And -c(=x)- Containing Reactant, Wherein X Is Chalcogen Patents (Class 558/108)
  • Publication number: 20130345463
    Abstract: The present invention provides a process for preparing a highly pure form of malathion having a reduced level of toxic impurities. In addition, the malathion prepared by the process of this invention is storage stable. The level of toxic impurities in the malathion, e.g., isomalathion, O,O,S-trimethyl phosphorodithioate (MeOOSPS), O,O,S-trimethyl phosphorothioate (MeOOSPO), O,S,S-trimethyl phosphorodithioate (MeOSSPO), malaoxon, isomalathion, diethyl fumarate, methyl malathion, dimethyl malathion, O,O-methyl,ethyl-S-(1,2-dicarboethoxy)ethyl-phosphorodithioate are lower than that of any other commercial preparation of malathion that may be used for pharmaceutical purposes.
    Type: Application
    Filed: August 29, 2013
    Publication date: December 26, 2013
    Applicant: Taro Pharmaceuticals North America, Inc.
    Inventors: Daniella Gutman, Wael Baidussi
  • Publication number: 20130109819
    Abstract: The invention relates to a mono-substituted phosphinic acid and to the use thereof as a regulator in radical polymerization. Such regulators do not result in the formation of poorly soluble salts, and in addition, the polymers produced with the regulators according to the invention are characterized by a uniform polymerization degree having a narrow size distribution. In addition, the invention relates to a method for producing such mono-substituted phosphinic acids.
    Type: Application
    Filed: July 19, 2011
    Publication date: May 2, 2013
    Applicant: SIKA TECHNOLOGY AG
    Inventors: Ueli Sulser, Lukas Frunz, Jörg Zimmermann
  • Patent number: 8293938
    Abstract: The invention relates to alkylphosphonous acids, salts and esters of formula (I) A-P(?O)(OX)—H (I) wherein A is C2-C20alkyl, C2-C20alkylene, and C8-C20 alkaryl are optionally substituted, and X is H, alkyl, aryl, alkylaryl, alkenyl, substituted alkyl, aryl, alkaryl, alkenyl, ammonium, primary, secondary, tertiary, quaternary alkyl and/or aryl ammonium, an alkali metal, an alkaline earth metal, a metal of the third and fourth main group and the second, fourth and eight sub-group or a metal of the lanthanoid group. The invention also relates to methods for producing same and to the uses of said compounds.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: October 23, 2012
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Harald Bauer, Werner Krause
  • Publication number: 20120225020
    Abstract: This disclosure provides choline analogs comprising the following structure: where each R1 independently is H or isotopically enriched D, R2 is a protecting group, and N is 14N or isotopically enriched 15N. This disclosure also provides methods of making choline analogs, which include performing a protection step on a betaine aldehyde to form a choline analog, and methods of using choline analogs to form hyperpolarized compounds.
    Type: Application
    Filed: February 24, 2012
    Publication date: September 6, 2012
    Inventors: Eduard Y. Chekmenev, Roman V. Shchepin
  • Publication number: 20110251315
    Abstract: The invention relates to a method for producing monofunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester thereof, whereupon said alkylphosphonous acid, the salt or ester (II) thereof is reacted with compounds containing C?C, C?O, or C?N double bonds to obtain compounds of type (III), wherein R1, R2, R3, R4, R5, R6 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, X represents, inter alia, H, C1-C18-alkyl, C6-C18-aryl, and/or Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, and wherein A represents OH, NH2, NHR, NR2, or O—CO—R8, and W represents a mineral acid, carboxylic acid, Lewis acid, or organic acid, wherein n is a whole or a fractional number from 0 to 4, and catalyst A represents transition metals and/or transition metal compo
    Type: Application
    Filed: October 6, 2009
    Publication date: October 13, 2011
    Applicant: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
  • Publication number: 20110237720
    Abstract: The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof by means of vinyl compounds, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with carbon monoxide to yield a mono-carboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C, wherein R1, R2, R3, R4, R5, R6 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X and Y are the same or different and stand indepe
    Type: Application
    Filed: October 6, 2009
    Publication date: September 29, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110213059
    Abstract: The invention relates to a method for producing mono-carboxyfunctional zed dialkylphosphinic acids and esters and salts thereof by means of vinylenes/nitriles, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with a hydrogen cyanide source to yield a mono-functionalized dialkylphosphinic acid derivative (VII) in the presence of a catalyst C, and d) the thus obtained monofunctionalized dialkylphosphinic acid derivative (VII); is reacted to yield a monocarboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst D, wherein R1, R2, R3, R4, R5
    Type: Application
    Filed: October 6, 2009
    Publication date: September 1, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20090124822
    Abstract: The present invention provides a process for preparing a highly pure form of malathion having a reduced level of toxic impurities. In addition, the malathion prepared by the process of this invention is storage stable. The level of toxic impurities in the malathion, e.g., isomalathion, O,O,S-trimethyl phosphorodithioate (MeOOSPS), O,O,S-trimethyl phosphorothioate (MeOOSPO), O,S,S-trimethyl phosphorodithioate (MeOSSPO), malaoxon, isomalathion, diethyl fumarate, methyl malathion, dimethyl malathion, O,O-methyl,ethyl-S-(1,2-dicarboethoxy)ethyl-phosphorodithioate are lower than that of any other commercial preparation of malathion that may be used for pharmaceutical purposes.
    Type: Application
    Filed: January 14, 2009
    Publication date: May 14, 2009
    Applicant: Taro Pharmaceuticals North America, Inc.
    Inventors: Daniella Gutman, Wael Baidussi
  • Patent number: 6864218
    Abstract: A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.
    Type: Grant
    Filed: July 9, 2002
    Date of Patent: March 8, 2005
    Assignee: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 6441223
    Abstract: A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: August 27, 2002
    Assignee: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 6191253
    Abstract: A dispersant for aqueous mill-bases obtainable by reacting a polyethylene glycol with a molar excess of a hydroxycarboxylic acid containing from 4 to 17 carbon atoms or lactone thereof and/or with a C3-4-alkylene oxide to form a polymeric diol and phosphating the diol. The preferred hydroxycarboxylic acid or lactone is &egr;-caprolactone.
    Type: Grant
    Filed: June 9, 1998
    Date of Patent: February 20, 2001
    Assignee: Zeneca Limited
    Inventors: John David Schofield, Dean Thetford
  • Patent number: 6090967
    Abstract: The present invention relates to a process for preparing phosphonous esters which comprisesa) reacting elemental yellow phosphorus with alkyl halides in the presence of alkali metal hydroxides and/or alkaline earth metal hydroxides to form a mixture which comprises, as main components, the alkali metal salts and/or alkaline earth metal salts of the alkylphosphonous, phosphorous and hypophosphorous acids,b) removing the alkylphosphonous acid from the mixture obtained by a)c) esterifying the alkylphosphonous acid.The invention likewise relates to the use of the phosphonous esters prepared by this process.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: July 18, 2000
    Assignee: Clariant GmbH
    Inventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
  • Patent number: 6090968
    Abstract: The present invention relates to a process for preparing phosphinic esters which comprisesa) reacting elemental yellow phosphorus with alkyl halides in the presence of alkali metal hydroxide or alkaline earth metal hydroxide to form a mixture which comprises as main constituents the alkali metal salts and/or alkaline earth metal salts of alkylphosphonous acid, phosphorous acid and hypophosphorous acidb) removing the alkylphosphonous acid from the mixture obtained as described in a),c) esterifying the alkylphosphonous acid,d) adding the resultant ester of the alkylphosphonous acid to a compound having at least one C.dbd.C double bond.The invention likewise relates to the use of the phosphinic esters prepared by this process inter alia as flame retardants and as precursor for further syntheses.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: July 18, 2000
    Assignee: Clariant GmbH
    Inventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
  • Patent number: 5785894
    Abstract: A dispersant for aqueous mill-bases obtainable by reacting a polyethylene glycol with a molar excess of a hydroxycarboxylic acid containing from 4 to 17 carbon atoms or lactone thereof and/or with a C.sub.3-4 -alkylene oxide to form a polymeric diol and phosphating the diol. The preferred hydroxycarboxylic acid or lactone is .epsilon.-caprolactone.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: July 28, 1998
    Assignee: Zeneca Limited
    Inventors: John David Schofield, Dean Thetford
  • Patent number: 5783690
    Abstract: A 2-N-amidoethyl protected nucleoside analog phosphoramidite of formula (1): ##STR1## is useful in the synthesis of a wide variety of oligonucleotide analogs. Coupling yields with phosphoramidite (1) in solution or solid phase oligonucleotide analog synthesis are high and the 2-N-amidoethyl protecting group can be removed easily under standard conditions.
    Type: Grant
    Filed: September 18, 1997
    Date of Patent: July 21, 1998
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Zacharia S. Cheruvallath, Daniel C. Capaldi, Vasulinga T. Ravikumar, Douglas L. Cole
  • Patent number: 5362899
    Abstract: A stereospecific method of preparing alpha-aminophosphonic acids and derivatives thereof is provided. A protected amino acid is converted to a acyl aroyl or diacyl peroxide which spontaneously rearranges to form an alpha-amino ester. This rearrangement occurs stereospecifically with retention of configuration. The ester is subsequently converted to an appropriate leaving group and displaced with a phosphite yielding a chiral alpha-aminophosphonic acid or derivative.Alpha-aminophosphonic acids are useful for the synthesis of peptide analogs that possess a phosphonate linkage in the place of an amide linkage. This substitution can impart protease resistance in therapeutic peptides thereby increasing the serum half-life.
    Type: Grant
    Filed: September 9, 1993
    Date of Patent: November 8, 1994
    Assignee: Affymax Technologies, N.V.
    Inventor: David A. Campbell
  • Patent number: 5359115
    Abstract: Phosphonate esters can be synthesized in high yields by condensations of alcohols with methyl phosphonates followed by selective demethylation. The reaction is general, relatively insensitive to steric constraints of hindered phosphonic acids, and can also be carried out on a solid support to synthesize large collections of compounds to screen for pharmacological activity.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: October 25, 1994
    Assignee: Affymax Technologies, N.V.
    Inventors: David A. Campbell, Jeffrey W. Jacobs
  • Patent number: 5348670
    Abstract: Lubricant additives are disclosed which are produced by reacting an alkanolamine, a carboxylic acid and phosphorous acid. The reaction product may also include a boron compound and/or a monofunctional alcohol. The additives are useful in combination with metalworking oils, particularly in extreme pressure applications, to replace currently used chlorinated paraffin additives.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: September 20, 1994
    Assignee: The Elco Corporation
    Inventors: Randolph A. McDonald, Gerald D. Burt
  • Patent number: 5334741
    Abstract: Solid substrates with free hydroxyl groups are phosphorylated by thermolysing a solution of phosphoramidate of the formula ##STR1## in the presence of the substrate, whereby metaphosphate is generated which phosphorylates the substrate.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: August 2, 1994
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis D. Quin, Stefan Jankowski
  • Patent number: 5117043
    Abstract: The invention relates to an N-sulfomethylglycinate of formula:HO.sub.3 S--CH.sub.2 --NH--CH.sub.2 --COOR.sub.1 (I)COOR.sub.1 being a hydrolysable carboxylic ester group.It also relates to a process for the preparation of the compound of formula (I) consisting in putting in contact sulfur dioxide, formaldehyde, and glycine in the presence of a R.sub.1 OH alcohol, or glycinate.It also relates to the use of the compound of formula (I) for the preparation of herbicides of the glyphosate type of reaction with a phosphite or a phosphonate of formula (R.sub.2 O).sub.2 P(O) H in which (R.sub.2 O).sub.2 P is a hydrolysable phosphonic ester group, then optionally by a subsequent hydrolysis reaction.
    Type: Grant
    Filed: August 1, 1989
    Date of Patent: May 26, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Bernard Botannet, Jean-Louis Clavel, Jean-Pierre Corbet, Michel Mulhauser
  • Patent number: 5115005
    Abstract: Compounds of the formula Ia or Ib ##STR1## in which R.sub.1 and R.sub.2, independently of one another, are hydrogen, alkyl, cycloalkyl, alkenyl, aryl or aralkyl or, together with the carbon atoms in the .alpha.-position to the carbonyl groups, form a cyclopentane, cyclopentene, cyclohexane, cyclohexene, cyclohexadiene or bicyclo[2.2.1]hept-5-ene ring which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, or form a monocyclic or polycyclic, aromatic ring system which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, R.sub.3 and R.sub.4, independently of one another, are hydrogen, alkyl, alkenyl, aryl or aralkyl, and R.sub.5 and R.sub.6, independently of one another, are alkyl, aryl or aralkyl groups, are highly suitable as flame retardants for polymers.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: May 19, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Peter Horner
  • Patent number: 5099324
    Abstract: An area to be monitored is picked up by a TV camera, and data of the picked-up image is converted into digital data in units of frames and stored in frame memories. The image data stored in the frame memories are read out, and a change region is extracted as an image of a moving object. The extracted moving object image has a plurality of dispersed regions including a shadow image. Only the dispersed regions corresponding to the moving object are extracted by setting a frame, and a noise image including the shadow image is removed.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: March 24, 1992
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Shozo Abe