Unsaturated Alicyclic Ring Containing Patents (Class 568/667)
  • Patent number: 5731283
    Abstract: Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: March 24, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
  • Patent number: 5698136
    Abstract: A novel liquid crystalline compound having a high elastic constant ratio, K.sub.33 /K.sub.11, a superior compatibility with other liquid crystal compounds, particularly a low temperature compatibility therewith, and chemical stability; a liquid crystal composition containing such a liquid crystalline compound; and a liquid crystal display element, are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R.sub.1 is an alkyl group or an alkyloxy group of 1 to 10C or a halogenated alkyl group, a halogenated alkyloxy group of 1 to 4C, halogen atom or cyano group; R.sub.2 is H atom or an alkyl group of 1 to 3C; rings A and B each independently are 1,4-phenylene ring or trans-1,4-cyclohexylene group, which may be substituted by halogen atom; Z is single bond, 1,4-phenylene ring, trans-1,4-cyclohexylene ring or 1,2-ethylene group; p is 2 to 4; and q is 0 or 1.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: December 16, 1997
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Shuichi Matsui, Norihisa Hachiya, Etsuo Nakagawa
  • Patent number: 5672779
    Abstract: The present invention provides a compound represented by the formula: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group or a C.sub.1 -C.sub.6 alkyl group which may be substituted with at least one halogen atom; and A' represents a hydrogen atom or a protecting group for a hydroxyl group. The compound is useful in the preparation of esters which can be used to control insect pests.
    Type: Grant
    Filed: May 1, 1996
    Date of Patent: September 30, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
  • Patent number: 5629454
    Abstract: Conformationally locked 4',6'-cyclopropane-fused carbocyclic nucleoside analogues. The compounds are prepared by condensing a cyclopropane-fused carbocyclic allylic alcohol with substituted purine or pyrimidine bases. The condensation products are then modified to produce the adenosine, guanosine, cytidine, thymidine and uracil nucleoside analogues. The compounds are therapeutically useful as antimetabolites, or in the preparation of anti-metabolic agents.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: May 13, 1997
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Victor E. Marquez, Juan B. Rodriguez, Marc C. Nicklaus, Joseph J. Barchi, Jr., Maqbool A. Siddiqui
  • Patent number: 5552434
    Abstract: Compounds of the formula ##STR1## where the dotted line represents a bond or the absence of a bond, the wavy lines represent bonds which are either in cis or trans configuration; R.sub.1 represents H, or CO--R.sub.2 where R.sub.2 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group; X represents CO--NR.sub.3 R.sub.4, CH.sub.2 OH, CH.sub.2 OR.sub.5, CH.sub.2 O--COR.sub.6, and CH.sub.2 --NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 independently are H or lower alkyl, R.sub.5 is lower alkyl of 1 to 6 carbons, and R.sub.6 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group, and n is an integer between 0 and 8 are capable of lowering intraocular pressure in the eye of a mammal.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: September 3, 1996
    Assignee: Allergan
    Inventors: Michael E. Garst, Robert M. Burk
  • Patent number: 5405948
    Abstract: A compound of formula (I): selected from 1,5-diyne-3-cyclodecene and undecene compounds. ##STR1## in which: R represents a hydrogen atom, a straight-chain or branched (C.sub.1 -C.sub.6) acyl radical or a glycoside radical,R' represents a hydrogen atom ##STR2## n is 1 or 2, and R.sub.1 and R.sub.2 simultaneously represent two hydrogen atoms or, together with the two carbon atoms and the double bond to which they are attached, form a phenyl ring.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: April 11, 1995
    Assignee: Adir et Compagnie
    Inventors: Jean-Marie Beau, Christophe Crevisy, Ghanem Atassi, Alain Pierre
  • Patent number: 5362916
    Abstract: Hydroxyaryl enol ether alkali metal salts having the formula: ##STR1## in which T is a fused, substituted or unsubstituted polycycloalkylidene group, OR.sup.3 is an ether group Y is a light-emitting fluorophore-forming group which will be part of a luminescent substance formed by decomposition of a 1,2-dioxetane subsequently formed from the hydroxyaryl enol ether alkali metal salt, capable of absorbing energy to form an excited state from which it emits optically detectable energy to return to its ground state, and AM.sup.30 is an alkali metal cation, processes for the preparation of these intermediate salts, and their use as starting materials for acylation, phosphorylation and glycosylation reactions to give intermediates reactable to give stable, water-soluble chemiluminescent 1,2-dioketames, particularly ones that are enzymatically cleavable, are disclosed.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: November 8, 1994
  • Patent number: 5321164
    Abstract: Described is the 2(1-vinyl-5-hexenyl)cyclopentanone having the structure: ##STR1## a process for preparing same by reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## and then heating the resulting intermediate, and organoleptic uses of the compound having the structure: ##STR4## in perfumery.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: June 14, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William J. Fylak, Joseph A. Mc Ghie, Charles E. J. Beck
  • Patent number: 5313002
    Abstract: The invention relates to novel ethers and their use as aroma precursors. The ethers are derived from ionol and related compounds. These aroma precursors do not have a substantial aroma as such under ambient conditions, but will break up into a complex mixture having useful organoleptic properties under heating. The ethers are especially suitable for use in products which are heated, burned or smouldered in some stage of their use. The compounds according to the invention are especially suitable for application to tobacco. Mixtures obtained by degrading (e.g. by heating) the ethers according to the invention may be used in a flavouring or perfuming mixture as well due to their organoleptic properties.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: May 17, 1994
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Johannes T. De Heij, Franciscus P. Van Lier, Harrie Renes
  • Patent number: 5288428
    Abstract: Compounds having a terminal alkyloxypropenyl group of the general formula ##STR1## wherein rings A.sup.1 and A.sup.2 each independently represent unsubstituted or halogen-substituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen, or trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; n is either 0 or 1; Z.sup.1 and Z.sup.2 each independently signify a single covalent bond or --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O--, the trans form of --O--CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 --O--, --(CH.sub.2).sub.2 CH.dbd.CH-- or --CH.dbd.CH--(CH.sub.2).sub.2 --; R.sup.1 denotes an alkyl group; R.sup.2 represents halogen, cyano, trifluoroacetyl, optionally fluorine-substituted alkyl with 1 to 12 carbon atoms, in which optionally 1 --CH.sub.2 -- group or 2 non-adjacent --CH.sub.2 -- groups is/are replaced by oxygen and/or a --CH.sub.2 CH.sub.
    Type: Grant
    Filed: August 6, 1991
    Date of Patent: February 22, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Stephen Kelly
  • Patent number: 5243094
    Abstract: Derivatives of long-chain fatty alcohols, and methods of obtaining them, are provided, as well as pharmaceutical compositions containing derivatives and their uses, in particular in treating or preventing neuro-degenerative illnesses, conditions linked to skin ageing, the phenomena of thrombosis and atherosclerosis, and immune deficiencies.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: September 7, 1993
    Assignee: Medafor
    Inventor: Jacques Borg
  • Patent number: 5243080
    Abstract: The present invention provides a novel compound represented as ##STR1## The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: September 7, 1993
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
  • Patent number: 5227507
    Abstract: A process for the manufacture of compounds of the general formula ##STR1## wherein R.sup.1 signifies hydroxy or an etherified hydroxy group, and of zeaxanthin by converting a compound of the general formula ##STR2## wherein R.sup.1 has the above significance, in an inert organic solvent into the acetylenide and reacting this with methyl vinyl ketone, reducing the alcoholate obtained or the alcohol (obtained after hydrolysis of the alcoholate) of the general formula ##STR3## wherein R.sup.1 has the above significance, in an inert organic solvent with an aluminum hydride of the general formulaR.sub.x MAlH.sub.4-x IIIwherein M signifies alkali metal, R represents C.sub.1 -C.sub.10 -alkoxy or a group of the formula C.sub.n H.sub.2n+1 --O--C.sub.m H.sub.2m --O--, m and n each individually denote whole numbers of 1 to 7 and x stands for 0, 1, 2 or 3,and subsequently hydrolyzing to give the compound of formula IV and, if desired, converting the compound of formula IV obtained into zeaxanthin.
    Type: Grant
    Filed: March 23, 1990
    Date of Patent: July 13, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup
  • Patent number: 5225608
    Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## wherein A is ##STR2## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 to C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: August 6, 1991
    Date of Patent: July 6, 1993
    Assignee: BASF K & F Corporation
    Inventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
  • Patent number: 5208357
    Abstract: There are provided enantiomerically enhanced chiral substituted cyclopentadienyl ligands and compounds thereof, and a process for their making comprising contacting a substituted fulvene or derivative thereof with an enantiomerically enhanced or pure nucleophile having at least one chiral center. There are further provided enantiomerically enhanced chiral organometallic complexes having one or more chiral substituted cyclopentadienyl groups.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: May 4, 1993
    Assignee: Exxon Chemical Patents, Inc.
    Inventor: Eric A. Mintz
  • Patent number: 5187286
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: February 16, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
  • Patent number: 5185472
    Abstract: Novel mixtures of bicyclic ethers of the formulas ##STR1## wherein R represents an alkyl group of from one to four carbon atoms, said mixture having at least a 1.1:1 ratio of Ia to Ib, a process for their manufacture and their use as odoranis and novel intermediates for their preparation are described.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: February 9, 1993
    Assignee: Givaudan Corporation
    Inventors: Georg Frater, Harald Schmidt
  • Patent number: 5177245
    Abstract: Provided is a process for preparing optionally-substituted cyclohexenylhydroquinones starting from cyclohexanone.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: January 5, 1993
    Assignee: Eastman Kodak Company
    Inventors: Dewey W. Fuller, Jr., Gether Irick, Jr.
  • Patent number: 5137921
    Abstract: There is provided an inhibitory agent of an increase in blood sugar level, comprising conduritol A of the formula(I): ##STR1## or a derivative thereof, as an active component.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: August 11, 1992
    Assignee: Dai-Nippon Sugar Mfg. Co., Ltd.
    Inventors: Ituo Kensho, Fumio Yamashita, Toshikazu Nagai, Tadashi Fujimoto, Yoshihisa Nakano, Hideki Tukimura
  • Patent number: 5087775
    Abstract: A process for the preparation of partially fluorinated alcohols starting from halogen-containing alkenes, and 2,2,3,3,4,4-hexafluorocyclopentanol as a new partially fluorinated alcohol.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: February 11, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Dietmar Bielefeldt, Michael Negele, Heinz Ziemann
  • Patent number: 4978806
    Abstract: A method for preparation of 1-methoxycyclohepta-1,3,5-triene in commercial quantities, which comprises the steps of heating 7,7-dichloro-1-methoxybicyclo[4.1.0]heptane in a refluxing reaction solvent comprising a lower boiling aromatic amine, at reflux, until suitable amounts of 1-methoxycyclohepta-1,3,5-triene have been produced, and recovering the 1-methoxycyclohepta-1,3,5-triene. Suitable reaction solvents include 2-picoline, pyridine and 2,6-lutidine. The method according to the present invention results in safer temperature control in the production of 1-methoxycyclohepta-1,3,5-triene, and increased yields.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: December 18, 1990
    Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of National Defence of Her Majesty's Canadian Government
    Inventor: Gordon E. Langford
  • Patent number: 4948780
    Abstract: Compounds of the general formulae ##STR1## in which R may be a methyl or ethyl radical and R.sup.1 may be a hydrogen, methyl or ethyl radical are disclosed. Also provided as part of the present invention are processes for the preparation of the above compounds. The compounds of the invention are useful as scents.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: August 14, 1990
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Helmut Gebauer, Erich Markl, Marlies Regiert
  • Patent number: 4891451
    Abstract: Vinyl ethers of the formula (I) ##STR1## where R.sup.1 to R.sup.3 are identical or different and are each hydrogen, a straight-chain or branched alkyl or alkenyl radical of not more than 12 carbon atoms, halogen-substituted alkyl, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, alkenylaryl, aralkyl or aralkenyl radical of 6 to 16 carbon atoms, halogen-substituted aryl or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, may form a cycloalkane, cycloalkene or heterocyclic structure, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by a process in which an alcohol is eliminated from an acetal or ketal of the formula (II) ##STR2## where R.sup.1 to R.sup.4 have the above meanings, in the presence of borosilicate and/or iron silicate zeolites as catalysts.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: January 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 4792637
    Abstract: A process for the synthesis of vinyl ethers of formula ##STR1## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or a primary, secondary or tertiary alkyl group,R.sub.3 is a hydrogen, a primary alkyl, phenyl, or substituted phenyl group, orR.sub.2 and R.sub.3, taken together, represent a polymethylene chain containing from 3 to 10 carbon atoms wherein one or more hydrogens can be replaced by methyl or ethyl groups, andR is a primary, secondary or tertiary alkyl group, which comprises reacting a suitably selected dioxolane derivative of formula II ##STR2## wherein R.sub.1, R.sub.2, and R.sub.3 are as defined above, andR.sub.4, R.sub.5, R.sub.6, and R.sub.7, each independently, represent hydrogen or an alkyl group, with a boric acid ester of formula IIIB(OR).sub.3 IIIwhereinR is as defined above, in the vapor phase, at a temperature comprised between 100.degree. and 400.degree. C., and in the presence of an acidic heterogeneous catalyst.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: December 20, 1988
    Assignee: Enichem Anic SpA
    Inventors: Giuseppe Messina, Mario D. Moretti, Salvatore R. Sanna, Giovanni Soma, Pier G. Cabras
  • Patent number: 4703127
    Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.
    Type: Grant
    Filed: September 2, 1983
    Date of Patent: October 27, 1987
    Assignee: The Australian National University
    Inventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
  • Patent number: 4614747
    Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: September 30, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
  • Patent number: 4608445
    Abstract: The compounds of formulaX--CH.sub.2 --CH(OH)--CH.sub.2 --R (I)wherein symbol R represents a C.sub.1 -C.sub.3 alkyl radical and X a substituted cyclohexyloxy group of formula ##STR1## wherein index n stands for zero or one, the dashed lines indicate a single bond (n=1) or a double bond in position 2 (n=0) or 3 (n=1) and each of symbols R.sup.1 to R.sup.6 designates a hydrogen atom or a methyl radical, are new and can be conveniently utilized as perfuming and flavoring ingredients. They develop in particular woody-ambery notes.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: August 26, 1986
    Assignee: Firmenich SA
    Inventors: Wolfgang K. Giersch, Karl H. Schulte-Elte, Gunther Ohloff
  • Patent number: 4604480
    Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.
    Type: Grant
    Filed: August 15, 1983
    Date of Patent: August 5, 1986
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Mohammad Aslam
  • Patent number: 4601851
    Abstract: Cyclododec-2-enyl ethers having the formula ##STR1## wherein R is a straight or branched chain C.sub.1-4 alkyl or alkenyl group, have fragrance characteristics similar to patchouli oil, and are attractive compounds for use in the manufacture of fragrance compositions.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: July 22, 1986
    Assignee: Huels Aktiengesellschaft
    Inventors: Martin Bartmann, Klaus Burzin
  • Patent number: 4593142
    Abstract: Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: June 3, 1986
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4533760
    Abstract: Olefins are produced by contacting an organic compound having at least one benzene ring with calcium metal, ethylenediamine, a low molecular weight aliphatic alcohol, and optionally a low molecular weight aliphatic primary amine, and/or an inert, abrasive particulate substance. The reduction is conducted at temperatures ranging from about -10.degree. C. to about 30.degree. C. or somewhat higher. Substantially all of the organic compounds are converted to corresponding cyclic olefins, primarily diolefins.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: August 6, 1985
    Assignee: Purdue Research Foundation
    Inventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
  • Patent number: 4533752
    Abstract: Olefins are produced by containing an organic compound having at least one benzene ring with ethylenediamine and calcium metal, the calcium metal being used in large excess or alternatively in conjunction with an inert abrasive particulate substance. Substantially all of the organic compounds are converted to corresponding cyclic olefins, largely mono-olefins.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: August 6, 1985
    Assignee: Purdue Research Foundation
    Inventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
  • Patent number: 4506102
    Abstract: 2-Methoxyethyl cyclododec-1-enyl ether is of interest as a precursor for the saturated ether, 2-methoxyethyl cyclododecyl ether, which can be obtained therefrom by catalytic hydrogenation, in a high purity and with a good fragrance quality. The saturated ether is a valuable fragrance component having a woody note. A process for producing 2-methylethyl cyclododec-1-enyl ether comprises the step of reacting cyclododecanone, 2-methoxyethanol and a tri(lower alkyl) orthoformate, at a temperature of 50.degree.-250.degree. C., in the presence of an acid catalyst, removing resultant low-boiling compounds by distillation, and recovering resultant 2-methoxyethyl cyclododec-1-enyl ether.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: March 19, 1985
    Assignees: Chemische Werke Huls AG, Naarden International N.V.
    Inventors: Manfred Kaufhold, Hendrik J. Takken
  • Patent number: 4396781
    Abstract: New compounds of formula ##STR1## wherein symbol R represents a lower alkyl radical and use thereof as perfuming and flavoring ingredients. Process for the preparation of the said compounds.
    Type: Grant
    Filed: November 30, 1979
    Date of Patent: August 2, 1983
    Assignee: Firmenich SA
    Inventors: Wolfgang Giersch, Gunther Ohloff
  • Patent number: 4326996
    Abstract: The present invention relates to substituted cyclohexane derivatives having the structure: ##STR1## wherein the dotted line may be 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,R.sub.6,R.sub.7 and R.sub.8 may be hydrogen or lower alkyl; wherein Z may be any of the following: ##STR2## wherein R.sub.9 may be hydrogen or lower alkyl; and wherein R.sub.10 and R.sub.11 are lower alkyl. This invention also provides methods of preparing and using the compounds as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in foodstuffs and tobacco products.
    Type: Grant
    Filed: January 30, 1980
    Date of Patent: April 27, 1982
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman
  • 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: 4262145
    Abstract: A process for converting an olefin, or a mixture of olefins, to an ether, or a mixture of ethers, which comprises reacting said olefin, or said mixture of olefins, with an alkanol in contact with silicatungstic acid.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: April 14, 1981
    Assignee: Gulf Research & Development Company
    Inventors: Charles M. Selwitz, John G. McNulty
  • Patent number: 4249025
    Abstract: An improved multi-step process for synthesizing the liquid irritant 1-metycycloheptatriene from tropylium tetrafluoborate the improvement comprising the step of using a polymerization/condensation inhibitor or retarder to minimize impurities and increase yield of the irritant product. Phenothiazine is the preferred polymerization inhibitor.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: February 3, 1981
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: William R. Hydro
  • Patent number: 4230823
    Abstract: The instant invention is directed to a process for the preparation of modified polyether polyols comprising polymerizing of from 1 to 50 parts by weight of a mixture of 20 to 100% by weight (based on the total quantity of monomers) of acrylonitrile and 0 to 80% by weight of styrene in 50 to 99 parts by weight of the polyether polyol in the presence of a polymerization initiator which yields radicals, wherein said polymerization is carried out in the presence of from 0.1 to 1.5% by weight, based on the total quantity of monomers put into the process, of a compound of the formula:A=CH--X--RwhereinA represents a divalent group ##STR1## R represents a C.sub.1-18 alkyl, C.sub.1-10 cycloalkyl, or substituted or unsubstituted benzyl group,R' represents C.sub.1-8 alkyl group,n represents 0, 1 or 2 andX represents oxygen or sulfur.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: October 28, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Alberts, Gerhard Balle
  • Patent number: 4169073
    Abstract: Described are perfume and cologne compositions containing the compound 3(2-chloroalkyloxy).sub.2 (10) pinene.This is a divisional of application Ser. No. 872,937, filed Jan. 27, 1978, now U.S. Pat. No. 4,131,687.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: September 25, 1979
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Shuster, James M. Sanders, Bette M. Light, Edward J. Granda
  • Patent number: 4160109
    Abstract: Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals of the formula ##STR1## wherein each R is a primary or secondary C.sub.1-4 alkyl radical are obtained by catalytic hydrogenation of p-benzoquinone tetramethyl-diketal with about 1 mol of H.sub.2 per mole of diketal, in a basic medium, at a temperature of from about -10.degree. to +150.degree. C. and optionally by reketalization with a primary or secondary C.sub.2-4 alcohol in a slightly acid medium with substantial exclusion of water, at a temperature of from about -10.degree. to +35.degree. C. Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals, optionally dissolved in an alcohol ROH give hydroquinone dialkyl ethers on acidification and heating to about 60.degree. to 120.degree. C., which ethers are valuable dyestuff intermediates.
    Type: Grant
    Filed: January 26, 1978
    Date of Patent: July 3, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Rudolf Pistorius
  • Patent number: 4159998
    Abstract: Disclosed is an improved process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone corresponding to the formula ##STR1## wherein m is an integer from 2 to 4. The compounds prepared by this process are useful as precursors in the preparation of carbinol PGE.sub.1 analogues having utility as bronchodilators and inhibitors of gastric secretion.
    Type: Grant
    Filed: September 11, 1978
    Date of Patent: July 3, 1979
    Assignee: Miles Laboratories, Inc.
    Inventor: Harold C. Kluender
  • Patent number: 4156097
    Abstract: Bis-(2-cyclopentenyl) ethers are prepared by contacting a 2-cyclopentenyl carboxylate or 2-cyclopentenol with an aqueous acid solution having a pH in the range of about 1.0 to about 3.0.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: May 22, 1979
    Assignee: Union Carbide Corporation
    Inventors: Benjamin Phillips, Walter J. Skraba
  • Patent number: 4132726
    Abstract: Novel optically active compounds of 4-protected hydroxy-cyclopent-2-en-1-ones of the formula ##STR1## wherein R is a splittable protective group for an alcoholic hydroxyl group, and a process for preparing the 4-protected hydroxycyclopent-2-en-1-ones by oxidizing monohydroxy-protected derivatives of cyclopent-1-ene-3,5-diol expressed by the following formula ##STR2## wherein R is the same as defined above. Optically active 4-hydroxycyclopent-2-en-1-one which is an optically active isomer of the compound of formula (2); or optically active cyclopent-1-en-3,5-diol (R-isomer) and a novel diacyl derivative of the diol, a novel monoacylmonosilyl-derivative of the diol and a novel monoacylmonotetrahydropyranol-derivative of the diol, which are intermediates for the protective derivative of formula (1). Processes are also provided for preparing the protective derivatives of formula (1) by converting these intermediates by esterification, hydrolysis, enzymatic processes, etc.
    Type: Grant
    Filed: December 22, 1975
    Date of Patent: January 2, 1979
    Assignee: Teijin Limited
    Inventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto, Sadakazu Matsubara
  • Patent number: 4131687
    Abstract: Described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, perfumes, colognes, and perfumed articles using as the essential ingredient at least one C.sub.10 -terpene alkyl, alkenyl, haloalkenyl, and alkynyl ether and diether having the formula:(C.sub.10 -TERPENYL) (O-R.sub.1).sub.nwherein n is 1 or 2; the terpene group is a moiety having one of the structures: ##STR1## AND R.sub.1 is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, C.sub.3 alkynyl, or C.sub.3 haloalkenyl. The compounds wherein R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, C.sub.3 alkynyl or C.sub.3 haloalkenyl are novel compounds.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: December 26, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Shuster, James M. Sanders, Bette M. Light, Edward J. Granda