Patents by Inventor Gerard Hillion

Gerard Hillion 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: 8419810
    Abstract: A process for producing biofuels by transforming triglycerides into at least two families of biofuels, monoesters of fatty acids and soluble ethers and/or acetals of glycerol, comprises: at least one transesterification step in which said triglyceride is reacted by heterogeneous catalysis with at least one primary monoalcohol selected from methanol and ethanol to produce at least one methyl and/or ethyl ester of the fatty acids of the starting triglycerides and glycerol, said products being free of by-products; and an etherification step in which the glycerol is reacted with at least one olefinic hydrocarbon containing 4 to 12 carbon atoms; and/or an acetalization step in which the glycerol is reacted with at least one compound selected from aldehydes, ketones and acetals derived from aldehydes or ketones.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: April 16, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Gerard Hillion, Bruno Delfort, Isabelle Durand
  • Patent number: 7906663
    Abstract: In order to produce both an olefinic fraction and a composition of diacids or diesters of fats, a process is carried out which comprises, in succession: a) metathesis of an unsaturated fat with ethylene in the presence of at least one non-aqueous ionic liquid; b) separating and recycling the ionic liquid used in the first step; c) separating, by distillation, the olefinic fraction (fraction A) from the unsaturated fat mono-ester or mono-basic acid fraction (fraction B) formed in step a); d) homometathesis of the mono-unsaturated fat ester or acid cut (fraction B) which allows the co-production of unsaturated fat diesters or diacids (fraction C) and ethylene which is recycled to the first methathesis step of the process; and e) optionally, recycling the ionic liquid containing the catalyst used in step d).
    Type: Grant
    Filed: January 23, 2007
    Date of Patent: March 15, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Hélène Olivier-Bourbigou, Christophe Vallee, Gérard Hillion
  • Patent number: 7851643
    Abstract: A method of manufacturing an ester composition comprising ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms from a vegetable or an animal oil, neutral or acid, virgin or recycled, the method comprising: a stage 1 of reaction of vegetable or animal oil with methanol, in the presence of a heterogeneous catalyst comprising a combination of at least one metallic oxide and alumina or a combination of at least two metallic oxides and possibly alumina, and a stage 2 of reaction of the product from stage 1 with ethanol in the presence of a heterogeneous catalyst as defined for stage 1, so as to obtain from vegetable or animal oils, a mixture of fatty acid esters rich in fatty acid ethyl esters and a glycerin of high purity.
    Type: Grant
    Filed: September 15, 2006
    Date of Patent: December 14, 2010
    Assignee: IFP Energies Nouvelles
    Inventors: Gérard Hillion, Bruno Delfort
  • Patent number: 7754904
    Abstract: A process is described in which an unsaturated fat is reacted in a homometathesis reaction in the presence of at least one non-aqueous ionic liquid to produce both an olefinic fraction and a composition of monoalcohol diesters or diacids. Particular application to a mixture of esters of an oleic sunflower seed oil or an oleic rapeseed oil, the process producing both an olefinic fraction and a composition of monoalcohol diesters or diacids wherein, in general, more than half of its chains is constituted by unsaturated C18 chains.
    Type: Grant
    Filed: January 23, 2007
    Date of Patent: July 13, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Hélène Olivier-Bourbigou, Gérard Hillion, Christophe Vallee
  • Patent number: 7678932
    Abstract: A process is described in which an unsaturated fat is reacted with ethylene in a metathesis reaction in the presence of at least one non-aqueous ionic liquid to produce both an olefinic fraction and a composition of monoalcohol or polyol esters. Particular application to an oleic sunflower seed oil, an oleic rapeseed oil or to a mixture of monoalcohol esters of said oils, the process producing both an olefinic fraction and a monoalcohol or glycerol esters composition generally having more than half of its chains constituted by unsaturated C10 chains.
    Type: Grant
    Filed: November 25, 2005
    Date of Patent: March 16, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Cyril Thurier, Helene Olivier-Bourbigou, Pierre Dixneuf, Gerard Hillion
  • Patent number: 7652156
    Abstract: A method allowing, from natural fat or oils, vegetable or animal, or from other glyceride mixtures, to obtain in a quasi-quantitative way fatty acid ethyl esters that can be used as gas oil substitutes, comprises the succession of stages as follows: a stage (a) wherein the oil, the fat or the glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction, a stage (b) wherein the glycerin formed is decanted and removed, without requiring an excess ethanol evaporation operation, a stage (c) wherein a second transesterification reaction is carried out so as to obtain a product whose ester content is at least 97% by mass, a stage (d) wherein controlled neutralization of the catalyst is carried out, a stage (e) wherein the excess ethanol is removed by distillation, a stage (f) wherein the ester undergoes purification by means of water wash sequences, and a stage (g) wherein the ester mixture is dried under reduced pressure.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: January 26, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Gérard Hillion, Bruno Delfort
  • Patent number: 7612245
    Abstract: A process for the selective hydrogenation of diolefinic compounds to mono-olefinic compounds uses a catalyst composition comprising at least one salt of a transition metal from groups IB, IIB, VB, VIB, VIIB and VIII of the periodic table, at least one ligand and at least one organometallic reducing agent, optionally in the presence of a non-aqueous ionic liquid selected from the group formed by liquid salts with general formula Q+A? (in which Q+ represents a quaternary ammonium and/or quaternary phosphonium and A? represents any anion which can form a liquid salt below 90° C.).
    Type: Grant
    Filed: June 16, 2003
    Date of Patent: November 3, 2009
    Assignee: Institut Francais du Petrole
    Inventors: Gerard Hillion, Laurent Savary, David Proriol, Christophe Gautreau, Denis Uzio, Helene Olivier-Bourbigou
  • Patent number: 7592470
    Abstract: A novel process is described for producing esters of linear monocarboxylic acids containing 6 to 26 carbon atoms, by reacting vegetable or animal oils, neutral or otherwise, with monoalcohols containing 1 to 18 carbon atoms in the presence of a catalyst selected from: mixtures of titanium oxide and alumina having formula: (TiOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y, representing the weight ratio of the two oxides, has a value of 0.005 to 0.995; mixtures of zirconium oxide and alumina having formula: (ZrOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y has a value of 0.005 to 0.995; and mixtures of antimony oxide and alumina having formula: (SbOx)y(Al2O3)1-y where x has the value 1.2 to 2.6 and y has a value of 0.005 to 0.995, in order to directly produce, in one or more steps, an ester for use as a fuel and a pure glycerin.
    Type: Grant
    Filed: May 26, 2004
    Date of Patent: September 22, 2009
    Assignee: Institut Francais du Petrole
    Inventors: Thierry Lacome, Gerard Hillion, Bruno Delfort, Renaud Revel, Serge Leporq, Gustave Acakpo
  • Patent number: 7566794
    Abstract: A method allowing, from natural fat or oils, or from other glyceride mixtures, to obtain fatty acid ethyl esters that can be used as gas oil substitutes, comprises: stage (a) oil, fat or a glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction; stage (b) resultant glycerin is decanted and removed, without requiring an excess ethanol evaporation operation, stage (c) a second transesterification is conducted to obtain a product whose ester content is at least 97% by mass, stage (d) evaporation of excess ethanol is carried out in the presence of the catalyst under suitable conditions preventing a reverse transesterification reaction, the resultant ethanol being practically anhydrous, stage (e) the ester undergoes purification by water wash sequences, and stage (f) the ester is dried under reduced pressure.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: July 28, 2009
    Assignee: Institut Francais du Petrole
    Inventors: Gérard Hillion, Bruno Delfort
  • Patent number: 7420073
    Abstract: A process that employs a heterogeneous catalyst comprising a zinc aluminate mixed oxide and having the following formula: ZnAl2O4, xZnO, yAl2O3 in which x and y each represent a number in the range 0 to 2, and in which the zinc aluminate is more particularly of the spinel type, makes it possible, by means of C1 to C5 monoalcohols, to: transesterify vegetable or animal oils having a natural free acidity, such as unrefined degummed rapeseed, soya, sunflower oils or exotic oils of the African oil, palm nut oil or coconut oil type, which are naturally rich in fatty acids; and simultaneously esterify their free acidity; so as to use phospholipid free and/or degummed unrefined acid oil with an acid number in the range 0.5 to 20, for example 1 to 15 and preferably 2 to 12, to produce esters, for example methyl esters, for use as fuels.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: September 2, 2008
    Assignee: Institut Francais du Petrole
    Inventors: Gérard Hillion, Dominique Le Pennec
  • Publication number: 20070283619
    Abstract: A process for producing biofuels by transforming triglycerides into at least two families of biofuels, monoesters of fatty acids and soluble ethers and/or acetals of glycerol, comprises: at least one transesterification step in which said triglyceride is reacted by heterogeneous catalysis with at least one primary monoalcohol selected from methanol and ethanol to produce at least one methyl and/or ethyl ester of the fatty acids of the starting triglycerides and glycerol, said products being free of by-products; and an etherification step in which the glycerol is reacted with at least one olefinic hydrocarbon containing 4 to 12 carbon atoms; and/or an acetalization step in which the glycerol is reacted with at least one compound selected from aldehydes, ketones and acetals derived from aldehydes or ketones.
    Type: Application
    Filed: January 27, 2005
    Publication date: December 13, 2007
    Inventors: Gerard Hillion, Bruno Delfort, Isabelle Durand
  • Publication number: 20070179302
    Abstract: A process is described in which an unsaturated fat is reacted in a homometathesis reaction in the presence of at least one non-aqueous ionic liquid to produce both an olefinic fraction and a composition of monoalcohol diesters or diacids. Particular application to a mixture of esters of an oleic sunflower seed oil or an oleic rapeseed oil, the process producing both an olefinic fraction and a composition of monoalcohol diesters or diacids wherein, in general, more than half of its chains is constituted by unsaturated C18 chains.
    Type: Application
    Filed: January 23, 2007
    Publication date: August 2, 2007
    Inventors: Helene Olivier-Bourbigou, Gerard Hillion, Christophe Vallee
  • Publication number: 20070179307
    Abstract: In order to produce both an olefinic fraction and a composition of diacids or diesters of fats, a process is carried out which comprises, in succession: a) metathesis of an unsaturated fat with ethylene in the presence of at least one non-aqueous ionic liquid; b) separating and recycling the ionic liquid used in the first step; c) separating, by distillation, the olefinic fraction (fraction A) from the unsaturated fat mono-ester or mono-basic acid fraction (fraction B) formed in step a); d) homometathesis of the mono-unsaturated fat ester or acid cut (fraction B) which allows the co-production of unsaturated fat diesters or diacids (fraction C) and ethylene which is recycled to the first methathesis step of the process; and e) optionally, recycling the ionic liquid containing the catalyst used in step d).
    Type: Application
    Filed: January 23, 2007
    Publication date: August 2, 2007
    Inventors: Helene Olivier-Bourbigou, Christophe Vallee, Gerard Hillion
  • Publication number: 20070112212
    Abstract: A method allowing, from natural fat or oils, vegetable or animal, or from other glyceride mixtures, to obtain in a quasi-quantitative way fatty acid ethyl esters that can be used as gas oil substitutes, comprises the succession of stages as follows: a stage (a) wherein the oil, the fat or the glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction, a stage (b) wherein the glycerin formed is decanted and removed, without requiring an excess ethanol evaporation operation, a stage (c) wherein a second transesterification reaction is carried out so as to obtain a product whose ester content is at least 97% by mass, a stage (d) wherein controlled neutralization of the catalyst is carried out, a stage (e) wherein the excess ethanol is removed by distillation, a stage (f) wherein the ester undergoes purification by means of water wash sequences, and a stage (g) wherein the ester mixture is dried under reduced pressure.
    Type: Application
    Filed: September 20, 2006
    Publication date: May 17, 2007
    Inventors: Gerard Hillion, Bruno Delfort
  • Publication number: 20070073070
    Abstract: A method allowing, from natural fat or oils, vegetable or animal, or from other glyceride mixtures, to obtain in a quasi-quantitative way fatty acid ethyl esters that can be used as gas oil substitutes, comprises the succession of stages as follows: a stage (a) wherein the oil, the fat or the glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction, a stage (b) wherein the glycerin formed is decanted and removed, without requiring an excess ethanol evaporation operation, a stage (c) wherein a second transesterification reaction is carried out so as to obtain a product whose ester content is at least 97% by mass, a stage (d) wherein evaporation of the excess ethanol is carried out in the presence of the catalyst under suitable conditions preventing a reverse transesterification reaction, the ethanol being obtained practically anhydrous (it can be recycled in the process without requiring rectification), a stage (e) wherein the, ester underg
    Type: Application
    Filed: September 20, 2006
    Publication date: March 29, 2007
    Inventors: Gerard Hillion, Bruno Delfort
  • Publication number: 20070066838
    Abstract: Method of manufacturing an ester composition comprising ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms from a vegetable or an animal oil, neutral or acid, virgin or recycled, said method being characterized in that it comprises: a stage 1 of reaction of said vegetable or animal oil with methanol, in the presence of a heterogeneous catalyst comprising a combination of at least one metallic oxide and alumina or a combination of at least two metallic oxides and possibly alumina, and a stage 2 of reaction of the product from stage 1 with ethanol in the presence of a heterogeneous catalyst defined in the same manner as the heterogeneous catalyst used in stage 1, allowing to obtain from vegetable or animal oils, in an economical way, a mixture of fatty acid esters rich in fatty acid ethyl esters and a glycerin of high purity.
    Type: Application
    Filed: September 15, 2006
    Publication date: March 22, 2007
    Inventors: Gerard Hillion, Bruno Delfort
  • Patent number: 7151187
    Abstract: A new process for the production of linear monocarboxylic acid esters with 6 to 26 carbon atoms, by reaction of vegetable oils or animal oils that may or may not be neutral, with monoalcohols of 1 to 18 carbon atoms, uses a catalyst that is selected from among: the combinations of zinc oxides and titanium oxides; the combinations of zinc oxide, titanium oxide and alumina; the combinations of bismuth and titanium oxides; and the combinations of bismuth oxide, titanium oxide and alumina. The process makes it possible to produce directly, in one or more stages, an ester that can be used as a fuel and a pure glycerin.
    Type: Grant
    Filed: May 2, 2005
    Date of Patent: December 19, 2006
    Inventors: Bruno Delfort, Gérard Hillion, Dominique Le Pennec, Christophe Lendresse
  • Publication number: 20060129010
    Abstract: A process for the selective hydrogenation of diolefinic compounds to mono-olefinic compounds uses a catalyst composition comprising at least one salt of a transition metal from groups IB, IIB, VB, VIB, VIIB and VIII of the periodic table, at least one ligand and at least one organometallic reducing agent, optionally in the presence of a non-aqueous ionic liquid selected from the group formed by liquid salts with general formula Q+A? (in which Q+ represents a quaternary ammonium and/or quaternary phosphonium and A? represents any anion which can form a liquid salt below 90° C.).
    Type: Application
    Filed: June 16, 2003
    Publication date: June 15, 2006
    Applicant: INSTITUTE FRANCAIS DU PETROLE
    Inventors: Gerard Hillion, Laurent Savary, David Proriol, Christophe Gautreau, Denis Uzio, Helene Olivier-Bourbigou
  • Publication number: 20050266139
    Abstract: A novel process is described for producing esters of linear monocarboxylic acids containing 6 to 26 carbon atoms, by reacting vegetable or animal oils, neutral or otherwise, with monoalcohols containing 1 to 18 carbon atoms in the presence of a catalyst selected from: mixtures of titanium oxide and alumina having formula: (TiOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y, representing the weight ratio of the two oxides, has a value of 0.005 to 0.995; mixtures of zirconium oxide and alumina having formula: (ZrOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y has a value of 0.005 to 0.995; and mixtures of antimony oxide and alumina having formula: (SbOx)y(Al2O3)1-y where x has the value 1.2 to 2.6 and y has a value of 0.005 to 0.995, in order to directly produce, in one or more steps, an ester for use as a fuel and a pure glycerin.
    Type: Application
    Filed: May 26, 2004
    Publication date: December 1, 2005
    Inventors: Thierry Lacome, Gerard Hillion, Bruno Delfort, Renaud Revel, Serge Leporq, Gustave Acakpo
  • Publication number: 20050261509
    Abstract: A new process for the production of linear monocarboxylic acid esters with 6 to 26 carbon atoms, by reaction of vegetable oils or animal oils that may or may not be neutral, with monoalcohols of 1 to 18 carbon atoms, uses a catalyst that is selected from among: the combinations of zinc oxides and titanium oxides; the combinations of zinc oxide, titanium oxide and alumina; the combinations of bismuth and titanium oxides; and the combinations of bismuth oxide, titanium oxide and alumina. The process makes it possible to produce directly, in one or more stages, an ester that can be used as a fuel and a pure glycerin.
    Type: Application
    Filed: May 2, 2005
    Publication date: November 24, 2005
    Inventors: Bruno Delfort, Gerard Hillion, Dominique Le Pennec, Christophe Lendresse