Aldehyde Reactant Patents (Class 568/433)
  • Publication number: 20110178302
    Abstract: Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO2) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18]fluoride ion derived from anhydrous [F-18](F/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me4NF, Et4NF, n-Bu4NF, (PhCH2)4NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F-18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.
    Type: Application
    Filed: July 13, 2009
    Publication date: July 21, 2011
    Applicant: The Regents of the University of California
    Inventors: Nagichettiar Satyamurthy, Jorge R. Barrio
  • Patent number: 7956203
    Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: June 7, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
  • Publication number: 20110054175
    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: February 2, 2009
    Publication date: March 3, 2011
    Inventors: Tobias Ritter, Takeru Furuya, Hanns M. Kaiser
  • Publication number: 20110046380
    Abstract: A method for producing an unsaturated organic compound represented by the formula (3): (Y1)m-1—R1—R2—(Y2)n-1??(3) wherein Y1 represents R2 or X1, and Y2 represents R1 or B(X2)2, which comprises reacting a compound represented by the formula (1): R1(X1)m??(1) wherein R1 represents an aromatic group or the like, X1 represents a leaving group and m represents 1 or 2, with a compound represented by the formula (2): R2{B(X2)2}n??(2) wherein R2 represents an aromatic group or the like, X2 represents a hydroxyl group or the like, and n represents 1 or 2, in the presence of (a) a nickel compound selected from a nickel carboxylate, nickel nitrate and a nickel halide, (b) a phosphine compound such as 1,4-bis(dicyclohexylphosphino) butane, (c) an amine selected from a primary amine and a diamine such as N,N,N?,N?-tetramethyl-1,2-ethanediamine, and (d) an inorganic base.
    Type: Application
    Filed: April 28, 2009
    Publication date: February 24, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Taku Asaumi, Takashi Kamikawa
  • Publication number: 20100324338
    Abstract: This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound.
    Type: Application
    Filed: June 2, 2010
    Publication date: December 23, 2010
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Hironori MAEDA, Yoji HORI
  • Publication number: 20100311968
    Abstract: Organic compounds having t-butyl ester or BOC carbonate protecting groups are effectively deprotected by heating in a fluorinated alcohol solution.
    Type: Application
    Filed: June 9, 2010
    Publication date: December 9, 2010
    Inventors: Jason Chi-Chung Choy, Saul Jaime-Figueroa
  • Publication number: 20100276633
    Abstract: A method of increasing the density of carbon nanotube fibres or films containing carbon nanotubes to at least 50% w/w, said method including the steps of exposing the fibre or film to suitable density enhancing agent, or to electromagnetic radiation, or by applying heat, or by mechanical compaction.
    Type: Application
    Filed: April 28, 2008
    Publication date: November 4, 2010
    Inventors: Martin Pick, Alan Hardwick Windle, Jose Vilatela Garcia, Krzysztof Kazimiers Koziol
  • Publication number: 20100256421
    Abstract: A product of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde, wherein m-tert-butylphenyl propionaldehyde is in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde. Also a method including; adding dropwise an aldehyde solution to a basic solution; and, collecting a fraction of p-tert-butyl cinnamic aldehyde m-tert-butyl cinnamic aldehyde therefrom; and, adding a transition metal catalyst to a solution of the p-tert-butyl cinnamic aldehyde in ethanol, and, collecting therefrom by distillation a product of p-tert-butylphenyl propionaldehyde and the meta isomer m-tert-butylphenyl propionaldehyde; wherein the product comprises m-tert-butylphenyl propionaldehyde in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde.
    Type: Application
    Filed: March 23, 2010
    Publication date: October 7, 2010
    Applicant: O'LAUGHLIN INDUSTRIES, CO. LTD.
    Inventors: Zhiguo Gao, Jun Li, Xin Qi
  • Publication number: 20100234630
    Abstract: This invention relates to novel alpha-substituted ?,?-unsaturated E- or Z-aldehydes, or isomer mixture thereof, of the formula (I) in which R1 and R2 may be identical or different and are each H or a hydrocarbon, in which the hydrocarbon may have one or more heteroatoms and R3 and R4 may be identical or different and are each a hydrocarbon, in which the hydrocarbon may have one or more heteroatoms, and R5 may be identical or different and is H or a hydrocarbon, in which the hydrocarbon may have one or more heteroatoms, to the use thereof, and to processes for their preparation. The invention further relates to the preparation of further intermediates for pharmaceuticals and to the preparation of the pharmaceuticals.
    Type: Application
    Filed: July 11, 2008
    Publication date: September 16, 2010
    Inventors: Gerhard Steinbauer, Martina Kotthaus, Klaus Edegger, Stefaan Marie Andre De Wildeman, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries
  • Publication number: 20100217027
    Abstract: A process in which a phenol derivative is iodinated to produce a 2-iodophenol or 2,6-diiodophenol derivative substituted with iodine at an ortho position thereof is provided, which does not require any step of recovery of iodine but can produce it at low cost, in high yield and with high quality. A phenol derivative is mixed with a pyridine and hydrogen peroxide or iodic acid as an oxidizing agent, and reacted with molecular iodine. As a result, iodination can be performed very efficiently with iodine in an amount close to the theoretical amount relative to the phenol derivative, and the 2-iodophenol or 2,6-diiodophenol derivative can be obtained in high yield and with high quality.
    Type: Application
    Filed: August 28, 2008
    Publication date: August 26, 2010
    Applicant: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Kazuo Tanaka
  • Publication number: 20100204084
    Abstract: The present invention relates to a process for the production of formyl cyclohexene derivatives which are suitable as odorants as such or as intermediates for the preparation of further odorants.
    Type: Application
    Filed: August 8, 2008
    Publication date: August 12, 2010
    Applicant: Givaudan SA
    Inventors: Andreas Goeke, Yue Zou
  • Publication number: 20100174105
    Abstract: The present disclosure is directed to the production of 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate and the purification thereof. Synthesis pathways for a precursor to 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate are provided. The precursor is 5-tert-butyl-3-methylcatechol.
    Type: Application
    Filed: December 31, 2009
    Publication date: July 8, 2010
    Inventors: Tak W. Leung, Gary A. Roth, Tao Tao, Kuanqiang Gao, Linfeng Chen
  • Patent number: 7683191
    Abstract: The invention relates to a method for producing chiral organic compounds by asymmetric catalysis, using ionic catalysts comprising a chiral catalyst anion. The claimed method is suitable for reactions which are carried out over cationic intermediate stages, such as iminium ions or acyl pyridinium ions. The invention enables the production of chiral compounds with high ee values, that until now could only be obtained by means of costly purification methods.
    Type: Grant
    Filed: February 27, 2007
    Date of Patent: March 23, 2010
    Assignee: Studiangesellschaft Kohle mbH
    Inventors: Benjamin List, Sonja Mayer, Martin Nolwenn, Wang Xingwang
  • Patent number: 7649117
    Abstract: Disclosed is a process of preparing an optically active ?-hydroxycarboxylic acid derivative comprising asymmetrically hydrogenating a ?-keto compound in the presence of a catalyst comprising a transition metal complex compound having a 2,3-bis(dialkylphosphino)pyrazine derivative as a ligand. The pyrazine derivative is preferably a quinoxaline derivative, and the transition metal is preferably ruthenium. Preferred examples of the quinoxaline derivative are (S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline, (R,R)-bis(tert-butylmethylphosphino)quinoxaline, (S,S)-bis(tert-adamantylmethylphosphino)quinoxaline, and (R,R)-bis(adamantylmethylphosphino)quinoxaline.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: January 19, 2010
    Assignees: National University Corporation Chiba University, Nippon Chemical Industrial Co., Ltd.
    Inventors: Tsuneo Imamoto, Kazuhiro Yoshida, Miwako Nishimura, Aya Koide
  • Patent number: 7645908
    Abstract: A method for the chemoselective hydrogenation of ?, ? unsaturated carbonyl compounds is disclosed, in which compounds of the formula R4R3C?CR2—C(O)R1, wherein R1—R4 are as defined herein, are reacted with a hybrid donor to form a compound of formula R4R3CH—CH(R2)—C(O)R1, in which R1—R4 are as above. That method permits the selective hydrogenation of ?, ? unsaturated aldehydes and ketones without the use of metal catalysts.
    Type: Grant
    Filed: September 27, 2005
    Date of Patent: January 12, 2010
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Benjamin List, Jung Woon Yang
  • Patent number: 7586009
    Abstract: Provide a new bis-(hydroxybenzaldehyde) compound, as well as a new polynuclear polyphenol compound derived therefrom, suitable for use as component materials for photosensitive resist compositions, component materials and hardeners for epoxy resins, developers and anti-fading agents used in thermosensitive recording materials, bactericides, fungicides, antioxidants and other functional chemical products or component materials thereof, wherein such bis-(hydroxybenzaldehyde) compound is produced by reacting in the presence of trihalogenated acetic acid catalyst or phosphoric acid catalyst a 2,6-di(hydroxymethyl)-4-alkylphenol with a hydroxybenzaldehyde expressed by general formula (14).
    Type: Grant
    Filed: February 23, 2006
    Date of Patent: September 8, 2009
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai
  • Publication number: 20090182174
    Abstract: A method for the chemoselective hydrogenation of ?, ? unsaturated carbonyl compounds is disclosed, in which compounds of the formula R4R3C?CR2—C(O)R1, wherein R1-R4 are as defined herein, are reacted with a hybrid donor to form a compound of formula R4R3CH—CH(R2)—C(O)R1, in which R1-R4 are as above. That method permits the selective hydrogenation of ?, ? unsaturated aldehydes and ketones without the use of metal catalysts.
    Type: Application
    Filed: September 27, 2005
    Publication date: July 16, 2009
    Applicant: STUDIENGESELLSCHAFT KOHLE MBH
    Inventors: Benjamin List, Jung Woon Yang
  • Publication number: 20090171124
    Abstract: The present invention relates to processes for producing ?,?-unsaturated aldehyde compounds and unsaturated alcohols with a good yield. There is provided a process for producing and ?,?-unsaturated aldehyde compound including the step of subjecting a raw aldehyde compound to an intermolecular condensation reaction in the presence of an amine and a protonic acid having 4 to 20 carbon atoms or a salt thereof; and a process for producing an unsaturated alcohol including the step of subjecting the ?,?-unsaturated aldehyde compound to a reduction reaction.
    Type: Application
    Filed: November 8, 2006
    Publication date: July 2, 2009
    Applicant: Kao Corporation
    Inventors: Kosaku Ishida, Shigeyoshi Tanaka, Takahiro Asada
  • Publication number: 20090143593
    Abstract: Methods for the synthesis of heterocyclic compounds including N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo[b,d]furan-1-carboxamide and pharmaceutically acceptable salts thereof.
    Type: Application
    Filed: February 12, 2009
    Publication date: June 4, 2009
    Applicant: FOREST LABORATORIES HOLDINGS LIMITED
    Inventors: Gian-Luca Araldi, Melanie Ronsheim, Nhut Diep, Shao Hong Zhou
  • Publication number: 20090076310
    Abstract: Provide a new bis-(hydroxybenzaldehyde) compound, as well as a new polynuclear polyphenol compound derived therefrom, suitable for use as component materials for photosensitive resist compositions, component materials and hardeners for epoxy resins, developers and anti-fading agents used in thermosensitive recording materials, bactericides, fungicides, antioxidants and other functional chemical products or component materials thereof, wherein such bis-(hydroxybenzaldehyde) compound is produced by reacting in the presence of trihalogenated acetic acid catalyst or phosphoric acid catalyst a 2,6-di(hydroxymethyl)-4-alkylphenol with a hydroxybenzaldehyde expressed by general formula (14).
    Type: Application
    Filed: February 23, 2006
    Publication date: March 19, 2009
    Inventors: Akira Yoshitomo, Tatsuya Iwai
  • Publication number: 20090062569
    Abstract: A new process for synthesizing 3,4-dioxo-substituted aromatic aldehydes by Oppenauer oxidation of the corresponding benzyl alcohols is described. The process, which specifically uses formaldehyde as hydrogen acceptor, proceeds with unexpectedly high yields and conversion percentages, allowing low cost access to finished and intermediate products of high industrial interest in the field of pharmaceutical products and fragrances.
    Type: Application
    Filed: July 25, 2006
    Publication date: March 5, 2009
    Applicant: ENDURA S.P.A.
    Inventors: Elisa Capparella, Elisa Poluzzi, Valerio Borzatta
  • Publication number: 20070232813
    Abstract: The present invention is generally directed to the use of L-proline and certain derivatives thereof to catalyze the asymmetric self-condensation of ?,?-unsaturated aldehydes to form homodimer and heterodimer cyclohexadienals. Reaction conditions are mild and yet amenable to a variety of different substrates yielding molecules with complex scaffolds from simple precursors. This approach allows for diversification and synthesis of this structural class of compounds in sufficient quantity, purity and enantioselectivity for, e.g., biological investigations and use as fluorescent probes, anti-cancer agents, anti-bacterial agents, and/or anti-fungal agents. The present invention is also generally directed to the cyclohexadienals produced.
    Type: Application
    Filed: March 28, 2007
    Publication date: October 4, 2007
    Inventors: Coran M. H. Watanabe, Bennie John Bench
  • Patent number: 7276632
    Abstract: The invention relates to a method for producing 2,3-cis-substituted 2-aryl propenals by condensing a 2-aryl acetaldehyde I with a non-enolizable aldehyde compound II in the presence of a base. The inventive method is characterized in that the reaction is carried out in a solvent mixture comprising at least one water-miscible organic solvent and water at a volume ratio Vsolvent:Vwater ranging between 10:1 and 0.5:1.
    Type: Grant
    Filed: December 14, 2004
    Date of Patent: October 2, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Noack, Lothar Rüb, Clemens Palm
  • Patent number: 7154008
    Abstract: In the production of an alkylbenzaldehyde by a method comprising a step of preparing a solution of complex of a starting alkylbenzene and a hydrogen fluoride-boron trifluoride catalyst and a step of formylation by bringing the solution of complex into contact with carbon monoxide, an alkylbenzene having at least one primary alkyl group having two or more carbon atoms on its benzene ring is used as the starting alkylbenzene. The preparation of the solution of complex is carried out in the presence of an aliphatic or alicyclic saturated hydrocarbon having 6 to 10 carbon atoms which contains at least one tertiary carbon atom but contains no quaternary carbon atom. By the combined use of the specific alkylbenzene and the aliphatic or alicyclic saturated hydrocarbon, the disproportionation of the alkylbenzene is prevented and the alkylbenzaldehyde is produced at high yields.
    Type: Grant
    Filed: October 14, 2004
    Date of Patent: December 26, 2006
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kinji Kato, Yoshihiro Shiokawa, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
  • Patent number: 7145043
    Abstract: Methods, compositions, and devices for alleviating the problems of toxic discharge of aldehydes present in waste streams are disclosed. The methods relate to forming neutralized aldehydes by treating aldehydes with oxidizing agents. The oxidizing agents offer a simple, effective, fast and inexpensive solution for treatment of toxic aldehydes prior to disposal into the environment.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: December 5, 2006
    Assignee: Ethicon, Inc.
    Inventor: Peter Zhu
  • Patent number: 7122705
    Abstract: Processes for coupling phenol and cycloalkyls including combining an optionally substituted phenol, a cycloalkyl substituted with a leaving group, carbonate salt, tetrahydrofuran, and an optional phase transfer agent are provided. Also provided are processes for preparing 3-cyclopentyloxy-4-methoxybenzaldehyde by combining 3-hydroxy-4-methoxybenzaldehyde, a cyclopentyl compound, a carbonate salt, a solvent, and an optional phase transfer agent.
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: October 17, 2006
    Assignee: Wyeth
    Inventors: Bogdan Kazimierz Wilk, Nalukui Mwisiya, Jean Louise Helom
  • Patent number: 7078571
    Abstract: A process for preparing 1,3-di-halo-substituted benzene derivatives (II) from 2,6-di-halo-substituted benzaldehydes (I) (where X1, X2 are each independently F, Cl, Br, and R1, R2, R3 are each independently H, halogen, OH, C1–C12-alkyl, CF3, CHO, C6–C14-aryl, Oalkyl, Oaryl, NO2) by reacting with an alkaline medium, which comprises initially charging the alkaline medium and metering in the 2,6-di-halo-substituted benzaldehyde (I) or initially charging the 2,6-di-halo-substituted benzaldehyde (I) and metering in the alkaline medium
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: July 18, 2006
    Assignee: Clariant GmbH
    Inventors: Stefan Brand, Daniel Decker, Thomas Wessel
  • Patent number: 6965055
    Abstract: A process for conveniently and efficiently producing a highly pure cinnamaldehyde derivative, for example, (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde, which comprises reacting a benzaldehyde derivative, such as isovanillin and the like, with acetaldehyde in the presence of an alkali, in particular preferably, dropping acetaldehyde little by little thereto in an aqueous solution at a low temperature for the reaction thereof. The cinnamaldehyde derivative thus obtained is selectively reduced to produce 3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propionaldehyde. Further, through a reductive alkylation reaction of the compound thus produced with an aspartame, N-[N-[3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high sweetening potency, can be industrially and efficiently produced. The processes therefor are also provided.
    Type: Grant
    Filed: November 18, 2002
    Date of Patent: November 15, 2005
    Assignee: Ajinomoto Co., Ltd.
    Inventors: Kenichi Mori, Shinji Fujita, Nao Funakoshi, Tadashi Takemoto
  • Patent number: 6949682
    Abstract: The present invention relates to cinnamaldehyde derivatives inhibiting growth of tumor cell and regulating cell cycle, the method for preparation and the pharmaceutical composition thereof. The cinnamaldehyde derivatives of the present invention can be effectively used as a cell cycle regulator or a cancer cell growth inhibitor, since it has an ability to regulate cell cycle by holding the cells in G2/M stage of the cell division and has activity to inhibit cancer cell growth.
    Type: Grant
    Filed: May 28, 2004
    Date of Patent: September 27, 2005
    Assignee: Korea Research Institute of Bioscience and Biotechnology
    Inventors: Byoung-Mog Kwon, Kwang-Hee Son, Dong Cho Han, Sangku Lee, Jong Han Kim, Sung-Gyu Choi, Mi-Young Lee, Sun Bok Jeon
  • Patent number: 6723883
    Abstract: The present invention relates to a continuous process for the preparation of cinnamaldehyde or cinnamaldehyde derivatives by continuous reaction of benzaldehyde derivatives with alkanals in the presence of bases and optionally subsequent continuous hydrogenation in a circulation reactor in the presence of a suspension catalyst and hydrogen to give dihydrocinnamaldehyde derivatives.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: April 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Jörg Therre, Andreas Kramer, Andreas Weiper-Idelmann, Michael Schulik, Regina Benfer, Jürgen Schossig, Mathias Haake, Hans-Georg Göbbel
  • Patent number: 6703527
    Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.
    Type: Grant
    Filed: May 21, 2002
    Date of Patent: March 9, 2004
    Assignee: Nikken Chemicals Co., Ltd.
    Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
  • Patent number: 6670510
    Abstract: The present invention recites a process for the of 2,5-dimethoxy-benzaldehyde by reacting a 2-hydroxy-5 methoxy-benzaldehyde with a suitable metal hydroxide in the presence of a suitable solvent to make a metal salt of 2-hydroxy-5-methoxy benzaldehyde comprising. The invention further provides a method for alkylating said metal salts with dimethylsulfate in the presence of a suitable solvent so as to provide a 2,5-dimethoxy benzaldehyde.
    Type: Grant
    Filed: April 18, 2002
    Date of Patent: December 30, 2003
    Assignee: Eastman Chemical Company
    Inventors: Thomas Elbert Shanks, Robert Joseph Maleski
  • Publication number: 20030236438
    Abstract: Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-addition of an aromatic nucleophile to an &agr;,&bgr;-unsaturated aldehyde. The aromatic nucleophile may be an N,N-disubstituted aniline compound, or an analog thereof. The reaction is efficient and enantioselective, and proceeds with a variety of substituted and unsubstituted aromatic nucleophiles and aldehydes. The invention also provides a method for the deamination of aromatic N,N-disubstituted amines such as those resulting from the 1,4-addition of an aromatic nucleophile to an &agr;,&bgr;-unsaturated aldehyde.
    Type: Application
    Filed: March 21, 2003
    Publication date: December 25, 2003
    Inventors: David W.C. MacMillan, Nick A. Paras
  • Patent number: 6630607
    Abstract: Aromatic methylidene compounds of the following general formula wherein R11 and R21 independently in each occurrence represent an unsubstituted or substituted alkyl or alkoxy group, a halogen, a cyano group or a nitro group, n11 and n21 are, respectively, an integer, R31 and R41 independently represent hydrogen, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted aromatic group, or an unsubstituted or substituted aromatic heterocyclic group and may join to complete a condensed ring, along with other types of aromatic methylidene compounds wherein the moieties attached to the naphthalene ring are attached to different positions of the ring. The preparation of the methylidene compounds is also described along with intermediate compounds and their preparation.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: October 7, 2003
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Mitsuru Hashimoto
  • Publication number: 20030163004
    Abstract: A process for conveniently and efficiently producing a highly pure cinnamaldehyde derivative, for example, (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde, which comprises reacting a benzaldehyde derivative, such as isovanillin and the like, with acetaldehyde in the presence of an alkali, in particular preferably, dropping acetaldehyde little by little thereto in an aqueous solution at a low temperature for the reaction thereof. The cinnamaldehyde derivative thus obtained is selectively reduced to produce 3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propionaldehyde. Further, through a reductive alkylation reaction of the compound thus produced with an aspartame, N-[N-[3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high sweetening potency, can be industrially and efficiently produced. The processes therefor are also provided.
    Type: Application
    Filed: November 18, 2002
    Publication date: August 28, 2003
    Applicant: AJINOMOTO CO., INC.
    Inventors: Kenichi Mori, Shinji Fujita, Nao Funakoshi, Tadashi Takemoto
  • 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: 20030135073
    Abstract: Methods, compositions, and devices for alleviating the problems of toxic discharge of aldehydes present in waste streams are disclosed. The methods relate to forming neutralized aldehydes by treating aldehydes with oxidizing agents. The oxidizing agents offer a simple, effective, fast and inexpensive solution for treatment of toxic aldehydes prior to disposal into the environment.
    Type: Application
    Filed: January 22, 2003
    Publication date: July 17, 2003
    Inventor: Peter Zhu
  • Patent number: 6531634
    Abstract: Methods, compositions, and devices for alleviating the problems of toxic discharge of aldehydes present in waste streams are disclosed. The methods relate to forming neutralized aldehydes by treating aldehydes with oxidizing agents. The oxidizing agents offer a simple, effective, fast and inexpensive solution for treatment of toxic aldehydes prior to disposal into the environment.
    Type: Grant
    Filed: June 29, 2001
    Date of Patent: March 11, 2003
    Inventor: Peter Zhu
  • Patent number: 6515137
    Abstract: Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
    Type: Grant
    Filed: July 30, 2001
    Date of Patent: February 4, 2003
    Assignee: The Regents of the University of California
    Inventors: David W. C. MacMillan, Kateri A. Ahrendt
  • Publication number: 20030009058
    Abstract: Heterogeneous acid catalysts are used in a process for the selective obtainment of &agr;-alkylcinnamaldehydes, and more specifically Jasmine aldehyde, by direct reaction between n-alkylaldehydes and benzaldehyde or a benzaldehyde substituted in its aromatic ring: aluminum phosphates (AlPO), silicoaluminophosphates (SAPO), and silicoaluminates (MAS) or basic catalysts corresponding to nitrides of such acid catalysts: oxynitrided aluminum phosphates (AlPON), oxynitrided silicoaluminophosphates (SAPON) and oxynitrided silicoaluminates (SAMON).
    Type: Application
    Filed: April 18, 2002
    Publication date: January 9, 2003
    Inventors: Avelino Corma Canos, Sara Iborra Chornet, Maria Jose Climent Olmedo, Ruth Guil-Lopez
  • Patent number: 6448409
    Abstract: Molecules containing a chiral 1,2-diol unit are synthesized from reactions between aldehydes and N-acyl selones. A chilled N-acyl selone is reacted with a Lewis acid such as TiCl4 and mixed with a tertiary amine such as diisopropylethylamine to generate an enolate solution. Upon further chilling of the enolate solution a desired aldehyde is added and after an acceptable reaction period a quencher is introduced and the product isolated.
    Type: Grant
    Filed: November 12, 1999
    Date of Patent: September 10, 2002
    Assignee: The Regents of the University of California
    Inventor: Louis A. Silks, III
  • Patent number: 6437190
    Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: August 20, 2002
    Assignee: Siemens Axiva GmbH & Co. KG
    Inventors: Inga Leipprand, Thorsten Lahrs
  • Patent number: 6433230
    Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising: reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: August 13, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
  • Patent number: 6417407
    Abstract: A 2-bromo-4-chloro substituted phenol is prepared from a first composition of a substituted phenol and benzotrifluoride in a weight ratio to the substituted phenol of about 2 to about 4. Into the first composition is sparged about 1 to about 1.5 equivalents of chlorine gas, whereby the substituted phenol is chlorinated to form a 4-chloro substituted phenol. The first composition is cooled to precipitate the 4-chloro substituted phenol, which can be isolated by filtration. A second composition is formed of the 4-chloro substituted phenol, acetic acid in an weight ratio to the 4-chloro substituted phenol of about 1 to about 2, about 1 to about 2 equivalents of a salt of a strong base and a weak acid, and about 1 to about 5 equivalents of a brominating agent, whereby the 4-chloro substituted phenol is brominated to form a 2-bromo-4-chloro substituted phenol.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: July 9, 2002
    Assignee: Gabriel Performance Products, LLC
    Inventors: Bao-Guo Huang, Lawrence B. Fertel
  • Patent number: 6407029
    Abstract: The present invention relates to mixtures comprising from 70 to 99.5% by weight of a compound of the formula (R)4P+X− (1) and from 30 to 0.5% by weight of a compound of the formula (R)3P═O (2), where R is in each case a radical and X− is an inorganic or organic anion or the equivalent of a multiply charged inorganic or organic anion, also to a process for preparing the mixtures by reacting a phosphorus pentahalide with pyrrolidine or piperidine in the molar ratio 1:6 to 1:50 in the presence of an inert solvent initially at −20 to 80° C., subsequently continuing the reaction at 90 to 180° C., treating the resulting reaction product at 0 to 80° C. with aqueous alkali at a pH of 7 to 15, and separating aqueous and organic phase from one another, and to the use of the mixtures as catalyst and cocatalyst for phase-transfer reactions, nucleophilic substitution reactions or halogen-fluorine exchange reactions.
    Type: Grant
    Filed: July 17, 2000
    Date of Patent: June 18, 2002
    Assignee: Clariant GmbH
    Inventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann, Andreas Beck, Walter Hahn
  • Publication number: 20020016513
    Abstract: The first embodiment of the present invention provides a process, which includes:
    Type: Application
    Filed: January 24, 2001
    Publication date: February 7, 2002
    Applicant: Degussa-Huels Aktiengesellschaft
    Inventors: Stephan Laue, Andreas Liese, Christian Wandrey, Olaf Burkhardt, Jens Woeltinger, Andreas Bommarius, Karlheinz Drauz, Jean-Louis Philippe, Hans Henniges, Adreas Karau
  • Patent number: 6288276
    Abstract: Process for making Oximes of the formula IV wherein each of R2-R5 is hydrogen, a halogen, an alkyl or cycloalkyl group having from 1 to 36 carbon atoms, an aryl or alkaryl group having from 1 to 36 carbon atoms, an alkoxy or an aryloxy group having from 1 to 30 carbon atoms, an acyl group having from 1 to 24 carbon atoms and intermediates leading thereto are described.
    Type: Grant
    Filed: May 2, 2000
    Date of Patent: September 11, 2001
    Assignee: Henkel Kommanditgeselschaft auf Aktien
    Inventors: Jeffrey H. Dimmit, Mark A. Kearns, William H. Chambless
  • Patent number: 6184421
    Abstract: The present invention concerns a process for the preparation of a 4-hydroxybenzaldehyde and its derivatives. More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as vanillin and ethylvanillin.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: February 6, 2001
    Assignee: Rhodia Chimie
    Inventor: Pascal Metivier
  • Patent number: 6184404
    Abstract: There is described a process for the enantioselective alkylation of aldehydes by means of organozinc compounds, of which a ligand of the zinc is transferred to the aldehyde, and the other ligand acts as so-called dummy ligand. As novel substances there are used zinc-organic compounds, which contain the neophyl residue as dummy ligand.
    Type: Grant
    Filed: March 1, 1999
    Date of Patent: February 6, 2001
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Paul Knochel, Christian Lutz
  • Patent number: 6166273
    Abstract: A process is provided for increasing the fluorine content of benzene or pyridine rings which are optionally substituted with from 1 to 3 inert substituents. The process involves (a) contacting the ring with a metal fluoride composition comprising cupric fluoride (CuF.sub.2) at a temperature above 250.degree. C. sufficient to transfer F from cupric fluoride to the optionally substituted ring, thereby chemically reducing the metal fluoride composition; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate a metal fluoride composition comprising cupric fluoride; and (c) employing regenerated metal fluoride composition of (b) in (a).
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: December 26, 2000
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Munirpallam A. Subramanian