Isomerization Patents (Class 568/341)
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Patent number: 6388140Abstract: 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: GrantFiled: February 15, 2001Date of Patent: May 14, 2002Assignee: Ube Industries, Ltd.Inventors: Ryoji Sugise, Shuji Tanaka, Kohichi Kashiwagi, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
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Publication number: 20020055453Abstract: 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: ApplicationFiled: August 2, 2001Publication date: May 9, 2002Inventors: Marcus Eh, Ingo Wohrle
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Patent number: 6329535Abstract: 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: GrantFiled: October 20, 2000Date of Patent: December 11, 2001Assignee: Degussa Dental GmbH & Co. KGInventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
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Publication number: 20010049455Abstract: 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: ApplicationFiled: March 13, 2001Publication date: December 6, 2001Applicant: Kao CorporationInventors: Takahiro Asada, Yoshiharu Ataka, Junji Koshino
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Publication number: 20010023071Abstract: 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: ApplicationFiled: February 15, 2001Publication date: September 20, 2001Applicant: Ube Industries, Ltd.Inventors: Ryoji Sugise, Shuji Tanaka, Kohichi Kashiwagi, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
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Patent number: 6274771Abstract: 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: GrantFiled: June 22, 2000Date of Patent: August 14, 2001Assignee: AtofinaInventors: Francois Mongenet, Rémy Teissier
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Patent number: 6274772Abstract: 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: GrantFiled: June 22, 2000Date of Patent: August 14, 2001Assignee: AtofinaInventors: Rémy Teissier, Georges Martino-Gauchi
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Patent number: 6265617Abstract: 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: GrantFiled: May 13, 1999Date of Patent: July 24, 2001Assignee: Degussa-Huls AktiengesellschaftInventors: Steffen Krill, Stephan Kretz, Hans-Joachim Hasselbach, Klaus Huthmacher, Rainer Hahn, Hermann Schmitt
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Patent number: 6198004Abstract: 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: GrantFiled: June 10, 1999Date of Patent: March 6, 2001Assignee: Haas Hop Products, Inc.Inventors: John Paul Maye, Jianping Xu, George Gauthier, Scott W. Weis
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Patent number: 6005147Abstract: 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: GrantFiled: September 26, 1997Date of Patent: December 21, 1999Assignee: Degussa AktiengesellschaftInventors: Steffen Krill, Gunes Giray, Klaus Huthmacher, Frank Hubner, Herbert Tanner
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Patent number: 5917093Abstract: 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: GrantFiled: November 13, 1997Date of Patent: June 29, 1999Assignee: Miller Brewing CompanyInventors: Patrick L. Ting, Jay R. Refling, Michael A. VanSanford, Henry Goldstein
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Patent number: 5908956Abstract: 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: GrantFiled: December 17, 1997Date of Patent: June 1, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Ikuo Takahashi, Masahiro Chikamori
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Patent number: 5907065Abstract: 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: GrantFiled: September 26, 1997Date of Patent: May 25, 1999Assignee: Degussa AktiengesellschaftInventors: Steffen Krill, Gunes Giray, Frank Hubner, Rainer Hahn, Klaus Huthmacher, Herbert Tanner
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Patent number: 5886231Abstract: 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: GrantFiled: June 24, 1997Date of Patent: March 23, 1999Assignee: Zeneca LimitedInventors: Stephen Martin Brown, Howard Rawlinson
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Patent number: 5576462Abstract: 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: GrantFiled: August 3, 1995Date of Patent: November 19, 1996Assignee: BASF AktiengesellschaftInventors: Norbert Rieber, Joaquim H. Teles
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Patent number: 5334768Abstract: 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: GrantFiled: February 3, 1993Date of Patent: August 2, 1994Assignee: DSM N.V.Inventors: Johannes G. van Hinsberg, Cornelis G. M. van de Moesdijk, Ivo Spaargaren, Otto E. Sielcken
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Patent number: 5321164Abstract: 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: GrantFiled: October 27, 1993Date of Patent: June 14, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William J. Fylak, Joseph A. Mc Ghie, Charles E. J. Beck
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Patent number: 5296637Abstract: 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: GrantFiled: December 31, 1992Date of Patent: March 22, 1994Assignee: Kalamazoo Holdings, Inc.Inventors: Larry J. Stegink, James A. Guzinski, Paul H . Todd, Jr.
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Patent number: 5276197Abstract: 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: GrantFiled: September 11, 1992Date of Patent: January 4, 1994Assignee: Hoffman-La Roche Inc.Inventors: Paul Nosberger, Adrian J. Vieth
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Patent number: 5235110Abstract: 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: GrantFiled: March 20, 1992Date of Patent: August 10, 1993Assignee: Nippon Zeon Co., Ltd.Inventors: Toshiro Yamada, Hiroshi Fujisawa, Hideyuki Tanaka
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Patent number: 5185470Abstract: 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: GrantFiled: February 5, 1992Date of Patent: February 9, 1993Assignee: Kuraray Company, Ltd.Inventors: Goro Asanuma, Yoshin Tamai
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Patent number: 5166447Abstract: 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: GrantFiled: October 15, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Tom Witzel
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Patent number: 5155276Abstract: 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: GrantFiled: September 9, 1991Date of Patent: October 13, 1992Assignee: Hopstabil Hopfenverarbeitungs GmbHInventor: Herbert Paul
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Patent number: 5113021Abstract: 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: GrantFiled: September 6, 1990Date of Patent: May 12, 1992Assignee: Givaudan CorporationInventors: Georg Frater, Daniel Helmlinger
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Patent number: 5041678Abstract: 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: GrantFiled: September 28, 1990Date of Patent: August 20, 1991Assignee: Firmenich S.A.Inventors: Charles Fehr, Jose Galindo
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Patent number: 5019297Abstract: 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: GrantFiled: April 18, 1989Date of Patent: May 28, 1991Assignee: Henkel Research CorporationInventor: Michael J. Virnig
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Patent number: 4980511Abstract: Aldehydes and ketones are prepared from epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each alkyl, alkenyl, aryl, alkoxy or aralkyl and R.sup.3 has the same meanings or is hydrogen, by a catalytic rearrangement reaction in the presence of various catalysts, in particular zeolites of the pentasil type.Type: GrantFiled: September 25, 1987Date of Patent: December 25, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Helmut Lermer
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Patent number: 4970345Abstract: 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: GrantFiled: February 20, 1986Date of Patent: November 13, 1990Assignee: Sumitomo Chemical Company, LimitedInventor: Masayoshi Minai
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Patent number: 4950797Abstract: 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: GrantFiled: June 1, 1988Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
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Patent number: 4918240Abstract: 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: GrantFiled: August 15, 1988Date of Patent: April 17, 1990Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Guzinski
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Patent number: 4885397Abstract: 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: GrantFiled: September 14, 1988Date of Patent: December 5, 1989Assignee: Huels AktiengesellschaftInventor: Wilfried Bueschken
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Patent number: 4845303Abstract: 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: GrantFiled: August 24, 1988Date of Patent: July 4, 1989Assignee: Huels AktiengesellschaftInventor: Hans Bellut
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Patent number: 4794193Abstract: 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: GrantFiled: April 15, 1982Date of Patent: December 27, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
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Patent number: 4749814Abstract: Ethylenic carbonyl compounds of formula ##STR1## are made by the isomerization of acetylenic alcohols of formula ##STR2## in the presence of a catalyst consisting of a titanium derivative, a copper or silver derivative, and, if required, an acid, which may be in the form of an ester or anhydride, or an inorganic ester.Type: GrantFiled: April 2, 1987Date of Patent: June 7, 1988Assignee: Rhone-Poulenc SanteInventor: Pierre Chabardes
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Patent number: 4734529Abstract: 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: GrantFiled: December 22, 1986Date of Patent: March 29, 1988Assignee: Degussa AktiengesellschaftInventors: Marion Berg, Andreas Grund, Guenter Prescher
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Patent number: 4695673Abstract: 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: GrantFiled: June 9, 1986Date of Patent: September 22, 1987Assignee: Stauffer Chemical CompanyInventors: James B. Heather, Pamela D. Milano
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Patent number: 4694107Abstract: Ketones are prepared by isomerization of aldehydes at elevated temperatures over zeolites.Type: GrantFiled: July 2, 1986Date of Patent: September 15, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Rolf Fischer
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Patent number: 4673759Abstract: 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: GrantFiled: March 3, 1986Date of Patent: June 16, 1987Assignee: Montedison S.p.A.Inventor: Enrico Dalcanale
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Patent number: 4644084Abstract: 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: GrantFiled: February 3, 1986Date of Patent: February 17, 1987Assignee: Miller Brewing CompanyInventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
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Patent number: 4590296Abstract: 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: GrantFiled: January 25, 1984Date of Patent: May 20, 1986Assignee: Miller Brewing CompanyInventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
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Preparation of compounds of the 4-oxodamascone series, and novel scents from this class of compounds
Patent number: 4550211Abstract: 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: GrantFiled: March 12, 1984Date of Patent: October 29, 1985Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann -
Patent number: 4540797Abstract: 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: GrantFiled: December 6, 1982Date of Patent: September 10, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4540825Abstract: 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: GrantFiled: April 2, 1984Date of Patent: September 10, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Katsuyuki Shiota, Kunihiko Tanaka, Masayoshi Minai
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Patent number: 4537995Abstract: 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: GrantFiled: November 7, 1983Date of Patent: August 27, 1985Assignee: Celanese CorporationInventors: H. Clay Linstid, III, Gerald S. Koermer
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Patent number: 4532358Abstract: 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: GrantFiled: August 10, 1984Date of Patent: July 30, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4510329Abstract: 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: GrantFiled: November 28, 1980Date of Patent: April 9, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4460792Abstract: 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: GrantFiled: August 19, 1982Date of Patent: July 17, 1984Assignee: Firmenich S.A.Inventors: Karl H. Schulte-Elte, Roger L. Snowden, Bernard L. Muller
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Patent number: 4452813Abstract: 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: GrantFiled: May 11, 1982Date of Patent: June 5, 1984Assignee: Taiho Pharmaceutical Company LimitedInventors: Setsuro Fujii, Toshihiro Hamakawa, Kazuo Ogawa, Yoshiyuki Muranaka, Sadao Hashimoto
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Patent number: 4421934Abstract: 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: GrantFiled: March 5, 1982Date of Patent: December 20, 1983Assignee: Rhone-Poulenc SanteInventors: Norbert Bluthe, Jacques Gore, Max Malacria
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Patent number: 4371711Abstract: 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: GrantFiled: May 20, 1980Date of Patent: February 1, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika