Catalyst Utilized Patents (Class 568/881)
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Patent number: 12195588Abstract: The invention contemplates certain polyethers, polyether derivatives, and methods of making and using those same polymers. For example, the starting materials can, e.g., citronellol, prenol, isocitronellol and isoprenol.Type: GrantFiled: October 17, 2023Date of Patent: January 14, 2025Assignee: P2 SCIENCE, INC.Inventors: Patrick Foley, Yonghua Yang, Tania Salam
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Patent number: 12006279Abstract: The present invention relates to a process for producing alcohols by hydrogenation of C13 aldehydes. The process according to the invention is performed in two consecutive hydrogenation stages, wherein the first hydrogenation stage employs an activated metal catalyst based on a nickel metal foam and the second stage employs a supported catalyst containing a catalytically active component from the group consisting of nickel, copper, chromium and mixtures thereof.Type: GrantFiled: February 23, 2023Date of Patent: June 11, 2024Assignee: EVONIK OPERATIONS GMBHInventors: Robert Franke, Meike Roos, Horst-Werner Zanthoff, Julia Bauer, Christoph Weber, Andrea Heinroth, Jan Benedikt Metternich
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Patent number: 11806698Abstract: Systems, reactors, and processes for regenerating ionic liquid using catalyst. A plurality of tubular reactors are provided having a first end and a second end and catalyst particles disposed in the tubular reactor between the first end and the second end. A line supplies separated ionic liquid catalyst to the first end of the tubular reactor. Hydrogen is also supplied. Regenerated ionic liquid catalyst is recovered from the second end of the tubular reactor. The inner surface of the tubular reactor is preferably non-corrosive or non-reactive. A fluoropolymer lining may be used. The tubular reactors are modular, and may be changed out with the catalyst inside when the catalyst are to be replaced.Type: GrantFiled: April 30, 2021Date of Patent: November 7, 2023Assignee: UOP LLCInventors: Gregory J. Schrad, Eric Leeton, Rebecca Mudrock
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Patent number: 11760704Abstract: A system and method for coproduction in the production of ethylene, including contacting ethane with an oxidative dehydrogenation (ODH) catalyst in presence of oxygen in a first reactor to dehydrogenate ethane to ethylene, and contacting a first-reactor effluent with an ODH catalyst in a second reactor to form ethanol and acetaldehyde.Type: GrantFiled: August 17, 2020Date of Patent: September 19, 2023Assignee: NOVA Chemicals (International) S.A.Inventors: Vasily Simanzhenkov, Shahin Goodarznia
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Patent number: 11133504Abstract: A nickel complex oxide having a carbon content of 0.15% by mass or lower.Type: GrantFiled: October 25, 2018Date of Patent: September 28, 2021Assignee: SUMITOMO METAL MINING CO., LTD.Inventors: Yuji Kawakami, Tomomichi Nihei
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Patent number: 10865170Abstract: 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: GrantFiled: July 11, 2019Date of Patent: December 15, 2020Assignee: NESTE OYJInventors: Marina Lindblad, Mats Käldström, Susanna Wallenius, Kaisa Lamminpää
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Patent number: 10745330Abstract: 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: GrantFiled: July 26, 2018Date of Patent: August 18, 2020Assignee: BATTELLE MEMORIAL INSTITUTEInventors: Karthikeyan K. Ramasamy, Mond F. Guo, Michel J. Gray, Senthil Subramaniam
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Patent number: 10717692Abstract: A process for the production of 2-alkylalkanol from an aldehyde is disclosed.Type: GrantFiled: October 12, 2017Date of Patent: July 21, 2020Assignee: Johnson Matthey Davy Technologies LimitedInventors: Adrian Lord, Martin Smidt
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Patent number: 9822048Abstract: 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: GrantFiled: December 14, 2016Date of Patent: November 21, 2017Assignee: SHELL OIL COMPANYInventors: Andries Quirin Maria Boon, Joseph Broun Powell
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Patent number: 9656932Abstract: 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: GrantFiled: May 12, 2015Date of Patent: May 23, 2017Assignee: PIONEER ENERGYInventors: John T. Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
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Patent number: 9611186Abstract: 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: GrantFiled: November 8, 2012Date of Patent: April 4, 2017Assignee: PIONEER ENERGYInventors: John Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
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Patent number: 9593054Abstract: 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: GrantFiled: March 15, 2013Date of Patent: March 14, 2017Assignee: Virent, Inc.Inventors: John Kania, Paul Blommel, Elizabeth Woods, Brice Dally, Warren Lyman, Randy Cortright
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Patent number: 9567276Abstract: 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: GrantFiled: December 22, 2015Date of Patent: February 14, 2017Assignee: Evonik Degussa GmbHInventors: Florian Klasovsky, Robert Franke, Marc Becker, Thomas Quandt, Frank Geilen
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Patent number: 9388351Abstract: 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: GrantFiled: June 16, 2015Date of Patent: July 12, 2016Assignee: PHILLIPS 66 COMPANYInventors: Yun Bao, Kristi A. Fjare, Edward L. Sughrue, TiePan Shi, Brian C. Dunn, Edgar Lotero
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Patent number: 9144797Abstract: 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: GrantFiled: April 17, 2013Date of Patent: September 29, 2015Assignee: Archer Daniels Midland Co.Inventor: Chi-Cheng Ma
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Patent number: 9040757Abstract: 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: GrantFiled: March 8, 2013Date of Patent: May 26, 2015Assignee: PIONEER ENERGYInventors: John Henri, Jan Zygmunt, Mark Bergren, Robert Zubrin
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Publication number: 20150141704Abstract: 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 isType: ApplicationFiled: March 28, 2013Publication date: May 21, 2015Inventors: Walter Leitner, Jennifer Julis
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Patent number: 9023299Abstract: 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: GrantFiled: January 12, 2012Date of Patent: May 5, 2015Assignee: Davy Process Technology LimitedInventors: Edward Adrian Lord, Arthur James Reason
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Patent number: 9024089Abstract: 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: GrantFiled: November 18, 2011Date of Patent: May 5, 2015Assignee: Celanese International CorporationInventors: R. Jay Warner, Wei Qi, Tatiana H. Sonnenberg
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Patent number: 9018427Abstract: 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: GrantFiled: February 18, 2014Date of Patent: April 28, 2015Assignee: Greenyug, LLCInventors: Sagar B. Gadewar, Brian Christopher Vicente, Peter K. Stoimenov, Vivek Julka
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Patent number: 9000232Abstract: 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: GrantFiled: April 26, 2012Date of Patent: April 7, 2015Assignee: Celanese International CorporationInventors: R. Jay Warner, Victor J. Johnston, David Lee, Adam Orosco
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Patent number: 9000235Abstract: 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: GrantFiled: May 28, 2014Date of Patent: April 7, 2015Assignee: Celanese International CorporationInventors: David Lee, Lincoln Sarager, Trinity Hale, Victor J. Johnston
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Patent number: 8975450Abstract: 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: GrantFiled: March 15, 2013Date of Patent: March 10, 2015Assignee: Celanese International CorporationInventor: Mark O. Scates
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Patent number: 8975453Abstract: 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: GrantFiled: March 11, 2013Date of Patent: March 10, 2015Assignee: University of IdahoInventors: Bingjun Brian He, Randy Latayan Maglinao
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Publication number: 20150025280Abstract: 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: ApplicationFiled: December 20, 2012Publication date: January 22, 2015Applicant: Dow Global Technologies LLCInventors: Thomas P. Clark, Heather A. Spinney, Jason MacDonald, Clark H. Cummins, Jerzy Klosin, John R. Briggs
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Patent number: 8927790Abstract: 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: GrantFiled: July 12, 2012Date of Patent: January 6, 2015Assignee: Celanese International CorporationInventors: Radmila Wollrab, Victor Johnston
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Patent number: 8907143Abstract: 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: GrantFiled: July 6, 2012Date of Patent: December 9, 2014Assignee: Celanese International CorporationInventors: Radmila Wollrab, Zhenhua Zhou, Victor J. Johnston, David Lee, R. Jay Warner, Heiko Weiner
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Patent number: 8907142Abstract: 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: GrantFiled: July 6, 2012Date of Patent: December 9, 2014Assignee: Celanese International CorporationInventors: Radmila Wollrab, Zhenhua Zhou, Victor J. Johnston, David Lee, Heiko Weiner
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Patent number: 8895786Abstract: 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: GrantFiled: August 3, 2011Date of Patent: November 25, 2014Assignee: Celanese International CorporationInventors: Adam Orosco, Manuel Salado, Lincoln Sarager, R. Jay Warner, Trinity Horton
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Patent number: 8884081Abstract: 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: GrantFiled: April 26, 2011Date of Patent: November 11, 2014Assignee: Celanese International CorporationInventors: R. Jay Warner, Victor J. Johnston, David Lee, Manuel Salado, Mark O. Scates
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Patent number: 8877987Abstract: 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: GrantFiled: August 3, 2011Date of Patent: November 4, 2014Assignee: Celanese International CorportationInventors: Victor J. Johnston, David Lee, Lincoln Sarager, R. Jay Warner
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Patent number: 8859828Abstract: A process for converting a sugar, sugar alcohol, or glycerol to a valuable chemical is described. The process may use a support comprising zirconium oxide promoted by a polyacid or promoter material. A catalytically active metal may be impregnated on the polyacid-promoted zirconium oxide support and the catalyst may then be introduced the sugar, sugar alcohol, or glycerol a source of hydrogen under reaction conditions. At least 40 wt % of the sugar, sugar alcohol or glycerol may be converted to a polyol and/or a shorter carbon-chain alcohol that may include at least one of propylene glycol, ethylene glycol, glycerin, methanol, ethanol, propanol and butandiols. Specific processes for converting glycerin having a selectivity for propylene glycol and for converting sorbitol with a selectivity for propylene glycol, ethylene glycol, and/or glycerin are also described.Type: GrantFiled: March 3, 2010Date of Patent: October 14, 2014Assignee: Clariant CorporationInventors: Aiguo Liu, Wayne Turbeville, Christopher C. Luckett, Hui Hui (Faye) Li
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Publication number: 20140296584Abstract: 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: ApplicationFiled: October 24, 2012Publication date: October 2, 2014Inventors: Sadayuki Maeda, Tatsunori Sato
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Patent number: 8846988Abstract: 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: GrantFiled: April 26, 2011Date of Patent: September 30, 2014Assignee: Celanese International CorporationInventors: Radmila Jevtic, Victor Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton
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Publication number: 20140256992Abstract: 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: ApplicationFiled: March 8, 2013Publication date: September 11, 2014Applicant: PIONEER ENERGYInventors: John Henri, Jan Zygmunt, Mark Bergren, Robert Zubrin
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Publication number: 20140243526Abstract: 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: ApplicationFiled: September 27, 2012Publication date: August 28, 2014Applicant: FIRMENICH SAInventors: Philippe Dupau, Lucia Bonomo, Laurent Kermorvan
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Patent number: 8809594Abstract: 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: GrantFiled: September 21, 2012Date of Patent: August 19, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
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Patent number: 8779216Abstract: 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: GrantFiled: October 28, 2010Date of Patent: July 15, 2014Assignee: Cognis IP Management GmbHInventors: Anja Wick, Eike Ulf Mahnke
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Patent number: 8748675Abstract: 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: GrantFiled: June 16, 2011Date of Patent: June 10, 2014Assignee: Celanese International CorporationInventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
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Patent number: 8748676Abstract: 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: GrantFiled: August 3, 2011Date of Patent: June 10, 2014Assignee: Celanese International CorporationInventors: Adam Orosco, Lincoln Sarager, R. Jay Warner, Radmila Jevtic
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Patent number: 8710274Abstract: 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: GrantFiled: May 4, 2012Date of Patent: April 29, 2014Assignee: Lyondell Chemical Technology, L.P.Inventors: Daniel B Pourreau, Roger A Grey, Andrew P Kahn
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Patent number: 8704012Abstract: 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: GrantFiled: June 16, 2011Date of Patent: April 22, 2014Assignee: Celanese International CorporationInventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
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Patent number: 8704011Abstract: 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: GrantFiled: April 26, 2011Date of Patent: April 22, 2014Assignee: Celanese International CorporationInventors: Lincoln Sarager, R. Jay Warner, Trinity Horton, David Lee, Victor J. Johnston, Manuel Salado
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Publication number: 20140088326Abstract: 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: ApplicationFiled: September 21, 2012Publication date: March 27, 2014Applicant: EASTMAN CHEMICAL COMPANYInventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
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Process for recovering alcohol produced by hydrogenating an acetic acid feed stream comprising water
Patent number: 8680342Abstract: 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: GrantFiled: April 26, 2011Date of Patent: March 25, 2014Assignee: Celanese International CorporationInventors: Radmila Jevtic, Victor J. Johnston, Tianshu Pan, R. Jay Warner, Heiko Weiner, Josefina T. Chapman -
Publication number: 20140024863Abstract: 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: ApplicationFiled: January 12, 2012Publication date: January 23, 2014Applicant: DAVY PROCESS TECHNOLOGY LIMITEDInventors: Edward Adrian Lord, Arthur James Reason
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Publication number: 20130296612Abstract: 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: ApplicationFiled: May 4, 2012Publication date: November 7, 2013Applicant: LYONDELL CHEMICAL TECHNOLOGY, L.P.Inventors: DANIEL B. POURREAU, ROGER A. GREY, ANDREW P. KAHN
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Patent number: 8563787Abstract: 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: GrantFiled: October 4, 2011Date of Patent: October 22, 2013Assignee: BASF SEInventors: Christoph Stock, Dirk Gerhard, Klaus Ebel
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Publication number: 20130261348Abstract: 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: ApplicationFiled: March 28, 2012Publication date: October 3, 2013Applicant: Celanese International CorporationInventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
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Patent number: 8546621Abstract: 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: GrantFiled: August 24, 2011Date of Patent: October 1, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Johannes Tschumi, Jonathan Medlock