Preparing Alicyclic Ring Containing Aldehyde By Isomerization Patents (Class 568/443)
  • Patent number: 10029970
    Abstract: The present invention relates to an improved method for producing specific ?, ?-unsaturated aldehydes.
    Type: Grant
    Filed: October 15, 2015
    Date of Patent: July 24, 2018
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jan Schuetz, Bettina Wuestenberg
  • Patent number: 9908847
    Abstract: The present invention relates to an improved method for producing specific ?,?-unsaturated aldehydes.
    Type: Grant
    Filed: October 15, 2015
    Date of Patent: March 6, 2018
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Jan Schuetz, Thomas Netscher, Bettina Wuestenberg
  • Publication number: 20120116113
    Abstract: 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: Application
    Filed: November 5, 2010
    Publication date: May 10, 2012
    Inventors: Mark B. Erman, Joe W. Snow
  • Patent number: 7071362
    Abstract: 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: Grant
    Filed: August 25, 2004
    Date of Patent: July 4, 2006
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomohiro Sugawara, Fumiya Zaima, Atsushi Okoshi, Kinji Kato, Masato Inari
  • Patent number: 6700022
    Abstract: Disclosed is a process for cyclohexyl hydroperoxide (CHHP) decomposition using in aqueous alkaline solution in presence of cobalt catalyst.
    Type: Grant
    Filed: June 5, 2002
    Date of Patent: March 2, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ludovic Fodor
  • Patent number: 6515186
    Abstract: 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: Grant
    Filed: May 8, 2001
    Date of Patent: February 4, 2003
    Assignee: Millennium Specialty Chemicals
    Inventors: Bernard J. Kane, Gary P. Sanders, Joe W. Snow, Mark B. Erman
  • Publication number: 20020169343
    Abstract: 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: Application
    Filed: May 8, 2001
    Publication date: November 14, 2002
    Inventors: Bernard J. Kane, Gary P. Sanders, Joe W. Snow, Mark B. Erman
  • Patent number: 6160182
    Abstract: Acid catalyzed cyclization of Diels-Alder adducts of myrcene is performed in the presence of hydroxyl-containing compounds, giving the resulting mixtures of isomeric acyloctahydronaphthalenes enhanced quantities of isomers that are particularly useful in perfumery because of their woody-amber odors with enhanced amber note.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: December 12, 2000
    Assignee: Millennium Specialty Chemicals
    Inventors: Mark B. Erman, Carlos G. Cardenas, Henri M. Hoffmann
  • Patent number: 6118027
    Abstract: 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: Grant
    Filed: April 20, 1999
    Date of Patent: September 12, 2000
    Assignee: Givaudan Roure (International) SA
    Inventors: Alan John Chalk, Joseph Anthony Virgilio
  • Patent number: 5908957
    Abstract: 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: Grant
    Filed: January 26, 1998
    Date of Patent: June 1, 1999
    Assignee: Roche Vitamins Inc.
    Inventor: Angela Wildermann
  • Patent number: 5633410
    Abstract: 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: Grant
    Filed: August 30, 1996
    Date of Patent: May 27, 1997
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Timothy W. Price
  • Patent number: 5492887
    Abstract: 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: Grant
    Filed: December 11, 1992
    Date of Patent: February 20, 1996
    Assignee: Dragoco Gerberding & Co. GmbH
    Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey, Bernd Holscher, Hartmut Struwe
  • Patent number: 5367092
    Abstract: 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: Grant
    Filed: December 17, 1993
    Date of Patent: November 22, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Charles E. J. Beck, Marie R. Hanna, Franc T. Schiet
  • Patent number: 5239108
    Abstract: 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: Grant
    Filed: October 20, 1992
    Date of Patent: August 24, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Toshiharu Yokoyama, Naoko Matsuyama, Takao Maki
  • Patent number: 5081312
    Abstract: 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: Grant
    Filed: February 20, 1991
    Date of Patent: January 14, 1992
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
  • Patent number: 5012005
    Abstract: 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: Grant
    Filed: July 27, 1989
    Date of Patent: April 30, 1991
    Inventors: Wolfgang Hoelderich, Franz Merger
  • 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: 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: 4939280
    Abstract: 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: Grant
    Filed: April 29, 1988
    Date of Patent: July 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Helmut Lermer
  • 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: 4745228
    Abstract: 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: Grant
    Filed: June 24, 1987
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Decker, Rolf Fischer, Wolfgang Franzischka, Rudolf Kummer, Heinz-Walter Schneider, Uwe Vagt
  • Patent number: 4709097
    Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: November 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
  • Patent number: 4543429
    Abstract: 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: Grant
    Filed: February 28, 1983
    Date of Patent: September 24, 1985
    Assignee: Firmenich SA
    Inventors: Anthony F. Morris, Francois Delay, Fritz Gautschi, Alan F. Thomas, Wolfgang K. Giersch, Andre Boschung
  • Patent number: 4477683
    Abstract: 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: Grant
    Filed: May 3, 1982
    Date of Patent: October 16, 1984
    Assignee: Givaudan Corporation
    Inventors: Joseph A. Virgilio, Emanuel Heilweil
  • Patent number: 4324921
    Abstract: 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: Grant
    Filed: May 29, 1980
    Date of Patent: April 13, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Jurgen Arpe
  • Patent number: 4310709
    Abstract: 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: Grant
    Filed: April 23, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventor: Walter Rebafka
  • Patent number: 4292432
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: September 29, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
  • Patent number: 4275238
    Abstract: 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: Grant
    Filed: January 10, 1980
    Date of Patent: June 23, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Harris E. Petree, James B. Nabors
  • Patent number: 4219451
    Abstract: 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: Grant
    Filed: August 3, 1979
    Date of Patent: August 26, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt