The Hydroxy Is Attached Indirectly To The Ring Patents (Class 568/826)
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Patent number: 5202503Abstract: Novel benzonitriles, benzaldehydes and benzyl alcohols of the formula I ##STR1## where R.sup.1 is methyl or ethyl, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, or C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, X is hydrogen, chlorine or fluorine and Z is --CN, CHO or ##STR2## where R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.2 is not --CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl and Z is ##STR3## and with the proviso that R.sup.2 is not methyl or ethyl when R.sup.1 is methyl and at the same time Z is ##STR4## and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl or ethyl and at the same time Z is --CN or --CHO.Type: GrantFiled: November 12, 1991Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Wolf, Hans Theobald, Norbert Goetz
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Patent number: 5187286Type: GrantFiled: March 25, 1991Date of Patent: February 16, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
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Patent number: 5153229Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing at least 99.99% of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml.Type: GrantFiled: June 1, 1990Date of Patent: October 6, 1992Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
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Patent number: 5132471Abstract: .alpha.-Bisabolol is purified by distilling a plant extract containing .alpha.-bisabolol under reduced pressure and drawing off the purified .alpha.-bisabolol in the lower half of a distillation column as side product, and feeding in the extract above the side outlet.Type: GrantFiled: April 24, 1991Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Gerald Lauterbach, Otto Hertel, Klaus Euler
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Patent number: 4999454Abstract: The invention is directed to a new process for the preparation of carbinols of the general formula I ##STR1## by reaction chloral and olefins of the general formula ##STR2## and by optional acylation of the product comprising dissolving a catalyst of the general formula IIIFe.sub.n (NH.sub.4).sub.x Y.sub.m .multidot.A.sub.p IIIin chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV ##STR3## from which a complex of the general formula V ##STR4## is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter(a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or(b) the product in the reaction mixture is acylated.The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.Type: GrantFiled: October 3, 1985Date of Patent: March 12, 1991Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
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Patent number: 4920096Abstract: High quality cedar wood oil is recovered from raw cedar wood with substantially improved efficiency employing the solvent extraction method of this invention. By submerging cedar wood pulp or sawdust in a suitable water insoluble solvent for a predefined time period, a purified cedar wood oil extract is easily attained after filtration of the cedar wood pulp and distillation removal of the solvent. Furthermore, depending upon the end use or operating system, the solvent extraction method of this invention may be conducted as either a batch process or a continuous process.Type: GrantFiled: October 6, 1988Date of Patent: April 24, 1990Inventor: Paul Z. Bedoukian
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Patent number: 4892941Abstract: Disclosed are tetraphenyl porphyrins which are beta-substituted by fluoro or chloro and/or bear electronegative substituents on the phenyl including one or two water solubilizing substituents. The new porphorins are particularly suitable as catalysts in a variety of oxidative reactions and methods.Type: GrantFiled: April 15, 1988Date of Patent: January 9, 1990Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
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Patent number: 4868339Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formulated into perfurmes, talcs, lotions, cremes and air fresheners.Type: GrantFiled: September 23, 1987Date of Patent: September 19, 1989Assignee: BASF K & F CorporationInventors: Philip A. Christenson, Brian J. Drake
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Patent number: 4710316Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.Type: GrantFiled: August 13, 1986Date of Patent: December 1, 1987Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
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Patent number: 4704477Abstract: Compounds of the general formula ##STR1## wherein A is the ##STR2## group and in which R.sup.1 stands for hydrogen, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropoxy and R.sup.2 and R.sup.3 are hydrogen, methyl and ethyl. The compounds are used as perfume substances.Type: GrantFiled: March 7, 1986Date of Patent: November 3, 1987Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Hans Mehlin, Marlies Regiert
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Patent number: 4638103Abstract: A method of preparing delta-terpineol by reacting 1,8-cineole with an alkali metal aryl compound resulting in an E2 elimination reaction of 1,8-cineole.Type: GrantFiled: October 1, 1985Date of Patent: January 20, 1987Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 4638104Abstract: A method of preparing terpinen-4-ols and intermediates thereof, by reacting 1,4-cineole with an alkali metal aryl compound, resulting in an E2 elimination reaction of 1,4-cineole.Type: GrantFiled: October 1, 1985Date of Patent: January 20, 1987Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 4620045Abstract: Eneynols are prepared from terminal acetylenes and propargylic alcohols using a Cu.sup.+, Ag.sup.+ and/or Au.sup.+ halide catalyst.Type: GrantFiled: March 19, 1985Date of Patent: October 28, 1986Assignee: The Dow Chemical CompanyInventors: Giffin D. Jones, Harold E. Doorenbos
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Patent number: 4609491Abstract: Novel odorant substances of the formula: ##STR1## wherein: one of the three dotted lines represents an optional bond,R.sup.1 represents hydrogen, an alkyl group of one to four carbons or an alkenyl group of two to four carbons,R.sup.2 represents hydrogen or methyl,R.sup.3 represents hydrogen or methyl, provided thatR.sup.2 and R.sup.3 are never both hydrogen, and novel fragrance compositions containing same.Type: GrantFiled: May 23, 1983Date of Patent: September 2, 1986Assignee: Givaudan CorporationInventor: Hanspeter Schenk
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Patent number: 4543431Abstract: Polyunsaturated ketones of formula ##STR1## having a double bond in position 2' or 3' of the side chain and possessing either an isolated double bond in position 1 or 2, or two conjugated double bonds in positions 1 and 3 of the ring, as indicated by the dotted lines, andwhereinindex n stands for integer 1 or 2, andeach of the symbols R.sup.1 to R.sup.7, identical or different, designates a hydrogen atom or a lower radical,are prepared by a process which makes use of tertiary diallyl carbinols as starting materials.Type: GrantFiled: February 14, 1984Date of Patent: September 24, 1985Assignee: Firmenich SAInventors: Karl H. Schulte-elte, Roger L. Snowden, Bernard L. Muller
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Patent number: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4392993Abstract: New alicyclic unsaturated compounds useful as perfume ingredients and perfume compositions containing same. The new compounds have formula ##STR1## possessing a methyl group attached to the carbon atom at position 3 or 4 of the ring and one double bond in one of the positions of the carbonyl side chain as indicated by the dotted line.Type: GrantFiled: July 23, 1981Date of Patent: July 12, 1983Assignee: Firmenich, SAInventors: Alan F. Thomas, Ferdinand Naf
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Patent number: 4348543Abstract: The present invention describes cycloaliphatic alcohols prepared via a Diels-Alder reaction.Type: GrantFiled: February 12, 1981Date of Patent: September 7, 1982Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4301018Abstract: Described are cyclohexenemethanols and uses thereof in augmenting or enhancing the aroma of fabric softener articles.Type: GrantFiled: January 18, 1980Date of Patent: November 17, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4301309Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff, medicinal product and tobacco flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes and are, themselves, useful for their organoleptic properties in perfumery and flavors as are the esters of said cyclohexenemethanols.Type: GrantFiled: November 16, 1979Date of Patent: November 17, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4283576Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes.Type: GrantFiled: December 5, 1979Date of Patent: August 11, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4263208Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff, medicinal product and tobacco flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes and are, themselves, useful for their organoleptic properties in perfumery and flavors as are the esters of said cyclohexenemethanols.Type: GrantFiled: November 16, 1979Date of Patent: April 21, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4250342Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as organometallic salts of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols and their organometallic salts are useful as precursors for the oxabicyclooctanes.Type: GrantFiled: November 16, 1979Date of Patent: February 10, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4250049Abstract: Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of adding to a solid or liquid anionic, cationic or nonionic detergent base from 0.005% up to 5% by weight of at least one compound defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond with the proviso that when R.sub.1 is hydrogen, the dashed line represents a carbon-carbon double bond.Type: GrantFiled: February 8, 1980Date of Patent: February 10, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, William L. Schreiber, Braja D. Mookherjee, Jacob Kiwala, Joaquin F. Vinals, Manfred H. Vock, Gilbert Stork, Frederick L. Schmitt
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Patent number: 4250118Abstract: An improved process for the preparation of cyclohexanone from benzene. Benzene is hydrogenated in a gaseous phase in a hydrogenation zone to form cyclohexane; cyclohexane is oxidized in a liquid phase to form a mixture containing cyclohexanol and cyclohexanone; and cyclohexanone is separated from this mixture and is catalytically dehydrogenated to form cyclohexanone and a hydrogen containing gas. The resulting hydrogen containing gas is introduced into a washing zone wherein it is washed with cyclohexane or benzene and the hydrogen gas thus purified is fed into the hydrogenation zone.Type: GrantFiled: April 20, 1979Date of Patent: February 10, 1981Assignee: Stamicarbon, B.V.Inventors: Theodorus J. van de Mond, Hubertus J. A. Delahaye
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Patent number: 4243823Abstract: Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, smoking tobacco flavor and aroma and perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, smoking tobacco, perfume and perfumed article aroma and/or flavor imparting materials of 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanol and -1,3-cyclohexadiene-1-methanol derivatives or one or more of their geometric or stereoisomers as defined by the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; the dashed line is a carbon-carbon double bond or a carbon-carbon single bond; with the proviso that when R.sub.1 is hydrogen, the dashed line is a carbon-carbon double bond.Addition of one or more of the 2,6,6-trimethyl-.alpha.Type: GrantFiled: May 15, 1979Date of Patent: January 6, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, William L. Schreiber, Braja D. Mookherjee, Jacob Kiwala, Joaquin F. Vinals, Manfred H. Vock, Gilbert Stork, Frederick L. Schmitt
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Patent number: 4222941Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as organometallic salts of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols and their oganometallic salts are useful as precursors for the oxabicyclooctanes.Type: GrantFiled: June 15, 1979Date of Patent: September 16, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4221721Abstract: Described are cyclic chemical compounds useful for their organoleptic properties in flavors, fragrances, colognes, perfumed articles and smoking tobaccos defined according to the structure: ##STR1## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is C.sub.4 or C.sub.5 alkyl or C.sub.Type: GrantFiled: June 27, 1979Date of Patent: September 9, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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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
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Patent number: 4215230Abstract: Ionones and irones are produced by thermal rearrangement of novel propargylic alcohols, as follows: ##STR1## wherein R.sup.1 is a lower alkyl group, R.sup.2 is hydrogen or methyl and the dotted lines in the product formula reflect the existence of a double bond at either one or the other of the positions indicated.Type: GrantFiled: May 23, 1978Date of Patent: July 29, 1980Assignee: Kuraray Co., Ltd.Inventors: Takashi Ohnishi, Yoshiji Fujita, Michihiro Ishiguro, Takashi Nishida
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Patent number: 4197328Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes.Type: GrantFiled: February 2, 1979Date of Patent: April 8, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4195100Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as organometallic salts of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols and their organometallic salts are useful as precursors for the oxabicyclooctanes.Type: GrantFiled: February 16, 1979Date of Patent: March 25, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4195099Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff, medicinal product and tobacco flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes and are, themselves, useful for their organoleptic properties in perfumery and flavors as are the esters of said cyclohexenemethanols.Type: GrantFiled: October 20, 1978Date of Patent: March 25, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4172850Abstract: Described is a process for preparing several 1-acyl-2,6,6-trimethylcyclohexene derivatives defined by the generic structure: ##STR1## wherein R.sub.1 is hydrogen or ethylidene having the structure:[H.sub.3 C--C.dbd. ;R.sub.2 is hydrogen or no group; one of the wavy lines is a carbon-carbon double bond and the other of the wavy lines is a carbon-carbon single bond; with the proviso that when the .DELTA..sup.2,3 bond (as shown by the wavy line between the "2" and the "3" position of the ring) is a carbon-carbon double bond, then R.sub.2 is hydrogen and R.sub.Type: GrantFiled: December 1, 1978Date of Patent: October 30, 1979Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
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Patent number: 4140690Abstract: Terpenes are oxidized by contacting the terpene and oxygen with a catalyst. The catalyst may be either (a) a bismuth molybdate or (b) antimony oxide containing iron oxide and/or uranium oxide.Type: GrantFiled: April 22, 1977Date of Patent: February 20, 1979Assignee: The Standard Oil CompanyInventors: Serge R. Dolhyj, Louis J. Velenyi
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Patent number: 4125484Abstract: Novel tertiary alcohols of the general formula: ##STR1## in which R.sub.1 represents an alkenyl or a cycloalkyl or cycloalkenyl optionally substituted by one or more alkyl groups, R.sub.2 represents hydrogen or alkyl; or R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, from a bicyclo group optionally substituted by up to two alkyl groups; R.sub.3 and R.sub.4 each represents an alkyl group, and Y represents a divalent aliphatic group of up to 4 carbon atoms, are disclosed along with their use as aroma chemicals and a process for their preparation.Type: GrantFiled: February 24, 1977Date of Patent: November 14, 1978Assignee: Shell Oil CompanyInventors: Robin T. Gray, Aaldert J. De Jong
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Patent number: 4113968Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.Type: GrantFiled: September 26, 1975Date of Patent: September 12, 1978Assignee: Kuraray Co., Ltd.Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi