Aldehyde Reacted With Ketone Patents (Class 568/390)
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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: 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: 4874900Abstract: A process is provided for the preparation of pseudoionones by the condensation reaction of citral with a ketone in the presence of lithium hydroxide catalyst.Type: GrantFiled: June 16, 1987Date of Patent: October 17, 1989Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 4806670Abstract: .beta.-Dicarbonyl and .beta.-cyanocarbonyl compounds ##STR1## where R.sup.1 is alkyl of 1-20 carbons, X is --COR.sup.2, Y is --COOR.sup.3, --COR.sup.3 or --CN, and R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.10 -alkyl, are prepared from R.sup.1 --CHO (II) and X--CH.sub.2 --Y (III) by reaction in the presence of a condensation catalyst, hydrogen and a hydrogenation catalyst, using an oxide or phosphate of Mg, Al, Ti, Zn or a rare earth metal as the condensation catalyst.Type: GrantFiled: May 4, 1987Date of Patent: February 21, 1989Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Klaus Halbritter, Gerd Heilen
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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: 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: 4701562Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.Type: GrantFiled: June 25, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
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Patent number: 4694108Abstract: A process of producing higher ketones comprises the step of contacting under suitable conditions a feed comprising (a) at least one C.sub.3 -C.sub.6 aliphatic ketone, (b) at least one C.sub.2 -C.sub.6 aliphatic aldehyde and, preferably, also (c) carbon monoxide with a catalyst composition comprising (i) copper or an oxide thereof and (ii) zinc oxide. Preferably, the feed ketone is methyl ethyl ketone, the feed aldehyde is propanal, and the product comprises at least one C.sub.7 ketone.Type: GrantFiled: August 1, 1986Date of Patent: September 15, 1987Assignee: Phillips Petroleum CompanyInventor: David J. Elliott
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Patent number: 4684743Abstract: .beta.-Dicarbonyl, .beta.-cyanocarbonyl and .beta.-dicyano compounds I ##STR1## where R.sup.1 is an organic radical, X and Y are COOR.sup.2, --CO--R.sup.2 or --CN and R.sup.2 is an organic radical, are prepared from R.sup.1 --CHO (II) and X--CH.sub.2 --Y (III) by reaction in the presence of a condensation catalyst, hydrogen and a hydrogenation catalyst, using an oxide or phosphate of Mg, Al, Ti, Zn or a rare earth metal as the condensation catalyst.Type: GrantFiled: October 1, 1985Date of Patent: August 4, 1987Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Klaus Halbritter, Gerd Heilen
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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: 4517385Abstract: Described is a process for preparing solanone and norsolanadione, both useful as tobacco flavorants.Type: GrantFiled: July 31, 1984Date of Patent: May 14, 1985Assignee: 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: 4480132Abstract: Disclosed is a process for the preparation of .alpha.,.beta.-unsaturated ketones containing a 2-oxopropylidene moiety by the reaction of an aldehyde with a 2,2-dialkyl-4-methyl-6-keto-1,3-dioxene in the presence of a catalytic amount of certain metallic halides.Type: GrantFiled: November 21, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: William T. Brown, Robert M. Simons
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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: 4449008Abstract: Described is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; wherein R.sub.4 represents methyl or ethyl; wherein one of R.sub.1, R.sub.2 and R.sub.3 represents 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:(i) when the dashed line at the 3-4 position is a double bond, then R.sub.3 is hydrogen or 2-methyl-1-propenyl;(ii) when the dashed line at the 2-3 position is a double bond, then R.sub.2 is hydrogen or 2-methyl-1-propenyl;(iii) when R.sub.4 is ethyl, then R.sub.2 is methyl and the double bond is at the 2-3 position; and(iv) when R.sub.4 is methyl, then R.sub.2 is hydrogen; 2-methyl-1-propenyl or 2-methyl-1-propylidenyl;with the members of said genus being novel compounds when R.sub.4 is ethyl or when R.sub.Type: GrantFiled: May 5, 1983Date of Patent: May 15, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Philip T. Klemarczyk, Lambert Dekker, Jacob Kiwala
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Patent number: 4431844Abstract: An improved process for the preparation of unsaturated ketones of the general formula I ##STR1## where R.sup.1 is --CH.sub.3, ##STR2## and R.sup.2 and R.sup.3 are different and each is H or --CH.sub.3, by reacting an aldehyde of the general formula II ##STR3## with a molar excess of acetone or methyl ethyl ketone at an elevated temperature in the presence of an aqueous alkali metal hydroxide solution, wherein (a) all the reactants are mixed thoroughly, (b) the temperature is kept at from 10 to 120.degree. C. above the boiling point of the lowest-boiling component and (c) the pressure is kept at from p to 100 bar, where p is the vapor pressure of the mixture at the reaction temperature.The products methylpseudoionone, dimethylpseudoionone, pseudoirone, methylpseudoirone and dimethylpseudoirone are useful scents and scent intermediates. In addition, pseudoionone is an important intermediate for the industrial preparation of vitamin A, and 6-methyl-hepta-3,5-dien-2-one is a sought-after aromatic.Type: GrantFiled: March 24, 1982Date of Patent: February 14, 1984Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann, Lothar Arnold, Manfred Stroezel, Hans-Juergen Scheiper
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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: 4343953Abstract: The present invention relates to a novel method for producing cyclopentenolone of the formula (I), ##STR1## which is a useful intermediate for producing agricultural chemicals, which comprises reacting an acetonedicarboxylic ester of the formula (VII), ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group, with 2-propynyl chloride in the presence of magnesium alkoxide and in the presence of alkali iodide to obtain novel mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI), ##STR3## wherein R is as defined above; hydrolyzing the mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI) under alkaline conditions with an alkali and then reacting the hydrolyzed product with methylglyoxal of the formula, ##STR4## to obtain novel .gamma.-diketone of the formula (V), ##STR5## and ring-closing the .gamma.-diketone of the formula (V) under alkaline condition.Type: GrantFiled: June 16, 1980Date of Patent: August 10, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Nobushige Itaya, Kohichi Aketa, Osamu Magara, Toshio Nishioka
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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: 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: 4232166Abstract: The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E and F series wherein C-16 is substituted with hydroxy and methyl and a double bond is introduced between C-19 and C-20. These compounds are active as bronchodilators, anti-ulcer agents and fertility control agents.Type: GrantFiled: June 7, 1979Date of Patent: November 4, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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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