Oxy Containing Reactant Patents (Class 568/361)
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Patent number: 4510330Abstract: Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula: ##STR1## by the oxy-Cope rearrangement of a diethylenic alcohol of the formula: ##STR2## in which the transformation is carried out in the presence of a catalytic amount of a divalent palladium compound.In the depicted formulae R.sub.1, R.sub.4 and R.sub.6 each represent a hydrogen atom or a hydrocarbon radical, R.sub.2 represents a hydrogen atom and R.sub.3 and R.sub.5 each represent a hydrocarbon radical, or R.sub.3 and R.sub.4 together represent an alkylene radical (--CH.sub.2 --).sub.n (wherein n is an integer from 3 to 20 inclusive) in which one or more carbon atoms can optionally carry as substituent(s) one or more alkyl radicals containing 1 to 4 carbon atoms.The carbonyl products are useful as starting materials for the preparation of compounds intended for use in pharmacy, in agriculture or perfumery.Type: GrantFiled: June 21, 1982Date of Patent: April 9, 1985Assignee: Rhone-Poulenc SanteInventors: Norbert Bluthe, Jacques Gore, Max Malacria
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Patent number: 4510329Abstract: A process for preparing cyclopentenolones of the formula ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl or alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.Type: GrantFiled: November 28, 1980Date of Patent: April 9, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4496767Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.Type: GrantFiled: October 18, 1983Date of Patent: January 29, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4479011Abstract: 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, and whereinindex 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 alkyl radical,are prepared by a process which makes use of tertiary diallyl carbinols as starting materials.Type: GrantFiled: June 25, 1982Date of Patent: October 23, 1984Assignee: Firmenich SAInventors: Karl H. Schulte-Elte, Roger L. Snowden, Bernard L. Muller
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Patent number: 4460792Abstract: Useful perfumery ingredients delta- and epsilon-damascone are prepared by a process which consists in an anionic cleavage, in the presence of a strong base of a diallyl alcohol of formula ##STR1## wherein the dashed lines in position 3 or 4 of the ring designate a double bond, followed by an isomerization of the terminal double bond of the thus obtained product by means of an acidic isomerizing agent.Type: GrantFiled: August 19, 1982Date of Patent: July 17, 1984Assignee: Firmenich S.A.Inventors: Karl H. Schulte-Elte, Roger L. Snowden, Bernard L. Muller
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Patent number: 4453013Abstract: Novel acetylenic compounds useful as starting materials for the preparation of .beta.-damascenone. Process for their preparation and use thereof.Type: GrantFiled: November 19, 1981Date of Patent: June 5, 1984Assignee: Firmenich, S.A.Inventor: Peter Fankhauser
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Patent number: 4429164Abstract: Cyclohexadiene derivatives represented by the formula (I) ##STR1## (wherein --X-- represents ##STR2## --Y-- represents ##STR3## and R.sup.1 and R.sup.2 represent a lower alkyl group) and a process for preparing the same.Type: GrantFiled: June 22, 1982Date of Patent: January 31, 1984Assignee: Otsuka Kagaku Yakuhin Kabushini KaishaInventors: Shigeru Torii, Hideo Tanaka, Mitsuo Akada, Tsunehiko Masatomi, Yasuo Shimizu
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Patent number: 4421933Abstract: Process for the co-production of ketones and mono-olefins from secondary alcohols and conjugated di-olefins in which dehydrogenation of the secondary alcohol and hydrogenation of the conjugated di-olefin are effected by contacting a mixture of the secondary alcohol and the conjugated di-olefin with a heterogeneous copper-containing catalytic system. The process is very useful for the co-production of methyl ethyl ketone and n-butenes from sec-butanol and butadiene at low temperatures (e.g. between 90.degree. C. and 130.degree. C.).Type: GrantFiled: July 2, 1982Date of Patent: December 20, 1983Assignee: Shell Oil CompanyInventors: Johannes A. M. Van Broekhoven, Christopher S. John
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Patent number: 4417076Abstract: A catalyst for dehydrogenation of oxygen-containing derivatives of the cyclohexane series of the general formula: ##STR1## wherein R.sub.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl;R.sub.2 and R.sub.3 are radicals having the same or different meanings: --H, --OH, .dbd.O, provided that R.sub.2 and R.sub.3 are not simultaneously hydrogen and R.sub.1, R.sub.2 and R.sub.3 are attached to different carbon atoms of the cycle,into corresponding cyclic ketones and/or phenols containing the following components, percent by weight:______________________________________ nickel 15 to 55 promotor-germanium and/or lead 0.2 to 8.0 inert carrier 84.8 to 37.0 ______________________________________and an atomic ratio of nickel to the promotor is within the range of from 15:1 to 410:1 respectively. The catalyst can additionally contain a salt of an alkali metal and a mineral acid in an amount of from 0.01 to 1.0% by weight.Type: GrantFiled: August 9, 1982Date of Patent: November 22, 1983Inventors: Alexandr Y. Rozovsky, Valentin D. Stytsenko, Svetlana A. Nizova, Petr S. Belov, Alexandr J. Dyakonov
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Patent number: 4415756Abstract: New bicyclo[2.2.2]oct-5-en-2-ones of the formulae Ia and Ib in the form of pure enantiomers and processes for preparing them are described. The compounds are used for the preparation of pure enantiomers of the formula V by sensitized photoreaction or of compounds of the formula VI by unsensitized photoreaction.Type: GrantFiled: December 2, 1981Date of Patent: November 15, 1983Assignee: Studiengesellschaft Kohle mbHInventors: Martin Demuth, Kurt Schaffner
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Patent number: 4415477Abstract: The herein-proposed catalyst for dehydrogenation oxygen-containing derivatives of the cyclohexane series having the following general formula ##STR1## where R.sub.1 is either hydrogen or alkyl C.sub.1 -C.sub.4,R.sub.2 and R.sub.3 are radicals having either the same or different values --H, --OH, .dbd.O, provided that R.sub.2 and R.sub.3 are not hydrogen atoms both at a time,R.sub.1, R.sub.2, R.sub.3 being linked to different carbon atoms of the ring to form the corresponding cyclic ketones and/or phenols, comprises the following components (wt. %):nickel--15 to 55tin--0.2 to 1.95inert carrier--84.8 to 43.05,while the atomic ratio of nickel and tin lies within 15:1 and 410:1, respectively, and may contain additionally an alkali salt of a mineral acid in an amount of 0.01 to 1.0 wt. %.Type: GrantFiled: December 22, 1980Date of Patent: November 15, 1983Inventors: Alexandr Y. Rozovsky, Valentin D. Stytsenko, Svetlana A. Nizova, Petr S. Belov, Alexandr J. Dyakonov
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Patent number: 4401823Abstract: Polyhydroxylated compounds such as glucose, sucrose, sorbitol, etc. are subjected to a hydrogenolysis reaction at hydrogenolysis conditions which include a temperature in the range of from about 175.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 2000 pounds per square inch in the presence of a catalytic composition of matter. The catalyst comprises a carbonaceous pyropolymer possessing recurring units containing at least carbon and hydrogen atoms which is impregnated with a transition metal. The products which are obtained will include alcohols, acids, ketones, ethers, and hydrocarbons.Type: GrantFiled: May 18, 1981Date of Patent: August 30, 1983Assignee: UOP Inc.Inventor: Blaise J. Arena
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Patent number: 4398043Abstract: A process for preparing cyclopentenolones of the formula: ##STR1## wherein R.sub.1 is a straight, branched or cyclic alkyl group having not more than 6 carbon atoms, a straight, branched or cyclic alkenyl group having not more than 6 carbon atoms, a straight or branched alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## wherein R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.Type: GrantFiled: November 23, 1981Date of Patent: August 9, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Yukihisa Takisawa, Hiroshi Yamachika
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Patent number: 4393245Abstract: New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.Type: GrantFiled: December 2, 1981Date of Patent: July 12, 1983Assignee: BASF AktiengesellschaftInventors: Werner Hoffman, Karl von Fraunberg, Manfred Baumann
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Patent number: 4390707Abstract: A method for the preparation of cyclopentenones of the general formula (VIII): ##STR1## wherein n is 5-7, has been developed which proceeds via the acid catalyzed deprotection and rearrangement of novel substituted-.alpha.-hydroxymethylfurans of general formula (VII): ##STR2## wherein R is a hydroxyl protecting group, R.sub.1 and R.sub.2 are methyl or ethyl or together form --(CH.sub.2).sub.3 -- and n is as above described. Cyclopentenones of formula VIII are useful intermediates in prostaglandin analog synthesis.Type: GrantFiled: February 2, 1982Date of Patent: June 28, 1983Assignee: American Cyanamid CompanyInventor: Steven L. Peake
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Patent number: 4380673Abstract: A secondary alcohol dissolved in a C.sub.12 to C.sub.20 paraffinic hydrocarbon substantially free of aromatics and of sulfur is dehydrogenated to the corresponding ketone at a temperature of 170.degree.-230.degree. C. in the presence of a catalyst of the Raney nickel type containing from 0.1 to 10% by weight of an additional metal consisting of copper, silver, gold, tin, lead, zinc, cadmium, indium or germanium, the ketone being preferably removed, as it is formed, from the reaction medium. A catalyst for use in the present process is provided.Type: GrantFiled: June 26, 1981Date of Patent: April 19, 1983Assignee: Institut Francais Du PetroleInventors: Jean-Paul Bournonville, Roger Snappe, Jean Miquel, Germain Martino
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Patent number: 4358409Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.Type: GrantFiled: April 16, 1980Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4356326Abstract: A process for producing 3-oxocyclopentenes which comprises treating a furan-carbinol of the formula: ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl group having not more than 6 carbon atoms, an alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom in an aqueous medium in the presence or absence of a catalyst at a pH of 3 to 6.5 to give the corresponding 3-oxocyclopentene of the formula: ##STR3## wherein R.sub.1 is as defined above.Type: GrantFiled: December 5, 1980Date of Patent: October 26, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4356127Abstract: A process for the preparation of a 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid derivative of the formula ##STR1## in which Z is acetyl, cyano, carbamoyl, alkoxycarbonyl or --COOZ.sup.1, andZ.sup.1 is a radical customary in the alcohol part of pyrethroids,comprising reacting an .alpha.-hydroxy-phosphonic acid ester of the formula ##STR2## in which R each independently is alkyl or phenyl, or the two radicals R togehter are alkanediyl,with a dichloromethane derivative of the formula ##STR3## in which R.sup.1 and R.sup.2 each independently is alkyl, phenyl, alkoxy or phenoxy, or together are alkanedioxy,in the presence of a base and at a temperature between about -100.degree. and +100.degree. C.Type: GrantFiled: July 2, 1980Date of Patent: October 26, 1982Assignee: Bayer AktiengesellschaftInventor: Hellmut Hoffmann
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Patent number: 4335262Abstract: Process for the preparation of muscone starting from pyranic derivatives by treatments thereof with hydrogen in an inert organic solvent and in the presence of a noble metal catalyst.Compound of formula ##STR1## and process for its preparation via dehydrogenation and dehydration of corresponding diol.Process for the preparation of unsaturated macrocyclic ketones of formula ##STR2## wherein the dotted lines stand for a single or a double bond wherein x=1 and y=2, orx=2 and y=1,starting from compound (Ia) via acidic treatment.Type: GrantFiled: September 3, 1980Date of Patent: June 15, 1982Assignee: Firmenich SAInventors: Karl H. Schulte-Elte, Joseph J. Becker, Walter Schenk
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Patent number: 4329508Abstract: A process for making mixed 2- and 3-C.sub.1 -C.sub.10 alkyl-2-cyclopenten-1-ones from a corresponding alkylcyclopentadiene by epoxidation to the oxiranes, hydrolysis to the diols, dehydration of the diols and rearrangement of the resulting mixed alkylcyclopentenones. The resulting product can be used to make methylcyclopentenolone, a synthetic maple flavor.Type: GrantFiled: September 29, 1980Date of Patent: May 11, 1982Assignee: SCM CorporationInventors: T. L. Ho, Shing-Hou Liu
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Patent number: 4328372Abstract: Ketal and hemiketal found in the reaction mass resulting from the acid catalyzed cleavage of cyclohexylbenzene hydroperoxide in the presence of alcohol are removed from the reaction mass resulting upon the acid catalyzed cleavage by separating an organic layer from said mass and treating said organic layer with an acid thus improving the yield of cyclohexanone, recovering alcohol and facilitating ensuing purification operations.Type: GrantFiled: June 27, 1979Date of Patent: May 4, 1982Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4324729Abstract: Novel acetylenic compounds useful as starting materials for the preparation of .beta.-damascenone. Process for their preparation and use thereof.Type: GrantFiled: October 17, 1980Date of Patent: April 13, 1982Assignee: Firmenich SAInventor: Peter Fankhauser
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Patent number: 4317935Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula: ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an -OH group.The thromboxane analogues are potent thrombotic agents, useful in cardiovascular treatment.Type: GrantFiled: October 6, 1980Date of Patent: March 2, 1982Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
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Patent number: 4310703Abstract: There is disclosed a process for preparing cyclohexanone by catalytic dehydrogenation of cyclohexanol, which comprises conducting the dehydrogenation in the presence of a copper-chromium catalyst derived from a mixture of copper oxide and chromium oxide having an atomic ratio of copper to chromium between 8:2 and 2:8, said mixture being subjected to heat treatment at a temperature of 650.degree. to 900.degree. C. in a non-reducing atmosphere and to subsequent reduction to provide the desired catalyst.Type: GrantFiled: July 17, 1980Date of Patent: January 12, 1982Assignee: Mitsubishi Chemical Industries LimitedInventors: Akio Tamaru, Yoshio Kinsho, Takayuki Yoshida
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Patent number: 4304943Abstract: Alkyl and aryl hydroxy compounds are converted to aldehydes, alcohols, and ketones in the presence of hydrogen using a catalyst comprised of the oxides of manganese, nickel and magnesium.Type: GrantFiled: August 8, 1979Date of Patent: December 8, 1981Assignee: Phillips Petroleum CompanyInventor: Geir Bjornson
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Patent number: 4299967Abstract: There is described a new process for the preparation of optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3 position, and derivatives thereof. A racemate of certain cyclobutanones is reacted with a sulfurous acid salt of an optically active base to obtain a mixture of diastereomeric 4-2-(2',2',2'-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts; this mixture is then separated into the pure diastereomeric sulfonic acid salts. Either the pure diastereomeric sulfonic acid salts are converted directly to the desired optically active products, or the optically active cyclobutanones obtained from the pure diastereomeric sulfonic acids salts by decomposition is converted, in the presence of a base to the desired product. Optionally, the product, optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids can be converted to their 1',2'-dibromo derivatives.Type: GrantFiled: December 17, 1979Date of Patent: November 10, 1981Assignee: Ciba-Geigy CorporationInventors: John G. Dingwall, Hans Greuter, Pierre Martin, Peter Ackermann, Laurenz Gsell
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Patent number: 4297517Abstract: A process for hydrolysing allylethers of the general formula:R.sub.6 CH.dbd.CR.sub.5 --CR.sub.4 --O--CR.sub.1 R.sub.2 R.sub.3wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6, which may be the same or different, represent a hydrogen atom or an alkyl group of from 1 to 8 carbon atoms or one of R.sub.1, R.sub.2 or R.sub.3 and R.sub.6 together represent a covalent bond, with water in the presence of a supported Group VIII metal catalyst. Methyl sec-butenyl ether can be hydrolysed in high yield to methyl ethyl ketone.Type: GrantFiled: July 31, 1980Date of Patent: October 27, 1981Assignee: Shell Oil CompanyInventors: Johannes A. M. Van Broekhoven, Eit Drent
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Patent number: 4296257Abstract: Cis- and trans-limonene oxides can be separated effectively one from the other by either fractional distillation or by substantially selectively rearranging with acid catalysis at mild temperature said cis-isomer into trans-dihydrocarvone. The distillatively-separated limonene oxide isomers or the remaining unreacted trans-limonene oxide isomer then is available for discrete conversion into a corresponding dihydrocarvone isomer with minimal equilibration by further acid-catalyzed rearranging at mild temperature.Type: GrantFiled: January 7, 1980Date of Patent: October 20, 1981Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia U. Din
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Patent number: 4282372Abstract: A novel process for producing cyclopentenolones, useful intermediates for producing agricultural chemicals and prostaglandins of the formula (I), ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl group, and R.sub.2 is a hydrogen atom, a lower alkyl, lower alkenyl or lower alkynyl group or a group of the formula, ##STR2## in which R.sub.4 is a hydrogen atom, a methyl group or a halogen atom), --CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.3 --CO.sub.2 R.sub.5, or --(CH.sub.2).sub.5 --CO.sub.2 R.sub.5 (in which R.sub.5 is a hydrogen atom or a lower alkyl group), but R.sub.1 and R.sub.2 are not a hydrogen atom at the same time, characterized in that said cyclopentenolones are derived from a starting material of the formula (III), ##STR3## through intermediates of the formulae (IV), (V) and (II), ##STR4## Many of the intermediates are novel compounds.Type: GrantFiled: October 30, 1979Date of Patent: August 4, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Matsuo, Kazunori Tsushima
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Patent number: 4281204Abstract: The present invention relates to substituted spirocyclic derivatives having the general formula: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond, wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are each the same or different, hydrogen or lower alkyl, wherein Z is one of the following: ##STR2## wherein R.sub.7 is either hydrogen or lower alkyl, wherein R.sub.8 and R.sub.9 are each lower alkyl; their methods of preparation and their use as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in the flavoring of foodstuffs and tobacco products.Type: GrantFiled: October 5, 1979Date of Patent: July 28, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
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Patent number: 4277625Abstract: New process for the preparation of muscone, a valuable macrocyclic musky perfume ingredient. The process makes use of an .alpha.,.omega.-dialdehyde as starting material.Type: GrantFiled: November 20, 1979Date of Patent: July 7, 1981Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Arnold Hauser, Gunther Ohloff
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Patent number: 4258268Abstract: At least one of a polycyclic phenol, a polycyclic alcohol and a polycyclic ketone is produced under hydrogenation conditions using a nickel oxide/manganese oxide/magnesium oxide catalyst by subjecting at least one of a monocyclic ketone, a monocyclic alcohol and a monocyclic phenol to said conditions and said catalyst.Type: GrantFiled: August 27, 1979Date of Patent: March 24, 1981Assignee: Phillips Petroleum CompanyInventor: Geir Bjornson
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Patent number: 4250341Abstract: The intermediate 2,2,6,6-tetrachloro (or tetrabromo) cyclohexanone is prepared by reacting chlorine (or bromine) with a cyclohexanol compound of the formula ##STR1## where each Y represents an atom of hydrogen or chlorine (or hydrogen or bromine) in the presence of, as catalyst, a certain organophosphorus compound.Type: GrantFiled: July 12, 1979Date of Patent: February 10, 1981Assignee: Fisons LimitedInventors: Brian J. Needham, John Miller
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Patent number: 4250332Abstract: Described is a process for preparing .beta.-damascone starting with 2,6,6-trimethyl cyclohex-2-enone according to the reaction sequence: ##STR1## wherein Z is hydrogen, MgX', Li, Na or K; Y is MgX', Li, Na or K; X' is Cl, Br or I; R is C.sub.1 -C.sub.3 lower alkyl such as methyl, ethyl, n-propyl or i-propyl; X is Cl, Br or I. Also described are the organoleptic uses of the compound having the structure: ##STR2## in augmenting or enhancing the taste or aroma of a consumable material, e.g., foodstuff, chewing gum, medicinal product, chewing tobacco, smoking tobacco, perfume, perfumed article (e.g., drier-added fabric softener articles and solid or liquid anionic, cationic or nonionic detergents) and cologne.Type: GrantFiled: October 26, 1979Date of Patent: February 10, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, John B. Hall, Robin Kasper, Manfred H. Vock, Ronald Schreck, Edward J. Granda, Joaquin F. Vinals
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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: 4204073Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.Type: GrantFiled: April 6, 1979Date of Patent: May 20, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Frank Kienzle