Halogen Containing Patents (Class 568/495)
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Patent number: 8865947Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).Type: GrantFiled: December 6, 2012Date of Patent: October 21, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, Sheng Peng
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Publication number: 20140309452Abstract: Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ?-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).Type: ApplicationFiled: April 9, 2014Publication date: October 16, 2014Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Miyoshi Yamashita, Takehiko Fukumoto, Takeshi Kinsho
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Publication number: 20120288445Abstract: Compounds of the formula (I) are disclosed: 18F—(CHR)n(CH2)mCHO??(I) in which n and m are independently 0 and 1 with at least one of n and m being 1, and R (if present) is a hydrogen atom or a methyl group, subject to the proviso that if n is 1 and R is methyl then m is 0. Synthesis of the compounds is described together with their use in radiolabelling reactions, e.g. for the radiolabelling of peptides to facilitate detection by Positron Emission Tomography (PET) imaging. The preferred compound is [18F]Fluoroacetaldehyde.Type: ApplicationFiled: April 13, 2012Publication date: November 15, 2012Applicant: The University of ManchesterInventor: Christian PRENANT
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Publication number: 20120207858Abstract: Provided are biocide compositions and bleach compositions comprising organic acyl polyoxychlorine and related methods. The reduction of the acyl polyoxychlorine group releases a reactive intermediate that undergoes a series of cascading reduction steps, resulting in termination products Generally Recognized As Safe.Type: ApplicationFiled: January 11, 2012Publication date: August 16, 2012Applicant: TRUOX, INC.Inventor: Roy W. Martin
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Publication number: 20100068139Abstract: The invention relates to conjugates of formula (V) or (VI): wherein X is —CO—NH—, —NH—, —O—, —NHCONH—, or —NHCSNH—; their use as radiopharmaceuticals, processes for their preparation, and synthetic intermediates used in such processes.Type: ApplicationFiled: March 12, 2004Publication date: March 18, 2010Inventors: Alan Cuthbertson, Magne Solbakken, Joseph Maduabuchi Arukwe, Hege Karlsen, Matthias Eberhard Glaser
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Publication number: 20090302262Abstract: Claimed are fluorous telomeric compounds of the formula: RF-A-[CH2]cCR2R3-Z where RF is a perfluoroalkyl radical of 1 to 20 carbon atoms, A is a group of the formulae R1 is CF3 OR4, Cl, Br or I, R2 and R3 are H, alkyl or aryl R4 is perfluoromethyl, perfluoropropyl or perfluoropropyloxypropyl X and Y are H, Cl or F Z is —OH, —OCOCH?CH2 or —OCOCCH3?CH2 a is from 0 to 10, b is from 1 to 30 and c is from 1 to 30. These compounds are copolymerized with further monomers. The copolymers thus obtained are useful for water-, oil- and soil-repellent finishing of fibrous substrates.Type: ApplicationFiled: December 22, 2006Publication date: December 10, 2009Applicant: CLARIANT INTERNATIONAL LTDInventors: Hans Götz, Wolfgang Knaup, Anton Probst, Christian Ahollinger
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Publication number: 20080274046Abstract: Compounds of the formula (I) are disclosed: 18F—(CHR)n(CH2)mCHO ??(I) in which n and m are independently 0 and 1 with at least one of n and m being 1, and R (if present) is a hydrogen atom or a methyl group, subject to the proviso that if n is 1 and R is methyl then m is 0. Synthesis of the compounds is described together with their use in radiolabelling reactions, e.g. for the radiolabelling of peptides to facilitate detection by Positron Emission Tomography (PET) imaging. The preferred compound is [18F]Fluoroacetaldehyde.Type: ApplicationFiled: February 20, 2008Publication date: November 6, 2008Inventor: Christian Prenant
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Patent number: 5583208Abstract: A ganglioside GM3 derivative containing fluorine atoms in a ceramide portion thereof, represented by the formula: ##STR1## in which m is an integer of at least 2, n is an integer of 0 to 7 provided that m is larger than n, and R represents an alkyl group or a fluoroalkyl group is disclosed.Type: GrantFiled: May 8, 1995Date of Patent: December 10, 1996Assignee: Daikin Industries, Ltd.Inventors: Takao Iida, Yutaka Ohira
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Patent number: 5563235Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.Type: GrantFiled: January 16, 1996Date of Patent: October 8, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5550298Abstract: The catalytic process obtains a methyl tertiary butyl ether by feeding methanol over a solid catalyst section in a rectifying column having vertical layers in which a catalyst material is enclosed. At least one of the enclosing walls is impermeable to the catalyst material while being permeable to the methanol. A reactant comprising a mixture of saturated and unsaturated 4 carbon-chain hydrocarbons is fed into the solid catalyst section with methanol to produce a methyl tertiary butyl ether.Type: GrantFiled: March 29, 1995Date of Patent: August 27, 1996Assignee: Sulzer Brothers LimitedInventors: Ronald Shelden, Jean-Paul Stringaro
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Patent number: 5512652Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.Type: GrantFiled: February 14, 1995Date of Patent: April 30, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5498802Abstract: A process for preparing 6-chloro-2-hexanone which comprises the steps of (a) dehydrating cyclohexanol in the presence of a suitable catalyst and at a suitable temperature and for a sufficient period of time to form cyclohexene; (b) rearranging said cyclohexene at a higher temperature than in step (a) in the presence of a suitable catalyst and for a sufficient period of time to form 1-methylcyclopentene; (c) hydrating said 1-methylcyclopentene at a temperature lower than step (b) and in the presence of a resin catalyst for a sufficient period of time to form 1-methylcyclopentanol; (d) reacting said 1-methylcylcopentanol with a suitable amount of an alkali metal hypochlorite in the presence of a carboxylic acid to form 1-methylcyclopentyl hypochlorite; and (e) heating said 1-methylcyclopentyl hypochlorite for a sufficient period of time to form 6-chloro-2-hexanone.Type: GrantFiled: February 28, 1995Date of Patent: March 12, 1996Assignee: Hoechst Celanese CorporationInventors: Diane E. Allen, Ramakrishnan Chidambaram
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Patent number: 5414139Abstract: A process for manufacturing monochloroacetaldehyde trimer and chloral together by effectively utilizing a raw material acetaldehyde or para-aldehyde. The process comprises a step of chlorinating acetaldehyde or para-aldehyde to produce a chlorinated liquid of which the major component is monochloroacetaldehyde, a step comprising adding chloral to said chlorinated liquid and distilling the mixture to obtain a fraction of which the major components are monochloroacetaldehyde and chloral, a step of trimerizing monochloroacetaldehyde by reacting said fraction in the presence of a trimerization catalyst and separating the MCA trimer by filtration, and a step of chlorinating other fractions from said distillation step and the filtrate from said trimerization step to produce chloral. According to this process all raw material aldehydes and components derived from aldehydes which have not been consumed for the production of MCA trimer can be easily converted into chloral which is useful as an industrial chemical.Type: GrantFiled: March 15, 1994Date of Patent: May 9, 1995Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
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Patent number: 5414140Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.Type: GrantFiled: January 21, 1992Date of Patent: May 9, 1995Assignee: E. I. du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5405870Abstract: Compounds of formula (Ic): ##STR1## having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.Type: GrantFiled: November 4, 1993Date of Patent: April 11, 1995Assignee: Sankyo Company, LimitedInventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
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Patent number: 5386063Abstract: (all-E)-2,7,-dimethylocta-2,4,6-triene-1,8-dial-.sup.13 C.sub.4 is synthesized from commercially available and relatively inexpensive starting compounds, and the key starting compound is triethyl phosphonoacetate-.sup.13 C.sub.2. The .sup.13 C labeled dial is useful as an intermediate in synthesizing .sup.13 C labeled carotenoids.Type: GrantFiled: June 16, 1993Date of Patent: January 31, 1995Assignees: The Catholic University of America, The United States of America as represented by the Secretary of AgricultureInventors: Frederick Khachik, Gary R. Beecher, Betty W. Li
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Patent number: 5304661Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##Type: GrantFiled: April 9, 1993Date of Patent: April 19, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5292911Abstract: Novel monocyclic terpene derivative of the formula: ##STR1## wherein R is hydrogen atom, trimethylsilyl group or 1-ethoxyethyl group, and novel intermediates therefor. The terpene derivative (I) is a useful intermediate for preparing Sarcophytol A having an anti-carcinogenesis promoter activity and an antitumor activity.Type: GrantFiled: March 10, 1992Date of Patent: March 8, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5248832Abstract: A process for the manufacture of trifluoroacetaldehyde, or a hydrate or hemiacetal thereof, which comprises reduction of an ester of trifluoroacetic acid with a borohydride reducing agent in a hydroxylic solvent to form trifluoroacetaldehyde hydrate or hemiacetal; whereafter if the free aldehyde is required, water or alcohol is removed from the hydrate or hemiacetal respectively using conventional procedures.Type: GrantFiled: May 20, 1992Date of Patent: September 28, 1993Assignee: Imperial Chemical Industries PLCInventor: Stanley A. Lee
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Patent number: 5166373Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.Type: GrantFiled: December 30, 1991Date of Patent: November 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5077439Abstract: Compounds of formula I ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl or benzyl, are prepared by reacting a butanal of formula II ##STR2## wherein X and Y are each independently of the other chloro, bromo or iodo, in an inert solvent, with a compound of formula IIIR-S-Me (III)wherein R is as defined above and Me is an alkali metal cation, and converting the resultant compound of formula IV ##STR3## wherein X and R are as defined above, in an inert solvent and in the presence of a base, into a compound of formula I.Type: GrantFiled: March 11, 1991Date of Patent: December 31, 1991Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 5068390Abstract: 1,1,1-trifluoro-2-propene compounds which are useful in the preparation of insecticidal, acaricidal and nematicidal arylpyrrole compounds are described. A method for the preparation of 1,1,1-trifluoro-2-propene compounds is presented.Type: GrantFiled: July 31, 1990Date of Patent: November 26, 1991Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Kenneth A. M. Kremer
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Patent number: 5017718Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.Type: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 5015780Abstract: Dihalobutyraldehydes of formula I ##STR1## wherein X and Y are each independently of the other Cl or Br, are obtainable at high rates of conversion and with excellent selectivities by catalytic dehalogenation with hydrogen by carrying out the reaction with appropriate .alpha.,.alpha.-dihalobutyraldehydes in an organic aprotic solvent. The dihalobutyraldehydes are intermediates for the synthesis of herbicidal acyl cyclohexanediones.Type: GrantFiled: January 16, 1990Date of Patent: May 14, 1991Assignee: Ciba-Geigy CorporationInventors: Heinz Steiner, Hans Tobler
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Patent number: 5008462Abstract: A method for preparing a monochloroacetaldehyde trimer in a high yield is here disclosed which comprises the steps of dissolving, in an organic solvent, a solution containing monochloroacetaldehyde as the main component, and then trimerizing monochloroacetaldehyde in the presence of sulfuric acid. The thus prepared monochloroacetaldehyde trimer can be heated at 120.degree. C. under atmospheric pressure to obtain pure monochloroacetaldehyde.Type: GrantFiled: November 8, 1989Date of Patent: April 16, 1991Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Makoto Ishizuka, Takashi Wakasugi
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Patent number: 4983776Abstract: The invention relates to the synthesis of functional fluoro derivatives and more particularly that of perfluorinated aldehydes of the type R.sub.F -CHO where R.sub.F denotes a linear or branched perfluoroalkyl radical.A perfluoroalkyl iodide R.sub.F I is reacted over the zinc-copper metal couple, in the presence of a radical initiator, with an amide RCONR.sub.1 R.sub.2, R denoting a hydrogen atom or a methyl or ethyl radical, and each of R.sub.1 and R.sub.2 denoting a C.sub.1 -C.sub.4 alkyl radical.Type: GrantFiled: April 27, 1989Date of Patent: January 8, 1991Assignee: Societe AtochemInventors: Sylvie Benefice-Malouet, Hubert Blancou, Auguste Commeyras
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Patent number: 4983775Abstract: Novel physiologically active substances Ks-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.Type: GrantFiled: January 16, 1990Date of Patent: January 8, 1991Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
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Patent number: 4876370Abstract: 1,3,5-Nonatriene derivatives of formula: ##STR1## in which R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, form a carbonyl group, or each of R.sub.1 and R.sub.2 denotes alkoxy or R.sub.1 and R.sub.2 together form an alkylenedioxy radical, which may be made by reaction of a butadiene derivative of formula: ##STR2## in which R is alkyl or phenyl, with a butanal ketoacetal of 10 formula: ##STR3## followed by reaction of the product with a halomethyltriphenylphosphonium halide, are useful intermediates e.g. for the production of phytol.Type: GrantFiled: September 19, 1988Date of Patent: October 24, 1989Assignee: Rhone-Poulenc SanteInventors: Lucette Duhamel, Pierre Duhamel
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Patent number: 4806280Abstract: Compounds of formula ##STR1## in which n denotes an integer from 1 to 10 and X and Y, which are identical or different, each denote an electron-attracting group, are made by reacting a halogenating agent with a compound of formula ##STR2## in which R, X and Y are as hereinbefore defined, anionized by a base.Type: GrantFiled: August 3, 1987Date of Patent: February 21, 1989Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4733012Abstract: A process for the preparation of 4-chloromethylbenzaldehyde, 4-bromomethylbenzaldehyde and 4-iodomethylbenzaldehyde is disclosed. The desired 4-halomethylbenzaldehyde is prepared by reacting 4-hydroxymethylbenzaldehyde with the appropriate gaseous hydrogen halide and/or with the appropriate aqueous hydrohalic acid. The 4-halomethylbenzaldehydes produced by the disclosed process are useful as raw materials for pharmaceuticals and serve as starting materials for the preparation of conductive organic compounds.Type: GrantFiled: March 17, 1987Date of Patent: March 22, 1988Assignee: Wacker-Chemie GmbHInventors: Hermann Braunling, Dieter Kippe
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Patent number: 4691062Abstract: 4-chloro-butanals of the formula ##STR1## where R is hydrogen or a straight or branched chain alkyl group of 1 to 4 carbon atoms are produced by reacting the corresponding 1,1-dimethoxy-4-hydroxybutane at a temperature between -20.degree. and +80.degree. C. in the presence of triphenylphosphine with carbon tetrachloride and hydrolyzing the 1,1-dimethoxy-4-chloro-butane obtained in acid medium.Type: GrantFiled: October 22, 1986Date of Patent: September 1, 1987Assignee: Degussa AktiengesellschaftInventors: Juan Andrade, Gunter Prescher, Klaus Kohler
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Patent number: 4628122Abstract: Chloral is removed from aqueous hydrochloric acid containing chloral in a stripping zone at superatmospheric pressure and concentrated in a rectifying zone at superatmospheric pressure. The method is particularly suited for the treatment of feed compositions originating from the oxychlorination of ethylene.Type: GrantFiled: November 1, 1985Date of Patent: December 9, 1986Assignee: PPG Industries, Inc.Inventors: Frederick J. Kuntz, Henry W. Schussler
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Patent number: 4577028Abstract: Novel 5-haloalkyl-pyridines suitable for producing pesticidal compositions, particularly insecticides, and corresponding to the formula ##STR1## wherein R is a C.sub.2 -C.sub.10 -alkyl group which is uniformly or nonuniformly substituted by 1 to 21 halogen atoms, and X is halogen;processes for producing them, as well as to the novel starting products and intermediates used or intermediately produced or formed in the production processes.Type: GrantFiled: October 14, 1982Date of Patent: March 18, 1986Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Eginhard Steiner
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Patent number: 4469896Abstract: Chloropyridines of the formula ##STR1## wherein either R is chlorine and R' is methyl or trifluoromethyl, or R is methyl, trichloromethyl or trifluoromethyl and R' is chlorine, or R and R' are methyl, can be obtained by a novel, simple process by the addition of trichloroacetaldehyde to methacrylonitrile or .alpha.-trifluoromethacrylonitrile, 2,2-dichloropropionaldehyde, pentachloropropionaldehyde or 2,2-dichloro-3,3,3-trifluoropropionaldehyde to acrylonitrile, or 2,2-dichloropropionaldehyde to methacrylonitrile, in the presence of a catalyst, in particular copper powder or copper(I) chloride, and cyclizing the open-chain intermediate obtained.The chloropyridines of the formula (I) are known per se and are suitable for the production of different compounds, in particular of insecticides and herbicides.Type: GrantFiled: July 8, 1983Date of Patent: September 4, 1984Assignee: Ciba-Geigy CorporationInventors: Eginhard Steiner, Pierre Martin
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Patent number: 4375563Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.Type: GrantFiled: March 30, 1982Date of Patent: March 1, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4315764Abstract: 1-Allyl-triazole derivatives of the formula ##STR1## in which R represents hydrogen, alkyl or optionally substituted aralkyl,R.sup.1 represents optionally substituted alkyl, cycloalkyl or optionally substituted aryl,R.sup.2 represents alkyl andR.sup.3 represents alkyl, cycloalkyl, optionally substituted cycloalkenyl, alkenyl or optionally substituted aryl, orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkenyl or cycloalkylX represent the group ##STR2## or the keto group, R.sup.4 represents hydrogen, alkyl, optionally substituted aralkyl, acyl or optionally substituted carbamoyl andR.sup.5 represents hydrogen, alkyl or optionally substituted aralkyl,or acid addition salts or metal salt complexes thereof are characterized by fungicidal and plant growth regulatory activity.Type: GrantFiled: February 4, 1980Date of Patent: February 16, 1982Assignee: Bayer AktiengesellschaftInventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
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Patent number: 4311563Abstract: The invention relates to a process for the isolation of chloroacetaldehyde which is obtained as a by-product during the synthesis of acetaldehyde from ethylene and air in an aqueous palladium/cupric chloride solution by the 2-stage process. The mixture to be worked-up to chloroacetaldehyde is taken from the acetaldehyde distillation column and transferred to a distillation and extraction system, where it is fractionally condensed. The chloroacetaldehyde-containing fraction is extracted with water and the aqueous extract is subjected to purification distillation.Type: GrantFiled: March 31, 1981Date of Patent: January 19, 1982Assignee: Wacker-Chemie GmbHInventors: Werner Opavsky, Josef Reisner, Alois Maier
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Patent number: 4305876Abstract: A process for asymmetrically hydrogenating through the use of microorganisms a double bond connected to tertiary carbon atom in an olefinic aliphatic compound to produce a tertiary, optically active aliphatic compound useful as an intermediate for optically active Vitamins E and K.Type: GrantFiled: November 24, 1978Date of Patent: December 15, 1981Assignee: Hoffmann-La Roche, Inc.Inventors: Richard Barner, Walter Boguth, Hans G. W. Leuenberger, Max Schmid, Reinhard Zell
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Patent number: 4288635Abstract: A method for the preparation of (E)-4-bromo-2-methylbut-2-en-1-al comprises brominating 3,4-epoxy-3-methyl-1-butene with cupric bromide in the presence of lithium carbonate.Type: GrantFiled: May 23, 1980Date of Patent: September 8, 1981Assignee: J. T. Baker Chemical Co.Inventor: Gary M. Gray
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Patent number: 4283536Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties.A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII).Type: GrantFiled: April 30, 1979Date of Patent: August 11, 1981Assignee: University of VermontInventor: Martin E. Kuehne
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Patent number: 4267330Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties.A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.Type: GrantFiled: August 24, 1978Date of Patent: May 12, 1981Assignee: Omnium Chimique Societe AnonymeInventor: Martin E. Kuehne
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Patent number: 4263269Abstract: Method of removing organic contaminants from aqueous hydrochloric acid comprising countercurrently contacting the aqueous acid containing the contaminants and steam at superatmospheric pressures, and recovering said aqueous acid substantially free from organic contaminants. The invention is particularly adapted for the removal of chloral from aqueous hydrochloric acid.Type: GrantFiled: May 5, 1980Date of Patent: April 21, 1981Assignee: The Dow Chemical CompanyInventors: John C. Little, Charles R. Youngson, Jr.
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Patent number: 4220774Abstract: The preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.Type: GrantFiled: October 26, 1978Date of Patent: September 2, 1980Assignee: Omnium ChimiqueInventor: Martin E. Kuehne
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Patent number: 4215044Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.Type: GrantFiled: April 23, 1979Date of Patent: July 29, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton