Boron Or Phosphorus Attached Indirectly To The Sulfonate Group By Nonionic Bonding (e.g., Phosphonium Salts, Etc.) Patents (Class 562/35)
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Patent number: 11603379Abstract: The invention provides novel zwitterionic monomers and polymers (including copolymers) with pendent phosphonium-based zwitterionic moieties, and compositions and products comprising same, as well as related methods and uses of the compositions, for example, as surfactants, coatings, and interlayer materials, biomedical materials or agents.Type: GrantFiled: September 9, 2020Date of Patent: March 14, 2023Assignee: University of MassachusettsInventors: Marcel U. Brown, Todd Emrick
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Patent number: 8952193Abstract: One aspect of the present invention relates to amine-functionalized task-specific ionic liquids (TSILs). In certain embodiments, the ionic liquids of the invention comprise beta-hydroxy amines, aryl amines or tertiary amines. The TSILs may be used for gas capture, capitalizing on their non-volatile nature. In certain embodiments, the captured gas is selected from the group consisting of CO2, SO2, CS2, and NO2. Another aspect of the present invention relates to a library of CO2-philic salts, which library facilitates reactive gas separation. In certain embodiments, the CO2-philic salts are CO2-reactive TSILs. In certain embodiments, the CO2-philic salts are resinous or plastic in nature.Type: GrantFiled: September 17, 2013Date of Patent: February 10, 2015Assignee: University of South AlabamaInventor: James H. Davis, Jr.
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Patent number: 8536371Abstract: One aspect of the present invention relates to amine-functionalized task-specific ionic liquids (TSILs). In certain embodiments, the ionic liquids of the invention comprise beta-hydroxy amines, aryl amines or tertiary amines. The TSILs may be used for gas capture, capitalizing on their non-volatile nature. In certain embodiments, the captured gas is selected from the group consisting of CO2, SO2, CS2, and NO2. Another aspect of the present invention relates to a library of CO2-philic salts, which library facilitates reactive gas separation. In certain embodiments, the CO2-philic salts are CO2-reactive TSILs. In certain embodiments, the CO2-philic salts are resinous or plastic in nature.Type: GrantFiled: April 2, 2008Date of Patent: September 17, 2013Assignee: University of South AlabamaInventor: James H. Davis, Jr.
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Publication number: 20110263879Abstract: A zwitterionic phosphonium salt of Formula I: wherein n is 0 or 1; R is H or SO3; R? is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, phenyl, substituted phenyl, benzyl and C1-C10 alkoxy-carbonyl; R? is CX3 when n is O; and X is selected from the group consisting of F, Cl, Br and I. The zwitterionic phosphonium salts are useful reagents for the preparation of alkenes and acetals from the corresponding aldehyde.Type: ApplicationFiled: July 29, 2009Publication date: October 27, 2011Applicant: THE HONG KONG POLYTECHNIC UNIVERSITYInventors: Tak-Hang Chan, Congde Huo, Xun He
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Publication number: 20110257351Abstract: To provide an industrially useful ?-olefin.((meth)acrylic acid)-based olefin copolymer having both a high molecular weight and a high comonomer content, a catalyst component capable of realizing a production of two different kinds of ?-olefin.((meth)acrylic acid)-based olefin copolymers, and a production process using the catalyst. An ?-olefin.((meth)acrylic acid)-based olefin copolymer is produced by using a metal complex complexed with a ligand represented by the following formula (Y is phosphorus or arsenic) for a catalyst composition.Type: ApplicationFiled: November 20, 2009Publication date: October 20, 2011Applicants: Japan Polypropylene Corporation, Japan Polyethylene CorporationInventors: Minoru Kobayashi, Hideshi Uchino, Kazuhiro Yamamoto, Toshiaki Egashira, Hiroyuki Shimizu, Tetsuya Morioka
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Publication number: 20110152537Abstract: The present invention relates to chemical compounds comprising a [Y(CHRa)n—CH(Ra)SO3]? anion, their preparation and application. The chemical compounds are preferably ionic liquids.Type: ApplicationFiled: May 12, 2009Publication date: June 23, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNGInventors: Peter Wasserscheid, Natalia Paape, Andreas Boesmann, Peter Schulz
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Patent number: 7829739Abstract: The present invention relates to compositions of matter that are ionic liquids, the compositions comprising any of eleven cations combined with any of three fluorinated sulfonated anions. Compositions of the invention should be useful as solvents and, perhaps, as catalysts for many reactions, including aromatic electrophilic substitution, nitration, acylation, esterification, etherification, oligomerization, transesterification, isomerization and hydration.Type: GrantFiled: May 27, 2009Date of Patent: November 9, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Jemma Vickery
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Patent number: 7767846Abstract: A novel class of compounds that includes HPTS-Cys-MA, and methods of making them are disclosed herein. The class of compounds including HPTS-Cys-MA are useful as fluorescent dyes for analyte detection.Type: GrantFiled: August 22, 2008Date of Patent: August 3, 2010Assignee: Glumetrics, Inc.Inventor: Jeff T Suri
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Publication number: 20090253907Abstract: A phosphine compound represented by general formula (1) wherein R? and R? independently are selected from alkyl, cycloalkyl and 2-furyl radicals, or R? and R? are joined together to form with the phosphorous atom a carbon-phosphorous monocycle including at least 3 carbon atoms or a carbon-phosphorous bicycle; the alkyl radicals, cycloalkyl radicals, and carbon-phosphorous monocycle being unsubstituted or substituted by at least one radical selected from the group of alkyl, cycloalkyl, aryl, alkoxy, and aryloxy radicals; Cps is a partially substituted or completely substituted cyclopentadien-1-yl group, including substitutions resulting in a fused ring system, and wherein a substitution at the 1-position of the cyclopentadien-1-yl group is mandatory when the cyclopentadien-1-yl group is not part of a fused ring system or is part of an indenyl group. These phosphines can be used as ligands in catalytic reactions.Type: ApplicationFiled: August 14, 2007Publication date: October 8, 2009Inventors: Herbert Plenio, Christoph Fleckenstein, Renat Kadyrov, Juan Almena, Axel Monsees, Thomas Riermeier
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Patent number: 7417164Abstract: A novel class of compounds that includes HPTS-Cys-MA, and methods of making them are disclosed herein. The class of compounds including HPTS-Cys-MA are useful as fluorescent dyes for analyte detection.Type: GrantFiled: July 24, 2007Date of Patent: August 26, 2008Assignee: Glumetrics Inc.Inventor: Jeff T. Suri
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Patent number: 7339075Abstract: Ligand synthesis methods for the preparation of ligands having the formula wherein Q is selected from phosphorus, arsenic and antimony; wherein X1, X2 and X3 are carbon anions; and, wherein R15 is selected from —SO3, —SO2N(R18), —CO2, —PO3, —AsO3, —SiO2, —C(CF3)2O; where R18 is selected from a hydrogen, a halogen, a hydrocarbyl group and a substituted hydrocarbyl group, are disclosed. Also disclosed are methods of complexing the ligands with late transition metals to form catalyst complexes that catalyze polymerization reactions and/or Heck coupling reactions.Type: GrantFiled: July 17, 2006Date of Patent: March 4, 2008Assignee: Rohm and Haas CompanyInventors: Nathan Tait Allen, Brian Leslie Goodall, Thomas Cleveland Kirk, Lester Howard McIntosh, III
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Patent number: 7041619Abstract: Phosphonium salts represented by the general formula (I) wherein R1 and R2 each represents a phenyl group which may be substituted by a lower alkyl group, R3 represents a phenylene group which may be substituted by a lower alkyl group, R7 and R8 each represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may be substituted and R9 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may be substituted; processes for producing the same and uses for the same; phosphines providing the same, and processes for producing said phosphines.Type: GrantFiled: July 22, 2004Date of Patent: May 9, 2006Assignee: Kuraray Co., Ltd.Inventors: Kazuyuki Yada, Kenji Shimoyamada, Masahiro Muranaka, Junichi Fuji, Shigeaki Suzuki
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Patent number: 6864387Abstract: A process for preparing solutions of sulfonated arylphosphines comprising reacting arylphosphines with oleum, diluting the sulfonation mixture with water, extracting the diluted sulfonation mixture with a solution of a water-insoluble organic solvent, reacting the organic phase with a solution of an inorganic base in water, adjusting the resulting aqueous solutin of sulfonated arylphosphines to a pH of up to 3 by addition of an acid, and passing an inert gas stream through the aqueous solution comprising sulfonated arylphosphines until sulfur is no longer liberated from the aqueous solution of sulfonated arylphosphines.Type: GrantFiled: April 14, 2003Date of Patent: March 8, 2005Assignee: Celanese Chemicals Europe GmbHInventors: Michael Riedel, Ernst Wiebus, Carl D Frohning, Wilfried Fenske, Florian Rampf, Jurgen Herwig, Helmut Bahrmann, Klaus Bergrath, Wolfgang Zgorzel-Ski, Robert Eckl, Hans Bohnen, Richard Fischer, Kurt Schalapski, Wolfgang Greb
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Publication number: 20040260118Abstract: Phosphonium salts represented by the general formula (I) 1Type: ApplicationFiled: July 22, 2004Publication date: December 23, 2004Applicant: KURARAY CO. LTD.Inventors: Kazuyuki Yada, Kenji Shimoyamada, Masahiro Muranaka, Junichi Fuji, Shigeaki Suzuki
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Patent number: 6790985Abstract: Phosphonium salts represented by the general formula (I) wherein R1 and R2 each represents a phenyl group which may be substituted by a lower alkyl group, R3 represents a phenylene group which may be substituted by a lower alkyl group, R7 and R8 each represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may be substituted and R9 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may be substituted; processes for producing the same and uses for the same; phosphines providing the same, and processes for producing said phosphines.Type: GrantFiled: April 1, 2002Date of Patent: September 14, 2004Assignee: Kuraray Co., Ltd.Inventors: Kazuyuki Yada, Kenji Shimoyamada, Masahiro Muranaka, Junichi Fuji, Shigeaki Suzuki
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Publication number: 20040019236Abstract: A process for preparing solutions of sulfonated arylphosphines comprising reacting arylphosphines with oleum, diluting the sulfonation mixture with water, extracting the diluted sulfonation mixture with a solution of a water-insoluble organic solvent, reacting the organic phase with a solution of an inorganic base in water, adjusting the resulting aqueous solutin of sulfonated arylphosphines to a pH of up to 3 by addition of an acid, and passing an inert gas stream through the aqueous solution comprising sulfonated arylphosphines until sulfur is no longer liberated from the aqueous solution of sulfonated arylphosphines.Type: ApplicationFiled: April 14, 2003Publication date: January 29, 2004Applicant: Celanese Chemicals Europe GmbHInventors: Michael Riedel, Ernst Wiebus, Carl D. Frohning, Wilfried Fenske, Florian Rampf, Jurgen Herwig, Helmut Bahrmann, Klaus Bergrath, Wolfgang Zgorzel-Ski, Robert Eckl, Hans Bohnen, Richard Fischer, Kurt Schalapski, Wolfgang Greb
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Patent number: 6613939Abstract: Water-soluble sulfonated organophosphorus compounds are purified by at least partially removing contaminating sulfite values therefrom, by decreasing the pH of a solution of such sulfonated organophosphorus compounds to a value of less than or equal to 4, and maintaining the pH of the solution at this value of 4 or less for such period of time as to reduce the weight concentration of sulfite in the solution to less than 100 ppm; the organophosphorus compounds thus purified are well suited for the two-phase cocatalysis of a wide variety of organic reactions.Type: GrantFiled: June 25, 2001Date of Patent: September 2, 2003Assignee: Rhodia Fiber & Resin IntermediatesInventors: Larbi Aouni, Paolo Burattin, Pierre Coqueret, Marc Huser
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Patent number: 6610881Abstract: The invention relates to a method for producing sulfonated aryl phosphines by reacting aryl phosphines with oleum. After reacting the aryl phosphines with oleum, the sulfonation mixture is firstly diluted with water and an inert gas stream is then fed through the diluted sulfonation mixture until SO2 is no longer released from the diluted sulfonation mixture. Afterwards, the sulfonation mixture is subsequently processed in a usual manner. The invention also relates to a method for producing solutions of sulfonated aryl phosphines by reacting the aryl phosphines with oleum, diluting the sulfonation mixture with water, extracting the aqueous solution using an organic solution consisting of an amine, and subsequently carrying out a reextraction using an aqueous solution having an inorganic base.Type: GrantFiled: December 12, 2001Date of Patent: August 26, 2003Assignee: Celanese Chemicals EuropeInventors: Michael Riedel, Jurgen Herwig, Helmut Bahrmann, Klaus Bergrath, Wolfgang Zgorzel-Ski, Robert Eckl, Ernst Wiebus, Carl D Frohning, Wilfried Fenske, Florian Rampf
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Patent number: 6590100Abstract: The present invention provides a process for preparing a polyaromatic compound comprising at least one sequence of two aromatic rings. The process of the invention, which consists in reacting an aromatic compound bearing a leaving group and an arylboronic acid and/or its derivatives in the presence of a base and an effective amount of a nickel catalyst, is characterized in that the reaction is conducted in a reaction solvent which is water optionally in a mixture with an organic solvent and in the presence of an effective amount of a catalyst based on nickel with at least one water-soluble phosphine ligand.Type: GrantFiled: May 15, 2002Date of Patent: July 8, 2003Assignee: Rhodia ChimieInventors: Jean-Christophe Galland, Monique Savignac, Jean-Pierre Genet
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Publication number: 20020065434Abstract: Bidentate phosphine ligands of the formula 1Type: ApplicationFiled: November 13, 2001Publication date: May 30, 2002Inventors: Holger Geissler, Petrus W.N.M. van Leeuwen, Paul C. J. Kamer, Lars A. van der Veen
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Publication number: 20020032339Abstract: The invention provides a process for covalently coupling organic compounds which comprises reacting an aromatic ring compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitabIe base. The invention also provides useful arylboron intermediates.Type: ApplicationFiled: December 18, 1998Publication date: March 14, 2002Inventors: SEBASTIAN MARIO MARCUCCIO, MARY RODOPOULOS, HELMUT WEINGOLD
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Patent number: 6160168Abstract: Process for the preparation of octa-2,7-dienyl-1-amine by telomerization of butadiene with ammonia in a two-phase system in the presence of hydrophilic palladium complexes, characterized in that octa-2,7-dienyl-1-amine and octa-1,7-dienyl-3-amine are isolated separately from one another from the reaction mixture present after telomerization, and the octa-1,7-dienyl-3-amine isolated in this way is subjected to an isomerization reaction to form octa-2,7-dienyl-1-amine, and also novel triphenylphosphine mono- and dimethoxytri(sodium sulphonates) and the use of triphenylphosphine trimethoxytri(sodium sulphonates), triphenylphosphine trimethyltri(sodium sulphonates) and triphenylphosphine trifluorodi- and tri(sodium sulphonates) as ligands for the preparation of palladium complexes.Type: GrantFiled: February 24, 2000Date of Patent: December 12, 2000Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Traenckner, Jorg-Dietrich Jentsch, Thomas Prinz, Birgit Driessen-Holscher, Wilhelm Keim
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Patent number: 6103908Abstract: Nonaqueous ionic ligand liquids of the formula (Q.sup..sym.)a A.sup.a-, where Q.sup..sym. is a singly charged quaternary ammonium and/or phosphonium cation or the equivalent of a multiply charged ammonium and/or phosphonium cation and A.sup.a- is a sulfonated triarylphosphine, a process for preparing them and their use as catalyst constituents.Type: GrantFiled: December 16, 1998Date of Patent: August 15, 2000Assignee: Celanese GmbHInventors: Helmut Bahrmann, Markus Schulte
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Patent number: 5929273Abstract: The present invention provides novel water-soluble diphosphines having the formula ##STR1## wherein X, Y, R.sub.1-18 and n are defined herein, and which can be complexed with a transition metal to form a novel catalyst useful in such applications as hydroformylation.Type: GrantFiled: April 18, 1996Date of Patent: July 27, 1999Assignee: Celanese International CorpInventors: Christian W. Kohlpaintner, Brian E. Hanson, Hao Ding
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Patent number: 5925785Abstract: The invention relates to secondary and tertiary phosphines of the formula ##STR1## in which R is hydrogen, an aryl or benzyl group or a straight-chain or branched alkyl group, n is 1 or 2 and M is potassium or sodium.These phosphines are prepared by reacting either alkali metal salts of fluorobenzene-2,4-disulfonic acid with phosphine or with primary or secondary phosphines, or secondary phosphines of the type HP?C.sub.6 H.sub.3 -2,4-(SO.sub.3 M).sub.2 !.sub.2 with a compound RX in which R is an alkyl, aryl or benzyl group and X is a halogen, in an aprotic solvent in the presence of at least stoichiometric quantities of a solid, powdered alkali metal hydroxide at temperatures of from 0 to 100.degree. C.Type: GrantFiled: March 20, 1997Date of Patent: July 20, 1999Assignee: Celanese GmbHInventors: Othmar Stelzer, Oliver Herd, Norbert Weferling
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Patent number: 5847200Abstract: New diphosphines in the form of ammonium carboxylates, sulfonates or phosphonates having a singly or multiply charged diphosphine anion and the corresponding number of ammonium cations as counter ions, and a process for their preparation useful as ligand in rhodium catalyst systems for hydroformylation of olefins.Type: GrantFiled: April 17, 1997Date of Patent: December 8, 1998Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Thomas Muller
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Patent number: 5827794Abstract: The present invention relates to water soluble chiral sulfonated 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and its use as organometallic catalysts for asymmetric synthesis of optically active compounds. Asymmetric reactions of the present invention include those reactions in which organometallic catalysts are commonly used. Such reactions include, but are not limited to, reduction and isomerization reactions on unsaturated substrates and carbon--carbon bond forming reactions. Examples of such reactions include, but are not limited to, hydrogenation, hydroboration, hydrosilylation, hydride reduction, hydroformylation, alkylation, allylic alkylation, arylation, alkenylation, epoxidation, hydrocyanation, disilylation, cyclization and isomerization reactions.The catalysts of the present invention provide the advantage of functioning in the presence of water without loss in enantioselectivity relative to the nonsulfonated BINAP catalyst in an organic solvent.Type: GrantFiled: September 28, 1995Date of Patent: October 27, 1998Assignee: California Institute of TechnologyInventors: Mark E. Davis, Kam To Wan
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Patent number: 5780674Abstract: Sulfonated phosphines of the formula ##STR1## in which R is cyclohexyl or alkyl having 1 to 4 carbon atoms, M is hydrogen, alkyl substituted ammonium, aryl substituted-ammonium, monovalent metal, or the chemical equivalent of a polyvalent metal, x is 1, 2, or 3 and n is 0 or 1. These compounds are obtained by sulfonation of the non-sulfonated parent substances with oleum or an anhydrous mixture of sulfuric acid and orthoboric acid.Type: GrantFiled: February 18, 1997Date of Patent: July 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Guido Albanese, Rainer Manetsberger, Wolfgang A. Herrmann
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Patent number: 5760286Abstract: Tertiary phosphine sulfonic acids are important ligands for transition metals where the complex is effective in catalyzing the oligomerization of alpha-olefins. An improved method of preparation utilizes inverse addition of lithiated aryl sulfonate salts to dihalophosphines at a rate which maintains a homogeneous reaction mixture, then alkylating the product of this reaction--a monohalo secondary phosphine sulfonate--with an organometallic compound, such as a Grignard reagent or an organolithium species.Type: GrantFiled: April 2, 1997Date of Patent: June 2, 1998Assignee: UOP LLCInventor: Timothy A. Brandvold
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Patent number: 5712396Abstract: .alpha.-Phosphonosulfonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.2 is OR.sup.5 or R.sup.5a ; R.sup.3 and R.sup.5 are independently H, alkyl, arylalkyl, aryl or cycloalkyl; R.sup.5a is H, alkyl, arylalkyl or aryl; R4 is H, alkyl, aryl, arylalkyl, or cycloalkyl;, Z is H, halogen, lower alkyl or lower alkenyl; and R.sup.1 is a lipophilic group which contains at least 7 carbons and is alkyl, alkenyl, alkynyl, mixed alkenyl-alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl; as further defined above; including pharmaceutically acceptable salts and or prodrug esters of the phosphonic (phosphinic) and/or sulfonic acids.Type: GrantFiled: July 5, 1994Date of Patent: January 27, 1998Inventors: David R. Magnin, Scott A. Biller, John K. Dickson, Jr., R. Michael Lawrence, Richard B. Sulsky
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Patent number: 5684181Abstract: The sulfonation of arylphosphines, which contain at least one aromatic radical which can be sulfonated, is carried out with an anhydrous mixture of sulfuric acid and orthoboric acid. By choosing the appropriate reaction temperature, the process allows selective introduction of the desired number of sulfonic acid radicals into the phosphine molecule and avoids the formation of phosphine oxides. When separating the sulfonation mixture, the orthoboric acid can be separated off together with the sulfuric acid.Type: GrantFiled: October 2, 1995Date of Patent: November 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Guido Albanese, Rainer Manetsberger, Wolfgang A. Herrmann, Christine Schwer
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Patent number: 5684182Abstract: The present invention relates to sulfonated diphosphines of the formula (I) ##STR1## where M is hydrogen, ammonium, a monovalent metal or the equivalent of a polyvalent metal, a, b, c and d are each 0 or 1, with the proviso that a+b+c+d is an integer from 1 to 4, Ar is an m-(MSO.sub.3)--C.sub.6 H.sub.4 radical and M is as defined above, n is 0, 1 or 2, Ph is a phenyl radical, R.sup.1 and R.sup.2 are identical or different and are each an alkyl radical having from 1 to 10 carbon atoms or a cycloaliphatic radical having from 5 to 10 carbon atoms in the ring, and a process for their preparation.Type: GrantFiled: February 21, 1996Date of Patent: November 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Christoph Naumann, Ahmed Tafesh, Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5663426Abstract: Sulfonated phosphines of the formula ##STR1## in which R is cyclohexyl or alkyl having 1 to 4 carbon atoms, M is hydrogen, alkyl substituted ammonium, aryl substituted-ammonium, monovalent metal, or the chemical equivalent of a polyvalent metal, x is 1, 2, or 3 and n is 0 or 1. These compounds are obtained by sulfonation of the non-sulfonated parent substances with oleum or an anhydrous mixture of sulfuric acid and orthoboric acid.Type: GrantFiled: October 2, 1995Date of Patent: September 2, 1997Assignee: Hoechst AktiengeschaftInventors: Guido Albanese, Rainer Manetsberger, Wolfgang A. Herrmann
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Patent number: 5637762Abstract: 5H-phenyl-3,13-disulfonatodibenzophosphole and a process for its preparation.Type: GrantFiled: October 2, 1995Date of Patent: June 10, 1997Assignee: Hoechst AktiengesellschaftInventors: Guido Albanese, Rainer Manetsberger, Wolfgang A. Herrmann, Rochus Schmid
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Patent number: 5631393Abstract: The invention relates to palladium compounds containing as ligands compounds of the formula (I) ##STR1## where Ar is C.sub.6 H.sub.4 SO.sub.3 M, M is hydrogen, ammonium, a monovalent metal or one equivalent of a polyvalent metal and Ph is the phenyl radical and n, m are zero, 1 or 2 and x, y, u, v are zero, 1 or 2.Type: GrantFiled: May 2, 1995Date of Patent: May 20, 1997Assignee: Hoechst AktiengesellschaftInventors: Christian Kohlpaintner, Matthias Beller
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Patent number: 5543571Abstract: A process for the asymmetric hydrogenation of N-acylhydrazones to optically active N-acylhydrazines in the presence of a chiral phospholane catalyst complex, a process for the reductive N--N bond cleavage of N-acylhydrazine to amines with samarium diiodide, and a multistep process for converting keto group-bearing compounds to the corresponding optically active amino group-bearing compounds are disclosed.Type: GrantFiled: March 7, 1995Date of Patent: August 6, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mark J. Burk
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Tetrasulfonated diphosphine compounds and metal complexes thereof for asymmetric catalytic reactions
Patent number: 5536858Abstract: The invention is concerned with novel water-soluble racemic or optically active compounds of formulae ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently signify lower alkyl or lower alkoxy;m and n are 0, 1 or 2; andX signifies hydrogen, an alkali :metal, the equivalent of an earthalkali metal or an ammonium ion;with the provision that R.sup.3 is in position 4 or 5 and R.sup.4 is in position 4' or 5'. The invention is also concerned with complexes of such compounds with a metal of Group VIII. These complexes are, useful as catalysts for asymmetric hydrogenation and for enantioselective hydrogen displacement in prochiral allylic systems.Type: GrantFiled: December 2, 1994Date of Patent: July 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Michel Lalonde, Rudolf Schmid -
Patent number: 5451698Abstract: The sulfonation of arylphosphines, i.e. mono-, di-, oligo- and polyphosphines, which contain at least one aromatic radical capable of being sulfonated, is carried out in the presence of a Lewis acid at 0.degree. to 80.degree. C. The process avoids side-reactions, in particular the formation of phosphine oxides. In treating the sulfonation mixture, the Lewis acid can be removed together with the sulfuric acid.Type: GrantFiled: June 23, 1994Date of Patent: September 19, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Wolfgang A. Herrmann, Rainer Manetsberger, Guido Albanese, Klaus Bergrath
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Patent number: 5347045Abstract: Sulfonated diphosphines of the formula ##STR1## in which Ar is m-C.sub.6 H.sub.4 --SO.sub.3 M, M is hydrogen, ammonium, a monovalent metal, or the chemical equivalent of a polyvalent metal; Ph is phenyl; the m's are individually 1 or 2, and the n's are individually 0, 1, or 2. A method of their preparation and the hydroformylation of olefins and olefinically unsaturated compounds using these compounds as a constituent of water-soluble catalyst systems are also disclosed.Type: GrantFiled: May 25, 1993Date of Patent: September 13, 1994Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Rainer Manetsberger, Helmut Bahrmann, Christian Kohlpaintner, Peter Lappe
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Patent number: 5274183Abstract: The preparation of water-soluble diphosphines derived from biaryl compounds by reaction with a solution of SO.sub.3 in sulfuric acid.Type: GrantFiled: September 23, 1992Date of Patent: December 28, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Herrman, Christian Kohlpaintner, Helmut Bahrmann
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Patent number: 5171892Abstract: This invention relates to novel chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.Type: GrantFiled: July 2, 1991Date of Patent: December 15, 1992Assignee: E. I. du Pont de Nemours and CompanyInventor: Mark J. Burk
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Patent number: 4965404Abstract: There is provided an industrial process for the advantageous preparation of high-purity lithium diphenylphosphinobenzene-m-monosulfonate.Type: GrantFiled: February 23, 1990Date of Patent: October 23, 1990Assignee: Kuraray Company, Ltd.Inventors: Toshihiko Maeda, Noriaki Yoshimura
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Patent number: 4895977Abstract: The removal of oxidizable organic impurities which include alkylthiolsulfonate from alkanesulfonic acids by treatment with an ozone containing gas is disclosed. The treated products have improved color and odor and exhibit improved long-term color stability.Type: GrantFiled: December 12, 1988Date of Patent: January 23, 1990Assignee: Pennwalt CorporationInventor: Martin Nosowitz
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Patent number: 4672013Abstract: Cyan dye-forming 6-hydroxy-2H-1,4-benzoxazin-3-(4H)-one couplers, preferably cyan dye-forming couplers corresponding to the general formula: ##STR1## wherein R represents hydrogen or R"'--X--NH, R' represents hydrogen or a substituted or unsubstituted alkyl group, R" represents hydrogen or R.sup.iv --X--, X represents a member selected from the group consisting of --CO--, --SO.sub.2 --, --OCOCO--, --NHCO--, R"' and R.sup.iv represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group and Y and Z, the same or different, represent hydrogen, halogen and a substituted or unsubstituted alkyl or alkoxy group,are described for use in silver halide color photographic processes and elements.Type: GrantFiled: April 28, 1986Date of Patent: June 9, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventor: Ivano Delprato