Acyclic Carbon To Carbon Unsaturation Containing Patents (Class 570/189)
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Patent number: 12116328Abstract: The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M2 represents Li or MgZ2, wherein Z2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X3 and X4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7).Type: GrantFiled: July 7, 2020Date of Patent: October 15, 2024Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yuki Miyake, Takeshi Kinsho, Ryo Komatsu
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Patent number: 11358918Abstract: The present invention provides methods for the preparation of halogenated alkenes from halogenated alkanes using a homogeneous catalyst.Type: GrantFiled: April 2, 2019Date of Patent: June 14, 2022Assignee: Blue Cube IP LLCInventors: Max Tirtowidjojo, Manfred Kokott, Marc Sell, John D. Myers, Anja Peters
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Publication number: 20140323744Abstract: The specification relates to compounds and process for the preparation of a compound of formula 7, where LG is a leaving group and hal is a halide and is Cl, Br or I. The compound of formula 7 can be useful in the preparation of natural products, such as halichondrin and its derivatives.Type: ApplicationFiled: November 29, 2012Publication date: October 30, 2014Inventors: Fabio E.S. Souza, Huzaifa Rangwala, Boris Gorin, Ming Pan
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Publication number: 20140316170Abstract: The present invention relates, in part, to the discovery that the presence of impurities in 1,1,2,3-tetrachloropropene (1230xa) results in catalyst instability during the fluorination of 1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the impurities, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf).Type: ApplicationFiled: October 11, 2012Publication date: October 23, 2014Inventors: Selma BEKTESEVIC, Daniel C. MERKEL, Mario Joseph NAPPA, Xuehui SUN, Hsueh Sung TUNG, Haiyou WANG
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Publication number: 20140275656Abstract: Provided are (Z,Z,E)-1-chloro-6,10,12-pentadecatriene that can be synthesized without an oxidation reaction and a method for preparing (Z,Z,E)-7,11,13-hexadecatienal by using (Z,Z,E)-1-chloro-6,10,12-pentadecatriene while not using an oxidation reaction. More specifically, provided is a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal including a step of reacting a Grignard reagent into which (Z,Z,E)-1-chloro-6,10,12-pentadecatriene is converted with ethyl orthoformate to obtain (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene, and a step of treating the (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene with an acid to obtain (Z,Z,E)-7,11,13-hexadecatrienal.Type: ApplicationFiled: February 25, 2014Publication date: September 18, 2014Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Yuki Miyake, Miyoshi Yamashita, Takehiko Fukumoto, Naoki Ishibashi
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Publication number: 20140275572Abstract: The present invention relates to the synthesis of ent-progesterone and intermediates thereof.Type: ApplicationFiled: March 15, 2014Publication date: September 18, 2014Inventors: John W. Cran, Yinglin Han, Faliang Zhang
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Publication number: 20140275650Abstract: The present invention relates in part to a method of stabilizing chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).Type: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haluk KOPKALLI, Haiyou WANG, Hsueh SUNG TUNG, Daniel C. MERKEL
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Publication number: 20140256995Abstract: The present invention relates, in part, to the discovery that the presence of moisture in 1,1,2,3-tetrachloropropene (HCO-1230xa) results in catalyst deactivation and accelerated corrosion in the reactor during the fluorination of HCO-1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the moisture, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: ApplicationFiled: September 29, 2012Publication date: September 11, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Selma Bektesevic, Hsueh Tung
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Patent number: 8829255Abstract: Provided are (Z,Z,E)-1-chloro-6,10,12-pentadecatriene that can be synthesized without an oxidation reaction and a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal by using (Z,Z,E)-1-chloro-6,10,12-pentadecatriene while not using an oxidation reaction. More specifically, provided is a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal including a step of reacting a Grignard reagent into which (Z,Z,E)-1-chloro-6,10,12-pentadecatriene is converted with ethyl orthoformate to obtain (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene, and a step of treating the (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene with an acid to obtain (Z,Z,E)-7,11,13-hexadecatrienal.Type: GrantFiled: February 25, 2014Date of Patent: September 9, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yuki Miyake, Miyoshi Yamashita, Takehiko Fukumoto, Naoki Ishibashi
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Patent number: 8481793Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: July 26, 2012Date of Patent: July 9, 2013Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung, Konstantin A. Pokrovski
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Patent number: 8252965Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: August 12, 2009Date of Patent: August 28, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
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Patent number: 8247626Abstract: To provide a method for purifying tetrafluoroethylene by removing, from tetrafluoroethylene containing a polymerization inhibitor, the polymerization inhibitor by adsorption. A method of bringing tetrafluoroethylene containing a polymerization inhibitor into contact with a silica gel containing a metal salt in an amount of from 250 to 100,000 mass ppm as calculated as metal atoms to remove the polymerization inhibitor by adsorption, and the metal salt is preferably a salt of a metal of Group 3 to 13 of the Periodic Table, more preferably a salt of a metal of Group 8 to 10 of the Periodic Table. For example, as the metal salt, a salt of at least one metal selected from the group consisting of iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium and platinum may be used.Type: GrantFiled: October 21, 2010Date of Patent: August 21, 2012Assignee: Asahi Glass Company, LimitedInventors: Shigeru Aida, Manabu Sato, Takeya Sakamoto, Nobuo Matsushita, Yuuji Hayase, Tomohiro Gotou, Kenji Fujiwara
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Publication number: 20110313216Abstract: 2,3-dichlorobutadiene-1,3 of high purity is produced from 1,2,3,4-tetrachlorobutane by a process comprising the steps of dehydrochlorination, chlorination of the reaction product obtained in the dehydrochlorination step and subsequent separation of a 2,3-dichlorobutadiene-1,3 composition from the reaction product of the chlorination step.Type: ApplicationFiled: August 30, 2011Publication date: December 22, 2011Inventor: TERRY WAYNE REDWINE
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Publication number: 20110251443Abstract: The invention relates to a process for the manufacture of vinyl chloride monomer comprising the preparation of acetylene from one or more renewable starting materials and then the reaction of the acetylene with hydrogen chloride in order to form vinyl chloride monomer. The invention also relates to the vinyl chloride monomer obtained and to its use.Type: ApplicationFiled: November 30, 2009Publication date: October 13, 2011Inventor: Jean-Luc Dubois
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Patent number: 8030531Abstract: 2,3-dichlorobutadiene-1,3 of high purity is produced from 1,2,3,4-tetrachlorobutane by a process comprising the steps of dehydrochlorination, chlorination of the reaction product obtained in the dehydrochlorination step and subsequent separation of a 2,3-dichlorobutadiene-1,3 composition from the reaction product of the chlorination step.Type: GrantFiled: December 16, 2008Date of Patent: October 4, 2011Assignee: Dupont Performance Elastomers LLCInventor: Terry Wayne Redwine
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Patent number: 8026400Abstract: Purified chlorinated alkenes are produced by a process in which a mixture of i) a first chlorinated alkene that has at least one beta-chlorine substituent and no alpha-chlorine substituents and ii) a second chlorinated alkene that has at least one alpha-chlorine substituent is contacted with chlorine in an amount sufficient to further chlorinate the second chlorinated alkene, but which is insufficient to cause conversion of more than 20% of the first chlorinated alkene.Type: GrantFiled: December 16, 2008Date of Patent: September 27, 2011Assignee: Dupont Performance Elastomers LLCInventor: Terry Wayne Redwine
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Publication number: 20110196178Abstract: Compositions including chlorinated propenes and a phenolic antioxidant are described herein.Type: ApplicationFiled: April 9, 2008Publication date: August 11, 2011Inventor: Janice M. Nyberg
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Publication number: 20110004028Abstract: Disclosed are: an advantageous production process for a carotenoid intermediate; and others. Specifically disclosed are: a process for producing a dialcohol represented by formula (1), which is characterized by reacting a Grignard reagent with an acetylene gas in an organic solvent at a temperature of 30° C. or higher to prepare an ethynyl magnesium halide and subsequently reacting the ethynyl magnesium halide with methacrolein; a process for producing an allylhalide compound represented by formula (3) [wherein X represents a halogen atom: and the wavy line means the compound is either of E/Z geometric isomers or a mixture thereof], which is characterized by reducing a dialcohol represented by formula (1) with hydrogen to produce a triene alcohol represented by formula (2) [wherein the wavy line is as defined above] and halogenating the triene alcohol; and an allylchloride compound represented by formula (4) [wherein the wavy line is as defined above].Type: ApplicationFiled: March 2, 2009Publication date: January 6, 2011Inventor: Toshiya Takahashi
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Patent number: 7655722Abstract: The present invention relates to adhesive compositions having: a phosphate group-containing monomer (a) having a fluorocarbon group represented by Chemical Formula 1; and a solvent (b), where R is a hydrogen atom or a methyl group, n, p and q are natural numbers 2?n?10, p+q?n and p+q+n?13.Type: GrantFiled: April 13, 2006Date of Patent: February 2, 2010Assignee: Kuraray Medical Inc.Inventors: Kazumitsu Nakatsuka, Naoki Nishigaki, Mitsunobu Kawashima
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Publication number: 20090023963Abstract: Perchloroethylene is made by thermal noncatalytic pyrolysis of carbon tetrachloride in the presence of chlorine and methyl chloride, or methane, or natural gas. Vapor carbon tetrachloride is used both as a raw material and a diluent, and reaction takes place under conditions with high consumption of maximize conversion of carbon tetrachloride to perchloroethylene and minimum formation of heavies, especially, low formation of hexchlorobenzene, another environmental undesirable chemical compound.Type: ApplicationFiled: June 20, 2008Publication date: January 22, 2009Inventor: Nie-Jiann Wen
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Patent number: 7470827Abstract: Described are compositions adapted to catalyze the vapor phase dehydrohalogenation of 1,1,2-trihaloethane to 1,1-dihaloethylene, e.g., 1,1,2-trichloroethane to vinylidene chloride. These materials include activated carbon and at least one benzimidazole-containing material defined herein as including benzimidazole, a derivative thereof, a salt thereof or mixtures thereof. Also described are methods for producing and using these catalytic compositions.Type: GrantFiled: June 3, 2005Date of Patent: December 30, 2008Assignee: PPG Industries Ohio, Inc.Inventors: Yurii Oleksiyovych Serhuchev, Yurii Vasyliyovych Bilokopytov, Igorlvanovych Chernobaev
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Publication number: 20080177115Abstract: Isotopically labeled alpha-keto acids and esters are disclosed herein. Also disclosed are methods of synthesizing isotopically labeled alpha-keto acids and esters.Type: ApplicationFiled: July 11, 2007Publication date: July 24, 2008Applicant: Spectra Gases, Inc.Inventors: Rodolfo Antonio Martinez, Mark Minton, Frank Elbert Anderson, Erick Gabriel Ortiz, Kenneth Edmund Tortolani
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Patent number: 6660812Abstract: Disclosed is a system of making an olefin derivative from a dilute olefin feed. Dilute olefin is sent to an olefin reaction unit to form an olefin derivative product. The olefin derivative product is recovered from the reaction unit while a vent stream is also removed. Olefin is separated from the vent stream, and the olefin is sent to the olefin reaction unit for additional processing.Type: GrantFiled: June 15, 2001Date of Patent: December 9, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: Keith H. Kuechler, Minquan Cheng, Marc L. DeChellis, David R. Lumgair, Jr., Russell D. Sellen, Gary F. Janda
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Patent number: 6610219Abstract: Functional optical materials for optical systems that are typically useful in optical waveguides, optical switching systems, optical modulators, optical computing systems and the like. Included are polymer systems and electrooptical chromophores. Polymers are thermoplastic and/or thermosetting polymers and are blended or co-polymerized with the electrooptic chromophore. The thermoplastic or thermosetting polymer selected from an acrylic/methacrylic, polyester, polyurethane, polyimide, polyamide, epoxy resin, or hybrid (organic-inorganic) or nanocomposite polyester polymer. The electrooptic chromophore is selected from a substituted aniline, substituted azobenzene, substituted stilbene, or substituted imine. Methods for improving adhesion promotion for the various novel materials are also provided.Type: GrantFiled: February 6, 2001Date of Patent: August 26, 2003Assignee: Battelle Memorial InstituteInventors: Vincent D. McGinniss, Steven M. Risser
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Publication number: 20020107422Abstract: There are disclosed a composition comprisingType: ApplicationFiled: February 5, 2002Publication date: August 8, 2002Inventors: Noriyuki Doi, Shinzo Seko, Kazutaka Kimura, Toshiya Takahashi
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Patent number: 6406680Abstract: This invention describes a new type of X-ray contrast agents. It has been found that iodinated alkenes containing one or several C═C double bonds substituted with electronic neutral substituents and iodine can be used as X-ray contrast agents. Also new iodoalkene compounds are described.Type: GrantFiled: September 6, 2000Date of Patent: June 18, 2002Assignee: Nycomed Imaging ASInventor: Hanno Priebe
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Patent number: 6403789Abstract: A halogenating agent of the formula (1) and a method of halogenating hydroxyl group wherein R1 and R2 are the same or different and are each ethyl, propyl, isopropyl, butyl, isobutyl or allyl; X is chlorine atom or bromine atom; and Y is chlorine ion, bromine ion, dichlorophosphate ion, dibromophosphate ion, chlorosulfonate ion, bromosulfonate ion, chlorooxalate ion or bromooxalate ion.Type: GrantFiled: September 26, 2000Date of Patent: June 11, 2002Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Daisuke Suzuki, Ryo Kikuchi, Masaru Yasui
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Patent number: 6388151Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.Type: GrantFiled: November 24, 1998Date of Patent: May 14, 2002Assignee: Boulder Scientific CompanyInventors: Jeffrey M. Sullivan, Richard D. Crawford
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Publication number: 20020045784Abstract: In a process for production of allyl chloride whereby allyl alcohol and hydrogen chloride are reacted in the presence of a catalyst and the resulting allyl chloride is distilled off from the reaction system, the by-production of diallyl ether is suppressed by lowering the molar concentration ratio of hydrogen chloride with respect to allyl alcohol in the reaction solution ([AAL]½/[HCL]).Type: ApplicationFiled: February 15, 2001Publication date: April 18, 2002Inventors: Kenji Usui, Shoichi Oishi, Toshitaka Hiro, Tatsuharu Arai
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Patent number: 6271280Abstract: Intermediate compositions comprising ethynylorgano polyorganosiloxanes are prepared by hydrosilylation of an olefinic hydroxy compound followed by reaction with a propargyl halide, or by hydrosilylation of a diethynyl compound. The intermediate compositions may be oxidatively coupled to form poly(conjugated diacetylenic)polyorganosiloxanes. The latter may be cured thermally or by radiation to form cured compositions useful as release coatings or conformal coatings.Type: GrantFiled: April 19, 2000Date of Patent: August 7, 2001Assignee: General Electric CompanyInventors: Sylvie Louise Boileau, Anna Elzbieta Kowalewska, Laurent Bouteiller, Matthew David Butts, Slawomir Rubinsztajn
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Patent number: 6153648Abstract: Iodopropargylamine compound of the general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R.sup.1 and R.sup.2 combine with each other to form a tetramethylene group or a pentamethylene group, R.sup.3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and X and Y each independently represent a cyano group, an alkoxycarbonyl group having 2 to 7 carbon atoms, an alkylcarbonyl group having 2 to 7 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a phenylcarbonyl group or a phenylsulfonyl group, provided that the phenyl group of a phenylcarbonyl group or a phenylsulfonyl group may be optionally substituted by halogen atoms, alkyl groups having 1 to 3 carbon atoms, alkoxy groups having 1 to 3 carbon atoms, nitro groups or trifluoromethyl groups.Type: GrantFiled: February 23, 2000Date of Patent: November 28, 2000Assignee: Nissan Chemical Industries, Ltd.Inventors: Kenji Makino, Shinichi Igarashi, Mitsugu Futagawa
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Patent number: 6087535Abstract: This invention provides an improved process for the preparation of chloroalkynes from alkynyl alcohols. The chloroalkynes can be employed to prepare alkynyl amines which are useful for the manufacture of biologically active materials. The present invention reduces the hazards of the chlorination reaction, eliminates or greatly reduces by-product formation, and provides certain environmental benefits.Type: GrantFiled: January 7, 1999Date of Patent: July 11, 2000Assignee: Rohm and Haas CompanyInventors: Renee Caroline Roemmele, Andrew William Gross, David Wayne Mosley
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Patent number: 5929287Abstract: This invention relates to a process for the selective monochlorination or dichlorination of certain substituted alkenes using trichloroisocyanuric acid. The chlorinated alkenes can be easily hydrolyzed to provide .alpha.-monochloroketones or .alpha.,.alpha.-dichloroketones with a high degree of selectivity. The resulting .alpha.-monochloroketones or .alpha.,.alpha.-dichloroketones have utility as fungicides or function as useful intermediates for fungicides.Type: GrantFiled: April 13, 1998Date of Patent: July 27, 1999Assignee: Rohm and Haas CompanyInventors: Renee Caroline Roemmele, Heather Lynnette Rayle
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Patent number: 5723703Abstract: A process for the removal of (cyclo)aliphatic hexene and hexadiene isomers from allyl chloride, characterized by a chlorination step which is performed in the liquid phase.Type: GrantFiled: July 19, 1995Date of Patent: March 3, 1998Assignee: Shell Oil CompanyInventors: Abe Wiebe De Jong, Timothy Michael Nisbet
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Patent number: 5545388Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.Type: GrantFiled: March 29, 1995Date of Patent: August 13, 1996Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5504173Abstract: Process for preparing the (E)-isomer of a compound (II) by contacting the (E) or (Z) isomer of the 2-methylphenyl precursor, or a mixture of both, with bromine in an organic solvent, in the presence of a polymeric base and light.Type: GrantFiled: February 9, 1995Date of Patent: April 2, 1996Assignee: Zeneca LimitedInventors: Alfred G. Williams, Nicholas R. Foster
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Patent number: 5478548Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.Type: GrantFiled: February 4, 1994Date of Patent: December 26, 1995Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5334789Abstract: Disclosed are an oxychlorination catalyst comprising a carrier material, and a palladium compound, a copper compound and a vanadium compound which are supported on the carrier material; an oxychlorination catalyst comprising a carrier material, and a palladium compound, a copper compound, a vanadium compound and an alkaline earth metal compound which are supported on the carrier material; processes for preparing these catalysts; and a method for oxychlorination of an olefin or an aromatic hydrocarbon using one of these catalysts.Type: GrantFiled: June 30, 1993Date of Patent: August 2, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Komatsu, Michio Yamamoto, Masaru Ishino, Gohfu Suzukamo
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Patent number: 5332791Abstract: Hydrocarbons and polymers thereof, of the structure (I)R--C(CH.sub.3).sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --Cl (I)where R is a hydrocarbon radical, are prepared by reacting corresponding starting materials which contain chlorine bonded to tertiary carbon, of the structureR--C(CH.sub.3).sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --Cl (II)with from 1 to 10 moles of butadiene in the presence of a Friedel-Crafts catalyst in a solvent which is inert to the catalyst, and the hydrocarbons or polymers thereof can be reacted in a further step of the process with a compound from the group comprising ammonia, primary or secondary amine or polyamine, amino alcohol, amino ether, hydrazine or hydrazine which is substituted up to three times.Type: GrantFiled: November 16, 1992Date of Patent: July 26, 1994Assignee: BASF AktiengesellschaftInventors: Konrad Knoll, Klaus Bronstert, Dietmar Bender
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Patent number: 5292973Abstract: An improvement is proposed for the removal of the precipitates of a phosphine oxide compound as a by-product from a mixture thereof with an olefin compound obtained by the Wittig reaction for the preparation of the olefin compound from a phosphorane compound and a carbonyl compound. Instead of the conventional procedure of filtration to remove the precipitates, the mixture in a hydrocarbon solvent, after replacement of a non-hydrocarbon solvent with a hydrocarbon solvent, if necessary, is admixed with a lower carboxylic acid such as acetic acid so that the precipitates of the phosphine oxide are dissolved forming a viscous fluid which is immiscible with the mixture of the olefin compound and the hydrocarbon solvent. The fluid containing the dissolved phosphine oxide compound can be easily removed by phase separation so that a great increase is obtained in the yield of the desired olefin compound.Type: GrantFiled: June 24, 1993Date of Patent: March 8, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Akira Yamamoto
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Patent number: 5283383Abstract: The present invention relates to a new antitumor compound, a method for isolating same from a red alga, antitumor compositions containing same and methods of using same for treating patients with cancer. The compound of the present invention is 6(R)-bromo-3(S)-bromomethyl-7-methyl-2,3,7-trichloro-1-octene.Type: GrantFiled: February 18, 1992Date of Patent: February 1, 1994Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Michael R. Boyd, John H. Cardellina, II, Richard W. Fuller, Kenneth M. Snader, Jon Clardy
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Patent number: 5247124Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: August 25, 1992Date of Patent: September 21, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5243109Abstract: Tribromostyrene (TBS) is produced by the preparation of a TBS precursor, which is .beta.-bromoethyl-tribromobenzene (.beta.-BrBr.sub.3), and the successive elimination of hydrogen bromide from said precursor. The precursor is prepared by selective bromination of phenethyl bromide (.beta.-Br), wherein the molar ratio of bromine to phenethyl bromide is comprised between 2.5 and 3.5, and preferably between 3.1 and 3.3 included; and by adding bromine, after an initial addition, at a controlled molar rate.Type: GrantFiled: August 6, 1992Date of Patent: September 7, 1993Assignee: Bromine Compounds Ltd.Inventors: Nurit Kornberg, David Beneish, Michael Peled
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Patent number: 5175382Abstract: 1,2-Dichloroethane is prepared by reacting ethylene, hydrogen chloride and oxygen or an oxygen-containing gas in the presence of a copper-containing catalyst by a process in which first hydrogen chloride and oxygen or an oxygen-containing gas are reacted in the presence of the catalyst, then ethylene is added, and the mixture is reacted in the presence of the said catalyst.Type: GrantFiled: January 5, 1988Date of Patent: December 29, 1992Inventors: Werner Hebgen, Gerd Krome, Erhard Stahnecker
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Patent number: 5118874Abstract: Compounds of the formula ##STR1## in which, independently of one another, each R is OH or lower alkyl having 1-4 carbon atoms and each R' is hydrogen or lower alkyl having 1-4 carbon atoms, are prepared by the condensation of partially fluorinated aromatic hydrocarbons in the presence of hydrogen fluoride or by the reductive coupling of partially fluorinated aromatic compounds. The compounds are used as a starting material for the preparation of partially fluorinated polycondensates.Type: GrantFiled: June 20, 1991Date of Patent: June 2, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Appel, Gunter Siegemund
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Patent number: 5091603Abstract: In the process, a copper/rhodium catalyst impregnated with 0.1 to 10.0% by weight, based on the total weight of active charcoal catalyst support and active components, of a water-soluble phosphonium halide is employed for the preparation of trichloroelethylene from perchloroethylene and hydrogen.Type: GrantFiled: October 22, 1990Date of Patent: February 25, 1992Assignee: Wacker-Chemie GmbHInventors: Willibald Dafinger, Wolfdietrich Gabler, Eduard Pichl, Roman Hierzegger
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Patent number: 5073659Abstract: A terpene compound having the formula (III) is produced by reacting an allylic halide having the formula (I) with a Grignard reagent having the formula (II) in the presence of anhydrous zinc chloride and a copper compound or an organic zinc halide compound having the formula (IV) in the presence of a copper compound, provided that when A-A is C-C, R' is hydrogen and when A-A is C=C, X is chlorine.Type: GrantFiled: August 10, 1990Date of Patent: December 17, 1991Assignee: Eisai Co., Ltd.Inventors: Kichisaburo Hamamura, Yutaka Ohnuki, Yukio Narabe, Yoshihiro Hisatake, Takashi Banba, Shizumasa Kijima
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Patent number: 5055622Abstract: Novel Styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.Type: GrantFiled: September 12, 1990Date of Patent: October 8, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
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Patent number: 5030764Abstract: Novel styryl-tetrahydronaphthalene and indane derivatives useful for treating neoplasms and dermatoses.Type: GrantFiled: October 15, 1990Date of Patent: July 9, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
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Patent number: RE34761Abstract: In the process, a copper/rhodium catalyst impregnated with 0.1 to 10.0% by weight, based on the total weight of active charcoal catalyst support and active components, of a water-soluble phosphonium halide is employed for the preparation of trichloroelethylene from perchloroethylene and hydrogen.Type: GrantFiled: October 15, 1993Date of Patent: October 18, 1994Assignee: Wacker-Chemie GmbHInventors: Willibald Dafinger, Wolfdietrich Gabler, Eduard Pichl, Roman Hierzegger