Aldehyde Reacted With Ketone Patents (Class 568/345)
  • Patent number: 4704478
    Abstract: Two ketone molecules (which can be the same or different) can be condensed together in the presence of hydrogen to produce a higher ketone by contacting the materials to be condensed with a hydrogenation catalyst and with a non-zeolitic molecular sieve, which has in its calcined form an adsorption of isobutane of at least about 2 percent by weight of the non-zeolitic molecular sieve at a partial pressure of 500 torr and a temperature of 20.degree. C. One or both ketones may be generated in situ by dehydrogenation of an alcohol. The non-zeolitic molecular sieves can achieve improved conversions and selectivities as compared with most conventional catalysts for the reaction.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: November 3, 1987
    Assignee: Union Carbide Corporation
    Inventor: Kurt D. Olson
  • Patent number: 4701562
    Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventor: Kurt D. Olson
  • Patent number: 4668827
    Abstract: The present invention relates to a process for preparing a 2-(1-hydroxyalkyl)cyclohexanone and/or a 2-alkylidene cyclohexanone. According to the present invention, the reaction of cyclohexanone with an aliphatic aldehyde is conducted in a heterogeneous system of an oil-in-water emulsion, whereby it is possible to obtain the 2-(1-hydroxyalkyl)cyclohexanone and/or the 2-alkylidene cyclohexanone in high selectivity.
    Type: Grant
    Filed: February 4, 1986
    Date of Patent: May 26, 1987
    Assignee: Mitsubishi Chemical Industries Ltd.
    Inventors: Mitsuhiko Tamura, Haruo Katsumata, Kiyoharu Urakawa, Yoshiaki Ohtani
  • Patent number: 4622172
    Abstract: Described are alkyl-substituted spiroundecenone derivatives defined according to the structure: ##STR1## wherein R.sub.1 represents isopropyl or hydrogen; R.sub.2, R.sub.3 and R.sub.4 are the same and each represents methyl or hydrogen; with the provisos that:(i) when R.sub.1 is isopropyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen; and(ii) when R.sub.2, R.sub.3 and R.sub.4 are each methyl, R.sub.1 is hydrogen,and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing said alkyl-substituted spiroundecenone derivatives.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: November 11, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, William D. Gillaspey, Futoshi Fujioka, Marie R. Hanna
  • Patent number: 4543428
    Abstract: The compound 6-acetyl-4a,5,6,7,8,8a-hexahydro-1(4H)-naphthalenone, and preparation thereof beginning from 2-(2-hydroxyethyl)bicyclo[2.2.2] oct-5-ene.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: September 24, 1985
    Assignee: Oregon Graduate Center for Study & Research
    Inventors: Frank M. Hauser, Dipakranjan Mal
  • Patent number: 4528400
    Abstract: Disclosed is a method for the preparation of ketones by a catalytic vapor phase reaction of using reactants such as ketones with carboxylic acids and/or carboxylic acid precursors. An example of such a reaction is that of acetone with pivalic acid over a ceria-alumina catalyst at a temperature of nearly 470.degree. C. to produce pinacolone.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: July 9, 1985
    Assignee: SDS Biotech Corporation
    Inventors: Richard L. Cryberg, Russell M. Bimber
  • Patent number: 4499306
    Abstract: A 2,2-dihalo-6-halo-6-(1-haloisobutyl)cyclohexanone represented by the general formula ##STR1## where each of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 is a halogen atom.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: February 12, 1985
    Assignee: Mitsubishi Chemical Industries Ltd.
    Inventors: Naoshi Imaki, Takemi Nakanome
  • Patent number: 4476324
    Abstract: Heat treated anionic clay mineral is an improved catalyst for the conversion of acetone to mesityl oxide and isophorone as well as for the aldol condensation of other carbonyl-containing compounds.
    Type: Grant
    Filed: June 2, 1982
    Date of Patent: October 9, 1984
    Assignee: Union Carbide Corporation
    Inventor: Walter T. Reichle
  • Patent number: 4448712
    Abstract: Perfume compositions, perfumed materials and perfumed articles containing derivatives of spiro [5.5] undecane-3-one and/or undecene-3-one having the following formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or methyl and the dotted line is a single or double bond with the proviso that when this dotted line is a double bond R.sub.1 and R.sub.2 are both hydrogen.The use of one or more derivatives of spiro [5.5] undecane-3-one and/or -undecene-3-one having formula 1 as a perfume component in perfume compositions and in imparting fragrance to materials and articles for example soaps, cleaning preparations and cosmetic preparations.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: May 15, 1984
    Assignee: Naarden International N.V.
    Inventors: Antonius J. A. van der Weerdt, Willem Apeldoorn
  • Patent number: 4424378
    Abstract: Described are methyl substituted pinyl oxopentenes and mixtures of same and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, perfumed articles (including perfumed polymers, solid or liquid cationic, anionic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, optical brightener compositions, and cosmetic powders), colognes, smoking tobacco compositions and smoking tobacco articles including cigars, cigarettes and integrated and separated filters therefor.
    Type: Grant
    Filed: July 8, 1982
    Date of Patent: January 3, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
  • Patent number: 4413145
    Abstract: Process for the synthesis of the 3-keto-cyclopentene-5-oxy derivatives (rethrolones) having the general formula: ##STR1## wherein: R.sub.1 is hydrogen, saturated or unsaturated C.sub.1 -C.sub.10 alkyl.R.sub.2 is saturated or unsaturated C.sub.1 -C.sub.10 alkyl.R.sub.3 is hydrogen or benzoyl characterized as having insecticide activity.The process comprises as a basic operation the photoisomerization of a transenedicarbonylic intermediate to the corresponding cis form and then its cyclization to a rethrolone.
    Type: Grant
    Filed: July 28, 1981
    Date of Patent: November 1, 1983
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Giovanni Piancatelli, Arrigo Scettri, D'Auria Maurizio
  • Patent number: 4374274
    Abstract: A process for the preparation of .alpha.-methylsubstituted ketones by reacting the corresponding non-methylsubstituted ketones with formaldehyde under hydrogenating conditions. The reaction proceeds easily and with good yields if a catalyst containing metallic palladium deposited on a zirconium, hafnium, titanium or tin phosphate is used. The products are valuable intermediates for the preparation of dyes, crop protection agents or drugs.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: February 15, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Heilen, Klaus Halbritter, Walter Gramlich
  • Patent number: 4335138
    Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.
    Type: Grant
    Filed: September 15, 1980
    Date of Patent: June 15, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
  • Patent number: 4334098
    Abstract: Described is the compound trans, trans-.DELTA.-damascone and mixtures of trans, trans-.DELTA.-damascone and its isomer, cis, trans-.DELTA.-damascone is in a major proportion, a process for preparing same and processes for adding such trans, trans-.DELTA.-damascone or such mixtures containing high proportions of trans, trans-.DELTA.
    Type: Grant
    Filed: March 23, 1979
    Date of Patent: June 8, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Richard A. Wilson, Frederick L. Schmitt, Manfred H. Vock, Edward J. Granda, Joaquin Vinals, Jacob Kiwala, William L. Schreiber
  • Patent number: 4315032
    Abstract: A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.
    Type: Grant
    Filed: May 14, 1980
    Date of Patent: February 9, 1982
    Assignee: Teitin Limited
    Inventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
  • Patent number: 4292447
    Abstract: Described is a process for preparing hydrogenated derivatives of 2,6,6-trimethyl cyclohexene derivatives by means of treating said derivatives with hydrogen in the presence of a supported palladium catalyst such as palladium-on-calcium carbonate or palladium-on-barium sulfate in the presence of a quinoline activator. The resulting products are useful for their organoleptic properties as foodstuff flavorants and flavor enhancers, perfume composition ingredients, perfumed article ingredients and tobacco flavorants and flavor enhancers.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: September 29, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4281204
    Abstract: The present invention relates to substituted spirocyclic derivatives having the general formula: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond, wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are each the same or different, hydrogen or lower alkyl, wherein Z is one of the following: ##STR2## wherein R.sub.7 is either hydrogen or lower alkyl, wherein R.sub.8 and R.sub.9 are each lower alkyl; their methods of preparation and their use as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in the flavoring of foodstuffs and tobacco products.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: July 28, 1981
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman
  • Patent number: 4244890
    Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.CROSS REFERENCE TO RELATED APPLICATIONSThis application is related to applicant's commonly owned copending application Ser. No. 916,966 filed 19 June 1978, now U.S. Pat. No. 4,179,468 dated 18 Dec. 1979 and entitled Cyclic Terpenoid Onium Salts, Their Preparation and Uses.
    Type: Grant
    Filed: December 14, 1977
    Date of Patent: January 13, 1981
    Assignee: SCM Corporation
    Inventors: Bernard J. Kane, Richard A. Von Genk
  • Patent number: 4234518
    Abstract: Described is a process for the production of alpha, beta unsaturated ketones by reaction of an aldehyde with a ketone in the presence of a catalyst consisting essentially of either zinc acetate or zinc acetate dihydrate. The ketones obtained are suitable and some cases as solvents and in some cases as intermediates for the production of valuable odorants, dyes, plastics and especially nature-identical substances and are also useful as odorants per se.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: November 18, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, John B. Hall
  • Patent number: 4223168
    Abstract: Processes and compositions are described for the use in perfume aroma augmenting, enhancing, modifying and imparting compositions and as perfume and perfumed article aroma imparting and enhancing materials of oxyhydrocarbylnorbornanes having the structure: ##STR1## wherein X is carbonyl or carbinyl having the structures, respectively: ##STR2## and wherein at least one of the dashed lines is a carbon-carbon single bond and the other of the dashed lines is a carbon-carbon single bond or a carbon-carbon double bond. Addition of the said oxyhydrocarbylnorbornanes to consumable materials is indicated to produce in perfumes, colognes and perfumed articles, natural, sweet pine, incense, camphene-like, sweet, green, floral, fruity, dried fruity, ionone-like, orris-like and nasturtium-like aromas with dried, woody, piney, sweaty, geranic acid-like nuances.
    Type: Grant
    Filed: April 24, 1979
    Date of Patent: September 16, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, James M. Sanders, Manfred H. Vock, Edward J. Shuster, Joaquin Vinals, William L. Schreiber, John B. Hall, Denis E. Hruza, Sr., Venkatesh Kamath, Braja D. Mookherjee, Ching Y. Tseng, Mark A. Sprecker
  • 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
  • Patent number: 4217252
    Abstract: Described is a process for augmenting or enhancing the aroma of a perfume composition as well as perfume and cologne compositions containing a mixture consisting essentially of compounds having the structures: ##STR1## and wherein the mixture contains 30% of the compounds having the structures; ##STR2## and 60% of the compound having the structure: ##STR3##
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: August 12, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
  • Patent number: 4210553
    Abstract: Described is a process for augmenting or enhancing the aroma of solid or liquid anionic, cationic or nonionic detergent compositions comprising adding to a solid or liquid anionic, cationic or nonionic detergent base, an aroma augmenting or enhancing quantity of at least one of the compounds having a structure: ##STR1## whereby sweet, floral, fruity, rose-like, minty/camphoraceous aromas with floral, hay-like, musty backgrounds and tobacco nuances are augmented, enhanced or imparted.
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: July 1, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
  • Patent number: 4210767
    Abstract: Described are perfume and fragrance compositions and perfumed articles including soaps, detergents, powders as well as colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones having the generic structure: ##STR1## wherein one of the lines + + + + + is a carbon-carbon double bond and the other of the lines + + + + + is a carbon-carbon single bond; wherein X is carbinol having the structure: ##STR2## or carbonyl having the structure ##STR3## wherein A' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; wherein B' is hydrogen,CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; where n is 0, 1 or 2; wherein each of the dashed lines are the same and each represents a carbon-carbon single bond or no bond; wherein A' and B' are both --CH.sub.2 -- when n is 1 or 2 and the dashed line is a carbon-carbon single bond or A' is hydrogen and B' is C.sub.2 H.sub.5 or CH.sub.3 or both A' and B' are each CH.sub.3 or A' is C.sub.2 H.sub.
    Type: Grant
    Filed: March 23, 1979
    Date of Patent: July 1, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt