Gaseous Hydrogen Reactant Or Group Ia Or Iia Light Metal Containing Material Utilized Patents (Class 568/350)
  • Patent number: 5081311
    Abstract: Muscone of the formula I ##STR1## is prepared by a process in which an open-chain 2,15-diketone of the general formula IICH.sub.3 --CO--X--CO--CH.sub.3 (II)where X is one of the radicals--(--CH.sub.2 --).sub.12 -- (a)--CH.dbd.CH--(--CH.sub.2 --).sub.8 --CH.dbd.CH-- (b)--CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.6 --CH.dbd.CH--CH.sub.2 --(c)--CH.sub.2 --CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.4 --CH.dbd.CH--CH.sub.2 --CH.sub.2 -- (d) or--CH.sub.2 --CH.sub.2 CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --CH.sub.2 -- (e)is brought into contact, at from 300.degree. to 400.degree. C. in the presence of from 5 to 15% by weight, based on the amount of catalyst, of water, in the gas phase, with a fixed-bed catalyst containing TiO.sub.2, CeO.sub.2 or the ThO.sub.2 as the catalytically active compound and the unsaturated cyclic ketone formed by intramolecular aldol condensation is subjected to catalytic hydrogenation.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: January 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Thomas Kuekenhoehner, Karl Brenner, Rainer Becker, Matthias Irgang, Charles Schommer
  • Patent number: 4940819
    Abstract: The catalytic hydrogenation of .alpha.,.beta.-unsaturated ketones of the formulaR.sup.1 --CH.dbd.CH--CO--R.sup.2,in whichR.sup.1 and R.sup.2 independently of one another represent straight-chain or branched alkyl, hydroxy-alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl or aryl, where at least one of the radicals R.sup.1 and R.sup.2 is monosubstituted to trisubstituted by halogen,can be carried out on a Ni-containing catalyst and in the presence of an organic sulphur compound of the formulaR.sup.3 --S(.dbd.O).sub.n --R.sup.4in whichR.sup.3 and R.sup.4 independently of one another denote straight-chain or branched alkyl, hydroxy-alkyl, carboxyalkyl or phenyl, and furthermoreR.sup.3 and R.sup.4 may together represent --CH.dbd.CH--CH.dbd.CH--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --,R.sup.4 may additionally denote hydrogen or CO--C.sub.1 -C.sub.12 -alkyl and n assumes the value 0 or 1.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: July 10, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kiel, Heinz Ziemann
  • Patent number: 4918240
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: April 17, 1990
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Guzinski
  • Patent number: 4820874
    Abstract: The yield of 2,5,6-trimethyl-cyclohex-2-en-1-one is increased by reacting diethyl ketyone, in the presence of an alkali, with crotonaldehyde or a compound which is converted to crotonaldehyde under the reaction conditions chose, and working up the reaction mixture by distillation, by a method in which the distillation residue obtained is either(a) heated at from 120.degree. to 250.degree. C. in particular from 120.degree. to 200.degree. C., with the addition of a catalytic amount of an alkali, or(b) heated at from 150.degree. to 250.degree. C. without the addition of such a substance,and the mixture of 2,5,6-trimethylcyclohex-2-en-1-one and diethyl ketone which is formed from the distillation residue as a result of the heat treatment is separated by distillation.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: April 11, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Tavs, Harald Laas, Horst Schauer, Lothar Arnold
  • Patent number: 4788342
    Abstract: 4,4,8,8,10-pentamethylbicyclo[4,4,0]-decene-(1,6)-one(2), is produced from the bottom product of the acetone condensation reaction collecting in the production of isophorone by fractionation. A ketone blend consisting essentially of C.sub.15 compounds where the main components are isomers [B] and [C] as shown in the general formulas: ##STR1## is isolated. This ketone blend is selectively hydrated in the presence of a noble metal catalyst at hydrogen pressures of 20 to 250 mbars and at temperatures between 25.degree. and 150.degree. C. The 4,4,8,8,10-pentamethylbicyclo[4,4,0]-decene-(1,6)-one(2) is obtained by rectifying the hydration output.
    Type: Grant
    Filed: August 14, 1987
    Date of Patent: November 29, 1988
    Assignee: Huls Aktiengesellschaft
    Inventor: Wilfried Buschken
  • 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: 4501918
    Abstract: Described is a product-by-process which comprises:(A) an aldol condensation between isobutyraldehyde and acetone in the presence of a base.(B) cyclic dimerization of the product.(C) reduction of the resultant product.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: February 26, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Philip T. Klemarczyk
  • Patent number: 4484005
    Abstract: Disclosed is a process for the preparation of cyclohexyl cyclohexanone (CHA). Cyclohexanone is self-condensed to yield a mixture of cyclohexylidene cyclohexanone (CHDA), water, and unconverted cyclohexanone. The CHDA in the mixture is directly hydrogenated to CHA under an atmosphere of hydrogen and in the presence of a suitable catalyst, the presence of water and cyclohexanone not affecting the reaction. The CHA may be separated from the other components by, for example, fractional distillation following the hydrogenation.
    Type: Grant
    Filed: February 14, 1983
    Date of Patent: November 20, 1984
    Assignee: Stamicarbon B.V.
    Inventor: Petrus J. H. Thomissen
  • Patent number: 4471135
    Abstract: Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: September 11, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Braja D. Mookherjee, Anton Van Ouwerkerk, Augustinus G. Van Loveren
  • Patent number: 4401823
    Abstract: Polyhydroxylated compounds such as glucose, sucrose, sorbitol, etc. are subjected to a hydrogenolysis reaction at hydrogenolysis conditions which include a temperature in the range of from about 175.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 2000 pounds per square inch in the presence of a catalytic composition of matter. The catalyst comprises a carbonaceous pyropolymer possessing recurring units containing at least carbon and hydrogen atoms which is impregnated with a transition metal. The products which are obtained will include alcohols, acids, ketones, ethers, and hydrocarbons.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: August 30, 1983
    Assignee: UOP Inc.
    Inventor: Blaise J. Arena
  • Patent number: 4393245
    Abstract: New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: July 12, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Hoffman, Karl von Fraunberg, Manfred Baumann
  • Patent number: 4339606
    Abstract: Ketones are converted in one step to saturated dimeric ketones by passing them over a zeolite having a silica to alumina ratio of at least 12 and a Constraint Index of from 1 to 12 and containing a Group VIII metal.
    Type: Grant
    Filed: February 6, 1981
    Date of Patent: July 13, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Tracy J. Huang, Werner O. Haag
  • Patent number: 4331814
    Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.
    Type: Grant
    Filed: February 1, 1973
    Date of Patent: May 25, 1982
    Assignee: Rhone Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4302607
    Abstract: New unsaturated macrocyclic ketones are obtained via a process which consists in reacting a dialdehyde with a tetraalkyldiphosphonate ester. The new ketones are useful intermediates for the preparation of cyclopentadecanone and its higher methyl-homologue, known fragrant substances. New ketones possess also direct utility as musky odorants.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: November 24, 1981
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • 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: 4273944
    Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4263014
    Abstract: Anti-rust motor fuel composition comprising a major proportion of a mixture of hydrocarbons boiling in the gasoline boiling range, a minor amount of a polymeric acid comprising a dimer or trimer of a dienoic or trienoic acid containing from 16 to 18 carbon atoms and a minor amount of an aminoalkyl or polyalkyl polyamine imidazoline derivative of a hydrocarbon-substituted gamma or delta lactone reaction product.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: April 21, 1981
    Assignee: Texaco Inc.
    Inventors: Marshall E. Davis, Kenneth L. Dille
  • Patent number: 4258268
    Abstract: At least one of a polycyclic phenol, a polycyclic alcohol and a polycyclic ketone is produced under hydrogenation conditions using a nickel oxide/manganese oxide/magnesium oxide catalyst by subjecting at least one of a monocyclic ketone, a monocyclic alcohol and a monocyclic phenol to said conditions and said catalyst.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: March 24, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Geir Bjornson
  • Patent number: 4250332
    Abstract: Described is a process for preparing .beta.-damascone starting with 2,6,6-trimethyl cyclohex-2-enone according to the reaction sequence: ##STR1## wherein Z is hydrogen, MgX', Li, Na or K; Y is MgX', Li, Na or K; X' is Cl, Br or I; R is C.sub.1 -C.sub.3 lower alkyl such as methyl, ethyl, n-propyl or i-propyl; X is Cl, Br or I. Also described are the organoleptic uses of the compound having the structure: ##STR2## in augmenting or enhancing the taste or aroma of a consumable material, e.g., foodstuff, chewing gum, medicinal product, chewing tobacco, smoking tobacco, perfume, perfumed article (e.g., drier-added fabric softener articles and solid or liquid anionic, cationic or nonionic detergents) and cologne.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: February 10, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, John B. Hall, Robin Kasper, Manfred H. Vock, Ronald Schreck, Edward J. Granda, Joaquin F. Vinals
  • 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: 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: 4204073
    Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: May 20, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Frank Kienzle