Isomerization Patents (Class 568/427)
  • Patent number: 11732002
    Abstract: 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: Grant
    Filed: November 29, 2019
    Date of Patent: August 22, 2023
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Kotaro Iwasaki, Shio Komiya
  • Patent number: 8686193
    Abstract: 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: Grant
    Filed: October 19, 2010
    Date of Patent: April 1, 2014
    Assignee: BASF SE
    Inventors: Andreas Lanver, Klaus Ebel, Karl Beck, Ralf Pelzer, Jörg Botzem, Ulrich Griesbach
  • Publication number: 20120209031
    Abstract: 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: Application
    Filed: October 19, 2010
    Publication date: August 16, 2012
    Applicant: BASF SE
    Inventors: Andreas Lanver, Klaus Ebel, Karl Beck, Ralf Pelzer, Jörg Botzem, Ulrich Griesbach
  • Patent number: 8088954
    Abstract: 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: Grant
    Filed: July 11, 2008
    Date of Patent: January 3, 2012
    Assignee: 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
  • Publication number: 20100197972
    Abstract: 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: Application
    Filed: July 11, 2008
    Publication date: August 5, 2010
    Inventors: Gerardus Karel Maria Verzijl, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries, Lizette Schmieder, Jeroen Antonius Franciscus Boogers
  • 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: 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: 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: 5430194
    Abstract: 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: Grant
    Filed: June 24, 1994
    Date of Patent: July 4, 1995
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Bruce A. Barner, John R. Briggs, Jonathan J. Kurland, Charles G. Moyers, Jr.
  • 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: 5245041
    Abstract: 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: Grant
    Filed: December 18, 1991
    Date of Patent: September 14, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5225602
    Abstract: 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: Grant
    Filed: October 17, 1989
    Date of Patent: July 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Rudolf Kropp, Hans Theobald, Bernd Wolf
  • Patent number: 5118856
    Abstract: 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: Grant
    Filed: August 2, 1990
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • 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: 4929765
    Abstract: 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: Grant
    Filed: November 22, 1988
    Date of Patent: May 29, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Smuda, Wolfgang Hoelderich, Norbert Goetz, Hans-Gert Recker
  • 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: 4749815
    Abstract: 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: Grant
    Filed: February 3, 1987
    Date of Patent: June 7, 1988
    Assignee: Givaudan Corporation
    Inventor: Peter Gygax
  • 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: 4670607
    Abstract: 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: Grant
    Filed: May 16, 1986
    Date of Patent: June 2, 1987
    Assignee: Hamari Chemicals, Ltd.
    Inventors: Sadayuki Maeda, Yasutaka Shinoo, Shinji Takenaka, Susumu Arashida, Iwao Shimizu
  • Patent number: 4650908
    Abstract: 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: Grant
    Filed: December 23, 1985
    Date of Patent: March 17, 1987
    Assignee: The Dow Chemical Company
    Inventor: Brian G. Pope
  • Patent number: 4621150
    Abstract: 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: Grant
    Filed: February 21, 1985
    Date of Patent: November 4, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Kenji Hirai, Takamasa Fuchikami, Hiroaki Hirose, Iwao Ojima
  • Patent number: 4593130
    Abstract: This disclosure describes the catalyzed rearrangement of trans-dispiro (oxirane-2,9-(10'H)-anthracene)-10',2"-oxirane to 10-hydroxymethyl-9-anthraldehyde.
    Type: Grant
    Filed: June 24, 1985
    Date of Patent: June 3, 1986
    Assignee: American Cyanamid Company
    Inventors: Donald J. Casey, William J. Trzaskos
  • Patent number: 4495371
    Abstract: 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: Grant
    Filed: July 14, 1983
    Date of Patent: January 22, 1985
    Assignee: ANIC S.p.A.
    Inventors: Carlo Neri, Franco Buonomo
  • 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: 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