Isomerization Patents (Class 568/427)
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Patent number: 11732002Abstract: The present inventors found that peptide compounds/amide compounds in which the protecting groups of interest are removed and/or which are removed from resins for solid-phase synthesis can be produced without main chain damage by contacting starting peptide compounds/amide compounds with silylating agents.Type: GrantFiled: November 29, 2019Date of Patent: August 22, 2023Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kotaro Iwasaki, Shio Komiya
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Patent number: 8686193Abstract: The invention relates to a process for the preparation of m-substituted phenylalkanols of the formula (I) in which R1 is C1-C5-alkyl and R2, R3, R4 and R5, independently of one another, are hydrogen or methyl, wherein a p-substituted phenylalkanol of the formula (II) in which R1, R2, R3, R4 and R5 having the meanings given under formula (I), is isomerized in the presence of a Friedel-Crafts catalyst to give an m-substituted phenylalkanol of the formula (I). From the m-substituted phenylalkanols of the formula (I) it is possible to form, by oxidation or dehydrogenation, as products of value, the corresponding aldehydes, which are known as fragrances and aroma chemicals.Type: GrantFiled: October 19, 2010Date of Patent: April 1, 2014Assignee: BASF SEInventors: Andreas Lanver, Klaus Ebel, Karl Beck, Ralf Pelzer, Jörg Botzem, Ulrich Griesbach
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Publication number: 20120209031Abstract: The invention relates to a process for the preparation of m-substituted phenylalkanols of the formula (I) in which R1 is C1-C5-alkyl and R2, R3, R4 and R5, independently of one another, are hydrogen or methyl, wherein a p-substituted phenylalkanol of the formula (II) in which R1, R2, R3, R4 and R5 having the meanings given under formula (I), is isomerized in the presence of a Friedel-Crafts catalyst to give an m-substituted phenylalkanol of the formula (I). From the m-substituted phenylalkanols of the formula (I) it is possible to form, by oxidation or dehydrogenation, as products of value, the corresponding aldehydes, which are known as fragrances and aroma chemicals.Type: ApplicationFiled: October 19, 2010Publication date: August 16, 2012Applicant: BASF SEInventors: Andreas Lanver, Klaus Ebel, Karl Beck, Ralf Pelzer, Jörg Botzem, Ulrich Griesbach
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Patent number: 8088954Abstract: The invention relates to a compound according to Formula (IX) and salts thereof, wherein R1, R2 and R5 are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, or when the compound according to formula (IX) is a salt, R1 and/or R2 may be a cation, R3, and R4 each independently selected from hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, and wherein any two of R1, R2, R3, R4 and R5 are optionally linked together to form a ring structure. The invention further relates to the preparation of such a compound and to the use of such a compound for preparing a pharmaceutical compound, an agrochemical compound, an intermediate for a pharmaceutical compound or an intermediate for an agrochemical compound.Type: GrantFiled: July 11, 2008Date of Patent: January 3, 2012Assignee: DSM IP Assets B.V.Inventors: Gerardus Karel Maria Verzijl, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries, Lizette Schmieder, Jeroen Antonius Franciscus Boogers
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Publication number: 20100197972Abstract: The invention relates to a compound according to Formula (IX) and salts thereof, wherein R1, R2 and R5 are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, or when the compound according to formula (IX) is a salt, R1 and/or R2 may be a cation, R3, and R4 each independently selected from hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, and wherein any two of R1, R2, R3, R4 and R5 are optionally linked together to form a ring structure. The invention further relates to the preparation of such a compound and to the use of such a compound for preparing a pharmaceutical compound, an agrochemical compound, an intermediate for a pharmaceutical compound or an intermediate for an agrochemical compound.Type: ApplicationFiled: July 11, 2008Publication date: August 5, 2010Inventors: Gerardus Karel Maria Verzijl, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries, Lizette Schmieder, Jeroen Antonius Franciscus Boogers
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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
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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
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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
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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
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Patent number: 5430194Abstract: The present invention relates to a process for producing an optically active aldehyde (first aldehyde) containing a reduced amount of the corresponding enantiomeric aldehyde (second aldehyde) which process comprises: (1) providing an initial solution containing a non-eutectic mixture of the first aldehyde and the second aldehyde, which mixture has a composition in the compositional region where only the first aldehyde crystallizes when its solubility limit in the solution is exceeded, and (2) maintaining the solution at a temperature above the eutectic temperature of the mixture and under conditions such that the solubility limit of the first aldehyde is exceeded so as to form a crystalline first aldehyde containing relatively less of the second aldehyde than was present in the initial solution.Type: GrantFiled: June 24, 1994Date of Patent: July 4, 1995Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Bruce A. Barner, John R. Briggs, Jonathan J. Kurland, Charles G. Moyers, Jr.
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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
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Patent number: 5245041Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.Type: GrantFiled: December 18, 1991Date of Patent: September 14, 1993Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5225602Abstract: Phenylacetaldehydes of the structure (I) ##STR1## where the substituents X are 2,4-dichloro, difluoro, trifluoro, tetrafluoro, p-trifluoromethyl, 2-methyl-4-fluoro, haloalkoxy or haloalkylthio radicals or are adjacent Cl, F, CF.sub.3, alkyl, alkoxy, haloalkoxy and/or haloalkylthio radicals.Type: GrantFiled: October 17, 1989Date of Patent: July 6, 1993Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Rudolf Kropp, Hans Theobald, Bernd Wolf
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Patent number: 5118856Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.Type: GrantFiled: August 2, 1990Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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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
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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
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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
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Patent number: 4929765Abstract: Phenylacetaldehydes of the general formula I ##STR1## where R.sup.1 to R.sup.5 are each independently of the others hydrogen, alkyl, alkoxy, halogen, haloalkyl, haloalkoxy or haloalkylthio, by catalytic rearrangement in the presence of a zeolite, are prepared by reacting an epoxy of the formula II or a phenylglycol of the formula III ##STR2## where Y and Z can be identical to or different from each other and are each hydroxyl, alkoxy, aryloxy or acyloxy, in the gas phase over a borosilicate zeolite catalyst at from 70.degree. to 200.degree. C. under reduced pressure.Type: GrantFiled: November 22, 1988Date of Patent: May 29, 1990Assignee: BASF AktiengesellschaftInventors: Hubert Smuda, Wolfgang Hoelderich, Norbert Goetz, Hans-Gert Recker
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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
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Patent number: 4749815Abstract: A process for the manufacture of p-tert-butyl-.alpha.-methylhydrocinnamaldehyde which comprises the catalytic rearrangement of p-tert-butylbenzyl propenyl ether is provided.Type: GrantFiled: February 3, 1987Date of Patent: June 7, 1988Assignee: Givaudan CorporationInventor: Peter Gygax
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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
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Patent number: 4670607Abstract: A 2-(substituted aryl)propionaldehyde of the formula, ##STR1## (wherein Ar denotes ##STR2## is produced in high yield by reacting a methyl (substituted aryl) ketone of the formula ##STR3## with phenyldimethylsulfonium methylsulfate of the formula, ##STR4## in the presence of alkali metal hydroxide to obtain a reaction mixture containing 2-(substituted aryl)1,2-epoxypropane of the formula, ##STR5## and thioanisole, and subjecting the reaction mixture to contact with anhydrous MgCl.sub.2. The propionaldehyde compound is also produced in high yield by contacting the epoxypropane compound with anhydrous MgCl.sub.2 in the presence of a soft nucleophile such as a sulfide, a thiol and a phosphine.Type: GrantFiled: May 16, 1986Date of Patent: June 2, 1987Assignee: Hamari Chemicals, Ltd.Inventors: Sadayuki Maeda, Yasutaka Shinoo, Shinji Takenaka, Susumu Arashida, Iwao Shimizu
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Patent number: 4650908Abstract: This invention relates to the isomerization of monoaryl-ethylene oxide in the presence of water over a silica gel catalyst. Reaction temperatures are relatively low, i.e., 160.degree. C. to about 180.degree. C.Type: GrantFiled: December 23, 1985Date of Patent: March 17, 1987Assignee: The Dow Chemical CompanyInventor: Brian G. Pope
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Patent number: 4621150Abstract: A catalyst for isomerization consisting essentially of a salt or complex salt represented by the formula:[ML.sub.m ].sup.n+ [Y].sub.n.sup.- (I)where M is a metal of Group IB, IIA, IIB or VIII of the periodic table, L is a ligand, Y is a conjugated base of a Bronsted acid, m is 0, 1, 2, 3 or 4 and n is 1, 2 or 3.Type: GrantFiled: February 21, 1985Date of Patent: November 4, 1986Assignee: Sagami Chemical Research CenterInventors: Kenji Hirai, Takamasa Fuchikami, Hiroaki Hirose, Iwao Ojima
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Patent number: 4593130Abstract: This disclosure describes the catalyzed rearrangement of trans-dispiro (oxirane-2,9-(10'H)-anthracene)-10',2"-oxirane to 10-hydroxymethyl-9-anthraldehyde.Type: GrantFiled: June 24, 1985Date of Patent: June 3, 1986Assignee: American Cyanamid CompanyInventors: Donald J. Casey, William J. Trzaskos
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Patent number: 4495371Abstract: A process for isomerizing styrene or homologues to .beta.-phenylaldehydes, consisting of conducting the isomerization reaction in the presence of a catalyst constituted by synthetic zeolites containing titanium, of formulaxTiO.sub.2.(1-x)SiO.sub.2where x lies between 0.0001 and 0.04, and optionally in the presence of one or more solvents, operating at a temperature of between 30.degree. and 100.degree. C.Type: GrantFiled: July 14, 1983Date of Patent: January 22, 1985Assignee: ANIC S.p.A.Inventors: Carlo Neri, Franco Buonomo
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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
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Patent number: 4310709Abstract: 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: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka