Aldehyde Or Ketone Reactant Patents (Class 568/388)
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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: 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: 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: 5475162Abstract: A process of effecting an acid catalyzed reaction wherein a reactant capable of undergoing an acid catalyzed reaction is contacted with an acid functionalized organically-bridged polysilsesquioxane catalyst where all of the acid functionality is covalently bonded to the organic portion of an organically-bridged polysilsesquioxane framework has been developed. The acid functionalized organically-bridged polysilsesquioxane is formed by polymerizing a monomer through sol-gel processing to form an organically-bridged polysilsesquioxane, reacting an acid group onto the organic portion of the organically-bridged polysilsesquioxane, and recovering the acid functionalized product. An embodiment of the invention is where the acid catalyzed reaction is the hydration of olefins, alkylation, acylation, isomerization, or aldol condensation/elimination.Type: GrantFiled: July 19, 1994Date of Patent: December 12, 1995Assignee: UOPInventors: Timothy A. Brandvold, Jennifer S. Holmgren, Thomas P. Malloy
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Patent number: 5449801Abstract: A process for the selective high yield halogenation R--CH.sub.3 wherein R is ##STR1## Si(Cl).sub.m (CH.sub.3).sub.n, wherein m is 1 to 3, n is 1 to 3 and m+n is 3; phenyl; or phenyl substituted with Cl, Br, F, OR.sup.1, SR.sup.1 or NO.sub.2 ; R.sup.1 is C.sub.1 -C.sub.3 alkyl; and X is chlorine or bromine; under reactive distillation conditions which continuously and selectively separate the mono, di, or trihalogenated product from the reaction zone and which does not require recycling of the starting materials is disclosed.Type: GrantFiled: July 14, 1993Date of Patent: September 12, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Chris S. Barnum, Charles T. Blaisdell
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Patent number: 5410089Abstract: A process for preparing dihydroxyacetone by condensation, catalyzed by a thiazolium ylide, of formaldehyde, wherein the reaction is carried out in a system composed of an aqueous phase and at least one organic liquid phase.Type: GrantFiled: April 29, 1993Date of Patent: April 25, 1995Assignee: BASF AktiengesellschaftInventors: Eugen Gehrer, Wolfgang Harder, Herbert Vogel, Bernhard Knuth, Klaus Ebel, Carsten Groening
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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: 5300654Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.Type: GrantFiled: July 15, 1991Date of Patent: April 5, 1994Assignee: Nippon Soda Co., Ltd.Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
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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: 5202496Abstract: Magnesium/aluminum synthetic anionic clay catalysts are made by spray-drying a slurry of a Mg/Al synthetic clay, making a plasticized mixture of the spray-dried clay with diatomaceous earth, forming, drying and calcining the formed dried mixture. The catalyst is useful for making isophorone by the condensation of acetone.Type: GrantFiled: February 28, 1992Date of Patent: April 13, 1993Assignee: Aristech Chemical CorporationInventors: Alain A. Schutz, Leonard A. Cullo
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Patent number: 5166450Abstract: This invention relates to an improved process for the production of hydroxyketones, especially dihydroxyacetone, by the condensation of one or more aldehydes in the presence of a catalyst and the use of specific process train. The product of this process is a relatively pure and any waste products from the reaction are environmentally friendly because none of the chemical components are discharged into the waste streams.Type: GrantFiled: October 4, 1991Date of Patent: November 24, 1992Assignee: BP Chemicals LimitedInventors: Carl A. Avison, Ian D. Dobson, Benjamin P. Gracey, Barry Hudson, Thakor Kikabhai
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Patent number: 5162586Abstract: The conjugate addition of hydrocarbon equivalents to alpha,beta-unsaturated carbonyl compounds using a series of novel catalysts is described. The catalysts comprise copper(I) complexes with ligand systems comprising either tropocoronand macrocycles or N,N'-dialkylsubstituted aminotroponeimines.Type: GrantFiled: May 9, 1989Date of Patent: November 10, 1992Assignee: Massachusetts Institute of TechnologyInventors: Gilberto M. Villacorta, Kwang-Hyun Ahn, Stephen J. Lippard
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Patent number: 5159117Abstract: A process for preparing .alpha.,.alpha.-dialkoxy ketones of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.30 -cycloalkylakyl, C.sub.9 -C.sub.30 -alkylcycloalkyl, unsubstituted or C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy-, halogen-, C.sub.1 -C.sub.4 -haloalkyl-, C.sub.1 -C.sub.4 -haloalkoxy-, phenyl-, phenoxy-, halophenyl-, halophenoxy- and/or cyano-substituted aryl, C.sub.7 -C.sub.20 -aralkyl or heterocyclyl,R.sup.2 is also ##STR2## R.sup.3 and R.sup.4 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -arylalkyl, or together are an unsubstituted or C.sub.1-C.sub.4 -alkyl- substituted C.sub.2 -C.sub.7 -alkylene chain andR.sup.5 is R.sup.1 or together with R.sup.1 is an unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.2 -C.sub.Type: GrantFiled: August 20, 1991Date of Patent: October 27, 1992Assignee: BASF AktiengesellschaftInventors: Guenter Wegner, Stefan Karbach, Hubert Smuda, Eckhard Hickmann, Reiner Kober, Rainer Seele, Thomas Zierke
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Patent number: 5134238Abstract: Disclosed herein is a class of chiral copper-amine complexes of the formula R(L*) CuLi in which L* is selected from: ##STR1## In this formula, R is a transferable ligand, which can be alkyl, aryl or aralkyl. M is a metal ion such as Li, Na, K, Cs, Rb, Be, Mg and other metal ions from the first two columns of the periodic table. R.sub.1 is straight chain alkyl, R.sub.2 is aryl or substituted aryl and R.sub.3 and R.sub.4 form a heterocyclic ring or a substituted heterocyclic ring with 4 to 8 members including oxygen and sulfur.Such complexes react with .alpha.,.beta.-unsaturated ketones, aldehydes, esters and other carbonyl containing compounds such that R is transferred to the 3 position enantioselectively as shown below. ##STR2## Such complexes react with .alpha.,.beta.-unsaturated ketones in the presence of trialkysilyl halides to give silyl enol ether in which R is substituted in the 3 position as shown below.Type: GrantFiled: July 15, 1991Date of Patent: July 28, 1992Assignee: Brigham Young UniversityInventors: Bryant E. Rossiter, Masakatsu Eguchi
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Patent number: 5128488Abstract: The asymmetric hydrogenation of carbonyl compounds is carried out in the presence of at least one transition metal complex MZq(M=metal of group VIII of the Periodic Classication; Z=ligand selected among the atoms and the molecules which may complex the metal M; and q=degree of corrdination of M) and of at least one chiral phosphorous-containing ligand having formula (I), wherein R is hydrocarbonated radical (alkyl, cycloalkyl and aryl); R.sup.1 is H, hydrocarbonated radical or PR.sub.2 ; R.sup.2 is H or hydrocarbonated radical R.sup.3,R.sup.4, necessarily different, are H and optionally functionalized hydrocarbonated radicals; R.sup.5 and R.sup.6 are H and optionally functionalized hydrocarbonated radicals; one of the radicals R.sup.3 and R.sup.4 possibly carrying a function - OPR.sub.2 or NPR.sub.2, R.sup.5 and R.sup.6 being in this case H when R.sup.1 is PR.sub.2 ; R.sup.2 and R.sup.3 and the atoms of N and C which cary them respectively forming a heterocycle; or R.sup.2 and R.sup.Type: GrantFiled: April 27, 1990Date of Patent: July 7, 1992Assignee: Societe Chimique des Charbonnages S.A.Inventors: Andre Mortreux, Francis Petit
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Patent number: 5097089Abstract: This invention relates to a process for synthesis of glycerol from formaldehyde, wherein formaldehyde under substantially anhydrous condition is self-condensed in a catalytic step is dihydroxyacetone which is separated from the self-condensation catalyst and hydrogenated catalytically to glycerol.The feature of the invention is to have less than 0.4% w/w of water in the self-condensation reaction mixture thereby improving the process to produce glycerol in commercially viable rates and yields.Type: GrantFiled: March 27, 1990Date of Patent: March 17, 1992Assignee: BP Chemicals LimitedInventors: Benjamin P. Gracey, Barry Hudson, Peter S. Williams
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Patent number: 5087761Abstract: This invention relates to a process for condensing aldehydes to alpha-hydroxyketones in a liquid system containing an aldehyde and an active condensation catalyst formed by the abstraction of HX from a thiazolium salt in which X is the anion. The reaction is carried out in the absence of a base (other than the active catalyst) and the anion X. The catalyst is rendered free of the undesirable base and the anion X because these are the cause of premature deactivation of the catalyst.Type: GrantFiled: July 6, 1990Date of Patent: February 11, 1992Assignee: BP Chemicals LimitedInventor: Thakor Kikabhai
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Patent number: 5055620Abstract: Basic mixed oxides useful for base catalyzed reactions such as the aldol condensation of acetone and also useful as catalyst supports are made by mixing an acid such as nitric acid or acetic acid with a pseudoboehmite to form a gel, adding magnesium oxide or hydroxide, in a ratio of magnesium to aluminum of about 1:1 to about 10:1, agitating and heating for about 1 to 24 hours, and subsequently drying and calcining. The resulting polymorphic magnesium-aluminum oxide composition is hightly effective in the aldol condensation of acetone to isophorone, and other base catalyzed reactions such as isomerization of olefins, aldol condensation of aldehydes.Type: GrantFiled: September 4, 1990Date of Patent: October 8, 1991Assignee: Aristech Chemical CorporationInventor: Alain A. Schutz
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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: 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: 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: 4820858Abstract: The invention relates to a process for the preparation of 2-(hydroxyalkyl)acrylic compounds having the formula ##STR1## wherein X represents a --CN group, a --COOR.sub.3 group, a --COR.sub.4 group or a --CONR.sub.4 R.sub.5 group wherein R.sub.3 is an alkyl group containing 1-4 C atoms and R.sub.4 and R.sub.5 independently represent an H atom or R.sub.3, andwherein R.sub.1 and R.sub.2 independently represent an H atom or an alkyl group with 1-4 C atoms or an (hetero) aryl group, or R.sub.1 and R.sub.2 together represent a cyclic compound with 5-12 C atomsby contacting an acrylic compound H.sub.2 C.dbd.CH--X with a carbonyl compound of the formula ##STR2## wherein X, R.sub.1 and R.sub.2 denote the same as in the above, this being effected in the liquid phase in the presence of a tertiary amine, characterized in that the reaction is carried out at a pressure in excess of 500 bar in excess of 500 bar, advantageously 1,500-18,000 bar.Type: GrantFiled: March 18, 1988Date of Patent: April 11, 1989Assignee: Stamicarbon B.V.Inventors: Neil S. Isaacs, Jonathan Hill
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Patent number: 4782186Abstract: A liquid phase process for preparing alpha-hydroxyketones is provided. The process comprises condensing one or more aldehydes in the presence of a thiazolium salt and a sterically hindered base having a pKa value greater than 12.0. The sterically hindered base is preferably either an amidine or a secondary or tertiary alkoxide of an alkali metal.Type: GrantFiled: September 24, 1986Date of Patent: November 1, 1988Assignee: British Petroleum Company p.l.c.Inventor: Robert G. Beevor
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Patent number: 4769496Abstract: A process for producing higher ketones comprises the step of contacting under suitable conditions a feed comprising at least one C.sub.2 -C.sub.6 aliphatic aldehyde, and preferably also carbon monoxide, with a catalyst composition comprising (i) copper and/or an oxide thereof and (ii) zinc oxide. Preferably, the feed aldehyde is propanal, and the product comprises at least one C.sub.5 ketone. Ketones are substantially absent from the aldehyde feed.Type: GrantFiled: June 12, 1987Date of Patent: September 6, 1988Assignee: Phillips Petroleum CompanyInventors: David J. Elliott, Filippo Pennella
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Patent number: 4739122Abstract: A process to produce Methyl Amyl Ketone heterogeneously via the cross-aldol condensation reaction between a C.sub.3 (isopropanol or acetone feed) and a C.sub.4 (butanol or butyraldehyde feed). The catalyst, hydrogen reduced copper oxide on gamma alumina, produces both high reactivity and long catalyst lifetimes. The catalyst is successfully regenerated. Efficiencies to MAK range from 50 to 80 wt. % and efficiencies to useful products range from 75 to 95 wt. % depending on the composition of the feed and temperature. Temperatures range from 200.degree. to 262.degree. C.In general, this catalyst readily catalyzes the cross-aldol condensation reaction between aldehydes (or primary alcohols) and ketones (or secondary alcohols) to produce higher molecular weight ketones; likewise, this catalyst catalyzes the aldol condensation reaction between the same or different ketones to again produce higher molecular weight ketones.Type: GrantFiled: October 18, 1985Date of Patent: April 19, 1988Assignee: Union Carbide CorporationInventor: John B. Letts
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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: 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: 4670577Abstract: A novel process for the preparation of pent-4-enoic acids of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, cyano and alkoxycarbonyl of 2 to 5 carbon atoms and Y is selected from the group consisting of hydrogen, cyano, alkoxycarbonyl 2 to 5 carbon atoms, acyl of an organic carboxylic acid of 2 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with the proviso that X and Y are not both hydrogen comprising reacting a compound of the formula ##STR2## wherein R is selected from the group consisting of acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with an anion derivative of a compound of the formula ##STR3## wherein X.sub.1 and Y.sub.Type: GrantFiled: February 24, 1984Date of Patent: June 2, 1987Assignee: Roussel UclafInventors: Marc Julia, Therese Cuvigny
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Patent number: 4602117Abstract: A process for the preparation of halogenated 3,3-dimethyl-5-hexen-2-ones of the formula ##STR1## wherein an acetic acid ester of the formula ##STR2## is reacted with 2-methylbutan-3-one of the formula ##STR3##Type: GrantFiled: November 6, 1985Date of Patent: July 22, 1986Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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Patent number: 4575570Abstract: A process for producing alpha,beta-unsaturated ketones represented by the following general formula ##STR1## wherein R.sub.1 represents a hydrocarbon radical, R.sub.2 represents an organic radical bonded through a carbon-carbon bond, R.sub.3 and R.sub.4 represent a hydrogen atom or a hydrocarbon radical, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be straight-chained or form a ring in arbitrary combinations,which comprises contacting an alpha-disubstituted-beta-keto acid ester represented by the general formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined, and R.sub.5, R.sub.6, R.sub.7 and R.sub.8 represent a hydrogen atom or a hydrocarbon radical,with a catalyst consisting essentially of (a) a compound of a platinum-group metal and optionally (b) a monodentate ligand (b).Type: GrantFiled: July 31, 1984Date of Patent: March 11, 1986Assignee: Nippon Zeon Co., Ltd.Inventors: Hideaki Kataoka, Toshiro Yamada, Kuniaki Goto, Jiro Tsuji
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Patent number: 4570021Abstract: 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: March 25, 1985Date of Patent: February 11, 1986Assignee: SDS Biotech CorporationInventors: Richard L. Cryberg, Russell M. Bimber
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Patent number: 4567005Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of an iron, cobalt, nickel, ruthenium, rhodium, osmium, iridium or platinum catalyst.Type: GrantFiled: April 22, 1983Date of Patent: January 28, 1986Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4562296Abstract: One or more aldehydes or ketones, or both, are produced by pyrolyzing an alcohol having at least two carbon atoms or an aldehyde having at least two carbon atoms, or both, over a Group VIII metal oxide catalyst, preferably a catalyst composed predominantly of iron oxide, notably ferric oxide. Preferably, the catalyst additionally contains a minor proportion of a Group IV-A metal oxide, most preferably germanium dioxide. The process provides a good yield of lower molecular weight aldehydes, such as formaldehyde, or higher molecular weight ketones, such as acetone, 2-pentanone and the like. Selective manufacture of products enriched either in aldehyde or in ketone can be achieved by a simple adjustment in the reaction conditions employed.Type: GrantFiled: November 13, 1984Date of Patent: December 31, 1985Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4560802Abstract: 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: June 13, 1984Date 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: 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: 4536347Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.Type: GrantFiled: March 19, 1984Date of Patent: August 20, 1985Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang
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Patent number: 4535187Abstract: The aldol condensation of acetone to isophorone and mesityl oxides in high conversions and efficiencies is achieved by a catalyst comprising a calcined calcium salt deposited on an alumina support.Type: GrantFiled: December 21, 1983Date of Patent: August 13, 1985Assignee: Union Carbide CorporationInventors: Anthony J. Papa, Steven W. Kaiser
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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: 4496766Abstract: A process for producing an .alpha.,.beta.-unsaturated ketone of the general formula ##STR1## wherein R.sub.1 represents a hydrocarbon group, R.sub.2 represents an organic group bonded through a carbon-carbon bond, R.sub.3 and R.sub.4 represent a hydrogen atom or a hydrocarbon group, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be linear or may form a ring when taken together in arbitrary combinations,which comprises contacting an .alpha.-disubstituted-.beta.-keto acid ester of the general formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined, and R.sub.5, R.sub.6 and R.sub.7 represent a hydrogen atom or a hydrocarbon group,with a catalyst consisting essentially of (a) a compound of a platinum-group metal and (b) and .alpha.,.omega.-alkylenedi(disubstituted)phosphine.Type: GrantFiled: May 4, 1983Date of Patent: January 29, 1985Assignee: Nippon Zeon Co. Ltd.Inventors: Jiro Tsuji, Isao Shimizu
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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: 4476147Abstract: A process for augmenting or enhancing the aroma or taste of alliaceous flavors, particularly garlic flavors, by augmenting or enhancing the garlic and green aroma and taste nuances of alliaceous-flavored foodstuffs comprising the step of adding to a alliaceous-flavored foodstuff an aroma or taste augmenting quantity of a mixture of cis and trans isomers of a compound having the structure: ##STR1## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond.Type: GrantFiled: October 17, 1983Date of Patent: October 9, 1984Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, James M. Sanders, James N. Siano
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Patent number: 4465863Abstract: Described are compounds defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:(i) the sum total of carbon atoms in R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is three;(ii) when R.sub.7 is methyl, then R.sub.5 and R.sub.6 are both methyl, and(iii) when either R.sub.3 or R.sub.4 is methyl, then R.sub.7 is hydrogenand wherein R.sub.8 represents hydrogen, acetyl, alkoxyacyl, hydroxyacyl, or alkali metal carboxylate; and R.sub.9 is hydrogen or allyl with the additional proviso that R.sub.8 and R.sub.9 are not both hydrogen.Also described is the use of the subgenus of such compounds defined according to the structure: ##STR2## in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid nonionic, cationic, anionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and the like.Type: GrantFiled: November 12, 1982Date of Patent: August 14, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
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Patent number: 4412083Abstract: Described is a process for preparing solanone and norsolanadione using chemical intermediates defined according to the generic structure: ##STR1## wherein X is one of the moieties: ##STR2## wherein R represents hydrogen or methyl; wherein Y represents one of the structures: ##STR3## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; with the provisos that:(i) when Y is the moiety having the structure: ##STR4## then X is the moiety having the structure: ##STR5## (ii) when X is the moiety having the structure: ##STR6## then Y is the moiety having the structure:--C.tbd.N]In preparing solanone, the compound having the structure: ##STR7## or a mixture of compounds defined according to the structure: ##STR8## is reacted with methyl lithium and the resulting intermediate is hydrolyzed and the resulting compound is dehydrated.Type: GrantFiled: March 11, 1982Date of Patent: October 25, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, William L. Schreiber, Joseph A. McGhie, Ronald P. Schreck, Takao Yoshida, Loren B. Schreiber, Ranya Muralidhara
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Patent number: 4398044Abstract: Acetyl-tertiary-alkanes are prepared by hydrolytic decarboxylation of tertiary-alkanoylacetonitriles with hydrochloric acid.Type: GrantFiled: April 8, 1982Date of Patent: August 9, 1983Assignee: Eli Lilly and CompanyInventor: Riaz F. Abdulla
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Patent number: 4362670Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of a palladium catalyst.Type: GrantFiled: September 3, 1981Date of Patent: December 7, 1982Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4358619Abstract: The instant invention relates to an improved process for the production of formose from formaldehyde. The improvement resides in using relatively small quanities of basic lead compounds as catalysts for the condensation reaction of the formaldehyde and, at the same time, for controlling the pH-value. By following this technique, organic or inorganic bases which, hitherto, have normally been used for this purpose are no longer needed.Type: GrantFiled: February 22, 1979Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Ingo Stemmler, Hanns P. Muller, Kuno Wagner
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Patent number: 4355184Abstract: .alpha., .beta.-unsaturated-ketones are synthesized by reacting with an aldehyde and an alkali metal salt of acetoacetic acid in the presence of an aliphatic secondary amine in the mixture of heterogeneous solvents producing an oil layer and a water layer.Type: GrantFiled: April 27, 1981Date of Patent: October 19, 1982Assignee: Nippon Soda Company LimitedInventors: Tsutomu Kaku, Kiyoshi Katsuura, Mikio Sawaki
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Patent number: 4331814Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.Type: GrantFiled: February 1, 1973Date of Patent: May 25, 1982Assignee: Rhone Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4326086Abstract: This invention relates to an improved process for the preparation of formose by the condensation of aqueous formaldehyde. In the process according to this invention, tertiary amines which contain an electrophilic hetero atom in the .beta.-position to the tertiary nitrogen atom are used for controlling the pH instead of the inorganic bases which have previously been used for this purpose.Type: GrantFiled: August 17, 1978Date of Patent: April 20, 1982Assignee: Bayer AktiengesellschaftInventors: Edgar Mohring, Hanns P. Muller, Kuno Wagner