Carbon To Carbon Unsaturation In The Aldehyde Prepared Patents (Class 568/459)
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Patent number: 4820876Abstract: Synthetic polyethylene wax having low molecular weight of 250 to 3000 and a density of 0.930 to 0.950 is prepared in a high pressure process at pressures of at least 800 bar using a carbonyl compound such as acetaldehyde as chain transfer agent. The resulting wax with incorporated CO has good compatibility in hot melt systems, and may be stripped to remove light ends, increase density and crystallinity and improve thermal stability.Type: GrantFiled: May 27, 1987Date of Patent: April 11, 1989Assignee: Exxon Research & Engineering Co.Inventors: Hugo J. C. Nuttens, Gerard Van Haeren
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Patent number: 4801444Abstract: A medicinal preparation for individual prevention of venereal diseases and treatment of urogenital trichomoniasis comprises an efficient quantity of an active principle which is essentially a synergistic mixture of para-nitro-alpha-chlorocinnamic aldehyde of the formula: ##STR1## dimethylsulphoxide and a pharmaceutical excipient. Polyethyleneglycol having a molecular mass of 400 is recommended to be used as the pharmaceutical excipient.A method for treatment of urogenital trichomoniasis consists in application of the medicinal preparation in question to the mucosa of human genitalia in a dose of 1.5 to 10 ml twice a day for 5 to 7 days.Type: GrantFiled: March 3, 1988Date of Patent: January 31, 1989Assignee: Poltavsky Meditsinsky Stomatologichesky InstitutInventor: Vladimir G. Kravchenko
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Patent number: 4760193Abstract: Polyene aldehydes are made by reaction of a carbonyl compound of formula: ##STR1## in which R denotes a hydrocarbon radical and R' denotes hydrogen or alkyl, with a metal derivative of a halogen compound of formula: ##STR2## in which X denotes halogen (preferably bromine), R.sub.3 is alkyl, and either R.sub.1 denotes hydrogen and R.sub.2 denotes an alkoxy radical identical with OR.sub.3 or R.sub.1 and R.sub.2 together form a bond, followed by hydrolysis of the product obtained.Type: GrantFiled: March 11, 1987Date of Patent: July 26, 1988Assignee: Rhone-Poulenc SanteInventors: Lucette Duhamel, Pierre Duhamel, Jean-Pierre Lecouve
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Patent number: 4739111Abstract: A process for preparing a catalyst composition wherein a Metal Hydrocarboxide I, such as aluminum secbutoxide, a Metal Hydrocarboxide II, such as zirconium butoxide, an acidic phosphorus-oxygen composition, such as phosphoric acid, and water, are reacted in the presence of a liquid organic medium, such as acetone, to form a catalyst precursor composition, which is then calcined to form the catalyst, is disclosed. The catalyst is useful for condensing carboxylic acids or their ester with aldehydes or acetals to synthesize .alpha. ,.beta.-ethylenically unsaturated acids or esters, such as methylmethacrylate.Type: GrantFiled: September 11, 1985Date of Patent: April 19, 1988Assignee: Exxon Research & Engineering Co.Inventor: Ji-Yong Ryu
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Patent number: 4709098Abstract: Ketones or aldehydes containing one or more carbon-carbon double bonds and a carbonyl group conjugated with at least one double bond are hydrolyzed by the action of heat and pressure in the presence of water. The ketone or aldehyde cleaves at the double bond conjugated with the carbonyl group to produce additional carbonyl-containing compounds.Type: GrantFiled: February 4, 1987Date of Patent: November 24, 1987Assignee: Mallinckrodt, Inc.Inventors: Joseph E. Dolfini, Jerome Glinka
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4634778Abstract: Process for preparing chlorinated ethylenic derivatives of the formula ##STR1## in which R.sub.1 represents acetyl, formyl optionally in the form of an acetal, hydroxy optionally as an ether or ester, alkyloxycarbonyl, alkyl of 1 to 12 carbon atoms substituted by one or more acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, alkenyl of 2 to 12 carbon atoms containing one or more double bonds optionally substituted by one or more of acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, or R.sub.1 represents 3-sulpholenyl or a radical of formula ##STR2## in which R.sub.2 denotes a hydrogen or acetyl, by reacting chlorine in a nonpolar aprotic solvent with a compound of general formula ##STR3## in which R.sub.1 is defined as above. The products of formula I, some of which are new, are useful as intermediates in the synthesis of terpene products such as vitamin E.Type: GrantFiled: November 16, 1984Date of Patent: January 6, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel, Pierre Chabardes
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Patent number: 4571438Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: March 21, 1985Date of Patent: February 18, 1986Assignee: Phillips Petroleum CompanyInventors: Jim D. Byers, Dennis S. Banasiak
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Patent number: 4528405Abstract: A process is disclosed for the aldol condensation of enolizable aldehydes to alpha, beta-unsaturated aldehydes, at high selectivities, employing a metal carboxylate catalyst.Type: GrantFiled: December 30, 1983Date of Patent: July 9, 1985Assignee: Union Carbide CorporationInventor: Anthony J. Papa
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Patent number: 4503239Abstract: Process for the preparation of halogenoacetals of the general formula: ##STR1## wherein X represents chlorine or bromine, the symbols R each represent a linear or branched alkyl radical (1 to 6 carbon atoms) or together form a linear or branched alkylene radical (2 to 6 carbon atoms), and the symbols R.sub.1 and R.sub.2, which are identical or different, represent a hydrogen atom or an alkyl radical (1 to 6 carbon atoms), by reaction of chlorine or bromine with a .beta.,.gamma.-ethylenic aldehyde, in the presence of a tertiary amide, followed by reaction with a primary or secondary aliphatic alcohol, a diol (preferably a glycol) or an alkyl orthoformate.Type: GrantFiled: December 16, 1982Date of Patent: March 5, 1985Assignee: Rhone-Poulenc SanteInventor: Jean Desmurs
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Patent number: 4487962Abstract: An oxidation catalyst wherein the catalytically active component has the general formulaMo.sub.12 P.sub.a Rh.sub.b Cu.sub.c V.sub.d Cs.sub.e X.sub.f Y.sub.g Z.sub.h O.sub.x,where X is Cr and/or Fe, Y is Nb, Z is Na, Li, K and/or Rb, a is 0.1-4, b is 0.001-1, c is 0.05-2, d is 0.05-4, e is 0.1-5, f is 0-2, g is 0-3 and h is 0-2, and x is the number of oxygen atoms required to saturate the valencies of the other constituents, is very suitable for the preparation of methacrylic acid by gas phase oxidation of methacrolein with an oxygen-containing and steam-containing gas mixture.Type: GrantFiled: September 27, 1982Date of Patent: December 11, 1984Assignee: BASF AktiengesellschaftInventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
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Patent number: 4433174Abstract: Alpha, beta-unsaturated aldehydes are prepared by reacting formaldehyde and a reactant aldehyde of formula RCH.sub.2 CHO wherein R is a member of the class consisting of -H, -alkyl, -aryl, -aralkyl, -cycloalkyl, and -alkylaryl radicals in the presence of AMS-1B borosilicate crystalline molecular sieve catalyst. Metacrolein is prepared from propionaldehyde and formaldehyde.Type: GrantFiled: July 26, 1982Date of Patent: February 21, 1984Assignee: Standard Oil Company (Indiana)Inventor: Gary P. Hagen
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Patent number: 4381411Abstract: A process is provided for the oxydehydrogenation of aldehydes such as isobutyraldehyde with oxygen in the presence of iron phosphorus oxide catalysts containing promoters selected from Ag, Al, B, Be, Cd, Co, Cr, Cu, Ga, Ge, In, Mn, Ni, Te, Th, Ti, Tl, U, V, Zn, Zr, rare earths and mixtures thereof.Type: GrantFiled: June 22, 1981Date of Patent: April 26, 1983Assignee: The Standard Oil CompanyInventors: S. Erik Pedersen, Louis F. Wagner
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Patent number: 4346239Abstract: A process for the preparation of 2-methylene aldehydes is disclosed wherein formaldehyde is reacted with an aldehyde of the general formula R--CH.sub.2 CHO, where R stands for a substituted or unsubstituted organic radical having from 2 to 12 carbon atoms. The reaction takes place in the presence of a mixture of a secondary amine and an organic carboxylic acid having up to 5 carbon atoms.Type: GrantFiled: December 29, 1980Date of Patent: August 24, 1982Assignee: Ruhrchemie AGInventors: Hanswilhelm Bach, Eike Brundin, Wilhelm Gick
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Patent number: 4320227Abstract: A process for producing methacrolein and methacrylic acid by oxidizing isobutyl aldehyde with molecular oxygen or molecular oxygen-containing gas in the vapor phase characterized by the use of a catalyst of heteropoly-acid or a mixture of heterpoly-acid and its salt which has the general formula:Mo.sub.a V.sub.b P.sub.c X.sub.d Y.sub.e O.sub.fwherein Mo, V, P and O represent respectively molybdenum, vanadium, phosphorus and oxygen, X represents one or more elements selected from the group consisting of copper, tin, thorium, aluminum, germanium, nickel, iron, cobalt, zinc, titanium, lead, rhenium, zirconium, cerium, chromium, bismuth and arsenic, Y represents one or more elements selected from the group consisting of potassium, rubidium, cesium and thallium and a, b, c, d, e and f represent the atomic ratio of the elements where,a is 10,b is a number of 6 or less than 6 excluding 0,c is a number of 0.5 to 6,d is a number of 3 or less than 3 excluding 0,e is a number of 0 to 0.Type: GrantFiled: January 4, 1980Date of Patent: March 16, 1982Assignee: Nippon Kayaku Kabushiki KaishaInventors: Mutsumi Matsumoto, Kouichi Wada
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Patent number: 4320228Abstract: Olefinically unsaturated carbonyl compounds R.sup.1 --CHR.sup.2 --CHR.sup.3 --C(R.sup.4)O (I) and alcohols R.sup.1 --CHR.sup.2 --CHR.sup.3 --CH(R.sup.4)--OH (II) (where R.sup.1 is an olefinically unsaturated organic radical, and R.sup.2, R.sup.3 and R.sup.4 are H or C.sub.1 -C.sub.4 -alkyl) are prepared by hydrogenating the carbonyl compounds R.sup.1 --CR.sup.2 .dbd.CR.sup.3 --C(R.sup.4)O (III) in the liquid phase with hydrogen, using a catalyst system comprising, firstly, Pd and, secondly, Ru, Rh, Os, Ir or Pt, in the presence of from 5 to 40% by weight, based on (III), of a tertiary amine, under a hydrogen pressure of from 1 to 20 bar is predominantly (I) is to be obtained and from 20 to 150 bar if predominantly (II) is to be obtained.The process is of particular importance for the hydrogenation of citral (IIIa) to give citronellal (Ia) or citronellol (IIa), the preferred amine being trimethylamine.Type: GrantFiled: July 8, 1980Date of Patent: March 16, 1982Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang, Axel Nissen
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Patent number: 4316990Abstract: In the present invention aliphatic aldehydes are condensed to form .alpha.,.beta.-unsaturated aldehydes by use of a heterogeneous catalyst. Such process uses an anatase titanium dioxide catalyst in a fixed bed process under mild temperature conditions to yield high conversions and high yields, and which also eliminates the catalyst removal steps required by conventional processes.Type: GrantFiled: October 29, 1980Date of Patent: February 23, 1982Assignee: Eastman Kodak CompanyInventor: Don L. Morris
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Patent number: 4307034Abstract: An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inert organic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide and cooling the dispersion. The dispersion of alkali hydroxide is used in a reaction of an active methylene compound with an organoalkyl halide such as a reaction of a halophenylacetonitrile with an isopropyl halide to obtain .alpha.-isopropyl halophenylacetonitrile.Type: GrantFiled: September 13, 1979Date of Patent: December 22, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
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Patent number: 4277625Abstract: New process for the preparation of muscone, a valuable macrocyclic musky perfume ingredient. The process makes use of an .alpha.,.omega.-dialdehyde as starting material.Type: GrantFiled: November 20, 1979Date of Patent: July 7, 1981Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Arnold Hauser, Gunther Ohloff
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Patent number: 4273944Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.Type: GrantFiled: October 30, 1979Date of Patent: June 16, 1981Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
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Patent number: 4268444Abstract: A process for the preparation of polyene-aldehydes, derived from 2,6-dimethyl-2,4,6,8-nonatetraen-1-al by substitution in the 9-position, by means of the Wittig ylide synthesis. The process is based on the observation, contrary to all expectation, that on reacting 2,6-dimethyl-octa-2,4,6-triene-1,8-dial with an equimolar amount of an ylide, it is exclusively the 8-al group of the dialdehyde which reacts. This specificity of the reaction is of particular importance for the preparation of the food dye .beta.-apo-8'-carotinal.Type: GrantFiled: November 16, 1979Date of Patent: May 19, 1981Assignee: BASF AktiengesellschaftInventor: Hagen Jaedicke