Isomerization Patents (Class 568/450)
  • Patent number: 9284246
    Abstract: A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed.
    Type: Grant
    Filed: September 6, 2013
    Date of Patent: March 15, 2016
    Assignee: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Hideo Ujihara, Mitsuhiko Fujiwhara
  • Patent number: 9193655
    Abstract: Provided is a method for highly selectively producing 7-octenal with a high conversion ratio through the isomerization reaction of 2,7-octadiene-1-ol. Specifically, provided is a method for producing 7-octenal, in which a copper-based catalyst is obtained by reducing a copper-based catalyst precursor described below, and an isomerization reaction of 2,7-octadiene-1-ol is caused in a gas phase using a fixed-bed reaction in the presence of the obtained copper-based catalyst. The copper-based catalyst precursor: a copper-based catalyst precursor obtained by calcining a mixture containing copper, iron, aluminum, and calcium silicate in which an atomic ratio of iron and aluminum to copper [(Fe+Al)/Cu] is in a range of 1.71 to 2.5, an atomic ratio of aluminum to iron [Al/Fe] is in a range of 0.001 to 3.3, and calcium silicate is contained in a range of 15% by mass to 65% by mass at a temperature in a range of 500° C. to 1,000° C.
    Type: Grant
    Filed: August 30, 2013
    Date of Patent: November 24, 2015
    Assignee: KURARAY CO., LTD.
    Inventor: Tomoaki Tsuji
  • Patent number: 8884070
    Abstract: Provided is a process for producing an aldehyde from an alkylene. The process includes (a) photocatalytically dehydrogenating at least one alkane to obtain a mixture comprising at least one olefin and hydrogen, (b) adding carbon dioxide and hydrogen to the mixture, and (c) hydroformylating the olefin to at least one aldehyde. The process also includes converting carbon dioxide and hydrogen into water and carbon monoxide prior to the hydroformylating. In addition, the conversion of carbon dioxide and hydrogen into water and carbon monoxide is performed by a reverse water gas shift reaction.
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: November 11, 2014
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Robert Franke, Dirk Fridag, Bart Hamers, Horst-Werner Zanthoff, Matthias Blug, Julia Strautmann, Stefan Nordhoff
  • Patent number: 8871745
    Abstract: The present invention provides novel compounds useful as proteasome inhibitors. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.
    Type: Grant
    Filed: August 12, 2013
    Date of Patent: October 28, 2014
    Assignee: Millennium Pharmaceuticals, Inc.
    Inventors: Edward J. Olhava, Mihaela Diana Danca
  • Publication number: 20140051759
    Abstract: The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
    Type: Application
    Filed: September 17, 2012
    Publication date: February 20, 2014
    Inventors: John L. Gainer, Raymond C. Grabiak
  • Patent number: 8404902
    Abstract: The invention relates to a method for separating 1-butene from C4-containing hydrocarbon mixtures, comprising isobutene and 1-butene, by hydroformylation, wherein the catalytic system used is made of one of the transition metals of the group 8 to 10, preferably rhodium, and a bisphosphite ligand of the formula (I), where X is a divalent substituted or unsubstituted bisalkylene or bisarylene group having one or more heteroatom(s), Y is a divalent substituted or unsubstituted bisarylene or bisalkylene group having one or more heteroatom(s), Z is oxygen or NR9, and R1, R2, R3, R4 are identical or different, substituted or unsubstituted, linked, unlinked or condensed aryl or heteroaryl groups, and R9 is hydrogen or a substituted or unsubstituted alkyl or aryl group having one or more heteroatom(s), wherein the bisphosphite ligand of the formula (I) is used in an excess of a molar ratio of 100:1 to 1:1 to the transition metal, and that with a 1-butene conversion of more than 95% less than 5% of the present isobute
    Type: Grant
    Filed: April 28, 2009
    Date of Patent: March 26, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
  • Publication number: 20110071321
    Abstract: The invention relates to a method for separating 1-butene from C4-containing hydrocarbon mixtures, comprising isobutene and 1-butene, by hydroformylation, wherein the catalytic system used is made of one of the transition metals of the group 8 to 10, preferably rhodium, and a bisphosphite ligand of the formula (I), where X is a divalent substituted or unsubstituted bisalkylene or bisarylene group having one or more heteroatom(s), Y is a divalent substituted or unsubstituted bisarylene or bisalkylene group having one or more heteroatom(s), Z is oxygen or NR9, and R1, R2, R3, R4 are identical or different, substituted or unsubstituted, linked, unlinked or condensed aryl or heteroaryl groups, and R9 is hydrogen or a substituted or unsubstituted alkyl or aryl group having one or more heteroatom(s), wherein the bisphosphite ligand of the formula (I) is used in an excess of a molar ratio of 100:1 to 1:1 to the transition metal, and that with a 1-butene conversion of more than 95% less than 5% of the present isobute
    Type: Application
    Filed: April 28, 2009
    Publication date: March 24, 2011
    Applicant: EVONIK OXENO GMBH
    Inventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
  • Publication number: 20100048959
    Abstract: The present invention relates to a process for preparing hydroformylation products of olefins having at least four carbon atoms, in which a high proportion of both the linear Ci-olefins having a terminal double bond comprised in the olefin-comprising feed used and of the linear Ci-olefins having an internal double bond is converted into hydroformylation products. Furthermore, the invention relates to a process for preparing 2-propylheptanol which comprises such a hydroformylation process.
    Type: Application
    Filed: November 29, 2007
    Publication date: February 25, 2010
    Applicant: BASF SE
    Inventors: Marcus Sigl, Frank Poplow, Rainer Papp, Thomas Mackewitz, Dag Wiebelhaus, Rocco Paciello, Thomas Heldemann, Frank Heimann, Stefan Bitterlich, Martin Volland, Sven Crone, Christoph Obler
  • Patent number: 7348459
    Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethybutanol. 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 converted 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
    Type: Grant
    Filed: October 24, 2006
    Date of Patent: March 25, 2008
    Assignee: The Nutrasweet Company
    Inventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
  • Patent number: 6909019
    Abstract: A process is disclosed for preparing aldehydes by isomerization of the corresponding unsaturated primary alcohols using a transition metal catalyst system, in an alcoholic solvent and in the presence of an acid. An aldehyde forms by isomerizing an unsaturated primary alcohol under conditions that protect the newly formed aldehyde as a dialkylacetal in situ during the reaction. Protecting the aldehyde as an acetal allows for facile separation of the product from the catalyst as well as effectively driving the reaction toward completion.
    Type: Grant
    Filed: May 25, 2004
    Date of Patent: June 21, 2005
    Assignee: Eastman Chemical Company
    Inventor: Sheryl Davis Debenham
  • Patent number: 6573409
    Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis 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: Grant
    Filed: May 19, 2000
    Date of Patent: June 3, 2003
    Assignee: The Nutrasweet Company
    Inventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
  • Patent number: 6403839
    Abstract: Process for making butyraldehyde from an n-butenyl ester of a carboxylic acid, wherein the n-butenyl ester is hydrolyzed to form the corresponding n-butenyl alcohol n-butenyl alcohol so produced is isomerized to form butyraldehyde.
    Type: Grant
    Filed: June 12, 2001
    Date of Patent: June 11, 2002
    Assignee: BP Chemicals Limited
    Inventor: Benjamin Patrick Gracey
  • Patent number: 6329555
    Abstract: Described is a process for preparing substituted butenes of the formula I and/or II, where the radical R is unsubstituted or mono- or di-C1-C10-alkoxy-substituted or mono- or dihydroxy-substituted C2-C20-alkyl or alkenyl or is C6-C10-aryl, C7-C11-aralkyl or methyl by reacting 1,3-butadiene with an alcohol of the formula ROH in which R is as defined in the presence of an acidic particulate catalyst insoluble in the reaction medium, which involves contacting the butadiene, the alcohol and the catalyst in a fluidized bed reactor which is flow-approached from below and is operated at above the loosening point.
    Type: Grant
    Filed: November 2, 1999
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Maik Aron, Ralf Böhling, Peter Zehner
  • Patent number: 6278031
    Abstract: The fixed-bed catalyst comprises palladium and selenium or tellurium or a mixture of selenium and tellurium on a silicon dioxide support and has a BET surface area of from 80 to 380 m2/g and a pore volume of from 0.6 to 0.95 cm3/g in the pore diameter range from 3 nm to 300 &mgr;m, with from 80 to 95% of the pore volume being in the pore diameter range from 10 to 100 nm. It is prepared by impregnating a silicon dioxide support with a solution of a palladium compound and a selenium compound or tellurium compound or a mixture of a selenium compound and a tellurium compound, drying it and reducing it in the presence of hydrogen. The catalyst is used, in particular, for isomerizing 3-buten-1-ol compounds.
    Type: Grant
    Filed: January 16, 2001
    Date of Patent: August 21, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Josef Bröcker, Werner Aquila, Klemens Flick, Gerd Kaibel, Ernst Langguth
  • Patent number: 6239324
    Abstract: The invention provides a chain diene compound with desirable regioselectivity, in the presence of a specific ruthenium compound. This chain diene compound is a promising raw material for terpene. It has a structure represented by the general formula (IX): wherein R1 represents H, a C1-C6 alkyl group which may be substituted or a C2-C6 alkenyl group which may be substituted, R2 represents a phenyl group which may have a C1-C4 alkyl group or a C1-C12 acyloxy group which may have a phenyl group or a naphthyl group, or a benzyl group or R2 is a hydroxy group which reversibly forms an aldehyde group through shifting of the position of the double bond adjacent to said hydroxy group. The chain diene compound is produced by reacting 2-substituted-1,3-butadienes with terminal olefins in the presence of a ruthenium compound in a hydrophilic solvent.
    Type: Grant
    Filed: August 26, 1999
    Date of Patent: May 29, 2001
    Assignee: Takasago International Corporation
    Inventors: Mitsuhiko Fujiwhara, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara, Hisao Iwai, Takashi Miura
  • Patent number: 6198006
    Abstract: A process for the manufacture of citral is provided by the catalyzed rearrangement of dehydrolinalool to citral. The rearrangement is carried out in the presence of a molybdenum compound of the general formula MoO2X2 wherein X signifies an acetylacetonate or halide ion, and a dialkyl or diaryl sulphoxide as the catalyst system, in the presence of an organic acid having a pK value in the range of about 4.0 to about 6.5 and in an apolar aprotic organic solvent.
    Type: Grant
    Filed: March 16, 1999
    Date of Patent: March 6, 2001
    Assignee: Roche Vitamins Inc.
    Inventor: Werner Bonrath
  • Patent number: 6191313
    Abstract: A process for the manufacture of dihydrocitral, a valuable intermediate, through the catalyzed rearrangement of dihydrodehydrolinalool by carrying out the rearrangement in the presence of a molybdenum compound of the general formula MoO2X2 wherein X signifies an acetylacetonate or halide ion, and a dialkyl or diaryl sulphoxide as the catalyst system, in the presence of an organic acid having a pK value in the range of about 4.0 to about 6.5 and in an aprotic organic solvent.
    Type: Grant
    Filed: March 29, 1999
    Date of Patent: February 20, 2001
    Assignee: Roche Vitamins Inc.
    Inventor: Werner Bonrath
  • Patent number: 6166265
    Abstract: Process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-Butadiene or a butadiene-containing hydrocarbon mixture is reacted with an alcohol of the formula IROH I,where R is C.sub.2 -C.sub.20 -alkyl or alkenyl which is unsubstituted or substituted by 1 or 2 C.sub.1 -C.sub.10 -alkoxy or hydroxyl groups, or is C.sub.6 -C.sub.10 -aryl, C.sub.7 -C.sub.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: December 26, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Rocco Paciello, Michael Roper
  • Patent number: 6118027
    Abstract: Unsaturated aldehydes are prepared by mixing propargyl alcohol, a catalyst and a conjugated diolefin and heating the mixture for a time and at a temperature sufficient to form an unsaturated aldehyde. The diolefin may be 2-methylpentadiene, 2(5,5 dimethyl 5 hydroxy pentyl)1,3 butadiene or myrcene. The catalyst may be inorganic, organic, organometallic or mixtures thereof.
    Type: Grant
    Filed: April 20, 1999
    Date of Patent: September 12, 2000
    Assignee: Givaudan Roure (International) SA
    Inventors: Alan John Chalk, Joseph Anthony Virgilio
  • Patent number: 6013843
    Abstract: A process for continuous industrial production of unsaturated aliphatic aldehydes having a boiling range from 95 to 136.degree. C. by oxidative dehydrogenation of the corresponding alcohols with an oxygen-comprising gas over a supported catalyst consisting of copper, silver and/or gold on an inert support in a tube bundle reactor, rapid cooling of the reaction gases and removal of the aldehydes from the resulting condensate with recycling of the unconverted alcohols comprisesa) vaporizing the alcohol,b) admixing the alcohol vapor with an oxygen-comprising gas,c) initially passing the resulting oxygen-comprising alcohol vapor at above the dew point of the alcohol but below the commencement temperature of the reaction through a layer of one of the abovementioned supported catalysts which is at least 0.5 cm in thickness and only thend) reacting the oxygen-comprising alcohol vapor at from 300 to 600.degree. C.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: January 11, 2000
    Assignee: BASF Aktiengeselllschaft
    Inventors: Werner Aquila, Hartwig Fuchs, Otto Worz, Wilhelm Ruppel, Klaus Halbritter
  • Patent number: 5994590
    Abstract: A process for producing 7-octen-1-al by isomerization of 2,7.octadien-1-ol by feeding 2,7-octadien-1-ol and hydrogen to a reaction zone in the presence of a copper catalyst while controlling the molar ratio of 2,7-octadien-1-ol to hydrogen within a range of 99/1 to 75/25, and effecting isomerization in the gaseous phase. This process ensures a high yield, a high selectivity and stable operation over a long period of time.
    Type: Grant
    Filed: September 30, 1998
    Date of Patent: November 30, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Tomoyasu Tsuda, Yasuo Tokitoh, Kazunori Watanabe, Takashi Hori
  • Patent number: 5905175
    Abstract: 1-chloro-3,3-dimethylbutane is oxidized by dimethyl sulfoxide, in the presence of an effective amount of inorganic bromide or iodide, and in the present of an effective amount of base, to produce 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: May 20, 1998
    Date of Patent: May 18, 1999
    Assignee: The NutraSweet Company
    Inventors: Zhi Guo, Indra Prakash
  • Patent number: 5892125
    Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, in whicha) 1,3-butadiene is caused to react with an amine of the formula IR.sup.1 R.sup.2 NH, Iin which R.sup.1 and R.sup.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: April 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Michael Roper, Rocco Paciello, Alfred Thome
  • Patent number: 5856584
    Abstract: This invention provides a method for preparing 3,3-dimethylbutyraldehyde from 3,3-dimethylbutanol using an oxidizing component. In one embodiment, 3,3-dimethylbutanol is oxidized to 3,3-dimethylbutyraldehyde in the vapor phase by contacting it with an oxidizing metal oxide compound. In another embodiment, the oxidation of 3,3-dimethylbutanol is carried out by treating it with 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical and an oxidizing agent in a solvent to produce 3,3-dimethylbutyraldehyde. The method of this invention provides a commercially practicable means of preparing 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: January 5, 1999
    Assignee: The Nutrasweet Company
    Inventors: Indra Prakash, David J. Ager, Alan R. Katritzky
  • Patent number: 5770775
    Abstract: A method is disclosed for preparing 3,3-dimethylbutyraldehyde by isomerization of 3,3-dimethylepoxybutane with a basic lithium salt which in turn may be prepared by oxidation of dimethylbutane. The method provides an economical means of preparing 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: February 10, 1997
    Date of Patent: June 23, 1998
    Assignee: The NutraSweet Company
    Inventors: Alan R. Katritzky, Indra Prakash
  • Patent number: 5705707
    Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-butadiene is caused to react with an alcohol of the formula IROH I,to form a mixture of adducts of the formulas II ##STR1## and III ##STR2## b) the adduct III is isomerized to the adduct II, c) the adduct II is isomerized in the presence of a homogeneous or heterogeneous transition metal element catalyst to form the enol ether of the formula IV ##STR3## and d) n-butyraldehyde and/or n-butanol is/are produced from this ether IV by the reaction thereof with hydrogen and water or water only in the presence of a homogeneous or heterogeneous catalyst.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: January 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Michael Roper, Rolf Pinkos, Rocco Paciello, Alfred Thome
  • Patent number: 5502257
    Abstract: Disclosed is a process for the preparation of cyclopropanecarboxaldehyde by the thermal isomerization of 2,3-dihydrofuran under superatmospheric pressure, e.g., at a temperature of about 300.degree. to 600.degree. C. and a pressure of about 3 to 345 bars absolute.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: March 26, 1996
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Timothy W. Price, Timothy R. Nolen, Daniel B. Compton, David C. Attride
  • Patent number: 5481044
    Abstract: .alpha.-alkyl aldehydes having 8 to 17 carbon atoms are obtained from terminal olefins containing one less carbon atom. The olefins are first isomerized in the presence of iron carbonyl and then, without separating out the iron compound, hydroformylated in the presence of rhodium as catalyst.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: January 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Helmut Springer
  • Patent number: 5312995
    Abstract: A process for isomerizing epoxides to aldehydes is disclosed. The process uses a metal-exchanged zeolite catalyst wherein the zeolite contains an alkali metal and one or more second exchangeable metals from Group IIA, IB, IIB, or IIIB. The catalysts are easily made by combining alkali metal-exchanged zeolites with aqueous solutions that contain halides or nitrates of the second metal. The process is useful for vapor-phase isomerization of propylene oxide to propanal.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: May 17, 1994
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Mahmoud K. Faraj
  • Patent number: 5177258
    Abstract: Biaryl derivatives are produced by coupling an aryl halide in an aqueous alkaline solution in the presence of a palladium catalyst, using formic hydrazide as the reducing agent.
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: January 5, 1993
    Assignee: Bromine Compounds, Ltd.
    Inventors: Abram Becker, Ariel A. Ewenson, Bertha Croitoru
  • Patent number: 5077438
    Abstract: A method of isomerizing propargyl alcohol to acrolein, wherein propargyl alcohol is rearranged in the gas phase at a temperature of from 300.degree. to 550.degree. C. and a pressure of from 0.01 to 50 bar and in contact with a heterogeneous catalyst containing alkaline-reacting metal ions, and the use of propargyl alcohol as a depot substance for the liberation of acrolein.
    Type: Grant
    Filed: February 14, 1991
    Date of Patent: December 31, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Steck, Matthias Schwarzmann, Kurt Weinacht, Franz Merger
  • Patent number: 5012005
    Abstract: 4-oxaaldehydes of the formula ##STR1## are prepared by catalytic isomerization of 1,3-dioxanes by a process in which a 1,3-dioxane of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are identical or different and are each hydrogen, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 18 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, aralkyl, aralkenyl or alkenylaryl radical of 5 to 16 carbon atoms or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 and/or R.sup.4 and R.sup.5 together with the carbon atoms to which they are bonded may form a cycloalkane, a cycloalkene or a heterocyclic structure, and the stated radicals may furthermore carry substituents which are inert under the reaction conditions, and R.sup.3 is hydrogen or straight-chain or branched alkyl, is isomerized using a metal oxide catalyst, which has been treated with an acid, and/or a silica phase having a zeolite structure.
    Type: Grant
    Filed: July 27, 1989
    Date of Patent: April 30, 1991
    Inventors: Wolfgang Hoelderich, Franz Merger
  • Patent number: 4996365
    Abstract: Alkyl-substituted cinnamaldehydes of the formula I ##STR1## where one or more of R.sup.1 , R.sup.2 and R.sup.3 is alkyl of from 1 to 8 carbon atoms, preferably of from 1 to 4 carbon atoms, and non-alkyl R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, which comprises heating acetylene alcohols of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each as defined above, in the presence of from 55 to 98% strength aqueous formic acid.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: February 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Lauterbach, Frank F. Pape, Walter Gramlich
  • Patent number: 4980511
    Abstract: Aldehydes and ketones are prepared from epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each alkyl, alkenyl, aryl, alkoxy or aralkyl and R.sup.3 has the same meanings or is hydrogen, by a catalytic rearrangement reaction in the presence of various catalysts, in particular zeolites of the pentasil type.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: December 25, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Helmut Lermer
  • Patent number: 4950797
    Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
  • Patent number: 4939280
    Abstract: 4-Oxaaldehydes of the formula ##STR1## are prepared by catalytic isomerization of 1,3-dioxanes by a process in which a 1,3-dioxane of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are identical or different and are each hydrogen, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 18 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, aralkyl or alkenylaryl radical of 5 to 16 carbon atoms or a heterocyclic radical, and furthermore R.sup.1 and R.sup.2 and/or R.sup.4 and R.sup.5 together with the carbon atom to which they are bonded may form a cycloalkane, a cycloalkene or a heterocyclic structure, and the stated radicals may furthermore carry substituents which are inert under the reaction conditions, and R.sup.3 is hydrogen or straight-chain or branched alkyl, is isomerized using a phosphate as a catalyst.
    Type: Grant
    Filed: April 29, 1988
    Date of Patent: July 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Helmut Lermer
  • Patent number: 4925987
    Abstract: Crotoaldehyde is produced by contacting butadiene monoxide with a metal oxide, mixed metal oxide, or mixture of metal oxides. The process is preferably conducted in the vapor phase. Other unsaturated aldehydes can be prepared from other unsaturated terminal epoxides.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: May 15, 1990
    Assignee: Eastman Kodak Company
    Inventors: John R. Monnier, Howard M. Low
  • Patent number: 4925986
    Abstract: Crotonaldehyde is produced by contacting 3,4-epoxybutene, i.e. butadiene monoxide, with a halide-containing catalyst such as a hydrogen halide or metal halide. The process is preferably conducted in the vapor phase. Other unsaturated aldehydes can be produced from other unsaturated terminal epoxides.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: May 15, 1990
    Assignee: Eastman Kodak Company
    Inventors: John R. Monnier, Peter J. Muehlbauer, Howard M. Low
  • Patent number: 4749814
    Abstract: Ethylenic carbonyl compounds of formula ##STR1## are made by the isomerization of acetylenic alcohols of formula ##STR2## in the presence of a catalyst consisting of a titanium derivative, a copper or silver derivative, and, if required, an acid, which may be in the form of an ester or anhydride, or an inorganic ester.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 7, 1988
    Assignee: Rhone-Poulenc Sante
    Inventor: Pierre Chabardes
  • Patent number: 4709097
    Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: November 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
  • Patent number: 4677230
    Abstract: 2-Methyl-2-alkenals of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl which may additionally carry aromatic radicals, or an aromatic radical, are prepared by isomerizing a 2-alkylacrolein of the formula ##STR2## in the presence of hydrogen and of a catalyst which contains palladium and an oxide or salt of a rare earth metal as active components, at from 20.degree. to 120.degree. C. and under from 1 to 100 bar.
    Type: Grant
    Filed: June 11, 1986
    Date of Patent: June 30, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Leopold Hupfer, Franz Merger, Franz J. Broecker, Rolf Fischer
  • Patent number: 4605779
    Abstract: A novel method for producing tiglic aldehyde from ethylacrolein by isomerization in the presence of a hydrogenating catalyst is disclosed. According to the invention, tiglic aldehyde can be prepared in a good yield.
    Type: Grant
    Filed: July 24, 1985
    Date of Patent: August 12, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruo Matsuda, Shinkichi Shimizu, Masaaki Iwasa
  • Patent number: 4599458
    Abstract: 2-Methylalk-2-enals of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl or an aromatic radical, are prepared by isomerization of an acrolein derivative of the formula ##STR2## with a zeolite catalyst, an aluminum silicate and/or an aluminum phosphate.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: July 8, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Hans-Martin Weitz
  • Patent number: 4510331
    Abstract: There are disclosed a process for producing 7-octen-1-al which comprises isomerizing 2,7-octadien-1-ol in the presence of a catalyst comprising oxides of at least two metals selected from the group consisting of copper, chromium and zinc and processes for producing derivatives of 7-octen-1-al.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: April 9, 1985
    Assignee: Kuraray Company, Ltd.
    Inventors: Noriaki Yoshimura, Masuhiko Tamura
  • Patent number: 4463196
    Abstract: Citral is prepared by heating dehydrolinalol in the presence of a vanadium compound as catalyst and an alkanol of 12 to 18 carbon atoms as co-catalyst, whereby isomerization is effected. There may also be present an alkanol or cycloalkanol of 7 to 11 carbon atoms as co-catalyst.
    Type: Grant
    Filed: May 8, 1980
    Date of Patent: July 31, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Pierre Chabardes, Emile Kuntz
  • Patent number: 4377708
    Abstract: Vinyl esters such as vinyl acetate are hydrocarboxylated with tertiary organo-phosphine stabilized palladium catalysts utilizing low water concentration; the ready hydrolysis of the .alpha.-acetoxypropionic acid affords a convenient route to lactic acid.
    Type: Grant
    Filed: October 14, 1977
    Date of Patent: March 22, 1983
    Assignee: Monsanto Company
    Inventor: Donald E. Morris
  • Patent number: 4347387
    Abstract: A process as described for preparing hydroxycitronellal by isomerizing certain 7-hydroxygeranylamine compound or 7-hydroxynerylamine compounds using a catalyst comprising a divalent palladium compound and a phosphine compound.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: August 31, 1982
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Susumu Akutagawa, Takanao Taketomi
  • Patent number: 4324921
    Abstract: Ethers of the hydroxypivalaldehyde RCH.sub.2 OCH.sub.2 C(CH.sub.3).sub.2 CHO are prepared by a catalytic isomerization of 5,5-dimethyl-1,3-dioxans at 250.degree. to 500.degree. C. The catalyst is obtained by way of calcination from silicon dioxide, at least one element of the third main group or subgroup in the form of its oxide or hydroxide and at least one alkali metal oxide or hydroxide.
    Type: Grant
    Filed: May 29, 1980
    Date of Patent: April 13, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Jurgen Arpe
  • Patent number: 4317925
    Abstract: A process for the preparation of di-n-propylacetic acid which comprises the steps ofA. converting n-valeraldehyde-diallyl acetal into allyl-1-pentenyl ether by cleaving one mol of allyl alcohol per one mol of n-valeraldehye-diallyl acetal;B. rearranging the allyl-1-pentenyl ether thermally into 2-propyl-pent-4-en-1-al,C. partially hydrogenating the 2-propyl-pent-en-1-al catalytically to form 2-propyl valeraldehyde, andD. oxidizing the 2-propyl valeraldehyde to form dipropyl-acetic acid.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: March 2, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
  • Patent number: 4310709
    Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventor: Walter Rebafka