Aldehyde Or Ketone Reactant Patents (Class 568/343)
  • Patent number: 6642418
    Abstract: The invention relates to processes for the preparation of compounds of formula (I), wherein R1 and R2 are as defined in the description.
    Type: Grant
    Filed: December 4, 2000
    Date of Patent: November 4, 2003
    Assignee: Aventis Cropscience SA
    Inventors: Susan Mary Cramp, Neil Jonathan Geach
  • Publication number: 20030199708
    Abstract: The present invention relates to a process for the preparation of compounds of formula I 1
    Type: Application
    Filed: April 8, 2003
    Publication date: October 23, 2003
    Inventors: Hermann Schneider, Christoph Luthy, Andrew Edmunds
  • Publication number: 20030187296
    Abstract: A method is provided for making an enantiomerically pure of the formula: in which R and R′ represent C1?C10 alkyl, C2?C10 alkenyl or C3?C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g.
    Type: Application
    Filed: February 5, 2003
    Publication date: October 2, 2003
    Inventors: David Clive Blakemore, Justin Stephen Bryans
  • Publication number: 20030158421
    Abstract: The invention relates to a method for the 1,3 dipolar cycloaddition of organic compounds, characterised in that the reaction is carried out in a microreactor.
    Type: Application
    Filed: April 18, 2003
    Publication date: August 21, 2003
    Inventors: Hanns Wurziger, Joeran Stoldt, Guido Pieper, Norbert Schwesinger
  • Patent number: 6590111
    Abstract: A process is provided for the preparation of cyclohexene derivatives of general formula I or II: in which the substituents R1 and R2 independently of one another are defined as follows: R2 is OH or a protective group convertible to a hydroxyl group by hydrolysis, R3 and R4 are hydrogen or C1-C4-alkyl, and R5 is hydrogen or C1-C4-acyl, by the reduction or alkyne compounds of general formula III or IV: wherein the reducing agent used is at least one salt of hyposulfurous acid or hydroxymethanesulfinic acid or a mixture of at least one salt of hyposulfurous acid and at least one salt of hydroxymethanesulfinic acid.
    Type: Grant
    Filed: August 14, 2002
    Date of Patent: July 8, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Grimmer, Thomas Müller, Volker Bomm
  • Patent number: 6559343
    Abstract: Process for the preparation of 2,2,4,4-tetrasubstituted 1,3,5-cyclohexanetriones of the formula I, by reaction of a cyclobutane-1,3-dione of the formula II with an O or N nucleophile and a silylating reagent, and subsequent acetylation and cyclization.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: May 6, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Götz, Norbert Götz, Matthias Witschel, Michael Rack
  • Patent number: 6545185
    Abstract: A method and apparatus for the production of ketones via a one-step synthesis from aldehydes. In the method of the invention, an aldehyde, a carboxylic acid, and a source of oxygen, such as water, are allowed to react in the vapor phase in a catalytic tube reactor. Asymmetrical ketones, such as methyl cyclopropyl ketone, are particularly desirable reaction products.
    Type: Grant
    Filed: October 17, 2001
    Date of Patent: April 8, 2003
    Assignee: EagleView Technologies, Inc.
    Inventors: Jack S. Warren, David R. Westphal, Steve J. Zoubek
  • Publication number: 20030060639
    Abstract: A process is provided for the preparation of cyclohexene derivatives of general formula I or II: 1
    Type: Application
    Filed: August 14, 2002
    Publication date: March 27, 2003
    Inventors: Johannes Grimmer, Thomas Muller, Volker Bomm
  • Patent number: 6515137
    Abstract: Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
    Type: Grant
    Filed: July 30, 2001
    Date of Patent: February 4, 2003
    Assignee: The Regents of the University of California
    Inventors: David W. C. MacMillan, Kateri A. Ahrendt
  • Patent number: 6500990
    Abstract: A process for efficiently producing a 2-alkyl-2-cyclopentenone comprising reacting an amine and a hydrogen halide, which are present in a ratio ranging from 1.1:1 to 5:1, with a 2-alkylidene cyclopentanone to carry out an isomerization reaction. A process for producing a jasmonate derivative comprising reacting a 2-alkyl-2-cyclopentenone with a malonic acid diester.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: December 31, 2002
    Assignee: Kao Corporation
    Inventors: Takahiro Asada, Yoshiharu Ataka, Junji Koshino
  • Publication number: 20020165414
    Abstract: Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content below 5 wt.-% and subsequent isomerization of the mixture of &bgr;-isophorone epoxide and hydroxyisophorone.
    Type: Application
    Filed: February 28, 2002
    Publication date: November 7, 2002
    Inventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
  • Publication number: 20020161263
    Abstract: A process for the preparation of ketones corresponding to the general Formula I 1
    Type: Application
    Filed: April 26, 2002
    Publication date: October 31, 2002
    Applicant: DEGUSSA AG
    Inventors: Nongyuan Shi, Steffen Krill, Klaus Huthmacher, Bernd Drapal
  • Patent number: 6468949
    Abstract: The present invention is directed to cyclopropyl-2,6,6-trimethylcyclohex-3-enyl ketone and is use in creating perfumes and scents in such items as perfumes, colognes, toilet water and personal care products.
    Type: Grant
    Filed: December 10, 2001
    Date of Patent: October 22, 2002
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William L. Schreiber
  • Patent number: 6469215
    Abstract: A process for the production of an intermediate mixture of &bgr;-isophorone epoxide and its isomer 4-hydroxyisophorone (HIP), comprising reacting &bgr;-isophorone with an organic percarboxylic acid, in the form of its non-aqueous solution, in an inert solvent.
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: October 22, 2002
    Assignee: Degussa AG
    Inventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
  • Patent number: 6465664
    Abstract: One aspect of the present invention relates to methods for the transition-metal-catalyzed asymmetric 1,4-addition of a nucleophile, e.g., hydride, to cyclic and acyclic enoates and enones. In certain embodiments of the methods of the present invention, the transition metal catalyst consists essentially of copper and an asymmetric bidentate bisphosphine ligand.
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: October 15, 2002
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L Buchwald, Daniel H. Appella, Yasunori Moritani, Ryo Shintani, Valdas Jurkauskas
  • Patent number: 6437190
    Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: August 20, 2002
    Assignee: Siemens Axiva GmbH & Co. KG
    Inventors: Inga Leipprand, Thorsten Lahrs
  • Patent number: 6433229
    Abstract: Preparation of cyclic, &agr;,&bgr;-unsaturated ketones of formula II by dehydrogenation of cyclic ketones which conform to formula I in which n denotes an integer from 1 to 10, and which may be substituted, at elevated temperature in the presence of catalysts in the vapor phase, wherein the reaction is carried out in the absence of oxygen or in the presence of less than 0.5 mol of oxygen per mol of compound I at temperatures ranging from 250° to 600° C. and using catalysts having a surface area (BET) of more than 0.5 m2/g.
    Type: Grant
    Filed: September 5, 2001
    Date of Patent: August 13, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos
  • Patent number: 6433230
    Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising: reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: August 13, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
  • Patent number: 6420609
    Abstract: Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content below 5 wt.-% and subsequent isomerization of the mixture of &bgr;-isophorone epoxide and hydroxyisophorone.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: July 16, 2002
    Assignee: Degussa AG
    Inventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
  • Patent number: 6392099
    Abstract: A method for continuously producing a ketone in a tube reactor at elevated weight hourly space velocities and in the presence of a catalyst from feed material comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid and a method for using the ketone production method to produce herbicidal or other agricultural compounds.
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: May 21, 2002
    Assignee: EagleView Technologies, Inc.
    Inventor: Jack S. Warren
  • Publication number: 20020055453
    Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.
    Type: Application
    Filed: August 2, 2001
    Publication date: May 9, 2002
    Inventors: Marcus Eh, Ingo Wohrle
  • Publication number: 20020045768
    Abstract: A process is provided for the preparation of cyclohexene derivatives of general formula I or II: 1
    Type: Application
    Filed: September 18, 2001
    Publication date: April 18, 2002
    Inventors: Johannes Grimmer, Thomas Muller, Hansgeorg Ernst
  • Patent number: 6350917
    Abstract: Crystals of trans-4,5-dihydroxy-2-cyclopenten-1-one of an &agr;-type.
    Type: Grant
    Filed: December 29, 1999
    Date of Patent: February 26, 2002
    Assignee: Takara Shuzo Co., Ltd.
    Inventors: Makoto Moriguchi, Katsushige Ikai, Masao Funakoshi, Hiroshi Kobori, Kazuyori Ochiai, Ikunoshin Kato
  • Publication number: 20010025123
    Abstract: Disclosed is a process for oxidizing organic compounds using hydrogen peroxide to oxidize an oxidizable organic substrate in the presence of a silylated peroxide-activating metal/silica-containing catalyst and to a method of preparing such a catalyst.
    Type: Application
    Filed: April 18, 2001
    Publication date: September 27, 2001
    Inventors: Michael Brian D'Amore, Stephan Schwarz
  • Patent number: 6288282
    Abstract: Process for the continuous preparation of &agr;- and/or &bgr;-ionone or homologous compounds using concentrated sulfuric acid at temperatures from 20 to 90° C.
    Type: Grant
    Filed: May 9, 2000
    Date of Patent: September 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Rheude, Ulrich Hörcher, Dietmar Weller, Manfred Stroezel
  • Patent number: 6287829
    Abstract: A process for the selective enzymatic hydroxylation of aldehydes and ketones using chiral anchor-protective groups.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: September 11, 2001
    Assignee: DSM Fine Chemical Austria Nfg GmbH & Co KG
    Inventors: Anna Stütz de Raadt, Irene Kopper, Herfried Griengl, Markus Klingler, Gerhart Braunegg
  • Patent number: 6284928
    Abstract: The invention relates to an improved process for preparing [(3aR,4S,7aS)4-bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminum hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R—Cu, wherein R is and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C1-4 alkyl group, benzyl, or benzyl substituted by at at least one C1-4 alkyl group to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)4-bromooctahydro-7a-methyl-1H-indene-1,5-dione.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: September 4, 2001
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Andrzej Robert Daniewski
  • Patent number: 6245946
    Abstract: Catalytic process for converting cyclododecane-1,2-dione to cyclododecanone.
    Type: Grant
    Filed: August 8, 2000
    Date of Patent: June 12, 2001
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Ronald Lee Amey
  • Patent number: 6242413
    Abstract: The invention relates to bicyclic aldehydes and ketones of formula (I): wherein n is 1 or 2; R1 and R4 are independently H or CH3; and R2 and R3 are independently H, CH3 or CH2CH3 The invention also provides odorant compositions containing at least one compound of formula (I). A process for the manufacture of R1-methyl substituted compounds of formula (I) having a bridgehead-positioned double bond, as well as intermediates thereof is also provided.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: June 5, 2001
    Assignee: Givaudan Roure (International) S.A.
    Inventors: Georg Frater, Philip Kraft
  • Patent number: 6222076
    Abstract: The invention relates to a novel process for the preparation of hydroxyalkyl- and acyloxyalkyl-substituted cycloketones by free-radical addition of hydroxyalkenes and acyloxyalkenes respectively to cyclic ketones.
    Type: Grant
    Filed: December 18, 1998
    Date of Patent: April 24, 2001
    Assignee: Haarmann & Reimer GmbH
    Inventors: Alfred Krempel, Oskar Koch, Harry Erfurt
  • Patent number: 6207864
    Abstract: The invention relates to a process for the halogenation of cyclopropylmethyl ketone with at least one dihalo-triorganophosphorane of the general formula I R3PHal2   (I), in which the radicals R can be the same or different and denote a saturated or unsaturated aliphatic C1-C20 hydrocarbon radical, a phenyl or (C1-C4 alkyl)phenyl radical, which may be optionally substituted by one or two fluorine, chlorine and/or nitro groups, P stands for phosphorus and Hal denotes chlorine, bromine, or iodine, at a temperature of from 800° to 130° C.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Henningsen, Armin Stamm, Martin Fischer, Wolfgang Siegel
  • Patent number: 6200254
    Abstract: Novel macrocyclic diene ketone compounds useful as fragrance materials are described having the following general formula (I): where R1, R2, R3 and R4 are each either a hydrogen atom or a C1 to C4 alkyl, a is the integer 1 or 2 and b is an integer in a range from 1 to 6. Novel pathways are described for synthesizing these macrocyclic diene ketones, as well as saturated and mono-unsaturated macrocyclic ketones having the following general formula (IV): where R1, R2, R3 and R4 are each independently a hydrogen atom or a C1 to C4 alkyl, a is the integer 1 or 2 and b is an integer in a range from 1 to 6.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: March 13, 2001
    Assignees: Takasago International Corporation, Takasago Institute for Interdisciplinary Science, Inc.
    Inventors: Andrew T. Lupo, Jr., Tetsuo Nakatsu, John Caldwell, Michael E. Lankin, Carter B. Green, Takashi Aida
  • Patent number: 6201155
    Abstract: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: March 13, 2001
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, August Rüttimann
  • Patent number: 6187961
    Abstract: A process for the manufacture of trans-(R,R)-actinol by diasteroselective transfer hydrogenation of levodione comprises hydrogenating (R)-levodione in the presence of a hydrogen donor, which simultaneously can be used as the solvent, and an amino-amide-ruthenium complex, especially of the formula RuH(L{—H})(Y), wherein Y signifies a neutral ligand and L signifies an optionally optically active monosulphonylated diamine ligand, as defined in more detail in the description. Moreover, the invention is concerned with some of the amino-amide-ruthenium complexes and with the corresponding precursors to these complexes, which have halogen in place of H. The product of the process in accordance with the invention, trans-(R,R)-actinol, is known as an important building block for the synthesis of carotenoids, e.g. zeaxanthin. By the process trans-(R,R)-actinol is made available in particularly high enantiomeric and diasteromeric purity.
    Type: Grant
    Filed: October 20, 1998
    Date of Patent: February 13, 2001
    Assignee: Roche Vitamins Inc.
    Inventors: Yvo Crameri, Kurt Püntener, Michelangelo Scalone
  • Patent number: 6169211
    Abstract: Disclosed is a process for producing 5-cyclohexadecen-1-one continuously from 1,2-divinylcyclododecanol in a short time in an efficient manner without side reactions. In the process, 1,2-divinylcyclododecanol as a starting material is supplied from a raw material container 1 by a dosage pump 2 to a flash unit 3 which is set under a vacuum of 5 mm Hg or less by a vacuum pump 8 and is heated. 1,2-Divinylcyclododecanol which is flashed in the flash unit is supplied to a reactor 4 which is heated to 400 to 650° C. and is set under a vacuum of 5 mm Hg or less whereby 1,2-divinylcyclododecanol is converted into 5-cyclohexadecen-1-one. The reaction product is discharged from the top of the reactor and is cooled to recover the objective 5-cyclohexadecen-1-one in the recovery container 6. The reduction in the pressure of the apparatus is preferably performed by a vacuum pump 8 via a hydrochloric acid trap 7 comprising, for example, sodium methylate/methanol cooled to −78 to −100° C.
    Type: Grant
    Filed: May 6, 1999
    Date of Patent: January 2, 2001
    Assignee: Takasago International Corporation
    Inventors: Misao Yagi, Keisuke Itakura, Kenichi Yamamoto, Akira Amano
  • Patent number: 6160182
    Abstract: Acid catalyzed cyclization of Diels-Alder adducts of myrcene is performed in the presence of hydroxyl-containing compounds, giving the resulting mixtures of isomeric acyloctahydronaphthalenes enhanced quantities of isomers that are particularly useful in perfumery because of their woody-amber odors with enhanced amber note.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: December 12, 2000
    Assignee: Millennium Specialty Chemicals
    Inventors: Mark B. Erman, Carlos G. Cardenas, Henri M. Hoffmann
  • Patent number: 6150561
    Abstract: A widely applicable process for the manufacture of carotenoids by a Wittig reaction comprises carrying out the Wittig reaction in a polar reaction medium in a manner such that neither the reactants nor the thus-manufactured carotenoid are significantly dissolved in the reaction medium. An especially suitable reaction medium is a polar, toxicologically harmless solvent which remains monophasic on the addition of water in an amount up to about 30 vol. % and which permits the triarylphosphine oxide which is formed to dissolve well. Lower alcohols and acetone, as sole solvents or as mixtures with one another and/or with water, are especially suitable as the polar reaction medium. This process permits the use of much more concentrated reaction mixtures, simplifies the regeneration of the solvent and generally the reaction procedure, and avoids toxicologically objectionable solvents such as halogenated hydrocarbons.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: November 21, 2000
    Assignee: Roche Vitamins Inc.
    Inventors: Paul Kreienbuhl, Peter Rudin, Werner Rudolph
  • Patent number: 6140542
    Abstract: Process for the continuous preparation of .alpha.- and/or .beta.-ionone or homologous compounds using concentrated sulfuric acid at temperatures from 20 to 90.degree. C.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: October 31, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Rheude, Ulrich Horcher, Dietmar Weller, Manfred Stroezel
  • Patent number: 6069261
    Abstract: A process carried out in a reaction column for the chemical reaction of substances the reaction of which is affected by an unfavorable equilibrium position of the main reaction or a preceding equilibrium, wherein during the reaction one or more substances to be separated are continuously removed from the reaction mixture by one or more auxiliaries.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: May 30, 2000
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Ulrich Hoffmann, Ulrich Kunz
  • Patent number: 6025527
    Abstract: Described are trimethylcyclohexenylcyclopropyl ketones having the structure: ##STR1## wherein one of the dashed lines is a carbon--carbon double bond and the other of the dashed lines is a carbon--carbon single bond, uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles, and mixtures of same with 3-methyl-1-phenylpentanol-5 and/or butanoylcyclohexane derivatives and/or acetic or propionic acid esters of o-methylphenyl isopropanol.
    Type: Grant
    Filed: June 18, 1999
    Date of Patent: February 15, 2000
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna
  • Patent number: 6011182
    Abstract: The present invention relates to a process for preparing 2-cyclo-alkenones of the formula I ##STR1## which comprises subjecting a 2-alkoxycycloalkanone and/or a 2-hydroxyalkanone ketal, in which n is an integer from 0 to 20, m is 0, 1, 2 or 3 and R is alkyl, alkylaryl, aryl, arylalkyl, alkenyl or alkynyl, to an elimination reaction in the gas phase on an acidic heterogeneous catalyst.
    Type: Grant
    Filed: February 1, 1999
    Date of Patent: January 4, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Eiermann, Klaus Ebel, Jorg Botzem
  • Patent number: 6004905
    Abstract: The invention disclosed relates to a new class of abscisic acid (ABA) analogs of formula I ##STR1## wherein one of R.sub.1 is alkenyl, alkynyl, aryl, cycloalkenyl, other farther substituted carbon chain including deuterium containing residues, and carbon containing substituents with heteroatoms and halogens and the other is methyl, and wherein the five member carbon side chain includes a methyl group at C3, with C5 attached to the ring as shown, including a trans double bond at the C4-C5 position, or a triple bond at this position, and either a cis or a trans double bond at the C2-C3 position, and R.sub.2 is CH.sub.2 OH, CHO, COOH, COO alkyl, or derivatives thereof, and wherein the cyclohexanone ring double bond may also be reduced and to a novel process for synthesizing such ABA analogs.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: December 21, 1999
    Assignee: National Research Council of Canada
    Inventors: Suzanne R. Abrams, John J. Balsevich, Adrian J. Cutler, Bo Lei, Patricia A. Rose
  • Patent number: 6002046
    Abstract: Cyclopropyl alkyl ketones are separated from 3-acyltetrahydrofuran-2-ones by adding an alcohol, water or a water/alcohol mixture to a reaction product containing C.sub.1-4 -alkyl cyclopropyl ketone and 4,5-dihydro-2-alkylfuran by-product and an acid catalyst and reacting the by-product with the added alcohol, water of water/alcohol mixture before, during or after distilling said reaction product; and effectively separating C.sub.1 -.sub.4 -alkyl cyclopropyl ketone from reaction by-products.In the preparation of cyclopropyl alkyl ketones from 3-acyltetrahydrofuran-2-ones very reactive 4,5-dihydro-2-alkylfurans are also produced. By reacting such compounds with nucleophilic compounds, such as alcohols or water, before, during or after distillation of the reaction products, it is possible reliably to separate off the 4,5-dihydro-2-alkylfurans as high-boiling addition compounds.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: December 14, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Wolfgang Kleemiss, Udo Jegelka, Michael Korell
  • Patent number: 5824817
    Abstract: The invention relates to the use of the known compound 2,6-dichloro-3-fluoro-benzonitrile as active compound in selectively-herbicidal compositions, and to new preparation processes and new intermediates for the preparation of this compound.
    Type: Grant
    Filed: July 28, 1997
    Date of Patent: October 20, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Werner Bussmann, Josef Kasbauer, Markus Dollinger, Hans-Joachim Santel
  • Patent number: 5763627
    Abstract: The invention relates to a novel process for simultaneously preparing cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones in the presence of a metal salt according to the scheme ##STR1## during the reaction, high-boiling poly (ethylene glycol) dialkyl ethers are then used. By introducing the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and adding further 3-acyltetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can, moreover, be recovered in a simple manner by washing with water.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: June 9, 1998
    Assignee: Huels Aktiengesellschaft
    Inventor: Manfred Kaufhold
  • Patent number: 5707961
    Abstract: The invention is concerned with novel odorants, including the compounds of the formula ##STR1## wherein R.sup.1 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.2 .dbd.R.sup.3 .dbd.H orR.sup.1 .dbd.R.sup.2 .dbd.R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.3, orR.sup.1 +R.sup.2 .dbd.--CH.sub.2 CH.sub.2 -- and R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.3, orR.sup.1 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.2 +R.sup.3 .dbd.--CH.sub.2 -- orR.sup.1 .dbd.CH.sub.3 and R.sup.2 .dbd.R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.2 CH.sub.3 orR.sup.1 .dbd.R.sup.2 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.3 .dbd.H and R.sup.5 .dbd.H (preferred) or CH.sub.3.
    Type: Grant
    Filed: April 25, 1996
    Date of Patent: January 13, 1998
    Assignee: Givaudan-Roure (International) SA
    Inventors: Jerzy A. Bajgrowicz, Alain Bringhen, Georg Frater, Urs Muller
  • Patent number: 5654488
    Abstract: Improved process for the preparation of astaxanthin by Wittig reaction of 2 mol of 3-methyl-5-(2,6,6-trimethyl-3-oxo-4-hydroxy-1-cyclohexenyl)-2,4-pentadieny ltriarylphosphonium salts with one mol of 2,7-dimethyl-2,4,6-octatrienedial avoiding the use of halohydrocarbons as solvents.
    Type: Grant
    Filed: March 15, 1996
    Date of Patent: August 5, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Krause, Klaus Henrich, Joachim Paust, Hansgeorg Ernst
  • Patent number: 5629455
    Abstract: The invention relates to a novel process for the simultaneous preparation of cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones using a metal salt according to the diagram ##STR1## In the reaction, N-alkyllactams and/or N-acylmorpholines which are high-boiling and only slightly miscible with water are used. By charging the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess with respect to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and metering in further 3-acyl-tetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can moreover be recovered in a simple manner by washing with water.
    Type: Grant
    Filed: January 23, 1996
    Date of Patent: May 13, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Marcel Feld
  • Patent number: 5625099
    Abstract: Abstract of the Disclosure: Compounds of the formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is an ether, silyl ether or acetal protective group which can be converted into a hydroxyl group by hydrolysis, in particular one of the radicals ##STR2## and a process for preparing these compounds by reacting an alkenyne of the formula II ##STR3## in an inert solvent in the presence of lithium amide with a cyclohexenone of the formula III ##STR4## and the use of the compounds of the formula I for preparing astaxanthin, are described.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: April 29, 1997
    Inventors: Hansgeorg Ernst, Walter Dobler, Joachim Paust, Udo Rheude
  • Patent number: 5563286
    Abstract: A process is disclosed for the removal of the 4-protected hydroxy group from compounds of the following formula: ##STR1## where A is --COOAlkyl and B is hydroxy, or A and B together represent either oxo or .dbd.CHCOOAlkyl, where X.sup.1 and X.sup.2 are the same or different and represent hydrogen or a hydroxy-protecting group, and where X.sup.3 is ##STR2## with a hydrogen radical source, such as tributyltin hydride or tris(trimethylsilyl)silane, and a radical initiator, such as AIBN or irradiation.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: October 8, 1996
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson