Reactant Contains -coo- Group Patents (Class 568/314)
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Patent number: 6417405Abstract: Substituted or unsubstituted cyclopentadienyl are prepared by reducing 4-ketocyclopentene to an alcohol, replacing the hydroxyl functionality with a leaving group and deprotonating the resulting product under base induced elimination conditions.Type: GrantFiled: June 20, 2001Date of Patent: July 9, 2002Assignee: The Dow Chemical CompanyInventor: Ravi B. Shankar
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Patent number: 6410795Abstract: A method for the preparation of 1,3-diketones is disclosed wherein the method comprises the steps of: (A) mixing an alkali metal base with a hindered alcohol in an aromatic hydrocarbon solvent; (B) boiling the mixture and azeotropically distilling water formed by the reaction between the base and the alcohol, whereby a solution of a hindered alkali metal alkoxide is formed in situ in the solvent; (C) mixing an ester with the solution of the hindered alkali metal alkoxide in the aromatic hydrocarbon solvent; and then (D) adding a ketone to the mixture.Type: GrantFiled: January 26, 2001Date of Patent: June 25, 2002Assignee: Crompton CorporationInventors: Michael H. Fisch, Edward Krainer, Radu Bacaloglu
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Patent number: 6372693Abstract: The invention relates to 2-(3-alkenylbenzoyl)cyclohexane-1,3-diones of the formula I where the variables have the following meanings: R1, R2 are hydrogen, nitro, halogen, cyano, thiocyanato, alkyl, haloalkyl, alkoxyalkyl, alkenyl, alkynyl, —OR6, —OCOR7, —OSO2R7, —SH, —S(O)nR8, —SO2OR6, —SO2NR6R9, —NR9SO2R7 or —NR9COR7; R3 is hydrogen, halogen, alkyl, haloalkyl, alkoxy, alkenyl, alkynyl; R4, R5 are hydrogen, nitro, halogen, cyano, thiocyanato, alkyl, haloalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, haloalkoxy, —COR10, —CO2R10, —COSR10, —CONR10R11, —C(R12)═NR13, —PO(OR10)(OR11); unsubstituted or substituted alkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl or hetarylalkyl; or R4 and R5 together form an alkanediyl chain which can be substituted and/or can be interrupted by a hetero atom; Q is an unsubstituted or substituted cyclohexane-1,3-dione ring whType: GrantFiled: November 2, 1999Date of Patent: April 16, 2002Assignee: BASF AktiengesellschaftInventors: Ernst Baumann, Wolfgang von Deyn, Stefan Engel, Regina Luise Hill, Uwe Kardorff, Guido Mayer, Martina Otten, Michael Rack, Joachim Rheinheimer, Matthias Witschel, Karl-Otto Westphalen, Ulf Misslitz, Helmut Walter
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Patent number: 6353139Abstract: A method for preparing ketones has advantages of improving yields and reducing the time of the reactions due to high efficiency of catalysts. Ketones are prepared by reacting an aliphatic or an aromatic aldehyde with a vinyl olefin having an aliphatic or aromatic alkyl moiety in the presence of a transition metal catalyst, 2-aminopyridine catalyst, a primary amine and an acid, as catalysts and additives.Type: GrantFiled: February 26, 2001Date of Patent: March 5, 2002Inventors: Chul Ho Jun, Dae Yon Lee, Hyuk Lee, Jun Bae Hong
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Patent number: 6310256Abstract: A process for forming 4-ketocyclopentene and substituted 4-ketocyclopentene compounds starting from the corresponding 1-carbohydrocarbyloxy-2-keto-4-hydroxy-5-cyclopentene by reduction followed by decarboxylation.Type: GrantFiled: November 19, 1999Date of Patent: October 30, 2001Assignee: The Dow Chemical CompanyInventors: Ravi B. Shankar, Francis J. Timmers
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Patent number: 6159988Abstract: Compounds of formula I, ##STR1## and the physiologically tolerable salts thereof, wherein the substituents R.sub.1 -R.sub.4 have the meanings given in the specifications and show an activity against inflammatory conditions.Type: GrantFiled: June 29, 1998Date of Patent: December 12, 2000Assignee: Hoeschst AktiengesellschaftInventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Ravishankar Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Bipin Alreja, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett, Kalpana Sanjay Joshi, Swati Bal-Tembe, Sadagopan Raghavan
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Patent number: 6143935Abstract: The condensation reaction of a ketone with either an ester or a carbonate to form, respectively, a 1,3-diketone or a .beta.-ketoester often affords poor results under the standard condensation reaction conditions. High yields and high purities of the desired product can be obtained by performing the reaction using an alkoxide base in DMSO as the sole solvent.Type: GrantFiled: June 2, 1998Date of Patent: November 7, 2000Assignee: Eastman Chemical CompanyInventors: Neil W. Boaz, M. Todd Coleman
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Patent number: 6011178Abstract: 2-Amino-4,5,3',4'-tetramethoxybenzophenone of the formula: ##STR1## is prepared by mononitration of 3,3',4,4'-tetramethyoxybenzophenone using nitric acid in the presence of acetic acid, and subsequent reduction of the nitro group. The compound is an intermediate in the synthesis of active ingredients against rheumatoid arthritis.Type: GrantFiled: March 12, 1999Date of Patent: January 4, 2000Assignee: Lonza, Ltd.Inventors: Oleg Werbitzky, Walter Brieden, Etienne Heinzmann
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Patent number: 5955635Abstract: An improved process for the preparation of Nabumetone, which comprises the following steps:a) condensation between 6-methoxy-naphthaldehyde I and t-butyl acetoacetate II, to give 3-t-butoxycarbonyl-4-(6'-methoxy-2'-naphthyl)-but-3-en-2-one III as an E/Z mixture;b) hydrogenation of III in the presence of a palladium catalyst, to give 3-t-butoxycarbonyl-4-(6'-methoxy-2-naphthyl)-butan-2-one IV;c) cleavage of the t-butyl ester by acid catalysis; andd) recrystallization of the crude with methanol.Type: GrantFiled: April 24, 1998Date of Patent: September 21, 1999Assignee: Secifarma S.P.A.Inventors: Walter Cabri, Domenico Magrone, Roberto Angelini, Erminio Oldani
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Patent number: 5936129Abstract: A process for making a sterically-hindered beta-diketone involving: (a) providing a solution comprising: (i) an ester; (ii) a base; and (iii) a solvent; (b) adding a ketone selected from the group consisting of an aromatic ketone and a hindered aliphatic ketone, to the solution, to form a condensation reaction mixture, whereby either the ester or the ketone is hindered; (c) reacting the solution with the ketone to form a sterically-hindered beta-diketone; and (d) recovering the sterically-hindered beta-diketone from the condensation reaction mixture.Type: GrantFiled: January 22, 1998Date of Patent: August 10, 1999Assignee: Henkel CorporationInventors: Kevin V. Martin, Phillip L. Mattison, Michael J. Virnig
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Patent number: 5925795Abstract: This invention relates to processes for the preparation of aryl-.beta.-diketones and aryl-pyrimidine ketones. In addition, this invention relates to the preparation of aryl-.beta.-triketones and dimethyl aminomethylene .beta.-diketones, which are useful as crop protection intermediates.Type: GrantFiled: September 16, 1996Date of Patent: July 20, 1999Assignee: Zeneca LimitedInventors: Raymond A. Felix, Hsiao-Ling M. Chin, Frank X. Woolard, David L. Lee
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Patent number: 5808165Abstract: The present invention is directed to compositions containing novel beta-diketones of formula (I) and formula (II),R.sub.1 COCH.sub.2 COR.sub.2 (I)R.sub.2 COCH.sub.2 COR.sub.2 (II)which may be used to stabilize various polymers, such as polyvinyl chlorides (PVCs). The present invention is also directed to a method for preparing .beta.-diketones by a Claisen condensation reaction, which is represented as follows:R.sub.4 COCHR.sub.5 H+R.sub.6 C(O)OR.sub.7 +RO.sup.- .fwdarw.?R.sub.4 COCR.sub.5 COR.sub.6 !-+R.sub.7 OH+ROH.Type: GrantFiled: May 25, 1995Date of Patent: September 15, 1998Assignee: Rhone-Poulenc ChimieInventors: Serge Chassaing, Michel Gay, Gilles Mur
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Patent number: 5763627Abstract: The invention relates to a novel process for simultaneously preparing cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones in the presence of a metal salt according to the scheme ##STR1## during the reaction, high-boiling poly (ethylene glycol) dialkyl ethers are then used. By introducing the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and adding further 3-acyltetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can, moreover, be recovered in a simple manner by washing with water.Type: GrantFiled: June 25, 1997Date of Patent: June 9, 1998Assignee: Huels AktiengesellschaftInventor: Manfred Kaufhold
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Patent number: 5750793Abstract: New process for the synthesis of the antiinflammatory drug known as nabumetone that consists in reacting 2-acetyl-5-bromo-6-methoxynaphthalene with an alkyl acetate in presence of an alkaline alcoholate to get 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one that by catalytic hydrogenation in a polar solvent and in presence of a base gives 4-(6-methoxy-2-naphthyl)butan-2-one known as nabumetone.Type: GrantFiled: January 23, 1997Date of Patent: May 12, 1998Assignee: Alfa Chemicals Italiana S.p.A.Inventors: Vincenzo Cannata, Amilcare Bertoni, Stefano Bianchi
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Patent number: 5618982Abstract: Ketones having at least one hydrogen atom or ester group in the .alpha.-position with respect to a ketonic carbonyl group thereof, for example cyclopentanone, 2-methylcyclopentanone and other substituted cyclopentanones, are effectively C- or .alpha.-alkylated, especially on an industrial scale, by reacting same with an alkylating agent in the presence of a catalytically effective amount of a condensed or uncondensed orthophosphate anion.Type: GrantFiled: November 22, 1994Date of Patent: April 8, 1997Assignee: Rhone-Poulenc ChimieInventors: Laurent Gilbert, Michel Spagnol
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Patent number: 5600008Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkoxybenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of arylhaloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.Type: GrantFiled: March 13, 1995Date of Patent: February 4, 1997Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Kindrick L. Leschinsky
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Patent number: 5600009Abstract: The palladium-catalyzed coupling of aryl and vinyl halides with vinylic compounds is disclosed. A preferred embodiment relating to the palladium catalyzed coupling of 4-substituted and 6-substituted-2-methoxynaphthalene to form nabumetone is also disclosed. The beauty of this novel reaction is that methylvinylketone, normally employed by the art directly as-is for the preparation of nabumetone, is formed in situ. We have discovered a mechanism to take advantage of the in situ formation of methylvinylketone, thus avoiding the use of expensive, toxic, and unstable methyl vinyl ketone feed. This reaction may be employed for a variety of pharmaceutically active and non-pharmaceutical compounds.Type: GrantFiled: April 9, 1996Date of Patent: February 4, 1997Assignee: Hoechst Celanese CorporationInventors: John F. Fritch, Mohammad Aslam, Dora E. Rios, Joel C. Smith
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Patent number: 5563297Abstract: The present invention relates to novel intermediates for the preparation of vitamin A and carotenoids, corresponding to the following formula (I): ##STR1## in which X is a carbon atom; n is equal to 1 or 2; R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms, alkenyl containing 2 to 11 carbon atoms or aryl, each alkyl and alkenyl may be linear, branched or cyclic, or R.sub.1 and R.sub.2 can together with the carbon atom to which they are attached form a cycloaliphatic compound which is optionally substituted; and R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms or alkenyl containing 2 to 10 carbon atoms, each alkyl or alkenyl being linear, or if containing sufficient numbers of carbon atoms, may also be branched or cyclic, or an aryl containing 6 to 10 carbon atoms, or any two of R.sub.4, R.sub.5, R.sub.6, R.Type: GrantFiled: October 7, 1994Date of Patent: October 8, 1996Assignee: Rhone-Poulenc Nutrition AnimaleInventor: Hugues Bienayme
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Patent number: 5550296Abstract: A liquid ammonia stream is mixed with a crude oil stream which contains naphthenic acids. Ammonium naphthenates are formed which are then separated from the crude oil with the ammonia. The naphthanates are converted back to acids by addition of acetic acid. Calcium hydroxide is added to form calcium naphthenates and the mixture is pyrolysized which produces ketones.Type: GrantFiled: December 2, 1994Date of Patent: August 27, 1996Assignee: Shell Oil CompanyInventor: Weston W. Haskell
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Patent number: 5545762Abstract: 1-cyclopropylalkane-1,3-diones are prepared by reacting a cyclopropyl alkyl ketone with a carboxylic ester in the presence of an alkali metal alcoholate, at temperatures of not more than 50.degree. C. in the presence of a solvent which is free of alcohol or contains only small quantities of alcohol.Type: GrantFiled: October 20, 1994Date of Patent: August 13, 1996Assignee: Huels AktiengesellschaftInventor: Jurgen Muhr
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Patent number: 5532416Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkylbenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of aryl-haloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.Type: GrantFiled: July 20, 1994Date of Patent: July 2, 1996Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Kindrick L. Leschinsky
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Patent number: 5489712Abstract: The present invention provides a novel process for preparing cyclic ketones, such as indanones, which comprises the steps of (a) subjecting a substituted ketone to suitable methylenation conditions in the presence of a methylene transfer agent and an acylating agent for a sufficient period of time and under suitable conditions of temperature and pressure to form the corresponding alpha, beta unsaturated ketone, and (b) subjecting said unsaturated ketone to suitable cyclization conditions in the presence of a suitable acid or base for a sufficient period of time and under suitable conditions of temperature and pressure to form said cyclic ketones.Type: GrantFiled: November 4, 1994Date of Patent: February 6, 1996Assignee: Hoechst Celanese CorporationInventor: Apurba Bhattacharya
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Patent number: 5484949Abstract: The present invention relates to a method for the synthesis of .alpha., .beta.-unsaturated ketones which comprises, in the method for the synthesis of .alpha., .beta.-unsaturated ketones represented by general formula ##STR1## reacting aldehydes represented by general formulaR.sup.1 CHO(where R.sup.1 is as defined above) with alkali metal salt of acetoacetic acid represented by general formula ##STR2## (where M.sup..sym. is an alkali metal ion), in the presence as a catalyst of 3-azabicyclo[3,2,2]nonane, a cyclic secondary amine represented by general formula (1) ##STR3## a cyclic secondary amine represented by general formula (2) ##STR4## (where, l is 1 or more and up to 6, a ring with N is a 6-membered, 7-membered or 8-membered ring, the two neighbors of N are methylene, R.sup.3 is a lower alkyl group, its substitution position is at a carbon atom other than two those adjacent to N, and ##STR5## is an alicyclic group or a phenol group), or a secondary amine represented by general formula (3)CH.sub.3 NHCH.Type: GrantFiled: March 2, 1994Date of Patent: January 16, 1996Assignee: Nippon Soda Co., Ltd.Inventors: Keiichi Tsukashima, Masashi Nakajima, deceased, Masayoshi Fujimaru, Kenji Suzuki
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Patent number: 5481029Abstract: A process for preparing ketones, for example CF.sub.3 C(O)CH.sub.3, CF.sub.3 C(O)CH.sub.2 C(O)CF.sub.3 and CF.sub.3 C(O)CF.sub.2 H, in which .beta.-ketoesters are transesterified and decarboxylated using a carboxylic acid, for example trifluoroacetic acid, in the presence of a catalyst, particularly an "onium" salt of a carboxylic acid or an effective amount of a proton-donating acid, preferably a sulfonic acid such as alkyl- or arylsulfonic acids, or a mineral acid. The process is advantageously carried out in the absence of water, so that no formation of acetals or hydrates occurs, and no dehydrating step is needed. The process is simple to carry out, and if transesterification is carried out with a sufficiently active carboxylic acid, for example with trifluoroacetic acid, the presence of an additional catalyst is unnecessary.Type: GrantFiled: April 26, 1994Date of Patent: January 2, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Johannes Eicher, Werner Rudolph, Kerstin Eichholz
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Patent number: 5457236Abstract: In a process for preparing betadiketones which comprises an alkaline condensation of an ester and an acetophenone in the presence of an alkaline catalyst in an inert organic solvent, the improvement comprising at least one of the following conditions:(i) adding the acetophenone to the reaction mixture in a time period sufficiently short whereby degradation products in the reaction mixture are minimized;(ii) at the completion of the reaction, adding additional solvent to rapidly decrease the temperature of the reaction product mixture.(iii) mixing the organic solvent phase with the aqueous acid phase in the acidification step for a time period sufficiently long whereby the concentration of alkali metal remaining in the organic solvent phase is substantially zero; and(iv) decreasing the time between the completion of the acetophenone addition step and the initiation of the acidification step.Type: GrantFiled: March 7, 1994Date of Patent: October 10, 1995Assignee: Henkel CorporationInventors: Leroy O. Krbechek, Mary I. Casey
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Patent number: 5430172Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.Type: GrantFiled: April 15, 1994Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
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Patent number: 5428174Abstract: .alpha.,.beta.-Unsaturated ketones of the general formula I ##STR1## where R is an organic radical, are prepared by reacting a corresponding aldehyde R--CHO with acetoacetic acid or one of its salts in the presence of an amine in a two-phase reaction mixture by a process in which the reaction is carried out at a pH of from 6 to 8 in the presence of a catalytic amount of a primary amine.Type: GrantFiled: August 5, 1991Date of Patent: June 27, 1995Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5426246Abstract: Disclosed are a catalyst for directly reducing a carboxylic acid, the catalyst comprising a tin compound and a ruthenium compound supported on a carrier, the catalyst being prepared by the steps of calcining the tin compound in the presence of oxygen after deposition of the tin compound alone on the carrier, and activating the obtained product after deposition of the ruthenium compound on said carrier, a process for preparing the catalyst, and a process for preparing an alcohol compound using the catalyst.Type: GrantFiled: July 26, 1994Date of Patent: June 20, 1995Assignee: Arakawa Chemical Industries, Ltd.Inventors: Eiji Nagahara, Yasushi Itoi
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Patent number: 5420364Abstract: Halogenated aromatic compounds are prepared by passing esters of halogenoformic acid at temperatures in the range 150.degree. to 600.degree. C. and pressures from 0.1 to 3 bar over a catalyst containing chromium, magnesium, iron, silicon and/or aluminium, wherein if Al.sub.2 O.sub.3 catalysts are used these have been activated with hydrogen halide.Type: GrantFiled: July 2, 1993Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Albrecht Marhold
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Patent number: 5359126Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.Type: GrantFiled: February 7, 1994Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventor: Charles A. McCombs
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Patent number: 5344992Abstract: There is disclosed a process for the preparation of 1,3-diketones of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.20 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, NO.sub.2, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, C.sub.7 -C.sub.9 phenylalkyl or a radical of formula II--A--X--R.sub.4 (II)whereinA is C.sub.1 -C.sub.12 alkylene, phenylene or phenylene which is substituted by halogen, hydroxy, NO.sub.2, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.12 alkylene which is substituted by hydroxy, halogen and/or alkoxy,X is oxygen or sulfur, andR.sub.4 is hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy,C.sub.1 -C.sub.4 alkyl, NO.sub.2 and/or C.sub.1 -C.sub.4 alkoxy, or is C.sub.7 -C.sub.9 phenylalkyl, andR.sub.3 is hydrogen, C.sub.1 -C.sub.20 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, C.sub.1 -C.sub.4 alkyl, NO.sub.2 and/or C.sub.1 -C.Type: GrantFiled: May 11, 1993Date of Patent: September 6, 1994Assignee: Ciba-Geigy CorporationInventors: Rolf Drewes, Hans-Helmut Friedrich, Hans-Ludwig Mehner, Bernd Braun, Walter Wecht
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Patent number: 5329054Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.Type: GrantFiled: July 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
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Patent number: 5274136Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordance with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: July 1, 1992Date of Patent: December 28, 1993Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr.
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Patent number: 5166365Abstract: A novel fluorine-containing aromatic compound of the formula: ##STR1## wherein X is ##STR2## in which R.sub.f is a perfluoroalkyl group having 1 to 10 carbon atoms,R.sub.f ' is a perfluoroalkyl group having 1 to 12 carbon atoms,p is an integer of 1 to 3,q is an integer of 0 to 3,r is 0 or 1,s is an integer of 0 to 5and t is an integer of 0 to 5,Y is X, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a fluoroalkyl group having 1 to 8 carbon atoms, andeach A is independently ##STR3## in which D is an amino, carboxyl, hydroxyl, methyl or haloformyl group, and n is an integer of 1 or 2, or ##STR4## can be used to derive various compounds, some of which are useful for preparing a fluorine-containing epoxy compound of polyimide with good properties.Type: GrantFiled: May 10, 1990Date of Patent: November 24, 1992Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Tsutomu Kobayashhi, Motonobu Kubo
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Patent number: 5136081Abstract: The invention provides a process for the preparation of fungicidally active cyclopentene derivatives of the general formula ##STR1## cyclopentane derivatives of the general formula ##STR2## and cyclohexane derivatives of the general formula ##STR3## in which n, R, R.sup.1, R.sup.2, R.sup.5, X and Y are as herein defined. Compounds of formula II and III are also provided which are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: September 11, 1989Date of Patent: August 4, 1992Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Paul H. Briner
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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: 5041613Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.Type: GrantFiled: August 28, 1989Date of Patent: August 20, 1991Assignee: Eastman Kodak CompanyInventor: Charles A. McCombs
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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: 5041681Abstract: Process for the preparation of herbicidally active substituted cyclohexan-1,3,5-triones which comprises either(a) reacting a compound of formula (II) ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are, for example, hydrogen or C.sub.1 -C.sub.4 alkyl with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.1 is optionally substituted aryl in the presence of a base and a Lewis acid; or(b) reacting a compound of formula (VI) ##STR2## with a compound of formula (X) ##STR3## in the presence of a Lewis acid; or (c) where R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same, reacting a compound of formula (XI) ##STR4## with a compound of formula R.sup.2 X' in the presence of a base, wherein X' is a leaving group.Type: GrantFiled: January 12, 1990Date of Patent: August 20, 1991Assignee: Imperial Chemical Industries PLCInventor: Glynn Mitchell
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Patent number: 5015777Abstract: A process for the preparation of aromatic beta-diketones by the reaction of an acetophenone and a molar excess of an alphatic ester or an ester of benzoic acid in the presence of sodium alkoxide condensation agent in an aromatic hydrocarbon solvent. Also disclosed is a method of recycling the solvent and excess ester reactant after separation of the aromatic beta-diketone product.Type: GrantFiled: November 2, 1989Date of Patent: May 14, 1991Assignee: Witco CorporationInventors: Daniel R. Chisolm, Richard A. Weiss, Leonid Rozov
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Patent number: 4950763Abstract: Ketones of the general formula (I) ##STR1## where R.sup.1 and R.sup.2 independently of one another are each alkyl, cycyloalkyl, arylalkyl, aryl or hetaryl, and one or more of the radicals R.sup.1 and R.sup.2 carry one or more hydrogen atoms on the .alpha.-carbon atom, are prepared by reacting two carboxylic acids of the general formulae (IIa/IIb), R.sup.1 --COOH (IIa) and R.sup.2 --COOH (IIb) or by reacting a carboxylic acid R.sup.1 --COOH (IIa) and a ketone ##STR2## or by reacting a mixture of IIa, IIb and Ib, in the gas phase in the presence of a catalyst, by a process in which a catalyst is used whose active material contains at least 50% by weight of titanium dioxide having a specific surface area greater than 10 m.sup.2 /g.0.Type: GrantFiled: July 18, 1989Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Charles Schommer, Klaus Ebel, Toni Dockner, Matthias Irgang, Wolfgang Hoelderich, Harald Rust
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Patent number: 4906658Abstract: Compounds of Formula I ##STR1## the pharmaceutically acceptable salts, and the gamma-lactone form thereof are described. They are antagonists of leukotrienes and SRS-A.Type: GrantFiled: April 21, 1987Date of Patent: March 6, 1990Assignee: Merck Frosst Canada, Inc.Inventors: Haydn W. R. Williams, Robert N. Young
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Patent number: 4885395Abstract: Alpha,beta-unsaturated ketones of the formula (I) ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, alkenyl of 1 to 12 carbon atoms, cycloalkyl, aryl, aralkyl or alkylaryl, are prepared by converting the corresponding .alpha.-hydroxy, alkoxy or carboxy compound in the presence of an acidic catalyst.Preferred starting materials are 3-methyl-3-hydroxy-butan-2-one, 3-methyl-3-hydroxypentan-2-one and 3-pentamethylene-3-hydroxypropan-2-one, and preferred catalysts are zeolites of the pentasil type.Type: GrantFiled: September 25, 1987Date of Patent: December 5, 1989Assignee: BASF AktiengsellschaftInventors: Wolfgang Hoelderich, Kurt Schneider, Leopold Hupfer
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Patent number: 4885396Abstract: A process for the preparation of 2-hydroxy-4-(2'-hydroxyethoxy)benzophenones, by reacting 2,4-dihydroxybenzophenones with ethylene carbonate in the presence of a quaternary ammonium salt catalyst at elevated temperatures, and isolating the finished product from the crude reaction mixture.Type: GrantFiled: May 20, 1988Date of Patent: December 5, 1989Assignee: BASF AktiengesellschaftInventors: Erwin Hahn, Peter Neumann
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Patent number: 4866210Abstract: Ketones of the formula ##STR1## where R.sup.1 to R.sup.3 are each hydrogen and R.sup.1 to R.sup.4 are each alkyl of 1 to 12 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, aryl, aralkyl or alkylaryl, which each in turn may be substituted, or R.sup.1 and R.sup.2 and R.sup.3 together with the carbon atoms to which they are bonded form a cycloalkane, are prepared by reacting ketones of the formula ##STR2## where one of R.sup.1, R.sup.2, R.sup.3 and R.sup.5 is hydroxyl, alkoxy or carboxyl while the remaining R.sup.1 to R.sup.4 have the abovementioned meanings, with hydrogen in the presence of acid catalysts supporting one or more hydrogenation components, zeolites of the pentasil type being particularly suitable.Type: GrantFiled: January 15, 1988Date of Patent: September 12, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Leopold Hupfer, Kurt Schneider
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Patent number: 4829091Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordane with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: May 27, 1987Date of Patent: May 9, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr
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Patent number: 4695673Abstract: An acylated 1,3-dicarbonyl compound is produced by rearrangement of the corresponding enol ester in the presence of a cyanide source. In one embodiment the cyanide source is employed with a molar excess of a moderate base, with respect to the enol ester. In another embodiment, the cyanide source is a stoichiometric amount, with respect to the enol ester, of potassium or lithium cyanide and a catalytic amount of a crown ether is used.Type: GrantFiled: June 9, 1986Date of Patent: September 22, 1987Assignee: Stauffer Chemical CompanyInventors: James B. Heather, Pamela D. Milano
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Patent number: 4562067Abstract: The new dibenzoylmethane derivatives of the formula ##STR1## in which R.sup.1 denotes hydrogen, methyl or ethyl andR.sup.2 denotes methyl or ethyl andR.sup.3 represents a straight-chain or branched lower alkyl radical,can be prepared by reacting acetophenone derivatives with an anisic ester or by reacting a substituted benzoic ester with p-methoxyacetophenone. The compounds can be used in sunscreen agents.Type: GrantFiled: January 12, 1984Date of Patent: December 31, 1985Assignee: Haarmann & Reimer GmbHInventors: Rudolf Hopp, Horst Finkelmeier, Roland Langner
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Patent number: 4560791Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: November 14, 1983Date of Patent: December 24, 1985Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Braja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: RE37813Abstract: New process for the synthesis of the antiinflammatory drug known as nabumetone that consists in reacting 2-acetyl-5-bromo-6-methoxynaphthalene with an alkyl acetate in presence of an alkaline alcoholate to get 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one that by catalytic hydrogenation in a polar solvent and in presence of a base gives 4-(6-methoxy-2-naphthyl)butan-2-one known as nabumetone.Type: GrantFiled: April 11, 2000Date of Patent: August 6, 2002Assignee: Honeywell International Inc.Inventors: Vincenzo Cannata, Amilcare Bertoni, Stefano Bianchi