Nitrogen Containing Material Utilized Patents (Class 568/436)
  • Patent number: 9006494
    Abstract: The present invention relates to a process for producing vanillin from an aqueous, basic vanillin-comprising composition, in particular from a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, comprising at least one treatment of an aqueous, basic vanillin-comprising composition, in particular the treatment of a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, with a basic adsorbent, in particular an anion exchanger.
    Type: Grant
    Filed: July 3, 2013
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Florian Stecker, Andreas Fischer, Axel Kirste, Agnes Voitl, Chung Huan Wong, Siegfried Waldvogel, Carolin Regenbrecht, Dominik Schmitt, Marius Franziskus Hartmer
  • Publication number: 20150044346
    Abstract: The present invention relates to compounds based on an oxazoline moiety which liberate Strecker aldehydes under mild and controllable conditions. In addition the invention relates to food products comprising such compounds, and uses of such compounds.
    Type: Application
    Filed: March 19, 2013
    Publication date: February 12, 2015
    Inventors: Imre Blank, Thomas Davidek, Ondrej Novotny, Peter Schieberle, Michael Granvogl
  • Publication number: 20150031887
    Abstract: An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.
    Type: Application
    Filed: February 22, 2013
    Publication date: January 29, 2015
    Inventors: Yoshiharu Iwabuchi, Masatoshi Shibuya, Ryusuke Doi
  • Patent number: 8871981
    Abstract: A method for oxidizing an alcohol, wherein oxidation is performed in the presence of a compound represented by the following formula (I) and a bulk oxidant, which enables efficient oxidation of secondary alcohols as well as primary alcohols, and can attain high reaction efficiency even when air is used as a bulk oxidant.
    Type: Grant
    Filed: May 30, 2011
    Date of Patent: October 28, 2014
    Assignee: Tohoku University
    Inventors: Yoshiharu Iwabuchi, Masaki Hayashi
  • Patent number: 8846982
    Abstract: The invention relates to a process for the preparation of a hydroquinone compound of formula (I) wherein R2, R3, R5 and R6 have the meaning according to claim 1, with the steps of formylating a substituted phenol and oxidizing the resulting substituted 4-hydroxy-benzaldehyde under acidic conditions to the corresponding hydroquinone of formula (I). Another object of the invention concerns the intermediate 2,3,5-trimethyl-4-hydroxy-benzaldehyde for synthesis of 2,3,5-trimethyl-hydroquinone (TMHQ) and (dl)?-tocopherol.
    Type: Grant
    Filed: March 17, 2011
    Date of Patent: September 30, 2014
    Assignee: Merck Patent GmbH
    Inventors: Shahuraj Hanamantrao Kadam, Shashikumar Paknikar
  • Patent number: 8692026
    Abstract: A new synthesis of 4-bromo-2-methoxybenzaldehyde is reported from 1,4 dibromo 2-fluorobenzene. First, 2-fluoro-4-bromobenzaldehyde is prepared through metal halogen exchange and formylation with a formyl source at 0° C. After crystallization, this intermediate is reacted with methanol in the presence of potassium carbonate. Subsequently, 4-bromo-2-methoxy-benzaldehyde is crystallized.
    Type: Grant
    Filed: July 1, 2011
    Date of Patent: April 8, 2014
    Assignee: Albemarle Corporation
    Inventors: Thierry J. Giard, Vincent L. Mutterer, Christophe Durvaux
  • Publication number: 20140058106
    Abstract: Described herein are fluorinated organic compounds and methods of making fluorinated organic compounds, for example, using palladium complexes. Also described herein are compositions and kits containing compounds and palladium complexes described herein.
    Type: Application
    Filed: July 29, 2013
    Publication date: February 27, 2014
    Inventors: Tobias Ritter, Takeru Furuya, Hanns M. Kaiser
  • Publication number: 20140046099
    Abstract: The present invention relates to a process for producing vanillin from an aqueous, basic vanillin-comprising composition, in particular from a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, comprising at least one treatment of an aqueous, basic vanillin-comprising composition, in particular the treatment of a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, with a basic adsorbent, in particular an anion exchanger.
    Type: Application
    Filed: July 3, 2013
    Publication date: February 13, 2014
    Inventors: Florian Stecker, Andreas Fischer, Axel Kirste, Agnes Voitl, Chung Huan Wong, Siegfried Waldvogel, Carolin Regenbrecht, Dominik Schmitt, Marius Franziskus Hartmer
  • Publication number: 20130172543
    Abstract: A method for oxidizing an alcohol, wherein oxidation is performed in the presence of a compound represented by the following formula (I) and a bulk oxidant, which enables efficient oxidation of secondary alcohols as well as primary alcohols, and can attain high reaction efficiency even when air is used as a bulk oxidant.
    Type: Application
    Filed: May 30, 2011
    Publication date: July 4, 2013
    Applicant: TOHOKU UNIVERSITY
    Inventors: Yoshiharu Iwabuchi, Masaki Hayashi
  • Patent number: 8461393
    Abstract: The compound according to Formula I is an intermediate in the synthesis of prostacylin analogs. The present invention provides an efficient method for synthesizing a Formula I compound.
    Type: Grant
    Filed: March 1, 2012
    Date of Patent: June 11, 2013
    Assignee: United Therapeutics Corporation
    Inventor: Vijay Sharma
  • Publication number: 20120226076
    Abstract: The compound according to Formula I is an intermediate in the synthesis of prostacylin analogs. The present invention provides an efficient method for synthesizing a Formula I compound.
    Type: Application
    Filed: March 1, 2012
    Publication date: September 6, 2012
    Inventor: Vijay Sharma
  • Patent number: 8212081
    Abstract: A method for preparing a substituted 1,4-quinone methide from a 3,5-disubstituted 4-hydroxybenzaldehyde is provided. Also provided is a method to prepare a 3,5-disubstituted 4-hydroxybenzaldehyde from the corresponding 2,6-disubstituted phenol.
    Type: Grant
    Filed: April 20, 2010
    Date of Patent: July 3, 2012
    Assignee: Evonik Degussa GmbH
    Inventors: Stefanie Rinker, Phillip R. James, Manfred Neumann, Oliver Erpeldinger, Frank Kraushaar
  • Patent number: 8168833
    Abstract: Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.
    Type: Grant
    Filed: December 3, 2009
    Date of Patent: May 1, 2012
    Assignee: Queen's University at Kingston
    Inventors: Yigang Zhao, Victor A. Snieckus
  • Publication number: 20120059179
    Abstract: A new method of ortho-fluorination where an aryl C—H bond is directly replaced by an aryl C-F bond in a palladium-catalyzed reaction is provided. The method includes the ortho-fluorination of a triflamide protected benzylamine, a palladium catalyst, such as Pd(OTf)2, a fluorinating reagent such as N-fluoro-2,4,6-trimethylpyridinium triflate, and a ligand to promote the reaction such as N-methylpyrrolidinone (NMP).
    Type: Application
    Filed: April 2, 2010
    Publication date: March 8, 2012
    Applicant: The Scripps Research Insitiute
    Inventor: Jin-Quan Yu
  • Patent number: 7851659
    Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (2): wherein Q1 and Q2 represent a hydrogen atom etc., including the step of reacting a compound represented by the formula (1): wherein X represents a chlorine atom etc., and Q1 and Q2 are respectively the same meaning as above, with a secondary nitroalkane and a base in the presence of an alkali metal iodide.
    Type: Grant
    Filed: May 14, 2008
    Date of Patent: December 14, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koichi Nakazawa
  • Publication number: 20100267992
    Abstract: A method for preparing a substituted 1,4-quinone methide from a 3,5-disubstituted 4-hydroxybenzaldehyde is provided. Also provided is a method to prepare a 3,5-disubstituted 4-hydroxybenzaldehyde from the corresponding 2,6-disubstituted phenol.
    Type: Application
    Filed: April 20, 2010
    Publication date: October 21, 2010
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Stefanie RINKER, Phillip R. James, Manfred Neumann, Oliver Erpeldinger, Frank Kraushaar
  • Publication number: 20100234645
    Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (2): wherein Q1 and Q2 represent a hydrogen atom etc., including the step of reacting a compound represented by the formula (1): wherein X represents a chlorine atom etc., and Q1 and Q2 are respectively the same meaning as above, with a secondary nitroalkane and a base in the presence of an alkali metal iodide.
    Type: Application
    Filed: May 14, 2009
    Publication date: September 16, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Koichi Nakazawa
  • Patent number: 7790931
    Abstract: A process for preparing tetrafluorobenzene carbaldehyde alkyl acetal represented by the following formula (II), comprising reducing tetrafluorocyanobenzene represented by the following formula (I) with a metal catalyst containing a platinum group metal in the presence of an alkyl alcohol represented by R—OH (R is an alkyl group of 1 to 4 carbon atoms) and an acid; (I) wherein m is 1 or 2, n is 0 or 1, and m+n is 2, (II) wherein m and n are the same as those in the formula (I), and R is an alkyl group of 1 to 4 carbon atoms.
    Type: Grant
    Filed: June 12, 2006
    Date of Patent: September 7, 2010
    Assignee: Showa Denko K.K.
    Inventors: Haruhiko Ikeda, Hideo Miyata, Katsutoshi Ohno, Katsuro Urakawa
  • Patent number: 7750190
    Abstract: Produce the target substance, or a polynuclear poly(formylphenol) expressed by General Formula (2), in an industrial setting with ease and at high purity by causing a polynuclear poly(hydroxymethylphenol) or polynuclear poly(alkoxymethylphenol) to react with hexamethylene tetramine in the presence of an acid and then hydrolyzing the obtained reaction product.
    Type: Grant
    Filed: May 31, 2007
    Date of Patent: July 6, 2010
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai, Kentaro Watanabe
  • Publication number: 20100145060
    Abstract: Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.
    Type: Application
    Filed: December 3, 2009
    Publication date: June 10, 2010
    Inventors: Yigang Zhao, Victor A. Snieckus
  • Publication number: 20100105954
    Abstract: A process for preparing tetrafluorobenzene carbaldehyde alkyl acetal represented by the following formula (II), comprising reducing tetrafluorocyanobenzene represented by the following formula (I) with a metal catalyst containing a platinum group metal in the presence of an alkyl alcohol represented by R—OH (R is an alkyl group of 1 to 4 carbon atoms) and an acid; (I) wherein m is 1 or 2, n is 0 or 1, and m+n is 2, (II) wherein m and n are the same as those in the formula (I), and R is an alkyl group of 1 to 4 carbon atoms.
    Type: Application
    Filed: June 12, 2006
    Publication date: April 29, 2010
    Applicant: SHOWA DENKO K.K.
    Inventors: Haruhiko Ikeda, Hideo Miyata, Katsutoshi Ohno, Katsuro Urakawa
  • Publication number: 20090286968
    Abstract: Disclosed are 2-quinoxalinol salen compounds and in particular 2-quinoxalinol salen Schiff-base ligands. The disclosed 2-quinoxalinol salen compounds may be utilized as ligands for forming complexes with cations, and further, the formed complexes may be utilized as catalysts for oxidation reactions. The disclosed 2-quinoxalinol salen compounds also may be conjugated to solid supports and utilized in methods for selective solid-phase extraction or detection of cations.
    Type: Application
    Filed: April 24, 2009
    Publication date: November 19, 2009
    Applicant: Auburn University
    Inventors: Anne E. V. Gorden, Xianghong Wu
  • Patent number: 7456323
    Abstract: A new 1,3-bis(3-formyl-4-hydroxyphenyl)adamantane, which provides a material offering excellent properties such as heat resistance and mechanical strength for use as an intermediate material for adamantanebisphenol derivatives or use in photosensitive resist materials, epoxy resins and other synthetic resins, thermosensitive recording materials, and the like, can be obtained through an industrial process in an easy manner at a good yield and high purity by producing a Schiff base from a 1,3-bis(4-hydroxyphenyl)adamantane by causing it to react with a hexamethylenetetramine or other substance in the presence of an acid, and then hydrolyzing the obtained Schiff base using an acid. A new polynuclear polyphenol is also provided that may be derived from the same.
    Type: Grant
    Filed: June 13, 2006
    Date of Patent: November 25, 2008
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai, Kentaro Watanabe
  • Publication number: 20080242896
    Abstract: A new 1,3-bis(3-formyl-4-hydroxyphenyl)adamantane, which provides a material offering excellent properties such as heat resistance and mechanical strength for use as an intermediate material for adamantanebisphenol derivatives or use in photosensitive resist materials, epoxy resins and other synthetic resins, thermosensitive recording materials, and the like, can be obtained through an industrial process in an easy manner at a good yield and high purity by producing a Schiff base from a 1,3-bis(4-hydroxyphenyl)adamantane by causing it to react with a hexamethylenetetramine or other substance in the presence of an acid, and then hydrolyzing the obtained Schiff base using an acid. A new polynuclear polyphenol is also provided that may be derived from the same.
    Type: Application
    Filed: June 13, 2006
    Publication date: October 2, 2008
    Applicant: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai, Kentaro Watanabe
  • Patent number: 6903239
    Abstract: The present invention relates to fluorinated benzaldehydes, to a process for preparing them and also to the use of the fluorinated benzaldehydes for preparing active ingredients, especially in medicaments and agrochemicals.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: June 7, 2005
    Assignee: Bayer Chemical Aktiengesellschaft
    Inventors: Karen Peilstöcker, Albrecht Marhold
  • Patent number: 6797844
    Abstract: A process for producing a phthalaldehyde which comprises reacting at least one compound selected between o-xylylene glycol and o-xylylene oxide with nitric acid. The nitric acid is used in an amount of about 0.2 to 20 mol per mol of the compound selected between o-xylylene glycol and o-xylylene oxide. The process enables a phthalaldehyde to be efficiently produced from easily available materials.
    Type: Grant
    Filed: June 11, 2003
    Date of Patent: September 28, 2004
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Tohru Nakai
  • Patent number: 6790964
    Abstract: The present invention provides a method of producing 7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ester (VII) economically, industrially advantageously and efficiently in a large amount.
    Type: Grant
    Filed: August 13, 2002
    Date of Patent: September 14, 2004
    Assignees: Sagami Chemical Research Center, Kuraray Co., Ltd.
    Inventors: Shiro Terashima, Katsuji Ujita, Akihiro Ishiwata
  • Patent number: 6777579
    Abstract: A hydroformylation process is provided that involves reacting a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of a cobalt catalyst and a sulfur-containing additive which suppresses the formation of cobalt carbide in the reaction mixture.
    Type: Grant
    Filed: November 14, 2002
    Date of Patent: August 17, 2004
    Assignee: Shell Oil Company
    Inventors: Peter Arnoldy, Robert Hardy Ellison, Herman Pieter Charles Eduard Kuipers, Robert Moene, Frederik Hendrik Van Der Steen
  • Patent number: 6720458
    Abstract: The present invention relates to a catalyst useful for a photooxidation reaction and also relates to a novel process for producing aldehydes, particularly aromatic aldehydes, which are useful as an intermediate for the production of agrochemical and medical preparations. The catalyst is particularly suitable for the oxidation of a methyl group difficult to oxidize. A photooxidation catalyst according to the invention is a halogenated aromatic nitrile represented by the following formula (1): (wherein X represents a chlorine atom or a fluorine atom, m represents an integer of 1 to 5, n represents an integer of 1 to 5, m+n≦6, and when n is 2 or more, Xs may be the same or different).
    Type: Grant
    Filed: September 6, 2002
    Date of Patent: April 13, 2004
    Assignee: Showa Denko K.K.
    Inventors: Kohei Morikawa, Shunichi Fukuzumi, Kei Ohkubo, Yutaka Ohnishi
  • Patent number: 6624336
    Abstract: The present invention relates to a process by a series of reactions using tetrafluorocyanobenzens as material for producing tetrafluorobenzenemethanols, tetrafluorobenzenecarbaldehyde dialkylacetals and tetrafluorobenzenecarbaldehydes in a high purity and a high yield which are useful as intermediates in the production of cyclopropanecarboxylic acid esters having insecticidal action, and also relates to a novel tetrafluorobenzenecarbaldehyde dimethylacetal.
    Type: Grant
    Filed: November 5, 2001
    Date of Patent: September 23, 2003
    Assignee: Showa Denko K.K.
    Inventors: Toru Sasaki, Tetsuhiro Furukawa, Toru Yoshida, Yutaka Ohnishi, Hiroyuki Monzen, Hideo Miyata, Kohei Morikawa
  • Patent number: 6608229
    Abstract: A simplified process for oxidizing starch and other polysaccharides in an aqueous solution or suspension using hypochlorite in the presence of a catalytic amount of a nitroxyl compound is described. The oxidation is process is bromide-free and is carried out at a pH between 7 and 8.3 and at a temperature between 15 and 25° C.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: August 19, 2003
    Assignee: SCA Hygiene Products Zeist B.V.
    Inventors: Petter Bragd, Arie Cornelis Besemer, Jeffrey Wilson Thornton
  • Patent number: 6596909
    Abstract: The present invention provides the adsorbent which adsorbs the aldehyde efficiently for a long period. The present invention also includes an adsorption device, an article and a method using the same. The adsorbent of the invention comprises a zeolite, wherein the zeolite has NH4+ as ionic species; a crystal structure of ZSM-5 or ferrierite; a molar ratio of SiO2/Al2O3 from 30 to 190; and the zeolite retains a quarternary ammonium salt which adsorbs the aldehyde with the reaction of the aldehyde. In the case of a formaldehyde, the zeolite has NH4+ as ionic species.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: July 22, 2003
    Assignee: Mazda Motor Corporation
    Inventors: Tuyoshi Nishijima, Osamu Takayama
  • Publication number: 20030073871
    Abstract: An alcohol is oxidized to an aldehyde or a ketone in the presence of a nitroxyl compound as catalyst, wherein the alcohol to be oxidized is contained in an organic liquid phase, and is reacted in the presence of a nitroxyl compound with an aqueous phase comprising an oxidant. The reaction is carried out continuously at a contact time of the phases of from 0.1 s to a maximum of 15 minutes, with intensive mixing of the phases. The process produces high yields with low quantities of other oxidation byproducts.
    Type: Application
    Filed: October 4, 2002
    Publication date: April 17, 2003
    Inventors: Elke Fritz-Langhals, Juergen Stohrer, Hermann Petersen
  • Patent number: 6518419
    Abstract: Primary alcohols, especially in carbohydrates, can be selectively oxidized to aldehydes and carboxylic acids in a low-halogen process by using a peracid in the presence of a catalytic amount of a di-tertiary-alkyl nitroxyl (TEMPO) and a catalytic amount of halide. The halide is preferably bromide and the process can be carried out at nearly neutral to moderately alkaline pH (5-11). The peracid can be produced or regenerated by means of hydrogen peroxide or oxygen. The process is advantageous for producing uronic acids and for introducing aldehyde groups which are suitable for crosslinking and derivatization.
    Type: Grant
    Filed: November 7, 2000
    Date of Patent: February 11, 2003
    Assignee: Nederlandse Organisatie voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Jan Pieter Van Der Lugt, Jan Matthijs Jetten, Arie Cornelis Besemer, Hendrik Arend Van Doren
  • Patent number: 6482991
    Abstract: A method and an apparatus for producing aromatic aldehydes, including benzaldehyde and metatolualdehyde wherein the reaction occurs in the vapor phase. Raw materials and a source of oxygen are fed into a tube reactor. The raw materials may be in a liquid or vapor phase. The reaction to form the aldehyde is catalyzed by suitable solid or liquid catalysts, including copper containing catalysts.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: November 19, 2002
    Assignee: EagleView Technologies, Inc.
    Inventors: Jack S. Warren, David R. Westphal, Steve J. Zoubek
  • Patent number: 6201156
    Abstract: An ether of the following formula (2): (wherein Ra is a hydrogen atom, a hydrocarbon group or a heterocyclic group, Rb is a hydrogen atom, a hydroxyl group or a substituted oxy group, and Rc is a hydrocarbon group or a heterocyclic group; Ra and Rc may be combined to form a ring with the adjacent carbon atom and oxygen atom) is reacted with nitrogen monoxide in the presence of a catalyst composed of an imide compound of the following formula (1): (wherein each of R1 and R2 is, identical to or different from each other, a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group; R1 and R2 may be combined to form a double bond, or an aromatic or nonaromatic ring; X is an oxygen atom or a hydroxyl group; and one or two N-substituted cyclic imido groups indicated in the formula (1) may further be formed on R1, R2, or on the double bond or aromatic or nonaromat
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: March 13, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6133409
    Abstract: This invention is directed to a process for the solid phase synthesis of aldehyde, ketone, oxime, amine, hydroxamic acid and .alpha.,.beta.-unsaturated carboxylic acid and aldehyde compounds and to polymeric hydroxylamine resin compounds useful therefor.
    Type: Grant
    Filed: June 24, 1998
    Date of Patent: October 17, 2000
    Assignee: Aventis Pharmaceuticals Products Inc.
    Inventors: Joseph M. Salvino, George C. Morton, Helen J. Mason, Richard F. Labaudiniere
  • Patent number: 5861286
    Abstract: The present invention relates to a process for the preparation of aromatic substances having formula (I), characterized in that a substrate having formula (II) is subjected to an oxydation in the presence of at least one protein and at least one metal ion, formula wherein R.sub.1 may be a radical --H, --CH.sub.3, --CH.sub.2 OH, --CHO, --COOH, --OCH.sub.3, or --COO--CH(COOH)--CH.sub.2 --C.sub.6 H.sub.3 (OH).sub.2 ; R.sub.2 may be a radical --H, --OH, or --OCH.sub.3 ; R.sub.3 may be a radical --H, --OH, --OCH.sub.3, or O-glucosid; R.sub.4 may be a radical --H, --OH, or --OCH.sub.3.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: January 19, 1999
    Assignee: V. Mane Fils
    Inventors: Jean Mane, Joseph Zucca
  • Patent number: 5672765
    Abstract: Aromatic, ring-fluorinated compounds are prepared by reaction of corresponding chlorine compounds or bromine compounds with alkali metal fluorides using a diamide as solvent. Most of the diamides which can be used are novel compounds.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Marianne Lohr, Heinrich Wamhoff
  • Patent number: 5659084
    Abstract: Processes for preparing 2-substituted benzaldehydes of general formula (I), wherein: R.sub.1 is CH.sub.2 CH.sub.2 --(L.sub.1).sub.p --(CH.sub.2).sub.q --(L.sub.2).sub.r --CH.sub.2 --(T).sub.2 --Z; L.sub.1 and L.sub.2 are independently CH.sub.2 CH.sub.2, CH.dbd.CH or C.tbd.C; q is 0 to 8; p, r and s are independently 0 or 1; T is O, S, CH.sub.2, CH.dbd.CH, C.tbd.C; and Z is C.sub.1-4 alkyl, ethynyl, trifluoromethyl, isopropenyl, furanyl, thienyl, cyclohexyl or phenyl optionally mono substituted with CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, methylthio, or trifluoromethylthio; and R.sub.2 and A are independently H, CF.sub.3, C.sub.1-4 alkyl, F, Cl, Br or I; are useful for preparing pharmaceutically active compounds.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: August 19, 1997
    Assignees: SmithKline Beecham Corporation, SmithKline Beecham plc
    Inventors: Kerry Joseph Gombatz, Michael Anthony Forth, Jerome Francis Hayes, Michael Barry Mitchell, Stephen Alexander Smith
  • Patent number: 5599988
    Abstract: A novel process for producing chiral hydroxylamines for use as intermediates to make chiral hydroxyureas, which process comprises a tandem condensation-cyclization reaction between a dimethylsulfoxoniurn methylide and an appropriately substituted nitrone bearing a D- or L- mannose chiral auxiliary to yield a compound of Formula (I) as claimed herein.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: February 4, 1997
    Assignee: SmithKline Beecham Corporation
    Inventor: Wilford Mendelson
  • Patent number: 5471004
    Abstract: The present invention relates to a process for producing an .alpha.,.beta.-unsaturated aldehyde which comprises subjecting an allyl-hexamethylenetetraammonium derivative to hydrolysis in water and an organic solvent homogeneously immiscible with water. The resulting .alpha.,.beta.-unsaturated aldehyde is useful as medicaments, flavorings, etc., or as raw materials for their production.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: November 28, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tatsuhiko Kaneko, Noritaka Kuroda, Kenichi Kashiwa
  • Patent number: 5457239
    Abstract: A process for the preparation of a formylated aromatic compound comprising contacting an aromatic compound with (i) a halogenated compound in the presence of a Lewis acid, and (ii) a base, is described. The subject process provides an efficient and effective means of preparing formylated compounds which may be useful in a wide variety of applications.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: October 10, 1995
    Assignee: Union Camp Corporation
    Inventors: Walter C. Frank, Richard L. Veazey, John J. Mahurter, Mark J. Jenkins, Neil R. Fairfax
  • Patent number: 5434302
    Abstract: The present process is directed to preparing optically active 2-aryl alkyl aldehydes by various processes through the use of an optically active amine, (-)-2'-amino-3-phenyl propane. The aldehyde formed can then be oxidized to produce the corresponding acid.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: July 18, 1995
    Inventor: H. Henrich Paradies
  • Patent number: 5382699
    Abstract: A method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde by reacting 4-hydroxy-3-methoxy-5-nitrobenzaldehyde with a strong nucleophilic agent which may be created by reacting an aromatic mercapto compound with a strong organic or inorganic alkali metal base such as lithium hydroxide. The reaction is performed at elevated temperatures using an aprotic polar solvent. It is preferably carried out in an inert atmosphere.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: January 17, 1995
    Assignee: Orion-yhtyma Oy
    Inventors: Erkki Honkanen, Stig Lindholm
  • Patent number: 5336811
    Abstract: A process for the preparation of an aldehyde by reacting the corresponding aryl methanol with a stable free radical nitroxide in the presence of a NO.sub.x -generating compound at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the aldehyde.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: August 9, 1994
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5258544
    Abstract: Disclosed is a process for the preparation of 2-aryl-1-cyclohexene-1-carboxaldehydes from 1-arylcyclohexenes which are intermediates for trans-6-[(2-arylsubstituted cycloalkenyl and substituted cycloalkyl)alkenyl and alkyl]-3,4,5,6-tetrahydro-2H-pyran-2-ones.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: November 2, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
  • 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: 5169958
    Abstract: A process for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy or aryloxy,R.sup.2 is aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen andR.sup.3 is tetrahydrofuranyl or aryl which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and R.sup.4 and R.sup.5 are, independently of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl or aryl, with a magnesium halide of the formula IIIR.sup.3 --Mg--Y (III)where Y is halogen, at from -20.degree. to 100.degree. C., and novel .alpha.,.beta.-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: December 8, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Isak, Norbert Goetz, Thomas Kuekenhoehner
  • Patent number: RE43067
    Abstract: Produce the target substance, or a polynuclear poly(formylphenol) expressed by General Formula (2), in an industrial setting with ease and at high purity by causing a polynuclear poly(hydroxymethylphenol) or polynuclear poly(alkoxymethylphenol) to react with hexamethylene tetramine in the presence of an acid and then hydrolyzing the obtained reaction product.
    Type: Grant
    Filed: May 31, 2007
    Date of Patent: January 3, 2012
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai, Kentaro Watanabe