Preparing Alicyclic Ring Containing Aldehyde By Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Only Patents (Class 568/444)
  • Patent number: 11141366
    Abstract: 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: Grant
    Filed: May 8, 2018
    Date of Patent: October 12, 2021
    Assignee: Firmenich SA
    Inventors: Pascal Beaussoubre, Wolfgang Fieber, Aude Daugeron-Jouault
  • Patent number: 10829716
    Abstract: 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: Grant
    Filed: May 8, 2018
    Date of Patent: November 10, 2020
    Assignee: Firmenich SA
    Inventors: Pascal Beaussoubre, Wolfgang Fieber, Aude Daugeron-Jouault
  • Patent number: 10767004
    Abstract: 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: Grant
    Filed: February 14, 2020
    Date of Patent: September 8, 2020
    Assignees: DAIREN CHEMICAL CORPORATION, CHANG CHUN PLASTICS CO., LTD.
    Inventors: Shih-Feng Chiu, Ching-Jui Huang, Hsing-Yun Wang, June-Yen Chou
  • Patent number: 8927776
    Abstract: 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: Grant
    Filed: October 24, 2011
    Date of Patent: January 6, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
  • Publication number: 20140371405
    Abstract: 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: Application
    Filed: February 22, 2013
    Publication date: December 18, 2014
    Inventors: Erich J. Molitor, Robert E. Hefner, JR.
  • Publication number: 20140024860
    Abstract: 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: Application
    Filed: October 24, 2011
    Publication date: January 23, 2014
    Applicant: Evonik Oxeno GmbH
    Inventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
  • Publication number: 20110028746
    Abstract: 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 c
    Type: Application
    Filed: March 25, 2009
    Publication date: February 3, 2011
    Applicant: BASF SE
    Inventors: Jens Rudolph, Joachim Schmidt-Leithoff, Rocco Paciello, Bernhard Breit, Thomas Smejkal
  • Patent number: 7683219
    Abstract: 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: Grant
    Filed: March 23, 2009
    Date of Patent: March 23, 2010
    Assignee: Industrial Technology Research Institute
    Inventors: Mao-Lin Hsueh, Hao-Hsun Yang, Kuo-Chen Shih, Tsai-Tien Su
  • Publication number: 20100069678
    Abstract: 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: Application
    Filed: March 23, 2009
    Publication date: March 18, 2010
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Mao-Lin HSUEH, Hao-Hsun YANG, Kuo-Chen SHIH, Tsai-Tien SU
  • Patent number: 7638656
    Abstract: 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: Grant
    Filed: November 22, 2008
    Date of Patent: December 29, 2009
    Assignee: Industrial Technology Research Institute
    Inventors: Kuo-Chen Shih, Mao-Lin Hsueh, Hao-Hsun Yang
  • Publication number: 20090171125
    Abstract: 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: Application
    Filed: November 22, 2008
    Publication date: July 2, 2009
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Kuo-Chen Shih, Mao-Lin Hsueh, Hao-Hsun Yang
  • Patent number: 7321068
    Abstract: 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: Grant
    Filed: December 14, 2004
    Date of Patent: January 22, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Papp, Rocco Paciello, Christoph Benisch
  • Patent number: 7122706
    Abstract: 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: Grant
    Filed: October 19, 2004
    Date of Patent: October 17, 2006
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Peter Lappe, Helmut Springer, Rainer Lukas
  • Patent number: 7081554
    Abstract: 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: Grant
    Filed: March 28, 2003
    Date of Patent: July 25, 2006
    Assignee: ExxonMobil Chemical Patent Inc.
    Inventors: Ronald D. Garton, James T. Ritchie, Raphael Frans Caers
  • Patent number: 7081553
    Abstract: 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: Grant
    Filed: March 28, 2003
    Date of Patent: July 25, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Dominic T. Clausi, Eddy T. van Driessche, Ronald D. Garton, James T. Ritchie, Nico A. de Munck
  • Patent number: 7015361
    Abstract: 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: Grant
    Filed: February 13, 2002
    Date of Patent: March 21, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Michael Nilles
  • Patent number: 7015362
    Abstract: 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: Grant
    Filed: October 18, 2004
    Date of Patent: March 21, 2006
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Peter Lappe, Helmut Springer, Rainer Lukas
  • Patent number: 7002044
    Abstract: 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: Grant
    Filed: August 15, 2003
    Date of Patent: February 21, 2006
    Assignee: The University of Connecticut
    Inventors: Can Erkey, Xing Dong
  • Patent number: 6960695
    Abstract: 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: Grant
    Filed: October 31, 2003
    Date of Patent: November 1, 2005
    Assignee: Shell Oil Company
    Inventors: Robert Hardy Ellison, Eric Kragtwijk, Frederik Hendrik Van Der Steen
  • Patent number: 6849769
    Abstract: 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: Grant
    Filed: September 11, 2001
    Date of Patent: February 1, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Röper, Heinrich-Josef Blankertz, Armin Volker Grenacher, Roland Krokoszinski, Willi Schönmann
  • Patent number: 6723884
    Abstract: 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: Grant
    Filed: February 19, 2002
    Date of Patent: April 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Armin Volker Grenacher, Hans Stepp
  • Patent number: 6720457
    Abstract: 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: Grant
    Filed: July 24, 2002
    Date of Patent: April 13, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
  • Patent number: 6680414
    Abstract: 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: Grant
    Filed: December 14, 2001
    Date of Patent: January 20, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
  • Patent number: 6639114
    Abstract: 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: Grant
    Filed: February 13, 2002
    Date of Patent: October 28, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Jarl Ivar van der Vlugt
  • Patent number: 6559344
    Abstract: 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: Grant
    Filed: February 19, 2002
    Date of Patent: May 6, 2003
    Assignee: BASF Aktiengesellschaft
    Inventor: Thomas Mackewitz
  • Patent number: 6365782
    Abstract: 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: Grant
    Filed: July 3, 2000
    Date of Patent: April 2, 2002
    Assignee: Mitsbushi Gas Chemical Company, Inc.
    Inventors: Kenichi Nakamura, Kazuhiro Yamada, Takashi Fujii, Takashi Motoi
  • Patent number: 6353141
    Abstract: 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: Grant
    Filed: June 21, 1999
    Date of Patent: March 5, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Edgar Zeller, Gerhard Schulz, Bernhard Geissler, Michael Röper, Guido Voit
  • Publication number: 20010039363
    Abstract: 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: Application
    Filed: December 7, 2000
    Publication date: November 8, 2001
    Inventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
  • Patent number: 6271193
    Abstract: 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: Grant
    Filed: October 11, 2000
    Date of Patent: August 7, 2001
    Assignee: 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
  • Patent number: 5919987
    Abstract: 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: Grant
    Filed: September 13, 1996
    Date of Patent: July 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Maik Aron, Frank-Michael Korgitzsch, Michael Nilles, Wolfgang Harder, Michael Roper, Rocco Paciello
  • Patent number: 5910600
    Abstract: 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: Grant
    Filed: April 28, 1997
    Date of Patent: June 8, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hisao Urata, Hiroaki Itagaki, Eitaro Takahashi, Yasuhiro Wada, Yoshiyuki Tanaka, Yasukazu Ogino
  • Patent number: 5817850
    Abstract: 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: Grant
    Filed: October 30, 1997
    Date of Patent: October 6, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum
  • Patent number: 5705167
    Abstract: 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: Grant
    Filed: April 26, 1995
    Date of Patent: January 6, 1998
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5492887
    Abstract: 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: Grant
    Filed: December 11, 1992
    Date of Patent: February 20, 1996
    Assignee: Dragoco Gerberding & Co. GmbH
    Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey, Bernd Holscher, Hartmut Struwe
  • Patent number: 5481045
    Abstract: 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: Grant
    Filed: May 11, 1994
    Date of Patent: January 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang A. Herrmann, Rainer Manetsberger, Helmut Bahrmann, Christian Kohlpaintner, Peter Lappe
  • Patent number: 5434312
    Abstract: 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: Grant
    Filed: September 2, 1994
    Date of Patent: July 18, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernhard Fell, Peter Hermanns
  • Patent number: 5364950
    Abstract: 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: Grant
    Filed: September 29, 1992
    Date of Patent: November 15, 1994
    Assignee: Union Carbide Chimicals & Plastics Technology Corporation
    Inventors: James E. Babin, John M. Maher, Ernst Billig
  • Patent number: 5223648
    Abstract: 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: Grant
    Filed: August 25, 1992
    Date of Patent: June 29, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
  • Patent number: 5099047
    Abstract: 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: Grant
    Filed: November 13, 1990
    Date of Patent: March 24, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Yuji Kawaragi
  • Patent number: 4788325
    Abstract: 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: Grant
    Filed: May 29, 1987
    Date of Patent: November 29, 1988
    Assignee: National Distillers and Chemical Corporation
    Inventor: Biau-Hung Chang
  • Patent number: 4782188
    Abstract: 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: Grant
    Filed: November 14, 1983
    Date of Patent: November 1, 1988
    Assignee: The Dow Chemical Company
    Inventor: Susan B. Butts
  • Patent number: 4604232
    Abstract: 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: Grant
    Filed: March 15, 1985
    Date of Patent: August 5, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus J. Wiegers, Manfred H. Vock
  • Patent number: 4599468
    Abstract: 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: Grant
    Filed: June 14, 1985
    Date of Patent: July 8, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4584409
    Abstract: 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, and
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: April 22, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4532364
    Abstract: 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: Grant
    Filed: September 19, 1983
    Date of Patent: July 30, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4528404
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: July 9, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Alexis A. Oswald, Joseph S. Merola, John C. Reisch, Rodney V. Kastrup
  • Patent number: 4521634
    Abstract: 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: Grant
    Filed: January 26, 1984
    Date of Patent: June 4, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4519943
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: May 28, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber, Patrick Whelan, Marie R. Hanna
  • Patent number: 4518805
    Abstract: 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: Grant
    Filed: February 14, 1983
    Date of Patent: May 21, 1985
    Assignee: Union Carbide Corporation
    Inventors: Anthony G. Abatjoglou, David R. Bryant
  • Patent number: RE37947
    Abstract: 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: Grant
    Filed: January 5, 2000
    Date of Patent: December 31, 2002
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Phillippe Nedoncelle