by means of reacting carbon monoxide and hydrogen with an unsaturated tertiary alcohol defined according to the structure: ##STR8## by means of an oxo reaction, andType: GrantFiled: March 8, 1985Date of Patent: April 22, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4532364Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.Type: GrantFiled: September 19, 1983Date of Patent: July 30, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4528404Abstract: Certain triarylphosphine rhodium carbonyl hydride complexes(Ar.sub.3 P).sub.3 Rh(CO)H (I) and (Ar.sub.3 P).sub.2 Rh(CO).sub.2 H (II)are selective and stable catalysts of high temperature olefin hydroformylation. The critical factors are the maintenance of a sufficient CO partial pressure, above 25 psia, and the provision of a high excess of triarylphosphine ligand concentration, at a minimum of 1 mole per kg. To provide a high ratio of n- to i-aldehyde products of 1-olefin hydroformylation, the concentration of the tris-phosphine complex (I) is maximized. In a continuous product flashoff operation of the present process, the major high boiling solvent components are the excess phosphine ligands and monoalcohol and monoester by-products.A combined isomerization-hydroformylation process is also disclosed for the selective conversion of internal linear olefins to terminal n-aldehydes. In this process, the concentration of the bis-phosphine complex (II) is minimized.Type: GrantFiled: October 23, 1984Date of Patent: July 9, 1985Assignee: Exxon Research and Engineering Co.Inventors: Alexis A. Oswald, Joseph S. Merola, John C. Reisch, Rodney V. Kastrup
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Patent number: 4521634Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.Type: GrantFiled: January 26, 1984Date of Patent: June 4, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4519943Abstract: Described are 5-alkoxybicyclo[2.2.1]heptane-2-oxypropane derivatives defined according to the structure: ##STR1## (wherein R represents C.sub.1 -C.sub.3 alkyl and wherein Z represents one of the moieties, carbinol having the structure: ##STR2## or carboxaldehyde having the structure: ##STR3## and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations, perfumed polymers and the like).Type: GrantFiled: September 26, 1983Date of Patent: May 28, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber, Patrick Whelan, Marie R. Hanna
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Patent number: 4518805Abstract: Described herein is a process for the conversion of hydroperoxides, present in allyl-alkyl ethers to products including .alpha.,.beta.-unsaturated aldehydes and for reducing such .alpha.,.beta.-unsaturated aldehydes to alcohols prior to the use of the ether as a feedstock in a hydroformylation reaction to produce the corresponding ether aldehyde. The process involves contacting the ether with a metal hydride, either in aqueous solution and/or by means of an ion exchange resin. Such treatment decomposes the hydroperoxides and then reduces their .alpha.,.beta.-unsaturated aldehyde decomposition products, thereby reducing the catalyst inhibition period present in the hydroformylation reaction which is observed when such .alpha.,.beta.-unsaturated aldehyde impurities are present.Type: GrantFiled: February 14, 1983Date of Patent: May 21, 1985Assignee: Union Carbide CorporationInventors: Anthony G. Abatjoglou, David R. Bryant
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Patent number: RE37947Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: January 5, 2000Date of Patent: December 31, 2002Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Phillippe Nedoncelle