Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/861)
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Patent number: 8809596Abstract: 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: GrantFiled: January 19, 2010Date of Patent: August 19, 2014Assignee: BASF SEInventors: Stephan Maurer, Roman Prochazka, Oliver Bey, Jochen Steiner, Jochem Henkelmann, Gerhard Theis, Peter Wahl, Frank Heimann
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Patent number: 8809593Abstract: 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: GrantFiled: February 25, 2011Date of Patent: August 19, 2014Assignee: Council of Scientific and Industrial ResearchInventors: Chandrasshekhar Vasant Rode, Amol Mahalingappa Hengne, Ajay Ashok Ghalwadkar, Rasika Bharat Mane, Pravinkumar Hansraj Mohite, Hari Shankar Potdar
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Patent number: 8759594Abstract: 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: GrantFiled: March 29, 2010Date of Patent: June 24, 2014Assignee: BASF SEInventors: Olivier Abillard, Rolf Pinkos, Gerd-Dieter Tebben, Tilman Sirch, Daniel Urbanczyk, Heiko Urtel, Rolf Tompers
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Patent number: 8754263Abstract: 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: GrantFiled: June 25, 2013Date of Patent: June 17, 2014Assignee: Virent, Inc.Inventor: Randy D. Cortright
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Patent number: 8754266Abstract: 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: GrantFiled: May 10, 2013Date of Patent: June 17, 2014Assignee: Battelle Memorial InstituteInventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
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Patent number: 8742180Abstract: 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: GrantFiled: November 13, 2012Date of Patent: June 3, 2014Assignee: Lyondell Chemical Technology, L.P.Inventors: Daniel F. White, Brian A. Salisbury, Jenny M. Oran Osment
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Patent number: 8735635Abstract: 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: GrantFiled: February 23, 2010Date of Patent: May 27, 2014Assignee: W. R. Grace & Co.-Conn.Inventor: Stephen Raymond Schmidt
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Publication number: 20140135511Abstract: 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: ApplicationFiled: January 22, 2014Publication date: May 15, 2014Applicant: MITSUBISHI CHEMICAL CORPORATIONInventors: Yusuke IZAWA, Masaru UTSUNOMIYA, Norikazu KONISHI, Kouta TANAKA
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METHODS AND SYSTEMS FOR PROCESSING LIGNIN DURING HYDROTHERMAL DIGESTION OF CELLULOSIC BIOMASS SOLIDS
Publication number: 20140121419Abstract: 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: ApplicationFiled: October 30, 2013Publication date: May 1, 2014Applicant: SHELL OIL COMPANYInventors: Joseph Broun POWELL, Kimberly Ann JOHNSON, Glenn Charles KOMPLIN, Edward James DENTON -
Patent number: 8692032Abstract: 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: GrantFiled: June 29, 2012Date of Patent: April 8, 2014Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Tao Zhang, Na Ji, Mingyuan Zheng, Aiqin Wang, Yuying Shu, Xiaodong Wang, Jingguang Chen
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Publication number: 20140087978Abstract: 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: ApplicationFiled: September 27, 2012Publication date: March 27, 2014Applicant: HALLIBURTON ENERGY SERVICES, INCInventor: Jay P. DEVILLE
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Publication number: 20140058138Abstract: 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: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Patent number: 8648005Abstract: 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: GrantFiled: September 10, 2009Date of Patent: February 11, 2014Assignee: Kao CorporationInventors: Toru Sakamoto, Shoji Hasegawa
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Patent number: 8642813Abstract: 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: GrantFiled: December 29, 2011Date of Patent: February 4, 2014Assignee: Virent, Inc.Inventors: Ming Qiao, Randy D. Cortright, John Kania, Elizabeth Woods
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Publication number: 20140005444Abstract: 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: ApplicationFiled: June 27, 2013Publication date: January 2, 2014Inventors: Glenn Charles KOMPLIN, Joseph Broun POWELL
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Publication number: 20140005445Abstract: 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: ApplicationFiled: June 27, 2013Publication date: January 2, 2014Inventors: Glenn Charles KOMPLIN, Joseph Broun KOMPLIN
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Patent number: 8603938Abstract: 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: GrantFiled: September 10, 2009Date of Patent: December 10, 2013Assignee: Kao CorporationInventors: Toru Sakamoto, Taku Mimura
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Publication number: 20130310613Abstract: 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: ApplicationFiled: May 18, 2012Publication date: November 21, 2013Applicant: UOP LLCInventor: Tom N. Kalnes
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Patent number: 8580119Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.Type: GrantFiled: November 27, 2012Date of Patent: November 12, 2013Assignee: Menlo Energy Management, LLCInventors: Gaurav Shah, Sunil Suri
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Publication number: 20130289311Abstract: 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: ApplicationFiled: April 25, 2013Publication date: October 31, 2013Inventors: ALAN MARTIN ALLGEIER, WATHUDURA INDIKA NAMAL DE SILVA, CARL MENNING, JOSEPH E. MURPHY, JOACHIM C. RITTER, SOURAV KUMAR SENGUPTA
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Publication number: 20130289319Abstract: 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: ApplicationFiled: April 25, 2013Publication date: October 31, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joachim C. Ritter, Sourav Kumar Sengupta
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Publication number: 20130289318Abstract: 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: ApplicationFiled: April 25, 2013Publication date: October 31, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Alan Martin ALLGEIER, Torren Ryan CARLSON, Wathudura Indika Namal DE SILVA, Ekaterini KOROVESSI, Carl MENNING, Joachim C. RITTER, H David ROSENFELD, Sourav Kumar SENGUPTA
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Publication number: 20130289312Abstract: 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: ApplicationFiled: April 25, 2013Publication date: October 31, 2013Applicant: E I DU PONT DE MEMOURS AND COMPANYInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joachim C. Ritter, Sourav Kumar Sengupta
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Patent number: 8563783Abstract: 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: GrantFiled: August 27, 2012Date of Patent: October 22, 2013Assignee: The Curators of the University of MissouriInventor: Galen J. Suppes
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Publication number: 20130253231Abstract: 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: ApplicationFiled: May 10, 2013Publication date: September 26, 2013Applicant: Battelle Memorial InstituteInventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
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Publication number: 20130253230Abstract: 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: ApplicationFiled: March 23, 2012Publication date: September 26, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: David William Norman, Jonathan Michael Penney, Peter Borden Mackenzie
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Publication number: 20130225874Abstract: 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: ApplicationFiled: April 8, 2013Publication date: August 29, 2013Applicant: ROQUETTE FRERESInventor: ROQUETTE FRERES
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Publication number: 20130217923Abstract: 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: ApplicationFiled: July 1, 2011Publication date: August 22, 2013Applicant: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Lioubov Kiwi-Minsker, Igor Iouranov
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Patent number: 8501987Abstract: 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: GrantFiled: March 16, 2009Date of Patent: August 6, 2013Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences BP P.L.C.Inventors: Ying Sun, Hua Wang, Zhongmin Liu, Martin Philip Atkins
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Patent number: 8501664Abstract: 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: GrantFiled: November 15, 2007Date of Patent: August 6, 2013Assignee: Shell Oil CompanyInventors: John Robert Lockemeyer, Randall Clayton Yeates
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Patent number: 8497301Abstract: 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: GrantFiled: May 14, 2012Date of Patent: July 30, 2013Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 8492597Abstract: 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: GrantFiled: February 24, 2011Date of Patent: July 23, 2013Assignee: Petroleo Brasileiro S.A.-PetrobrasInventors: 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
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Patent number: 8492595Abstract: 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: GrantFiled: June 8, 2012Date of Patent: July 23, 2013Assignee: Virent, Inc.Inventor: Randy D. Cortright
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Patent number: 8476478Abstract: 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: GrantFiled: February 16, 2012Date of Patent: July 2, 2013Assignee: Kao CorporationInventors: Nobuyoshi Suzuki, Masazumi Tamura, Yohei Yoshikawa, Taku Mimura, Masakatsu Takahashi
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Patent number: 8471075Abstract: 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: GrantFiled: February 2, 2010Date of Patent: June 25, 2013Assignee: Celanese International CorporationInventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
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Patent number: 8450535Abstract: 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: GrantFiled: April 4, 2011Date of Patent: May 28, 2013Assignee: Celanese International CorporationInventors: Victor J. Johnston, Barbara F. Kimmich, Jan Cornelis van der Waal, James H. Zink, Virginie Zuzaniuk, Josefina T. Chapman, Laiyuan Chen
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Patent number: 8415511Abstract: 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: GrantFiled: June 8, 2010Date of Patent: April 9, 2013Assignee: University of KansasInventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
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Patent number: 8410319Abstract: 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: GrantFiled: July 28, 2011Date of Patent: April 2, 2013Assignees: UOP LLC, Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Tom N. Kalnes, John Q. Chen, Joseph A. Kocal, Tao Zhang, Aiqin Wang, Mingyuan Zheng, Changzhi Li, Jifeng Pang
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Patent number: 8394999Abstract: 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: GrantFiled: March 12, 2012Date of Patent: March 12, 2013Assignee: GTC Technology US LLCInventors: Zhongyi Ding, Joseph Chiu, Weihua Jin
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Patent number: 8378152Abstract: 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: GrantFiled: April 21, 2009Date of Patent: February 19, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Kouno, Shuji Ozawa, Naritoshi Yoshimura
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Patent number: 8338326Abstract: 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: GrantFiled: October 31, 2008Date of Patent: December 25, 2012Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventor: Tao Zhang
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Patent number: 8334416Abstract: 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: GrantFiled: December 2, 2008Date of Patent: December 18, 2012Assignee: Davy Process Technology LimitedInventors: Michael William Marshall Tuck, Robert Wild, Simon Nicholas Tilley
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Patent number: 8324434Abstract: 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: GrantFiled: February 28, 2009Date of Patent: December 4, 2012Assignee: Dow Global Technologies, LLCInventors: David C. Molzahn, Kenneth A. Burdett, William L. Gibson, Karel J. Kriel, James E. McCreight, Indresh Mathur
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Patent number: 8323937Abstract: 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: GrantFiled: July 28, 2011Date of Patent: December 4, 2012Assignees: UOP LLC, Dalian Institute of Chemical PhysicsInventors: Tao Zhang, Aiqin Wang, Mingyuan Zheng, Changzhi Li, Jifeng Pang, Tom N. Kalnes, John Q. Chen, Joseph A. Kocal
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Patent number: 8324433Abstract: 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: GrantFiled: October 31, 2010Date of Patent: December 4, 2012Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Tao Zhang, Mingyuan Zheng, Aiqin Wang, Na Ji, Jifeng Pang, Zhijun Tai, Likun Zhou, Jingguang Chen, Xiaodong Wang
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Patent number: 8293951Abstract: 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: GrantFiled: August 29, 2008Date of Patent: October 23, 2012Assignee: BASF SEInventors: Jochem Henkelmann, Roman Prochazka, Oliver Bey, Stephan Maurer, Jochen Steiner, Heiko Urtel, Gerhard Theis, Peter Wahl
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Patent number: 8273924Abstract: 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: GrantFiled: August 29, 2008Date of Patent: September 25, 2012Assignee: BASF SEInventors: Jochem Henkelmann, Roman Prochazka, Oliver Bey, Stephan Maurer, Jochen Steiner, Heiko Urtel, Gerhard Theis, Peter Wahl, Michael Becker
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Patent number: 8258351Abstract: 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: GrantFiled: December 26, 2008Date of Patent: September 4, 2012Assignee: Kao CorporationInventors: Nobuyoshi Suzuki, Masazumi Tamura, Taku Mimura
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Patent number: 8252963Abstract: 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: GrantFiled: June 9, 2010Date of Patent: August 28, 2012Assignee: University of KansasInventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
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Patent number: 8252961Abstract: 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: GrantFiled: December 19, 2008Date of Patent: August 28, 2012Assignee: The Curators of The University of MissouriInventor: Galen J. Suppes