By Reduction, Dehydration, Or Cleavage Patents (Class 568/903)
  • Patent number: 11780791
    Abstract: The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1).
    Type: Grant
    Filed: April 12, 2022
    Date of Patent: October 10, 2023
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuki Miyake, Takeshi Kinsho, Ryo Komatsu
  • Patent number: 11555153
    Abstract: A process for producing fuel-range organic oxygen-containing compounds is provided. The process includes converting glycerol in the presence of a metal oxide catalyst. The fuel-range organic oxygen-containing compounds can be deoxygenated to produce gasoline and jet fuels or fuel blending components.
    Type: Grant
    Filed: April 19, 2022
    Date of Patent: January 17, 2023
    Assignee: CHEVRON U.S.A. INC.
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 11180434
    Abstract: A continuous-flow process for the production of allyl compounds by deoxydehydration of glycerol includes: (a) Forming a reactive solution by mixing glycerol (1) with: a carboxylic acid (2), and/or a triethyl orthoester, preferably triethyl orthoformate (TEOF); (b) Feeding the reactive solution to an inlet of a channel of a thermolysis microreactor module wherein the channel has an inner hydraulic diameter, D=4 A/P, wherein A is the area and P the perimeter of a cross-section of the channel, of not more than 1000 ?m, (c) Exposing the reactive solution to thermolysis by driving a flow of the reactive solution along the channel from the inlet to an outlet, for a thermolysis time, t, at a pressure, P, and at a thermolysis temperature, T, larger than 200° C., to form thermolysis products including at least one allyl compound; and Recovering the thermolysis products at the outlet and separating the at least one allyl compound from the other thermolysis products.
    Type: Grant
    Filed: February 26, 2018
    Date of Patent: November 23, 2021
    Assignee: UNIVERSITE DE LIEGE
    Inventors: Jean-Christophe Monbaliu, Nelly Ntumba Tshibalonza
  • Patent number: 10654781
    Abstract: This invention provides a method for catalytic conversion of carbohydrates to low-carbon diols using alloy catalysts. In the process, carbohydrates as the feedstock are subjected to one-step catalytic conversion to realize the highly efficient and selective production of ethylene glycol etc. under hydrothermal conditions, with an alloy catalyst composed of tin, and a transition metal such as iron, cobalt, nickel, rhodium, ruthenium, palladium, iridium, platinum and copper, or a mixture thereof. The reaction is carried out in water at a temperature range of 120-300° C., with a hydrogen pressure range of 1-13 MPa. Compared with the present petroleum based synthesis technology of ethylene glycol, the method in this invention possesses advantages of using renewable feedstock, high atom economy and environmental friendly.
    Type: Grant
    Filed: November 26, 2015
    Date of Patent: May 19, 2020
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Ruiyan Sun, Mingyuan Zheng, Tao Zhang, Jifeng Pang, Yu Jiang, Aiqin Wang, Xiaodong Wang
  • Patent number: 10201804
    Abstract: Catalytic materials for exhaust gas purifying catalyst composites comprise platinum group metal (PGM)-containing catalysts whose PGM component(s) are provided as nanoparticles and are affixed to a refractory metal oxide, which may be provided as a precursor. Upon calcination of the catalysts, the PGM is thermally affixed to and well-dispersed throughout the support. Excellent conversion of hydrocarbons and nitrogen oxides can advantageously be achieved using such catalysts.
    Type: Grant
    Filed: January 29, 2016
    Date of Patent: February 12, 2019
    Assignees: BASF Corporation, Georgia Tech Research Corporation
    Inventors: Andrey Karpov, David Preli, Knut Wassermann, Andreas Sundermann, Sang-IL Choi, Ping Lu, Younan Xia
  • Patent number: 9862664
    Abstract: Process for the production of alkenols comprising the dehydration of at least one diol in the presence of at least one catalyst based on cerium oxide, wherein said catalyst based on cerium oxide is obtained by precipitation, in the presence of at least one base, of at least one compound containing cerium. Preferably, said diol may be a butanediol, more preferably 1,3-butanediol, still more preferably bio-1,3-butanediol derived from biosynthetic processes. Said alkenols may advantageously be used for the production of 1,3-butadiene, in particular of bio-1,3-butadiene.
    Type: Grant
    Filed: May 15, 2015
    Date of Patent: January 9, 2018
    Assignee: Versalis S.p.A.
    Inventors: Alberto Cesana, Stefano Ramello, Guido Spano′
  • Patent number: 9517984
    Abstract: Embodiments of an integrated method for step-wise conversion of 2,3-butanediol to 2-butanol, and optionally to hydrocarbons, are disclosed. The method includes providing an acidic catalyst, exposing a composition comprising aqueous 2,3-butanediol to the acidic catalyst to produce an intermediate composition comprising methyl ethyl ketone, providing a hydrogenation catalyst that is spatially separated from the acidic catalyst, and subsequently exposing the intermediate composition to the hydrogenation catalyst to produce a composition comprising 2-butanol. The method may further include subsequently exposing the composition comprising 2-butanol to a deoxygenation catalyst, and deoxygenating the 2-butanol to form hydrocarbons. In some embodiments, the hydrocarbons comprise olefins, such as butenes, and the method may further include subsequently exposing the hydrocarbons to a hydrogenation catalyst to form saturated hydrocarbons.
    Type: Grant
    Filed: April 3, 2015
    Date of Patent: December 13, 2016
    Assignee: Battelle Memorial Institute
    Inventors: Michael A. Lilga, Guo-Shuh Lee, Suh-Jane Lee
  • Patent number: 9452963
    Abstract: Disclosed is a method for producing 1,3-butadiene and/or 3-buten-2-ol from 2,3-butanediol with high selectivity without using a radioactive substance. The method for producing 1,3-butadiene and/or 3-buten-2-ol comprises the step of dehydrating 2,3-butanediol in the presence of scandium oxide. The method enables the production of 1,3-butadiene and/or 3-buten-2-ol from 2,3-butanediol with high selectivity without using a radioactive substance.
    Type: Grant
    Filed: September 8, 2014
    Date of Patent: September 27, 2016
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Satoshi Sakami, Katsushige Yamada, Satoshi Sato, Hailing Duan
  • Patent number: 9302966
    Abstract: A process for converting polyhydric alcohols to monoalcohols in a counter current column reactor with a metal based catalyst supported on a porous membrane coated over a tubular system that delivers hydrogen where a hydrocarbon (low polarity) liquid solvent is fed at the bottom of the column reactor and an aqueous liquid having polyhydric alcohols therein is fed into the top of the reactor such that the aqueous liquid flows countercurrent to the low polarity solvent liquid and further wherein the low polarity solvent liquid is less dense than the aqueous liquid such that the two liquids are subject to phase separation. Monoalcohols are formed by hydrogenolysis reactions of polyhydric alcohols on the metal catalyst. Monoalcohols phase separate from the aqueous phase to the hydrocarbon solvent. Monoalcohols are further separated from the organic solvent.
    Type: Grant
    Filed: June 25, 2015
    Date of Patent: April 5, 2016
    Assignee: PHILLIPS 66 COMPANY
    Inventors: Lotero Edgar, Fjare A. Kristi, Sughrue L. Edward
  • Patent number: 9283549
    Abstract: The present invention is related to a new metal powder catalytic system (catalyst) comprising a cobalt/chrome-alloy as a carrier, its production and its use in hydrogenation processes.
    Type: Grant
    Filed: February 22, 2013
    Date of Patent: March 15, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Axel Buss
  • Patent number: 9180434
    Abstract: The present invention relates to a structured catalyst based on sintered metal fibers (SMF) coated by a non-acidic metal oxide layer impregnated with Pd and Agnanopartides, characterized in that the ratio of the Pd:Ag is 1:1 to 10:1, as well as the use of such a catalyst in selective catalytic hydrogenations of organic compounds.
    Type: Grant
    Filed: October 26, 2012
    Date of Patent: November 10, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Lioubov Kiwi-Minsker, Igor Iouranov
  • Patent number: 9102584
    Abstract: A method of hydrothermal hydrocatalytic treating biomass is provided. Lignocellulosic biomass solids is provided to a hydrothermal digestion unit in the presence of a digestive solvent, and a supported hydrogenolysis catalyst containing (a) sulfur, (b) Mo or W, and (c) Co, Ni or mixture thereof, incorporated into a group 4 metal oxide support; (ii) heating the lignocellulosic biomass solids and digestive solvent in the presence of hydrogen, and the supported hydrogenolysis catalyst thereby forming a product solution containing plurality of oxygenated hydrocarbons, said catalyst retaining a crush strength of at least 50% after being subjected to an aqueous phase stability test compared with before the aqueous phase stability test or a crush strength of at least 0.25 kg after being subjected to an aqueous phase stability test.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: August 11, 2015
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Glenn Charles Komplin, John Anthony Smegal, Kimberly Ann Johnson
  • Patent number: 8946489
    Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy or sugary materials, to produce ethanol and/or butanol, e.g., by fermentation.
    Type: Grant
    Filed: March 17, 2014
    Date of Patent: February 3, 2015
    Assignee: Xyleco, Inc.
    Inventor: Marshall Medoff
  • Patent number: 8933279
    Abstract: A method for preparing a mixture (M) comprising at least an alcohol (Aj), said method comprising the following steps: i) a step in which at least an alcohol (Ai) in gaseous state is oligomerized, thereby producing a mixture (A); ii) a step in which the mixture (A) is condensed to a gaseous stream and to a liquid stream corresponding to a condensed mixture (A); and iii) a step in which the condensed mixture (A) is hydrogenated in the liquid state.
    Type: Grant
    Filed: October 2, 2012
    Date of Patent: January 13, 2015
    Assignee: Rhodia Operations
    Inventors: Didier Morvan, Loic Baussaron, Gerald Bocquenet, Roland Jacquot, Philippe Marion, Virginie Belliere-Baca
  • Publication number: 20140343323
    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: Application
    Filed: May 29, 2014
    Publication date: November 20, 2014
    Applicant: RENNOVIA, INC.
    Inventors: Eric L. DIAS, James A. W. SHOEMAKER, Thomas R. BOUSSIE, Vincent J. MURPHY
  • Publication number: 20140323774
    Abstract: A method of making one or more alcohols with a single hydroxy group, such as methanol and ethanol, the method comprising contacting a polyol and water with a basic catalyst. The polyol may be glycerol, for example. The '. catalyst may be magnesium oxide.
    Type: Application
    Filed: August 9, 2012
    Publication date: October 30, 2014
    Applicant: UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED
    Inventors: Graham John Hutchings, Muhammad Hasnain Haider, Nicholas Francois Dummer, Stuart Hamilton Taylor, David Willliam Knight
  • 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: 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
  • Publication number: 20140288335
    Abstract: The present invention provides a hydrocracking catalyst obtainable by mixing a metal compound (A) including any one metal of Groups 3 to 11 of the Periodic Table, a compound (B) including at least one compound selected from the group consisting of a ruthenium oxide compound (B1) and a high-valence compound (B2) including any metal of Groups 8 to 11 of the Periodic Table, and a metal oxide (C) including a metal of Group 5, Group 6 or Group 7 of the Periodic Table, and conducting reduction treatment.
    Type: Application
    Filed: August 22, 2012
    Publication date: September 25, 2014
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Kiyotaka Yoshii, Atsushi Yamada
  • Publication number: 20140275584
    Abstract: Methods, catalysts, and reactor systems for producing in high yield aromatic chemicals and liquid fuels from a mixture of oxygenates comprising di- and polyoxygenates are disclosed. Also disclosed are methods, catalysts, and reactor systems for producing aromatic chemicals and liquid fuels from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like; and methods, catalysts, and reactor systems for producing the mixture of oxygenates from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like. The disclosed catalysts for preparing the mixture of oxygenates comprise a NinSnm alloy and a crystalline alumina support.
    Type: Application
    Filed: March 14, 2014
    Publication date: September 18, 2014
    Applicant: Virent, Inc.
    Inventors: Taylor Beck, Brian Blank, Casey Jones, Elizabeth Woods, Randy Cortright
  • Patent number: 8779216
    Abstract: The invention relates to a method for the dimerization of alcohols in the context of a Guerbet reaction, in which one or more alcohols (A) having 2 to 72 C atoms and 1 to 3 OH groups per molecule are reacted in the presence of (a) a base (B), (b) a carbonyl compound (C), and (c) a hydrogenation catalyst (H) from the group of metals ruthenium, rhodium, palladium, osmium, iridium, and platinum, said metals being in the elementary form, with the proviso that the alcohols (A) have at least one primary or secondary OH group, and that a C atom that carries at least one H atom as a substituent is directly adjacent to the C atom with said primary or secondary OH group.
    Type: Grant
    Filed: October 28, 2010
    Date of Patent: July 15, 2014
    Assignee: Cognis IP Management GmbH
    Inventors: Anja Wick, Eike Ulf Mahnke
  • Patent number: 8759593
    Abstract: A method of reclaiming alcohols from purification residue includes hydrolyzing a purification residue with an aqueous medium in the presence of (i) an acid and (ii) an oxidizing agent.
    Type: Grant
    Filed: September 17, 2012
    Date of Patent: June 24, 2014
    Assignee: Oxea Bishop LLC
    Inventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
  • Publication number: 20140171694
    Abstract: A method of hydrothermal hydrocatalytic treating biomass is provided. Lignocellulosic biomass solids is provided to a hydrothermal digestion unit in the presence of a digestive solvent, and a supported hydrogenolysis catalyst containing (a) sulfur, (b) Mo or W, and (c) Co, Ni or mixture thereof, incorporated into a group 4 metal oxide support; (ii) heating the lignocellulosic biomass solids and digestive solvent in the presence of hydrogen, and the supported hydrogenolysis catalyst thereby forming a product solution containing plurality of oxygenated hydrocarbons, said catalyst retaining a crush strength of at least 50% after being subjected to an aqueous phase stability test compared with before the aqueous phase stability test or a crush strength of at least 0.25 kg after being subjected to an aqueous phase stability test.
    Type: Application
    Filed: December 19, 2013
    Publication date: June 19, 2014
    Applicant: Shell Oil Company
    Inventors: Joseph Broun POWELL, Glenn Charles KOMPLIN, John Anthony SMEGAL, Kimberly Ann JOHNSON
  • Publication number: 20140148330
    Abstract: Semi-permeable particle can be used to facilitate chemical reactions. The semi-permeable particles are permeable to molecules having a molar mass of 1000 Daltons or less, have a mode particle size of at least 1 ?m, and comprise nanoparticles of catalytically active metallic materials disposed within at least some of multiple discrete cavities in the continuous polymeric phase. The nanoparticles of catalytically active metallic materials (a) comprise one or more elements selected from Groups 8, 9, 10, and 11 of the Periodic Table, and (b) have an effective diameter of at least 1 nm and up to and including 200 nm.
    Type: Application
    Filed: November 28, 2012
    Publication date: May 29, 2014
    Inventors: Douglas R. Robello, Mridula Nair, Mark R. Mis, Matthew Dirmyer
  • Patent number: 8716537
    Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy or sugary materials, to produce ethanol and/or butanol, e.g., by fermentation.
    Type: Grant
    Filed: October 22, 2012
    Date of Patent: May 6, 2014
    Assignee: Xyleco, Inc.
    Inventor: Marshall Medoff
  • Publication number: 20140121423
    Abstract: Hydrothermal digestion of cellulosic biomass solids in a glycerol solvent system can convert both the cellulosic biomass solids and the glycerol into a glycol reaction product for subsequent processing without the need for further solvent separation. Methods for digesting cellulosic biomass solids in a glycerol solvent system can comprise: providing cellulosic biomass solids and a slurry catalyst in a hydrothermal digestion unit, the slurry catalyst being capable of activating molecular hydrogen; heating the cellulosic biomass solids in the hydrothermal digestion unit in the presence of the slurry catalyst, molecular hydrogen, and a solvent system comprising glycerol, thereby forming soluble carbohydrates; and at least partially converting the soluble carbohydrates and the glycerol into a reaction product comprising a glycol within the hydrothermal digestion unit.
    Type: Application
    Filed: October 30, 2013
    Publication date: May 1, 2014
    Applicant: SHELL OIL COMPANY
    Inventors: Joseph Broun POWELL, Kimberly Ann JOHSON
  • Patent number: 8710281
    Abstract: Disclosed are methods for producing polyols, ketones, carboxylic acids, aldehydes and alcohols from biomass-derived oxygenated hydrocarbons, such as sugars, sugar alcohols, saccharides and the like, using catalysts containing platinum, ruthenium and tin. The methods can be run at lower temperatures and pressures, and allows for the production of oxygenated compounds without the need for hydrogen from an external source. The oxygenated compounds produced are useful as industrial chemicals or chemical intermediates for liquid fuels production.
    Type: Grant
    Filed: December 29, 2010
    Date of Patent: April 29, 2014
    Assignee: Virent, Inc.
    Inventors: Dick Alan Nagaki, Randy D. Cortright, Lisa Kamke, Elizabeth Woods
  • Publication number: 20140051872
    Abstract: The present invention provides catalysts, methods, and reactor systems for converting oxygenated hydrocarbons to oxygenated compounds. The invention includes methods for producing cyclic ethers, monooxygenates, dioxygenates, ketones, aldehydes, carboxylic acids, and alcohols from oxygenated hydrocarbons, such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like, using catalysts containing palladium, molybdenum, tin, and tungsten. The oxygenated compounds produced are useful in the production of liquid fuels, chemicals, and other products.
    Type: Application
    Filed: August 15, 2012
    Publication date: February 20, 2014
    Applicant: Virent, Inc.
    Inventors: Brian Blank, Randy Cortright, Taylor Beck, Elizabeth Woods, Mike Jehring
  • Patent number: 8629306
    Abstract: The invention relates to a process for preparing 1,6-hexanediol, preferably with at least 99.5% purity, which are especially virtually free of 1,4-cyclohexanediols, from a carboxylic acid mixture which is obtained as a by-product of the catalytic oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-comprising gases and by water extraction of the reaction mixture, by hydrogenating the carboxylic acid mixture, esterifying and hydrogenating a substream to hexanediol.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: January 14, 2014
    Assignee: BASF SE
    Inventors: Rolf Pinkos, Daniel Breuninger, Gerd-Dieter Tebben
  • Publication number: 20140005444
    Abstract: Digesting cellulosic biomass solids in the presence of a well-distributed slurry catalyst capable of activating molecular hydrogen may limit the amount of degradation products that form during digestion.
    Type: Application
    Filed: June 27, 2013
    Publication date: January 2, 2014
    Inventors: Glenn Charles KOMPLIN, Joseph Broun POWELL
  • Publication number: 20140005445
    Abstract: Digesting cellulosic biomass in the presence of a slurry catalyst may reduce degradation product formation, but catalyst distribution and retention can be problematic. Digestion methods can comprise: providing cellulosic biomass solids and a slurry catalyst capable of activating molecular hydrogen in a digestion unit; providing a digestible filter aid in the digestion unit; distributing the slurry catalyst within the cellulosic biomass solids using fluid flow; retaining at least a portion of the slurry catalyst in a fixed location using the digestible filter aid; heating the cellulosic biomass solids in the presence of the slurry catalyst, a digestion solvent, and molecular hydrogen, thereby forming a liquor phase comprising soluble carbohydrates; and performing a catalytic reduction reaction on the soluble carbohydrates within the digestion unit, thereby at least partially forming a reaction product comprising a triol, a diol, a monohydric alcohol, or any combination thereof in the digestion unit.
    Type: Application
    Filed: June 27, 2013
    Publication date: January 2, 2014
    Inventors: Glenn Charles KOMPLIN, Joseph Broun KOMPLIN
  • Patent number: 8603201
    Abstract: The present invention is to provide a novel method for manufacturing various organic compounds from two or more kinds of alcohol, or one kind of alcohol having three or more carbon atoms. It is a method for synthesizing one kind of, or two or more kinds of organic compounds comprising allowing two or more kinds of alcohol or one kind of alcohol having three or more carbon atoms to contact a calcium phosphate catalyst such as hydroxyapatite, or hydrotalcite.
    Type: Grant
    Filed: February 23, 2009
    Date of Patent: December 10, 2013
    Assignee: Kabushiki Kaisha Sangi
    Inventors: Takashi Tsuchida, Shuji Sakuma, Tetsuya Yoshioka, Jun Kubo
  • Patent number: 8592636
    Abstract: The present invention relates to a process of reacting specific compounds, which are defined below with hydrogen in the presence of a structured catalyst based on sintered metal fibers (SMF) coated by a ZnO layer with Pd-nanoparticles, to reactions of these specific 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: Grant
    Filed: January 28, 2011
    Date of Patent: November 26, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Thomas Mueller, Lioubov Kiwi-Minsker, Albert Renken, Igor Iouranov
  • Publication number: 20130225879
    Abstract: Process for the preparation of a product alcohol mixture comprising the steps of: (a) providing a synthesis gas comprising carbon monoxide and hydrogen (b) providing an amount of methanol and a second source alcohol Rn—CH2—CH2—OH comprising n+2 carbon atoms (Rn?CnH2n+1, n?O) to the synthesis gas to obtain a selective alcohol synthesis mixture (c) converting the selective synthesis mixture in presence of one or more catalysts catalysing the conversion of the synthesis gas mixture into a product alcohol mixture in which the initially dominating alcohol is a preferred Cn+3 alcohol having the structure Rn—CH(CH3)—CH2—OH (d) withdrawing the product alcohol mixture of step (c).
    Type: Application
    Filed: November 8, 2010
    Publication date: August 29, 2013
    Inventors: Burcin Temel, Poul Erik Højlund Nielsen, Pablo Beato
  • Publication number: 20130217923
    Abstract: The present invention relates to novel structured catalysts based on sintered metal fibers (SMF) coated by a basic oxide layer with Pd-nanoparticles, to reactions of organic compounds with hydrogen in the presence of said catalyst and an organic base as well as to vitamins, carotinoids, perfume ingredients, and/or food or feed ingredients prepared by using this reaction.
    Type: Application
    Filed: July 1, 2011
    Publication date: August 22, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Lioubov Kiwi-Minsker, Igor Iouranov
  • Patent number: 8513472
    Abstract: There is provided a process for preparing 1,6-hexanediol by esterifying a carboxylic acid mixture resulted from oxidation of cyclohexane with oxygen, and then hydrogenating the esters, which substantially does not contain a compound leading to a high ester value.
    Type: Grant
    Filed: October 19, 2009
    Date of Patent: August 20, 2013
    Assignee: Ube Industries, Ltd.
    Inventors: Hirofumi Li, Tomoyuki Itou, Yoshiki Kawamura, Toshiyuki Matsushita
  • Patent number: 8507736
    Abstract: A method of producing short chain alcohols from glycerol generated as a byproduct of biodiesel production is provided.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: August 13, 2013
    Assignee: BioFuel-Solution i Malmo AB
    Inventors: Christian Hulteberg, Jan Brandin, Richard R. Woods, Brook Porter
  • Publication number: 20130072722
    Abstract: The present invention relates to supported metal catalysts, wherein the catalysts are modified by at least one amine, a method for the preparation thereof and hydrogenation processes utilising the supported metal catalysts.
    Type: Application
    Filed: February 17, 2011
    Publication date: March 21, 2013
    Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
    Inventors: Peter Trenton Bishop, James Cookson, Frederick Earnest Hancock, Steven Hawker, Robert John McNair
  • Publication number: 20130060067
    Abstract: Methods of converting cellulose or related biorenewable carbohydrate materials into high-value chemical compounds. The methods provide a means of converting low-cost materials such as cellulose and biomass into high yields of compounds such as ethylene glycol, propylene glycol, glycerin, methanol, hydroxyacetone, glycolaldehyde and dihydroxyacetone.
    Type: Application
    Filed: August 24, 2012
    Publication date: March 7, 2013
    Applicant: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
    Inventors: Walter S. Trahanovsky, Ronald C. Holtan, Kyle W. Quasdorf, Norman K. Olson, Alyse A. Dilts, Joseph A. Marshall
  • Patent number: 8304585
    Abstract: A method is provided for producing highly pure 1,6-hexanediol in which the contents of impurities such as 1,4-cyclohexanediol, 1,5-hexanediol, 1,2-cyclohexanediol, 1,7-pentanediol, 1,5-pentanediol and high boiling point components are significantly reduced.
    Type: Grant
    Filed: January 12, 2007
    Date of Patent: November 6, 2012
    Assignee: Ube Industries, Ltd.
    Inventors: Hirofumi Ii, Tomoyuki Ito, Yoshiki Kawamura, Toshiyuki Matsushita
  • Patent number: 8293952
    Abstract: The present invention provides pyrolysis products that have greater stability than pyrolysis products obtained from conventional pyrolysis production processes. The invention involves pyrolyzing a hydrocarbon feedstock in the presence of a basic metal oxide catalyst to produce a pyrolysis product. The pyrolysis product of the present invention can advantageously be particularly high in alcohol content.
    Type: Grant
    Filed: March 30, 2011
    Date of Patent: October 23, 2012
    Assignee: ExxonMobil Research and Engineering Company
    Inventor: Doron Levin
  • Patent number: 8252963
    Abstract: A catalyst composition can include: a support; a ruthenium catalyst (Ru) nanoparticle; and a linker linking the Ru nanoparticle to the support, wherein the linker is stable under hydrogenolysis conditions. In one aspect, the linker can include 3-aminopropyl trimethoxysilane (APTS) or derivatives thereof, such as those with amine functionality. In another aspect, the linker can include phosphotungstic acid (PTA) or other similar solid acid agents. In another aspect, the support can be selected from alumina, carbon, silica, a zeolite, TiO2, ZrO2, or another suitable material. A specific example of a support includes zeolite, such as a NaY zeolite. The Ru nanoparticle can have a size range from about 1 nm to about 25 nm, and can be obtained by reduction of Ru salts.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: August 28, 2012
    Assignee: University of Kansas
    Inventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
  • Patent number: 8227648
    Abstract: Systems and processes for dehydration of a process stream in the production of motor fuel grade ethanol (MFGE) can include temperature controlled adsorption of water in the process stream, and heat pumping to transfer heat from the process stream to a heat sink using one or more stages of heat pumping. One stage of heat pumping can be achieved during the regeneration process of a temperature controlled adsorber by desorbing the adsorbed water at a thermal condition enabling useful heat recovery. Another stage of heat pumping can be achieved during the adsorption process of a temperature controlled adsorber by transferring the heat of water adsorption to a heat sink. The heat sink with respect to each stage of heat pumping can be a solids separation unit, such as a beer column.
    Type: Grant
    Filed: September 8, 2009
    Date of Patent: July 24, 2012
    Assignee: UOP LLC
    Inventors: David A. Wegerer, Stephen R. Dunne
  • Patent number: 8212087
    Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy or sugary materials, to produce ethanol and/or butanol, e.g., by fermentation.
    Type: Grant
    Filed: April 3, 2009
    Date of Patent: July 3, 2012
    Assignee: Xyleco, Inc.
    Inventor: Marshall Medoff
  • Patent number: 8143460
    Abstract: A method comprising applying a controlled flow cavitation apparatus to an alcohol production process in order to increase alcohol yield. A grain-based liquid medium comprising grain and a liquid carrier can be passed through a controlled flow cavitation apparatus at a velocity capable of generating a hydrodynamic cavitation zone where the grain size can be reduced. One or more controlled flow cavitation apparatuses can be applied at various points of an alcohol production process, such as a starch-to-ethanol production process.
    Type: Grant
    Filed: January 13, 2010
    Date of Patent: March 27, 2012
    Assignee: Arisdyne Systems, Inc.
    Inventor: Oleg Kozyuk
  • Patent number: 8119844
    Abstract: The invention relates to methods for the production of alcohols by microbial fermentation, particularly microbial fermentation of substrates comprising glycerol and/or acetate, to butanol.
    Type: Grant
    Filed: April 23, 2009
    Date of Patent: February 21, 2012
    Assignee: LanzaTech New Zealand Limited
    Inventors: Richard Llewellyn Sydney Forster, Sean Dennis Simpson, Christophe Collet
  • Publication number: 20120022299
    Abstract: A process to integrate a first biofuels process and a second generation cellulosic biofuels process is provided. The pyrolysis means which produces the char stream and a bioliquid stream. The low pressure hydrotreating component, a high pressure hydrotreating component, the low pressure hydrotreating component which produces the hydrocarbon stream, the high pressure hydrotreating component which produces the steam stream and bioliquid stream. A distillation means, which produces a green gasoline stream and a green diesel stream from the bioliquid stream. The second biofuels process may be a first generation bio-ethanol process, which produces a bio-ethanol stream. The hydrogen production unit, which produces the hydrogen stream and the steam stream. The hydrogen production unit may be a steam reformer or partial oxidation unit.
    Type: Application
    Filed: July 21, 2010
    Publication date: January 26, 2012
    Applicant: Air Liquide Large Industries U.S. LP
    Inventor: Dennis A. Vauk
  • Publication number: 20110319672
    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: Application
    Filed: March 3, 2010
    Publication date: December 29, 2011
    Applicant: SUD-CHEMIE INC.
    Inventors: Aiguo Liu, Wayne Turbeville, Christopher C. Luckett, Hui Hui (Faye) Li
  • Patent number: 8067646
    Abstract: Systems and processes for dehydration of a process stream in the production of motor fuel grade ethanol (MFGE) can include temperature controlled adsorption of water in the process stream, and heat pumping of the associated heat of adsorption. The process can include providing a process stream (110) including ethanol and water to a first temperature controlled adsorber (102) where water is removed by adsorption to produce an MFGE product stream (114) and an associated heat of adsorption. A cooling fluid can be provided to the first temperature controlled adsorber (102) to remove heat of adsorption and produce a heated cooling fluid (120). Heat from the heated cooling fluid can be provided to a heat sink.
    Type: Grant
    Filed: December 17, 2008
    Date of Patent: November 29, 2011
    Assignee: UOP LLC
    Inventors: David A. Wegerer, Stephen R. Dunne
  • Publication number: 20110218364
    Abstract: An intermetallic magnetic compound of iron oxide and palladium with a nanometer particle size is disclosed, together with a method of making magnetic nanoparticles that include an intermetallic bond between palladium and iron-oxide. Additionally, a method is disclosed of catalyzing an organic reaction by contacting the organic reagents with an intermetallic magnetic compound of iron oxide and palladium that has nanometer particle size in an amount sufficient to catalyze the organic reaction.
    Type: Application
    Filed: March 5, 2010
    Publication date: September 8, 2011
    Applicant: CEM CORPORATION
    Inventors: Keith A. Porter, E. Keller Barnhardt