Aldehyde Reactant Patents (Class 568/433)
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Publication number: 20110178302Abstract: 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: ApplicationFiled: July 13, 2009Publication date: July 21, 2011Applicant: The Regents of the University of CaliforniaInventors: Nagichettiar Satyamurthy, Jorge R. Barrio
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Patent number: 7956203Abstract: 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: GrantFiled: March 27, 2001Date of Patent: June 7, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
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Publication number: 20110054175Abstract: 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: ApplicationFiled: February 2, 2009Publication date: March 3, 2011Inventors: Tobias Ritter, Takeru Furuya, Hanns M. Kaiser
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Publication number: 20110046380Abstract: 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: ApplicationFiled: April 28, 2009Publication date: February 24, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Taku Asaumi, Takashi Kamikawa
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Publication number: 20100324338Abstract: 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: ApplicationFiled: June 2, 2010Publication date: December 23, 2010Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hironori MAEDA, Yoji HORI
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Publication number: 20100311968Abstract: Organic compounds having t-butyl ester or BOC carbonate protecting groups are effectively deprotected by heating in a fluorinated alcohol solution.Type: ApplicationFiled: June 9, 2010Publication date: December 9, 2010Inventors: Jason Chi-Chung Choy, Saul Jaime-Figueroa
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Publication number: 20100276633Abstract: 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: ApplicationFiled: April 28, 2008Publication date: November 4, 2010Inventors: Martin Pick, Alan Hardwick Windle, Jose Vilatela Garcia, Krzysztof Kazimiers Koziol
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Publication number: 20100256421Abstract: 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: ApplicationFiled: March 23, 2010Publication date: October 7, 2010Applicant: O'LAUGHLIN INDUSTRIES, CO. LTD.Inventors: Zhiguo Gao, Jun Li, Xin Qi
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Publication number: 20100234630Abstract: 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: ApplicationFiled: July 11, 2008Publication date: September 16, 2010Inventors: Gerhard Steinbauer, Martina Kotthaus, Klaus Edegger, Stefaan Marie Andre De Wildeman, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries
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Publication number: 20100217027Abstract: 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: ApplicationFiled: August 28, 2008Publication date: August 26, 2010Applicant: Mitsubishi Gas Chemical Company, Inc.Inventor: Kazuo Tanaka
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Publication number: 20100204084Abstract: 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: ApplicationFiled: August 8, 2008Publication date: August 12, 2010Applicant: Givaudan SAInventors: Andreas Goeke, Yue Zou
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Publication number: 20100174105Abstract: 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: ApplicationFiled: December 31, 2009Publication date: July 8, 2010Inventors: Tak W. Leung, Gary A. Roth, Tao Tao, Kuanqiang Gao, Linfeng Chen
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Patent number: 7683191Abstract: 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: GrantFiled: February 27, 2007Date of Patent: March 23, 2010Assignee: Studiangesellschaft Kohle mbHInventors: Benjamin List, Sonja Mayer, Martin Nolwenn, Wang Xingwang
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Patent number: 7649117Abstract: 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: GrantFiled: July 24, 2008Date of Patent: January 19, 2010Assignees: National University Corporation Chiba University, Nippon Chemical Industrial Co., Ltd.Inventors: Tsuneo Imamoto, Kazuhiro Yoshida, Miwako Nishimura, Aya Koide
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Patent number: 7645908Abstract: 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: GrantFiled: September 27, 2005Date of Patent: January 12, 2010Assignee: Studiengesellschaft Kohle mbHInventors: Benjamin List, Jung Woon Yang
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Patent number: 7586009Abstract: 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: GrantFiled: February 23, 2006Date of Patent: September 8, 2009Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Akira Yoshitomo, Tatsuya Iwai
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Publication number: 20090182174Abstract: 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: ApplicationFiled: September 27, 2005Publication date: July 16, 2009Applicant: STUDIENGESELLSCHAFT KOHLE MBHInventors: Benjamin List, Jung Woon Yang
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Publication number: 20090171124Abstract: 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: ApplicationFiled: November 8, 2006Publication date: July 2, 2009Applicant: Kao CorporationInventors: Kosaku Ishida, Shigeyoshi Tanaka, Takahiro Asada
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Publication number: 20090143593Abstract: 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: ApplicationFiled: February 12, 2009Publication date: June 4, 2009Applicant: FOREST LABORATORIES HOLDINGS LIMITEDInventors: Gian-Luca Araldi, Melanie Ronsheim, Nhut Diep, Shao Hong Zhou
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Publication number: 20090076310Abstract: 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: ApplicationFiled: February 23, 2006Publication date: March 19, 2009Inventors: Akira Yoshitomo, Tatsuya Iwai
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Publication number: 20090062569Abstract: 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: ApplicationFiled: July 25, 2006Publication date: March 5, 2009Applicant: ENDURA S.P.A.Inventors: Elisa Capparella, Elisa Poluzzi, Valerio Borzatta
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Publication number: 20070232813Abstract: 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: ApplicationFiled: March 28, 2007Publication date: October 4, 2007Inventors: Coran M. H. Watanabe, Bennie John Bench
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Patent number: 7276632Abstract: 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: GrantFiled: December 14, 2004Date of Patent: October 2, 2007Assignee: BASF AktiengesellschaftInventors: Rainer Noack, Lothar Rüb, Clemens Palm
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Patent number: 7154008Abstract: 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: GrantFiled: October 14, 2004Date of Patent: December 26, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kinji Kato, Yoshihiro Shiokawa, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
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Patent number: 7145043Abstract: 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: GrantFiled: December 16, 2004Date of Patent: December 5, 2006Assignee: Ethicon, Inc.Inventor: Peter Zhu
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Patent number: 7122705Abstract: 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: GrantFiled: April 7, 2005Date of Patent: October 17, 2006Assignee: WyethInventors: Bogdan Kazimierz Wilk, Nalukui Mwisiya, Jean Louise Helom
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Patent number: 7078571Abstract: 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 mediumType: GrantFiled: October 24, 2003Date of Patent: July 18, 2006Assignee: Clariant GmbHInventors: Stefan Brand, Daniel Decker, Thomas Wessel
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Patent number: 6965055Abstract: 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: GrantFiled: November 18, 2002Date of Patent: November 15, 2005Assignee: Ajinomoto Co., Ltd.Inventors: Kenichi Mori, Shinji Fujita, Nao Funakoshi, Tadashi Takemoto
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Patent number: 6949682Abstract: 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: GrantFiled: May 28, 2004Date of Patent: September 27, 2005Assignee: Korea Research Institute of Bioscience and BiotechnologyInventors: Byoung-Mog Kwon, Kwang-Hee Son, Dong Cho Han, Sangku Lee, Jong Han Kim, Sung-Gyu Choi, Mi-Young Lee, Sun Bok Jeon
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Patent number: 6723883Abstract: 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: GrantFiled: April 15, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Jörg Therre, Andreas Kramer, Andreas Weiper-Idelmann, Michael Schulik, Regina Benfer, Jürgen Schossig, Mathias Haake, Hans-Georg Göbbel
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Patent number: 6703527Abstract: 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: GrantFiled: May 21, 2002Date of Patent: March 9, 2004Assignee: Nikken Chemicals Co., Ltd.Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
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Patent number: 6670510Abstract: 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: GrantFiled: April 18, 2002Date of Patent: December 30, 2003Assignee: Eastman Chemical CompanyInventors: Thomas Elbert Shanks, Robert Joseph Maleski
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Publication number: 20030236438Abstract: 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: ApplicationFiled: March 21, 2003Publication date: December 25, 2003Inventors: David W.C. MacMillan, Nick A. Paras
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Patent number: 6630607Abstract: 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: GrantFiled: January 24, 2002Date of Patent: October 7, 2003Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Mitsuru Hashimoto
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Publication number: 20030163004Abstract: 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: ApplicationFiled: November 18, 2002Publication date: August 28, 2003Applicant: AJINOMOTO CO., INC.Inventors: Kenichi Mori, Shinji Fujita, Nao Funakoshi, Tadashi Takemoto
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Patent number: 6596909Abstract: 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: GrantFiled: January 26, 2001Date of Patent: July 22, 2003Assignee: Mazda Motor CorporationInventors: Tuyoshi Nishijima, Osamu Takayama
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Publication number: 20030135073Abstract: 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: ApplicationFiled: January 22, 2003Publication date: July 17, 2003Inventor: Peter Zhu
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Patent number: 6531634Abstract: 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: GrantFiled: June 29, 2001Date of Patent: March 11, 2003Inventor: Peter Zhu
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Patent number: 6515137Abstract: 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: GrantFiled: July 30, 2001Date of Patent: February 4, 2003Assignee: The Regents of the University of CaliforniaInventors: David W. C. MacMillan, Kateri A. Ahrendt
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Publication number: 20030009058Abstract: 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: ApplicationFiled: April 18, 2002Publication date: January 9, 2003Inventors: Avelino Corma Canos, Sara Iborra Chornet, Maria Jose Climent Olmedo, Ruth Guil-Lopez
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Patent number: 6448409Abstract: 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: GrantFiled: November 12, 1999Date of Patent: September 10, 2002Assignee: The Regents of the University of CaliforniaInventor: Louis A. Silks, III
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Patent number: 6437190Abstract: 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: GrantFiled: November 2, 2001Date of Patent: August 20, 2002Assignee: Siemens Axiva GmbH & Co. KGInventors: Inga Leipprand, Thorsten Lahrs
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Patent number: 6433230Abstract: &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: GrantFiled: November 22, 2000Date of Patent: August 13, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
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Patent number: 6417407Abstract: 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: GrantFiled: February 10, 2000Date of Patent: July 9, 2002Assignee: Gabriel Performance Products, LLCInventors: Bao-Guo Huang, Lawrence B. Fertel
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Patent number: 6407029Abstract: 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: GrantFiled: July 17, 2000Date of Patent: June 18, 2002Assignee: Clariant GmbHInventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann, Andreas Beck, Walter Hahn
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Publication number: 20020016513Abstract: The first embodiment of the present invention provides a process, which includes:Type: ApplicationFiled: January 24, 2001Publication date: February 7, 2002Applicant: Degussa-Huels AktiengesellschaftInventors: Stephan Laue, Andreas Liese, Christian Wandrey, Olaf Burkhardt, Jens Woeltinger, Andreas Bommarius, Karlheinz Drauz, Jean-Louis Philippe, Hans Henniges, Adreas Karau
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Patent number: 6288276Abstract: 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: GrantFiled: May 2, 2000Date of Patent: September 11, 2001Assignee: Henkel Kommanditgeselschaft auf AktienInventors: Jeffrey H. Dimmit, Mark A. Kearns, William H. Chambless
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Patent number: 6184421Abstract: 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: GrantFiled: May 13, 1999Date of Patent: February 6, 2001Assignee: Rhodia ChimieInventor: Pascal Metivier
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Patent number: 6184404Abstract: 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: GrantFiled: March 1, 1999Date of Patent: February 6, 2001Assignee: Metallgesellschaft AktiengesellschaftInventors: Paul Knochel, Christian Lutz
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Patent number: 6166273Abstract: 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: GrantFiled: July 27, 1999Date of Patent: December 26, 2000Assignee: E.I. du Pont de Nemours and CompanyInventor: Munirpallam A. Subramanian