Halogen Containing Reactant Patents (Class 568/437)
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Patent number: 9498448Abstract: The present invention provides a process for purifying a monoterpene or sesquiterpene having a purity greater than about 98.5% (w/w). The process comprises the steps of derivatizing the monoterpene (or sesquiterpene) to produce a monoterpene (or sesquiterpene) derivative, separating the monoterpene (or sesquiterpene) derivative, and releasing the monoterpene (or sesquiterpene) from the derivative. Also encompassed by the scope of the present invention is a pharmaceutical composition comprising a monoterpene (or sesquiterpene) having a purity greater than about 98.5% (w/w). The purified monoterpene can be used to treat a disease such as cancer. The present monoterpene (or sesquiterpene) may be administered alone, or may be co-administered with radiation or other therapeutic agents, such as chemotherapeutic agents.Type: GrantFiled: September 2, 2015Date of Patent: November 22, 2016Assignee: NeOne Technologies, Inc.Inventors: Thomas Chen, Daniel Levin, Satish Puppali
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Patent number: 9480659Abstract: The present invention provides a process for purifying a monoterpene or sesquiterpene having a purity greater than about 98.5% (w/w). The process comprises the steps of derivatizing the monoterpene (or sesquiterpene) to produce a monoterpene (or sesquiterpene) derivative, separating the monoterpene (or sesquiterpene) derivative, and releasing the monoterpene (or sesquiterpene) from the derivative. Also encompassed by the scope of the present invention is a pharmaceutical composition comprising a monoterpene (or sesquiterpene) having a purity greater than about 98.5% (w/w). The purified monoterpene can be used to treat a disease such as cancer. The present monoterpene (or sesquiterpene) may be administered alone, or may be co-administered with radiation or other therapeutic agents, such as chemotherapeutic agents.Type: GrantFiled: August 4, 2015Date of Patent: November 1, 2016Assignee: NeOnc Technologies, Inc.Inventors: Thomas Chen, Daniel Levin, Satish Puppali
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Patent number: 9029606Abstract: A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.Type: GrantFiled: June 27, 2012Date of Patent: May 12, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
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Patent number: 8937200Abstract: A new process capable of producing a 2-(aryloxymethyl)benzaldehyde compound is provided. More particularly, a process for producing a 2-(aryloxymethyl)benzaldehyde compound represented by formula (2) comprising a step of hydrolyzing a compound represented by following formula (1); wherein X1 and X2 each represent independently a chlorine atom, a bromine atom or an iodine atom, Q1, Q2, Q3 and Q4 each represent independently a hydrogen atom or a halogen atom, and Ar represents a phenyl group optionally having a substituent.Type: GrantFiled: June 27, 2012Date of Patent: January 20, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Masaji Hirota, Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
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Publication number: 20140228579Abstract: The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.Type: ApplicationFiled: September 11, 2013Publication date: August 14, 2014Applicant: Brock UnviersityInventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
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Publication number: 20140221695Abstract: A new process capable of producing a 2-(aryloxymethyl)benzaldehyde compound is provided. More particularly, a process for producing a 2-(aryloxymethyl)benzaldehyde compound represented by formula (2) comprising a step of hydrolyzing a compound represented by following formula (1); wherein X1 and X2 each represent independently a chlorine atom, a bromine atom or an iodine atom, Q1, Q2, Q3 and Q4 each represent independently a hydrogen atom or a halogen atom, and Ar represents a phenyl group optionally having a substituent.Type: ApplicationFiled: June 27, 2012Publication date: August 7, 2014Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masaji Hirota, Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
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Publication number: 20140187822Abstract: A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.Type: ApplicationFiled: June 27, 2012Publication date: July 3, 2014Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
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Patent number: 8742187Abstract: The method of the present invention provides a high yield pathway to 2,5-dimethylhexadiene from renewable isobutanol, which enables economic production of renewable p-xylene (and subsequently, terephthalic acid, a key monomer in the production of PET) from isobutanol. In addition, the present invention provides methods for producing 2,5-dimethylhexadiene from a variety of feed stocks that can act as “equivalents” of isobutylene and/or isobutyraldehyde including isobutanol, isobutylene oxide, and isobutyl ethers and acetals. Catalysts employed in the present methods that produce 2,5-dimethylhexadiene can also catalyze alcohol dehydration, alcohol oxidation, epoxide rearrangement, and ether and acetal cleavage.Type: GrantFiled: April 19, 2012Date of Patent: June 3, 2014Assignee: GEVO, Inc.Inventors: Thomas Jackson Taylor, Joshua D. Taylor, Matthew W. Peters, David E. Henton
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Patent number: 8692026Abstract: 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: GrantFiled: July 1, 2011Date of Patent: April 8, 2014Assignee: Albemarle CorporationInventors: Thierry J. Giard, Vincent L. Mutterer, Christophe Durvaux
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Publication number: 20130259804Abstract: The present invention relates to improved radiotracer imaging agent compositions, which comprises 18F-labelled biological targeting moieties, wherein impurities which affect imaging in vivo are identified and suppressed. Also provided are radiopharmaceuticals comprising said improved compositions, together with radiofluorinated aldehyde compositions useful in preparing said radiotracer compositions. The invention also includes methods of imaging and/or diagnosis using the radiopharmaceutical compositions described.Type: ApplicationFiled: December 9, 2011Publication date: October 3, 2013Applicant: GE HEALTHCARE LIMITEDInventors: Torgrim Engell, Julian Grigg, Dimtrios Mantzilas
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Patent number: 8399710Abstract: An alkali metal fluoride dispersion of an alkali metal fluoride and an aprotic organic solvent is obtainable by (A) separating a liquid phase from an alkali metal fluoride dispersion comprising an alcohol solvent and an alkali metal fluoride, and mixing the separated liquid phase with an aprotic organic solvent having a boiling point of 85° C. or higher at normal pressure; (B) obtaining a mixture containing the alkali metal fluoride by (b1) concentrating the mixture containing the alkali metal fluoride to obtain a concentrated fraction and a concentrated residue; (b2) mixing a residue of the alkali metal fluoride dispersion with the concentrated fraction obtained in (b1); and (b3) separating a liquid phase from the mixture containing an alkali metal fluoride obtained in (b2) and mixing the separated liquid phase with the concentrated residue; and (C) removing the alcohol solvent from the mixture containing the alkali metal fluoride.Type: GrantFiled: August 27, 2008Date of Patent: March 19, 2013Assignee: Sumitomo Chemical Company, LimitedInventor: Koji Hagiya
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Patent number: 8350091Abstract: A potassium fluoride dispersion essentially consisting of potassium fluoride and an aprotic organic solvent having a boiling point higher than that of methanol, which is obtainable by mixing a mixture containing potassium fluoride and 5 to 50 parts by weight of methanol per 1 part by weight of potassium fluoride with the aprotic organic solvent followed by concentrating the obtained mixture, and a process for producing a fluorine-containing organic compound comprising contacting an organic compound having at least one group capable of being substituted nucleophilically with a fluorine atom with the potassium fluoride dispersion.Type: GrantFiled: December 30, 2011Date of Patent: January 8, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Kazuaki Sasaki
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Patent number: 8338649Abstract: The invention relates to a method for the production of an aromatic carbonyl compound by the oxidation of a methyl group or methylene group bonded to the aromatic group in which the aromatic substance is reacted in the presence of an oxidizing agent and a sulphoxide, a sulphoxide being selected for the oxidation of a specific aromatic substance whose ionization potential, in terms of magnitude, differs from the ionization potential of the aromatic substance to be oxidized by a maximum of ±0.25 eV.Type: GrantFiled: September 2, 2008Date of Patent: December 25, 2012Assignee: Weylchem Frankfurt GmbHInventors: Klaus Forstinger, Thomas Sommer, Daniel Decker, Andreas Martin, Angela Köckritz, Michael Kant, Alexander Hofmann
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Patent number: 8258349Abstract: A benzaldehyde acetal compound of formula (3): (wherein Q represents a hydrogen atom or a halogen atom, Ar represents a phenyl group optionally substituted with at least one selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and halogen atoms, and R represents an alkyl group having 1 to 4 carbon atoms).Type: GrantFiled: January 30, 2009Date of Patent: September 4, 2012Assignee: Suitomo Chemical Company, LimitedInventor: Koichi Nakazawa
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Publication number: 20120165548Abstract: Processes for the preparation of Silodosin and its intermediates comprising reductive amination of compound of Formula (VIII) with a compound of Formula (VII) or a compound of Formula (XV) in a suitable solvent using a reducing agent.Type: ApplicationFiled: September 13, 2010Publication date: June 28, 2012Applicant: SANDOZ AGInventors: Shreerang Joshi, Sachin Bhuta, Sanjay Talukdar, Sudhir Sawant, Deepak Venkataraman, Abhinay Pise, Shashikant Metkar, Dattatraya Chavan, Parven Kumar Luthra
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Patent number: 7994367Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (4): wherein Q1 and Q2 represent an alkyl group etc., n represents 1 or 2, and Ar represents a phenyl group etc., including the steps of reacting a compound represented by the formula (3): wherein X1 represents a chlorine atom etc., and Q1, Q2, n and Ar are respectively the same meaning as above, with magnesium metal to obtain a Grignard compound and then reacting the obtained Grignard compound with a formylating agent.Type: GrantFiled: May 14, 2008Date of Patent: August 9, 2011Assignee: Sumitomo Chemical Company, LimitedInventor: Koichi Nakazawa
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Publication number: 20110098489Abstract: A method of producing a corresponding acetal compound which comprises reacting a benzal halide compound represented by formula (1) (wherein, Q represents a hydrogen atom or a halogen atom, X represents a halogen atom, and Ar represents a phenyl group optionally substituted with at least one group selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and halogen atoms.) and an alcohol compound in the presence of at least one alkaline earth metal compound selected from the group consisting of alkaline earth metal oxides, alkaline earth metal hydroxides and alkaline earth metal carbonates.Type: ApplicationFiled: June 9, 2009Publication date: April 28, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Yoshio Onogawa, Kazuyoshi Yamanaka, Masaji Hirota
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Patent number: 7851659Abstract: 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: GrantFiled: May 14, 2008Date of Patent: December 14, 2010Assignee: Sumitomo Chemical Company, LimitedInventor: Koichi Nakazawa
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Publication number: 20100312017Abstract: The invention relates to a method for the production of an aromatic carbonyl compound by the oxidation of a methyl group or methylene group bonded to the aromatic group in which the aromatic substance is reacted in the presence of an oxidising agent and a sulphoxide, a sulphoxide being selected for the oxidation of a specific aromatic substance whose ionisation potential, in terms of magnitude, differs from the ionisation potential of the aromatic substance to be oxidised by a maximum of ±0.25 eV.Type: ApplicationFiled: September 2, 2008Publication date: December 9, 2010Inventors: Klaus Forstinger, Thomas Sommer, Daniel Decker, Andreas Martin, Angela Köckritz, Michael Kant, Alexander Hofmann
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Publication number: 20100292513Abstract: A benzaldehyde acetal compound of formula (3): (wherein Q represents a hydrogen atom or a halogen atom, Ar represents a phenyl group optionally substituted with at least one selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and halogen atoms, and R represents an alkyl group having 1 to 4 carbon atoms).Type: ApplicationFiled: January 30, 2009Publication date: November 18, 2010Inventor: Koichi Nakazawa
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Patent number: 7790931Abstract: 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: GrantFiled: June 12, 2006Date of Patent: September 7, 2010Assignee: Showa Denko K.K.Inventors: Haruhiko Ikeda, Hideo Miyata, Katsutoshi Ohno, Katsuro Urakawa
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Publication number: 20100210879Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (4): wherein Q1 and Q2 represent an alkyl group etc., n represents 1 or 2, and Ar represents a phenyl group etc., including the steps of reacting a compound represented by the formula (3): wherein X1 represents a chlorine atom etc., and Q1, Q2, n and Ar are respectively the same meaning as above, with magnesium metal to obtain a Grignard compound and then reacting the obtained Grignard compound with a formylating agent.Type: ApplicationFiled: May 14, 2008Publication date: August 19, 2010Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Koichi Nakazawa
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Publication number: 20100130758Abstract: Disclosed are a catalyst including a hydrotalcite and, immobilized on a surface thereof, particles of at least one metal selected from the group consisting of Cu, Ag, and Au; a method for producing a carbonyl compound through dehydrogenation of an alcohol in the presence of the catalyst; and a method for producing a carbonyl compound through dehydrogenation of an alcohol in the presence of a catalyst including a hydrotalcite and, immobilized on a surface thereof, particles of a metal, in which dehydrogenation is performed in the absence of oxygen.Type: ApplicationFiled: March 9, 2007Publication date: May 27, 2010Inventors: Kiyotomi Kaneda, Noritsugu Yamasaki
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Patent number: 7718827Abstract: The present invention relates to a process for preparing aldehydes or ketones using an alkali metal hypochlorite or an alkaline earth metal hypochlorite in the presence of a ruthenium catalysts.Type: GrantFiled: June 28, 2006Date of Patent: May 18, 2010Assignee: Saltigo GmbHInventors: Wolfgang Mägerlein, Angela Köckritz, Andrea Dittmar, Michael Sebek
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Patent number: 7714173Abstract: The present invention relates to a method for preparing high-purity terephthalaldehyde which comprises re-crystallizing terephthalaldehyde crystals containing impurities, using an anti-solvent. Specifically, the present invention relates to a method for preparing terephthalaldehyde which comprises dissolving low-purity terephthalaldehyde prepared by a conventional method in dimethylsulfoxide and then re-crystallizing the solution, using water as an anti-solvent. The present invention is not only environment-friendly because it uses water only as an anti-solvent, but also economical because it may simply prepare high-purity terephthalaldehyde in a short time.Type: GrantFiled: June 14, 2007Date of Patent: May 11, 2010Assignee: LG Chem, Ltd.Inventors: Seong-Hoon Kang, In-Kyu Park, Jong-Suh Park, Young-Dae Kim, Jong-Hyun Chae
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Patent number: 7619123Abstract: The present invention provides novel methods for stabilizing lithiated halogen-substituted aromatic compounds. In particular, the method is useful for the preparation of 2-methoxy-5,6-difluorobenzaldehyde, an important intermediate for the preparation of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5-yl](2,3-difluoro-6methoxyphenyl)methanone, a potent and selective inhibitor of CDK4/Cyclin D1, CDK2/Cyclin E and CDK1/Cyclin B. The method is also useful for stabilizing other lithiated halogen-substituted aromatic compounds and is particularly useful for scale up reactions where the exothermic nature of the reaction can lead to reaction runway.Type: GrantFiled: October 24, 2008Date of Patent: November 17, 2009Assignee: Hoffmann-La Roche Inc.Inventors: Yaohui Ji, Thimma Rawalpally
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Publication number: 20090131660Abstract: 3-[4-(1,1-Dimethyl-propyl)-phenyl]-2-methyl-propionaldehyde and cis-4-{3-[4-(1,1-dimethyl-propyl)-phenyl]-2-methyl-propyl}-2,6-dimethyl-morpholine (Amorolfine) are synthesized, first by Heck reacting a compound of general formula (VI): with 2-methyl-prop-2-en-1-ol of formula (VII): in the presence of a palladium catalyst and a base, in a solvent selected from among N,N-dimethylformamide, polar protic and non-polar organic solvents, and at a temperature ranging from 60° C. to 150° C., and then conducting an amino reduction by reacting the 3-[4-(1,1-dimethyl-propyl)-phenyl]-2-methyl-propionaldehyde of formula (II) with cis-2,6-dimethyl morpholine of formula (IV): in the presence of a reducing agent and in a solvent.Type: ApplicationFiled: October 3, 2008Publication date: May 21, 2009Applicant: GALDERMA S.A.Inventors: JEAN-GUY BOITEAU, BRANISLAV MUSICKI
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Patent number: 7479575Abstract: The present invention is related to a new synthesis for preparing para-phenyl alkynyl benzaldehyde of general formula (I). The compounds of formula (I) are useful building blocks, in particular in the synthesis of electrically conducting polymers. R is selected from the group consisting of C1-C12-alkyl, C1-C12-alkyl aryl, C1-C12-alkyl heteroaryl, C2-C12-alkenyl, C2C12-alkenyl aryl, C2-C12-alkenyl heteroaryl, C2-C12-alkynyl, C2-C12-alkynyl aryl, C2-C12-alkynyl heteroaryl, C3-C8-cycloalkylC1-C12-alkyl-C3-C8-cycloalkyl, C1-C12-alkoxy, aryl, heteroaryl, halides.Type: GrantFiled: October 12, 2004Date of Patent: January 20, 2009Assignee: Laboratoires Serono SAInventors: Dominique Swinnen, Danig Pohin
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Patent number: 7411099Abstract: The present invention provides a liquid phase oxidation of toluene by using catalyst containing manganese (Manganese II acetate) in presence of Lewis acid (Stannous (II) chloride) and a bromide promoter (NaBr), at a temperature of 120° C. and at a pressure of air in the range of 70-400 psig, in presence of carboxylic acid (acetic acid), as a solvent, to obtain high selectivity to benzaldehyde (76%). High activity was obtained with minimum byproducts such as benzoic acid, benzyl alcohol and benzyl acetate.Type: GrantFiled: September 20, 2006Date of Patent: August 12, 2008Assignee: Council of Scientific & Industrial ResearchInventors: Raghunath Vitthal Chaudhari, Kalpendra Baburao Rajurkar, Sunil Sopana Tonde, Vilas Hari Rane
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Patent number: 7402709Abstract: A new high-yield, easily industrialized process for synthesizing compounds of formula (IV), in which X1 and X2, the same or different, are linear or branched C1-C8 alkyls, n and m are 0, 1 or 2, with the proviso that n and m are not simultaneously 0; or (OX1)n and (OX2)m taken together form an O-T-O group where T is chosen from —CH2—, —CH2CH2, —CH2CH2CH2—, —C(CH3)2—. The process comprises treating a chloromethyl derivative (I) with an alkaline acetate to form the intermediate acetylderivative (II); the intermediate (II) is to hydrolysed to form the alcohol (III); the alcohol (III) is then oxidised in the presence of air and catalysts to obtain the desired derivative (IV). The process runs its course within a short period of time, with high yields and high selectivity; in addition, the process does not require purification and separation of the intermediates and can therefore be favourably conducted in a single batch.Type: GrantFiled: October 28, 2004Date of Patent: July 22, 2008Assignee: Endura S.p.A.Inventors: Valerio Borzatta, Elisa Capparella, Carlotta Gobbi, Elisa Poluzzi
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Publication number: 20080108849Abstract: The present invention is related to a new synthesis for preparing para-phenyl alkynyl benzaldehyde of general formula (I). The compounds of formula (1) are useful building blocks, in particular in the synthesis of electrically conducting polymers. R is selected from the group consisting of C1-C12-alkyl, C1-C12-alkyl aryl, C1-C12-alkyl heteroaryl, C2-C12-alkenyl, C2C12-alkenyl aryl, C2-C12-alkenyl heteroaryl, C2-C12-alkynyl, C2-C12-alkynyl aryl, C2-C12-alkynyl heteroaryl, C3-C8-cycloalkylC1-C12--alkyl-C3-C8-cycloalkyl, C1-C12-alkoxy, aryl, heteroaryl, halides.Type: ApplicationFiled: October 12, 2004Publication date: May 8, 2008Applicant: APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.Inventors: Dominique Swinnen, Danig Pohin
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Patent number: 7342138Abstract: A process for producing an aromatic aldehyde compound represented by a general formula (3): (wherein R? and n are as defined below), which comprises reacting a benzyl compound represented by a general formula (1): (wherein R may represents hydrogen atom, n represents an integer of 1 to 6, and R? may be the same or different and represent a hydrogen atom or an alkyl gorup, an alkyl group or a phenyl group which may have a substituent) with an oxy-compound of bromine represented by the formula (2): MBrOm??(2) (wherein M represents a hydrogen atom or a metal atom, and m represents an integer of 1 to 3) in the presence of an acid catalyst. According to this method, an aromatic aldehyde compound can be produced in high selectivity by a simple operation without using an expensive catalyst or transition metal.Type: GrantFiled: August 27, 2003Date of Patent: March 11, 2008Assignee: Ihara Chemical Industry Co., Ltd.Inventor: Kentaro Kawazoe
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Patent number: 7241925Abstract: In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.Type: GrantFiled: December 15, 2004Date of Patent: July 10, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kinji Kato, Junya Nishiuchi, Mitsuharu Kitamura
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Patent number: 7189882Abstract: The present invention provides an improved process for the liquid phase oxidation of toluene to benzaldehyde with high selectivity and good activity in an organic acid medium using a catalyst system consisting of transition metal/metals and bromide as a promoter in the presence of lean oxygen.Type: GrantFiled: December 23, 2005Date of Patent: March 13, 2007Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vittal Chaudhari, Vilas Hari Rane, Amit Arwind Deshmukh, Sunil Sadashiv Divekar
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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: 7087789Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“?CF2?”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.Type: GrantFiled: January 12, 2004Date of Patent: August 8, 2006Assignee: University of Southern CaliforniaInventors: G. K. Surya Prakash, Jinbo Hu, George A. Olah
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Patent number: 7078572Abstract: The invention is a process for the preparation of compounds of the Formula I: where R1, R2, R3, R4 and R5 are defined in the specification, which are intermediates useful for the preparation of tubulin inhibitors which are useful in the treatment of cancer.Type: GrantFiled: August 11, 2005Date of Patent: July 18, 2006Assignee: Wyeth Holdings CorporationInventor: John Thomas Kendall
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Patent number: 6933405Abstract: The present invention is a user- and eco-friendly hypervalent iodine reagent (mIBX) capable of selectively oxidizing allylic and benzylic alcohols in water and other eco-friendly solvents and having generally the following structure: Allylic and benzylic alcohols are cleanly oxidized to the corresponding carbonyl compounds in water or water-THF mixtures, or other mixtures, using a water-soluble o-iodoxybenzoic acid derivative of the present invention.Type: GrantFiled: July 31, 2003Date of Patent: August 23, 2005Assignee: Board of Trustees of Western Illinois UniversityInventors: Thottumkara K. Vinod, Arun P. Thottumkara
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Patent number: 6891069Abstract: Disclosed herein are methods of synthesizing a 4-substituted-benzene-1,2-carbaldehyde. In one aspect, a method may include reacting a 4-substituted-1,2-bis(dibromomethyl) benzene with sulfuric acid to form a reaction product, introducing a solid sodium bicarbonate into the reaction product, and hydrolyzing the reaction product to form a 4-substituted-benzene-1,2-carbaldehyde, after introducing the bicarbonate.Type: GrantFiled: January 30, 2004Date of Patent: May 10, 2005Assignee: Ethicon, Inc.Inventors: Peter C. Zhu, Der-Haw Wang
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Patent number: 6881866Abstract: In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromatic compound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst. By limiting the amount of hydrogen fluoride to a specific range, the formylation rapidly proceeds under mild conditions without causing the precipitation of solid matters even when the starting polyalkyl-substituted aromatic compound has alkyl groups on both the carbon atoms adjacent to the site to be formylated.Type: GrantFiled: July 9, 2003Date of Patent: April 19, 2005Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kinji Kato, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
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Publication number: 20040230079Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“−CF2−”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.Type: ApplicationFiled: January 12, 2004Publication date: November 18, 2004Inventors: G.K.Surya Prakash, Jinbo Hu, George A. Olah
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Patent number: 6811832Abstract: Compounds of the formula (I): in which X1=H or F, X2=H or F, and Y=Cl, Br or I, are prepared by reacting, in a solvent or solvent mixture at a temperature below −60° C., a halobenzene of the formula (II) with an organic lithium compound and then with a formyl equivalent of the formula (III): and may be used as starting materials for preparing agrochemicals, electronic materials and pharmaceuticals.Type: GrantFiled: May 10, 2001Date of Patent: November 2, 2004Assignee: Clariant GmbHInventors: Rainer Wingen, Wolfgang Schmidt
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Patent number: 6677479Abstract: Compounds of the formula (I) and also process for preparing them where substituents X1, X2, Y and Z are defined as follows: X1 is H or F X2 is H or F Y is CI, Br, or I Z is CHO or COOH or CN n is 0 or 1 and also their use as starting material for preparing agrochemicals, electronics materials and pharmaceuticals.Type: GrantFiled: November 12, 2002Date of Patent: January 13, 2004Assignee: Clariant Finance LBVI LimitedInventors: Wolfgang Schmidt, Rainer Wingen
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Patent number: 6624331Abstract: A process for producing benzyloxyacetaldehyde which comprises oxidizing 2-benzyloxyethanol with hypochlorous acid in the presence of a nitroxy radical having the general formula (I) wherein R represents a hydrogen atom, an acyloxy group, an alkoxyl group or an aralkyloxy group.Type: GrantFiled: September 27, 2001Date of Patent: September 23, 2003Assignee: Kuraray Co., Ltd.Inventors: Masahiro Torihara, Kensuke Nagashima, Koichi Kanehira, Yoshin Tamai
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Patent number: 6624336Abstract: 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: GrantFiled: November 5, 2001Date of Patent: September 23, 2003Assignee: Showa Denko K.K.Inventors: Toru Sasaki, Tetsuhiro Furukawa, Toru Yoshida, Yutaka Ohnishi, Hiroyuki Monzen, Hideo Miyata, Kohei Morikawa
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Patent number: 6608229Abstract: 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: GrantFiled: April 25, 2001Date of Patent: August 19, 2003Assignee: SCA Hygiene Products Zeist B.V.Inventors: Petter Bragd, Arie Cornelis Besemer, Jeffrey Wilson Thornton
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Patent number: 6596906Abstract: The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.Type: GrantFiled: September 21, 2001Date of Patent: July 22, 2003Assignee: Bayer AktiengesellschaftInventors: Käthe Baumann, Albrecht Marhold
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Publication number: 20030125583Abstract: The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.Type: ApplicationFiled: January 30, 2003Publication date: July 3, 2003Inventors: Kathe Baumann, Albrecht Marhold
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Patent number: 6518419Abstract: 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: GrantFiled: November 7, 2000Date of Patent: February 11, 2003Assignee: Nederlandse Organisatie voor Toegepast-Natuurwetenschappelijk Onderzoek TNOInventors: Jan Pieter Van Der Lugt, Jan Matthijs Jetten, Arie Cornelis Besemer, Hendrik Arend Van Doren
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Patent number: 6476279Abstract: Disclosed are methods of producing fluorinated alcohols which find particular use in the syntheses of pharmaceutical drugs. The methods comprise generally, the steps of (a) reacting a halogenated alkane with an alkyl vinyl ether to form an unsaturated halogenated aldehyde; (b) reducing the unsaturated halogenated aldehyde to form an unsaturated halogenated alcohol; and (c) reducing the unsaturated halogenated alcohol to form a fluorinated alcohol.Type: GrantFiled: January 12, 2001Date of Patent: November 5, 2002Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Andrew Joseph Poss