Isomerization Patents (Class 568/450)
-
Patent number: 11111197Abstract: Process for the preparation of alpha, beta unsaturated aldehydes by oxidation of alcohols in the presence of a liquid phase.Type: GrantFiled: December 5, 2018Date of Patent: September 7, 2021Assignee: BASF SEInventors: Michaela Fenyn, Joseph John Zakzeski, Nicolas Vautravers, Joaquim Henrique Teles
-
Patent number: 11046632Abstract: Process for the preparation of 3-methyl-2-buten-1-al, wherein 2-methyl-3-buten-2-ol is reacted to 3-methyl-2-buten-1-al in the presence of a catalyst, wherein the catalyst comprises a catalytically active metal and wherein the reaction is conducted at a pH of ?7.Type: GrantFiled: December 5, 2018Date of Patent: June 29, 2021Assignee: BASF SEInventors: Nicolas Vautravers, Michaela Fenyn, Joseph John Zakzeski, Joaquim Henrique Teles
-
Patent number: 9284246Abstract: A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed.Type: GrantFiled: September 6, 2013Date of Patent: March 15, 2016Assignee: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hideo Ujihara, Mitsuhiko Fujiwhara
-
Patent number: 9193655Abstract: 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: GrantFiled: August 30, 2013Date of Patent: November 24, 2015Assignee: KURARAY CO., LTD.Inventor: Tomoaki Tsuji
-
Patent number: 8884070Abstract: 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: GrantFiled: June 16, 2011Date of Patent: November 11, 2014Assignee: EVONIK DEGUSSA GmbHInventors: Robert Franke, Dirk Fridag, Bart Hamers, Horst-Werner Zanthoff, Matthias Blug, Julia Strautmann, Stefan Nordhoff
-
Patent number: 8871745Abstract: 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: GrantFiled: August 12, 2013Date of Patent: October 28, 2014Assignee: Millennium Pharmaceuticals, Inc.Inventors: Edward J. Olhava, Mihaela Diana Danca
-
Publication number: 20140051759Abstract: 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: ApplicationFiled: September 17, 2012Publication date: February 20, 2014Inventors: John L. Gainer, Raymond C. Grabiak
-
Patent number: 8404902Abstract: 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 isobuteType: GrantFiled: April 28, 2009Date of Patent: March 26, 2013Assignee: Evonik Oxeno GmbHInventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
-
Publication number: 20110071321Abstract: 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 isobuteType: ApplicationFiled: April 28, 2009Publication date: March 24, 2011Applicant: EVONIK OXENO GMBHInventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
-
Publication number: 20100048959Abstract: 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: ApplicationFiled: November 29, 2007Publication date: February 25, 2010Applicant: BASF SEInventors: 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: 7348459Abstract: 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: GrantFiled: October 24, 2006Date of Patent: March 25, 2008Assignee: The Nutrasweet CompanyInventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
-
Patent number: 6909019Abstract: 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: GrantFiled: May 25, 2004Date of Patent: June 21, 2005Assignee: Eastman Chemical CompanyInventor: Sheryl Davis Debenham
-
Patent number: 6573409Abstract: 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: GrantFiled: May 19, 2000Date of Patent: June 3, 2003Assignee: The Nutrasweet CompanyInventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
-
Patent number: 6403839Abstract: 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: GrantFiled: June 12, 2001Date of Patent: June 11, 2002Assignee: BP Chemicals LimitedInventor: Benjamin Patrick Gracey
-
Patent number: 6329555Abstract: 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: GrantFiled: November 2, 1999Date of Patent: December 11, 2001Assignee: BASF AktiengesellschaftInventors: Maik Aron, Ralf Böhling, Peter Zehner
-
Patent number: 6278031Abstract: 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: GrantFiled: January 16, 2001Date of Patent: August 21, 2001Assignee: BASF AktiengesellschaftInventors: Franz Josef Bröcker, Werner Aquila, Klemens Flick, Gerd Kaibel, Ernst Langguth
-
Patent number: 6239324Abstract: 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: GrantFiled: August 26, 1999Date of Patent: May 29, 2001Assignee: Takasago International CorporationInventors: Mitsuhiko Fujiwhara, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara, Hisao Iwai, Takashi Miura
-
Patent number: 6198006Abstract: 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: GrantFiled: March 16, 1999Date of Patent: March 6, 2001Assignee: Roche Vitamins Inc.Inventor: Werner Bonrath
-
Patent number: 6191313Abstract: 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: GrantFiled: March 29, 1999Date of Patent: February 20, 2001Assignee: Roche Vitamins Inc.Inventor: Werner Bonrath
-
Patent number: 6166265Abstract: 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: GrantFiled: September 15, 1999Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Jurgen Kanand, Rocco Paciello, Michael Roper
-
Patent number: 6118027Abstract: 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: GrantFiled: April 20, 1999Date of Patent: September 12, 2000Assignee: Givaudan Roure (International) SAInventors: Alan John Chalk, Joseph Anthony Virgilio
-
Patent number: 6013843Abstract: 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: GrantFiled: May 28, 1998Date of Patent: January 11, 2000Assignee: BASF AktiengeselllschaftInventors: Werner Aquila, Hartwig Fuchs, Otto Worz, Wilhelm Ruppel, Klaus Halbritter
-
Patent number: 5994590Abstract: 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: GrantFiled: September 30, 1998Date of Patent: November 30, 1999Assignee: Kuraray Co., Ltd.Inventors: Tomoyasu Tsuda, Yasuo Tokitoh, Kazunori Watanabe, Takashi Hori
-
Patent number: 5905175Abstract: 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: GrantFiled: May 20, 1998Date of Patent: May 18, 1999Assignee: The NutraSweet CompanyInventors: Zhi Guo, Indra Prakash
-
Patent number: 5892125Abstract: 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: GrantFiled: July 23, 1997Date of Patent: April 6, 1999Assignee: BASF AktiengesellschaftInventors: Jurgen Kanand, Michael Roper, Rocco Paciello, Alfred Thome
-
Patent number: 5856584Abstract: 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: GrantFiled: August 6, 1997Date of Patent: January 5, 1999Assignee: The Nutrasweet CompanyInventors: Indra Prakash, David J. Ager, Alan R. Katritzky
-
Patent number: 5770775Abstract: 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: GrantFiled: February 10, 1997Date of Patent: June 23, 1998Assignee: The NutraSweet CompanyInventors: Alan R. Katritzky, Indra Prakash
-
Patent number: 5705707Abstract: 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: GrantFiled: July 12, 1996Date of Patent: January 6, 1998Assignee: BASF AktiengesellschaftInventors: Jurgen Kanand, Michael Roper, Rolf Pinkos, Rocco Paciello, Alfred Thome
-
Patent number: 5502257Abstract: 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: GrantFiled: February 21, 1995Date of Patent: March 26, 1996Assignee: Eastman Chemical CompanyInventors: Shaowo Liang, Timothy W. Price, Timothy R. Nolen, Daniel B. Compton, David C. Attride
-
Patent number: 5481044Abstract: .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: GrantFiled: December 15, 1994Date of Patent: January 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Helmut Springer
-
Patent number: 5312995Abstract: 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: GrantFiled: April 23, 1993Date of Patent: May 17, 1994Assignee: Arco Chemical Technology, L.P.Inventor: Mahmoud K. Faraj
-
Patent number: 5177258Abstract: 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: GrantFiled: May 21, 1992Date of Patent: January 5, 1993Assignee: Bromine Compounds, Ltd.Inventors: Abram Becker, Ariel A. Ewenson, Bertha Croitoru
-
Patent number: 5077438Abstract: 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: GrantFiled: February 14, 1991Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Werner Steck, Matthias Schwarzmann, Kurt Weinacht, Franz Merger
-
Patent number: 5012005Abstract: 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: GrantFiled: July 27, 1989Date of Patent: April 30, 1991Inventors: Wolfgang Hoelderich, Franz Merger
-
Patent number: 4996365Abstract: 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: GrantFiled: August 31, 1989Date of Patent: February 26, 1991Assignee: BASF AktiengesellschaftInventors: Gerald Lauterbach, Frank F. Pape, Walter Gramlich
-
Patent number: 4980511Abstract: 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: GrantFiled: September 25, 1987Date of Patent: December 25, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Helmut Lermer
-
Patent number: 4950797Abstract: 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: GrantFiled: June 1, 1988Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
-
Patent number: 4939280Abstract: 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: GrantFiled: April 29, 1988Date of Patent: July 3, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Helmut Lermer
-
Patent number: 4925987Abstract: 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: GrantFiled: April 13, 1989Date of Patent: May 15, 1990Assignee: Eastman Kodak CompanyInventors: John R. Monnier, Howard M. Low
-
Patent number: 4925986Abstract: 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: GrantFiled: April 13, 1989Date of Patent: May 15, 1990Assignee: Eastman Kodak CompanyInventors: John R. Monnier, Peter J. Muehlbauer, Howard M. Low
-
Patent number: 4749814Abstract: 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: GrantFiled: April 2, 1987Date of Patent: June 7, 1988Assignee: Rhone-Poulenc SanteInventor: Pierre Chabardes
-
Patent number: 4709097Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.Type: GrantFiled: April 14, 1986Date of Patent: November 24, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
-
Patent number: 4677230Abstract: 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: GrantFiled: June 11, 1986Date of Patent: June 30, 1987Assignee: BASF AktiengesellschaftInventors: Leopold Hupfer, Franz Merger, Franz J. Broecker, Rolf Fischer
-
Patent number: 4605779Abstract: 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: GrantFiled: July 24, 1985Date of Patent: August 12, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Teruo Matsuda, Shinkichi Shimizu, Masaaki Iwasa
-
Patent number: 4599458Abstract: 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: GrantFiled: June 7, 1985Date of Patent: July 8, 1986Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Hans-Martin Weitz
-
Patent number: 4510331Abstract: 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: GrantFiled: June 22, 1982Date of Patent: April 9, 1985Assignee: Kuraray Company, Ltd.Inventors: Noriaki Yoshimura, Masuhiko Tamura
-
Patent number: 4463196Abstract: 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: GrantFiled: May 8, 1980Date of Patent: July 31, 1984Assignee: Rhone-Poulenc IndustriesInventors: Pierre Chabardes, Emile Kuntz
-
Patent number: 4377708Abstract: 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: GrantFiled: October 14, 1977Date of Patent: March 22, 1983Assignee: Monsanto CompanyInventor: Donald E. Morris
-
Patent number: 4347387Abstract: 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: GrantFiled: December 4, 1980Date of Patent: August 31, 1982Assignee: Takasago Perfumery Co., Ltd.Inventors: Susumu Akutagawa, Takanao Taketomi
-
Patent number: 4324921Abstract: 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: GrantFiled: May 29, 1980Date of Patent: April 13, 1982Assignee: Hoechst AktiengesellschaftInventor: Hans-Jurgen Arpe