Patents by Inventor François Metz

François Metz has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 11613465
    Abstract: The invention relates to a method for producing a fluorine- and sulphur-bearing compound of formula F—SO—R (I) or F—SO2—R (II), comprising the reaction, in the presence of water, of at least one salt providing a fluoride anion and at least one halgoenosulfoxide compound of formula X—SO—R? (I0) from a halogenosulfonyl compound of formula X—SO2—R? (II0), in which X is a halogen atom other than fluorine and R and R? are each a group linked by a covalent bond to the sulphur atom, said bond linking the sulphur atom with a nitrogen atom. The invention also relates to a method for producing salts of a fluorine- and sulphur-bearing compound of formula F—SO—R (I) or F—SO2—R (II) which are advantageously used as electrolyte salts, as precursors of antistatic agents or as surfactant precursors.
    Type: Grant
    Filed: December 3, 2014
    Date of Patent: March 28, 2023
    Assignee: RHODIA OPERATIONS
    Inventors: Olivier Buisine, François Metz
  • Patent number: 10511068
    Abstract: The present invention relates to a process for recovering a metal salt of an electrolyte dissolved in a matrix, said process consisting in subjecting the electrolyte to a liquid extraction with water.
    Type: Grant
    Filed: June 16, 2015
    Date of Patent: December 17, 2019
    Assignee: RHODIA OPERATIONS
    Inventor: François Metz
  • Publication number: 20180037543
    Abstract: The invention relates to a method for producing an oxysulphidic and fluorinated derivative in the form of a salt of formula (II) Ea-SO?Q+ (II) comprising providing an ionic liquid compound of formula (I) in the liquid state Ea-SOO?Cr (II)—Ea representing the fluorine atom or a group having between 1 and 10 carbon atoms selected from fluoroalkyls, perfluoroalkyls and fluoroalkenyls; and—Q+ representing an onium cation, with a sulphur oxide, said ionic liquid compound of formula (I) representing at least 50 wt. % of the initial liquid reactive medium.
    Type: Application
    Filed: December 7, 2015
    Publication date: February 8, 2018
    Inventor: François METZ
  • Publication number: 20180022694
    Abstract: The present disclosure relates to the preparation of a compound of formula (I) comprising an —SO2F function, R—SO2F, by reacting a compound of formula (II), R?—SO2X, with a fluorinating agent, the process carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst, wherein R, R?, and X are described herein.
    Type: Application
    Filed: August 14, 2017
    Publication date: January 25, 2018
    Inventor: François METZ
  • Patent number: 9873666
    Abstract: The invention concerns a method for preparing an oxysulphide and fluorinated derivative, said method comprising the reacting, in the presence of an organic solvent, of: i) at least one compound of formula Ea-COOR (I), in which Ea represents the fluorine atom or a group having 1 to 10 carbon atoms chosen from fluoroalkyls, perfluoroalkyls and fluoroalkenyls and R represents hydrogen, a monovalent cation or an alkyl group, and ii) a sulphur oxide, said method being such that the initial molar ratio (sulphur oxide/compound of formula (I)) is less than 0.4 and the concentration of sulphur oxide dissolved in the reaction medium is kept constant for the entire duration of the reaction to a value of between 0.2% and 3% by weight by means of continually adding said sulphur oxide to the reaction medium.
    Type: Grant
    Filed: September 11, 2014
    Date of Patent: January 23, 2018
    Assignee: RHODIA OPERATIONS
    Inventors: Denis Revelant, François Metz, Valery Dambrin, Marie Chauve
  • Patent number: 9765021
    Abstract: The preparation is described of a compound of formula (I) comprising an —SO2F function by reacting a compound of formula (II) with a fluorinating agent selected from hydrofluoric acid and an ionic fluoride of a monovalent or divalent cation: R—SO2F??(I) R?—SO2X??(II) where R is selected from the groups R1, R2 and R3: R1=—CnHaFb with n=1-10, a+b=2n+1, b?1; R2=—CxHyFz—SO2F with x=1-10, y+z=2x and z?1; R3=?-CcHhFf with c=1-10; h+f=2c and f?1; where R? is selected from the following groups R?1, R?2 and R?3: R?1=—CnHaXb with n=1-10, a+b=2n+1, b?1; R?2=—CxHyXz—SO2X with x=1-10, y+z=2x and z?1; R?3=?-CcHhXf with c=1-10; h+f=2c and f?1; ? denoting a phenyl group; X?Cl, Br.
    Type: Grant
    Filed: July 3, 2014
    Date of Patent: September 19, 2017
    Assignee: RHODIA OPERATIONS
    Inventor: François Metz
  • Publication number: 20170110769
    Abstract: The present invention relates to a process for recovering a metal salt of an electrolyte dissolved in a matrix, said process consisting in subjecting the electrolyte to a liquid extraction with water.
    Type: Application
    Filed: June 16, 2015
    Publication date: April 20, 2017
    Inventor: François METZ
  • Publication number: 20160368866
    Abstract: The preparation is described of a compound of formula (I) comprising an —SO2F function by reacting a compound of formula (II) with a fluorinating agent selected from hydrofluoric acid and an ionic fluoride of a monovalent or divalent cation: R-SO2F ??(I) R?-SO2X ??(II) where R is selected from the groups R1, R2 and R3: R1=—CnHaFb with n=1-10, a+b=2n+1, b?1; R2=—CxHyFz—SO2F with x=1-10, y+z=2x and z?1; R3=?-CcHhFf with c=1-10; h+f=2c and f?1; where R? is selected from the following groups R?1, R?2 and R?3: R?1=—CnHaXb with n=1-10, a+b=2n+1, b?1; R?2=—CxHyXz-SO2X with x=1-10, y+z=2x and z?1; R?3=?-CcHhXf with c=1-10; h+f=2c and f?1; ? denoting a phenyl group; X=Cl, Br.
    Type: Application
    Filed: July 3, 2014
    Publication date: December 22, 2016
    Inventor: François METZ
  • Publication number: 20160304347
    Abstract: The invention relates to a method for producing a fluorine- and sulphur-bearing compound of formula F—SO—R (I) or F—SO2—R (II), comprising the reaction, in the presence of water, of at least one salt providing a fluoride anion and at least one halgoenosulfoxide compound of formula X—SO—R? (I0) from a halogenosulfonyl compound of formula X—SO2—R? (II0), in which X is a halogen atom other than fluorine and R and R? are each a group linked by a covalent bond to the sulphur atom, said bond linking the sulphur atom with a nitrogen atom. The invention also relates to a method for producing salts of a fluorine- and sulphur-bearing compound of formula F—SO—R (I) or F—SO2—R (II) which are advantageously used as electrolyte salts, as precursors of antistatic agents or as surfactant precursors.
    Type: Application
    Filed: December 3, 2014
    Publication date: October 20, 2016
    Inventors: Olivier BUISINE, François METZ
  • Publication number: 20160221939
    Abstract: The invention concerns a method for preparing an oxysulphide and fluorinated derivative, said method comprising the reacting, in the presence of an organic solvent, of: i) at least one compound of formula Ea-COOR (I), in which Ea represents the fluorine atom or a group having 1 to 10 carbon atoms chosen from fluoroalkyls, perfluoroalkyls and fluoroalkenyls and R represents hydrogen, a monovalent cation or an alkyl group, and ii) a sulphur oxide, said method being such that the initial molar ratio (sulphur oxide/compound of formula (I)) is less than 0.4 and the concentration of sulphur oxide dissolved in the reaction medium is kept constant for the entire duration of the reaction to a value of between 0.2% and 3% by weight by means of continually adding said sulphur oxide to the reaction medium.
    Type: Application
    Filed: September 11, 2014
    Publication date: August 4, 2016
    Inventors: Denis REVELANT, François METZ, Valery DAMBRIN, Marie CHAUVE
  • Patent number: 9394247
    Abstract: The present invention relates to a method for preparing an aqueous sulfonimide compound of the formula (Rf1—SO2)(Rf2—SO2)NH, wherein Rf1 and Rf2 are independently selected from the group comprising: a fluorine atom and groups having 1 to 10 carbon atoms selected from the perfluoroalkyl, fluoroalkyl, fluoroalkenyl and fluoroallyl groups, from a mixture M1 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO2H and/or Rf2SO2H, Rf1SO2NH2 and/or Rf2SO2NH2, characterized in that said method includes an oxidation step of said mixture M1 using an oxidizing agent in order to obtain a mixture M2 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO3H and/or Rf2SO3H and Rf1SO2NH2and/or Rf2SO2NH2.
    Type: Grant
    Filed: July 11, 2013
    Date of Patent: July 19, 2016
    Assignee: RHODIA OPERATIONS
    Inventors: Bernard Besson, Francois Metz, Olivier Buisine
  • Publication number: 20150203449
    Abstract: The present invention relates to a method for preparing an aqueous sulfonimide compound of the formula (Rf1—SO2) (Rf2—SO2)NH, wherein Rf1et Rf2 are independently selected from the group comprising: a fluorine atom and groups having 1 to 10 carbon atoms selected from the perfluoroalkyl, fluoroalkyl, fluoroalkenyl and fluoroallyl groups, from a mixture M1 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO2H and/or Rf2SO2H, Rf1SO2NH2 and/or Rf2SO2NH2, characterized in that said method includes an oxidation step of said mixture M1 using an oxidizing agent in order to obtain a mixture M2 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO3H and/or Rf2SO3H, and Rf1SO2NH2 and/or Rf2SO2NH2.
    Type: Application
    Filed: July 11, 2013
    Publication date: July 23, 2015
    Inventors: Bernard Besson, Francois Metz, Olivier Buisine
  • Patent number: 8933274
    Abstract: A method for preparing a compound of formula (I) which is a vanillin derivative, of dimer type, called 3-(4-hydroxy-3-methoxybenzyl)-4-hydroxy-5-methoxybenzaldehyde, such method comprising a reaction of vanillin and vanillyl alcohol in the presence of a base.
    Type: Grant
    Filed: October 5, 2012
    Date of Patent: January 13, 2015
    Assignee: Rhodia Operations
    Inventors: Laurent Garel, Martine Vibert, Corine Cochennec, François Metz
  • Publication number: 20140323769
    Abstract: A method for preparing a compound of formula (I) which is a vanillin derivative, of dimer type, called 3-(4-hydroxy-3-methoxybenzyl)-4-hydroxy-5-methoxybenzaldehyde, such method comprising a reaction of vanillin and vanillyl alcohol in the presence of a base.
    Type: Application
    Filed: October 5, 2012
    Publication date: October 30, 2014
    Applicant: RHODIA OPERATIONS
    Inventors: Laurent Garel, Martine Vibert, Corine Cochennec, François Metz
  • Patent number: 8829236
    Abstract: The present invention relates to a method for preparing a halogenoacetyl fluoride and the derivatives thereof. The inventive method for preparing a halogenoacetyl fluoride acid is characterized in that said method includes: a step of preparing a halogenoacetyl halide by photo-oxidation of a halogenoethylene compound in conditions such that the transformation rate of the halogenoethylene compound into halogenoacetyl halide is no higher than 80%, producing a reaction mixture essentially including halogenoacetyl halide and the excess halogenoethylene compound; a step of partial fluorination of the mixture obtained by reacting the latter with hydrofluoric acid suitable for obtaining a mixture of halogenoacetyl fluoride and the excess halogenoethylene compound; a step of separating the halogenoacetyl fluoride and the excess halogenoethylene compound. The invention can be used, specifically, for preparing the trichloroacetyl fluoride used as an intermediate species in the production of trifluoroacetic acid.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: September 9, 2014
    Assignee: Rhodia Operations
    Inventors: Laurent Saint-Jalmes, Francois Metz
  • Patent number: 8633336
    Abstract: The subject of the present invention is a method for separating a carboxylic acid in salified form bearing at least one halogen atom at the ? position of the carbonyl group from a medium comprising it.
    Type: Grant
    Filed: July 8, 2009
    Date of Patent: January 21, 2014
    Assignee: Rhodia Operations
    Inventors: Olivier Buisine, François Metz
  • Patent number: 8633334
    Abstract: The present invention relates to a method for preparing a highly pure trifluoromethanesulphinic acid. The method of the invention for preparing a highly pure trifluoromethanesulphinic acid, starting from an aqueous mixture comprising a trifluoromethanesulphinic acid salt, a trifluoroacetic acid salt and saline impurities resulting from the method for preparing same, is characterized in that said mixture is subjected to the following operations: —acidification such that the trifluoroacetic acid salt and the triflinic acid salt are released in an acid form, —separation of the trifluoroacetic acid and trifluoromethanesulphinic acid by distillation enabling the trifluoroacetic acid to be recovered at the top of the distillation and the trifluoromethanesulphinic acid to be recovered at the bottom of the distillation, —separation by distillation of the trifluoromethanesulphinic acid present in the distillation residue previously obtained.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: January 21, 2014
    Assignee: Rhodia Operations
    Inventors: Vincent Schanen, Olivier Buisine, François Metz, Bernard Besson
  • Patent number: 8471059
    Abstract: The present invention relates to a method for preparing a salt of trifluoromethanesulphinic acid termed “triflinic acid”. More specifically, the invention relates to a method for preparing a highly pure triflinic acid salt.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: June 25, 2013
    Assignee: Rhodia Operations
    Inventors: Vincent Schanen, Olivier Buisine, François Metz, Bernard Besson
  • Patent number: 8399709
    Abstract: The subject of the present invention is a method for the sulphonylation of a hydroxylated organic compound. The invention relates more particularly to a method for the trifluoromethanesulphonylation of a hydroxylated organic compound. The invention is especially intended for perfluorinated aliphatic hydroxylated compounds. The method of the invention for the sulphonylation of a hydroxylated organic compound is characterized in that it comprises reacting said compound with a sulphonylation agent in an organic medium and in the presence of a heterogeneous inorganic base.
    Type: Grant
    Filed: May 28, 2009
    Date of Patent: March 19, 2013
    Assignee: Rhodia Operations
    Inventor: François Metz
  • Patent number: 8299300
    Abstract: The invention relates to a method for preparing difluoroacetic acid and the salts thereof. The invention also relates to the preparation of difluoroacetyl fluoride used as an intermediate product in the preparation of difluoroacetic acid. The method for preparing difluoroacetic acid according to the invention is characterized in that the same comprises the step of preparing difluoroacetyl fluoride by reacting dichloroacetyl chloride with hydrofluoric acid in a gaseous phase and in the presence of a chromium-based catalyst, followed by the step of hydrolysing the difluoroacetyl fluoride thus obtained.
    Type: Grant
    Filed: March 9, 2009
    Date of Patent: October 30, 2012
    Assignee: Rhodia Operations
    Inventors: François Metz, Laurent Saint-Jalmes