Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/861)
  • Patent number: 10544072
    Abstract: Continuous processes for making ethylene glycol form aldohexose-yielding carbohydrates are disclosed which enhance the selectivity to ethylene glycol.
    Type: Grant
    Filed: June 2, 2017
    Date of Patent: January 28, 2020
    Assignee: Iowa Corn Promotion Board
    Inventors: David James Schreck, Ray Chrisman, Brooke Albin, Nye Clinton, Marion McKinley Bradford, Donald Bunning
  • Patent number: 10544073
    Abstract: 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: Grant
    Filed: December 9, 2014
    Date of Patent: January 28, 2020
    Assignee: ARCHER DANIELS MIDLAND COMPANY
    Inventors: John G Soper, Joshua Terrian
  • Patent number: 10519124
    Abstract: 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: Grant
    Filed: April 25, 2018
    Date of Patent: December 31, 2019
    Assignee: ARCHER DANIELS MIDLAND COMPANY
    Inventors: Kenneth Stensrud, Chi-Cheng Ma, Kevin Martin
  • Patent number: 10487032
    Abstract: 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: Grant
    Filed: December 4, 2014
    Date of Patent: November 26, 2019
    Assignees: MITSUBISHI CHEMICAL CORPORATION, GENOMATICA, INC.
    Inventors: Masaru Utsunomiya, Yusuke Izawa, Norikazu Konishi, Kota Tanaka, Shinichiro Matsuzono, Takayuki Suzuki, Michael Japs, Mark Burk, Warren Clark
  • Patent number: 10450255
    Abstract: 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: Grant
    Filed: September 27, 2016
    Date of Patent: October 22, 2019
    Assignee: SHELL OIL COMPANY
    Inventor: Duraisamy Muthusamy
  • Patent number: 10113118
    Abstract: 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: Grant
    Filed: December 22, 2014
    Date of Patent: October 30, 2018
    Assignee: STEEPER ENERGY APS
    Inventor: Steen Brummerstedt Iversen
  • Patent number: 10017439
    Abstract: 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: Grant
    Filed: July 13, 2017
    Date of Patent: July 10, 2018
    Assignee: Archer Daniels Midland Company
    Inventors: Brennan Smith, ChiCheng Ma
  • Patent number: 9732469
    Abstract: 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: Grant
    Filed: June 23, 2016
    Date of Patent: August 15, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Joseph Broun Powell, Juben Nemchand Chheda
  • Patent number: 9732020
    Abstract: 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: Grant
    Filed: April 10, 2015
    Date of Patent: August 15, 2017
    Assignee: Archer Daniels Midland Company
    Inventors: Brennan Smith, ChiCheng Ma
  • Patent number: 9708764
    Abstract: 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: Grant
    Filed: June 23, 2016
    Date of Patent: July 18, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Joseph Broun Powell, Juben Nemchand Chheda
  • Patent number: 9708763
    Abstract: 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: Grant
    Filed: June 23, 2016
    Date of Patent: July 18, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Joseph Broun Powell, Juben Nemchand Chheda
  • Patent number: 9533930
    Abstract: 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: Grant
    Filed: February 4, 2015
    Date of Patent: January 3, 2017
    Inventors: Kevin J. Adlaf, Paul D. Bloom, William Chris Hoffman, Chicheng Ma, John G. Soper, Brad Zenthoefer
  • Patent number: 9527788
    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: Grant
    Filed: June 27, 2013
    Date of Patent: December 27, 2016
    Assignee: Shell Oil Company
    Inventors: Glenn Charles Komplin, Joseph Broun Powell
  • Patent number: 9499402
    Abstract: 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: Grant
    Filed: May 15, 2012
    Date of Patent: November 22, 2016
    Assignee: Elbit Systems Land and C4I Ltd.
    Inventor: Debasish Chakraborty
  • Patent number: 9492851
    Abstract: 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: Grant
    Filed: December 18, 2014
    Date of Patent: November 15, 2016
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Robert Edward Trepte, Juben Nemchand Chheda
  • Patent number: 9464015
    Abstract: 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: Grant
    Filed: March 6, 2014
    Date of Patent: October 11, 2016
    Assignee: UNIVERSITY OF SASKATCHEWAN
    Inventors: Ajay Kumar Dalai, Rajesh Vishnudev Sharma, Pardeep Kumar
  • Patent number: 9447011
    Abstract: 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: Grant
    Filed: November 21, 2013
    Date of Patent: September 20, 2016
    Assignee: University of Tennessee Research Foundation
    Inventors: Xiaofei Philip Ye, Lu Liu
  • Patent number: 9404027
    Abstract: 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: Grant
    Filed: October 21, 2013
    Date of Patent: August 2, 2016
    Assignee: The Curators of the University of Missouri
    Inventor: Galen J. Suppes
  • Patent number: 9352304
    Abstract: 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: Grant
    Filed: November 4, 2010
    Date of Patent: May 31, 2016
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Tao Zhang, Zhijun Tai, Aiqin Wang, Mingyuan Zheng
  • Patent number: 9328045
    Abstract: 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: Grant
    Filed: January 9, 2014
    Date of Patent: May 3, 2016
    Assignee: SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
  • Patent number: 9302965
    Abstract: 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: Grant
    Filed: April 1, 2014
    Date of Patent: April 5, 2016
    Assignee: Shell Oil Company
    Inventors: Evert Van Der Heide, Govinda Subbanna Wagle
  • Patent number: 9284242
    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: Grant
    Filed: October 30, 2013
    Date of Patent: March 15, 2016
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Kimberly Ann Johnson, Glenn Charles Komplin, Edward James Denton
  • Patent number: 9221727
    Abstract: 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: Grant
    Filed: March 26, 2015
    Date of Patent: December 29, 2015
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Tin-Tack Peter Cheung, Zongxuan Hong
  • Patent number: 9174898
    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: Grant
    Filed: June 27, 2013
    Date of Patent: November 3, 2015
    Assignee: Shell Oil Company
    Inventors: Glenn Charles Komplin, Joseph Broun Powell
  • Patent number: 9132418
    Abstract: 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: Grant
    Filed: June 17, 2014
    Date of Patent: September 15, 2015
    Assignee: CLARIANT CORPORATION
    Inventors: Wenqin Shen, Franz G. Petzold, Karen Libby, Wayne Turbeville
  • Patent number: 9035109
    Abstract: 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: Grant
    Filed: May 29, 2014
    Date of Patent: May 19, 2015
    Assignee: Rennovia, Inc.
    Inventors: Eric L. Dias, James A. W. Shoemaker, Thomas R. Boussie, Vincent J. Murphy
  • Patent number: 9018423
    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: Grant
    Filed: April 25, 2013
    Date of Patent: April 28, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: 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
  • Patent number: 9012699
    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 9, 2014
    Date of Patent: April 21, 2015
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Publication number: 20150099903
    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: December 12, 2014
    Publication date: April 9, 2015
    Inventors: 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
  • Patent number: 9000041
    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: June 24, 2013
    Date of Patent: April 7, 2015
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Publication number: 20150094498
    Abstract: 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: Application
    Filed: December 3, 2014
    Publication date: April 2, 2015
    Applicant: BATTELLE MEMORIAL INSTITUTE
    Inventors: John G. Frye, Jr., Aaron A. Oberg, Alan H. Zacher
  • Publication number: 20150031923
    Abstract: 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: Application
    Filed: June 17, 2014
    Publication date: January 29, 2015
    Applicant: CLARIANT CORPORATION
    Inventors: Wenqin Shen, Franz G. Petzold, Karen Libby, Wayne Turbeville
  • Patent number: 8937202
    Abstract: 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: Grant
    Filed: February 23, 2010
    Date of Patent: January 20, 2015
    Assignee: Battelle Memorial Institute
    Inventors: John G. Frye, Aaron A. Oberg, Alan H. Zacher
  • Patent number: 8921616
    Abstract: 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: Grant
    Filed: January 12, 2012
    Date of Patent: December 30, 2014
    Assignees: Clariant Catalysts (Japan) K.K., National University Corporation Chiba University
    Inventors: Tetsuro Kizaki, Keizo Iwatani, Xin Chen, Satoshi Sato
  • Patent number: 8889585
    Abstract: 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: Grant
    Filed: October 22, 2010
    Date of Patent: November 18, 2014
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Tao Zhang, Yanhua Zhang, Aiqin Wang, Mingyuan Zheng
  • Patent number: 8877985
    Abstract: Methods and systems for co-producing higher hydrocarbons and glycols from bio-based feedstocks containing carbohydrates are disclosed.
    Type: Grant
    Filed: June 13, 2012
    Date of Patent: November 4, 2014
    Assignee: Shell Oil Company
    Inventor: Joseph Broun Powell
  • Patent number: 8877984
    Abstract: 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: Grant
    Filed: May 21, 2012
    Date of Patent: November 4, 2014
    Assignee: Eastman Chemical Company
    Inventors: Benjamin Fredrick Barton, Steven Leroy Cook, Jeff Scott Howell, Noah Glenn McMillan, Damon Bryan Shackelford, Brent Alan Tennant, Phillip Wayne Turner
  • Patent number: 8859826
    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: Grant
    Filed: April 25, 2013
    Date of Patent: October 14, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
  • Patent number: 8859828
    Abstract: 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: Grant
    Filed: March 3, 2010
    Date of Patent: October 14, 2014
    Assignee: Clariant Corporation
    Inventors: Aiguo Liu, Wayne Turbeville, Christopher C. Luckett, Hui Hui (Faye) Li
  • Patent number: 8853465
    Abstract: 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: Grant
    Filed: May 11, 2011
    Date of Patent: October 7, 2014
    Assignee: BASF SE
    Inventors: Michael Steiniger, Maria Guixa Guardia, Kai Stehmeier
  • Patent number: 8846984
    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: Grant
    Filed: April 25, 2013
    Date of Patent: September 30, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joseph E Murphy, Joachim C Ritter, Sourav Kumar Sengupta
  • Patent number: 8846985
    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: Grant
    Filed: April 25, 2013
    Date of Patent: September 30, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
  • Publication number: 20140249335
    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 9, 2014
    Publication date: September 4, 2014
    Applicant: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • 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: 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: 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: 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: 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: 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