Preparing Alicyclic Ring Containing Aldehyde By Isomerization Patents (Class 568/443)
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Patent number: 10029970Abstract: The present invention relates to an improved method for producing specific ?, ?-unsaturated aldehydes.Type: GrantFiled: October 15, 2015Date of Patent: July 24, 2018Assignee: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Thomas Netscher, Jan Schuetz, Bettina Wuestenberg
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Patent number: 9908847Abstract: The present invention relates to an improved method for producing specific ?,?-unsaturated aldehydes.Type: GrantFiled: October 15, 2015Date of Patent: March 6, 2018Assignee: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Jan Schuetz, Thomas Netscher, Bettina Wuestenberg
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Publication number: 20120116113Abstract: A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.Type: ApplicationFiled: November 5, 2010Publication date: May 10, 2012Inventors: Mark B. Erman, Joe W. Snow
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Patent number: 7071362Abstract: In the production of an alicyclic aldehyde, a starting aromatic aldehyde is converted into an aromatic acetal for protecting the formyl group. The aromatic ring of the aromatic acetal is then hydrogenated to convert the aromatic acetal into an alicyclic acetal, which is then hydrolyzed to cleave the acetal protecting group to obtain the aimed alicyclic aldehyde.Type: GrantFiled: August 25, 2004Date of Patent: July 4, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomohiro Sugawara, Fumiya Zaima, Atsushi Okoshi, Kinji Kato, Masato Inari
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Patent number: 6700022Abstract: Disclosed is a process for cyclohexyl hydroperoxide (CHHP) decomposition using in aqueous alkaline solution in presence of cobalt catalyst.Type: GrantFiled: June 5, 2002Date of Patent: March 2, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: Ludovic Fodor
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Patent number: 6515186Abstract: A process for obtaining alpha-campholenic aldehyde, which is useful as an aroma chemical and as a synthetic intermediate for other aroma chemicals, particularly those with a sandalwood odor, and also for some pharmaceuticals, is provided. In particular, the invention includes a continuous process for obtaining optically active or racemic &agr;-campholenic aldehyde by a catalytic rearrangement of optically active or racemic &agr;-pinene oxide that can be commercially practicable. In one embodiment, the method comprises continuously feeding &agr;-pinene oxide to a mixture including catalyst(s) and solvent(s), where the solvent(s) have a boiling point higher than the boiling point of &agr;-campholenic aldehyde, under conditions sufficient to provide for the complete, or at least partial, conversion of &agr;-pinene oxide into &agr;-campholenic aldehyde. The process further includes continuously removing &agr;-campholenic aldehyde from the reaction zone by suitable techniques such as distillation.Type: GrantFiled: May 8, 2001Date of Patent: February 4, 2003Assignee: Millennium Specialty ChemicalsInventors: Bernard J. Kane, Gary P. Sanders, Joe W. Snow, Mark B. Erman
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Publication number: 20020169343Abstract: A process for obtaining alpha-campholenic aldehyde, which is useful as an aroma chemical and as a synthetic intermediate for other aroma chemicals, particularly those with a sandalwood odor, and also for some pharmaceuticals, is provided. In particular, the invention includes a continuous process for obtaining optically active or racemic &agr;-campholenic aldehyde by a catalytic rearrangement of optically active or racemic &agr;-pinene oxide that can be commercially practicable.Type: ApplicationFiled: May 8, 2001Publication date: November 14, 2002Inventors: Bernard J. Kane, Gary P. Sanders, Joe W. Snow, Mark B. Erman
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Patent number: 6160182Abstract: Acid catalyzed cyclization of Diels-Alder adducts of myrcene is performed in the presence of hydroxyl-containing compounds, giving the resulting mixtures of isomeric acyloctahydronaphthalenes enhanced quantities of isomers that are particularly useful in perfumery because of their woody-amber odors with enhanced amber note.Type: GrantFiled: August 19, 1998Date of Patent: December 12, 2000Assignee: Millennium Specialty ChemicalsInventors: Mark B. Erman, Carlos G. Cardenas, Henri M. Hoffmann
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Patent number: 6118027Abstract: Unsaturated aldehydes are prepared by mixing propargyl alcohol, a catalyst and a conjugated diolefin and heating the mixture for a time and at a temperature sufficient to form an unsaturated aldehyde. The diolefin may be 2-methylpentadiene, 2(5,5 dimethyl 5 hydroxy pentyl)1,3 butadiene or myrcene. The catalyst may be inorganic, organic, organometallic or mixtures thereof.Type: GrantFiled: April 20, 1999Date of Patent: September 12, 2000Assignee: Givaudan Roure (International) SAInventors: Alan John Chalk, Joseph Anthony Virgilio
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Patent number: 5908957Abstract: A process is disclosed for the catalyzed isomerization of a Z-isomer of a vitamin A compound or of a mixture of several of such isomers into a mixture of the corresponding all-E- and 13-Z-isomers of this vitamin A compound. The process utilizes nitrogen monoxide or a gas mixture containing nitrogen monoxide as the isomerization catalyst. Vitamin A acetate or vitamin A acid is preferably used as the vitamin A compound. The thus-produced all-E vitamin A and its alkanoyl esters have of all isomers by far the highest biological activity and are accordingly almost exclusively used in human and animal nutrition. The 13-Z-vitamin A compounds in turn play an important role as pharmaceutically active substances.Type: GrantFiled: January 26, 1998Date of Patent: June 1, 1999Assignee: Roche Vitamins Inc.Inventor: Angela Wildermann
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Patent number: 5633410Abstract: Disclosed is a process for the preparation of cyclopropanecarboxaldehyde by the isomerization of 2,3-dihydrofuran wherein 2,3-dihydrofuran is contacted with a catalyst selected from alumina, silica-alumina, silica, zirconia, titania and mixtures thereof having a nitrogen BET surface area of about 10 to 350 square meters per gram at elevated temperature.Type: GrantFiled: August 30, 1996Date of Patent: May 27, 1997Assignee: Eastman Chemical CompanyInventors: Shaowo Liang, Timothy W. Price
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Patent number: 5492887Abstract: It was found that 8-exo-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decane having the constitution and stereochemistry of formula (I) possesses particularly useful olfactory properties which are clearly superior to those of the 8-endo-epimer and which already have an effect if compound (I) is enriched with mixtures of 8-exo- and 8-endo-epimers. Compound (I) can therefore be advantageously used, in pure or enriched form, as a scent or as a component of perfume compositions. To prepare an enriched epimer mixture, a mixture obtained in a known manner (U.S. Pat. No. 3,270,061) and having an exo/endo ratio of 1.45:1 is brought into equilibrium by base catalysis, preferably by the action of alkali hydroxides in alcoholic solution, to give an exo/endo ratio of 5.25:1. Alternatively, the enriched epimer mixture can be prepared starting from 8-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decene-3(4), catalytically hydrogenated for example with palladium coal and then optionally brought into equilibrium.Type: GrantFiled: December 11, 1992Date of Patent: February 20, 1996Assignee: Dragoco Gerberding & Co. GmbHInventors: Ernst-Joachim Brunke, Claus-Hermann Kappey, Bernd Holscher, Hartmut Struwe
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Patent number: 5367092Abstract: Described are substituted 2,6-dimethylbicyclo[3,3,1]- non-6-enes defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein "R" represents one of the moieties: ##STR2## processes for preparing same and uses thereof in augmenting or enhancing the aroma 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).Type: GrantFiled: December 17, 1993Date of Patent: November 22, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Charles E. J. Beck, Marie R. Hanna, Franc T. Schiet
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Patent number: 5239108Abstract: A process for producing an aliphatic or alicyclic aldehyde is disclosed, which process comprises the step of hydrogenating an aliphatic or alicyclic carboxylic acid or a derivative thereof with molecular hydrogen in the presence of a catalyst, wherein the catalyst is a zirconium oxide catalyst which contains chromium as an essential component, has a weakly basic site amount of more than 0.03 mmol/g as determined by a temperature programmed desorption method using carbon dioxide as an adsorbate in which the amount of carbon dioxide desorbed in the temperature range of from 100.degree. to 250.degree. C. is measured, and has pores having a radius of from 20 to 500 .ANG. in an amount of not less than 0.1 cc/g and pores having a radius of from 1,000 to 50,000 .ANG. in an amount of not less than 0.05 cc/g as measured with a mercury porosimeter. Aldehydes can be obtained directly from aliphatic or alicyclic carboxylic acids or derivatives thereof in high yield.Type: GrantFiled: October 20, 1992Date of Patent: August 24, 1993Assignee: Mitsubishi Kasei CorporationInventors: Toshiharu Yokoyama, Naoko Matsuyama, Takao Maki
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Patent number: 5081312Abstract: New 4,4,5,8-tetramethyl-1-oxaspiro[2,5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described.4,4,5,8-Tetramethyl-1-oxaspiro[2,5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthesis of valuable fragrance ingredients.Type: GrantFiled: February 20, 1991Date of Patent: January 14, 1992Assignee: Firmenich SAInventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
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Patent number: 5012005Abstract: 4-oxaaldehydes of the formula ##STR1## are prepared by catalytic isomerization of 1,3-dioxanes by a process in which a 1,3-dioxane of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are identical or different and are each hydrogen, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 18 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, aralkyl, aralkenyl or alkenylaryl radical of 5 to 16 carbon atoms or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 and/or R.sup.4 and R.sup.5 together with the carbon atoms to which they are bonded may form a cycloalkane, a cycloalkene or a heterocyclic structure, and the stated radicals may furthermore carry substituents which are inert under the reaction conditions, and R.sup.3 is hydrogen or straight-chain or branched alkyl, is isomerized using a metal oxide catalyst, which has been treated with an acid, and/or a silica phase having a zeolite structure.Type: GrantFiled: July 27, 1989Date of Patent: April 30, 1991Inventors: Wolfgang Hoelderich, Franz Merger
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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: 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: 4939280Abstract: 4-Oxaaldehydes of the formula ##STR1## are prepared by catalytic isomerization of 1,3-dioxanes by a process in which a 1,3-dioxane of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are identical or different and are each hydrogen, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 18 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, aralkyl or alkenylaryl radical of 5 to 16 carbon atoms or a heterocyclic radical, and furthermore R.sup.1 and R.sup.2 and/or R.sup.4 and R.sup.5 together with the carbon atom to which they are bonded may form a cycloalkane, a cycloalkene or a heterocyclic structure, and the stated radicals may furthermore carry substituents which are inert under the reaction conditions, and R.sup.3 is hydrogen or straight-chain or branched alkyl, is isomerized using a phosphate as a catalyst.Type: GrantFiled: April 29, 1988Date of Patent: July 3, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Helmut Lermer
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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: 4745228Abstract: Cyclic ketones of the formula ##STR1## where n is an integer from 4 to 6, are prepared by converting an aliphatic dicarboxylate of the formulaR.sup.1 OCC--(CH.sub.2).sub.n --COOR.sup.2 IIwhere n has the above meaning, R.sup.1 and R.sup.2 are each alkyl, cycloalkyl, aralkyl or aryl and R.sup.2 may furthermore be hydrogen, at from 150.degree. to 450.degree. C. over a solid oxide catalyst.Type: GrantFiled: June 24, 1987Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Martin Decker, Rolf Fischer, Wolfgang Franzischka, Rudolf Kummer, Heinz-Walter Schneider, Uwe Vagt
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Patent number: 4709097Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.Type: GrantFiled: April 14, 1986Date of Patent: November 24, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
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Patent number: 4543429Abstract: 1(7)-p-Methen-9-al, a novel terpene aldehyde, possesses useful organoleptic properties and develops bitter, herbal and aromatic perfume notes. In the field of flavors, 1(7)-p-menthen-9-al develops flowery, herbal and fatty characters reminiscent of certain aspects of the flavor of nuts or cumin.Type: GrantFiled: February 28, 1983Date of Patent: September 24, 1985Assignee: Firmenich SAInventors: Anthony F. Morris, Francois Delay, Fritz Gautschi, Alan F. Thomas, Wolfgang K. Giersch, Andre Boschung
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Patent number: 4477683Abstract: There is provided novel ketones of the structure: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or methyl provided that:R.sub.1 is not the same as R.sub.2 andR.sub.3 is not the same as R.sub.4 ;and fragrance compositions containing them.Type: GrantFiled: May 3, 1982Date of Patent: October 16, 1984Assignee: Givaudan CorporationInventors: Joseph A. Virgilio, Emanuel Heilweil
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Patent number: 4324921Abstract: Ethers of the hydroxypivalaldehyde RCH.sub.2 OCH.sub.2 C(CH.sub.3).sub.2 CHO are prepared by a catalytic isomerization of 5,5-dimethyl-1,3-dioxans at 250.degree. to 500.degree. C. The catalyst is obtained by way of calcination from silicon dioxide, at least one element of the third main group or subgroup in the form of its oxide or hydroxide and at least one alkali metal oxide or hydroxide.Type: GrantFiled: May 29, 1980Date of Patent: April 13, 1982Assignee: Hoechst AktiengesellschaftInventor: Hans-Jurgen Arpe
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4292432Abstract: A process for producing novel aldol derivatives of the formula, ##STR1## wherein C=W is a carbonyl group or a protected carbonyl group which comprises reacting a compound of the formula: ##STR2## wherein C=W is as defined above in the presence of an acid or a base at a temperature ranging from -70.degree. C. to room temperature. The novel aldol derivatives of the above formula are useful as intermediate for producing methanoprostacyclin derivatives which are useful medicines for prevention of thrombosis.Type: GrantFiled: February 4, 1980Date of Patent: September 29, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
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Patent number: 4275238Abstract: Cyclopropylmethyl-N-n-propylamine is prepared by (a) cyclizing 1,4-butanediol by a cobalt-containing catalyst to 2,3-dihydrofuran at a temperature in the range of about 210.degree.-235.degree. C.; (b) thermally isomerizing the 2,3-dihydrofuran to cyclopropanecarboxaldehyde in an open-reactor columm; and (c) reductively alkylating the cyclopropanecarboxaldehyde with n-propylamine and hydrogen in the presence of a platinum catalyst.Type: GrantFiled: January 10, 1980Date of Patent: June 23, 1981Assignee: Ciba-Geigy CorporationInventors: Harris E. Petree, James B. Nabors
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Patent number: 4219451Abstract: Described are perfume compositions and processes for producing same which compositions comprise in an aroma augmenting or enhancing quantity at least one compound having the structure: ##STR1## wherein m is 0 or 1; wherein one of the lines + + + + is a carbon-carbon single bond and the other of the lines + + + + is a carbon-carbon double bond and wherein X is carbinol having the structure: ##STR2## and at least one adjuvant selected from the group consisting of natural perfume oils, synthetic perfume oils, alcohols, aldehydes, ketones other than those defined herein, esters, nitriles and lactones. Also described are colognes containing compounds having the above structure and ethanol and water.Type: GrantFiled: August 3, 1979Date of Patent: August 26, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt