Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/861)
  • Patent number: 8809596
    Abstract: The present invention relates to a process for preparing deodorized 1,2-propanediol, to the use of the purified propanediol and to an apparatus for performing the process.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: August 19, 2014
    Assignee: BASF SE
    Inventors: Stephan Maurer, Roman Prochazka, Oliver Bey, Jochen Steiner, Jochem Henkelmann, Gerhard Theis, Peter Wahl, Frank Heimann
  • Patent number: 8809593
    Abstract: The present invention relates to a process for the preparation of the hydroxyacetone or 1,2 propylene glycol. More particularly, the present invention relates to a process for preparation of hydroxyacetone or 1,2 propylene glycol by glycerol. Further, the said process is catalyzed by metal catalysts that results in 80 to 100% selectivity towards conversion of glycerol to hydroxyacetone (acetol) or 1,2 propylene glycol (1,2 PG).
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: August 19, 2014
    Assignee: Council of Scientific and Industrial Research
    Inventors: Chandrasshekhar Vasant Rode, Amol Mahalingappa Hengne, Ajay Ashok Ghalwadkar, Rasika Bharat Mane, Pravinkumar Hansraj Mohite, Hari Shankar Potdar
  • Patent number: 8759594
    Abstract: The present invention relates to a process for hydrogenating oligo- and/or polyesters obtainable by esterifying a DCS with a diol or diol mixture, said hydrogenation being performed in the presence of a catalyst whose catalyst precursor comprises copper oxide, aluminum oxide and at least one oxide of lanthanum, of iron, of tungsten, of molybdenum, of titanium or of zirconium, and to a process for preparing 1,6-hexanediol by catalytically hydrogenating ester mixtures which comprise, as main components, oligo- and polyesters of adipic acid and 6-hydroxycaproic acid, and are obtained by esterifying DCS with diols, especially 1,6-hexanediol or diol mixtures.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: June 24, 2014
    Assignee: BASF SE
    Inventors: Olivier Abillard, Rolf Pinkos, Gerd-Dieter Tebben, Tilman Sirch, Daniel Urbanczyk, Heiko Urtel, Rolf Tompers
  • Patent number: 8754263
    Abstract: Disclosed are methods for generating propylene glycol, ethylene glycol and other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols from biomass using hydrogen produced from the biomass. The methods involve reacting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and then reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycol and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production of oxygenated hydrocarbons without the need for hydrogen from an external source.
    Type: Grant
    Filed: June 25, 2013
    Date of Patent: June 17, 2014
    Assignee: Virent, Inc.
    Inventor: Randy D. Cortright
  • Patent number: 8754266
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Grant
    Filed: May 10, 2013
    Date of Patent: June 17, 2014
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Patent number: 8742180
    Abstract: Embodiments of the present disclosure include methods of effecting process control in a reaction system for the production of 1,4-butanediol, the method including determining at least one property of a sample from the reaction system using Raman spectroscopy, and adjusting at least one parameter of the reaction system in response to the at least one determined property. Embodiments may also include methods of producing 1,4-butanediol, the method including reacting allyl alcohol with carbon monoxide and hydrogen in the presence of a solvent and a catalyst to produce a reactor fluid, sampling the reaction, determining at least one property of the sample using Raman spectroscopy, and adjusting the reaction in response to the at least one determined property.
    Type: Grant
    Filed: November 13, 2012
    Date of Patent: June 3, 2014
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Brian A. Salisbury, Jenny M. Oran Osment
  • Patent number: 8735635
    Abstract: This invention is a process for making 1,2-propane diol from glycerol. The process comprises subjecting a glycerol stream to hydrogenation conditions in the presence of a transition metal promoted skeletal copper catalyst to enhance selective production of 1,2-propane diol product. Chromium promoted catalyst is preferred for this invention, and moreover, it is preferred that the skeletal copper catalyst is prepared from copper aluminum alloys that have been subjected to leaching conditions selected to achieve at least 40% leaching of aluminum from the alloy. This process is particularly conducive to conducting the hydrogenation with reactant mixture in the liquid phase. The catalysts used in this invention are particularly suitable for use in a fixed catalyst bed, but can be activated and sized so that the catalyst is also suitable for use in slurry based reactions.
    Type: Grant
    Filed: February 23, 2010
    Date of Patent: May 27, 2014
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Stephen Raymond Schmidt
  • Publication number: 20140135511
    Abstract: The present invention relates to a method for producing a hydride having a carbon number of 4, comprising contacting, in liquid phase, an unsaturated compound having a carbon number of 4 as a raw material with a solid catalyst obtained by loading a metal element belonging to Groups 9 to 11 of the long periodic table on a support, thereby performing hydrogenation to produce a corresponding hydride having a carbon number of 4, wherein hydrogenation is performed in the presence of, as a solvent, a 1,4-butanediol having a nitrogen component concentration of 1 ppm by weight to 1 wt % in terms of nitrogen atom.
    Type: Application
    Filed: January 22, 2014
    Publication date: May 15, 2014
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Yusuke IZAWA, Masaru UTSUNOMIYA, Norikazu KONISHI, Kouta TANAKA
  • Publication number: 20140121419
    Abstract: Digestion of cellulosic biomass solids may be complicated by release of lignin therefrom. Methods for digesting cellulosic biomass solids may comprise: providing cellulosic biomass solids in a digestion solvent; at least partially converting the cellulosic biomass solids into a phenolics liquid phase comprising lignin, an aqueous phase comprising an alcoholic component derived from the cellulosic biomass solids, and an optional light organics phase; combining at least the phenolics liquid phase and the aqueous phase with one another, thereby forming a combined phase; and separating at least a portion of the alcoholic component from at least a portion of the combined phase.
    Type: Application
    Filed: October 30, 2013
    Publication date: May 1, 2014
    Applicant: SHELL OIL COMPANY
    Inventors: Joseph Broun POWELL, Kimberly Ann JOHNSON, Glenn Charles KOMPLIN, Edward James DENTON
  • Patent number: 8692032
    Abstract: Tungsten carbide catalysts are used in preparation of ethylene glycol by hydrogenating degradation of cellulose. The catalyst includes tungsten carbide as main catalytic active component, added with small amount of one or more transition metals such as nickel, cobalt, iron, ruthenium, rhodium, palladium, osmium, iridium, platinum, and copper as the second metal, supported on one or more porous complex supports such as active carbon, alumina, silica, titanium dioxide, silicon carbide, zirconium oxide, for conversion of cellulose to ethylene glycol. The catalyst realizes high efficiency, high selectivity, and high yield in the conversion of cellulose to ethylene glycol at the temperature of 120-300° C., hydrogen pressure of 1-10 MPa, and hydrothermal conditions. Compared to the existing industrial synthetic method of ethylene glycol using ethylene as feedstock, the invention has the advantages of using renewable raw material resources, environment friendly process, and excellent atom economy.
    Type: Grant
    Filed: June 29, 2012
    Date of Patent: April 8, 2014
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Tao Zhang, Na Ji, Mingyuan Zheng, Aiqin Wang, Yuying Shu, Xiaodong Wang, Jingguang Chen
  • Publication number: 20140087978
    Abstract: A method of converting an inactive biocide into an active biocide comprises: contacting the inactive biocide with an activating agent, wherein the activating agent is capable of chemically reacting with the inactive biocide; and causing or allowing a chemical reaction to take place between the inactive biocide and the activating agent, wherein the chemical reaction produces the active biocide. The methods can also include deactivating the active biocide via a chemical reaction between the active biocide and a deactivating agent.
    Type: Application
    Filed: September 27, 2012
    Publication date: March 27, 2014
    Applicant: HALLIBURTON ENERGY SERVICES, INC
    Inventor: Jay P. DEVILLE
  • Publication number: 20140058138
    Abstract: Methods and systems are provided for converting methane in a feed stream to butanediol. The method includes processing acetylene as an intermediate stream to form a hydrocarbon stream including butanediol. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of carbon monoxide to prevent undesired reactions in downstream processing units.
    Type: Application
    Filed: June 11, 2013
    Publication date: February 27, 2014
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
  • Patent number: 8648005
    Abstract: The present invention provides a method of preparing the copper-containing hydrogenation catalyst having high activity by liquid phase reduction without decreasing purity of the solvent and a method for efficiently producing an alcohol. The present invention provides the method of preparing the copper-containing hydrogenation catalyst, including reducing a molded precursor of the copper-containing hydrogenation catalyst by supplying hydrogen gas or a mixture of hydrogen gas with an inert gas at a temperature of 50 to 150° C. in the presence of a solvent to obtain the copper-containing hydrogenation catalyst, wherein the reduction is conducted at an average reduction velocity of the copper-containing hydrogenation catalyst of not more than 3.0% by weight/hour.
    Type: Grant
    Filed: September 10, 2009
    Date of Patent: February 11, 2014
    Assignee: Kao Corporation
    Inventors: Toru Sakamoto, Shoji Hasegawa
  • Patent number: 8642813
    Abstract: The present invention provides methods, reactor systems, and catalysts for converting in a continuous process biomass to less complex oxygenated compounds for use in downstream processes to produce biofuels and chemicals. The invention includes methods of converting the components of biomass, such as hemicellulose, cellulose and lignin, to water-soluble materials, including lignocellulosic derivatives, cellulosic derivatives, hemicellulosic derivatives, carbohydrates, starches, polysaccharides, disaccharides, monosaccharides, sugars, sugar alcohols, alditols, polyols, diols, alcohols, ketones, cyclic ethers, esters, carboxylic acids, aldehydes, and mixtures thereof, using hydrogen and a heterogeneous liquefaction catalyst.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: February 4, 2014
    Assignee: Virent, Inc.
    Inventors: Ming Qiao, Randy D. Cortright, John Kania, Elizabeth Woods
  • Publication number: 20140005444
    Abstract: Digesting cellulosic biomass solids in the presence of a well-distributed slurry catalyst capable of activating molecular hydrogen may limit the amount of degradation products that form during digestion.
    Type: Application
    Filed: June 27, 2013
    Publication date: January 2, 2014
    Inventors: Glenn Charles KOMPLIN, Joseph Broun POWELL
  • Publication number: 20140005445
    Abstract: Digesting cellulosic biomass in the presence of a slurry catalyst may reduce degradation product formation, but catalyst distribution and retention can be problematic. Digestion methods can comprise: providing cellulosic biomass solids and a slurry catalyst capable of activating molecular hydrogen in a digestion unit; providing a digestible filter aid in the digestion unit; distributing the slurry catalyst within the cellulosic biomass solids using fluid flow; retaining at least a portion of the slurry catalyst in a fixed location using the digestible filter aid; heating the cellulosic biomass solids in the presence of the slurry catalyst, a digestion solvent, and molecular hydrogen, thereby forming a liquor phase comprising soluble carbohydrates; and performing a catalytic reduction reaction on the soluble carbohydrates within the digestion unit, thereby at least partially forming a reaction product comprising a triol, a diol, a monohydric alcohol, or any combination thereof in the digestion unit.
    Type: Application
    Filed: June 27, 2013
    Publication date: January 2, 2014
    Inventors: Glenn Charles KOMPLIN, Joseph Broun KOMPLIN
  • Patent number: 8603938
    Abstract: The present invention provides the method for preparing a catalyst including the following steps 1 and 2, and the method for producing an alcohol including preparing a catalyst by the method and subjecting a carboxylic acid or a carboxylic acid ester to catalytic reduction with hydrogen in the presence of the prepared catalyst: step 1: immersing a molded precursor of a catalyst containing metal oxide in a solvent, step 2: supplying hydrogen gas or a mixture of hydrogen gas with an inert gas to a catalyst layer in the presence of a solvent to reduce the catalyst precursor prepared in the step 1.
    Type: Grant
    Filed: September 10, 2009
    Date of Patent: December 10, 2013
    Assignee: Kao Corporation
    Inventors: Toru Sakamoto, Taku Mimura
  • Publication number: 20130310613
    Abstract: An integrated process for producing paraffins and polyols from renewable feedstocks has been developed in which a hydrolysis process is integrated with the hydroprocessing step, producing products suitable for use as transportation fuels. Integration allows the use of common equipment which minimizes cost, raw material consumption, and energy requirements.
    Type: Application
    Filed: May 18, 2012
    Publication date: November 21, 2013
    Applicant: UOP LLC
    Inventor: Tom N. Kalnes
  • Patent number: 8580119
    Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.
    Type: Grant
    Filed: November 27, 2012
    Date of Patent: November 12, 2013
    Assignee: Menlo Energy Management, LLC
    Inventors: Gaurav Shah, Sunil Suri
  • Publication number: 20130289311
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Cu, a Cu oxide, or mixtures thereof; a heteropoly acid component comprising H3[P(W3O10)4], H4[Si(W3O10)4], H4[P(Mo3O10)4], H4[Si(Mo3O10)4], Cs2.5H0.5[P(W3O10)4], Cs2.5H0.5[Si(W3O10)4], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Mn, a Mn oxide, Fe, an Fe oxide, Co, a Co oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, or a Zn oxide, Ag, a Ag oxide, SiO2, or Al2O3; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support.
    Type: Application
    Filed: April 25, 2013
    Publication date: October 31, 2013
    Inventors: ALAN MARTIN ALLGEIER, WATHUDURA INDIKA NAMAL DE SILVA, CARL MENNING, JOSEPH E. MURPHY, JOACHIM C. RITTER, SOURAV KUMAR SENGUPTA
  • Publication number: 20130289319
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising a first metal component comprising Ni, Ir, Pt, Rh, Ru, Pd, Fe, Ag, or Au; a heteropoly acid component comprising H3[P(W3O10)4], H4[Si(W3O10)4], H4[P(Mo3O10)4], H4[Si(Mo3O10)4], Cs2.5H0.5[P(W3O10)4]Cs2.5H0.5[Si(W3O10)4], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Fe, a Fe oxide, Co, a Co oxide, Mn, a Mn oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, a Zn oxide, SiO2, or Al2O3; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support.
    Type: Application
    Filed: April 25, 2013
    Publication date: October 31, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joachim C. Ritter, Sourav Kumar Sengupta
  • Publication number: 20130289318
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Pt, Cu, Ni, Pd, Pt, Rh, Ir, Ru, or Fe on a WO3 or WOx support. In one embodiment, the process comprises contacting the feedstock with hydrogen in the presence of a catalyst comprising a metal M1 and a metal M2 or an oxide of M2, and optionally a support. In one embodiment, M1 is Pd, Pt, or Ir; and M2 is Mo, W, V, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ge, Sn, Ti, Au, or Co. The Cn oxygenate may be obtained from a biorenewable resource.
    Type: Application
    Filed: April 25, 2013
    Publication date: October 31, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Alan Martin ALLGEIER, Torren Ryan CARLSON, Wathudura Indika Namal DE SILVA, Ekaterini KOROVESSI, Carl MENNING, Joachim C. RITTER, H David ROSENFELD, Sourav Kumar SENGUPTA
  • Publication number: 20130289312
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In some embodiments, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising metals M1, M2, and M3 and optionally a support, wherein: M1 is Mn, Cr, V, or Ti; M2 is Ni, Co, or Fe; and M3 is Cu, Ag, Pt, Pd or Au; or M1 is Pt or Rh; M2 is Cu, Ni or Pd; and M3 is Mo, Re or W. The Cn oxygenate may be obtained from a biorenewable resource.
    Type: Application
    Filed: April 25, 2013
    Publication date: October 31, 2013
    Applicant: E I DU PONT DE MEMOURS AND COMPANY
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joachim C. Ritter, Sourav Kumar Sengupta
  • Patent number: 8563783
    Abstract: This invention relates generally to a process for value-added processing of fats and oils to yield glycerol and glycerol derivatives. More particularly, the process converts glycerol to acetol and then acetol to propylene glycol to produce a propylene glycol with ultra-low amounts of ethylene glycol. The propylene glycol thus produced may be used as an antifreeze, deicing compound, or anti-icing compound.
    Type: Grant
    Filed: August 27, 2012
    Date of Patent: October 22, 2013
    Assignee: The Curators of the University of Missouri
    Inventor: Galen J. Suppes
  • Publication number: 20130253231
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Application
    Filed: May 10, 2013
    Publication date: September 26, 2013
    Applicant: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Publication number: 20130253230
    Abstract: A process for making ethylene glycol by feeding reactants including 1,2-dioxygenated organic compounds, an organometallic homogeneous catalyst, and hydrogen to a hydrogenation reactor, reacting at least a portion of the reactants with hydrogen in the presence of the organometallic homogeneous catalyst to produce a reaction product mixture containing ethylene glycol, and passivating the catalyst by contacting the catalyst with a carbon monoxide to thereby suppress the formation of by-product diols other thatn the ethylene glycol primary product, and suppress the formation of by-product tetrols and by-product glycolaldehyde acetals; and separating at least a portion of the ethylene glycol from the reaction product mixture.
    Type: Application
    Filed: March 23, 2012
    Publication date: September 26, 2013
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: David William Norman, Jonathan Michael Penney, Peter Borden Mackenzie
  • Publication number: 20130225874
    Abstract: The invention relates to a method for manufacturing a sorbitol syrup having a total reducing sugar content no higher than 0.2% and mannitol content of less than 1%, with 70 wt % of dry matter. Said manufacturing method is characterized in that it includes the steps of: (a) hydrolyzing a solution of sucrose in a solution of invert sugars, (b) separating the solution of invert sugar by simulated moving bed chromatography into, on the one hand, a dextrose syrup having at least 99.3%, preferably 99.4%, more preferably at least 99.5%, and even more preferably 99.7% of dextrose content and, on the other hand, a fructose syrup having at least 90%, preferably 92% of fructose content, and (c) hydrogenating said dextrose syrup into a sorbitol syrup having a reducing sugar content no higher than 0.2% and a mannitol content of less than 1%, with 70 wt % of dry matter.
    Type: Application
    Filed: April 8, 2013
    Publication date: August 29, 2013
    Applicant: ROQUETTE FRERES
    Inventor: ROQUETTE FRERES
  • Publication number: 20130217923
    Abstract: The present invention relates to novel structured catalysts based on sintered metal fibers (SMF) coated by a basic oxide layer with Pd-nanoparticles, to reactions of organic compounds with hydrogen in the presence of said catalyst and an organic base as well as to vitamins, carotinoids, perfume ingredients, and/or food or feed ingredients prepared by using this reaction.
    Type: Application
    Filed: July 1, 2011
    Publication date: August 22, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Lioubov Kiwi-Minsker, Igor Iouranov
  • Patent number: 8501987
    Abstract: Process for producing glycolic acid by contacting carbon monoxide and formaldehyde, optionally in the presence of a solvent, with a catalyst including a solid acid. The solid acid is an acidic polyoxometalate compound insoluble in formaldehyde, glycolic acid and the optional solvent, and has a concentration of acid sites of greater than 60 ?mol g?1 on the external surface and/or a Hammett Acidity value of less than ?12.8.
    Type: Grant
    Filed: March 16, 2009
    Date of Patent: August 6, 2013
    Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences BP P.L.C.
    Inventors: Ying Sun, Hua Wang, Zhongmin Liu, Martin Philip Atkins
  • Patent number: 8501664
    Abstract: A process for treating a carrier, or a precursor thereof, to at least partly remove impurities comprising contacting the carrier, or the precursor thereof, with a treatment solution comprising a salt; a process for preparing a catalyst; the catalyst; a process for preparing an olefin oxide by reacting an olefin with oxygen in the presence of the catalyst; and a process for preparing a 1,2-diol, a 1,2-diol ether or an alkanolamine.
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: August 6, 2013
    Assignee: Shell Oil Company
    Inventors: John Robert Lockemeyer, Randall Clayton Yeates
  • Patent number: 8497301
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: May 14, 2012
    Date of Patent: July 30, 2013
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 8492597
    Abstract: The present invention describes a process for the production of propylene glycol from glycerol, the transformation of purified glycerol to propylene glycol being carried out by means of a reaction of hydrogenolysis, in the liquid phase, where the two stages of the reaction take place simultaneously and in one and the same reactor (1) under specified conditions of temperature and pressure, and the effluent from the fixed-bed reactor (1) is led to subsequent process stages that comprise separation and purification.
    Type: Grant
    Filed: February 24, 2011
    Date of Patent: July 23, 2013
    Assignee: Petroleo Brasileiro S.A.-Petrobras
    Inventors: Carlos René Klotz Rabello, Marlito Gomes Junior, Bernardo Galvão Siqueira, Raphael Bezerra de Menezes, Wilson Kenzo Huziwara, Tomas Shinobu Yamada, Lígia Maria Marçareli de Oliveira, Giselle de Carvalho Oliveira, William Victor Carlos Cândido
  • Patent number: 8492595
    Abstract: Disclosed are methods for generating propylene glycol, ethylene glycol and other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols from biomass using hydrogen produced from the biomass. The methods involve reacting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and then reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycol and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production of oxygenated hydrocarbons without the need for hydrogen from an external source.
    Type: Grant
    Filed: June 8, 2012
    Date of Patent: July 23, 2013
    Assignee: Virent, Inc.
    Inventor: Randy D. Cortright
  • Patent number: 8476478
    Abstract: The present invention relates to a process for producing hydrogenolysis products of polyhydric alcohols with a good selectivity and a high yield, as well as hydrogenolysis catalysts used in the production process. The present invention provides (1) a process for producing a hydrogenolysis product of a polyhydric alcohol which includes the step of reacting the polyhydric alcohol with hydrogen in the presence of a catalyst containing a copper component, wherein the catalyst is a catalyst (A) containing the copper component, an iron component and an aluminum component, or a catalyst (B) containing the copper component and a silicon component; and (2) a hydrogenolysis catalyst for polyhydric alcohols which includes a copper component, an iron component and an aluminum component, and (3) a hydrogenolysis catalyst for polyhydric alcohols which includes a copper component and a silicon component.
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: July 2, 2013
    Assignee: Kao Corporation
    Inventors: Nobuyoshi Suzuki, Masazumi Tamura, Yohei Yoshikawa, Taku Mimura, Masakatsu Takahashi
  • Patent number: 8471075
    Abstract: A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of first metal, a silicaceous support, and at least one support modifier. Preferably, the first metal is selected from the group consisting of copper, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, titanium, zinc, chromium, rhenium, molybdenum, and tungsten. In addition the catalyst may comprise a second metal preferably selected from the group consisting of copper, molybdenum, tin, chromium, iron, cobalt, vanadium, tungsten, palladium, platinum, lanthanum, cerium, manganese, ruthenium, rhenium, gold, and nickel.
    Type: Grant
    Filed: February 2, 2010
    Date of Patent: June 25, 2013
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
  • Patent number: 8450535
    Abstract: A process for the selective and direct formation of ethanol from acetic acid comprising contacting a feed stream containing acetic acid and hydrogen in vapor form at an elevated temperature with a hydrogenation catalyst comprising cobalt and one or more metals selected from the group consisting of palladium, platinum, rhodium, ruthenium, rhenium, iridium, chromium, copper, tin, molybdenum, tungsten, vanadium, zinc and iron on a catalyst support.
    Type: Grant
    Filed: April 4, 2011
    Date of Patent: May 28, 2013
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Barbara F. Kimmich, Jan Cornelis van der Waal, James H. Zink, Virginie Zuzaniuk, Josefina T. Chapman, Laiyuan Chen
  • Patent number: 8415511
    Abstract: A catalyst composition/system can include: a platinum catalyst metal (Pt) and/or rhenium catalyst metal (Re) on a first support; and a ruthenium catalyst metal (Ru) and/or rhenium catalyst metal (Re) on a second support or a platinum catalyst metal (Pt) and a ruthenium catalyst metal (Ru) and/or a rhenium catalyst metal (Re) on the same support. The Pt:Ru, Re:Pt and/or Re:Ru weight ratio can be between about 1:4 and about 4:1. The support can be alumina, carbon, silica, a zeolite, TiO2, ZrO2 or another suitable material. The first and second support can be on the same support structure or on different support structures. In one option, the first and second supports can be positioned such that the Pt and/or Re are capable of catalyzing a dehydrogenation and/or reforming reaction that produces hydrogen and the Ru and/or Re are capable of catalyzing a hydrogenolysis reaction.
    Type: Grant
    Filed: June 8, 2010
    Date of Patent: April 9, 2013
    Assignee: University of Kansas
    Inventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
  • Patent number: 8410319
    Abstract: A catalytic process for generating at least one polyol from a feedstock comprising cellulose is performed in a continuous manner. The process involves, contacting, continuously, hydrogen, water, and a feedstock comprising cellulose, with a catalyst to generate an effluent stream comprising at least one polyol, water, hydrogen, and at least one co-product. The water, hydrogen, and at least one co-product are separated from the effluent stream and recycled to the reaction zone. The polyol is recovered from the effluent stream.
    Type: Grant
    Filed: July 28, 2011
    Date of Patent: April 2, 2013
    Assignees: UOP LLC, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Tom N. Kalnes, John Q. Chen, Joseph A. Kocal, Tao Zhang, Aiqin Wang, Mingyuan Zheng, Changzhi Li, Jifeng Pang
  • Patent number: 8394999
    Abstract: A process to convert glycerin into propylene glycol and purifying the produced propylene glycol is described. The glycerin-based propylene glycol production requires only one process step compared to petroleum/natural gas-based propylene glycol production requires multiple process steps, and thus represents a cost savings.
    Type: Grant
    Filed: March 12, 2012
    Date of Patent: March 12, 2013
    Assignee: GTC Technology US LLC
    Inventors: Zhongyi Ding, Joseph Chiu, Weihua Jin
  • Patent number: 8378152
    Abstract: Propylene glycol is produced by a method of producing propylene glycol, the method including: obtaining propylene glycol by performing catalytic hydrogenation of glycerol in the presence of a catalyst, the catalyst containing zinc oxide and at least one of copper and copper oxide, and the catalyst, after being reduced at 180° C. to 230° C. in the presence of hydrogen, showing a half width of from 0.4 to 1.1 of a peak having a peak top at a position at which a diffraction angle (2?±0.2°) is 43.1° in an X-ray diffraction pattern obtained using CuK? as a radiation source.
    Type: Grant
    Filed: April 21, 2009
    Date of Patent: February 19, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Kouno, Shuji Ozawa, Naritoshi Yoshimura
  • Patent number: 8338326
    Abstract: Tungsten carbide catalysts are used in preparation of ethylene glycol by hydrogenating degradation of cellulose. The catalyst includes tungsten carbide as main catalytic active component, added with small amount of one or more transition metals such as nickel, cobalt, iron, ruthenium, rhodium, palladium, osmium, iridium, platinum, and copper as the second metal, supported on one or more porous complex supports such as active carbon, alumina, silica, titanium dioxide, silicon carbide, zirconium oxide, for conversion of cellulose to ethylene glycol. The catalyst realizes high efficiency, high selectivity, and high yield in the conversion of cellulose to ethylene glycol at the temperature of 120-300° C., hydrogen pressure of 1-10 MPa, and hydrothermal conditions. Compared to the existing industrial synthetic method of ethylene glycol using ethylene as feedstock, the invention has the advantages of using renewable raw material resources, environment friendly process, and excellent atom economy.
    Type: Grant
    Filed: October 31, 2008
    Date of Patent: December 25, 2012
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventor: Tao Zhang
  • Patent number: 8334416
    Abstract: A process for the removal of hydroxypropane from a crude product stream from the hydrogenation of glycerol, the crude product stream comprising 1,2-propanediol and hydroxypropanone as impurity, the process comprising: (a) where required condensing the crude product stream; and (b) contacting the crude product phase in the liquid phase with a stream of a hydrogen-containing gas in the presence of a heterogeneous catalyst at suitable temperatures and pressures such that hydroxypropanone present in the crude product stream is converted to the desired propanediol.
    Type: Grant
    Filed: December 2, 2008
    Date of Patent: December 18, 2012
    Assignee: Davy Process Technology Limited
    Inventors: Michael William Marshall Tuck, Robert Wild, Simon Nicholas Tilley
  • Patent number: 8324434
    Abstract: The present invention provides an improved hydrogenation processes wherein heat is efficiently managed so that catalyst productivity is optimized. More particularly, in the processes of the present invention, a nonaqueous solvent is added to a reactant to provide a nonaqueous solvent/reactant mixture that can act as a heat sink and absorb at least a portion of the heat generated within the reactor. Desirably, a reaction product, or a solvent with a minimal number of hydroxyl groups, is utilized so that the formation of unwanted byproducts can be minimized.
    Type: Grant
    Filed: February 28, 2009
    Date of Patent: December 4, 2012
    Assignee: Dow Global Technologies, LLC
    Inventors: David C. Molzahn, Kenneth A. Burdett, William L. Gibson, Karel J. Kriel, James E. McCreight, Indresh Mathur
  • Patent number: 8323937
    Abstract: A catalytic process for generating at least one polyol from a feedstock comprising cellulose is performed in a continuous manner using a catalyst comprising nickel tungsten carbide. The process involves, contacting, continuously, hydrogen, water, and a feedstock comprising cellulose, with the catalyst to generate an effluent stream comprising at least one polyol and recovering the polyol from the effluent stream.
    Type: Grant
    Filed: July 28, 2011
    Date of Patent: December 4, 2012
    Assignees: UOP LLC, Dalian Institute of Chemical Physics
    Inventors: Tao Zhang, Aiqin Wang, Mingyuan Zheng, Changzhi Li, Jifeng Pang, Tom N. Kalnes, John Q. Chen, Joseph A. Kocal
  • Patent number: 8324433
    Abstract: A method for producing ethylene glycol, including (a) adding a polyhydroxy compound and water to a sealed high-pressure reactor, (b) removing air and introducing hydrogen, and (c) allowing the polyhydroxy compound to react in the presence of a catalyst while stiffing. The catalyst includes a first active ingredient and a second active ingredient. The first active ingredient includes a transition metal of Group 8, 9, or 10 selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, iridium, and platinum, and/or a mixture thereof. The second active ingredient includes a metallic state of molybdenum and/or tungsten, or a carbide, nitride, or phosphide thereof. The method is carried out at a hydrogen pressure of 1-12 MPa, at a temperature of 120-300° C. for not less than 5 min in a one-step catalytic reaction. The efficiency, selectivity, and the yield of ethylene glycol are high. The preparation process is simple and the materials used are renewable.
    Type: Grant
    Filed: October 31, 2010
    Date of Patent: December 4, 2012
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Tao Zhang, Mingyuan Zheng, Aiqin Wang, Na Ji, Jifeng Pang, Zhijun Tai, Likun Zhou, Jingguang Chen, Xiaodong Wang
  • Patent number: 8293951
    Abstract: The present invention relates to a process for preparing 1,2-propanediol, in which a glycerol-containing stream, especially a stream obtained on the industrial scale in the production of biodiesel, is subjected to a hydrogenation in an at least three-stage reactor cascade.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: October 23, 2012
    Assignee: BASF SE
    Inventors: Jochem Henkelmann, Roman Prochazka, Oliver Bey, Stephan Maurer, Jochen Steiner, Heiko Urtel, Gerhard Theis, Peter Wahl
  • Patent number: 8273924
    Abstract: The present invention relates to a process for preparing 1,2-propanediol, in which a glycerol-containing stream, especially a stream obtained on the industrial scale in the production of biodiesel, is subjected to a low pressure hydrogenation.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: September 25, 2012
    Assignee: BASF SE
    Inventors: Jochem Henkelmann, Roman Prochazka, Oliver Bey, Stephan Maurer, Jochen Steiner, Heiko Urtel, Gerhard Theis, Peter Wahl, Michael Becker
  • Patent number: 8258351
    Abstract: The present invention relates to a process for producing a hydrogenolysis product of a polyhydric alcohol in the presence of a catalyst in which a conversion rate of the polyhydric alcohol as well as a selectivity to the hydrogenolysis product, in particular, a selectivity of glycerol to propanediols, can be enhanced. The process for producing a hydrogenolysis product of a polyhydric alcohol according to the present invention includes the step of subjecting a polyhydric alcohol solution having a water content of less than 10% by mass to hydrogenolysis by a fixed-bed continuous liquid phase reaction method in the presence of a hydrogenolysis catalyst.
    Type: Grant
    Filed: December 26, 2008
    Date of Patent: September 4, 2012
    Assignee: Kao Corporation
    Inventors: Nobuyoshi Suzuki, Masazumi Tamura, Taku Mimura
  • Patent number: 8252963
    Abstract: A catalyst composition can include: a support; a ruthenium catalyst (Ru) nanoparticle; and a linker linking the Ru nanoparticle to the support, wherein the linker is stable under hydrogenolysis conditions. In one aspect, the linker can include 3-aminopropyl trimethoxysilane (APTS) or derivatives thereof, such as those with amine functionality. In another aspect, the linker can include phosphotungstic acid (PTA) or other similar solid acid agents. In another aspect, the support can be selected from alumina, carbon, silica, a zeolite, TiO2, ZrO2, or another suitable material. A specific example of a support includes zeolite, such as a NaY zeolite. The Ru nanoparticle can have a size range from about 1 nm to about 25 nm, and can be obtained by reduction of Ru salts.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: August 28, 2012
    Assignee: University of Kansas
    Inventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
  • Patent number: 8252961
    Abstract: This invention relates generally to a process for value-added processing of fats and oils to yield glycerol and glycerol derivatives. More particularly, the process converts glycerol to acetol and then acetol to propylene glycol to produce a propylene glycol with ultra-low amounts of ethylene glycol. The propylene glycol thus produced may be used as an antifreeze, deicing compound, or anti-icing compound.
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: August 28, 2012
    Assignee: The Curators of The University of Missouri
    Inventor: Galen J. Suppes