Reactant Contains -coo- Group Patents (Class 568/346)
  • Patent number: 5852200
    Abstract: Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: December 22, 1998
    Assignee: Rieke Metals, Inc.
    Inventor: Reuben D. Rieke
  • Patent number: 5847226
    Abstract: A method for preparing nootkatone, nootkatol or mixtures thereof by oxidizing valencene, wherein the valencene is exposed to an oxygenated atmosphere in a suitable reaction medium and in the presence of an unsaturated fatty acid hydroperoxide, and the nootkatone and/or nootkatol is (are) optionally separated from the reaction medium. The method enables nootkatone yields of around 60 g per kg of reaction medium to be achieved.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: December 8, 1998
    Assignee: Firmenich SA
    Inventors: Bernard Muller, Christopher Dean, Christian Schmidt, Jean-Charles Kuhn
  • Patent number: 5808165
    Abstract: The present invention is directed to compositions containing novel beta-diketones of formula (I) and formula (II),R.sub.1 COCH.sub.2 COR.sub.2 (I)R.sub.2 COCH.sub.2 COR.sub.2 (II)which may be used to stabilize various polymers, such as polyvinyl chlorides (PVCs). The present invention is also directed to a method for preparing .beta.-diketones by a Claisen condensation reaction, which is represented as follows:R.sub.4 COCHR.sub.5 H+R.sub.6 C(O)OR.sub.7 +RO.sup.- .fwdarw.?R.sub.4 COCR.sub.5 COR.sub.6 !-+R.sub.7 OH+ROH.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: September 15, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Serge Chassaing, Michel Gay, Gilles Mur
  • 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: 5672763
    Abstract: 2-Substituted cyclopentanones are prepared by reacting adipic ester with an alkoxide in the presence of an inert solvent, thus obtaining a salt of the cyclopentanone-2-carboxylic ester, alkylating this without isolation, thus obtaining a 2-alkyl-cyclopentanone-2-carboxylic ester and, without isolation, hydrolysing and decarboxylating this by treatment with an acid and heating.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Nikolaus Muller, Thomas Essert
  • Patent number: 5618982
    Abstract: Ketones having at least one hydrogen atom or ester group in the .alpha.-position with respect to a ketonic carbonyl group thereof, for example cyclopentanone, 2-methylcyclopentanone and other substituted cyclopentanones, are effectively C- or .alpha.-alkylated, especially on an industrial scale, by reacting same with an alkylating agent in the presence of a catalytically effective amount of a condensed or uncondensed orthophosphate anion.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: April 8, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Laurent Gilbert, Michel Spagnol
  • Patent number: 5545762
    Abstract: 1-cyclopropylalkane-1,3-diones are prepared by reacting a cyclopropyl alkyl ketone with a carboxylic ester in the presence of an alkali metal alcoholate, at temperatures of not more than 50.degree. C. in the presence of a solvent which is free of alcohol or contains only small quantities of alcohol.
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: August 13, 1996
    Assignee: Huels Aktiengesellschaft
    Inventor: Jurgen Muhr
  • Patent number: 5484949
    Abstract: The present invention relates to a method for the synthesis of .alpha., .beta.-unsaturated ketones which comprises, in the method for the synthesis of .alpha., .beta.-unsaturated ketones represented by general formula ##STR1## reacting aldehydes represented by general formulaR.sup.1 CHO(where R.sup.1 is as defined above) with alkali metal salt of acetoacetic acid represented by general formula ##STR2## (where M.sup..sym. is an alkali metal ion), in the presence as a catalyst of 3-azabicyclo[3,2,2]nonane, a cyclic secondary amine represented by general formula (1) ##STR3## a cyclic secondary amine represented by general formula (2) ##STR4## (where, l is 1 or more and up to 6, a ring with N is a 6-membered, 7-membered or 8-membered ring, the two neighbors of N are methylene, R.sup.3 is a lower alkyl group, its substitution position is at a carbon atom other than two those adjacent to N, and ##STR5## is an alicyclic group or a phenol group), or a secondary amine represented by general formula (3)CH.sub.3 NHCH.
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: January 16, 1996
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Keiichi Tsukashima, Masashi Nakajima, deceased, Masayoshi Fujimaru, Kenji Suzuki
  • Patent number: 5481029
    Abstract: A process for preparing ketones, for example CF.sub.3 C(O)CH.sub.3, CF.sub.3 C(O)CH.sub.2 C(O)CF.sub.3 and CF.sub.3 C(O)CF.sub.2 H, in which .beta.-ketoesters are transesterified and decarboxylated using a carboxylic acid, for example trifluoroacetic acid, in the presence of a catalyst, particularly an "onium" salt of a carboxylic acid or an effective amount of a proton-donating acid, preferably a sulfonic acid such as alkyl- or arylsulfonic acids, or a mineral acid. The process is advantageously carried out in the absence of water, so that no formation of acetals or hydrates occurs, and no dehydrating step is needed. The process is simple to carry out, and if transesterification is carried out with a sufficiently active carboxylic acid, for example with trifluoroacetic acid, the presence of an additional catalyst is unnecessary.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: January 2, 1996
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Johannes Eicher, Werner Rudolph, Kerstin Eichholz
  • Patent number: 5468905
    Abstract: Compounds represented by general formulas (I) and (II), useful as the intermediates for agricultural chemicals, particularly herbicidal compounds, wherein R.sup.1 and R.sup.2 represent each hydrogen, alkyl or COOR.sup.3 :R.sup.3 represents alkyl: and R.sup.4 represents alkyl.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: November 21, 1995
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Junji Suzuki, Masami Hatano, Shinichi Imaizumi
  • Patent number: 5468775
    Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is from the group consisting of COOCH.sub.3 and COOC.sub.2 H.sub.5 ; R.sup.1 is from the group consisting of H and CH.sub.3 ; R.sup.2 is from the group consisting of H when R.sup.1 is CH.sub.3 and CH.sub.3 when R.sup.1 is H; and R.sup.3 is from the group of first radicals consisting of benzyl, phenethyl, disubstituted phenyl and trisubstituted phenyl. The substituted species are second radicals having positive lipophilicity selected from the group consisting of F, Cl, Br, and I.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: November 21, 1995
    Assignee: Howard University
    Inventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
  • Patent number: 5428174
    Abstract: .alpha.,.beta.-Unsaturated ketones of the general formula I ##STR1## where R is an organic radical, are prepared by reacting a corresponding aldehyde R--CHO with acetoacetic acid or one of its salts in the presence of an amine in a two-phase reaction mixture by a process in which the reaction is carried out at a pH of from 6 to 8 in the presence of a catalytic amount of a primary amine.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: June 27, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5359126
    Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: October 25, 1994
    Assignee: Eastman Chemical Company
    Inventor: Charles A. McCombs
  • Patent number: 5344992
    Abstract: There is disclosed a process for the preparation of 1,3-diketones of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.20 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, NO.sub.2, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, C.sub.7 -C.sub.9 phenylalkyl or a radical of formula II--A--X--R.sub.4 (II)whereinA is C.sub.1 -C.sub.12 alkylene, phenylene or phenylene which is substituted by halogen, hydroxy, NO.sub.2, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.12 alkylene which is substituted by hydroxy, halogen and/or alkoxy,X is oxygen or sulfur, andR.sub.4 is hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy,C.sub.1 -C.sub.4 alkyl, NO.sub.2 and/or C.sub.1 -C.sub.4 alkoxy, or is C.sub.7 -C.sub.9 phenylalkyl, andR.sub.3 is hydrogen, C.sub.1 -C.sub.20 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, C.sub.1 -C.sub.4 alkyl, NO.sub.2 and/or C.sub.1 -C.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: September 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Drewes, Hans-Helmut Friedrich, Hans-Ludwig Mehner, Bernd Braun, Walter Wecht
  • Patent number: 5298666
    Abstract: The invention provides a method for converting a lactone of a diamondoid compound to the hydroxyketone of the diamondoid compound wherein the hydroxyl group and the carbonyl group are separated by at least one bridgehead carbon comprising reacting an anhydride containing from about 2 to about 20 carbon atoms with the lactone of the diamondoid compound in the presence of acid.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: March 29, 1994
    Assignee: Mobil Oil Corporation
    Inventor: Dong-Ming Shen
  • Patent number: 5254739
    Abstract: A process is described for the production of the known intermediate cyclopropylmethylketone which delivers a high yield, few side products, high reaction efficiency and turnover, and is more viable practically and commercially. In the presence of an excess of a Periodic Table Group I or Group II metal halide or quaternary phosphonium halide, .alpha.-acetyl-.gamma.-butyrolactone is led continuously into a reaction vessel at 170.degree.-200.degree. C. and cyclopropylmethylketone distilled off continuously. The halide is recovered and recycled in the process.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: October 19, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Roger Hunston, Rudolf Waditschatka
  • Patent number: 5210314
    Abstract: A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I ##STR1##where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II ##STR2##where R is H (a) or OH (b), with trifluoroacetic acid, reacting the resulting novel trifluoroacetate of the formula III ##STR3##with triphenylphosphine, and reacting the resulting novel triphenylphosphonium trifluoroacetate of the formula IV ##STR4##with 2,7-dimethyl-2,4,6-octatriene-1,8-dial under the conditions of a Wittig synthesis. The present invention also relates to the novel trifluoroacetates of the formula III and the corresponding triphenylphosphonium trifluoroacetates of the formula IV.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Joachim Paust, Werner Hoffmann
  • Patent number: 5130492
    Abstract: A process for the production of squaric acid by halogenation either of pure 3-acetoxy-2-cyclobuten-1-one or of a distillation residue of diketene production containing 3-acetoxy-2-cyclobuten-1-one to a cyclobutenone of formula: ##STR1## and then hydrolysis of these cyclobutenones to squaric acid. The halogenated cyclobutenones are intermediate products in the process.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: July 14, 1992
    Assignee: Lonza Ltd.
    Inventors: Thomas Scholl, Barry Jackson
  • 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: 5118847
    Abstract: 3-Hydroxy-2-cyclobuten-1-one salts of the general formula: ##STR1## wherein R is an ammonium group of the general formula: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different in meaning and each is a hydrogen atom, a lower alkyl group or a cycloalkyl group or R is an alkali metal atom. The salts according for formula I are obtained by the reaction of pure 3-acetoxy-2-cyclobuten-1-one, or 1,3-cyclobutanedione or a distillation residue of the diketene production containing 3-acetoxy-2-cyclobuten-1-one, with a base. The base can be an amine of the general formula: ##STR3## wherein R.sub.1, R.sub.2, and R.sub.3 have the above-mentioned meaning, or an alkali metal alcoholate or an alkali metal hydroxide. The salts according to formula I are suitable for the production of squaric acid, by their being halogenated in a first step and then being hydrolyzed to squaric acid in a second step.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: June 2, 1992
    Assignee: Lonza Ltd.
    Inventors: Barry Jackson, Thomas Scholl
  • Patent number: 5041613
    Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5030739
    Abstract: The invention is directed to a process for the catalytic oxidation of an isoprenoid containing at least one allylic hydrogen atom, which process comprises reacting the isoprenoid with oxygen or an oxygen-containing gas in an inert solvent in the presence of a N-hydroxydicarboxylic acid imide of the formula ##STR1## wherein A-B stands for CH.sub.2 -CH.sub.2, CH.dbd.CH, an aromatic hydrocarbon residue or a group derived from one of these groups in which one or more hydrogen atoms is/are replaced by alkyl or halogen,to produce a primary of secondary hydroperoxide.The process of the invention is suitable for the manufacture of steroids, vitamins, odorant substances, carotinoids and the like.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffman-La Roche Inc.
    Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
  • Patent number: 5015779
    Abstract: A method for the manufacture of the four geometric isomers of 4(2-butenylidene)-3,5,5-trimethyl-2-cyclohexen-1-one is provided. The process comprises pyrolyzing a compound of the formula ##STR1## wherein R represents lower-alkyl-oxycarbonyl, aryl-oxycarbonyl, or, preferably, lower-alkanoyl, benzoyl or substituted benzoyl.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: May 14, 1991
    Assignee: Givaudan Corporation
    Inventors: Daniel Helmlinger, Frank Kienzle, Erich Widmer
  • Patent number: 4950763
    Abstract: Ketones of the general formula (I) ##STR1## where R.sup.1 and R.sup.2 independently of one another are each alkyl, cycyloalkyl, arylalkyl, aryl or hetaryl, and one or more of the radicals R.sup.1 and R.sup.2 carry one or more hydrogen atoms on the .alpha.-carbon atom, are prepared by reacting two carboxylic acids of the general formulae (IIa/IIb), R.sup.1 --COOH (IIa) and R.sup.2 --COOH (IIb) or by reacting a carboxylic acid R.sup.1 --COOH (IIa) and a ketone ##STR2## or by reacting a mixture of IIa, IIb and Ib, in the gas phase in the presence of a catalyst, by a process in which a catalyst is used whose active material contains at least 50% by weight of titanium dioxide having a specific surface area greater than 10 m.sup.2 /g.0.
    Type: Grant
    Filed: July 18, 1989
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Charles Schommer, Klaus Ebel, Toni Dockner, Matthias Irgang, Wolfgang Hoelderich, Harald Rust
  • Patent number: 4892966
    Abstract: The invention is concerned with a novel process for the manufacture of compounds of the formula ##STR1## wherein R.sup.1 signifies C.sub.1-5 -alkyl, especially methyl, ethyl, propyl or isopropyl, and the radicals R.sup.2 each independently represent hydrogen or C.sub.1-5 -alkyl, especially hydrogen or methyl, ethyl, propyl or isopropyl.The process is characterized in that a compound of the formula ##STR2## wherein R stands for C.sub.1-4 -alkoxy, chlorine, bromine or C.sub.1-4 -alkanoyloxy, R.sup.1 and R.sup.2 have the above significance and R.sup.3 represents C.sub.1-4 -alkyl.is hydrolyzed and subjected to an aldol condensation and, where R=C.sub.1-4 -alkoxy, the reaction product is subsequently subjected to an acid treatment.The compounds I are for the most part known flavoring substances.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: January 9, 1990
    Assignee: Givaudan Corporation
    Inventor: Hans J. Wild
  • Patent number: 4885395
    Abstract: Alpha,beta-unsaturated ketones of the formula (I) ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, alkenyl of 1 to 12 carbon atoms, cycloalkyl, aryl, aralkyl or alkylaryl, are prepared by converting the corresponding .alpha.-hydroxy, alkoxy or carboxy compound in the presence of an acidic catalyst.Preferred starting materials are 3-methyl-3-hydroxy-butan-2-one, 3-methyl-3-hydroxypentan-2-one and 3-pentamethylene-3-hydroxypropan-2-one, and preferred catalysts are zeolites of the pentasil type.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: December 5, 1989
    Assignee: BASF Aktiengsellschaft
    Inventors: Wolfgang Hoelderich, Kurt Schneider, Leopold Hupfer
  • Patent number: 4866210
    Abstract: Ketones of the formula ##STR1## where R.sup.1 to R.sup.3 are each hydrogen and R.sup.1 to R.sup.4 are each alkyl of 1 to 12 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, aryl, aralkyl or alkylaryl, which each in turn may be substituted, or R.sup.1 and R.sup.2 and R.sup.3 together with the carbon atoms to which they are bonded form a cycloalkane, are prepared by reacting ketones of the formula ##STR2## where one of R.sup.1, R.sup.2, R.sup.3 and R.sup.5 is hydroxyl, alkoxy or carboxyl while the remaining R.sup.1 to R.sup.4 have the abovementioned meanings, with hydrogen in the presence of acid catalysts supporting one or more hydrogenation components, zeolites of the pentasil type being particularly suitable.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: September 12, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Leopold Hupfer, Kurt Schneider
  • Patent number: 4794193
    Abstract: Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: December 27, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
  • Patent number: 4739114
    Abstract: This invention relates to a novel method of preparing 3-alkyl-substituted glutaric acids and 2-alkyl-substituted succinic acids from 5-alkyl-substituted-1,3-cyclohexane-diones or 3-alkyl-substituted-5-ketohexanoic acids via transition-metal catalyzed oxidation.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: April 19, 1988
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Young J. Lee, Robert C. Ligon, Herbert E. Johnson
  • Patent number: 4700007
    Abstract: An improvement in a process for preparing a macrocyclic ketone having from 12 to 18 carbon atoms which comprises intramolecular cyclization of a lower alcohol diester of a straight chain alkanedicarboxylic acid having from 12 to 18 carbon atoms by acyloin condensation and reduction of the resulting 2-hydroxycycloalkanone is disclosed. The improvement comprises conducting the acyloin condensation in a water-immiscible organic solvent having a boiling point of not lower than 40.degree.C., subjecting the resulting organic solvent solution containing the 2-hydroxycycloalkanone to reduction, and conducting the reduction in the copresence of said organic solvent and water. The macrocyclic ketone can be prepared at high efficiency.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: October 13, 1987
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Hiroshi Okino, Seiichi Uchida, Keita Matsushita
  • Patent number: 4695673
    Abstract: An acylated 1,3-dicarbonyl compound is produced by rearrangement of the corresponding enol ester in the presence of a cyanide source. In one embodiment the cyanide source is employed with a molar excess of a moderate base, with respect to the enol ester. In another embodiment, the cyanide source is a stoichiometric amount, with respect to the enol ester, of potassium or lithium cyanide and a catalytic amount of a crown ether is used.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: September 22, 1987
    Assignee: Stauffer Chemical Company
    Inventors: James B. Heather, Pamela D. Milano
  • Patent number: 4673759
    Abstract: A process for the preparation of 2-alkyl cyclopent-2-enones having the formula: ##STR1## wherein R is as defined hereinafter. An .alpha.-olefin having the formula CH.sub.2 .dbd.CH--CH.sub.2 R is oxidized to the corresponding epoxide. The epoxide is reacted with an alkylating agent having the formula Na.sup.+ [CH(COOR").sub.2 ].sup.-, wherein R" is an ethyl, an isopropyl, or an isobutyl radical. An .alpha.-carbalkoxy-.gamma.-alkyl lactone is obtained, which, through saponification and decarboxylation, yields a .gamma.-alkyl lactone having the formula: ##STR2## which is reacted with a protic acid, thereby obtaining, by cyclization, the desired 2-alkylcyclopent-2-enone. The obtained products are intermediates for the production of pharmaceutical products and of drugs for veterinary use, in particular prostaglandin.
    Type: Grant
    Filed: March 3, 1986
    Date of Patent: June 16, 1987
    Assignee: Montedison S.p.A.
    Inventor: Enrico Dalcanale
  • Patent number: 4608442
    Abstract: A process for producing a compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, an alkyl group or an alkenyl group and R.sub.2 is an alkyl group, an alkenyl group or an alkynyl group, which comprises treating a compound of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and R is a hydrogen atom or a lower alkyl group in the presence of an acidic substance and water.
    Type: Grant
    Filed: July 10, 1984
    Date of Patent: August 26, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4582940
    Abstract: There is described a method for synthesizing 3-nitro-1,2-cyclopentanedione salts which are substituted in the 4-position with an alkyl substituent and in the 5-position with an electron withdrawing substituent. The method comprises the addition and spontaneous cyclization reaction of a nitro olefin with a pyruvate anion. The salts can be converted to the nitro diones or used as intermediates in the preparation of amino reductones.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: April 15, 1986
    Assignee: Polaroid Corporation
    Inventor: Charles E. Whitten
  • Patent number: 4575570
    Abstract: A process for producing alpha,beta-unsaturated ketones represented by the following general formula ##STR1## wherein R.sub.1 represents a hydrocarbon radical, R.sub.2 represents an organic radical bonded through a carbon-carbon bond, R.sub.3 and R.sub.4 represent a hydrogen atom or a hydrocarbon radical, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be straight-chained or form a ring in arbitrary combinations,which comprises contacting an alpha-disubstituted-beta-keto acid ester represented by the general formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined, and R.sub.5, R.sub.6, R.sub.7 and R.sub.8 represent a hydrogen atom or a hydrocarbon radical,with a catalyst consisting essentially of (a) a compound of a platinum-group metal and optionally (b) a monodentate ligand (b).
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: March 11, 1986
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Hideaki Kataoka, Toshiro Yamada, Kuniaki Goto, Jiro Tsuji
  • Patent number: 4554363
    Abstract: Process for the preparation of bicyclic ketones containing blocked hydroxy groups, of general Formula I ##STR1## wherein R.sub.1 is the residues --CH.sub.2 OR.sub.2 wherein R.sub.2 means benzyl, dimethyl-tert-butylsilyl, diphenyl-tert-butylsilyl, dimethylphenylsilyl, tribenzylsilyl, or tetrahydropyranyl, ##STR2## with R.sub.2 having the meanings given above, R.sub.4 meaning hydrogen or methyl, and R.sub.5 meaning a straight-chain or branched-chain, saturated or unsaturated alkyl residue which can contain fluorine, chlorine, 1,2-methylene, 1,1-trimethylene, or methoxy substitutents, or a CH.sub.2 --X-Aryl residue with X meaning CH.sub.2 or O and Aryl meaning phenyl or a heterocyclic residue, which residues can be substituted by methyl, methoxy, fluorine, chlorine, bromine, or trifluoromethyl, or ##STR3## with the meanings for R.sub.2, R.sub.4, and R.sub.5 as indicated above, and R.sub.3 having the meanings set forth for R.sub.2, it being possible for R.sub.3 to be identical to R.sub.2 or different from R.sub.
    Type: Grant
    Filed: June 23, 1983
    Date of Patent: November 19, 1985
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbrueggen
  • Patent number: 4532359
    Abstract: Described is a novel process for preparing 1,2,3,3,5,6-hexamethyl- bicyclo [2,2,2.] oct-5-en-2-ol by using 2,6,6-trimethylcyclohexa-2,4-diene-1-one as a starting material.
    Type: Grant
    Filed: April 20, 1984
    Date of Patent: July 30, 1985
    Assignee: International Flavors & Fragrancs Inc.
    Inventors: William J. Evers, Braja D. Mookherjee, Anton Van Ouwerkerk, Augustinus G. Van Loveren
  • Patent number: 4528400
    Abstract: Disclosed is a method for the preparation of ketones by a catalytic vapor phase reaction of using reactants such as ketones with carboxylic acids and/or carboxylic acid precursors. An example of such a reaction is that of acetone with pivalic acid over a ceria-alumina catalyst at a temperature of nearly 470.degree. C. to produce pinacolone.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: July 9, 1985
    Assignee: SDS Biotech Corporation
    Inventors: Richard L. Cryberg, Russell M. Bimber
  • Patent number: 4504671
    Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4496766
    Abstract: A process for producing an .alpha.,.beta.-unsaturated ketone of the general formula ##STR1## wherein R.sub.1 represents a hydrocarbon group, R.sub.2 represents an organic group bonded through a carbon-carbon bond, R.sub.3 and R.sub.4 represent a hydrogen atom or a hydrocarbon group, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be linear or may form a ring when taken together in arbitrary combinations,which comprises contacting an .alpha.-disubstituted-.beta.-keto acid ester of the general formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined, and R.sub.5, R.sub.6 and R.sub.7 represent a hydrogen atom or a hydrocarbon group,with a catalyst consisting essentially of (a) a compound of a platinum-group metal and (b) and .alpha.,.omega.-alkylenedi(disubstituted)phosphine.
    Type: Grant
    Filed: May 4, 1983
    Date of Patent: January 29, 1985
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Jiro Tsuji, Isao Shimizu
  • Patent number: 4496767
    Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.
    Type: Grant
    Filed: October 18, 1983
    Date of Patent: January 29, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4481372
    Abstract: Described is a novel process for preparing allyl alpha and beta ionones defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and wherein the wavy lines represent the cis or trans juxtaposition of the acyl and cyclohexenyl rings about the carbon-carbon double bond which is alpha to the acyl moiety, and intermediates used in said process defined according to the structure: ##STR2## wherein the wavy lines and dashed lines are defined supra and wherein R.sub.1 represents hydrogen or allyl and Z represents methyl or OR.sub.2 and wherein R.sub.2 represents methyl or ethyl.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: November 6, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz
  • Patent number: 4458093
    Abstract: Described is the hexadienoyl cyclohexene derivative defined according to the structure: ##STR1## which may either be in the form of a mixture of Z, Z; E, E; Z, E or E, Z isomers or the individual isomers themselves having the structures: ##STR2## a process for preparing same, intermediates useful in said process defined according to the structure: ##STR3## wherein R represents ethyl or methyl and organoleptic uses of the hexadienoyl cyclohexene derivatives in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes and perfumed articles (e.g. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers); foodstuffs, chewing gums, medicinal products, toothpastes and chewing tobaccos; smoking tobaccos and smoking tobacco articles.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: July 3, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Joseph A. McGhie, Manfred H. Vock
  • Patent number: 4449007
    Abstract: A process comprising the steps of reacting 1-acetyl-3,3-dimethylcyclohexane with an alkyl acetate, thereby forming a diketone having the structure: ##STR1## reacting the said diketone with an allyl halide to form a substituted diketone having the structure: ##STR2## which is transformed into the compound having the structure: ##STR3## by means of a retro-Claisen reaction.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: May 15, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker
  • Patent number: 4424166
    Abstract: In the preparation of a 1,1-dihalogenoalkene of the formula ##STR1## in which R.sup.1 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, andX.sup.1 and X.sup.2 each independently is a halogen atom,wherein a carbonyl compound of the formula ##STR2## is reacted with a trihalogenoacetate of the formula ##STR3## in which X.sup.3 is a halogen atom, andM.sup..sym. is an alkali metal ion or one equivalent of an alkaline earth metal ion,in the presence of an approximately equimolar amount of a phosphorus-containing compound, the improvement which comprises employing as said phosphorus-containing compound a phosphorous acid trialkyl ester or a phosphorous acid triamide and effecting the reaction at a temperature between about 0.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: January 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4414418
    Abstract: Process for the production of dimedone from isophorone. The isophorone is converted in the presence of a solvent with ozone into an ozone-addition product. An alcohol corresponding to the ester radical is added at the latest after the formation of the ozone-addition product for the formation of the intermediate product, 3,3-dimethyl-5-oxo-hexanoic acid ester. The ozone addition product is heated in the presence of acids to a temperature of 20.degree. to 150.degree. C. The 3,3-dimethyl-5-oxo-hexanoic acid ester is isolated thereby. The ester is then converted in a further step into dimedone by treatment of the ester with an alkali alcoholate in an anhydrous milieu.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: November 8, 1983
    Assignee: Lonza Ltd.
    Inventor: Pavel Lehky
  • Patent number: 4409400
    Abstract: Cyclohexane-1,3-diones are prepared by passing .delta.-ketocarboxylic acid esters in the gaseous phase over a temperature of from 250.degree. C. to 500.degree. C. at a catalyst. The catalyst contains at least one element of groups III B or IV B of the Periodic System in the form of a compound. Particularly preferred catalysts are thorium compounds on charcoal carriers.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: October 11, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Karl E. Mack, Hansjorg Hey
  • Patent number: 4399310
    Abstract: A process is disclosed for making 1,3-cyclic diones by vapor-phase cyclization of delta-keto carboxylic acid esters over a carbon catalyst bed. The delta-keto ester is conveyed through the catalyst bed by a carrier gas characterized by being liquid at 25.degree. C. and having a sufficiently high boiling point that the carrier gas is easily condensable under ambient conditions. The delta-keto ester is highly soluble in the liquid carrier, while the cyclic dione product of the ester has very low solubility in the liquid carrier. Use of the described carrier in vapor-phase cyclization of delta-keto esters allows efficient separation of cyclic dione product and unreacted starting material from the carrier after the cyclization reaction.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: August 16, 1983
    Assignee: Koppers Company, Inc.
    Inventor: Nicholas P. Greco
  • Patent number: 4386222
    Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: May 31, 1983
    Assignee: General Electric Company
    Inventor: James A. Cella
  • Patent number: 4385186
    Abstract: The present invention relates to a method for producing an optically active (+)-(s)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone which comprises reacting (.+-.)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate of the formula (II), ##STR1## with an optically active (+)-.alpha.-phenyl-.beta.-p-tolylethylamine to produce diastereomer salts, separating an optically active (-)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate by making use of a solubility difference between the diastereomer salts, and then hydrolyzing said optically active acid phthalate in water or a solvent containing water in the presence or absence of a base below the small excess of the stoichiometric amount, and novel (.+-.)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate and its production.
    Type: Grant
    Filed: June 18, 1980
    Date of Patent: May 24, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima