Carbon To Carbon Unsaturation In The Aldehyde Prepared Patents (Class 568/459)
  • Patent number: 4820876
    Abstract: 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: Grant
    Filed: May 27, 1987
    Date of Patent: April 11, 1989
    Assignee: Exxon Research & Engineering Co.
    Inventors: Hugo J. C. Nuttens, Gerard Van Haeren
  • Patent number: 4801444
    Abstract: 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: Grant
    Filed: March 3, 1988
    Date of Patent: January 31, 1989
    Assignee: Poltavsky Meditsinsky Stomatologichesky Institut
    Inventor: Vladimir G. Kravchenko
  • Patent number: 4760193
    Abstract: 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: Grant
    Filed: March 11, 1987
    Date of Patent: July 26, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Lucette Duhamel, Pierre Duhamel, Jean-Pierre Lecouve
  • Patent number: 4739111
    Abstract: 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: Grant
    Filed: September 11, 1985
    Date of Patent: April 19, 1988
    Assignee: Exxon Research & Engineering Co.
    Inventor: Ji-Yong Ryu
  • Patent number: 4709098
    Abstract: 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: Grant
    Filed: February 4, 1987
    Date of Patent: November 24, 1987
    Assignee: Mallinckrodt, Inc.
    Inventors: Joseph E. Dolfini, Jerome Glinka
  • Patent number: 4705650
    Abstract: 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: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4634778
    Abstract: 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: Grant
    Filed: November 16, 1984
    Date of Patent: January 6, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel, Pierre Chabardes
  • Patent number: 4571438
    Abstract: 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: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4528405
    Abstract: 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: Grant
    Filed: December 30, 1983
    Date of Patent: July 9, 1985
    Assignee: Union Carbide Corporation
    Inventor: Anthony J. Papa
  • Patent number: 4503239
    Abstract: 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: Grant
    Filed: December 16, 1982
    Date of Patent: March 5, 1985
    Assignee: Rhone-Poulenc Sante
    Inventor: Jean Desmurs
  • Patent number: 4487962
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: December 11, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
  • Patent number: 4433174
    Abstract: 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: Grant
    Filed: July 26, 1982
    Date of Patent: February 21, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: Gary P. Hagen
  • Patent number: 4381411
    Abstract: 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: Grant
    Filed: June 22, 1981
    Date of Patent: April 26, 1983
    Assignee: The Standard Oil Company
    Inventors: S. Erik Pedersen, Louis F. Wagner
  • Patent number: 4346239
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: August 24, 1982
    Assignee: Ruhrchemie AG
    Inventors: Hanswilhelm Bach, Eike Brundin, Wilhelm Gick
  • Patent number: 4320227
    Abstract: 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: Grant
    Filed: January 4, 1980
    Date of Patent: March 16, 1982
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Mutsumi Matsumoto, Kouichi Wada
  • Patent number: 4320228
    Abstract: 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: Grant
    Filed: July 8, 1980
    Date of Patent: March 16, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang, Axel Nissen
  • Patent number: 4316990
    Abstract: 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: Grant
    Filed: October 29, 1980
    Date of Patent: February 23, 1982
    Assignee: Eastman Kodak Company
    Inventor: Don L. Morris
  • Patent number: 4307034
    Abstract: 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: Grant
    Filed: September 13, 1979
    Date of Patent: December 22, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
  • Patent number: 4277625
    Abstract: 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: Grant
    Filed: November 20, 1979
    Date of Patent: July 7, 1981
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Arnold Hauser, Gunther Ohloff
  • Patent number: 4273944
    Abstract: 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: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4268444
    Abstract: 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: Grant
    Filed: November 16, 1979
    Date of Patent: May 19, 1981
    Assignee: BASF Aktiengesellschaft
    Inventor: Hagen Jaedicke