Catalyst Utilized Patents (Class 568/885)
  • Patent number: 11926577
    Abstract: The present disclosure pertains to a new synthetic method for the preparation of 2-methyl-2-hydroxyheptane and 2-methyl-2-alkoxyheptanes, which are valuable commodities for use in flavors, fragrances and various personal care products, such as cosmetics.
    Type: Grant
    Filed: October 8, 2021
    Date of Patent: March 12, 2024
    Assignee: P2 SCIENCE, INC.
    Inventors: Patrick Foley, Yonghua Yang, Yong Tu
  • Patent number: 11807589
    Abstract: A process, a system, and an apparatus are provided for converting a lower alkane to an alkene. Oxygen and a lower alkane are provided to an ODH reactor. At least a portion of the lower alkane is converted to an alkene and an ODH stream comprising the alkene, an oxygenate, water, and carbon monoxide is produced. The ODH stream is provided to a water gas shift/hydrogenation (WGS/H) reactor including a WGS/H catalyst. The ODH stream is reacted within the WGS/H reactor and hydrogen and carbon dioxide are generated from the carbon monoxide and water. At least a portion of the oxygenate and hydrogen are converted to an alcohol. Additionally, the alcohol may be dehydrated to form additional alkene and water.
    Type: Grant
    Filed: December 20, 2019
    Date of Patent: November 7, 2023
    Assignee: NOVA Chemicals (International) S.A.
    Inventors: Shahin Goodarznia, Vasily Simanzhenkov, Bolaji Olayiwola, Yipei Styles
  • Patent number: 11654421
    Abstract: Methods of producing metal catalysts can include mixing two or more metal salts and an aluminum salt in water to produce a metal catalyst precursor solution; mixing the metal catalyst precursor solution and an alkali metal buffer solution to produce a precipitate; ion exchanging the alkali metal in the precipitate for a non-alkali cation to produce a low-alkali metal precipitate comprising 3 wt % or less alkali metal by weight of the precipitate on a dry basis; producing a powder from the low-alkali metal precipitate; and calcining the powder to produce a metal catalyst. Such metal catalysts may be useful in producing bifunctional catalyst systems that are useful in, among other things, converting syngas to dimethyl ether in a single reactor.
    Type: Grant
    Filed: August 13, 2020
    Date of Patent: May 23, 2023
    Assignee: EXXONMOBIL TECHNOLOGY AND ENGINEERING COMPANY
    Inventors: Chuansheng Bai, Majosefina Cunningham, Jihad M. Dakka, Preeti Kamakoti, Aruna Ramkrishnan, Anjaneya S. Kovvali, Anita S. Lee
  • Patent number: 11638912
    Abstract: Methods of producing metal catalysts can include mixing two or more metal salts and an aluminum salt in water to produce a metal catalyst precursor solution having a pH of about 2.5 to about 4.0; mixing the metal catalyst precursor solution and a basic solution having a pH of about 10 to about 13 to produce a mixture with a pH of about 6 to about 7 and a precipitate; producing a powder from the precipitate; and calcining the powder to produce a metal catalyst. Such metal catalysts may be useful in producing bifunctional catalyst systems that are useful in, among other things, converting syngas to dimethyl ether in a single reactor.
    Type: Grant
    Filed: August 13, 2020
    Date of Patent: May 2, 2023
    Assignee: EXXONMOBIL TECHNOLOGY AND ENGINEERING COMPANY
    Inventors: Chuansheng Bai, Majosefina Cunningham, Jihad M. Daaka, Preeti Kamakoti, Aruna Ramkrishnan
  • Patent number: 11439989
    Abstract: Disclosed is a hydrofining catalyst comprising: an inorganic refractory component comprising a first hydrodesulfurization catalytically active component in a mixture with at least one oxide selected from the group consisting of alumina, silica, magnesia, calcium oxide, zirconia and titania; a second hydrodesulfurization catalytically active component; and an organic component comprising a carboxylic acid and optionally an alcohol. The hydrofining catalyst of the present application shows improved performance in the hydrofining of distillate oils. Also disclosed are a hydrofining catalyst system comprising the hydrofining catalyst, a method for preparing the catalyst and catalyst system, and a process for the hydrofining of distillate oils using the catalyst or catalyst system.
    Type: Grant
    Filed: April 9, 2019
    Date of Patent: September 13, 2022
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, RESEARCH INSTITUTE OF PETROLEUM PROCESSING, SINOPEC
    Inventors: Wenbin Chen, Le Zhang, Xiangyun Long, Hong Nie, Mingfeng Li, Dadong Li, Qinghe Liu, Xueyan Ju
  • Patent number: 11242299
    Abstract: Embodiments of methods of synthesizing a metathesis catalyst system, which include impregnating tungsten oxide on silica support in the presence of a precursor to produce a base catalyst; calcining the base catalyst; impregnating a metal oxide co-catalyst comprising a metal oxide onto the surface of the base catalyst to produce a doped catalyst; and calcining the doped catalyst to produce a metathesis catalyst system. Further embodiments of processes for the production of propylene, which include contacting a hydrocarbon feedstock comprising a mixture of 1-butene and 2-butene with embodiments of the metathesis catalyst system to produce, via metathesis conversion, a product stream comprising propylene.
    Type: Grant
    Filed: October 10, 2018
    Date of Patent: February 8, 2022
    Assignees: Saudi Arabian Oil Company, Aramco Services Company
    Inventors: Munir D. Khokhar, Mohammed R. Alalouni, Noor A. Sulais, Brian Hanna, Sohel K. Shaikh
  • Patent number: 11173479
    Abstract: Provided herein is a novel process for producing shaped catalyst bodies in which a mixture having aluminum contents of Al±0 in the range from 80 to 99.8% by weight, based on the mixture used, is used to form a specific intermetallic phase, shaped catalyst bodies obtainable by the process of the invention, a process for producing an active catalyst fixed bed including the shaped catalyst bodies provided herein, the active catalyst fixed beds and also the use of these active catalyst fixed beds for the hydrogenation of organic hydrogenatable compounds or for formate degradation.
    Type: Grant
    Filed: September 10, 2018
    Date of Patent: November 16, 2021
    Assignee: BASF SE
    Inventors: Marie Katrin Schroeter, Irene de Wispelaere, Michael Schwarz, Rolf Pinkos, Inna Schwabauer
  • Patent number: 11090637
    Abstract: The present invention relates to a fixed bed of catalytically active metal foam bodies having a volume of not more than 500 mL which consist to an extent of at least 95 wt % of metals. The fixed bed is used for catalytic reactions in a three-phase reaction mixture.
    Type: Grant
    Filed: September 27, 2017
    Date of Patent: August 17, 2021
    Assignee: Evonik Operations GmbH
    Inventors: Stefan Wieland, Meike Roos, René Poss
  • Patent number: 11090636
    Abstract: A hydroprocessing catalyst has been developed. The catalyst is a crystalline transition metal tungstate material or metal sulfides derived therefrom, or both. The hydroprocessing using the crystalline transition metal tungstate material may include hydrodenitrification, hydrodesulfurization, hydrodemetallation, hydrodesilication, hydrodearomatization, hydroisomerization, hydrotreating, hydrofining, and hydrocracking. A data system comprising at least one processor; at least one memory storing computer-executable instructions; and at least one receiver configured to receive data of a conversion process comprising at least one reaction catalyzed by the catalyst or a metal sulfide decomposition product of the catalyst has been developed.
    Type: Grant
    Filed: August 23, 2018
    Date of Patent: August 17, 2021
    Assignee: UOP LLC
    Inventors: Stuart R. Miller, Susan C. Koster
  • Patent number: 10875823
    Abstract: The invention relates to novel methods for preparing N-methyl-p-toluidine for the use thereof as additive for aviation fuel, and to specific catalysts for these methods.
    Type: Grant
    Filed: December 19, 2017
    Date of Patent: December 29, 2020
    Assignee: LANXESS Deutschland GmbH
    Inventors: Martina Gerdinand, Rainer Dost, Ralf Krahwinkel, Hans-Jurgen Quella, Daniel Ullrich, Patrick Kurr
  • Patent number: 10836693
    Abstract: The present invention provides a process for the preparation of Docosanol (I). The process comprises reducing cis-13-Docosenoic acid (V) to obtain Docosanoic acid (III), which is further reduced to obtain Docosanol (I).
    Type: Grant
    Filed: May 28, 2018
    Date of Patent: November 17, 2020
    Assignee: Aurobindo Pharma Ltd.
    Inventors: Nandi Sukumar, Theriviam Sudalayandi Shanmugam Sundaram Dhanraj, Sreedhar Reddy Dwarakapally, Ravi Kumar Gupta Miriyala, Sivakumaran Meenakshisunderam
  • Patent number: 10626518
    Abstract: A method for treating a surface of a metallic structure, the metallic structure being made of a first metallic material; the method including the steps of: (a) bonding an alloy material made of the first metallic material and a second metallic material with the structure; and (b) etching away at least some of the first metallic material from a structure obtained after step (a) so as to obtain a treated structure with an increased specific surface area compared with the metallic structure before treatment.
    Type: Grant
    Filed: May 31, 2016
    Date of Patent: April 21, 2020
    Assignee: City University of Hong Kong
    Inventors: Yawen Zhan, Yangyang Li, Jian Lu
  • Patent number: 10537877
    Abstract: A method for preparing a silica-modified catalyst support is described comprising: (i) applying an alkyl silicate solution to a porous support material in an amount to produce a silica content of the silica-modified catalyst support, expressed as Si, in the range 0.25 to 15% by weight, (ii) drying the resulting silicate-modified support and recovering a first alcoholic solution, (iii) optionally treating the dried silicate-modified support with water, drying the resulting water-treated support and recovering a second alcoholic solution, and (iv) calcining the dried material to form the silica-modified catalyst support, wherein the first alcoholic solution contains ?10 vol % water and at least a portion of the first alcoholic solution is mixed with alkyl silicate to form the alkyl silicate solution.
    Type: Grant
    Filed: July 12, 2016
    Date of Patent: January 21, 2020
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Alejandro Martin Antonini, Richard John Mercer, Jose Angel Ruiz Adan
  • Patent number: 10047027
    Abstract: A method of forming methanol by irradiating a mixture comprising water, carbon dioxide, and a photocatalyst with UV light to photo-catalytically reduce the carbon dioxide thereby forming methanol, wherein the photocatalyst comprises non-templated indium-oxide nanoparticles and/or templated indium-oxide nanoparticles. Various combinations of the embodiments of the templated indium-oxide nanoparticles and the non-templated indium-oxide nanoparticles photocatalyst as well as the method of forming methanol are provided.
    Type: Grant
    Filed: November 8, 2017
    Date of Patent: August 14, 2018
    Assignee: King Fahd University of Petroleum and Minerals
    Inventors: Muhammad Ashraf Gondal, Mohamed A. Dastageer, Umair Baig
  • Patent number: 9909047
    Abstract: Disclosed is a method of preparing a drilling fluid and lube base oil using biomass-derived fatty acid, including hydrogenating a fatty acid mixture derived from fat of biological origin so as to be converted into a fatty alcohol mixture, which is then dehydrated to give a C16 and C18 linear internal olefin mixture, which is then oligomerized to give olefinic lube base oil, followed by hydrofinishing to remove the olefin, yielding high-quality lube base oil (e.g. Group III or higher lube base oil). The C16 and C18 linear internal olefin mixture, which is a reaction intermediate, can be utilized as a high-quality drilling fluid.
    Type: Grant
    Filed: June 2, 2015
    Date of Patent: March 6, 2018
    Assignees: SK INNOVATION CO., LTD., SK LUBRICANTS CO., LTD.
    Inventors: Hee Jung Jeon, Wan Seop Kwon, Jin Hee Ok, Yeon Ho Kim, Yong Woo Kim, Yong Woon Kim
  • Patent number: 9695097
    Abstract: This invention relates to a process for producing ethanol comprises supplying a feed comprising carbon monoxide, hydrogen and dimethyl ether to a reaction zone operated under conditions such that (i) part of the carbon monoxide in the feed reacts with part of the hydrogen in the feed to produce methanol; (ii) part of the carbon monoxide in the feed reacts with at least part of the dimethyl ether in the feed to produce methyl acetate; and (iii) part of the hydrogen in the feed reacts with at least part of the methyl acetate produced in (ii) to produce an effluent comprising methanol and ethanol. At least part of the ethanol is recovered from the effluent and at least part of the methanol is dehydrated to produce dimethyl ether, which is recycled to the reaction zone.
    Type: Grant
    Filed: June 17, 2016
    Date of Patent: July 4, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Michael Salciccioli, James H. Beech, Jr., Ranjita Ghose, Paul F. Keusenkothen, Meha Rungta
  • Patent number: 9670119
    Abstract: The present invention produces ethanol in a stacked bed reactor that comprises a first catalyst and a second catalyst, wherein the first and second catalysts comprise at least one group VIII metal, and wherein the second catalyst is substantially free of copper. The crude ethanol product may be separated and ethanol recovered.
    Type: Grant
    Filed: January 11, 2012
    Date of Patent: June 6, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Heiko Weiner, Zhenhua Zhou, Radmila Jevtic, Victor J. Johnston
  • Patent number: 9670120
    Abstract: The present invention relates to a solid catalyst for producing ethanol from acetic acid, ethyl acetate, or mixtures thereof comprising a core region comprising a Group IIA metal and a surface region surrounding the core region and comprising one or more main metals. The total loading of the main metals in the catalyst is greater than or equal to 1 wt. %. Also more than 85% of main metals are located in the surface region, based on the total loading of the main metals in the catalyst. The surface region may comprise two or more layers.
    Type: Grant
    Filed: January 27, 2015
    Date of Patent: June 6, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Heiko Weiner, Zhenhou Zhou
  • Patent number: 9440898
    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: July 30, 2015
    Date of Patent: September 13, 2016
    Assignee: PIONEER ENERGY
    Inventors: John T. Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
  • Patent number: 9382177
    Abstract: A process is disclosed for producing ethanol, comprising contacting hydrogen and a feed stream comprising acetic acid in a reactor in the presence of a catalyst comprising a binder and a mixed oxide comprising a promoter metal and tin, and preferably also comprising cobalt. The promoter metal is selected from the group consisting of rhenium, ruthenium, rhodium, palladium, osmium, iridium, platinum, and combinations thereof. The feed stream may comprises pure acetic acid or may comprise a mixture of 50 to 95 wt. % acetic acid and 5 to 50 wt. % ethyl acetate.
    Type: Grant
    Filed: April 28, 2014
    Date of Patent: July 5, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Zhenhua Zhou, Victor J. Johnston, Heiko Weiner
  • Patent number: 9353034
    Abstract: The present invention is directed to the separation of ethanol from a crude ethanol product obtained from the vaporization and hydrogenation of acetic acid using reduced residence time for the vapor phase reactants between exiting the vaporizer and entering the reactor. The crude ethanol product is separated in at least one column to recover an ethanol product.
    Type: Grant
    Filed: February 7, 2012
    Date of Patent: May 31, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Radmila Jevtic, Victor J. Johnston, David Lee, Heiko Weiner, Zhenhua Zhou
  • Patent number: 9353035
    Abstract: A process is disclosed for producing ethanol comprising contacting reactants comprising acetic acid and hydrogen in a reactor in the presence of a first catalyst in a first zone and a second catalyst in a second zone. The first catalyst is a mixed oxide comprising tin and at least one of cobalt or nickel. The second catalyst may be either: i) a supported Group VIII hydrogenation catalyst; ii) a copper-based catalyst; and iii) a secondary mixed oxide catalyst, wherein the secondary mixed oxide catalyst is different than the mixed oxide catalyst of the first zone.
    Type: Grant
    Filed: April 27, 2015
    Date of Patent: May 31, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Heiko Weiner, Zhenhua Zhou, Victor J. Johnson
  • Patent number: 9328044
    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 reactor in the presence of a catalyst to form the crude ethanol product. The process further comprises the step of separating at least a portion of the crude ethanol product in a purification zone. The purification zone preferably comprises a first column, which yields a first distillate comprising ethanol, water and ethyl acetate, and a first residue comprising acetic acid. The at least a portion of the crude ethanol product has a residence time from the reactor to the purification zone from 5 minutes to 5 days.
    Type: Grant
    Filed: September 16, 2013
    Date of Patent: May 3, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Trinity Horton Hale, Radmila Wollrab, Victor J. Johnston, Tianshu Pan, R. Jay Warner, Heiko Weiner, Nathan Bower, Josefina T. Chapman, Gerald Grusendorf
  • Patent number: 9290441
    Abstract: A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.
    Type: Grant
    Filed: May 14, 2012
    Date of Patent: March 22, 2016
    Assignee: Yeda Research and Development Co. Ltd.
    Inventors: David Milstein, Chidambaram Gunanathan, Yehoshua Ben-David, Ekambaram Balaraman, Boopathy Gnanaprakasam, Jing Zhang
  • Patent number: 9233899
    Abstract: The present invention relates to a catalyst having an amorphous support and one or more active metals. The amorphous support may comprise a support material and an amorphous support modifier, which adjusts the acidity of the support material. In preparing the amorphous catalyst, post-synthesis treatment, i.e. calcination, may be used to adjust the catalyst performance while converting acetic acid to ethanol.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: January 12, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Heiko Weiner, Zhenhua Zhou, Victor J. Johnston
  • Patent number: 9193651
    Abstract: The chemoselective reduction of a carboxylic ester (I) to an alcohol by catalytic hydrogenation, in particular in the presence of a transition metal complex, more particularly in the presence of a ruthenium (II) complex is described.
    Type: Grant
    Filed: May 16, 2013
    Date of Patent: November 24, 2015
    Assignee: Givaudan S.A.
    Inventors: Roger Wilhelm Geisser, Andreas Goeke, Fridtjof Schroeder
  • Patent number: 9156754
    Abstract: A process for recovering ethanol obtained from the hydrogenation of acetic acid. The crude ethanol product is separated in a column to produce a distillate stream comprising acetaldehyde and ethyl acetate and a residue stream comprising ethanol, acetic acid, ethyl acetate and water. The ethanol product is recovered from the residue stream.
    Type: Grant
    Filed: December 16, 2014
    Date of Patent: October 13, 2015
    Assignee: Celanese International Corporation
    Inventors: David Lee, Adam Orosco, Claudio Ribeiro, R. Jay Warner, Robert Alan Deck, Emily Duff, Victor J. Johnston
  • Patent number: 9150474
    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 the esterification of acetic acid in a column used for recovering the ethanol.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: October 6, 2015
    Assignee: Celanese International Corporation
    Inventors: Zhenhua Zhou, Victor J. Johnston, David Lee, Heiko Weiner
  • Patent number: 9150478
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using a low energy process. The crude ethanol product is separated in a column to produce a distillate stream comprising acetaldehyde and a residue stream comprising ethanol, acetic acid, ethyl acetate and water. The ethanol product is recovered from the residue stream.
    Type: Grant
    Filed: December 15, 2014
    Date of Patent: October 6, 2015
    Assignee: Celanese International Corporation
    Inventors: David Lee, Fred Ronald Olsson, Adam Orosco, Nathan Kirk Powell, Manuel Salado, Lincoln Sarager, R. Jay Warner, Radmila Wollrab, Victor J. Johnston
  • Patent number: 9126194
    Abstract: The present invention relates to a catalyst composition having a support that contains tin. The catalyst is used for converting acetic acid to ethanol. The catalyst may also comprise one or more active metals and a support modifier.
    Type: Grant
    Filed: February 29, 2012
    Date of Patent: September 8, 2015
    Assignee: Celanese International Corporation
    Inventors: Heiko Weiner, Zhenhua Zhou, Radmila Jevtic, Victor J. Johnston
  • Patent number: 9102581
    Abstract: 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 ethanol and remove impurities. In addition, the process involves separating the crude ethanol product using an extractive distillation column that employs an extraction agent, such as a recycled stream comprising water.
    Type: Grant
    Filed: October 4, 2012
    Date of Patent: August 11, 2015
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Radmila Wollrab, Wael Amleh, Gerald Grusendorf, Trinity Horton Hale, Victor J. Johnston, Fred Ronaold Olsson, Nathan Kirk Powell, Manuel Salado, Lincoln Sarager
  • Patent number: 9079172
    Abstract: The present invention relates to a process for the formation of an alcohol from an alkanoic acid, the steps of the process comprising: contacting a feed stream containing the alkanoic acid and hydrogen at an elevated temperature with a hydrogenating catalyst comprising from 3 to 25 wt. % of active metals comprising tin and cobalt and a metal promoter selected from the group consisting of noble metals or first metal, the first metal selected from the group of barium, cesium and potassium.
    Type: Grant
    Filed: March 13, 2012
    Date of Patent: July 14, 2015
    Assignee: Celanese International Corporation
    Inventors: Heiko Weiner, Zhenhua Zhou, Radmila Jevtic, Victor J. Johnston
  • Patent number: 9073816
    Abstract: Recycle streams in an ethanol production process are hydrolyzed to reduce ethyl acetate concentration. In the process, acetic acid is hydrogenated to form a crude ethanol product, which undergoes a separation or purification process. Ethyl acetate is formed as a byproduct of the hydrogenation of acetic acid. The hydrolysis of recycle steams from the separation process can reduce the concentration of ethyl acetate, converting some or all of the ethyl acetate to acetic acid and ethanol.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: July 7, 2015
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Heiko Weiner, Zhenhua Zhou, Emily Duff, Radmila Jevtic, Victor J. Johnston, David Lee, Adam Orosco
  • Patent number: 9073042
    Abstract: The present invention relates to a process for hydrogenating feedstock comprising acetic acid in the presence of hydrogen to product comprising ethanol in a reaction zone under hydrogenation conditions over a catalyst composition promoted with cobalt, rhodium, cesium or a combination thereof on a previously calcined composition comprising at least one Group VIII metal and tin on a support material.
    Type: Grant
    Filed: March 14, 2012
    Date of Patent: July 7, 2015
    Assignee: Celanese International Corporation
    Inventors: Zhenhua Zhou, Victor J. Johnston, Heiko Weiner
  • Patent number: 9073815
    Abstract: A process is disclosed for producing ethanol, comprising contacting acetic acid and hydrogen in a reactor in the presence of a catalyst comprising a binder and a mixed oxide comprising cobalt and preferably tin, wherein the mixed oxide is present in an amount from 60 to 90 wt. %, based on the total weight of the catalyst.
    Type: Grant
    Filed: April 28, 2014
    Date of Patent: July 7, 2015
    Assignee: Celanese International Corporation
    Inventors: Heiko Weiner, Zhenhua Zhou, Victor J. Johnston
  • Patent number: 9073814
    Abstract: Ethanol production from the hydrogenation of acetic acid requires energy to drive the hydrogenation reaction and the purification of the crude ethanol product. Heat integration process to recover heat from one part of the production process to be used within the process improves efficiencies and reduces costs.
    Type: Grant
    Filed: October 1, 2013
    Date of Patent: July 7, 2015
    Assignee: Celanese International Corporation
    Inventors: Nathan Kirk Powell, Samuel Roundy, Lincoln Sarager, Murray Viard, R. Jay Warner, Gerald Grusendorf, Radmila Wollrab, Victor J. Johnston, Fred Ronald Olsson
  • Patent number: 9051238
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. Separation and purification processes of the crude ethanol products are employed to allow recovery of ethanol and remove impurities.
    Type: Grant
    Filed: January 14, 2014
    Date of Patent: June 9, 2015
    Assignee: Celanese International Corporation
    Inventors: Lincoln Sarager, R. Jay Warner, Heiko Weiner, Radmila Wollrab, Josefina T. Chapman, Robert Cunningham, Gerald Grusendorf, Trinity Horton Hale, Victor J. Johnston, Tianshu Pan
  • Patent number: 9051235
    Abstract: The present invention relates to a process for the production of ethanol using a molar excess of hydrogen. A mixed feed of acetic acid and ethyl acetate is fed to a reactor to be converted to ethanol. Hydrogen flow is increased to avoid a negative conversion of ethyl acetate.
    Type: Grant
    Filed: February 7, 2012
    Date of Patent: June 9, 2015
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor J. Johnston, David Lee, Heiko Weiner, Zhenhua Zhou
  • Patent number: 9050585
    Abstract: A hydrogenation catalyst and process using the catalyst for converting a mixture comprising acetic acid and ethyl acetate to ethanol at a first temperature, and the catalyst desorbs ethyl acetate, in the absence of hydrogen, at a second temperature that is greater than the first temperature. The catalyst has a suitable chemisorption of ethyl acetate at the first temperature in the absence of hydrogen. In one embodiment, the first temperature ranges from 125° C. to 350° C. and the second temperature ranges from 300° C. to 600° C. The catalyst comprises one or more active metals or oxide thereof on a support that comprises tungsten or an oxide thereof. The one or more active metals are selected from the group consisting of cobalt, copper, gold, iron, nickel, palladium, platinum, iridium, osmium, rhenium, rhodium, ruthenium, tin, zinc, lanthanum, cerium, manganese, chromium, vanadium, and molybdenum.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: June 9, 2015
    Assignee: Celanese International Corporation
    Inventors: Zhenhua Zhou, Heiko Weiner, Dheeraj Kumar, Xiaoyan Tu, Victor J. Johnston, Radmila Jevtic
  • Patent number: 9040443
    Abstract: Catalysts and processes for forming catalysts for use in hydrogenating acetic acid to form ethanol. In one embodiment, the catalyst comprises a first metal, a silicaceous support, and at least one metasilicate support modifier. Preferably, the first metal is selected from the group consisting of copper, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, titanium, zinc, chromium, rhenium, molybdenum, and tungsten. In addition the catalyst may comprise a second metal preferably selected from the group consisting of copper, molybdenum, tin, chromium, iron, cobalt, vanadium, tungsten, palladium, platinum, lanthanum, cerium, manganese, ruthenium, rhenium, gold, and nickel.
    Type: Grant
    Filed: June 12, 2013
    Date of Patent: May 26, 2015
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Barbara F. Kimmich, John L. Potts, Heiko Weiner, Radmila Wollrab, James H. Zink, Josefina T. Chapman, Laiyuan Chen
  • Patent number: 9040748
    Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of aqueous formaldehyde. The water in the hydrocarboxylation zone is reduced via reaction with the ester bonds in a recycle stream comprising glycolic acid oligomers and/or methyl glycolate oligomers.
    Type: Grant
    Filed: June 8, 2012
    Date of Patent: May 26, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Scott Donald Barnicki, Robert Thomas Hembre, Kelley Margaret Moran, Stephen Neal Falling
  • 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: 20150133701
    Abstract: A process is disclosed for integrating a steam methane reformer to produce hydrogen that is used for converting acetic acid and/or ethyl acetate to ethanol. The process may use a methane-containing stream obtained from a stranded natural gas or associated gas source. The process water from the hydrogenation reaction is used to saturate the methane-containing stream. The process water comprises water and oxygenates, wherein the maximum amount of oxygenates is less than or equal to 10 wt. %. Processes for integrating fuel sources, steam and electricity are also disclosed.
    Type: Application
    Filed: November 8, 2013
    Publication date: May 14, 2015
    Applicant: Celanese International Corporation
    Inventors: David Townsend, Andrew Shuff
  • Patent number: 9029614
    Abstract: Disclosed herein are processes for alcohol production by reducing ethyl acetate produced by hydrogenating acetic acid in the presence of a suitable catalyst. The product of the acetic acid hydrogenation is fed directly to a decanter to separate the hydrogenation product into an aqueous phase comprising water and ethanol and an organic phase comprising ethyl acetate. The organic phase 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. Thus, ethanol may be produced from acetic acid through an ethyl acetate intermediate without an esterification step. This may reduce the recycle of ethanol in the hydrogenolysis process and improve ethanol productivity.
    Type: Grant
    Filed: November 20, 2012
    Date of Patent: May 12, 2015
    Assignee: Celanese International Corporation
    Inventors: Emily Duff, R. Jay Warner, Heiko Weiner, Radmila Wollrab, Zhenhua Zhou, James Zink, Andrew Shuff
  • 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: 9024082
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. A diluted acid stream, comprising less than 30 wt. % acetic acid, is used as the extractive agent and is fed at a point above the crude feed stream. The column yields a residue that comprises ethanol, acetic acid, and water. The diluted acid stream may be separated from the residue and returned to the extractive distillation column.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Victor J. Johnston, David Lee, Adam Orosco
  • Patent number: 9024083
    Abstract: The present invention produces ethanol in a reactor that comprises a catalyst composition and a feed stream comprising acetic acid and a recycled liquid stream comprising ethyl acetate. The catalyst composition comprises a first catalyst comprising platinum, cobalt, and/or tin and a second catalyst comprising copper. The crude ethanol product may be separated and ethanol recovered.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: Zhenhua Zhou, Iva Franjkic, Radmila Jevtic, Victor J. Johnston, David Lee, Heiko Weiner
  • Patent number: 9024086
    Abstract: The present invention relates to catalysts and to chemical processes employing such catalysts. The catalysts are preferably used for converting acetic acid to ethanol. The catalyst comprises acidic sites and two or more metals. The catalyst has acidic sites on the surface and the balance favors Lewis acid sites.
    Type: Grant
    Filed: January 4, 2013
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: Zhenhua Zhou, Heiko Weiner
  • Patent number: 9024085
    Abstract: The present invention is directed to processes for recovering ethanol obtained from the hydrogenation of acetic acid. Acetic acid is hydrogenated in the presence of a catalyst in a hydrogenation reactor to form a crude ethanol product. The crude ethanol product is separated in one or more columns to recover ethanol. In some embodiments, less than 10 wt. % ethanol is recycled to the hydrogenation reactor.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: David Lee, Adam Orosco, Claudio Ribeiro, R. Jay Warner, Robert Alan Deck, Emily Duff, Victor J. Johnston
  • Patent number: 9024084
    Abstract: The present invention is directed to processes for the recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using a low energy process. The crude ethanol product is separated in one or more columns. At least one of the columns is operated at a controlled pressure to enhance separation of ethanol and organics. In one embodiment, there are at least two columns that operate at controlled pressures.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: David Lee, Adam Orosco, R. Jay Warner, Victor J. Johnston