Catalyst Utilized Patents (Class 568/881)
  • Patent number: 11133504
    Abstract: A nickel complex oxide having a carbon content of 0.15% by mass or lower.
    Type: Grant
    Filed: October 25, 2018
    Date of Patent: September 28, 2021
    Assignee: SUMITOMO METAL MINING CO., LTD.
    Inventors: Yuji Kawakami, Tomomichi Nihei
  • Patent number: 10865170
    Abstract: A process is disclosed for selectively producing 2-butanol from GVL by using at least one transition metal catalyst selected from the group consisting of iron, ruthenium, cobalt, rhodium and iridium.
    Type: Grant
    Filed: July 11, 2019
    Date of Patent: December 15, 2020
    Assignee: NESTE OYJ
    Inventors: Marina Lindblad, Mats Käldström, Susanna Wallenius, Kaisa Lamminpää
  • Patent number: 10745330
    Abstract: A method and catalyst for forming higher alcohols from lower alcohol feedstocks. In one application a highly selective and stable copper pseudo-single-atom supported on MgO—Al2O3 catalyst is provided which provides ethanol condensation to higher alcohols at ˜50% yields and ˜85% selectivity is demonstrated with stable catalyst lifetime over 500 hours in a continuous flow system. In some applications a Guerbet condensation process is further utilized to yield a higher alcohol at a selectivity of near ˜90%.
    Type: Grant
    Filed: July 26, 2018
    Date of Patent: August 18, 2020
    Assignee: BATTELLE MEMORIAL INSTITUTE
    Inventors: Karthikeyan K. Ramasamy, Mond F. Guo, Michel J. Gray, Senthil Subramaniam
  • Patent number: 10717692
    Abstract: A process for the production of 2-alkylalkanol from an aldehyde is disclosed.
    Type: Grant
    Filed: October 12, 2017
    Date of Patent: July 21, 2020
    Assignee: Johnson Matthey Davy Technologies Limited
    Inventors: Adrian Lord, Martin Smidt
  • Patent number: 9822048
    Abstract: A method of extending the catalyst life of a hydrogenolysis catalyst activity in the presence of biomass and aqueous solution is described. Lignocellulosic biomass solids and aqueous solution is provided to in 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 solid metal oxide support. The lignocellulosic biomass solids in the hydrothermal digestion unit is heated to a temperature in the range of 180° C. to less than 300° C. in the presence of digestive solvent, hydrogen, and in the range of 0.15 wt. % to 12.5 wt. %, based on catalyst, of H2S or H2S source at least partially soluble in aqueous solution, and the supported hydrogenolysis catalyst forming a product solution containing plurality of oxygenated hydrocarbons, the hydrothermal digestion unit maintaining protective sulfur concentration.
    Type: Grant
    Filed: December 14, 2016
    Date of Patent: November 21, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Andries Quirin Maria Boon, Joseph Broun Powell
  • Patent number: 9656932
    Abstract: In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.
    Type: Grant
    Filed: May 12, 2015
    Date of Patent: May 23, 2017
    Assignee: PIONEER ENERGY
    Inventors: John T. Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
  • Patent number: 9611186
    Abstract: In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.
    Type: Grant
    Filed: November 8, 2012
    Date of Patent: April 4, 2017
    Assignee: PIONEER ENERGY
    Inventors: John Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
  • Patent number: 9593054
    Abstract: The present invention provides methods, reactor systems and catalysts for converting biomass and biomass-derived feedstocks to C8+ hydrocarbons using heterogenous catalysts. The product stream may be separated and further processed for use in chemical applications, or as a neat fuel or a blending component in jet fuel and diesel fuel, or as heavy oils for lubricant and/or fuel oil applications.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: March 14, 2017
    Assignee: Virent, Inc.
    Inventors: John Kania, Paul Blommel, Elizabeth Woods, Brice Dally, Warren Lyman, Randy Cortright
  • Patent number: 9567276
    Abstract: The invention relates to a process for the preparation of alcohols by hydrogenation of aldehydes, in which use mixture comprising at least one aldehyde and at least one accompanying component is brought into contact, in the presence of hydrogen, with a heterogeneous catalyst, giving a product mixture which comprises at least the alcohol corresponding to the hydrogenated aldehyde, and at least one by-product, where the catalyst comprises a support material, and nickel and copper applied thereto. The invention also includes a chromium-free catalyst suitable for hydrogenating aldehyde mixtures with different chain lengths, in particular those which originate from different hydroformylations and can also comprise substances with C?C double bonds.
    Type: Grant
    Filed: December 22, 2015
    Date of Patent: February 14, 2017
    Assignee: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Robert Franke, Marc Becker, Thomas Quandt, Frank Geilen
  • Patent number: 9388351
    Abstract: Furfural is produced through hydrolysis of the hemi-cellulose in corn stover. Furfural may also be produced from other biomass. The direct conversion of furfural to mono-alcohols which can be blended with gasoline is an attractive chemical process for providing biomass into the liquid fuel supply. Examples of such alcohols include 1-butanol, 1-pentanol, 2-pentanol and tetrahydrofurfuryl alcohol. Preferred alcohols include C-4 and C-5 mono-alcohols that have suitable blending properties.
    Type: Grant
    Filed: June 16, 2015
    Date of Patent: July 12, 2016
    Assignee: PHILLIPS 66 COMPANY
    Inventors: Yun Bao, Kristi A. Fjare, Edward L. Sughrue, TiePan Shi, Brian C. Dunn, Edgar Lotero
  • Patent number: 9144797
    Abstract: A process for regenerating catalysts that have been deactivated or poisoned during hydrogenation of biomass, sugars and polysaccharides is described, in which polymerized species that have agglomerated to catalyst surfaces can be removed by means of washing the catalyst with hot water at subcritical temperatures. A feature of the process regenerates the catalysts in situ, which allows the process to be adapted for used in continuous throughput reactor systems. Also described is a continuous hydrogenation process that incorporated the present regeneration process.
    Type: Grant
    Filed: April 17, 2013
    Date of Patent: September 29, 2015
    Assignee: Archer Daniels Midland Co.
    Inventor: Chi-Cheng Ma
  • Patent number: 9040757
    Abstract: In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: May 26, 2015
    Assignee: PIONEER ENERGY
    Inventors: John Henri, Jan Zygmunt, Mark Bergren, Robert Zubrin
  • Publication number: 20150141704
    Abstract: A method for the production of aliphatic alcohols and/or their ethers, comprising the step of reacting a substrate of the general formula (I): in which m is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9 and n is 1 or 2; R1 is hydrogen, a linear, branched or cyclic alkyl rest, a primary alkanol rest, an aryl rest or one of the following radicals: and R2 is hydrogen or —CH2OH; with hydrogen in the presence of a hydrogenation catalyst system, wherein the hydrogenation catalyst system comprises: a hydrogenation catalyst comprising Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and/or Pt; and an acidic additive selected from the group of organoperfluorocarboxylic acids, hydrochloric acid, formic acid, acetic acid, phosphoric acid, sulfuric acid, sulfonic acid and/or organic compounds comprising sulfonic acid groups, phosphoric acid groups and/or phosphonic acid groups; with the proviso that the acidic additive is a liquid and/or at least partially dissolved in the substrate (I) during the reaction of (I) with hydrogen in the case that R2 is
    Type: Application
    Filed: March 28, 2013
    Publication date: May 21, 2015
    Inventors: Walter Leitner, Jennifer Julis
  • Patent number: 9024089
    Abstract: Disclosed herein are processes for alcohol production by reducing an esterification product, such as ethyl acetate. The processes comprise esterifying acetic acid and an alcohol such as ethanol to produce an esterification product. The esterification product may be recovered using an extractive separation. The esterification product is reduced with hydrogen in the presence of a catalyst to obtain a crude reaction mixture comprising the alcohol, in particular ethanol, which may be separated from the crude reaction mixture.
    Type: Grant
    Filed: November 18, 2011
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Wei Qi, Tatiana H. Sonnenberg
  • Patent number: 9023299
    Abstract: A liquid/gas reactor includes a bulk catalyst bed and means for supplying fresh feed and recycled at least partially converted liquid product stream to the bulk catalyst bed. The reactor also includes means for collecting an at least partially converted liquid product stream from the bulk catalyst bed and recycling at least a portion thereto. A minor catalyst bed extends substantially vertically through the bulk catalyst bed. Means for supplying recycled at least partially converted product stream only to the minor catalyst bed is also provided. A separating wall is disposed between the bulk catalyst bed and the minor catalyst bed.
    Type: Grant
    Filed: January 12, 2012
    Date of Patent: May 5, 2015
    Assignee: Davy Process Technology Limited
    Inventors: Edward Adrian Lord, Arthur James Reason
  • Patent number: 9018427
    Abstract: A reactive distillation method comprises introducing a feed stream to a reactive distillation column, contacting the feed stream with one or more catalysts in the reactive distillation column during a distillation, and removing one or more higher alcohols during the distillation from the reactive distillation column as a bottoms stream. The feed stream comprises one or more alpha hydrogen alcohols, and the feed stream reacts in the presence of the one or more catalysts to produce a reaction product comprising the one or more higher alcohols.
    Type: Grant
    Filed: February 18, 2014
    Date of Patent: April 28, 2015
    Assignee: Greenyug, LLC
    Inventors: Sagar B. Gadewar, Brian Christopher Vicente, Peter K. Stoimenov, Vivek Julka
  • Patent number: 9000232
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. The column yields a first residue that comprises ethanol, ethyl acetate, acetic acid, and water. The first residue is separated in a second column to yield a second distillate comprising ethanol and ethyl acetate. The second distillate is then separated in a third column to yield a third distillate comprising ethyl acetate and a third residue comprising ethanol.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: April 7, 2015
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Victor J. Johnston, David Lee, Adam Orosco
  • Patent number: 9000235
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. The column yields a residue that comprises ethanol, acetic acid, and the extractive agent. The extractive agent may be water and may be separated from the residue and returned to the extractive distillation column.
    Type: Grant
    Filed: May 28, 2014
    Date of Patent: April 7, 2015
    Assignee: Celanese International Corporation
    Inventors: David Lee, Lincoln Sarager, Trinity Hale, Victor J. Johnston
  • Patent number: 8975453
    Abstract: The catalytic conversion of glycerol or acetol to alcohols, such as polyhydric alcohols like propylene glycol and simple alcohols like methanol and ethanol, without the addition of external hydrogen, is improved by the use of a transition metal alloy catalyst which, in the case of glycerol, is a nickel alloy catalyst.
    Type: Grant
    Filed: March 11, 2013
    Date of Patent: March 10, 2015
    Assignee: University of Idaho
    Inventors: Bingjun Brian He, Randy Latayan Maglinao
  • Patent number: 8975450
    Abstract: Ethanol production processes using a mixed feed comprising from 20 to 95 wt. % acetic acid, from 5 to 80 wt. % acetic anhydride, and from 0 to 20 wt. % esters selected from the group consisting of methyl acetate, ethyl acetate, or mixtures thereof are disclosed herein. The process comprises contacting the mixed feed with hydrogen in the vapor phase in a reactor in the presence of a catalyst comprising tin, cobalt, platinum, and combinations thereof to form a crude ethanol product having an ethanol to water molar ratio of greater than 1 and separating the crude ethanol product in one or more distillation columns to yield an ethyl acetate stream and an ethanol stream. The process may be integrated with an acetic anhydride production process to obtain further economic savings.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: March 10, 2015
    Assignee: Celanese International Corporation
    Inventor: Mark O. Scates
  • Publication number: 20150025280
    Abstract: A catalytic system for reductive carbonylation of an alcohol that includes a rhodium complex, an iodide-containing catalyst promoter, and a supporting phosphorus-containing bidentate ligand for the rhodium complex containing at least one aromatic substituent covalently attached to at least one phosphorus of the supporting phosphorus-containing bidentate ligand in an ortho position with an alkoxy substituent or an aryloxy substituent.
    Type: Application
    Filed: December 20, 2012
    Publication date: January 22, 2015
    Applicant: Dow Global Technologies LLC
    Inventors: Thomas P. Clark, Heather A. Spinney, Jason MacDonald, Clark H. Cummins, Jerzy Klosin, John R. Briggs
  • Patent number: 8927790
    Abstract: The present invention relates to processes for the recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. The crude ethanol product is separated in a column to produce a distillate stream comprising ethyl acetate, ethanol and acetaldehyde and a residue stream comprising ethanol, acetic acid and water. The ethanol product is recovered from the residue stream. A liquid recycle stream is sent to a second vaporizer to form a second vapor feed stream that is fed to the hydrogenation reactor.
    Type: Grant
    Filed: July 12, 2012
    Date of Patent: January 6, 2015
    Assignee: Celanese International Corporation
    Inventors: Radmila Wollrab, Victor Johnston
  • Patent number: 8907143
    Abstract: The processes of the current invention relate to the production of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid and ethyl acetate. Conversion of ethyl acetate may be improved by controlling the water content that may be fed to the vaporizer to form a feed stream that may be fed to the hydrogenation reactor. At least 0.01 wt. % water is fed to the vaporizer. The crude ethanol product is separated two or more columns to yield an ethanol product.
    Type: Grant
    Filed: July 6, 2012
    Date of Patent: December 9, 2014
    Assignee: Celanese International Corporation
    Inventors: Radmila Wollrab, Zhenhua Zhou, Victor J. Johnston, David Lee, R. Jay Warner, Heiko Weiner
  • Patent number: 8907142
    Abstract: The process of the current invention relates to the production of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid and ethyl acetate in the presence of a catalyst. Conversion of ethyl acetate may be improved by adding water to the reactor. At least 0.01 wt. % water may be added to the reactor. The crude ethanol product is separated in one or more columns to yield an ethanol product.
    Type: Grant
    Filed: July 6, 2012
    Date of Patent: December 9, 2014
    Assignee: Celanese International Corporation
    Inventors: Radmila Wollrab, Zhenhua Zhou, Victor J. Johnston, David Lee, Heiko Weiner
  • Patent number: 8895786
    Abstract: A process for reducing ethyl acetate and/or diethyl acetal concentration of a crude ethanol product by hydrolysis is disclosed. A portion of the water is initially separated from the crude ethanol product in a first column residue. Ethyl acetate in the first column distillate is hydrolyzed to form additional ethanol and acetic acid. Product ethanol is recovered in a second distillation column preferably in a side stream and acetic acid is removed in the second column residue.
    Type: Grant
    Filed: August 3, 2011
    Date of Patent: November 25, 2014
    Assignee: Celanese International Corporation
    Inventors: Adam Orosco, Manuel Salado, Lincoln Sarager, R. Jay Warner, Trinity Horton
  • Patent number: 8884081
    Abstract: The present invention relates generally to processes for producing ethanol and acetic acid and, in particular, to a process for integrating an ethanol production process with an acetic acid production process.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: November 11, 2014
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Victor J. Johnston, David Lee, Manuel Salado, Mark O. Scates
  • Patent number: 8877987
    Abstract: The present invention relates to the recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. Separation and purification processes of crude ethanol product are employed to allow recovery of an anhydrous ethanol composition. The process involves separating the crude ethanol product using one or more extractive distillation columns that employ one or more extractive agents. The anhydrous ethanol composition comprises less than 1 wt. % water, based on the total weight of the anhydrous ethanol composition.
    Type: Grant
    Filed: August 3, 2011
    Date of Patent: November 4, 2014
    Assignee: Celanese International Corportation
    Inventors: Victor J. Johnston, David Lee, Lincoln Sarager, R. Jay Warner
  • 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
  • Publication number: 20140296584
    Abstract: A method is provided for producing optically active alcohols from ketones by reducing a ketone in the presence of an iridium(III) complex having a chiral prolinamide compound as a ligand.
    Type: Application
    Filed: October 24, 2012
    Publication date: October 2, 2014
    Inventors: Sadayuki Maeda, Tatsunori Sato
  • Patent number: 8846988
    Abstract: Purifying and/or recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. Separation and purification processes of crude ethanol mixture are employed to allow recovery of ethanol and remove impurities. In addition, the process involves returning acetaldehyde separated from the crude ethanol product to the reactor.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: September 30, 2014
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton
  • Publication number: 20140256992
    Abstract: In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.
    Type: Application
    Filed: March 8, 2013
    Publication date: September 11, 2014
    Applicant: PIONEER ENERGY
    Inventors: John Henri, Jan Zygmunt, Mark Bergren, Robert Zubrin
  • Publication number: 20140243526
    Abstract: The present invention relates to processes for the reduction by hydrogenation, using molecular H2, of a C5-C20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N2P2O2, wherein the coordinating atoms N2 are provided by a first bidentate ligand, the coordinating atoms P2 are provided by a second bidentate ligand and the coordinating atoms O2 are provided by two non-linear carboxylate ligands; and —optionally of an acidic additive.
    Type: Application
    Filed: September 27, 2012
    Publication date: August 28, 2014
    Applicant: FIRMENICH SA
    Inventors: Philippe Dupau, Lucia Bonomo, Laurent Kermorvan
  • Patent number: 8809594
    Abstract: Disclosed is a process for the production of higher aldehydes from lower alcohols using a two-stage vapor phase heterogeneous catalyst system. Ethanol feeds afford aldehydes such as butyraldehyde and crotonaldehyde while butanol feeds yield 2-ethylhexanal and 2-ethylhexenal. Higher product selectivities are obtained when the alcohol is first dehydrogenated in the upper catalyst stage followed by aldol condensation of the resulting lower aldehyde to a higher aldehyde.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: August 19, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
  • 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: 8748676
    Abstract: In one embodiment, the invention is to a process for purifying a crude ethanol product. The process comprises the step of hydrogenating acetic acid in a first reaction zone in the presence of a first catalyst to form the crude ethanol product comprising ethanol, acetaldehyde, acetic acid, water, and acetal. The process further comprises the step of separating at least a portion of the crude ethanol product into a refined ethanol stream and a by-product stream. The refined ethanol stream comprises ethanol and acetaldehyde; and the by-product stream comprises acetic acid and a substantial portion of the water from the crude ethanol product. The process further comprises the step of hydrolyzing in a second reaction zone at least a portion of the acetal.
    Type: Grant
    Filed: August 3, 2011
    Date of Patent: June 10, 2014
    Assignee: Celanese International Corporation
    Inventors: Adam Orosco, Lincoln Sarager, R. Jay Warner, Radmila Jevtic
  • Patent number: 8748675
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. The column yields a residue that comprises ethanol, acetic acid, and the extractive agent. The extractive agent may be water and may be separated from the residue and returned to the extractive distillation column.
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: June 10, 2014
    Assignee: Celanese International Corporation
    Inventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
  • Patent number: 8710274
    Abstract: The present invention relates to a method of treating a crude acetone stream. The method generally includes treating a crude acetone stream which has acetone and at least one low-boiling impurity with a catalyst to form a treated acetone stream that has acetone and at least one higher-boiling impurity and then distilling the treated acetone stream to remove at least a portion of the higher-boiling impurity to produce a purified acetone stream. This is particularly helpful in processes where a more pure acetone is desired, including a process for making purified isopropanol.
    Type: Grant
    Filed: May 4, 2012
    Date of Patent: April 29, 2014
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel B Pourreau, Roger A Grey, Andrew P Kahn
  • Patent number: 8704012
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using a low energy process and an entrainer. The crude ethanol product is separated in an distillation column to produce a distillate stream comprising the entrainer. The ethanol product is recovered from the residue stream.
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: April 22, 2014
    Assignee: Celanese International Corporation
    Inventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
  • Patent number: 8704011
    Abstract: A crude ethanol product obtained from the hydrogenation of acetic acid comprises ethanol and ethyl acetate. Using a distillation column operated at a pressure of from 0.1 to 100 kPa, the ethyl acetate and ethanol may be effectively separated. In addition, maintaining the amount of water that is fed to the distillation column to an amount less than 10 wt. %, based on the weight of all components fed to the distillation column, provides an energy benefit.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: April 22, 2014
    Assignee: Celanese International Corporation
    Inventors: Lincoln Sarager, R. Jay Warner, Trinity Horton, David Lee, Victor J. Johnston, Manuel Salado
  • Publication number: 20140088326
    Abstract: Disclosed is a process for the production of higher aldehydes from lower alcohols using a two-stage vapor phase heterogeneous catalyst system. Ethanol feeds afford aldehydes such as butyraldehyde and crotonaldehyde while butanol feeds yield 2-ethylhexanal and 2-ethylhexenal. Higher product selectivities are obtained when the alcohol is first dehydrogenated in the upper catalyst stage followed by aldol condensation of the resulting lower aldehyde to a higher aldehyde.
    Type: Application
    Filed: September 21, 2012
    Publication date: March 27, 2014
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
  • Patent number: 8680342
    Abstract: Purifying and/or recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid from an feed stream comprising water. The presence of water does not significantly impact acid conversion or selectivity to ethanol. Further the addition of water allows for improved recovery of ethanol.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: March 25, 2014
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor J. Johnston, Tianshu Pan, R. Jay Warner, Heiko Weiner, Josefina T. Chapman
  • Publication number: 20140024863
    Abstract: A liquid/gas reactor includes a bulk catalyst bed and means for supplying fresh feed and recycled at least partially converted liquid product stream to the bulk catalyst bed. The reactor also includes means for collecting an at least partially converted liquid product stream from the bulk catalyst bed and recycling at least a portion thereto. A minor catalyst bed extends substantially vertically through the bulk catalyst bed. Means for supplying recycled at least partially converted product stream only to the minor catalyst bed is also provided. A separating wall is disposed between the bulk catalyst bed and the minor catalyst bed.
    Type: Application
    Filed: January 12, 2012
    Publication date: January 23, 2014
    Applicant: DAVY PROCESS TECHNOLOGY LIMITED
    Inventors: Edward Adrian Lord, Arthur James Reason
  • Publication number: 20130296612
    Abstract: The present invention relates to a method of treating a crude acetone stream. The method generally includes treating a crude acetone stream which has acetone and at least one low-boiling impurity with a catalyst to form a treated acetone stream that has acetone and at least one higher-boiling impurity and then distilling the treated acetone stream to remove at least a portion of the higher-boiling impurity to produce a purified acetone stream. This is particularly helpful in processes where a more pure acetone is desired, including a process for making purified isopropanol.
    Type: Application
    Filed: May 4, 2012
    Publication date: November 7, 2013
    Applicant: LYONDELL CHEMICAL TECHNOLOGY, L.P.
    Inventors: DANIEL B. POURREAU, ROGER A. GREY, ANDREW P. KAHN
  • Patent number: 8563787
    Abstract: Process for preparing homoallyl alcohols by catalyzed reaction of alkenes with aldehydes or ketones, wherein the reaction is carried out in the gas phase in the presence of noncovalently supported ionic liquid phase catalysts.
    Type: Grant
    Filed: October 4, 2011
    Date of Patent: October 22, 2013
    Assignee: BASF SE
    Inventors: Christoph Stock, Dirk Gerhard, Klaus Ebel
  • Publication number: 20130261348
    Abstract: Ethane is oxidized to ethylene and/or oxygenates that comprise acetic acid. The acetic acid may be converted to ethanol by hydrogenation. The ethylene may be converted to ethanol by hydration.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Applicant: Celanese International Corporation
    Inventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
  • Patent number: 8546621
    Abstract: The present invention is directed to a process for the manufacture of 3,7-dimethyl-1-octen-3-ol comprising the following steps: a) hydrogenation of 6-methyl-5-hepten-2-on to 6-methyl-2-heptanon in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of carbon, calcium carbonate and aluminum oxide. b) reaction of 6-methyl-2-heptanon with acetylene to 3,7-dimethyl-1-octin-3-ol in the presence of ammonia and potassium hydroxide and in the absence of any additional organic solvent; c) hydrogenation of 3,7-dimethyl-1-octin-3-ol to 3,7-dimethyl-1-octen-3-ol in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of calcium carbonate, aluminum oxide, silica, porous glass, carbon or graphite, and barium sulphate, with the proviso that the catalyst additionally contains lead when the carrier is calcium carbonate.
    Type: Grant
    Filed: August 24, 2011
    Date of Patent: October 1, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Johannes Tschumi, Jonathan Medlock
  • Patent number: 8536236
    Abstract: A method for the preparation of an eggshell catalyst is described comprising the steps of i) immersing shaped units of an oxidic support having a smallest unit dimension ?0.5 mm in a solution of cobalt ammine carbonate, ii) heating the solution to a temperature between 60 and 120° C. to precipitate cobalt compounds onto the surface of the shaped units, iii) separating the resulting supported cobalt compounds from the remaining solution, and iv) drying the supported cobalt compounds. The cobalt compounds may be reduced to provide catalysts suitable for the hydrogenation of unsaturated compounds or the Fischer-Tropsch synthesis of hydrocarbons.
    Type: Grant
    Filed: November 21, 2005
    Date of Patent: September 17, 2013
    Assignee: Johnson Matthey PLC
    Inventors: Cornelis Martinus Lok, Sharon Bale
  • Patent number: 8497400
    Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.
    Type: Grant
    Filed: February 9, 2010
    Date of Patent: July 30, 2013
    Assignee: Takasago International Corporation
    Inventors: Hideo Shimizu, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
  • Patent number: 8481791
    Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.
    Type: Grant
    Filed: February 9, 2010
    Date of Patent: July 9, 2013
    Assignee: Takasago International Corporation
    Inventors: Hideo Shimizu, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
  • Patent number: 8455701
    Abstract: The present invention relates to a method for producing at least one decanol by means of hydrogenating at least one decenal, wherein a first hydrogenation is carried out in the liquid phase on a solid first catalyst, wherein the first catalyst contains copper and nickel. The aim of the invention is to provide a method of the type mentioned above, according to which decenals can be hydrogenated into decanols in high yields even after long operating periods. The content of non-reacted decenals in the hydrogenation discharge in particular should be less than 1500 ppm. Said aim is achieved by carrying out the hydrogenation in two steps, which is to say in a first step in a known manner using a catalyst comprising copper, nickel and optionally chromium and/or barium oxide, and subsequently in a second step using a different catalyst that must be free of copper, chromium and nickel.
    Type: Grant
    Filed: August 13, 2010
    Date of Patent: June 4, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Alfred Kaizik, Hans-Gerd Lueken