Terpenic, Wherein The Number Of Carbons Is A Multiple Of Five (e.g., Linalool, Farnesol, Etc.) Patents (Class 568/875)
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Patent number: 5550297Abstract: A process for catalytic preparation of alcohols or amines by reaction of esters, fatty acids, or nitriles with hydrogen at elevated temperature and pressure. The unreduced catalyst contains, per 100 parts by weight of CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al.sub.2 O.sub.3, and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr, and/or alkaline earth metal. It has a BET total area of 80 to 175 m.sup.2 /g of catalyst in the unreduced state, and 75% to 95% of the BET total area is formed by pores having a radius r.sub.p .ltoreq.15 nm.Type: GrantFiled: February 16, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl D. Frohning
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Patent number: 5516948Abstract: Mixtures of isomeric decyl alcohols obtained by oligomerization of propylene in the presence of deactivated zeolites as catalysts, followed by separation of the nine carbon olefins from the oligomer mixture, then hydroformylation of the 9 carbon olefins to 10 carbon aldehydes, and hydrogenation of the aldehydes to the corresponding alcohols. The mixtures, when esterified with phthalic acid, or anhydride, provide a mixture of isomeric di-decyl phthalates that can be used as plasticizers.Type: GrantFiled: June 7, 1995Date of Patent: May 14, 1996Assignee: Hoechst AGInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5349097Abstract: A process for the catalytic isomerization of secondary .alpha.-alkenols of formula I ##STR1## in which R.sup.1 is a C.sub.1 -C.sub.20 alkyl group or a C.sub.2 -C.sub.2 alkenyl group and in which R.sup.2 stands for hydrogen, a halogen atom, a C.sub.1 -C.sub.10 alkoxy group, a carbonyl group, or a C.sub.1 -C.sub.20 alkyl group and in which R.sup.1 and R.sup.2 can be joined together to complete a five-membered or six-membered carbocyclic ring, to primary .alpha.-alkenols of formula II ##STR2## or for the isomerization of primary .alpha.-alkenols of formula II to secondary .alpha.-alkenols of formula I, wherein the isomerization is carried out in the presence of organotrioxorhenium(VII) compounds of formula III ##STR3## in which R.sup.3 is a C.sub.1 -C.sub.10 alkyl group, a cyclopentadienyl group substituted by from one to five C.sub.1 -C.sub.4 alkyl groups, an unsubstituted cyclopentadienyl group, a C.sub.6 -C.sub.10 aryl group, or a C.sub.7 -C.sub.Type: GrantFiled: July 29, 1993Date of Patent: September 20, 1994Assignee: BASF AktiengesellschaftInventors: Alfred Thome, Michael Roeper, Heinz-Josef Kneuper
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Patent number: 5280048Abstract: A .beta.,.gamma.-dihydropolyprenyl alcohol derivative having the formula: ##STR1## wherein n is an integer of 5 to 7 and R is hydrogen, a lower alkyl group or an aliphatic or aromatic acyl group, is new and usrful as a prophylactic therapeutic agent for human and animal immuno-deficiency deseases and phylactic agent against human and animal infectious deseases. Another disclosed polyprenyl compound is also useful as the same agent.Type: GrantFiled: January 29, 1993Date of Patent: January 18, 1994Assignee: Eisai Co., Ltd.Inventors: Masaichi Yamamoto, Seiichi Araki, Hiroshi Yamamoto, Isao Yamatsu, Takeshi Suzuki, Akiharu Kajiwara, Yoshikazu Suzuki, Haruyoshi Arai
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Patent number: 5264638Abstract: A process for the extraction and purification of the diterpene alcohol Plaunotol from the leaves of the medicinal plant, Croton sublyratus Kurz. The process involves extracting firstly with a lower aliphatic alcohol followed by extracting from the alcohol solution with a chlorinated hydrocarbon. Then impurities are hydrolysed and the required Plaunotol separated by extraction with a hydrocarbon. This process is simple and gave much better yields than prior processes.Type: GrantFiled: January 28, 1992Date of Patent: November 23, 1993Assignee: Chulalongkorn UniversityInventor: Naline Nilubol
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Patent number: 5175378Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.Type: GrantFiled: March 16, 1992Date of Patent: December 29, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5175371Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.Type: GrantFiled: March 16, 1992Date of Patent: December 29, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5118884Abstract: The invention concerns the production of a diolefinic unsaturated alcohol such as geraniol or nerol by the selective hydrogenation of citral. It is characterized by the use of a catalyst based on a metal from group VIII and based on a metal selected from the group made up of tin, germanium and lead, on preferably a silica carrier.Type: GrantFiled: September 6, 1990Date of Patent: June 2, 1992Assignee: Institut Francais du PetroleInventors: Blaise Didillon, Jean-Pierre Candy, Jean-Marie Bassett, Jean-Paul Bournonville
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Patent number: 5095155Abstract: Closely boiling diastereomeric isomer alcohols are separated by converting them to esters having disparate boiling points, separating the ester isomers by distillation and saponifying the separate ester isomers to obtain the individual alcohol isomers.Type: GrantFiled: June 7, 1990Date of Patent: March 10, 1992Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 5012018Abstract: A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols.Type: GrantFiled: September 25, 1984Date of Patent: April 30, 1991Assignee: Kuraray Co., Ltd.Inventors: Yasuyuki Tanaka, Koichi Ibata, Masao Mizuno, Yoichi Ninagawa, Takashi Nishida
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Patent number: 4962242Abstract: A process for producing an optically active alcohol represented by formula (I): ##STR1## wherein R.sub.1 is an alkyl group having from 2 to 11 carbon atoms, an alkenyl group having from 3 to 11 carbon atoms, an alkadienyl group having from 6 to 11 carbon atoms, a cyclohexyl group, an cyclohexylmethyl group, or a cyclohexylethyl group, provided that the olefin in the alkenyl group or alkadienyl group is not conjugated to the olefin at the 2-position thereof; and * means an asymmetric carbon atom,is disclosed, comprising subjecting an olefinic alcohol represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above to asymmetric hydrogenation in the presence of, as a catalyst, a ruthenium-optically active phosphine complex.According to the process of the invention, the desired optically active alcohols which are useful not only as intermediates for the manufacture of perfumes and vitamin E but also as liquid crystal materials can be produced with high optical purities.Type: GrantFiled: June 25, 1987Date of Patent: October 9, 1990Assignee: Takasago Perfumery Co., Ltd.Inventors: Nobuo Yamada, Toshiyuki Takezawa, Noboru Sayo, Misao Yagi, Hidenori Kumobayashi, Susumu Akutagawa, Hidemasa Takaya, Shinichi Inoue, Ryoji Noyori
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Patent number: 4886904Abstract: A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols.Type: GrantFiled: August 5, 1987Date of Patent: December 12, 1989Assignee: Kuraray Co., Ltd.Inventors: Yasuyuki Tanaka, Koichi Ibata, Masao Mizuno, Yoichi Ninagawa, Takashi Nishida
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Patent number: 4825012Abstract: Allylic 1-hydroxy alcohols are inverted to allylic 3-hydroxy alcohols by: (1) epoxidizing the allyl group of the allylic 1-hydroxy alcohol to the corresponding 2,3-epoxy-1-hydroxy alcohol; (2) transforming the 2,3-epoxy-1-hydroxy alcohol compound to a 1,2-dihalo-3-hydroxy alcohol; and (3) dehalogenating the 1,2-dihalo-3-hydroxy alcohol to form the desired allylic 3-hydroxy alcohol.Type: GrantFiled: December 7, 1987Date of Patent: April 25, 1989Assignee: Akzo America Inc.Inventor: Andrea Leone-Bay
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Patent number: 4791222Abstract: Described is a novel process for preparing dihydromyrcenol defined according to the structure: ##STR1## or the acetate thereof comprising the steps of: (i) hydrogenating .alpha.-pinene to form .alpha.-pinane;(ii) pyrolizing the resulting .alpha.-pinane to form a mixture of hydrocarbons including dihydromyrcene (or, in the alternative, forming substantially the same mixture of hydrocarbons by other well known means);(iii) reacting the resulting pinane pyrolyzate or like mixture with hydrogen chloride gas in the presence of an acid catalyst, e.g., Lewis acid or protonic acid, to form a mixture of tertiary chlorides; then(iv) reacting the mixture of tertiary chlorides with water or acetic acid int he presence of a hydroxylation catalyst defined according to the formula:M.sub.P X.sub.Qwherein M represents an element selected from the group consisting of Zn, Ca, Mg, Mn and Co; wherein X represents O or an anion, e.g.Type: GrantFiled: July 31, 1984Date of Patent: December 13, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Stephen R. Wilson, Leonard Steinbach, Thomas O'Rourke
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Patent number: 4720327Abstract: Distillative separation of liquid mixtures of one or more water-insoluble substances which have boiling points higher than that of water and one or more substances which have boiling points lower than that of water or which form azeotropes having boiling points lower than that of water, wherein the mixture to be distilled is mixed with a quantity of water such that the boiling point of the water under the pressure applied limits the bottom temperature of the mixture of substances to be separated.Type: GrantFiled: September 20, 1982Date of Patent: January 19, 1988Assignee: BASF AktiengesellschaftInventors: Werner Aquila, Axel Nissen, Gerd Kaibel, Michael Horner, Walter Rebafka
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Patent number: 4701542Abstract: A process for the resolution of hemiacetal compounds of the formula ##STR1## wherein A is a hydrocarbon chain containing 1 to 16 groups, the said chain optionally containing at least one heteroatom, at least one unsaturation, the assembly of the group constituting the chain may be a mono- or polycyclic system including a spiro or endosystem and the assembly of chain A and the carbon atoms attached thereto can contain at least one chiral atom or the hemiacetal moiety thereto which can present a chirality due to the dissymetric spatial configuration of the molecule and Y is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms optionally substituted, --CY.sub.3 ' and the .beta.,.gamma.Type: GrantFiled: March 31, 1986Date of Patent: October 20, 1987Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute
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Patent number: 4668820Abstract: Polyprenols or esters thereof, which are similar in the trans and cis configurations to dolichol, or mixtures thereof are obtained from the leaves of plants belonging to the genus Pinus L. of the family Pinaceae by extraction, if necessary followed by hydrolysis, esterification or transesterification or a combination thereof. These polyprenyl compounds and mixtures thereof are useful as favorable starting materials for the synthesis of dolichol.Type: GrantFiled: April 10, 1985Date of Patent: May 26, 1987Assignee: Kuraray Co., Ltd.Inventors: Koichi Ibata, Tetsuo Takigawa, Masafumi Okada, Masao Mizuno, Takashi Nishida
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Patent number: 4665221Abstract: An improved process for the preparation of primary terpenoid alcohols, e.g. 6,7-dihydrogeraniol and phytol, and of their esters with formic acid. The terpenoid formates are obtained very advantageously by reacting the corresponding tert.-vinylcarbinols with more than 2 moles, per mole of vinylcarbinol, of aqueous formic acid of more than 70 percent strength by weight, or with anhydrous formic acid, at from 5.degree. to 100.degree. C. The primary terpenoid alcohols themselves are obtained from their formates by trans-esterification with a low-boiling alcohol in the presence of a catalytic amount of a strong base. The products are valuable compounds. For example, 6,7-dihydrogeraniol is used as a scent and phytol is used as a perfume fixative and as a starting material for the synthesis of naturally occurring materials.Type: GrantFiled: July 25, 1983Date of Patent: May 12, 1987Assignee: BASF AktiengesellschaftInventors: Frank Thoemel, Werner Hoffmann
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Patent number: 4605793Abstract: Described is a process for preparing at least one secondary alcohol of the class of methyl substituted pinyl hydroxy pentenes comprising the step of:(i) reacting alpha pinene or beta pinene with a mixture of carbon monoxide and hydrogen in the presence of a hydroformalation catalyst in order to produce at least one methyl substituted pinyl carboxyaldehyde;(ii) reacting the resulting methyl substituted pinyl carboxyaldehyde with methyl ethyl ketone in the presence of a basic catalyst; and(iii) reacting the resulting product with a reducing agent selected from the group consisting of alkali metal borohydrides and lithium aluminum hydride.Type: GrantFiled: July 13, 1984Date of Patent: August 12, 1986Assignee: International Flavors & Fragrances, Inc.Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
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Patent number: 4520212Abstract: Myrcenol is produced in an effecient, high yield and economical process by deaminating 7-hydroxygeranyl dialkylamine or 7-hydroxyneryl dialkylamine with a specific palladium-phosphine-cation complex catalyst represented by the formula[<.cndot.:PdL].sup.+ X.sup.-wherein <.cndot.: represents .eta.-allyl, L represents a tertiary phosphine, and X represents a counter anion.Type: GrantFiled: December 21, 1983Date of Patent: May 28, 1985Assignee: Takasago Perfumery Co., Ltd.Inventors: Shigeru Mitsuhashi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4482765Abstract: An improved process for the preparation of hydroxycitronellol by an addition reaction of water with citronellol. This reaction takes place directly on heating a homogeneous solution of citronellol in a mixture of water and an inert solvent selected from the group consisting of acetone, methyl ethyl ketone, glymes, and tetrahydrofuran. The reaction is catalyzed with a cation exchange resin.Type: GrantFiled: June 24, 1983Date of Patent: November 13, 1984Assignee: Union Camp CorporationInventor: Mark S. Pavlin
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Patent number: 4476147Abstract: A process for augmenting or enhancing the aroma or taste of alliaceous flavors, particularly garlic flavors, by augmenting or enhancing the garlic and green aroma and taste nuances of alliaceous-flavored foodstuffs comprising the step of adding to a alliaceous-flavored foodstuff an aroma or taste augmenting quantity of a mixture of cis and trans isomers of a compound having the structure: ##STR1## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond.Type: GrantFiled: October 17, 1983Date of Patent: October 9, 1984Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, James M. Sanders, James N. Siano
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Patent number: 4467118Abstract: There is disclosed a novel process for converting allylic amines, having a hydrogen bonded to a carbon .delta. to the amino group, to a diene in the presence of a zero valent palladium phosphine complex and a weak acid. The process has been used to make novel compositions containing 7-methoxy-3,7-dimethyloctadienes which are useful as odorants and flavorants.Type: GrantFiled: March 3, 1982Date of Patent: August 21, 1984Assignee: Givaudan CorporationInventors: Alan J. Chalk, Steven A. Magennis, Vasile S. Wertheimer, Richard E. Naipawer
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Patent number: 4455442Abstract: Olefinically unsaturated alcohols (I) are prepared by selective hydrogenation of the corresponding carbonyl compounds (II) in the liquid phase with hydrogen, using an Ru, Rh, Os, Ir or Pt catalyst and carrying out the hydrogenation in the presence of from 5 to 40% by weight, based on (II), of a tertiary amine.The process is of particular importance for the selective hydrogenation of .alpha.,.beta.-unsaturated carbonyl compounds (IIa) and amongst these specifically for the hydrogenation of citral to geraniol and nerol.The preferred amine is trimethylamine.Type: GrantFiled: July 8, 1980Date of Patent: June 19, 1984Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang, Axel Nissen
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Patent number: 4438286Abstract: A novel substituted diene alcohol represented by a general formula: ##STR1## wherein X represents a group of the formula ##STR2## and a process for the preparation thereof wherein a lower alkoxycarbonyl group of a substituted diene carboxylic acid ester having an E configuration obtained by the treatment of a chrysanthemic acid ester with Bronsted acid or a substituted diene carboxylic acid ester having a Z configuration obtained by the thermal cleavage of a chrysanthemic acid ester is reduced to methylol derivative.Type: GrantFiled: October 8, 1982Date of Patent: March 20, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Gohfu Suzukamo, Mitsuhisa Tamura, Masami Fukao
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Patent number: 4399301Abstract: Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.Type: GrantFiled: September 13, 1979Date of Patent: August 16, 1983Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4399062Abstract: Described are compounds defined according to the structure: ##STR1## taken alone or in admixture wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines are carbon-carbon single bonds; wherein R.sub.1 represents C.sub.1 -C.sub.4 alkyl; R.sub.2 represents C.sub.1 -C.sub.4 alkyl; Z represents oxygen or sulfur; R.sub.3 represents hydrogen, MgX, Li, C.sub.1 -C.sub.3 lower alkyl or C.sub.1 -C.sub.3 lower acyl; and wherein X represents chloro, bromo or iodo and uses thereof in augmenting or enhancing the aroma and/or taste of consumable materials such as perfume compositions, colognes, perfumed articles, e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or dryer-added fabric softener articles, smoking tobaccos, chewing gums, chewing tobaccos, medicinal products or toothpastes.Type: GrantFiled: November 19, 1981Date of Patent: August 16, 1983Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4386227Abstract: A process for the preparation of a two-functional-group-containing terpen having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl, or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.Type: GrantFiled: March 22, 1982Date of Patent: May 31, 1983Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
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Patent number: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4382151Abstract: 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraene-2-ols of the general formula: ##STR1##Type: GrantFiled: August 27, 1981Date of Patent: May 3, 1983Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Takeshi Suzuki, Toshiharu Ohgoh, Manabu Murakami, Kiyoshi Oketani, Hideaki Fujisaki
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Patent number: 4338170Abstract: A cis-trans isomerization of a cis-.beta.-.gamma.-unsaturated alcohol or its ester having the formula ##STR1## wherein R.sub.1 represents hydrogen atom or a C.sub.1 -C.sub.5 alkyl group; X represents hydrogen atom or ##STR2## and R.sub.2 represents a hydrocarbon moiety or a hydroxyhydrocarbon moiety; R.sub.3 represents hydrogen atom or a hydrocarbon moiety into a transform, in the presence of a mercaptan as a catalyst, is provided. It can be also attained in the presence of a mercaptan and/or a disulfide as a catalyst in an inert gas environment with an initiator. It can be also attained in the presence of a mercaptan under an irradiation, if desired with a small amount of an initiator.Type: GrantFiled: May 23, 1980Date of Patent: July 6, 1982Assignee: Nissan Chemical Industries, Ltd.Inventors: Atsuo Murata, Syuji Tsuchiya, Hideo Suzuki
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Patent number: 4336164Abstract: Described is the novel compound genus defined according to the structure: ##STR1## wherein R.sub.1 is selected from the group consisting of methyl and isopropyl alcohol and wherein the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds useful in augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes, perfumed articles (including solid or liquid anionic, cationic, nonionic or zwitterionic detergents) smoking tobacco or smoking tobacco articles.Type: GrantFiled: April 9, 1981Date of Patent: June 22, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4331814Abstract: 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: GrantFiled: February 1, 1973Date of Patent: May 25, 1982Assignee: Rhone Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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.beta., .gamma.-Dihydropolyprenyl alcohol and hypotensive pharmaceutical composition containing same
Patent number: 4325974Abstract: .beta., .gamma.-Dihydropolyprenyl alcohols of the general formula: ##STR1## wherein n represents an integer of 8 to 10, exhibit hypotensive activity and anti-hepatic disease-activity.Type: GrantFiled: November 21, 1979Date of Patent: April 20, 1982Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Shinya Abe, Yuichi Inai, Toshiji Igarashi, Yoshikage Nakajima -
Patent number: 4293497Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition on the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: March 18, 1980Date of Patent: October 6, 1981Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia U. Din
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Patent number: 4292454Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: March 18, 1980Date of Patent: September 29, 1981Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia Ud Din
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Patent number: 4266087Abstract: The instant invention provides a new and improved method of preparing the Diels Alder mixture of 3 and 4-(4-methyl-4-hydroxyamyl).DELTA..sup.3 -cyclohexenecarboxaldehyde from the readily available myrcene. The novel sequence includes a synthesis of a novel myrcenol, ocimenol intermediate which is substantially free of trans-ocimenol.Type: GrantFiled: November 13, 1978Date of Patent: May 5, 1981Assignee: Givaudan CorporationInventors: Alan J. Chalk, Steven A. Magennis
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Patent number: 4254291Abstract: A process for allylic rearrangement, particularly terpenoid allylic rearrangement, utilizing certain acid forming metals to form an ester or alcoholate (alcohologen) of the allylic alcohol to be rearranged, isomerizing and cleaving the alcohologen in the presence of a transition metal compound catalyst and recovering the rearranged alcohol.Type: GrantFiled: August 22, 1979Date of Patent: March 3, 1981Assignee: SCM CorporationInventor: Bernard J. Kane
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Patent number: 4247723Abstract: Dihydromyrcenol (3,7-dimethylocta-1-en-7-ol) and carboxylic acid esters thereof are prepared from dimethylcyclooctene reactant mixtures comprising 1,5-dimethylcyclooctene in admixture with 1,6-dimethylcyclooctene and/or 1,4-dimethylcyclooctene by (a) thermally isomerizing the dimethylcyclooctene reactant mixture to afford a mixed octadiene product comprising 2,6-dimethylocta-1,7-diene in admixture with 2,7-and/or 2,5-dimethylocta-1,7-diene, (b) reacting the mixed octadiene product with a carboxylic acid to selectively form the ester of 3,7-dimethyl-octa-1-en-7-ol and (c) optionally hydrolyzing the ester of 3,7-dimethyl-octa-1-en-7-ol under basic conditions to yield dihydromyrcenol.Type: GrantFiled: January 21, 1977Date of Patent: January 27, 1981Assignee: Shell Oil CompanyInventor: Aaldert J. de Jong
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Patent number: 4239923Abstract: Novel cyclooctene derivatives of the formula: ##STR1## in which R.sup.1 and R.sup.2 each represents an alkyl group and R.sup.3 is hydrogen or an acyl group are disclosed along with their use as aroma chemicals and/or aroma chemical precursors and processes for their preparation.Type: GrantFiled: November 2, 1979Date of Patent: December 16, 1980Assignee: Shell Oil CompanyInventors: Aaldert J. deJong, Hendricus J. Heijmen
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Patent number: 4228313Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: December 29, 1977Date of Patent: October 14, 1980Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia U. Din
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Patent number: 4223012Abstract: An attractant, and synthesis thereof, for the San Jose scale, Quadraspidiotus perniciosus.Type: GrantFiled: April 2, 1979Date of Patent: September 16, 1980Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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Patent number: 4221742Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: December 29, 1977Date of Patent: September 9, 1980Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia U. Din
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Patent number: 4214098Abstract: Novel cyclooctene derivatives of the formula: ##STR1## in which R.sup.1 and R.sup.2 each represents an alkyl group and R.sup.3 is hydrogen or an acyl group are disclosed along with their use as aroma chemicals and/or aroma chemical precursors and processes for their preparation.Type: GrantFiled: October 25, 1977Date of Patent: July 22, 1980Assignee: Shell Oil CompanyInventors: Aaldert J. de Jong, Hendricus J. Heijmen
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Patent number: 4200766Abstract: An improved process for the preparation of hydroxycitronellol by an addition reaction of water with citronellol. This reaction takes place directly on heating a homogeneous solution of citronellol in a mixture of water and an .alpha.-methyl-branched lower alkanol in the presence of a strongly acid ion exchanger.Hydroxycitronellol may be used as a fragrance material and is an important intermediate for the preparation of the highly desired scent hydroxycitronellal.Type: GrantFiled: November 17, 1978Date of Patent: April 29, 1980Assignee: BASF AktiengesellschaftInventor: Werner Hoffmann
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Patent number: 4188498Abstract: Linalool is produced by a hydrogenation of O-linalyl-N,N-dimethyl hydroxylamine having the formula ##STR1## wherein Me represents methyl group and the reference numerals 1 to 10 represent 1 to 10 carbon positions under a hydrogen partial pressure of lower than 30 Kg/cm.sup.2 in the presence of a catalyst of a combination of Ni or Co component with a modifying component selected from the group consisting of Al, Ge, Sn, As, Sb, S, Se and Cr.Type: GrantFiled: May 3, 1978Date of Patent: February 12, 1980Assignee: Nissan Chemical Industries, Ltd.Inventors: Atsuo Murata, Shuji Tsuchiya, Hideo Suzuki, Hisao Ikeda
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Patent number: 4179579Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.Type: GrantFiled: July 25, 1977Date of Patent: December 18, 1979Assignee: Kuraray Co., Ltd.Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
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Patent number: 4152530Abstract: A process for preparing allylic alcohols from allylic halides is provided by way of the intermediate formation of an ester in the presence of a water-insoluble ketone forming an azeotrope in water followed by saponification of the ester with alkali metal hydroxide, drying the alkali metal carboxylic acid salt formed during the saponification by azeotropic distillatiion with the ketone, thus obviating expensive separate recovery facilities and handling of the dried alkali metal carboxyolate salt. The overall process amounts to a hydrolysis of the allylic halide with aqueous alkali metal hydroxide and one reactor can serve for the whole process.Type: GrantFiled: July 24, 1978Date of Patent: May 1, 1979Assignee: Rhone-Poulenc Inc.Inventor: Peter S. Gradeff
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Patent number: 4147708Abstract: A novel procedure for the preparation of carotenoids, particularly vitamin A, employing .pi.-allyl transition metal complexes. Novel carotenoid intermediates are also disclosed.Type: GrantFiled: May 2, 1977Date of Patent: April 3, 1979Assignee: Hoffmann-La Roche Inc.Inventor: Percy S. Manchand
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Patent number: 4134919Abstract: A process for producing menthone comprising dehydrogenating citronellol in the presence of a dehydrogenation catalyst at about 150 to about 260.degree. C in an atmosphere of hydrogen under a pressure of 0 to about 5 kg/cm.sup.2. G and a process for producing menthol. Since the dehydrogenation catalyst has a hydrogenating ability, an embodiment additionally includes the ability to ultimately produce menthol in the same reactor without separating the catalyst or adding additional or another catalyst to the system by simply changing the temperature and the hydrogen pressure. Embodiments also include producing menthone and also ultimately menthol utilizing geraniol or a mixture of geraniol and citronellol as a starting material again without catalyst separation or use of additional or another catalyst.Type: GrantFiled: June 14, 1977Date of Patent: January 16, 1979Assignee: Takasago Perfumery Co., Ltd.Inventors: Tohr Yamanaka, Misao Yagi