Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/861)
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Patent number: 12139449Abstract: An alcohol production method in which an alcohol is produced from a carbonyl compound, the method including producing an alcohol by using a catalyst, the catalyst including a metal component including rhenium having an average valence of 4 or less and a carrier supporting the metal component, the carrier including zirconium oxide. A catalyst for producing an alcohol by hydrogenation of a carbonyl compound, the catalyst including a carrier including zirconium oxide and a metal component supported on the carrier, the metal component including rhenium having an average valence of 4 or less.Type: GrantFiled: January 21, 2021Date of Patent: November 12, 2024Assignee: Mitsubishi Chemical CorporationInventors: Takeshi Matsuo, Yumiko Yoshikawa, Naoyuki Sakamoto, Takayuki Aoshima
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Patent number: 11920203Abstract: Lignocellulosic biomass (11) is processed to produce organic chemicals by (a) subjecting the biomass to a first hydrolysis (14) to hydrolyse hemicellulose, to form a liquid component comprising the products of hemicellulose hydrolysis in solution, and a solid component comprising cellulose and lignin; (b) then subjecting the solid component to a second hydrolysis (20), so as to hydrolyse cellulose and vaporise the resulting products of cellulose hydrolysis; and (c) then condensing (22) the resulting vapours to form an aqueous solution (25) containing the products of cellulose hydrolysis. After the first hydrolysis (14) and before the second hydrolysis (20), the process also comprises subjecting the solid component to a washing step (16). In this washing step (16) the solid component is washed with the aqueous solution (25) that contains the products of cellulose hydrolysis. Hence the resultant solution contains the products of both the first and the second hydrolysis steps (14, 20).Type: GrantFiled: July 15, 2019Date of Patent: March 5, 2024Assignee: NOVA PANGAEA TECHNOLOGIES (UK) LIMITEDInventors: Martin Spangsberg Holm, Aivars Zhurinsh
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Patent number: 11504698Abstract: A Ni—Al2O3@Al2O3—SiO2 catalyst with coated structure is provided. The catalyst has a specific surface area of 98 m2/g to 245 m2/g, and a pore volume of 0.25 cm3/g to 1.1 cm3/g. A mass ratio of an Al2O3 carrier to active component Ni in the catalyst is Al2O3:Ni=100:4˜26, a mass ratio of the Al2O3 carrier to an Al2O3—SiO2 coating layer is Al2O3:Al2O3—SiO2=100:0.1˜3, and a molar ratio of Al to Si in the Al2O3—SiO2 coating layer is 0.01 to 1. Ni particles are distributed on a surface of the Al2O3 carrier in an amorphous or highly dispersed state and have a grain size less than or equal to 8 nm, and the coating layer is filled among the Ni particles.Type: GrantFiled: January 25, 2018Date of Patent: November 22, 2022Assignee: SHANXI UNIVERSITYInventors: Yongxiang Zhao, Haitao Li, Lili Zhao, Hongxi Zhang, Zijin Sun, Yongzhao Wang
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Patent number: 11498891Abstract: The present invention relates to a process for making 1,4-butanediol. The process may include reacting a solution comprising 1,4-butynediol with hydrogen in a presence of a catalyst. The catalyst may include cerium.Type: GrantFiled: August 6, 2019Date of Patent: November 15, 2022Assignee: W.R. Grace & Co.-ConnInventor: Stephen R. Schmidt
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Patent number: 11407701Abstract: The present invention relates to a method for continuous production of 2,3-butanediol by hydrogenation of 3-hydroxybutanone with hydrogen in the presence of a heterogeneous hydrogenation catalyst filled in one or more fixed-bed flow tubular reactor systems comprising one or more tubes with an inner diameter from 1 mm to 6 mm.Type: GrantFiled: November 8, 2018Date of Patent: August 9, 2022Assignee: FUNDACION TECNALIA RESEARCH & INNOVATIONInventors: José Ramón Ochoa Gómez, Susana Pérez Gil, María Del Mar Díaz De Guereñu Zabarte, Inés Rincón Arroyo
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Patent number: 11331658Abstract: Processes for activating precious metal-containing catalysts. The processes can decrease the amount of high purity hydrogen required for starting up a catalytic conversion process such as transalkylation of heavy aromatics, without detrimental impact to the metal activity. The processes can include a low temperature treatment step with a high purity first gas, such as hydrogen generated by electrolysis and/or reformer hydrogen diluted with high purity inert gas, and a high temperature treatment step with a low purity second gas such as the reformer hydrogen. Also, the processes can include mixing a hydrogen gas of high or low purity with a high purity inert gas to form a gas mixture with a proportion of hydrogen no less than 2% and a reduced carbon monoxide concentration relative to the low purity hydrogen, and contacting the catalyst with the gas mixture.Type: GrantFiled: March 12, 2020Date of Patent: May 17, 2022Assignee: ExxonMobil Chemical Patents Inc.Inventors: Paul Podsiadlo, Robert G. Tinger, Todd E. Detjen, Jesus A. Ramos, Jeffrey L. Andrews, Travis D. Sparks
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Patent number: 11253839Abstract: Shaped porous carbon products and processes for preparing these products are provided. The shaped porous carbon products can be used, for example, as catalyst supports and adsorbents. Catalyst compositions including these shaped porous carbon products, processes of preparing the catalyst compositions, and various processes of using the shaped porous carbon products and catalyst compositions are also provided.Type: GrantFiled: May 18, 2020Date of Patent: February 22, 2022Assignee: Archer-Daniels-Midland CompanyInventors: Joshua Terrian, Andrew J. Ingram, Eric L. Dias, Alfred Hagemeyer, Hong X. Jiang, James Longmire, James A. W. Shoemaker, Valery Sokolovskii, Guang Zhu, Vincent J. Murphy, Gary M. Diamond
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Patent number: 10940465Abstract: Disclosed is an acid-resistant alloy catalyst comprising nickel, one or more rare earth elements, stannum and aluminum. The acid-resistant alloy catalyst is low-cost and stable, and does not need a carrier, and can be stably used in continuous industrial production, thus achieving a low production cost.Type: GrantFiled: January 14, 2020Date of Patent: March 9, 2021Assignees: The Coca-Cola CompanyInventors: Jing Liu, Hongbin Qi, Haiyu Ren, Indra Prakash, Yu Shi
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Patent number: 10544073Abstract: Processes for producing propylene glycol are disclosed. The processes may comprise subjecting a polyol to a hydrogenolysis reaction, thus producing propylene glycol and a product stream including an unreacted polyol and at least one unwanted compound. The process may include subjecting the product stream to a process that removes at least a portion of the at least one unwanted compound, thus producing a cleaned product stream, and subjecting the cleaned product stream to the hydrogenolysis reaction. Systems for implementing such processes are also described.Type: GrantFiled: December 9, 2014Date of Patent: January 28, 2020Assignee: ARCHER DANIELS MIDLAND COMPANYInventors: John G Soper, Joshua Terrian
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Patent number: 10544072Abstract: Continuous processes for making ethylene glycol form aldohexose-yielding carbohydrates are disclosed which enhance the selectivity to ethylene glycol.Type: GrantFiled: June 2, 2017Date of Patent: January 28, 2020Assignee: Iowa Corn Promotion BoardInventors: David James Schreck, Ray Chrisman, Brooke Albin, Nye Clinton, Marion McKinley Bradford, Donald Bunning
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Patent number: 10519124Abstract: Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.Type: GrantFiled: April 25, 2018Date of Patent: December 31, 2019Assignee: ARCHER DANIELS MIDLAND COMPANYInventors: Kenneth Stensrud, Chi-Cheng Ma, Kevin Martin
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Patent number: 10487032Abstract: An object of the present invention is to provide high-quality 1,4BG capable of working out to a raw material of PBT with good color tone, by efficiently removing and refining impurities mixed when producing a biomass-derived 1,4BG on an industrial scale and the present invention relates to a production method of refined 1,4BG, where a crude 1,4BG-containing solution is obtained from refined raw material 1,4BG obtained by removing bacterial cells, salt contents and water from the fermentation culture medium, through a step of removing high-boiling-point components and/or low-boiling-point components by distillation and/or a step of converting an unsaturated compound to a hydride and the target product is obtained as a side stream in a further distillation step.Type: GrantFiled: December 4, 2014Date of Patent: November 26, 2019Assignees: MITSUBISHI CHEMICAL CORPORATION, GENOMATICA, INC.Inventors: Masaru Utsunomiya, Yusuke Izawa, Norikazu Konishi, Kota Tanaka, Shinichiro Matsuzono, Takayuki Suzuki, Michael Japs, Mark Burk, Warren Clark
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Patent number: 10450255Abstract: A process for the preparation of glycols from a saccharide-containing feedstock comprising the steps of: (a) preparing a reaction mixture in a reactor vessel comprising the saccharide-containing feedstock, a solvent, a catalyst component with retro-aldol catalytic capabilities and a first hydrogenation catalyst comprising an element selected from groups 8, 9 and 10 of the periodic table; (b) supplying hydrogen gas to the reaction mixture in the reactor vessel; (c) monitoring the activity of the first hydrogenation catalyst; (d) preparing a second hydrogenation catalyst by contacting in a reactor a catalyst precursor comprising one or more elements selected from chromium and groups 8, 9, 10 and 11 of the periodic table with hydrazine to convert the catalyst precursor into the second hydrogenation catalyst; (e) when the hydrogenation activity declines, supplying the second hydrogenation catalyst to the reactor vessel to supplement the declined hydrogenation activity in the reactor vessel.Type: GrantFiled: September 27, 2016Date of Patent: October 22, 2019Assignee: SHELL OIL COMPANYInventor: Duraisamy Muthusamy
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Patent number: 10113118Abstract: The invention relates to a method for producing liquid hydrocarbon, the method comprising: providing a feed material, pressurizing the feed material to a predetermined process pressure, heating the pressurized feed material to a predetermined process temperature, reacting the pressurized and heated feed material for a predetermined period of time, cooling the reacted feed material and mechanically separating a high viscosity fraction from the converted feed material before conveying the remaining converted feed mass through a pressure reduction system and further through a separation system.Type: GrantFiled: December 22, 2014Date of Patent: October 30, 2018Assignee: STEEPER ENERGY APSInventor: Steen Brummerstedt Iversen
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Patent number: 10017439Abstract: A method of isolating and purifying a product of sugar alcohol or anhydrosugar alcohol hydrogenolysis from a reaction mixture containing sorbitans, 1,2,4-butanetriol (BTO), 1,2,5,6-hexanetetrol (HTO), among other byproducts of a hydrogenolysis reaction of a sugar alcohol and/or a mono- or di-dehydrative product of a sugar alcohol is described. The method involves contacting the mixture having the products of sugar alcohol or anhydrosugar alcohol hydrogenation and other C1-C6 alcohols and polyols with a resin material adapted for chromatography under conditions where the products preferentially associates with the resin relative to other components in the mixture, and eluting products from the resin with a solvent. The method suggests a way for separation of aliphatic polyols generated from the hydrogenolysis of sugar alcohols or anhydrosugar alcohols.Type: GrantFiled: July 13, 2017Date of Patent: July 10, 2018Assignee: Archer Daniels Midland CompanyInventors: Brennan Smith, ChiCheng Ma
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Patent number: 9732469Abstract: A selective removal of metal and its anion species that are detrimental to subsequent hydrothermal hydrocatalytic conversion from the biomass feed prior to carrying out catalytic hydrogenation/hydrogenolysis/hydrodeoxygenation of the biomass in a manner that does not reduce the effectiveness of the hydrothermal hydrocatalytic treatment while minimizing the amount of water used in the process is provided.Type: GrantFiled: June 23, 2016Date of Patent: August 15, 2017Assignee: SHELL OIL COMPANYInventors: Joseph Broun Powell, Juben Nemchand Chheda
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Patent number: 9732020Abstract: A method of isolating and purifying 1,2,5,6 hexanetetrol (HTO) from a reaction mixture containing HTO and other byproducts of a hydrogenation reaction of a sugar alcohol and/or a mono- or di-dehydrative product of a sugar alcohol is described. The method involves contacting the mixture comprising HTO and other C1-C6 alcohols and polyols with a resin material adapted for chromatography under conditions where HTO preferentially associates with the resin relative to other components in the mixture, and eluting HTO from said resin with a solvent.Type: GrantFiled: April 10, 2015Date of Patent: August 15, 2017Assignee: Archer Daniels Midland CompanyInventors: Brennan Smith, ChiCheng Ma
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Patent number: 9708764Abstract: A selective removal of metal and its anion species that are detrimental to subsequent hydrothermal hydrocatalytic conversion from the biomass feed prior to carrying out catalytic hydrogenation/hydrogenolysis/hydrodeoxygenation of the biomass in a manner that does not reduce the effectiveness of the hydrothermal hydrocatalytic treatment while minimizing the amount of water used in the process is provided.Type: GrantFiled: June 23, 2016Date of Patent: July 18, 2017Assignee: SHELL OIL COMPANYInventors: Joseph Broun Powell, Juben Nemchand Chheda
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Patent number: 9708763Abstract: A selective removal of metal and its anion species that are detrimental to subsequent hydrothermal hydrocatalytic conversion from the biomass feed prior to carrying out catalytic hydrogenation/hydrogenolysis/hydrodeoxygenation of the biomass in a manner that does not reduce the effectiveness of the hydrothermal hydrocatalytic treatment while minimizing the amount of water used in the process is provided.Type: GrantFiled: June 23, 2016Date of Patent: July 18, 2017Assignee: SHELL OIL COMPANYInventors: Joseph Broun Powell, Juben Nemchand Chheda
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Patent number: 9533930Abstract: In the process of distilling a polyol product mixture including one or both of a biobased propylene glycol and a biobased ethylene glycol from the reaction of hydrogen with a biobased feed, it has been discovered that undesirable epoxides can form, and the present invention provides means for guarding against their formation, for removing epoxides which do form by particular methods of distilling, and for removing the epoxides from a finished, otherwise commercially acceptable biobased glycol product.Type: GrantFiled: February 4, 2015Date of Patent: January 3, 2017Inventors: Kevin J. Adlaf, Paul D. Bloom, William Chris Hoffman, Chicheng Ma, John G. Soper, Brad Zenthoefer
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Patent number: 9527788Abstract: 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: GrantFiled: June 27, 2013Date of Patent: December 27, 2016Assignee: Shell Oil CompanyInventors: Glenn Charles Komplin, Joseph Broun Powell
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Patent number: 9499402Abstract: In a method of preparing a ruthenium-containing catalyst on a non-conductive metal oxide support comprises dissolving one or more ruthenium precursor compounds in an liquid organic polyol, combining the thus obtained solution with (a) nano-powder(s) of one or more metal oxides in a ratio of moles metal oxide(s) to moles ruthenium atoms in the one or more ruthenium precursor compounds of about 0:1 to about 6:1, the metal oxide nano-powder(s) having a surface area of from about 5 to about 300 m2/g and a point of zero charge (PZC) of pH 5.5 or higher, agitating the thus obtained mixture, adding pre-shaped alumina support pellets to the agitated mixture, which is than heated at a temperature of about 50° C.Type: GrantFiled: May 15, 2012Date of Patent: November 22, 2016Assignee: Elbit Systems Land and C4I Ltd.Inventor: Debasish Chakraborty
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Patent number: 9492851Abstract: A selective removal of metal and its anion species that are detrimental to subsequent hydrothermal hydrocatalytic conversion from the biomass feed in a continuous or semi-continuous manner prior to carrying out catalytic hydrogenation/hydrogenolysis/hydrodeoxygenation of the biomass that does not reduce the effectiveness of the hydrothermal hydrocatalytic treatment while minimizing the amount of water used in the process is provided.Type: GrantFiled: December 18, 2014Date of Patent: November 15, 2016Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Robert Edward Trepte, Juben Nemchand Chheda
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Patent number: 9464015Abstract: A process for the hydrogenolysis of glycerol to produce propylene glycol as the major product comprising contacting the glycerol with hydrogen in the presence of a heterogeneous catalyst under conditions for the formation of propylene glycol is disclosed. In particular, propylene glycol is formed with a selectivity of greater than about 90%.Type: GrantFiled: March 6, 2014Date of Patent: October 11, 2016Assignee: UNIVERSITY OF SASKATCHEWANInventors: Ajay Kumar Dalai, Rajesh Vishnudev Sharma, Pardeep Kumar
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Patent number: 9447011Abstract: Methods, processes and systems for using solid catalysts to simultaneously produce lactic acid and propylene glycol from glycerol are provide, as are methods, processes and systems of converting glycerol use heterogeneous catalytic agents. Different combinations of catalysts and reaction conditions provide tunable ranges for the yields of lactic acid and propylene glycol. The conversion methods, processes and systems are not reliant on external hydrogen. Applications to crude glycerol, including that co-produced during biodiesel production, are also described.Type: GrantFiled: November 21, 2013Date of Patent: September 20, 2016Assignee: University of Tennessee Research FoundationInventors: Xiaofei Philip Ye, Lu Liu
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Patent number: 9404027Abstract: A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 200° C., at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 250° C. at pressures from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium.Type: GrantFiled: October 21, 2013Date of Patent: August 2, 2016Assignee: The Curators of the University of MissouriInventor: Galen J. Suppes
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Patent number: 9352304Abstract: This invention provides methods for producing ethylene glycol from polyhydroxy compounds such as cellulose, starch, hemicellulose, glucose, sucrose, fructose, fructan, xylose and soluble xylooligosaccharides. The methods uses polyhydroxy compounds as the reactant, a composite catalyst having active components comprising one or more transition metals of Groups 8, 9, or 10, including iron, cobalt, nickel, ruthenium, rhodium, palladium, iridium, and platinum, as well as tungsten oxide, tungsten sulfide, tungsten hydroxide, tungsten chloride, tungsten bronze oxide, tungsten acid, tungstate, metatungstate acid, metatungstate, paratungstate acid, paratungstate, peroxotungstic acid, pertungstate, heteropoly acid containing tungsten. Reacting at a temperature of 120-300° C. and a hydrogen pressure of 1-13 MPa under hydrothermal conditions to accomplish one-step catalytic conversion. It realizes efficient, highly selective, high yield preparation of ethylene glycol and propylene glycol from polyhydroxy compounds.Type: GrantFiled: November 4, 2010Date of Patent: May 31, 2016Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Tao Zhang, Zhijun Tai, Aiqin Wang, Mingyuan Zheng
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Patent number: 9328045Abstract: Bio-based terephthalic acid (bio-TPA), bio-based dimethyl terephthalate (bio-DMT), and bio-based polyesters, which are produced from a biomass containing a terpene or terpenoid, such as limonene are described, as well as the process of making these products. The bio-based polyesters include poly(alkylene terephthalate)s such as bio-based poly(ethylene terephthalate) (bio-PET), bio-based poly(trimethylene terephthalate) (bio-PTT), bio-based poly(butylene terephthalate) (bio-PBT), and bio-based poly(cyclohexylene dimethyl terephthalate) (bio-PCT).Type: GrantFiled: January 9, 2014Date of Patent: May 3, 2016Assignee: SAUDI BASIC INDUSTRIES CORPORATIONInventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
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Patent number: 9302965Abstract: The invention provides a process for the preparation of ethylene glycol and 1,2-propylene glycol from starting material comprising one or more saccharides, by contacting said starting material with hydrogen in a reactor in the presence of a solvent and a catalyst system with catalytic hydrogenation abilities, wherein the process comprises the steps of: i) introducing a first portion of the starting material into the reactor such that the initial concentration of the saccharide in the solvent in the reactor is no more than 2 wt %; ii) allowing at least 90 wt % of the saccharide in the first portion of the starting material to react; iii) subsequently adding further portions of starting material to the reactor over time; and removing reaction product from the reactor.Type: GrantFiled: April 1, 2014Date of Patent: April 5, 2016Assignee: Shell Oil CompanyInventors: Evert Van Der Heide, Govinda Subbanna Wagle
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Methods and systems for processing lignin during hydrothermal digestion of cellulosic biomass solids
Patent number: 9284242Abstract: 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: GrantFiled: October 30, 2013Date of Patent: March 15, 2016Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Kimberly Ann Johnson, Glenn Charles Komplin, Edward James Denton -
Patent number: 9221727Abstract: A composition comprising a supported hydrogenation catalyst comprising palladium and an organophosphorous compound, the supported hydrogenation catalyst being capable of selectively hydrogenating highly unsaturated hydrocarbons to unsaturated hydrocarbons. A method of making a selective hydrogenation catalyst comprising contacting a support with a palladium-containing compound to form a palladium supported composition, contacting the palladium supported composition with an organophosphorus compound to form a catalyst precursor, and reducing the catalyst precursor to form the catalyst.Type: GrantFiled: March 26, 2015Date of Patent: December 29, 2015Assignee: Chevron Phillips Chemical Company LPInventors: Tin-Tack Peter Cheung, Zongxuan Hong
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Patent number: 9174898Abstract: 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: GrantFiled: June 27, 2013Date of Patent: November 3, 2015Assignee: Shell Oil CompanyInventors: Glenn Charles Komplin, Joseph Broun Powell
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Patent number: 9132418Abstract: The present disclosure relates generally to catalyst support materials, catalysts and methods for using them, such as methods for converting sugars, sugar alcohols, glycerol, and bio-renewable organic acids to commercially-valuable chemicals and intermediates. One aspect of the invention is catalyst support material including ZrO2 and one or more oxides of manganese (MnOx), the catalyst support material being at least about 50 wt % ZrO2 and MnOx. In certain embodiments, the weight ratio of ZrO2 to MnOx is within the range of about 1:1 to about 30:1; and/or the catalyst support material is substantially free of any binder, extrusion aid or additional stabilizing agent.Type: GrantFiled: June 17, 2014Date of Patent: September 15, 2015Assignee: CLARIANT CORPORATIONInventors: Wenqin Shen, Franz G. Petzold, Karen Libby, Wayne Turbeville
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Patent number: 9035109Abstract: Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceeding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.Type: GrantFiled: May 29, 2014Date of Patent: May 19, 2015Assignee: Rennovia, Inc.Inventors: Eric L. Dias, James A. W. Shoemaker, Thomas R. Boussie, Vincent J. Murphy
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Patent number: 9018423Abstract: 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: GrantFiled: April 25, 2013Date of Patent: April 28, 2015Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, Torren Ryan Carlson, David Richard Corbin, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, H David Rosenfeld, Sourav Kumar Sengupta
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Patent number: 9012699Abstract: 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 9, 2014Date of Patent: April 21, 2015Assignee: Battelle Memorial InstituteInventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
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Publication number: 20150099903Abstract: 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: December 12, 2014Publication date: April 9, 2015Inventors: ALAN MARTIN ALLGEIER, Torren Ryan Carlson, David Richard Corbin, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C. Ritter, Sourav Kumar Sengupta
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Patent number: 9000041Abstract: 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: June 24, 2013Date of Patent: April 7, 2015Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Publication number: 20150094498Abstract: Processes and systems for converting glycerol to propylene glycol are disclosed. The glycerol feed is diluted with propylene glycol as the primary solvent, rather than water which is typically used. The diluted glycerol feed is sent to a reactor where the glycerol is converted to propylene glycol (as well as other byproducts) in the presence of a catalyst. The propylene glycol-containing product from the reactor is recycled as a solvent for the glycerol feed.Type: ApplicationFiled: December 3, 2014Publication date: April 2, 2015Applicant: BATTELLE MEMORIAL INSTITUTEInventors: John G. Frye, Jr., Aaron A. Oberg, Alan H. Zacher
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Publication number: 20150031923Abstract: The present disclosure relates generally to catalyst support materials, catalysts and methods for using them, such as methods for converting sugars, sugar alcohols, glycerol, and bio-renewable organic acids to commercially-valuable chemicals and intermediates. One aspect of the invention is catalyst support material including ZrO2 and one or more oxides of manganese (MnOx), the catalyst support material being at least about 50 wt % ZrO2 and MnOx. In certain embodiments, the weight ratio of ZrO2 to MnOx is within the range of about 1:1 to about 30:1; and/or the catalyst support material is substantially free of any binder, extrusion aid or additional stabilizing agent.Type: ApplicationFiled: June 17, 2014Publication date: January 29, 2015Applicant: CLARIANT CORPORATIONInventors: Wenqin Shen, Franz G. Petzold, Karen Libby, Wayne Turbeville
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Patent number: 8937202Abstract: Processes and systems for converting glycerol to propylene glycol are disclosed. The glycerol feed is diluted with propylene glycol as the primary solvent, rather than water which is typically used. The diluted glycerol feed is sent to a reactor where the glycerol is converted to propylene glycol (as well as other byproducts) in the presence of a catalyst. The propylene glycol-containing product from the reactor is recycled as a solvent for the glycerol feed.Type: GrantFiled: February 23, 2010Date of Patent: January 20, 2015Assignee: Battelle Memorial InstituteInventors: John G. Frye, Aaron A. Oberg, Alan H. Zacher
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Patent number: 8921616Abstract: An object of the invention is to provide a production method that can produce glycol from polyhydric alcohol with high selectivity and in a satisfactory yield. The object is achieved by using a silver catalyst in a reaction for synthesizing hydroxyketone from polyhydric alcohol having adjacent hydroxyl groups, and a hydrogenation catalyst in a reaction for synthesizing glycol from hydroxyketone.Type: GrantFiled: January 12, 2012Date of Patent: December 30, 2014Assignees: Clariant Catalysts (Japan) K.K., National University Corporation Chiba UniversityInventors: Tetsuro Kizaki, Keizo Iwatani, Xin Chen, Satoshi Sato
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Patent number: 8889585Abstract: A supported tungsten carbide catalyst comprises tungsten carbide as its active component and a mesoporous carbon as its support, wherein tungsten carbide is highly dispersed on the surface and in the channels of the mesoporous carbon, and the content of tungsten element is in the range from 30% to 42% by mass based on the mesoporous carbon. This catalyst can be prepared by impregnation process. This catalyst can be used for the direct catalytic conversion of cellulose to ethylene glycol under the hydrothermal conditions and at a temperature of 245° C. and the hydrogen pressure of 6 MPa with high reactivity, selectivity and stability.Type: GrantFiled: October 22, 2010Date of Patent: November 18, 2014Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Tao Zhang, Yanhua Zhang, Aiqin Wang, Mingyuan Zheng
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Patent number: 8877985Abstract: Methods and systems for co-producing higher hydrocarbons and glycols from bio-based feedstocks containing carbohydrates are disclosed.Type: GrantFiled: June 13, 2012Date of Patent: November 4, 2014Assignee: Shell Oil CompanyInventor: Joseph Broun Powell
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Patent number: 8877984Abstract: Disclosed is a process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid. Isophthalic acid is esterified with (3-methylcyclohexyl)methanol and the isophthalate ester hydrogenated to 1,3-cyclohexanedimethanol in a 2-stage process. The (3-methylcyclohexyl)methanol that is formed during the hydrogenation step is recycled to the esterification reaction. Also disclosed is a method for purifying and recovering the 1,3-cyclohexanedimethanol product.Type: GrantFiled: May 21, 2012Date of Patent: November 4, 2014Assignee: Eastman Chemical CompanyInventors: Benjamin Fredrick Barton, Steven Leroy Cook, Jeff Scott Howell, Noah Glenn McMillan, Damon Bryan Shackelford, Brent Alan Tennant, Phillip Wayne Turner
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Patent number: 8859826Abstract: 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: GrantFiled: April 25, 2013Date of Patent: October 14, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
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Patent number: 8859828Abstract: A process for converting a sugar, sugar alcohol, or glycerol to a valuable chemical is described. The process may use a support comprising zirconium oxide promoted by a polyacid or promoter material. A catalytically active metal may be impregnated on the polyacid-promoted zirconium oxide support and the catalyst may then be introduced the sugar, sugar alcohol, or glycerol a source of hydrogen under reaction conditions. At least 40 wt % of the sugar, sugar alcohol or glycerol may be converted to a polyol and/or a shorter carbon-chain alcohol that may include at least one of propylene glycol, ethylene glycol, glycerin, methanol, ethanol, propanol and butandiols. Specific processes for converting glycerin having a selectivity for propylene glycol and for converting sorbitol with a selectivity for propylene glycol, ethylene glycol, and/or glycerin are also described.Type: GrantFiled: March 3, 2010Date of Patent: October 14, 2014Assignee: Clariant CorporationInventors: Aiguo Liu, Wayne Turbeville, Christopher C. Luckett, Hui Hui (Faye) Li
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Patent number: 8853465Abstract: The present invention relates to a process for preparing neopentyl glycol (NPG) by continuously hydrogenating hydroxypivalaldehyde (HPA) with hydrogen, in the liquid phase, in the presence of a hydrogenation catalyst, in a hydrogenation reactor (5), by combining an HPA-comprising stream (1) with an NPG-comprising stream (2) to give a hydrogenation feed (4) and introducing the hydrogenation feed (4) into the hydrogenation reactor (5) and additionally supplying at least one pH regulator (3) selected from the group consisting of tertiary amine, an inorganic base, an inorganic acid and an organic acid to the HPA-comprising stream (1) or the NPG-comprising stream (2) or the hydrogenation feed (4), in order to establish a pH of 7.0 to 9.Type: GrantFiled: May 11, 2011Date of Patent: October 7, 2014Assignee: BASF SEInventors: Michael Steiniger, Maria Guixa Guardia, Kai Stehmeier
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Patent number: 8846984Abstract: 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: GrantFiled: April 25, 2013Date of Patent: September 30, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joseph E Murphy, Joachim C Ritter, Sourav Kumar Sengupta
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Patent number: 8846985Abstract: 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: GrantFiled: April 25, 2013Date of Patent: September 30, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta