Forming Carbon To Carbon Multiple Bond Patents (Class 558/142)
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Publication number: 20140005434Abstract: The present invention relates to an intermediate (12) of lycopene of 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecantriene of formula, (12) and its intermediate of 4-methyl-5,5-dialkoxyl-1-pentenyl-1-phosphonic acid dialkyl ester of formula (10), and their preparation methods. The process route is simple, the starting materials are available easily, the cost is low, and it is valuable in industry.Type: ApplicationFiled: December 3, 2012Publication date: January 2, 2014Applicants: Shaoxing University, Zhejiang Medicine Co., Ltd. XinchangInventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Patent number: 8329935Abstract: A process for efficiently producing through a small number of steps an N-substituted 2-amino-4-(substituted-oxymethylphosphinyl)-2-butenoic ester which is an intermediate for herbicide L-AMPB. The process comprises reacting a compound represented by the following formula (1): (where R1 represents C1-4 alkyl group) with a compound represented by the following formula (2): (wherein R2, R2?, and R3 each represents C1-4 alkyl and R4 represents benzyloxycarbonyl) in the presence of a base.Type: GrantFiled: March 19, 2008Date of Patent: December 11, 2012Assignee: Meji Seika Kaisha Ltd.Inventors: Kenichi Kurihara, Nobuto Minowa, Nozomu Nakanishi, Masaaki Mitomi
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Publication number: 20120135134Abstract: 1-OH-2-acyl-sn-glycero-3-phosphocholine compounds and its analogs, pure or mixed, having formula WCH2CHXCH2PO3YCH2CH2Z, where W is preferably a hydroxyl group or an O-acyl group containing from 2 to 22 carbon atoms, and where X is preferably an O-acyl group containing from 2 to 22 carbon atoms or a hydroxyl (OH) and where Y may be an (O?) or OH and where Z is preferably a trimethyl-ammonium group [N+(CH3)3] can be protonated dimethyl ammonium [N+H(CH3)2] group. In the O-acyl groups containing 18 carbon atoms can be observed from 0 to 3 instaurations, useful as biocidal agents; processes for their preparation; and antifouling compositions, preferably paints useful in susceptible fouling surfaces, such as hulls of vessels.Type: ApplicationFiled: November 30, 2011Publication date: May 31, 2012Applicants: Universidade Federal do Rio de Janeiro - UFRJ, Universidade Federal Fluminense - UFF, Instituto de Estudos Do Mar Almirante Paulo Morera - IEAPMInventors: William Romao Batista, Ricardo Coutinho, Maria Helena Campos Beta Neves, Claudio Cerqueira Lopes, Rosangela Sabbatini Capella Lopes, Vanessa de Almeida Martins, Renato Crespo Pereira
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Patent number: 6479687Abstract: A process for preparing vinylphosphonic acid compounds of the formula (I) where R1 and R2 are, independently, H, C1-16-alkyl, C6-12-aryl, C7-12-alkaryl or C7-12-aralkyl, it being possible for the organic radicals to be substituted by one or more halogen atoms, hydroxyl, acyl or acetoxy groups, by reacting phosphorous acid compounds of the formula (II) with acetylene in the presence of a Pd(O) complexe or Pt(O) complex as catalyst.Type: GrantFiled: March 12, 2001Date of Patent: November 12, 2002Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Thomas Preiss, Arnd Böttcher
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Patent number: 6429329Abstract: A process for the synthesis of a hydrocarbylvinyl-1-phosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester, which utilizes: (a) the base catalyzed addition (preferably using a nonnucleophilic strong organic base) of a hydrocarbyl phosphite, such as a dialkyl phosphite containing no more than about eight carbon atoms in either of its alkyl groups, to an aldehyde or methyl ketone, such as a phenyl ketone, as exemplified by acetophenone, to form a hydrocarbyl 1-hydroxy-1-hydrocarbylphosphonate, such as a dialkyl 1-hydroxy-1-phenylalkylphosphonate compound; (b) the acid-catalyzed esterification (preferably acetylation) of the compound from (a) with an acid anhydride to form an acylated intermediate; and (c) the removal of carboxylic acid (preferably at a temperature of from about 50° C. to about 215° C.Type: GrantFiled: September 9, 1996Date of Patent: August 6, 2002Assignee: Akzo Nobel NVInventors: Alan M. Aaronson, John Tomko, Jeffrey E. Telschow, Johannes Hermanus Boelee, Fred Jaffe
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Patent number: 6215013Abstract: A method for the preparation of alkene phosphonic acids and salts thereof, such as VDPA (vinylidene diphosphonic acid) is disclosed. The products can be produced in a stable, substantially pure form and in high yield. The method includes the azeotropic removal of water from salts of &agr;-hydroxy-alkane diphosphonic acid dimer or corresponding acids thereof, and the pyrolysis of the dehydrated reactant at a temperature of from 170° C. to 300° C. There may be included a step to convert anhydrides which have been formed during the pyrolysis. The method may include the use of heat transfer agents and/or bases, and may be carried out at elevated or reduced pressure.Type: GrantFiled: September 5, 2000Date of Patent: April 10, 2001Assignee: Rhodia Consumer Specialties LimitedInventors: Gary Woodward, Timothy Kevin Brierley, Ranbir Singh Padda, John Christopher Harris, Aidan Michael Hayes
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Patent number: 6191298Abstract: A phosphonic acid ester compound of the formula: R1C(SR3)═CHP(═O)(OR2)2 or [P(═O)(OR2)2]CH═C(SR3)—R4—C(SR3)═CH[P(═O)(OR2)2] wherein R1 represents a monovalent group selected from hydrogen, alkyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkenyl and silyl, R2 and R3 each represent aryl and R4 represents alkylene or cycloalkylene. The ester compound is produced by reaction of an acetylene compound, R1C≡CH or HC≡C—R4—C≡CH, with with a phosphorothioate, (R2O)2P(═O)SR3, in the presence of a palladium complex catalyst.Type: GrantFiled: March 9, 2000Date of Patent: February 20, 2001Assignee: Agency of Industrial Science and TechnologyInventors: Li-Biao Han, Masato Tanaka
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Patent number: 5763637Abstract: The invention relates to a process for preparing dimethyl vinylphosphonate by thermal dissociation of dimethyl 2-acetoxyethanephosphonate in the gas phase, which comprises vaporizing dimethyl 2-acetoxyethanephosphonate and dissociating it without catalysis at a temperature of from 400.degree. to 700.degree. C. into dimethyl vinylphosphonate and acetic acid.Type: GrantFiled: January 17, 1996Date of Patent: June 9, 1998Assignee: Hoechst AktiengesellschaftInventors: Knut Riedel, Udo Dettmeier, Guenter Roscher
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Patent number: 5654462Abstract: This invention is selected novel chiral (essentially pure) alpha-amino phosphonates, process for the preparation which is a catalytic asymmetric hydrogenation of olefins and novel intermediates therefor. The alpha-amino phosphonates are useful as antibiotics and/or as intermediates in the preparation of phosphorus-containing analogs of peptides, i.e., phosphonopeptides or pseudopeptides having known uses, such as in antibiotics, antibiotic enhancers, or enzyme inhibitors.Type: GrantFiled: March 14, 1995Date of Patent: August 5, 1997Assignee: Monsanto CompanyInventor: John J. Talley
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Patent number: 5475128Abstract: Process for the continuous preparation of dialkyl vinylphosphonates using catalysts at temperatures of from 150.degree. to 270.degree. C. by dissociation of dialkyl acetoxyethanephosphonates at a pressure of from 5 to 500 mbar in contact with a liquid, catalytically active medium while drawing off the dialkyl vinylphosphonates formed and other volatile reaction products as vapors, by conveying the liquid medium in forced circulation via an evaporator while feeding in fresh dialkyl acetoxyethanephosphonate, if desired admixed with catalyst, corresponding to the distillation of dialkyl vinylphosphonates and other volatile compounds, and drawing off non-volatile material formed as byproduct from the liquid circuit to maintain constant conditions.Type: GrantFiled: December 12, 1994Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Gunter Roscher, Wolf-Dietmar Kaufmann, Bernd Laugwitz
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Patent number: 5442085Abstract: A method of making a monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The monomer is manufactured by combining an aqueous secondary amine solution with a formaldehyde and a tetra (alkyl) methylene diphosphonate. The resulting mixture is maintained at a pH above about 6 and refluxed for two hours to enable reaction to produce the monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The product monomer is then purified to produce the final end product.Type: GrantFiled: October 5, 1993Date of Patent: August 15, 1995Assignee: The University of Tennessee Research CorporationInventor: Spiro D. Alexandratos
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Patent number: 5256808Abstract: A method of making a monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The monomer is manufactured by combining an aqueous secondary amine solution with a formaldehyde and a tetra (alkyl) methylene diphosphonate. The resulting mixture is maintained at a pH above about 6 and refluxed for two hours to enable reaction to produce the monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The product monomer is then purified to produce the final end product.Type: GrantFiled: December 4, 1992Date of Patent: October 26, 1993Assignee: The University of Tennessee Research Corp.Inventor: Spiro D. Alexandratos
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Patent number: 5132444Abstract: A process for the preparation of vinyl phosphonic derivatives of the general formula I ##STR1## in which R.sup.1 and R.sup.2 are the same or different and may stand for hydrogen or a C.sub.1 -C.sub.8 -alkyl, a C.sub.6 -C.sub.10 -aryl, or a C.sub.8 -C.sub.10 -aralkyl radical optionally substituted by Cl or Br, and in which R.sup.1 and R.sup.2 may alternatively be joined together to form an alicyclic ring having from 3 to 12 carbon atoms in the ring, wherein an ethane phosphonic ester of the general formula II ##STR2## in which R.sup.3 and R.sup.4 have the meanings stated above for R.sup.1 and R.sup.2 except for hydrogen and X denotes a hydroxy group, a halogen atom, or a radical of the formula--OR.sup.5,in which R.sup.5 is a hydrogen atom or a radical of the formula ##STR3## in which R.sup.6 is a C.sub.1 -C.sub.6 -alkyl radical or an alicyclic ring, is converted in the gas phase in the presence of a solid catalyst.Type: GrantFiled: April 22, 1991Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Andreas Northemann, Martin Fischer, Ludwig Wambach
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Patent number: 5061819Abstract: Processes for synthesizing novel phosphonate diester compounds of the general formula ##STR1## are disclosed and claimed. The claimed process includes forming a reaction mixture of a C-14 aldehyde and a methylene-bis-phosphonic acid ester, separating a pentadienyl phosphonic acid dialkyl ester intermediate from the reaction mixture, optionally isomerizing the intermediate in the presence of a basic catalyst, and isolating the desired pentadienylphosphonic acid dialkyl ester compound. The isolated phosphonate compounds made according to the processes of the present invention may be employed in synthesizing retinoids such as retinoic acid or carotenoids such as beta-carotene.Type: GrantFiled: February 5, 1990Date of Patent: October 29, 1991Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 4960919Abstract: A process for the preparation of alkyl esters of alkenylphosphinic acid, having the general formula I ##STR1## wherein R.sup.1 represents H or CH.sub.3, R.sup.2 alkyl having from 1 to 4 carbon atoms or phenyl and R.sup.3 alkyl having from 1 to 8 carbon atoms, which comprises cleaving an alkyl ester of 2-acetoxyethyl phosphinic acid, having the general formula II ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the meaning indicated above, in contact with a liquid catalytically acting medium and at a partial pressure of the total of the components of the reaction system in the range of from 1 to 500 mbar, and drawing off the resulting alkyl esters of alkenyl phosphinic acid and other volatile reaction products.The invention also relates to compounds of the formula I ##STR3## wherein (a) R.sup.1 represents H, R.sup.2 represents alkyl having from 1 to 4 carbon atoms or phenyl and R.sup.3 represents isobutyl or alkyl having from 5 to 8 carbon atoms, or(b) R.sup.1 represents CH.sub.3, R.sup.Type: GrantFiled: February 16, 1989Date of Patent: October 2, 1990Assignee: Hoechst AktiengesellschaftInventors: Hans-Jerg Kleiner, Gunter Roscher
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Patent number: 4939284Abstract: Disclosed are tetraalkyl enthenylidenebisphosphonates and a method for their manufacture. These compounds are suitable for use as antimicrobial agents in combating a number of pathogenic microorganisms, such as bacteria, yeasts, viruses, fungi and protozoa, when used together with a pharmaceutically-acceptable carrier. Also disclosed is a method for treating infectious diseases by administering a safe and effective amount of these tetraalkyl ethenylidenebisphosphonates.Type: GrantFiled: January 24, 1989Date of Patent: July 3, 1990Assignee: The Procter & Gamble CompanyInventor: Charles R. Degenhardt
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Patent number: 4894470Abstract: A process for the production of dialkyl esters of vinyl phosphonic acid which comprises subjecting dialkyl esters of 2-acetoxyethane phosphonic acid to cleavage by contacting with a liquid catalytically acting medium at a temperature in the range from 150.degree. to 270.degree. C. and under a pressure such that the partial pressures of the total of the components of the reaction system is in the range from 1 to 500 mbar, and drawing off the resulting dialkyl esters of vinyl phosphonic acid and other volatile reaction products.Type: GrantFiled: March 3, 1988Date of Patent: January 16, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Roscher, Hans-Jerg Kleiner, Gabriele Ihl, Hermann Leipe
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Patent number: 4879400Abstract: A process for producing an .alpha.-(benzylidene)acetonylphosphonate of the formula: ##STR1## wherein Ar is phenyl substituted by at least one substituent selected from the group consisting of fluorine, chlorine, bromine, nitro, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, --CO.sub.2 R.sup.7 wherein R.sup.7 is C.sub.1 -C.sub.5 alkyl, --CONR.sup.7 R.sup.8 wherein R.sup.7 is as defined above and R.sup.8 is C.sub.1 -C.sub.5 alkyl, --C(O)R.sup.7 wherein R.sup.7 is as defined above, --OC(O)R.sup.7 wherein R.sup.7 is as defined above, --OSO.sub.3 R.sup.7 wherein R.sup.7 is as defined above, --OCF.sub.3, --S(.dbd.O).sub.2 R.sup.7 wherein R.sup.7 is as defined above, --CN and --SO.sub.3 R.sup.7 wherein R.sup.7 is as defined above, and each of R.sup.1 and R.sup.2 which may be the same or different is a saturated or unsaturated C.sub.1 -C.sub.12 aliphatic group, or R.sup.1 and R.sup.Type: GrantFiled: January 19, 1988Date of Patent: November 7, 1989Assignee: Nissan Chemical Industries Ltd.Inventors: Kiyotomo Seto, Hiroo Matsumoto, Ryozo Sakoda
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Patent number: 4808743Abstract: Vinyl chloroformates are described of formula ##STR1## in which: R.sub.1 .dbd.R.sub.2 .dbd.Cl, Br or a saturated 1-4 carbon atom alkyl or together they form a cycloaliphatic ring of 4-8 carbon atoms;R.sub.3 .dbd.H when R.sup.1 or R.sup.2 .dbd.alkyl; saturated alkyl of 1-4 carbon atoms or aryl; ##STR2## in which R.sub.4 .dbd.R.sub.5 .dbd.alkyl of 1-4 carbon atoms or R.sub.3 forms with R.sub.2 a C.sub.5 -C.sub.8 ring which may have attached oxygen atoms. The process of preparation consists of reacting phosgene with the corresponding compounds containing alpha halogen and a carbonyl group. The products are very useful to obtain vinyl carbonates and carbamates.Type: GrantFiled: February 13, 1987Date of Patent: February 28, 1989Assignee: Societe Nationale des Poudres et ExplosifsInventors: Mark Bowman, Roy Olofson, Thierry Malfroot, Jean-Pierre Senet
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Patent number: 4608207Abstract: Dialkyl vinylphosphonates are prepared by heating the new dialkyl 2-alkylcarbonatoethanephosphonates in the presence of catalysts. Also disclosed is a process for making the new dialkyl 2-alkylcarbonatoethanephosphonate by transesterification of a dialkyl 2-carboxyethanephosphonate with a dialkyl carbonate in the presence of a transesterification catalyst.Type: GrantFiled: May 4, 1984Date of Patent: August 26, 1986Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Peter Mues
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Patent number: 4582905Abstract: Convenient intermediates for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers, a reaction to the intermediates of the following formula and a conversion to obtain the said .beta.-blockers are disclosed. ##STR1## (wherein X is hydrogen or halogen; Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino;one of P and R combined together with Q represents lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy; hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen;and the remaining R or P is hydrogen or halogen;and dotted line represents the presence of one or two double bonds).Type: GrantFiled: December 20, 1984Date of Patent: April 15, 1986Assignee: Shionogi & Co., Ltd.Inventor: Makiko Sakai