Aldehyde Reacted With Ketone Patents (Class 568/313)
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Patent number: 5214151Abstract: The present invention relates to a method for the preparation of .alpha., .beta.-unsaturated ketones represented by general formula (II) ##STR1## (where R is a heterocyclic group with nitrogen atom in the ring or a phenyl group with electron donative substituents) which comprises reacting aldehydes represented by general formula (I)RCHO (I)(where R is a s defined above) with acetone, in the presence as a catalyst of one or tow or more compounds selected from the group consisting of perhydroisoindole and pyrrolidine which may have substituents, in a water solvent, at 20.degree. C. to 40.degree. C., and then reacting at the reflux temperature.The compound (II) is extremely important as an intermediate for pharmaceuticals and agricultural chemicals.Type: GrantFiled: July 15, 1991Date of Patent: May 25, 1993Assignee: Nippon Soda Co., Ltd.Inventors: Masashi Nakajima, Tadashi Kyotani, Keiichi Tsukashima
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Patent number: 5202495Abstract: A process for the preparation of the compound of formula (I), 3-(6'methoxy-2'-naphthylmethyl)-2,4-pentanedione, ##STR1## comprises the calalytic hydrogenation of a compound of formula (II): ##STR2##Type: GrantFiled: October 10, 1990Date of Patent: April 13, 1993Inventor: Sidney E. Callander
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Patent number: 5177222Abstract: 1,1-Dialkoxy-2-oxo-6-aryl-3,5-alkadienes of the general formula I ##STR1## where Ar is a phenyl, biphenyl or naphthyl radical which may be substituted by one, two or three C.sub.1 -C.sub.4 -alkyl groups, C.sub.1 -C.sub.4 -alkoxy groups, hydroxyl groups, phenoxy groups, amino groups which may be mono- or di-C.sub.1 -C.sub.4 -alkyl-substituted, halogen atoms or a methylenedioxy group, the substituents being identical or different,R.sup.1 is hydrogen or C.sub.1 -C.sub.8 -alkyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.10 -alkoxycarbonyl or C.sub.1 -C.sub.10 -acyl,the radicals R.sup.3 are C.sub.1 -C.sub.8 -alkyl groups which may be bonded to one another with formation of a five-membered or six-membered ring andR.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, are used as sunscreen agents in cosmetic preparations.Type: GrantFiled: November 5, 1990Date of Patent: January 5, 1993Assignee: BASF AktiengesellschaftInventors: Helmut Guembel, Joachim Paust, Karin Sperling-Vietmeier, Rainer Becker
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Patent number: 5072050Abstract: Mono-, di- and tri-ketones of polyoxyalkylene compounds prepared by a method whereby the terminal hydroxyl groups of polyoxyalkylene compounds are oxidized to ketone groups with an alkali metal or an alkaline earth metal hypochlorite oxidant in the presence of acetic acid are disclosed. These compounds are useful for preparing surface active agents or they may be reacted with amines to provide fuel additives.Type: GrantFiled: October 9, 1990Date of Patent: December 10, 1991Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis, John M. Larkin
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Patent number: 5041604Abstract: A process for producing a high quality di(aryloxy)alkane with a high yield by the use of readily commercially available materials, without using any particular solvent or agent and by means of a simple operation and a general apparatus is provided, which process comprises subjecting a halogenated alkane of the formula (II)X--A--Y (II)wherein X and Y each represent a halogen atom and A represents a lower alkylene group, and a phenol of the formula (III) ##STR1## wherein R.sub.1 to R.sub.5 each are same or different, represent hydrogen, halogen, lower alkyl, lower alkoxy, carboxylic acid salt, acyl or nitro group, and may form a ring in conjunction of two adjacent groups,to condensation reaction in the presence of an alkali in an aqueous medium to form a di(aryloxy)alkane of the formula (I) ##STR2## and is characterized (i) by carrying out the condensation reaction in a molar ratio of the compound of the formula (II): the phenol of the formula (III): the alkali in terms of monovalent base of 1:1.5 to 3.0:1.Type: GrantFiled: June 20, 1990Date of Patent: August 20, 1991Assignee: Sanko Kaihatsu Kagaku KenkyushoInventors: Toranosuke Saito, Masakatu Kitani, Takashi Ishibashi
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Patent number: 5026919Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.Type: GrantFiled: December 20, 1985Date of Patent: June 25, 1991Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 5004839Abstract: Unsaturated ketones are produced from ketones and paraformadehyde under mild reaction conditions utilizing a catalyst comprising a halogen acid salt of a secondary amine and a nonsoluble solid oxide of an element selected from groups IB, IIIA, IVA, IVB, VA, VB, VIB and VIII of the periodic table. Temperatures of 120-150 and pressures of 700-1200 kpa are preferred; by-products may include di-unsaturated ketones such as divinyl ketone. Unsaturated ketones such as methyl vinyl ketone are useful in imparting ultraviolet sensitivity to plastics which enhances degradability.Type: GrantFiled: April 13, 1990Date of Patent: April 2, 1991Assignee: Aristech Chemical CorporationInventors: Joseph Pugach, Jeffrey S. Salek
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4956505Abstract: 4,4-Dimethyl-1-(p-chlorophenyl)pentan-3-one can be prepared by condensation of pinacolone and p-chlorobenzaldehyde in an alcohol as solvent in the presence of an inorganic base and by subsequent hydrogenation, in which the reaction mixture obtained in the condensation is hydrogenated directly without isolation of the intermediate 4,4-dimethyl-1-(p-chlorophenyl)-1-penten-3-one after the addition of a hydrogenation catalyst at elevated temperature and superatmospheric pressure to give 4,4-dimethyl-1-(p-chlorophenyl)pentan-3-one, after the hydrogenation catalyst has been separated off from the liquid hydrogenation mixture, the alcohol is largely distilled off, and the water content of the bottom product of the distillation is adjusted in such a manner that it separates into an aqueous and an organic phase, and the 4,4-dimethyl-1-(p-chlorophenyl)pentan-3-one is recovered from the organic phase.Type: GrantFiled: July 5, 1989Date of Patent: September 11, 1990Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege, Karl-Wilhelm Henneke
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Patent number: 4945184Abstract: Unsaturated ketones are produced from ketones and paraformaldehyde under mild reaction conditions utilizing a catalyst comprising a halogen acid salt of a secondary amine and a small amount of a carboxylic acid.Temperatures of 120.degree.-150.degree. C. and pressures of 775-1135 kilopascals are preferred. Di-unsaturated ketones such as divinyl ketone may also be produced; if the starting ketone already has an unsaturated group, a second unsaturated group will be produced.Type: GrantFiled: June 19, 1989Date of Patent: July 31, 1990Assignee: Aristech Chemical CorporationInventors: Joseph Pugach, Jeffrey S. Salek
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Patent number: 4908481Abstract: A simple process for preparing 1-(4-hydroxy-phenyl)-butan-3-one, a sought-after natural aromatic, in a pure form and in good yield from easily accessible starting materials, wherein a 4-tert-alkoxy-benzaldehyde is condensed, under alkaline conditions, to give a novel 1-(4-tert.-alkoxy-phenyl)-but-1-en-3-one, the latter is hydrogenated, during or after this condensation, to give a novel 1-(4-tert.-alkoxy-phenyl)-butan-3-one, and isobutene or 2-methyl-but-1(2)-ene is eliminated from this compound in the presence of a catalytic amount of an acid. The novel intermediates have the general formula ##STR1## where R is H or CH.sub.3 and the broken line may or may not be an additional carbon-carbon bond.Type: GrantFiled: November 18, 1985Date of Patent: March 13, 1990Assignee: BASF AktiengesellschaftInventors: Werner Hoffmann, Dieter Degner
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Patent number: 4761503Abstract: This invention relates to pharmaceutical compositions containing a class of 5-phenyl-1,3-dioxoalkenyl compounds useful as inhibitors of leukotriene biosynthesis and thus useful in the treatment of conditions associated with leukotrienes. This invention also relates to the use of the 5-phenyl-1,3-dioxoalkenyl compounds in the inhibition of leukotriene biosynthesis and thus in the treatment of conditions associated with leukotrienes. This invention further relates to a novel process for the preparation of the 5-phenyl-1,3-dioxoalkenyl compounds.Type: GrantFiled: November 7, 1986Date of Patent: August 2, 1988Assignee: G. D. Searle & Co.Inventors: Richard A. Partis, Richard A. Mueller
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Patent number: 4749804Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: June 10, 1986Date of Patent: June 7, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: George C. Schloemer
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Patent number: 4704479Abstract: Methylol ketones are produced by reacting a ketone with an aldehyde in the presence of a tertiary amine catalyst. The resulting polyols undergo the reactions common to beta hydroxy ketones, specifically, condensation reactions and substitution reactions involving the hydroxyl functionality; and addition reactions involving the carbonyl group. Each polyol molecule of the invention has from one to six hydroxyl groups in the beta position relative to the carbonyl group. The polyols are further characterized by complete water solubility and compatibility with a wide range of polymers, rendering these polyols useful as extenders and co-reactants.Type: GrantFiled: September 30, 1982Date of Patent: November 3, 1987Assignee: BTL Inc.Inventors: Paul R. Warnes, James T. Henderson, John P. Leja
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Patent number: 4704478Abstract: Two ketone molecules (which can be the same or different) can be condensed together in the presence of hydrogen to produce a higher ketone by contacting the materials to be condensed with a hydrogenation catalyst and with a non-zeolitic molecular sieve, which has in its calcined form an adsorption of isobutane of at least about 2 percent by weight of the non-zeolitic molecular sieve at a partial pressure of 500 torr and a temperature of 20.degree. C. One or both ketones may be generated in situ by dehydrogenation of an alcohol. The non-zeolitic molecular sieves can achieve improved conversions and selectivities as compared with most conventional catalysts for the reaction.Type: GrantFiled: June 25, 1986Date of Patent: November 3, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
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Patent number: 4599457Abstract: An improvement in the process for preparing hydroxyarylaldehydes is disclosed where a phenolic compound is reacted with formaldehyde, in the presence of a catalyst such as a titanium or zirconium containing catalyst, optionally in the presence of a catalyst promoter, wherein the improvement is the addition of a yield effective amount of a modifier having the formula: ##STR1## where R.sub.1 is selected from the group consisting of: an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group that can have 5 and 6 carbon atoms, and an H, and where R.sub.2 is selected from the group consisting of: an alkyl group having from 1 to 12 carbon atoms, and a cyclo alkyl group that can have 5 to 6 carbon atoms; and where R.sub.1 and R.sub.2 can together form a cyclic group that can have 5 and 6 carbon atoms.Type: GrantFiled: March 20, 1985Date of Patent: July 8, 1986Assignee: Henkel CorporationInventors: Phillip L. Mattison, LeRoy Krbechek
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Patent number: 4528400Abstract: Disclosed is a method for the preparation of ketones by a catalytic vapor phase reaction of using reactants such as ketones with carboxylic acids and/or carboxylic acid precursors. An example of such a reaction is that of acetone with pivalic acid over a ceria-alumina catalyst at a temperature of nearly 470.degree. C. to produce pinacolone.Type: GrantFiled: November 20, 1981Date of Patent: July 9, 1985Assignee: SDS Biotech CorporationInventors: Richard L. Cryberg, Russell M. Bimber
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Patent number: 4521629Abstract: The invention relates to a method for the preparation of certain substituted bis-arylpentadienones which are useful and valuable intermediates for the preparation of insecticidal amidinohydrazones. The invention further relates to pentadienone substituted amidimohydrazone insecticides and fire ant control agents.Type: GrantFiled: June 29, 1984Date of Patent: June 4, 1985Assignee: American Cyanamid CompanyInventors: Nicholas A. Cortese, Jr., William H. Gastrock
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Patent number: 4476324Abstract: Heat treated anionic clay mineral is an improved catalyst for the conversion of acetone to mesityl oxide and isophorone as well as for the aldol condensation of other carbonyl-containing compounds.Type: GrantFiled: June 2, 1982Date of Patent: October 9, 1984Assignee: Union Carbide CorporationInventor: Walter T. Reichle
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Patent number: 4399075Abstract: Phenoxytoluene derivative is chlorinated in a very high yield and selectivity in the presence of nitrogen-, sulfur-, phosphorus- or oxygen-containing compound which is capable of forming a charge-transfer complex with chlorine, chlorine radical or organic halogen compound, together with radical initiator and organic halogen compound.Type: GrantFiled: June 25, 1981Date of Patent: August 16, 1983Assignee: Asahi Chemical Company, LimitedInventors: Zenichi Yoshida, Susumu Kato, Takuya Fujiki, Yasuhiro Amemiya
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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: 4374274Abstract: A process for the preparation of .alpha.-methylsubstituted ketones by reacting the corresponding non-methylsubstituted ketones with formaldehyde under hydrogenating conditions. The reaction proceeds easily and with good yields if a catalyst containing metallic palladium deposited on a zirconium, hafnium, titanium or tin phosphate is used. The products are valuable intermediates for the preparation of dyes, crop protection agents or drugs.Type: GrantFiled: September 11, 1980Date of Patent: February 15, 1983Assignee: BASF AktiengesellschaftInventors: Gerd Heilen, Klaus Halbritter, Walter Gramlich
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Patent number: 4348508Abstract: Substituted Spirobi[2H-1-benzopyrans] particularly suitable for use as precursors to stable colored pyrylium salts are disclosed.Type: GrantFiled: June 25, 1981Date of Patent: September 7, 1982Assignee: Armstrong World Industries, Inc.Inventors: John E. Herweh, Thomas B. Garrett, Alan B. Magnusson
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Patent number: 4315032Abstract: A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.Type: GrantFiled: May 14, 1980Date of Patent: February 9, 1982Assignee: Teitin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
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Patent number: 4290974Abstract: The invention relates to oxybenzylidenebornanones which correspond to the general formula: ##STR1## in which Z and Z' denote hydrogen or a radical SO.sub.3 H, at least one of the two radicals Z and Z' denoting hydrogen, R.sub.1 denotes hydrogen, an alkyl radical having 2 to 18 carbon atoms, an alkenyl radical having 3 to 18 carbon atoms, a radical --(CH.sub.2 CH.sub.2 O).sub.n H, ##STR2## --(CH.sub.2).sub.m CO.sub.2 R, in which R denotes H or an alkyl radical, --(CH.sub.2).sub.3 SO.sub.3 H or a divalent radical --(CH.sub.2).sub.m or --CH.sub.2 --CHOH--CH.sub.2, m having the values 1 to 10, n having the values 1 to 20 and p having the values 1 to 6, and R.sub.3 and R.sub.4 representing hydrogen or an optionally branched or hydroxylic alkyl radical, or forming an aminoaliphatic heterocyclic ring with the nitrogen atom, R.sub.2 denotes a hydrogen atom, an alkoxy radical or a divalent radical --O-- bonded to the radical R.sub.1 if the latter is also divalent, and q denotes 1 or 2; if q has the value 2, R.sub.Type: GrantFiled: July 10, 1979Date of Patent: September 22, 1981Assignee: L'OrealInventors: Claude Bouillon, Charles Vayssie
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Patent number: 4271319Abstract: The present invention relates to a novel organic compound, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, and(c) converting the epoxide to a chlorohydrin, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone.Type: GrantFiled: May 14, 1979Date of Patent: June 2, 1981Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4263212Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.Type: GrantFiled: February 14, 1980Date of Patent: April 21, 1981Assignee: Rikagaku KenkyushoInventors: Pangbu Hong, Hiroshi Yamazaki
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Patent number: 4243683Abstract: Tertiary alcohols of the formula: ##STR1## wherein Y.sup.1 represents a carbonyl or hydroxymethylene group, and either(i) A.sup.1 represents a direct bond and R.sup.1 represents a phenyl group which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, or(ii) A.sup.1 represents a straight- or branched-chain alkylene group containing from 1 to 10 carbon atoms and R.sup.1 represents a hydrogen atom, or a phenyl, phenoxy or phenylthio group each of which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, are new compounds of use in the field of mammalian reproduction and also of use in the control of insects and acarines.Type: GrantFiled: October 3, 1978Date of Patent: January 6, 1981Assignee: May & Baker LimitedInventors: Barbara J. Broughton, Michael P. L. Caton, David J. Hambling
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Patent number: 4239657Abstract: Aldehydes or ketones of not less than 4 or 5 carbon atoms, respectively, are manufactured in a one stage process in the liquid phase by subjecting aldehydes and/or ketones of not less than 2 or 3 carbon atoms, respectively, to an aldol condensation and hydrogenating the resulting olefinically unsaturated aldehyde, the catalyst used for the aldol condensation and hydrogenation containing nickel or cobalt or their mixtures, zinc oxide and at least one of the elements iron, arsenic, antimony, bismuth, gallium, indium, thallium, germanium, tin, lead, cadmium and mercury or compounds of the said elements.Type: GrantFiled: February 12, 1979Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Gerd Heiien, Ekkehard Sapper, Werner Fliege, Arnold Wittwer
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Patent number: 4229378Abstract: The present invention provides a novel process for the production of 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone. The process comprises the steps of:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide,(c) converting the epoxide to a chlorohydrin,(d) catalytic hydrogenolysis of the chlorohydrin to produce a diol and subsequently converting the diol into the corresponding alcohol, and(e) oxidizing the alcohol to produce 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone.Type: GrantFiled: May 14, 1979Date of Patent: October 21, 1980Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4218468Abstract: There are provided insecticidal ketones having the general structure: ##STR1## insecticidal compositions containing the ketones and a carrier, and the method of controlling insects with the ketones.Type: GrantFiled: November 13, 1978Date of Patent: August 19, 1980Assignee: Mobil Oil CorporationInventor: Jill H. Paul
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Patent number: 4212825Abstract: Aldehydes or ketones of not less than 4 or 5 carbon atoms, respectively, are manufactured in a one stage process in the liquid phase by subjecting aldehydes and/or ketones of not less than 2 or 3 carbon atoms, respectively, to an aldol condensation and hydrogenating the resulting olefinically unsaturated aldehyde, the catalyst used for the aldol condensation and hydrogenation containing a mixture of nickel and cobalt, zinc oxide and at least one of the elements iron, arsenic, antimony, bismuth, gallium, indium, thallium, germanium, tin, lead, cadmium and mercury or compounds of the said elements.Type: GrantFiled: November 16, 1977Date of Patent: July 15, 1980Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Gerd Heilen, Ekkehard Sapper, Werner Fliege, Arnold Wittwer