Ethanol Patents (Class 568/890)
  • Patent number: 9126125
    Abstract: The present invention relates to the recovery of alcohols, in particular ethanol, from a crude ethanol product obtained from the hydrogenation of acetic acid using a reduced energy process. The crude ethanol product may be fed to a distillation column in which a substantial portion of the water is removed with the acetic acid in the residue. Additional water may be removed by using a pressure swing adsorption unit, molecular sieve, and/or membrane. Ethanol extraction may also be used to reduce the ethanol concentration in the recycle streams.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: September 8, 2015
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Radmila Jevtic, David Lee, Adam Orosco, R. Jay Warner, Heiko Weiner, Zhenhua Zhou, Emily Duff
  • 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: 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: 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: 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: 8907141
    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. Unreacted acetic acid can be reduced or removed through configurations of esterification secondary reactors. The ethanol product is recovered from the residue stream.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: December 9, 2014
    Assignee: Celanese International Corporation
    Inventors: David Lee, Adam Orosco, Claudio Ribeiro, R. Jay Warner, Robert Alan Deck, Emily Duff, Victor J. Johnston
  • Patent number: 8901358
    Abstract: Ethanol production process for recovering ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. Ethanol recovery is improved by esterifying a vapor crude ethanol product to reduce unreacted acetic acid concentration.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: December 2, 2014
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton
  • 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: 8884080
    Abstract: Recovery of alcohols, in particular ethanol, from a crude ethanol product obtained from the hydrogenation of acetic acid using a reduced energy process. The crude ethanol product may be fed to a distillation column in which a substantial portion of the water is removed with the acetic acid in the residue. The ethanol product is obtained from the distillate.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: November 11, 2014
    Assignee: Celanese International Corporation
    Inventors: David Lee, Adam Orosco, Nathan Powell, Manuel Salado, Lincoln Sarager, R. Jay Warner, Trinity Horton, Radmila Jevtic, Victor J. Johnston
  • 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: 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
  • Patent number: 8802904
    Abstract: A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of first metal, a silicaceous support, and at least one 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: May 17, 2013
    Date of Patent: August 12, 2014
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmilla Wollrab
  • Patent number: 8471075
    Abstract: A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of first metal, a silicaceous support, and at least one 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: February 2, 2010
    Date of Patent: June 25, 2013
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
  • Patent number: 8415512
    Abstract: Improvements in previously disclosed methods of and apparatuses for converting alkanes, alkenes, and aromatics to olefins, alcohols, ethers, and aldehydes includes: safety improvements, use of alternative feedstocks, process simplification, improvements to the halogenation step, improvements to the reproportionation step, improvements to the solid oxide reaction, improvements to solid oxide regeneration, improvements in separations, maintenance, start-up, shut-down, and materials of construction.
    Type: Grant
    Filed: October 13, 2010
    Date of Patent: April 9, 2013
    Assignee: GRT, Inc.
    Inventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen D. Stucky, Peter C. Ford, Philip Grosso, Ashley W. Rreed, Michael F. Doherty
  • Patent number: 8318990
    Abstract: A subject for the invention is to provide a process of producing a dimeric alcohol in high yield with high selectivity by the Guerbet reaction conducted using an alcohol having 4 or less carbon atoms as a starting material in the presence of a complex including a transition metal and of a base. The invention relates to a process of producing an alcohol which includes dimerizing a starting-material alcohol having 4 or less carbon atoms in an environment having a partial hydrogen pressure of 0.1 MPa or higher.
    Type: Grant
    Filed: December 9, 2008
    Date of Patent: November 27, 2012
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yoshiyuki Tanaka, Masaru Utsunomiya
  • Publication number: 20120220796
    Abstract: A catalytic process for dehydration of an aliphatic C2-C6 alcohol to its corresponding olefin is disclosed. The process continuously flows through a reaction zone a liquid phase containing an aliphatic C2-C6 alcohol to contact a non-volatile acid catalyst at a reaction temperature and pressure to at least partially convert the aliphatic C2-C6 alcohol in the liquid phase to its corresponding olefin. The reaction pressure is greater than atmospheric pressure and the reaction temperature is above the boiling point of the olefin at reaction pressure, but below the critical temperature of the alcohol, and the olefin product is substantially in the gaseous phase. After the contacting step, the olefin containing gaseous phase is separated from the liquid phase. The invention also relates to catalytic processes such as a hydrolysis of an olefin to an alcohol, an esterification, a transesterification, a polymerization, an aldol condensation or an ester hydrolysis.
    Type: Application
    Filed: July 29, 2010
    Publication date: August 30, 2012
    Inventors: Michael Lefenfeld, Robert Hoch
  • Patent number: 8084652
    Abstract: In general, in one aspect, the invention relates to a method to convert carbon dioxide (CO2) to an alcohol. The method involves contacting a stream of flue gas comprising the CO2 from a combustion process with water mist to create a mixture of liquid carbonic acid (H2CO3) and wastewater. The method further involves extracting the liquid H2CO3 from the mixture and pressurizing the liquid H2CO3 to generate pressurized liquid H2CO3. The method further involves combining the pressurized liquid H2CO3 with a first liquid reagent in a first hydrolysis chamber creating the alcohol from combining the pressurized liquid H2CO3 with the first liquid reagent.
    Type: Grant
    Filed: September 15, 2010
    Date of Patent: December 27, 2011
    Assignee: Eco Power Solutions (USA) Corp.
    Inventor: Wayne S. Littleford
  • Patent number: 7816568
    Abstract: Catalytic reactions conducted during acid digestion of cellulose materials, including paper, a wide range of grasses including prairie grass, switch grass, pine wood sawdust, bagasse dried after sugar cane processing, cotton, waste cellulose products and starch materials, are taught for direct conversion to ethanol. The cellulose material is thoroughly wet in concentrated sulfuric acid in the presence of transition metal complexes possessing a degree of symmetry. Ethanol formed during the reaction can be removed by distillation affording a continuous process.
    Type: Grant
    Filed: December 17, 2007
    Date of Patent: October 19, 2010
    Inventor: Melvin Keith Carter
  • Publication number: 20100203607
    Abstract: Carbon-containing materials, such as biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) or coal are processed to produce useful products, such as fuels. For example, systems are described that can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy materials, to produce ethanol.
    Type: Application
    Filed: February 11, 2010
    Publication date: August 12, 2010
    Applicant: XYLECO, INC.
    Inventors: Marshall Medoff, Thomas Craig Masterman
  • Patent number: 7553397
    Abstract: A process is described for the recovery of substantially pure ethyl acetate from a feedstock including ethyl acetate, ethanol and water. The process includes supplying the feedstock to a first distillation zone maintained under first distillation conditions effective for distilling from the feedstock a first distillate including ethyl acetate, ethanol, and less than about 10 mol % water. The first distillate is recovered from the first distillation zone and is supplied to a second distillation zone maintained under second distillation conditions, which include use of a higher pressure than that of the first distillation zone. The second distillation conditions are effective for distilling from the first distillate a second distillate including ethanol, water, and a minor proportion of ethyl acetate and yielding a substantially pure ethyl acetate bottom product, which is recovered. The second distillate is returned to the first distillation zone.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: June 30, 2009
    Assignee: Davy Process Technology Limited
    Inventors: Stephen William Colley, Christopher Richard Fawcett, Mohammad Sharif, Michael William Marshall Tuck, David John Watson, Michael Anthony Wood
  • Publication number: 20080020446
    Abstract: The invention provides apparatus, reagents, and methods for rapidly isolating plasmid DNA from a bacterial alkaline lysate.
    Type: Application
    Filed: November 21, 2006
    Publication date: January 24, 2008
    Inventor: Xiyu Jia
  • Patent number: 6964728
    Abstract: Bisphenol-A-bis(neopentylglycolphosphate) products of enhanced properties and processes for preparing them are described. One of the processes includes (a) mixing and reacting neopentyl glycol and bisphenol-A-bis(dichlorophosphate) in an inert polar organic solvent which (1) if mixed by itself with an equal volume of water at 25° C., will form a separate phase, (2) the solvent by itself will dissolve at least about 10 wt % of bisphenol-A-bis(neopentylglycolphosphate) at a temperature in the range of 25 to 50° C., and optionally but preferably (3) the solvent by itself can be completely vaporized at a temperature below about 180° C.; (b) washing bisphenol-A-bis(neopentylglycolphosphate) product formed in a) while dissolved in inert organic solvent having such characteristics at least once with an aqueous alkaline washing solution; and (c) optionally but preferably, recovering bisphenol-A-bis(neopentylglycolphosphate) product from organic solvent having such characteristics.
    Type: Grant
    Filed: May 16, 2002
    Date of Patent: November 15, 2005
    Inventors: Bonnie G. McKinnie, Robert E. Williams, Gary L. Sharp, Alireza M. Dadgar
  • Patent number: 6835858
    Abstract: The invention relates to a method for the catalytic conversion of organic carbonate to the corresponding alcohol, wherein the organic carbonate is contacted with alcohol and/or water in the presence of a zinc supported catalyst.
    Type: Grant
    Filed: September 10, 2003
    Date of Patent: December 28, 2004
    Assignee: Shell Oil Company
    Inventors: Johannes Petrus De Jonge, Jean-Paul Lange
  • Patent number: 6103942
    Abstract: A process for the preparation of high purity silane, suitable for forming thin layer silicon structures in various semiconductor devices and high purity poly- and single crystal silicon for a variety of applications, is provided. Synthesis of high-purity silane starts with a temperature assisted reaction of metallurgical silicon with alcohol in the presence of a catalyst. Alcoxysilanes formed in the silicon-alcohol reaction are separated from other products and purified. Simultaneous reduction and oxidation of alcoxysilanes produces gaseous silane and liquid secondary products, including, active part of a catalyst, tetra-alcoxysilanes, and impurity compounds having silicon-hydrogen bonds. Silane is purified by an impurity adsorption technique. Unreacted alcohol is extracted and returned to the reaction with silicon. Concentrated mixture of alcoxysilanes undergoes simultaneous oxidation and reduction in the presence of a catalyst at the temperature -20.degree. C. to +40.degree. C. during 1 to 50 hours.
    Type: Grant
    Filed: April 8, 1999
    Date of Patent: August 15, 2000
    Assignee: Midwest Research Institute
    Inventors: Y. Simon Tsuo, Eugene P. Belov, Vadim G. Gerlivanov, Vitali V. Zadde, Solomonida I. Kleschevnikova, Nikolai N. Korneev, Eugene N. Lebedev, Akhsarbek B. Pinov, Eugene A. Ryabenko, Dmitry S. Strebkov, Eugene A. Chernyshev
  • Patent number: 4761505
    Abstract: According to the process of the present invention, carboxylic acids are recovered from aqueous strong acid mixtures thereof which mixtures are formed as an alcohol-depleted phase by the extraction of alcohols from aqueous strong acid solution with carboxylic acids, by contacting the mixtures with a liquid organic solvent, to form a purified aqueous strong acid stream depleted in such carboxylic acid by contacting such aqueous strong acid mixtures with a liquid organic solvent, such as an alkane, alkene or di-alkyl ether to form a purified aqueous strong acid depleted in such carboxylic acid.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: August 2, 1988
    Assignee: Exxon Research & Engineering Co.
    Inventors: William D. Diana, Chuen Y. Yeh
  • Patent number: 4760201
    Abstract: According to the process of the present invention, alcohols are recovered from aqueous mixtures thereof with a concentrated strong acid by contacting such alcohol-containing aqueous concentrated acid mixtures with a carboxylic acid selected from the group consisting of acids of the formula RCO.sub.2 H wherein R is a straight or branched-chain or cyclic alkyl of from 5 to 19 carbon atoms per molecule to form an extract phase containing the carboxylic acid in addition to said alcohol, and an aqueous raffinate phase depleted in the alcohol.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: July 26, 1988
    Assignee: Exxon Research & Engineering Co.
    Inventors: William D. Diana, David L. Wernick
  • Patent number: 4433176
    Abstract: Acetaldehyde is prepared in good yield from methanol and synthesis gas under mild reaction conditions by contacting a mixture of methanol, carbon monoxide and hydrogen with an iodide or iodine free catalyst composition comprising (1) ruthenium powder, (2) a cobalt-containing compound (3) a rhodium-containing compound, and (4) an onium salt or base, and heating the resulting mixture under mild temperature and pressure for sufficient time to produce the desired acetaldehyde, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: February 21, 1984
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4433177
    Abstract: Acetaldehyde is prepared from methanol and synthesis gas with good selectivity and yield by contacting a mixture of methanol, carbon monoxide and hydrogen with an iodide or iodine free catalyst composition comprising (1) ruthenium powder, (2) a cobalt-containing compound, (3) an amine, and (4) an onium salt or base, and heating the resulting mixture to an elevated temperature and pressure for sufficient time to produce the desired acetaldehyde, and recovering the same from the reaction mixture.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: February 21, 1984
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4433178
    Abstract: Acetaldehyde is prepared in good yield from methanol and synthesis gas by contacting the mixture of methanol, carbon monoxide and hydrogen with an iodide or iodine-free catalyst composition comprising ruthenium powder, a cobalt-containing compound and an onium salt or base, and heating the resulting mixture to an elevated temperature and pressure for sufficient time to produce the acetaldehyde, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: February 21, 1984
    Assignee: Texaco, Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4426321
    Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: January 17, 1984
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4393256
    Abstract: Alcohols may be obtained by an indirect hydration of olefinic hydrocarbons in which said olefinic hydrocarbon is esterified by treatment with an inorganic acid to form dialkyl and alkyl hydrogen salts. The esters are then hydrolyzed with water, the reconstituted acid is stripped by means of a stripping agent such as nitrogen gas, and the resulting alcohols and ethers are recovered. The alcohol production is separated from the dialkyl ether, the latter then being subjected to further treatment such as thermal decomposition and hydrolysis to form an additional amount of the desired alcohol. The reconstituted inorganic acid may be recycled for use as an esterifying agent without having to reconstitute the acid.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: July 12, 1983
    Assignee: UOP Inc.
    Inventor: Robert J. Schmidt
  • Patent number: 4348541
    Abstract: Methanol can be selectively converted to acetaldehyde, ethanol or mixtures thereof, using a homogeneous process. The process comprises contacting methanol with carbon monoxide and hydrogen in the presence of a catalytic system containing cobalt-ruthenium complexes or a soluble ruthenium compound plus Co.sub.2 (CO).sub.8-n where n is from 0 to 4.
    Type: Grant
    Filed: November 30, 1979
    Date of Patent: September 7, 1982
    Assignee: Exxon Research and Engineering Company
    Inventor: Gerald Doyle
  • Patent number: 4296261
    Abstract: A process for the manufacture of C.sub.2 -C.sub.5 alcohols from C.sub.2 -C.sub.5 olefins by the indirect hydration method is disclosed. The process comprises the steps of (a) treating a C.sub.2 -C.sub.5 olefin in an absorption zone in admixture with a C.sub.2 -C.sub.5 alkyl hydrogen sulfate at conditions to form a C.sub.2 -C.sub.5 dialkyl sulfate; (b) treating said dialkyl sulfate in a hydrolyzing zone in admixture with a measured amount of water at conditions effecting the partial hydrolysis of said dialkyl sulfate and the formation of a C.sub.2 -C.sub.5 alkyl hydrogen sulfate and a C.sub.2 -C.sub.5 alcohol; (c) separating the alcohol; and (d) recycling the alkyl hydrogen sulfate to said absorption zone, and treating said C.sub.2 -C.sub.5 olefin in admixture therewith in accordance with step (a). The practice of this invention substantially obviates the formation of sulfuric acid and the required reconcentration thereof.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: October 20, 1981
    Assignee: UOP Inc.
    Inventor: Don B. Carson