Patents by Inventor Marc Mauduit

Marc Mauduit 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: 9776178
    Abstract: The invention relates to a ruthenium alkylidene complex comprising a 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand, the cycloalkyl group of said 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand being a cyclic secondary aliphatic alkyl.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: October 3, 2017
    Assignees: Ecole Nationale Superieure De Chimie De Rennes, Centre National De La Recherche Scientifique CNRS
    Inventors: Marc Mauduit, Mathieu Rouen
  • Patent number: 9688641
    Abstract: The invention relates to a process for preparing an asymmetrical imidazolium salt of formula (1A), in which R1 is an aromatic group, R2 is chosen from a cyclic secondary aliphatic alkyl group and a heteroalkyl group, R3 and R4 are chosen, independently of one another, from the group consisting of hydrogen, a halide and an alkyl group, and A? is an anion. The process comprises a first substep of forming a reaction mixture by bringing one equivalent of an aniline into contact with one equivalent of a compound bearing an amine group, in the presence of at least four point five equivalents of a Brønsted acid. The process also comprises a second substep of forming a solution comprising one equivalent of a dicarbonyl, one equivalent of formaldehyde, and at least four point five equivalents of the Brønsted acid, and adding thereto the reaction mixture formed in the first substep. The mixture is left to stir for a predetermined time at a predetermined temperature.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: June 27, 2017
    Assignees: Ecole Nationale Superieure De Chimie De Rennes, Centre National De La Recherche Scientifique CNRS
    Inventors: Marc Mauduit, Olivier Basle, Mathieu Rouen
  • Patent number: 9556296
    Abstract: This invention describes a process for metathesis of olefins from feedstocks obtained from the Fischer-Tropsch process, using as catalyst a ruthenium alkylidene complex comprising a saturated or unsaturated, dissymmetrical N-heterocyclic carbene (NHC) ligand.
    Type: Grant
    Filed: April 25, 2014
    Date of Patent: January 31, 2017
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, IFP ENERGIES NOUVELLES, ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENNES
    Inventors: Helene Olivier-Bourbigou, Francois Hugues, Severine Forget, Mathieu Rouen, Marc Mauduit
  • Publication number: 20150329494
    Abstract: The invention relates to a process for preparing an asymmetrical imidazolium salt of formula (1A), in which R1 is an aromatic group, R2 is chosen from a cyclic secondary aliphatic alkyl group and a heteroalkyl group, R3 and R4 are chosen, independently of one another, from the group consisting of hydrogen, a halide and an alkyl group, and A? is an anion. The process comprises a fast substep of forming a reaction mixture by bringing one equivalent of an aniline into contact with one equivalent of a compound bearing an amine group, in the presence of at least four point five equivalents of a Brønsted acid. The process also comprises a second substep of forming a solution comprising one equivalent of a dicarbonyl, one equivalent of formaldehyde, and at least four point five equivalents of the Brønsted acid, and adding thereto the reaction mixture formed in the first substep. The mixture is left to stir for a predetermined time at a predetermined temperature.
    Type: Application
    Filed: December 11, 2013
    Publication date: November 19, 2015
    Applicant: Ecole National Superieure de Chimie de Rennes
    Inventors: Marc Mauduit, Olivier Basle, Mathieu Rouen
  • Publication number: 20150315223
    Abstract: The invention relates to a ruthenium alkylidene complex comprising a 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand, the cycloalkyl group of said 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand being a cyclic secondary aliphatic alkyl.
    Type: Application
    Filed: December 11, 2013
    Publication date: November 5, 2015
    Inventors: Marc Mauduit, Mathieu Rouen
  • Publication number: 20140323671
    Abstract: This invention describes a process for metathesis of olefins from feedstocks obtained from the Fischer-Tropsch process, using as catalyst a ruthenium alkylidene complex comprising a saturated or unsaturated, dissymmetrical N-heterocyclic carbene (NHC) ligand.
    Type: Application
    Filed: April 25, 2014
    Publication date: October 30, 2014
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, IFP ENERGIES NOUVELLES, ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENNES
    Inventors: Helene OLIVIER-BOURBIGOU, Francois HUGUES, Severine FORGET, Mathieu ROUEN, Marc MAUDUIT
  • Patent number: 8835628
    Abstract: The present invention relates to catalytically active compounds of the general formula (1) that are highly tunable, as well as to a method of their preparation and their use in any type metathesis reaction. The new compounds of the present invention comprise activation sites that allow for specific catalyst design. Particularly, side chains and ligands allow efficient activity and specificity control of the catalysts of the present invention.
    Type: Grant
    Filed: July 30, 2010
    Date of Patent: September 16, 2014
    Assignees: Ecole Nationale Superieure de Chimie de Rennes, Centre National de la Recherche Scientifique CNRS
    Inventors: Marc Mauduit, Frédéric Caijo, Christophe Crevisy
  • Patent number: 8586757
    Abstract: Disclosed herein are compounds of the formula (I) or (II) in which: L is a neutral ligand; X, X? are anionic ligands; R1 and R2 are, separately, a hydrogen, a C1-C6 alkyl, a C1-C6 perhalogenoalkyl, a aldehyde, a ketone, an ester, a nitrile, an aryl, a pyridinium alkyl, an optionally substituted C5 or C6 pyridinium alkyl, perhalogenoalkyl or cyclohexyl, a Cnh2NY radical 10 with n between 1 and 6 and y an iconic marker, or a radical having the formula: wherein R1 can be a radical of formula (Ibis) when the compound has formula (I) or of formula (IIbis) when the compound has formula (II), R3 is a C1-C6 alkyl, or a C5 or C6 cycloalkyl or a C5 or C6 aryl; R0, R4, R5, R6, R7, R8, R9, R10, R11, are, separately, a hydrogen, C1-C6 alkyl, a C1-C6 perhalogenoalkyl, or a C5 or C6 aryl; wherein R9, R10, R11 can be a heterocycle; X1 is anion. R1 and R2 can form, with the N and the C to which they are attached, a heterocycle.
    Type: Grant
    Filed: February 13, 2013
    Date of Patent: November 19, 2013
    Assignee: Umicore AG & Co. KG
    Inventors: Marc Mauduit, Isabelle Laurent, Hervé Clavier
  • Publication number: 20130197218
    Abstract: The present invention relates to catalytically active compounds of the general formula (1) that are highly tunable, as well as to a method of their preparation and their use in any type metathesis reaction. The new compounds of the present invention comprise activation sites that allow for specific catalyst design. Particularly, side chains and ligands allow efficient activity and specificity control of the catalysts of the present invention.
    Type: Application
    Filed: July 30, 2010
    Publication date: August 1, 2013
    Inventors: Marc Mauduit, Frédéric Caijo, Christophe Crevisy
  • Publication number: 20130190518
    Abstract: The present invention relates to a process for preparing a terpenoid derivative, the process comprising a metathesis of an olefin and a terpenoid, and to terpenoid derivatives prepared with said process.
    Type: Application
    Filed: July 11, 2011
    Publication date: July 25, 2013
    Applicant: Ecole Nationale Superieure de Chimie de Rennes
    Inventors: Marc Mauduit, Frédéric Caijo, Christophe Crévisy
  • Patent number: 8394965
    Abstract: The invention relates to all compounds of the formula (I) or (II) in which: L is a neutral ligand; X, X? are anionic ligands; R1 and R2 are, separately, a hydrogen, a C1-C6 alkyl, a C1-C6 perhalogenoalkyl, a aldehyde, a ketone, an ester, a nitrile, an aryl, a pyridinium alkyl, an optionally substituted C5 or C6 pyridinium alkyl, perhalogenoalkyl or cyclohexyl, a Cnh2NY radical 10 with n between 1 and 6 and y an i8onic marker, or a radical having the formula: wherein R1 can be a radical of formula (Ibis) when the compound has formula (I) or of formula (IIbis) when the compound has formula (II), R3 is a C1-C6 alkyl, or a C5 or C6 cycloalkyl or a C5 or C6 aryl; R0, R4, R5, R6, R7, R8, R9, R10, R11, are, separately, a hydrogen, C1-C6 alkyl, a C1-C6 perhalogenoalkyl, or a C5 or C6 aryl; wherein R9, R10, R11 can be a heterocycle; X1 is anion. R1 and R2 can form, with the N and the C to which they are attached, a heterocycle.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: March 12, 2013
    Assignee: Umicore AG & Co. KG
    Inventors: Marc Mauduit, Isabelle Laurent, Hervé Clavier
  • Patent number: 8299250
    Abstract: The invention relates to a compound of the formula (I) or the formula (II) in which: W is an oxygen atom or a radical of the formula NH; X is hydrogen or an alkaline cation or a C1-C8 alkyl or a —(CH2)n3—C(R4)(R5)(R6) radical; X and R on the one hand and X and R1 on the other hand may independently form an optionally substituted cycle with 5, 6 or 7 links. The invention also relates to complexes of said compounds with at least one metal selected from the group comprising copper, palladium, ruthenium, iridium and rhodium, and to a method for the synthesis of these compounds. These compounds and complexes can be used in various asymmetrical catalysis methods.
    Type: Grant
    Filed: October 17, 2008
    Date of Patent: October 30, 2012
    Assignees: Ecole Nationale Supérieure de Chimie de Rennes, CNRS (Centre National de la Recherche Scientifique)
    Inventors: Marc Mauduit, Diane Rix, Christophe Crevisy, Joanna Wencel
  • Publication number: 20100267956
    Abstract: The invention relates to a compound of the formula (I) or the formula (II) in which: W is an oxygen atom or a radical of the formula NH; X is hydrogen or an alkaline cation or a C1-C8 alkyl or a —(CH2)n3—C(R4)(R5)(R6) radical; X and R on the one hand and X and R1 on the other hand may independently form an optionally substituted cycle with 5, 6 or 7 links. The invention also relates to complexes of said compounds with at least one metal selected from the group comprising copper, palladium, ruthenium, iridium and rhodium, and to a method for the synthesis of these compounds. These compounds and complexes can be used in various asymmetrical catalysis methods.
    Type: Application
    Filed: October 17, 2008
    Publication date: October 21, 2010
    Inventors: Marc Mauduit, Diane Rix, Christophe Crevisy, Joanna Wencel
  • Publication number: 20100087644
    Abstract: The invention relates to all compounds of the formula (I) or (II) in which: L is a neutral ligand; X, X? are anionic ligands; R1 and R2 are, separately, a hydrogen, a C1-C6 alkyl, a C1-C6 perhalogenoalkyl, a aldehyde, a ketone, an ester, a nitrile, an aryl, a pyridinium alkyl, an optionally substituted C5 or C6 pyridinium alkyl, perhalogenoalkyl or cyclohexyl, a Cnh2NY radical 10 with n between 1 and 6 and y an i8onic marker, or a radical having the formula: wherein R1 can be a radical of formula (Ibis) when the compound has formula (I) or of formula (IIbis) when the compound has formula (II), R3 is a C1-C6 alkyl, or a C5 or C6 cycloalkyl or a C5 or C6 aryl; R0, R4, R5, R6, R7, R8, R9, R10, R11, are, separately, a hydrogen, C1-C6 alkyl, a C1-C6 perhalogenoalkyl, or a C5 or C6 aryl; wherein R9, R10, R11 can be a heterocycle; X1 is anion. R1 and R2 can form, with the N and the C to which they are attached, a heterocycle.
    Type: Application
    Filed: November 30, 2007
    Publication date: April 8, 2010
    Applicants: ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENNES, CNRS (CENTRE NATIONAL DE LA RECHERCHE SCIENTFIQUE)
    Inventors: Marc Mauduit, Isabelle Laurent, Hervé Clavier
  • Patent number: 7390926
    Abstract: The invention provides the diastereoselective alkylation of optically active nopinone to form the compound of formula (I) according to scheme A below: in which: —R is a C5-15 alkyl group; —R1 is especially a C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl group or a C5-15 aryl, each group optionally being substituted; and —X is a halogen atom; and the configuration of the compound of formula (I) is either (E) or (Z) or a mixture of the two. The compound of formula (I) is a valuable synthetic intermediate.
    Type: Grant
    Filed: July 12, 2006
    Date of Patent: June 24, 2008
    Assignee: ZaCh System
    Inventors: Jean-Claude Caille, Marc Mauduit
  • Publication number: 20070225516
    Abstract: The invention provides the diastereoselective alkylation of optically active nopinone to form the compound of formula (I) according to scheme A below: in which: R is a C5-15 alkyl group; R1 is especially a C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl group or a C5-15 aryl, each group optionally being substituted; and X is a halogen atom; and the configuration of the compound of formula (I) is either (E) or (Z) or a mixture of the two. The compound of formula (I) is a valuable synthetic intermediate.
    Type: Application
    Filed: July 12, 2006
    Publication date: September 27, 2007
    Applicant: PPG-SIPSY
    Inventors: Jean-Claude Caille, Marc Mauduit