Isomerization Patents (Class 568/341)
  • Patent number: 6388140
    Abstract: A cyclododecanone compound is produced in a high reaction rate, with a high conversion of the starting compound, and with a high selectivity to and a high yield of the target compound by isomerizing an epoxycyclododecane compound in the presence of a catalyst comprising lithium bromide and/or lithium iodide, without using a solvent or in a non-polar solvent, in an inert gas atmosphere, while substantially no polymeric compounds having a high boiling temperature is produced.
    Type: Grant
    Filed: February 15, 2001
    Date of Patent: May 14, 2002
    Assignee: Ube Industries, Ltd.
    Inventors: Ryoji Sugise, Shuji Tanaka, Kohichi Kashiwagi, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
  • 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
  • Patent number: 6329535
    Abstract: A process for preparing esterified chroman compounds from 2,6,6-trimethylcylohex-2-ene-1,4-dione, wherein the esterified intermediates are reacted directly to give the desired chroman derivatives without an additional purification step.
    Type: Grant
    Filed: October 20, 2000
    Date of Patent: December 11, 2001
    Assignee: Degussa Dental GmbH & Co. KG
    Inventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
  • Publication number: 20010049455
    Abstract: The present invention provides a method for efficiently producing a 2-alkyl-2-cyclopentenone as well as a method for producing a jasmonate derivative by using the same. That is, in the present invention, the compound (2) is obtained by reacting an amine and a hydrogen halide with the compound (1) at a specific ratio to carry out isomerization reaction or by reacting a catalyst comprising an amine and a hydrogen halide with the compound (3) to carry out dehydration-isomerization reaction.
    Type: Application
    Filed: March 13, 2001
    Publication date: December 6, 2001
    Applicant: Kao Corporation
    Inventors: Takahiro Asada, Yoshiharu Ataka, Junji Koshino
  • Publication number: 20010023071
    Abstract: A cyclododecanone compound is produced in a high reaction rate, with a high conversion of the starting compound, and with a high selectivity to and a high yield of the target compound by isomerizing an epoxycyclododecane compound in the presence of a catalyst comprising lithium bromide and/or lithium iodide, without using a solvent or in a non-polar solvent, in an inert gas atmosphere, while substantially no polymeric compounds having a high boiling temperature is produced.
    Type: Application
    Filed: February 15, 2001
    Publication date: September 20, 2001
    Applicant: Ube Industries, Ltd.
    Inventors: Ryoji Sugise, Shuji Tanaka, Kohichi Kashiwagi, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
  • Patent number: 6274771
    Abstract: For the continuous manufacture of &bgr;-isophorone by isomerization under homogeneous catalysis of &agr;-isophorone, the steps of introducing the &agr;-isophorone and a solution of an alkaline hydroxide into a reaction region, bringing the reaction mixture to reflux at a temperature at least equal to 150° C. under a equal P1 of less than or equal to atmospheric pressure, continuously and simultaneously removing from the reaction mixture: &bgr;-isophorone vapor, by distillation under a pressure P2 less than P1 and at a temperature at most equal to 150° C., and heavy products, at a rate, so that their content by weight is at most equal to 7% in the reaction mixture, and continuous returning the distillation to the reaction region.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: August 14, 2001
    Assignee: Atofina
    Inventors: Francois Mongenet, Rémy Teissier
  • Patent number: 6274772
    Abstract: This invention relates to a continuous process for the manufacture of &bgr;-isophorone by isomerization under homogeneous catalysis of &agr;-isophorone. The process consists of introducing &agr;-isophorone and a solution of an alkaline hydroxide into a reaction region at a temperature ranging from 150° C. to 216° C., simultaneously removing by distillation a fraction comprising an amount by weight of &bgr;-isophorone ranging from 30% to 90%, drawing off the heavy products and then rectifying the fraction removed from the reaction mixture by distillation.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: August 14, 2001
    Assignee: Atofina
    Inventors: Rémy Teissier, Georges Martino-Gauchi
  • Patent number: 6265617
    Abstract: A process for the preparation of 3,5,5-trimethylcyclohexa-3-en-1-one (&bgr;-isophorone) by isomerization of 3,5,5-trimethylcyclohexa-2-en-1-one (&agr;-isophorone) in the liquid phase in the presence of a salt-like or organometallic catalyst. By using catalytic quantities of alkali-metal salts or alkaline-earth salts and/or their organometallic compounds, and without addition of a further auxiliary substance, the space-time yield in the preparation of &bgr;-isophorone is high. &bgr;-Isophorone is particularly suitable as an intermediate product for the preparation of ketoisophorone.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: July 24, 2001
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Steffen Krill, Stephan Kretz, Hans-Joachim Hasselbach, Klaus Huthmacher, Rainer Hahn, Hermann Schmitt
  • Patent number: 6198004
    Abstract: The invention relates to a process for converting alpha acid and isoalpha acids to tetrahydroisoalpha acid. The process comprises isomerizing an alpha acid to produce isoalpha acid and hydrogenating the isoalpha acid in the presence of a noble metal catalyst wherein, the noble metal catalyst is added incrementally or continuously throughout the hydrogenation step. The invention also relates to tetrahydroisoalpha acids made by the above process.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: March 6, 2001
    Assignee: Haas Hop Products, Inc.
    Inventors: John Paul Maye, Jianping Xu, George Gauthier, Scott W. Weis
  • Patent number: 6005147
    Abstract: A method of producing 3,5,5-trimethylcyclohexa-3-ene-1-one (.beta.-isophorone) including a catalyst of an oxide or mixed oxide of at least one element of the groups IIa, VIII, Ib, IIIa and Va of the periodic system. Isomerization is carried out without the addition of an organic base. The space-time yield in the production of .beta.-isophorone by the isomerization of .alpha.-isophorone is at a level suitable for an industrial application. .beta.-isophorone is especially suitable as an intermediate product for producing ketoisophorone.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: December 21, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Steffen Krill, Gunes Giray, Klaus Huthmacher, Frank Hubner, Herbert Tanner
  • Patent number: 5917093
    Abstract: Unsaturated organic compounds, in particular .alpha.-acids and .beta.-acids, are purified prior to hydrogenation by mixing them with an adsorbent capable of adsorbing catalyst poisons, preferably activated carbon, and separating the adsorbent containing the catalyst poisons to recover the thus purified unsaturated organic compounds. A significant reduction in the use of hydrogenation catalyst is realized.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: June 29, 1999
    Assignee: Miller Brewing Company
    Inventors: Patrick L. Ting, Jay R. Refling, Michael A. VanSanford, Henry Goldstein
  • Patent number: 5908956
    Abstract: This method provides trimethylhydroquinone diester by using a recyclable catalyst which shows high activity and operability in the reaction, while reducing the risk of corrosion of the reactor. The method for the production of 2,5,6-trimethylhydroquinone diester comprises reacting 2,6,6-trimethylcyclohexe-2-en-1,4-dione with an acylating agent in the presence of a solid catalyst. The acylating agent includes a C.sub.2-4 carboxylic acid anhydride (e.g. acetic anhydride) and a C.sub.2-4 carboxylic acid halide (e.g. acetyl chloride). The solid catalyst includes a solid acid catalyst (e.g. strongly or super-strongly acidic ion exchange resin, compound oxide, zeolite, heteropoly acid).
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: June 1, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Ikuo Takahashi, Masahiro Chikamori
  • Patent number: 5907065
    Abstract: A method of producing 3,5,5-trimethylcyclohexa-3-ene-1-one (.beta.-isophorone) by isomerization of 3,5,5-trimethylcyclohexa-2-ene-1-one (.alpha.-isophorone) in a liquid phase in the presence of a homogeneous or heterogeneous catalyst in which a mixture with a relatively low concentration of .beta.-isophorone is drawn off from the reaction container and the .beta.-isophorone isolated by vacuum distillation. .beta.-isophorone is an important synthetic structural element for the production of carotinoids, vitamins and pharmaceutical products.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: May 25, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Steffen Krill, Gunes Giray, Frank Hubner, Rainer Hahn, Klaus Huthmacher, Herbert Tanner
  • Patent number: 5886231
    Abstract: A process for preparing a compound of formula (I): ##STR1## by rearrangement of a compound of formula (II): ##STR2## in a non-polar solvent in the presence of a cyanide source, an alkali or alkaline earth metal carbonate, a phase transfer catalyst and 1-6 moles of water with respect to the compound of formula (II).
    Type: Grant
    Filed: June 24, 1997
    Date of Patent: March 23, 1999
    Assignee: Zeneca Limited
    Inventors: Stephen Martin Brown, Howard Rawlinson
  • Patent number: 5576462
    Abstract: A process for the preparation of .alpha.-hydroxyketones of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 denote hydrogen or C.sub.1 -C.sub.8 alkyl orR.sub.1 and R.sup.3 together form a C.sub.2 -C.sub.10 alkylene chain optionally mono- to tri-substituted by methyl and/or ethyl andR.sup.5 denotes hydrogen, methyl or ethyl,from 2,3-epoxyalcohols of the general formula II ##STR2## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have the above meanings, at temperatures of from -10.degree. to 120.degree. C. and pressures of from 0.01 to 20 bar in the presence of a catalyst, wherein the catalyst used is a hydridocobalt compound, and the preparation of 2,3-epoxyalcohols II from 3-hydroperoxy alkenes III and their preparation from alkenes IV using oxygen or gas mixtures containing oxygen.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: November 19, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Rieber, Joaquim H. Teles
  • Patent number: 5334768
    Abstract: The invention relates to a process for the preparation of cycloalkanone and optionally cycloalkanol by causing a mixture containing cycloalkylhydroperoxide to react with cycloalkene under the influence of a catalyst, characterised in that the reaction is carried out with a short measure of cycloalkene relative to the cycloalkylhydroperoxide, under such conditions that virtually all of the cycloalkene reacts to cycloalkene oxide and optionally cycloalkanol and/or cycloalkanone, after which the mixture, optionally after decomposition of cycloalkylhydroperoxide and distillation of cycloalkane, is subjected to a first separation, in which cycloalkene oxide--and optionally other components--is separated, after which the cycloalkene oxide in the separated mixture is isomerised to substantially cycloalkanone, after which the cycloalkanone obtained--and optionally cycloalkanol--is recovered.
    Type: Grant
    Filed: February 3, 1993
    Date of Patent: August 2, 1994
    Assignee: DSM N.V.
    Inventors: Johannes G. van Hinsberg, Cornelis G. M. van de Moesdijk, Ivo Spaargaren, Otto E. Sielcken
  • Patent number: 5321164
    Abstract: Described is the 2(1-vinyl-5-hexenyl)cyclopentanone having the structure: ##STR1## a process for preparing same by reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## and then heating the resulting intermediate, and organoleptic uses of the compound having the structure: ##STR4## in perfumery.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: June 14, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William J. Fylak, Joseph A. Mc Ghie, Charles E. J. Beck
  • Patent number: 5296637
    Abstract: The present application discloses a novel and advantageous method for the preparation of essentially odor-free alkali metal tetrahydroisohumulate (THIH) which proceeds through isomerization of the essential alkali metal tetrahydrohumulate (THH) intermediate, which is in turn produced by the hydrogenation with two moles of hydrogen of a starting alkali metal humulate (H) at a pH of at least 10, the intermediate THH being thus produced with relative ease and in high yields and purity, which high yields and purity carry over to the ultimate end product, namely, to the essentially aroma-, odor-, and impurity-free THIH, which end product accordingly does not require steam-stripping or other cleanup procedure as is conventional for THIH produced from other sources or by other procedure.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: March 22, 1994
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Larry J. Stegink, James A. Guzinski, Paul H . Todd, Jr.
  • Patent number: 5276197
    Abstract: The invention is concerned with a process for the manufacture of beta-isophorone from alpha-isophorone by converting alpha-isophorone into beta-isophorone in the presence of a heterogeneous catalyst in the gas phase. The heterogenous catalyst used is especially an oxide or mixed oxide of the elements Mg, Al, Si and Ni.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: January 4, 1994
    Assignee: Hoffman-La Roche Inc.
    Inventors: Paul Nosberger, Adrian J. Vieth
  • Patent number: 5235110
    Abstract: The invention discloses a process for preparing a 2,3-di-substituted cyclopentanone mixture containing an enriched cis-2,3-di-substituted cyclopentanone which comprises heating a trans-2,3-di-substituted cyclopentanone in the presence of 100 ppm or less (weight basis) of a metal carbonate based on the cyclopentanone. The invention also discloses a fragrant composition comprising 20 to 50 wt % of 2,3-di-substituted cis-methyl (dihydro) jasmonates and 80 to 50 wt % of 2,3-di-substituted (dihydro) trans-methyl (dihydro) jasmonates. The fragrant composition has jasmine flower-like fragrance.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: August 10, 1993
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Toshiro Yamada, Hiroshi Fujisawa, Hideyuki Tanaka
  • Patent number: 5185470
    Abstract: Provided is a process which comprises conducting the ring-closure of pseudoirone in the presence of chlorosulfonic acid, which is inexpensive, to obtain in a high yield the .alpha.-cis form of irone, which has nearly the same fragrance as that of natural irones.
    Type: Grant
    Filed: February 5, 1992
    Date of Patent: February 9, 1993
    Assignee: Kuraray Company, Ltd.
    Inventors: Goro Asanuma, Yoshin Tamai
  • Patent number: 5166447
    Abstract: Cyclopentanones of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each an organic radical or R.sup.1 or R.sup.2 may be hydrogen and R.sup.3 is hydrogen or formyl, are prepared by a process in which a 2-formyl-3,4-dihydropyran of the general formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, a) where R.sup.3 is formyl, is converted in the presence of an acidic heterogeneous catalyst at from 50.degree. to 500.degree. C., andb) where R.sup.3 is hydrogen,b.sub.1) is reacted with water or an alcohol in the presence of an acidic heterogeneous catalyst at from 100.degree. to 500.degree. C. in the gas phase orb.sub.2) a compound II or an acrolein of the general formula III ##STR3## is reacted with water or with water in the presence of an acid or with an alcohol in the presence of an acid at from 150.degree. to 400.degree. C. in the liquid phase. Novel 2-formylcyclopentanones are obtained.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Tom Witzel
  • Patent number: 5155276
    Abstract: The invention concerns a process for the isomerization of humulon in a carbon dioxide-hops extract and a process for the isolation of isohumulon from the isomerized carbon dioxide-hops extract. Aluminium or an aluminium compound, preferably aluminium trioxide is added to the carbon dioxide-hops extract in such a concentration that the mole ratio of aluminium: alpha acid (alpha humulon) amounts to from 1:0.1 to 1:6. The mixture is then treated with high alkali hydroxide concentration at a temperature of from 80.degree. to 160.degree. C.Isohumulon is obtained from the extract by adding so much tempered water that the isohumulon share amounts to 1 to 10% and the temperature is reduced to 40.degree. to 45.degree. C., and after further cooling to room temperature, the alkali isohumulons are purified from the other components in conventional manner and optionally are transformed in the conventional way into isohumulons.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: October 13, 1992
    Assignee: Hopstabil Hopfenverarbeitungs GmbH
    Inventor: Herbert Paul
  • Patent number: 5113021
    Abstract: A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 12, 1992
    Assignee: Givaudan Corporation
    Inventors: Georg Frater, Daniel Helmlinger
  • Patent number: 5041678
    Abstract: Optically active isomers of alpha-damascone of formula ##STR1## wherein the wavy line designates a C--C bound of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula ##STR2## where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula ##STR3## where the asterisk identifies a center of chirality;index n stands for zero or 1;each of symbols R.sup.0 and R.sup.1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above;each of symbols R.sup.2 and R.sup.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: August 20, 1991
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Jose Galindo
  • Patent number: 5019297
    Abstract: Olefinically unsaturated secondary alcohols in which the carbon-carbon double bond and the alcohol functionality are separated only by methylene groups are isomerized to ketones by reacting a mixture composed of an olefinically unsaturated secondary alcohol and a catalyst effective amount of a substantially fully hydrogenated palladium catalyst at a temperature of from about 200.degree. C. to about 300.degree. C. and passing hydrogen through the reaction mixture until the iodine number of said reaction mixture is less than 10 and separating the catalyst from the ketone.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: May 28, 1991
    Assignee: Henkel Research Corporation
    Inventor: Michael J. Virnig
  • 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: 4970345
    Abstract: A process for preparing oxocyclopentenes of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl, which comprises subjecting a furan-carbinol of the formula: ##STR2## wherein R.sup.1 is as defined above and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl to rearrangement, subjecting the resultant hydroxycyclopentenone of the formula: ##STR3## wherein R.sup.1 and R.sup.3 are each as defined above to hydrogenation and subjecting the resulting hydroxycyclopentanone of the formula; ##STR4## wherein R.sup.1 and R.sup.2 are each as defined above to dehydration.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: November 13, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Masayoshi Minai
  • Patent number: 4950797
    Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
  • Patent number: 4918240
    Abstract: Beta acids, separated from hop extracts, are purified prior to hydrogenolysis by mixing with an aqueous solution of polyvalent metal ions, preferably edible ions such as magnesium or calcium ions, separating the aqueous beta acids from insoluble materials containing catalyst poisons, and recovering the thus-purified beta acids which are catalyst-poison free and in a form suitable for hydrogenolysis to 4-desoxy alpha acids.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: April 17, 1990
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Guzinski
  • Patent number: 4885397
    Abstract: A process for preparing a cyclic ketone from a cyclic epoxide, comprising the step of:contacting a cyclic epoxide with an alkali or alkaline-earth halide salt in the presence of a polar solvent at a temperature ranging from 120.degree. to 250.degree. C., wherein said cyclic epoxide is unsubstituted or substituted with one or more C.sub.1-5 alkyl or alkenyl groups, and wherein said cyclic epoxide comprises 7-20 ring carbon atoms, and contains up to 5 carbon-carbon multiple bonds.
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: December 5, 1989
    Assignee: Huels Aktiengesellschaft
    Inventor: Wilfried Bueschken
  • Patent number: 4845303
    Abstract: A process for the production of beta-isophorone from alpha-isophorone, comprising the steps of:(i) heating alpha-isophorone in the presence of an isomerization catalyst, said catalyst comprising a metal acetylacetonate, wherein said metal is selected from the group consisting of aluminum and the metals of Groups IVB, VB, VIB, VIIB and VIIIB of the periodic table, to produce beta-isophorone, and(ii) isolating said beta-isophorone.
    Type: Grant
    Filed: August 24, 1988
    Date of Patent: July 4, 1989
    Assignee: Huels Aktiengesellschaft
    Inventor: Hans Bellut
  • 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: 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: 4734529
    Abstract: The method for the isomerization of oxiranes of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 are hydrogen; R.sub.2 is alkyl or alkylene groups of 3 to 26 carbon atoms or the phenyl group which may also be substituted, and R.sub.4 is hydrogen or alkyl from 1 to 26 carbon atoms and in which the carbon atoms of the epoxy ring can also form components of a cyclic system, wherein as a catalyst there is used alkali iodide and a polyethyleneglycol with an average mol mass of 400 to 10,000 with a boiling point, preferably above the boiling point of the carbonyl compounds that are formed.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: March 29, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Marion Berg, Andreas Grund, Guenter Prescher
  • 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: 4694107
    Abstract: Ketones are prepared by isomerization of aldehydes at elevated temperatures over zeolites.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: September 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Rolf Fischer
  • 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: 4644084
    Abstract: Tetrahydroisohumulones are prepared from beta-acids without using objectionable organic solvents by treating the beta-acids to form desoxytetrahydrohumulones which are dissolved in an aqueous alcoholic caustic solution and then oxidized and isomerized with an oxygen-containing gas in the presence of metallic ion to form the desired tetrahydroisohumulones.
    Type: Grant
    Filed: February 3, 1986
    Date of Patent: February 17, 1987
    Assignee: Miller Brewing Company
    Inventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
  • Patent number: 4590296
    Abstract: Beta-acids are separated from alpha-acids in a hop extract without using organic solvents by bubbling CO.sub.2 through an aqueous hop extract having a pH of about 9.6 to about 13 to lower the pH to about 8.5 to about 9.5 to precipitate the beta-acids and leave the alpha-acids in the extract.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: May 20, 1986
    Assignee: Miller Brewing Company
    Inventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
  • Patent number: 4550211
    Abstract: Process for the preparation of the compounds of the formulae Ia and Ib ##STR1## wherein A. 2,4,4-trimethylcyclohex-2-en-1-one oxime of the formula IIb ##STR2## is treated with a strong aqueous acid at from 30.degree. to 80.degree. C., preferably 40.degree. to 70.degree. C.,B. the resulting ketone of the formula IIIb ##STR3## is oxidized in a conventional manner, and C. if desired, the resulting compound Ib is isomerized in a conventional manner.Compounds of the formula A ##STR4## where R is one of the following radicals: --CH(OH)--CH.sub.2 --CH.dbd.CH.sub.2 (IIIb), --CH(OH)--CH.sub.3 (IIIc), --CH.sub.2 OH (IIId), --CH(OH)--CH.dbd.CH.sub.2 (IIIe), --CH(OCOCH.sub.3)--CH.sub.3 (IIIf), --CH.sub.2 --OCOCH.sub.3 (IIIg), --CO--CH.sub.2 --CH.dbd.CH.sub.2 (Ib), --CO--CH.sub.3 (Ic) and --CO--CH.dbd.CH.sub.2 (Ie).The compounds IIIb to IIIg, Ib, Ic and Ie are useful scents and aromas, and furthermore may become important intermediates for novel carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 29, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Werner Hoffmann
  • Patent number: 4540797
    Abstract: Novel ethers of organic compounds containing chiral atoms of the formula ##STR1## wherein A is a hydrocarbonated chain of 1 to 10 groups, the said chain containing one or more heteroatoms, one or more unsaturations, the assembly of the groups constituting the chain may represent a mono- or polycyclic system, including a system of the spiro or endo type, the chain A can contain one or more chiral atoms or the lactone moiety can present a chirality due to the dissymmetric spatial configuration of the whole of the molecule and Z is selected from the group consisting of primary, secondary or tertiary alcohol moiety containing at least an asymmetric carbon atom, a phenol moiety substituted comprising at least one asymmetric carbon atom and a substituted alcohol or phenol moiety with a chirality due to the dissymmetric spatial configuration of the whole of the molecule, with the proviso Z is not (R) or (S) .alpha.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: September 10, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4540825
    Abstract: A method for producing 2-cyclopentenones represented by the formula, ##STR1## wherein R represents an alkyl, alkenyl, cycloalkyl, substituted or non-substituted aryl or aralkyl group, which comprises heating 4-cyclopentenones represented by the formula, ##STR2## wherein R has the same meaning as above, in the presence of 1,8-diaza-bicyclo[5,4,0]undecene or its organic acid salt.The 2-cyclopentenones are useful as an intermediate for perfumes, medicines and agricultural chemicals.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: September 10, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuyuki Shiota, Kunihiko Tanaka, Masayoshi Minai
  • Patent number: 4537995
    Abstract: A process of isomerizing branched aldehydes to ketones is provided which comprises contacting at isomerization conditions a branched aldehyde with a zeolite catalyst of the formula: ##EQU1## wherein M is selected from the group consisting of a mixture of alkali metal cations, especially sodium, and tetraalkylammonium cations, the alkyl groups of which preferably contain 2 to 5 carbon atoms, and x is at least 5. The contacting is conducted at a temperature of from about 200.degree. C. to about 600.degree. C. and at a pressure of from about 20 psig to about 100 psig. The branched aldehyde is contacted in the presence of water in a molar ratio of water-to-aldehyde of up to about 20 to 1.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: August 27, 1985
    Assignee: Celanese Corporation
    Inventors: H. Clay Linstid, III, Gerald S. Koermer
  • Patent number: 4532358
    Abstract: A process for the manufacture of 3-hydroxy-2,6,6,-trimethyl-2-cyclohexen-2-one, an intermediate in canthaxanthin synthesis, by isomerizing 1,1,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one in the presence of a palladium(O) complex of an acetone derivative of the formula ##STR1## wherein R.sup.1 and R.sup.2 are aryl and R.sup.3 and R.sup.4 are hydrogen or monovalent hydrocarbon groups optionally carrying a carbonyl function, a bis-(diphenylphosphino) derivative of the formula(R.sup.5).sub.2 P--R.sup.6 --P(R.sup.5).sub.2wherein R.sup.5 is phenyl or tolyl and R.sup.6 is a C.sub.2 --C.sub.4 -alkylene group optionally substituted with one or more inert organic groups, and a triarylphosphine of the formulaP(R.sup.7).sub.3wherein R.sup.7 is an optionally alkyl-substituted phenyl group.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: July 30, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4510329
    Abstract: A process for preparing cyclopentenolones of the formula ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl or alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: April 9, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Hiroshi Yamachika
  • Patent number: 4460792
    Abstract: Useful perfumery ingredients delta- and epsilon-damascone are prepared by a process which consists in an anionic cleavage, in the presence of a strong base of a diallyl alcohol of formula ##STR1## wherein the dashed lines in position 3 or 4 of the ring designate a double bond, followed by an isomerization of the terminal double bond of the thus obtained product by means of an acidic isomerizing agent.
    Type: Grant
    Filed: August 19, 1982
    Date of Patent: July 17, 1984
    Assignee: Firmenich S.A.
    Inventors: Karl H. Schulte-Elte, Roger L. Snowden, Bernard L. Muller
  • Patent number: 4452813
    Abstract: A sulfonate derivative represented by the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxy or halogen, l is an integer of from 0 to 3, n is 0 or 1, A is straight-chain or branched-chain alkylene having 1 to 4 carbon atoms, and R.sub.2 is hydrogen or lower alkyl but, when n is 0 or 1 and A is straight-chain alkylene with 1 to 4 carbon atoms, is not hydrogen and the method for preparing the same.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: June 5, 1984
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Setsuro Fujii, Toshihiro Hamakawa, Kazuo Ogawa, Yoshiyuki Muranaka, Sadao Hashimoto
  • Patent number: 4421934
    Abstract: Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula (I) by the oxy-Cope rearrangement of a diethylenic alcohol of the formula (II), in the presence of a mercuric salt: in formulae (I) and (II), R.sub.1, R.sub.2, R.sub.4, R.sub.5 and R.sub.6, which are identical or different, represent a hydrogen atom or an acyclic hydrocarbon radical and R.sub.3 represents an acyclic hydrocarbon radical, it being understood that R.sub.1 and R.sub.3 can together form a trimethylene radical, or alternatively that R.sub.3 and R.sub.4 can together form an alkylene radical containing 3 to 20 carbon atoms.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: December 20, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Norbert Bluthe, Jacques Gore, Max Malacria
  • Patent number: 4371711
    Abstract: A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atoms, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is a defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula,R.sub.2 MgXwherein R.sub.2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, ##STR5## wherein R.sub.1 and R.sub.
    Type: Grant
    Filed: May 20, 1980
    Date of Patent: February 1, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Hiroshi Yamachika