Aldehyde Reacted With Ketone Patents (Class 568/345)
-
Patent number: 4704478Abstract: 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: GrantFiled: June 25, 1986Date of Patent: November 3, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
-
Patent number: 4701562Abstract: 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: GrantFiled: June 25, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
-
Patent number: 4668827Abstract: 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: GrantFiled: February 4, 1986Date of Patent: May 26, 1987Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Mitsuhiko Tamura, Haruo Katsumata, Kiyoharu Urakawa, Yoshiaki Ohtani
-
Patent number: 4622172Abstract: 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: GrantFiled: December 6, 1985Date of Patent: November 11, 1986Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, William D. Gillaspey, Futoshi Fujioka, Marie R. Hanna
-
Patent number: 4543428Abstract: 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: GrantFiled: June 8, 1984Date of Patent: September 24, 1985Assignee: Oregon Graduate Center for Study & ResearchInventors: Frank M. Hauser, Dipakranjan Mal
-
Patent number: 4528400Abstract: 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: GrantFiled: November 20, 1981Date of Patent: July 9, 1985Assignee: SDS Biotech CorporationInventors: Richard L. Cryberg, Russell M. Bimber
-
Patent number: 4499306Abstract: 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: GrantFiled: March 16, 1983Date of Patent: February 12, 1985Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Naoshi Imaki, Takemi Nakanome
-
Patent number: 4476324Abstract: 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: GrantFiled: June 2, 1982Date of Patent: October 9, 1984Assignee: Union Carbide CorporationInventor: Walter T. Reichle
-
Patent number: 4448712Abstract: 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: GrantFiled: September 13, 1982Date of Patent: May 15, 1984Assignee: Naarden International N.V.Inventors: Antonius J. A. van der Weerdt, Willem Apeldoorn
-
Patent number: 4424378Abstract: 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: GrantFiled: July 8, 1982Date of Patent: January 3, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
-
Patent number: 4413145Abstract: 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: GrantFiled: July 28, 1981Date of Patent: November 1, 1983Assignee: Consiglio Nazionale Delle RicercheInventors: Giovanni Piancatelli, Arrigo Scettri, D'Auria Maurizio
-
Patent number: 4374274Abstract: 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: GrantFiled: September 11, 1980Date of Patent: February 15, 1983Assignee: BASF AktiengesellschaftInventors: Gerd Heilen, Klaus Halbritter, Walter Gramlich
-
Patent number: 4335138Abstract: 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: GrantFiled: September 15, 1980Date of Patent: June 15, 1982Assignee: BASF AktiengesellschaftInventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
-
Patent number: 4334098Abstract: 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: GrantFiled: March 23, 1979Date of Patent: June 8, 1982Assignee: 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: 4315032Abstract: 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: GrantFiled: May 14, 1980Date of Patent: February 9, 1982Assignee: Teitin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
-
Patent number: 4292447Abstract: 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: GrantFiled: December 15, 1978Date of Patent: September 29, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
-
Patent number: 4281204Abstract: 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: GrantFiled: October 5, 1979Date of Patent: July 28, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
-
Patent number: 4244890Abstract: 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: GrantFiled: December 14, 1977Date of Patent: January 13, 1981Assignee: SCM CorporationInventors: Bernard J. Kane, Richard A. Von Genk
-
Patent number: 4234518Abstract: 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: GrantFiled: June 7, 1979Date of Patent: November 18, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, John B. Hall
-
Patent number: 4223168Abstract: 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: GrantFiled: April 24, 1979Date of Patent: September 16, 1980Assignee: 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: 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
-
Patent number: 4217252Abstract: 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: GrantFiled: May 15, 1979Date of Patent: August 12, 1980Assignee: 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: 4210553Abstract: 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: GrantFiled: May 15, 1979Date of Patent: July 1, 1980Assignee: 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: 4210767Abstract: 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: GrantFiled: March 23, 1979Date of Patent: July 1, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt