Processes Patents (Class 568/426)
  • Patent number: 5260487
    Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting a magnesium bis-hydrocarbyloxide derived at least in part from a hydroxyaromatic compound having at least one free position ortho to the hydroxyl group with formaldehyde or formaldehyde-liberating compound under substantially anhydrous conditions.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: November 9, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Daniel Levin
  • Patent number: 5241122
    Abstract: Catalysts, catalyst precursors, and catalytic systems are provided. The catalysts generally comprise a substrate that includes a group IB metal and a porous, microcrystalline layer that includes the metal and that is disposed on at least a portion of the substrate. The catalysts are prepared by providing a substrate that includes group IB metal, oxidizing said substrate in the presence of stainless steel to produce an oxide coating of said group IB metal, and reducing substantially all of said oxidized substrate.
    Type: Grant
    Filed: March 3, 1992
    Date of Patent: August 31, 1993
    Assignee: Union Camp Corporation
    Inventors: James B. Woell, John W. Catino
  • Patent number: 5225602
    Abstract: Phenylacetaldehydes of the structure (I) ##STR1## where the substituents X are 2,4-dichloro, difluoro, trifluoro, tetrafluoro, p-trifluoromethyl, 2-methyl-4-fluoro, haloalkoxy or haloalkylthio radicals or are adjacent Cl, F, CF.sub.3, alkyl, alkoxy, haloalkoxy and/or haloalkylthio radicals.
    Type: Grant
    Filed: October 17, 1989
    Date of Patent: July 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Rudolf Kropp, Hans Theobald, Bernd Wolf
  • Patent number: 5220074
    Abstract: The present invention relates to novel optically active isoxazole derivatives represented by general formula: ##STR1## which are useful as intermediates for synthesis of prostaglandin and a process for producing the same as well as novel aldehyde compounds represented by general formula: ##STR2## which are intermediates for preparing the compounds [XI] described above and a process for preparation thereof. In the compounds shown by these formulae, R.sup.1 represents an alkyl group or a cycloalkyl group which may have an alkoxy group or a group shown by -Ra-A-B (wherein Ra is an alkyl group; A is a hetero atom or an single bond; and B is an aromatic or hetero ring which may have a substituent(s)); and R.sup.2 and R.sup.3, which may be the same or different, each represents an aralkyl group, a silyl group or an acyl group.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: June 15, 1993
    Assignee: Daiso Co., Ltd.
    Inventors: Takashi Takahashi, Kazuhiko Sakaguchi
  • Patent number: 5210317
    Abstract: Disclosed is a method of producing an aldehyde in which a primary alcohol is reacted with an oxidizing agent selected from the group consisting of ketone, aldehyde and quinone in the presence of a diluent which does not participate in the reaction, in the presence of a partially dehydrated zirconium hydroxide, so as to oxidize the primary alcohol into its corresponding aldehyde.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: May 11, 1993
    Assignee: Japan Tobacco Inc.
    Inventors: Hideyuki Kuno, Makoto Shibagaki, Kyoko Takahashi, Hajime Matsushita
  • Patent number: 5208384
    Abstract: 2-Methylbenzaldehyde dialkyl acetals of the general formula I ##STR1## where R.sup.1 is C.sub.3 -C.sub.20 -alkyl or C.sub.1 -C.sub.12 -alkoxy and R.sup.2 is C.sub.1 -C.sup.8 -alkyl, with the proviso that R.sup.1 is not methoxy when R.sup.2 is methyl, are prepared and are used for the preparation of 2-methylbenzaldehydes.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: May 4, 1993
    Assignee: BASF Aktiengesellschaft
    Inventor: Dieter Hermeling
  • Patent number: 5202497
    Abstract: The invention relates to a process for preparing unsaturated aldehydes and their enamines by the oxidation of allylic tertiary amines in the presence of an alkyl hydroperoxide and a vanadium-based catalyst.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: April 13, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Serge Henrot
  • Patent number: 5191126
    Abstract: Process for the preparation, in high yields, of difluorobenzaldehydes of the formula (1) ##STR1## in which the second fluorine atom is in the 4 or 6 position, by reacting a dichlorobenzaldehyde of the formula (2) ##STR2## in which the second chlorine atom is in the 4 or 6 position, with an alkali metal fluoride in a dipolar aprotic solvent in the presence of an ethylene glycol dialkyl ether as catalyst of the formula (3)RO--(CH.sub.2 --CH.sub.2 --O).sub.n --R (3)in which R is a methyl, ethyl or propyl or isopropyl group and n is a number from 1 to about 50, at temperatures of about 160.degree. C. to about 250.degree. C.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: March 2, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Theodor Papenfuhs, Andreas Kanschik-Conradsen
  • Patent number: 5171880
    Abstract: The present invention is directed to a process of oxidizing organic compounds having benzylic carbon atoms. The process of this invention comprises reacting an organic compound having one or more benzylic carbon atoms with an effective amount of an effective oxidizing agent in water at a temperature equal to or greater than about 350.degree. C. and at a pressure equal to or greater than about 175 atmospheres, wherein said agent is selected from the group consisting of a combination of one or more bases and one or more of elemental sulfur, an oxidized form of elemental sulfur and/or an organic or inorganic sulfur containing compounds capable of forming elemental sulfur, said oxidized forms or a combination thereof in situ under process conditions, and organic or inorganic compounds which form one or more bases and elemental sulfur, oxidized forms of sulfur or a combination thereof in situ under process conditions.
    Type: Grant
    Filed: March 15, 1991
    Date of Patent: December 15, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Divakaran Masilamani, David M. Hindenlang
  • Patent number: 5171891
    Abstract: The present invention is directed to a process of oxidizing organic compounds having allylic or benzylic carbon atoms. The process of this invention comprises reacting an organic compound having one or more allylic or benzylic carbon atoms with an effective amount of an effective oxidizing agent in water at a temperature equal to or greater than about 350.degree. C. and at a pressure equal to or greater than about 175 atmospheres, wherein said agent is selected from the group consisting of elemental sulfur, an oxidized form of elemental sulfur and, an organic or inorganic compound capable of forming elemental sulfur or said oxidized forms in situ under process conditions.
    Type: Grant
    Filed: September 1, 1987
    Date of Patent: December 15, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Divakaran Masilamani, David M. Hindenlang
  • Patent number: 5169943
    Abstract: The invention concerns a chiral reaction medium for organic reactions and consists of concentrated aqueous solution of at least one carbohydrate selected from among the mono-, di- and tri-saccharides and their alkylglucosides of which the alkyl group comprises from 1 to 4 C atoms.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: December 8, 1992
    Assignee: Beghin-Say, S.A.
    Inventors: Andre Lubineau, Hugues Bienayme, Yves Queneau
  • Patent number: 5155279
    Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a solvent, in the absence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the aldehyde.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: October 13, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5155280
    Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate, a non-basic polar solvent and an oxidant, for about eight hours or less at a temperature in the range of from about 10.degree. C. to about 20.degree. C. and thereafter separating out the aldehyde.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: October 13, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5155278
    Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a non-basic polar solvent, in the presence of an oxidant, for about eight hours or less at a temperature in the range of from about -10.degree. C. to about 25.degree. C., and thereafter separating out the aldehyde.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: October 13, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5155277
    Abstract: A process for converting tertiary amine N-oxides to aldehydes by reacting tertiary amine N-oxides in the presence of a catalytic quantity of a vanadium containing compound.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: October 13, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Serge Henrot, Claude Mercier
  • Patent number: 5149882
    Abstract: 2-chloro-5-nitrobenzaldehyde or an acetal thereof is isolated from a mixture of isomers thereof at a temperature of from -10.degree. to +140.degree. C., by suspending the mixture of isomers in a solvent or solvent mixture.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: September 22, 1992
    Inventors: Bernd Schaefer, Wolfgang Freund, Gernot Reissenweber
  • Patent number: 5138099
    Abstract: 4-fluorobenzaldehydes are formed from compounds of the formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different, and represent H, halogen, or an alkyl group of from 1 to about 10 carbon atoms, wherein, when at least one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is halogen, at least one of remaining R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is alkyl. the compound of formula of (I) is reacted with a formylating agent in the presence of FeCl.sub.3 in a reaction mixture, from which is separated a compound of the formula (II) ##STR2## wherein R.sub.1, R.sub.2 , R.sub.3 and R.sub.4 are as defined above.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: August 11, 1992
    Assignee: Mallinckrodt Specialty Chemicals Company
    Inventor: John F. Lang
  • Patent number: 5124487
    Abstract: p-Trifluoromethyl benzaldehydes are prepared by the catalytic reduction reaction of p-trifluoromethyl benzonitriles with hydrogen in an aqueous formic acid media in the presence of a nickel/aluminum alloy catalyst.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: June 23, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: James J. Maul, Garra C. Lester, Henry C. Lin
  • Patent number: 5107032
    Abstract: A process for the preparation of o-phthalaldehydes is disclosed comprising the steps of (1) halogenating an o-xylene and (2) hydrolysis of the resulting tetrahalogeno-o-xylene.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: April 21, 1992
    Assignee: Noramco, Inc.
    Inventors: Dudley K. Erb, Janet E. Goldstein
  • Patent number: 5068408
    Abstract: A process for oxidizing an organic compound selected from an aliphatic, aromatic, aliphatic/aromatic, cycloaliphatic and heterocyclic alcohol, thiol, sulfide, aldehyde, amine, amide, ketone, acid, ether, ester, and organic compounds containing an activated carbon-carbon double bond, which process comprises contacting said organic compound dissolved in an organic solvent with a hypochlorous acid solution.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: November 26, 1991
    Assignee: Olin Corporation
    Inventors: Robert J. Raynor, Budd L. Duncan
  • Patent number: 5068451
    Abstract: A method of producing 3-phenoxy propanal derivatives of 3-phenoxy propanal derivatives of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are --H, --CH.sub.3 or a halogen radical, which comprises oxidizing allyl phenoxy ether derivatives of the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, in an alcohol as a solvent in the presence of a palladium salt, an oxidant, optionally an alkali metal salt of an onganic acid, and/or an acid at a temperature of 5.degree. C. -100.degree. C.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: November 26, 1991
    Assignee: National Science Council
    Inventors: Ivan J. B. Lin, S. J. Jong
  • Patent number: 5059716
    Abstract: Aromatic and aliphatic aldehydes can be prepared from the corresponding aromatic or aliphatic carboxylic acids or the esters, anhydrides or halides thereof at elevated temperature by catalytic gas phase hydrogenation using hydrogen if use is made of a catalyst system composed of oxides of titanium and/or vanadium and of one or more co-metals, the co-metals being selected from the group consisting of chromium, molybdenum, cobalt, nickel, zinc, cadmium and copper.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Joentgen, Helmut Fiege
  • Patent number: 5055621
    Abstract: .alpha.-cinnamic aldehydes especially amyl and hexyl cinnamic aldehydes, are prepared by aldol condensation using a glycol solvent especially diethylene glycol.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: October 8, 1991
    Assignee: Unilever Patent Holdings B.V.
    Inventor: Laurence S. Payne
  • Patent number: 5053552
    Abstract: The present invention provides a novel process for producing .alpha.,.beta.-unsaturated aldehydes including industrial important fragrances such as citral and sinensal, starting materials for preparing pharmaceutical drugs such as senecioaldehyde, farnesal, 8-acetoxy-2,6-dimethyl-2,6-octadienal and the like, directly and in high yield, from formic acid esters of allylic alcohols in the presence of a catalytic amount of aluminum alkoxide by the oxidation of the corresponding alehyde.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: October 1, 1991
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 5053559
    Abstract: 1,2,4-Trioxanes are subjected to reductive cleavage, thereby to produce a 1,2-diol and carbonyl compound. The process has applications both in the synthesis of 1,2-diols and the protection, in the course of organic synthesis, of carbonyl compounds.
    Type: Grant
    Filed: December 29, 1989
    Date of Patent: October 1, 1991
    Assignee: Oxaco S.A.
    Inventor: Charles W. Jefford
  • Patent number: 4990684
    Abstract: Phenylacetaldehydes of the general formula I ##STR1## where each of R.sup.1 to R.sup.5 is independently of the others hydrogen, halogen, unsubstituted or halogen-substituted alkyl, alkenyl, alkoxyl, alkylthio or cycloalkyl, are prepared by converting glycidic esters of the general formula II ##STR2## where each of R.sup.1 to R.sup.5 is as defined above and R.sup.6 is tertbutyl or i-propyl, in the presence of zeolites and/or phosphates and/or phosphoric or boric acid on a carrier material and/or acidic metal oxides as catalysts.
    Type: Grant
    Filed: July 12, 1989
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 4967009
    Abstract: This invention relates to a method for manufacturing aromatic compounds having the following formula (II) comprising the step of reacting an unsaturated aromatic compound having the following formula (I) with an aryl compound containing an iodosyl group or the salt thereof within a temperature range of from -50.degree. to 200.degree. C.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: October 30, 1990
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Kouichi Iwamoto
  • Patent number: 4927805
    Abstract: Curcumin is subjected to the action of heat and pressure in the presence of water by a continuous or batch process to produce vanillin and other natural flavor products. The proportion of vanillin in the final product varies with the pH of the reaction mixture.
    Type: Grant
    Filed: January 25, 1989
    Date of Patent: May 22, 1990
    Assignee: Mallinckrodt, Inc.
    Inventors: Joseph E. Dolfini, Jerome Glinka, Andrew C. Bosch
  • Patent number: 4847422
    Abstract: The invention relates to a method for the production of vanillin in the form of a very pure product by oxidizing lignin contained in the wood pulping liquor. According to the invention the separation and purification of vanillin from the reaction mixture is carried out by means of an extraction at a supercritical pressure and temperature. Carbon dioxide, for instance, can be used as a extraction gas.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: July 11, 1989
    Assignee: Yhtyneet Paperitehtaat Oy
    Inventors: Aarno Klemola, Juhani Tuovinen
  • Patent number: 4837201
    Abstract: 4-methyl-4-phenyl-1-pentanals of the general formula I ##STR1## where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen or methyl, with the exception of 4-methyl-4-phenyl-1-pentanal, and the use of the methylphenylpentanals of the formula I for imparting fragrance properties to, or improving or modifying the fragrance properties of, perfumes and perfumed products, and the preparation of these compounds by hydroformylation of the corresponding 3-methyl-3-phenyl-1-butenes of the general formula II ##STR2## and, if required, subsequent reaction with formaldehyde and partial hydrogenation.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: June 6, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Norbert Goetz, Hardo Siegel, Gerhard Schindler
  • Patent number: 4814510
    Abstract: Benzaldehyde derivatives of the general formula I, where X is an oxygen atom or two R.sup.2 O groups and R.sup.1 and R.sup.2 are alkyl radicals of 1-4 carbon atoms, their preparation, and their use as odorants or odorant intermediates.
    Type: Grant
    Filed: December 14, 1987
    Date of Patent: March 21, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Degner, Walter Gramlich, Heinz Hannebaum
  • Patent number: 4806668
    Abstract: The invention relates to a process for the production of (5-chloro-3-hydroxycyclopentyl) acetaldehydes of formula II ##STR1## in which R signifies a benzyl radical, a tert-butyldimethylsilyl radical or a tert-butyldiphenylsilyl radical, characterized in that a compound of formula I ##STR2## in which R has the meanings already mentioned, is reduced in the presence of a reduction agent.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: February 21, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Bernd Raduechel, Werner Skuballa, Helmut Vorbrueggen
  • Patent number: 4723042
    Abstract: Alpha,beta-substituted acroleins of the general formula I ##STR1## where A and B are identical or different and are each C.sub.1 -C.sub.4 -alkyl, naphthyl, biphenyl or phenyl which may be monosubstituted or polysubstituted by halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, phenoxy or phenylsulfonyl, are prepared by a process in which a compound of the general formula III ##STR2## where A has the above meanings and R.sup.1 and R.sup.2 are identical or different and are each C.sub.1 -C.sub.4 -alkyl or together possess the carbon atoms required to complete a ring, is reacted with a phosphorus compound of the general formula IV or V ##STR3## where B the meanings stated above, R.sup.1 and R.sup.2 are as defined above and X.sup..crclbar. is a halide ion, in the presence of a base. The alpha,beta-substituted acroleins can be further processed to give hydroxymethyloxiranes.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: February 2, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Stefan Karbach, Hans-Gert Recker, Marco Thyes
  • Patent number: 4670108
    Abstract: A process for oxidizing aromatic and alkyl substituted aromatic compounds to carbonyl containing compounds by contacting an aromatic or alkyl aromatic compound with ceric methanesulfonate in an aqueous, weakly acidic solution containing an organic cosolvent which has at least 2 percent solubility in water under reaction conditions and is substantially inert with respect to the acidic, oxidizing conditions.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: June 2, 1987
    Assignee: W. R. Grace & Co.
    Inventors: Robert P. Kreh, Robert M. Spotnitz
  • Patent number: 4647349
    Abstract: A process for oxidizing aromatic and alkyl substituted aromatic compounds to carbonyl containing compounds by contacting an aromatic and alkyl aromatic compound with an aqueous solution of ceric trifluoromethanesulfonate having from at least 0.75 to 7 molar concentration of free acid of trifluoromethanesulfonic acid and at least 0.2 molar cerium ion concentration. The present process provides a highly effective means of forming the desired carbonyl containing product in good yields and high selectivity.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: March 3, 1987
    Assignee: W. R. Grace & Co.
    Inventors: Robert P. Kreh, Robert M. Spotnitz
  • Patent number: 4645852
    Abstract: In an improved process of converting a 1,2-epoxy-2-phenylbutane or a 1,2-epoxy-2-phenylpentane to a 2-hydroxy-2-phenylbutylsulfonate, sulfamate, or halide, or the corresponding 2-hydroxy-2-phenylpentyl compound, respectively, by the reaction at about 40.degree. to 120.degree. C. in the presence of an organic solvent of the requisite epoxybutane or epoxypentane with a proton source and a nucleophile. The proton source can be a free strong acid such as a sulfonic, sulfamic acid, or hydrohalide acid, or the proton source can be derived from an equilibrium system comprising a free strong acid and weak base in equilibrium with the respective deprotonated strong acid and protonated weak base. The process is carried out in one step with reduction or avoidance of aldehyde formation by rearrangement of the epoxyalkane.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: February 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Richard C. Krauss
  • Patent number: 4639298
    Abstract: A process for oxidizing aromatic and alkyl substituted aromatic compounds to carbonyl containing compounds by contacting an aromatic and alkyl aromatic compound with an aqueous solution of ceric methanesulfonate having from at least 1.5 to 9 molar concentration of free acid of methanesulfonic acid and at least 0.2 molar cerium ion concentration. The present process provides a highly effective means of forming the desired carbonyl containing product in good yields and high selectivity.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: January 27, 1987
    Assignee: W. R. Grace & Co.
    Inventors: Robert P. Kreh, Robert M. Spotnitz
  • Patent number: 4617153
    Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: October 14, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Hitosi Nozaki, Koichiro Oshima
  • Patent number: 4612402
    Abstract: A process for the oxidation of olefinically unsaturated substrates of the formula R--CH.dbd.CH-R' wherein R and R' are independently selected from members of the group consisting of H, alkyl, alkenyl, cycloalkyl, aryl and halo-, cyano- and ether-substituted alkyl, alkenyl, cycloalkyl and aryl which comprises reacting in the liquid phase said substrate with a rhodium nitro complex of the formula L.sub.n RhNO.sub.2, wherein n is 4 or 5 and wherein L.sub.n represents any combination of monodentate, bidentate, tridentate and tetradentate ligands such as to provide four or five bonding sites, for a time sufficient to produce an oxidized product of the formula RCH.sub.2 C(O)R' and a reduced product of the formula L.sub.n RhNO is disclosed. A preferred embodiment of the process wherein the rhodium nitro complex contains at least one ligand replaceable by olefin to be oxidized and operates to produce the oxidized product RCH.sub.2 C(O)R' in the absence of other Group VIII metals as co-catalyst is also disclosed.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: September 16, 1986
    Assignee: Allied Corporation
    Inventors: Deborah A. Muccigrosso, Frank Mares, Steven E. Diamond, Jeffrey P. Solar
  • Patent number: 4605778
    Abstract: The present invention relates to novel musk compounds, useful as fragrance materials which have the structure: ##STR1## wherein R is hydrogen or methyl and R.sub.1 and R.sub.2 are hydrogen, methyl, or ethyl, and provides methods for preparing these compounds from readily available intermediates. The invention also provides fragrance compositions which include the compounds, and processes for altering the organoleptic properties of perfume compositions, colognes and perfumed articles by adding organoleptically effective amounts of the compounds.
    Type: Grant
    Filed: June 6, 1984
    Date of Patent: August 12, 1986
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Teodosij Zazula
  • Patent number: 4605758
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4582942
    Abstract: Manufacture of p-tert. butyl-benzaldehyde (TBT) by oxidation with a Mn.sup.3+ salt, which salt is generated by electrochemical oxidation of a Mn.sup.2+ salt, and whereby the chemical oxidation and the electrochemical oxidation are carried out in separate reaction vessels.
    Type: Grant
    Filed: August 15, 1984
    Date of Patent: April 15, 1986
    Assignee: Givaudan Corporation
    Inventors: Christos Comninellis, Eric Plattner
  • Patent number: 4472577
    Abstract: A process for the production of an .alpha.-hydroxy-phosphonic acid ester of the general formula ##STR1## in which R represents an optionally substituted aryl or heteroaryl group, andR.sup.1 and R.sup.2 independently of each other represent an alkyl or phenyl group, or together represent an alkanediyl (alkylene) radical,comprising reacting .alpha.-oxo-phosphonic acid esters with hydrogen in the presence of a hydrogenation catalyst. The .alpha.-hydroxy-phosphonic acid esters of formula (I) are intermediate products for the production of pesticides.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: September 18, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4471118
    Abstract: A process for the preparation of an aldehyde of the formulaR--CHO (I)in which R is an optionally substituted alkyl, alkenyl, alkinyl, cycloakyl, cycloalkenyl, aralkyl, aralkenyl, aryl or heteroaryl radical, comprising heating an .alpha.-hydroxyphosphonic acid ester of the formula ##STR1## the aldehyde of the formula (I) can be used as an intermediate in the production of pest-combating agents.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: September 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4465833
    Abstract: A novel ethynylation process is disclosed which provides an expanded series of novel ethylnyl-terminated aromatic compounds having base sensitive substituents and which facilitates the economic preparation of prior art ethynyl-substituted aromatic compounds.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: August 14, 1984
    Assignees: Hughes Aircraft Company, Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Robert H. Boschan
  • Patent number: 4438269
    Abstract: The novel compound 4-dimethylaminopyridinium chlorochromate has been found to be an effective oxidizing agent for converting alcohols to their respective aldehydes or ketones, especially for the selective conversion of allylic and benzylic alchols to their corresponding aldehydes and ketones.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: March 20, 1984
    Assignee: Thiokol Corporation
    Inventor: Frank S. Guziec, Jr.
  • Patent number: 4399281
    Abstract: 2,2'-Bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.
    Type: Grant
    Filed: September 22, 1981
    Date of Patent: August 16, 1983
    Assignee: Thiokol Corporation
    Inventor: Frank S. Guziec, Jr.
  • Patent number: 4376868
    Abstract: Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: March 15, 1983
    Assignee: Conoco Inc.
    Inventors: Gerald L. Nield, Kang Yang, Paul H. Washecheck
  • Patent number: 4339607
    Abstract: Anisaldehyde is prepared by performing at least once the steps of (a) electrolyzing cerium (III) nitrate or ammonium cerium (III) nitrate to obtain water containing cerium (IV) nitrate or ammonium cerium (IV) nitrate and/or a solution of lower alcohol containing the cerium (IV) salt, and (b) oxidizing p-methyl anisole to anisaldehyde with the cerium (IV) salt-containing solution of lower alcohol with or without the water contained therein, or with the cerium (IV) salt-containing water having a lower alcohol admixed therewith.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: July 13, 1982
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Shigeru Torii, Shoji Nakane, Toshifumi Shirakawa, Mitsuo Akada
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger