And Distilling Extractant Phase Patents (Class 203/46)
  • Patent number: 10968160
    Abstract: The present disclosure relates to a process for producing high-purity acrylic acid using azeotropic distillation and using water as an entrainer. This disclosure provides a process for separating acrylic acid from recovered feed streams which comprise acrylic acid and saturated organic acids including propionic acid. The resulting acrylic acid product is of sufficient purity to produce acrylate esters and high molecular weight acrylic acid polymers.
    Type: Grant
    Filed: December 15, 2017
    Date of Patent: April 6, 2021
    Assignee: Eastman Chemical Company
    Inventors: Craig Alan Hoyme, Joseph Jerome Puhr, Robert Sterling Kline
  • Patent number: 8993825
    Abstract: An aromatics complex producing one or more xylene isomers offers a large number of opportunities to conserve energy by heat exchange within the complex. One previously unrecognized opportunity is through providing two parallel distillation columns operating at different pressures to separate C8 aromatics from C9+ aromatics. The parallel columns offer additional opportunities to conserve energy within the complex through heat exchange in associated xylene recovery facilities.
    Type: Grant
    Filed: May 21, 2014
    Date of Patent: March 31, 2015
    Assignee: UOP LLC
    Inventors: Gregory R. Werba, Jason T. Corradi, Xin X. Zhu, David W. Ablin, Saadet Ulas Acikgoz, Phillip F. Daly
  • Publication number: 20150005539
    Abstract: A method for removing a contaminant from a hydrochlorofluoroolefin (such as trans-1,1,1-trifluoro-3-chloro-2-propene (1233zd(E))) includes extracting a chlorofluorocarbon (such as trichlorofluoromethane (R11)) from a mixture comprising the hydrochlorofluoroolefin and the chlorofluorocarbon using extractive distillation in the presence of an extractive solvent comprising a chlorinated compound to form a purified hydrochlorofluoroolefin. This separation method provides for removal of a contaminant, such as R11, from a hydrochlorofluoroolefin, such as 1232zd(E), which are not separable by conventional distillation methods. The method may employ a process utilizing two distillation columns, for example, a first extractive distillation column and a second solvent recovery column, which allows for recycle of the extractive solvent to the first extractive distillation column.
    Type: Application
    Filed: February 22, 2013
    Publication date: January 1, 2015
    Inventor: John A. Wismer
  • Patent number: 8734617
    Abstract: Processes comprising: (a) reacting dimethylamine and ethylene oxide to form a product mixture comprising N,N-dimethylethanolamine and N,N-dimethylaminoethoxyethanol; (b) distilling the product mixture to obtain a bottom fraction comprising N,N-dimethylaminoethoxyethanol; and (c) distilling the bottom fraction to separate at least a portion of the N,N-dimethylaminoethoxyethanol from the bottom fraction; and apparatus for carrying out said processes.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: May 27, 2014
    Assignee: BASF SE
    Inventors: Frank-Friedrich Pape, Alfred Krause, Johann-Peter Melder, Bernd Stein, Joachim-Thierry Anders, Frank Haese
  • Patent number: 8608912
    Abstract: Embodiments of extraction unit and an analysis method are provided. In one embodiment, the analysis method includes the steps of providing a feed stream and a species-selective solvent to the distillation column, drawing a vapor sample from the distillation column, condensing the vapor sample, and analyzing at least a portion of the condensed vapor sample.
    Type: Grant
    Filed: September 29, 2010
    Date of Patent: December 17, 2013
    Assignee: UOP LLC
    Inventors: Jason L. Noe, Ian Horn, Lars Sullivan, Bruce R. Beadle, Edward M. Casey, James W. Harris
  • Patent number: 8518219
    Abstract: Organic waste disposal technologies are disclosed herein. A multistage processing of sewage sludge into synthetic fuel and chemical products is carried out by means of a direct thermo-chemical liquefaction process. The process enables the minimization of coke formation by utilizing steam stripping in the processing of sewage sludge.
    Type: Grant
    Filed: January 1, 2009
    Date of Patent: August 27, 2013
    Assignee: Metal Tech Ltd.
    Inventors: Yefim Plopski, Alexander Rogov
  • Patent number: 8506766
    Abstract: A method for recovering acetic acid from an aqueous feed stream containing acetic acid and, in particular, a stream generated during terephthalic acid production includes feeding a water-rich feed stream to a liquid-liquid extraction column, which includes a guard bed near the top thereof for conversion of alcohol within the feed stream by reaction with acetic acid to the corresponding ester, and removing residual water from acetic acid in an azeotropic distillation column by feeding water-poor feed streams from the extraction column to the distillation column at a height at which the mixture has a similar water concentration. The liquid-liquid extraction column produces an extract of an extraction solvent and acetic acid which is sent to the azeotropic distillation column to separate residual water and acetic acid.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: August 13, 2013
    Assignee: AMT International Inc.
    Inventors: Kuang-Yeu Wu, Ji-Young Jang, Karl Tze-Tang Chuang
  • Patent number: 8382961
    Abstract: The invention disclosed is an apparatus and method for the recovery of acetic acid, azeotropic agent, extraction agent, re-usable water and other reaction products such as p-toluic acid, from an aqueous stream generated during a terephthalic acid production process, having superior energy efficiency and reduced water consumption.
    Type: Grant
    Filed: June 7, 2010
    Date of Patent: February 26, 2013
    Assignee: AMT International, Inc.
    Inventors: Ji-Young Jang, Kuang-Yeu Wu, Ming-Mou Yang
  • Publication number: 20120285816
    Abstract: The invention relates to the isolation of an alkanol from an aqueous biotransformation mixture, in that a) a first alkanol phase is obtained by means of distilling out an alkanol-water azeotrope from the aqueous biotransformation mixture and, if the azeotrope is a heteroazeotrope, phase separating the azeotrope and separating out an aqueous phase, b) a second alkanol phase is obtained by (i) liquid/liquid extracting the first alkanol phase using a solvent as an extracting agent, or (ii) azeotropic drying the first alkanol phase in the presence of the solvent as a carrier agent, and c) the second alkanol phase is fractionally distilled, producing a pure alkanol fraction. The biotransformation mixture is obtained, for example, by means of reducing an alkanol in the presence of an alcohol dehydrogenase. The method is adapted to the severe dilution of the products of value in the biotransformation mixture and works without long phase separation times when extracting by means of organic solvents.
    Type: Application
    Filed: November 24, 2010
    Publication date: November 15, 2012
    Applicant: BASF SE
    Inventors: Jürgen Däuwel, Michael Breuer, Bernhard Hauer
  • Publication number: 20120090981
    Abstract: This invention relates to processes for producing acetic acid and, in particular, to improved processes for recovering C2+ alkyl halides and removing permanganate reducing compounds formed during the carbonylation of methanol in the presence of a Group VIII metal carbonylation catalyst to produce acetic acid.
    Type: Application
    Filed: October 13, 2011
    Publication date: April 19, 2012
    Applicant: Celanese International Corporation
    Inventors: G. Paull Torrence, Raymond Zinobile, Oyeyemi Oyerinde
  • Patent number: 8057643
    Abstract: A process recovers of pyridine and/or its derivatives from their aqueous mass and/or manufacturing reaction mass by liquid-liquid extraction employing an alkyl acetate. The process further involves effective recovering and recycling of solvents from the aqueous phase and other waste obtained during the process.
    Type: Grant
    Filed: November 17, 2006
    Date of Patent: November 15, 2011
    Assignee: Jubilant Organosys Limited
    Inventors: Mahendra Kumar, Sanjeev Kumar Dixit, Shailendra Kumar Singh, Ashutosh Agarwal
  • Publication number: 20110220483
    Abstract: The invention describes a global method for extracting sterols, vitamin E, squalene and other vegetable hydrocarbons from deodorization distillates of vegetable oils. After esterification of the free fatty acids, followed by trans-esterification of the combined fatty acids (glycerides and sterides) with the same short alcohol, three successive distillations allow successive recovery of a first fraction of the hydrocarbons, the main fraction of alkyl esters, and then the heaviest alkyl esters with squalene. The third distillate will be used for producing squalene and a second fraction of hydrocarbons. The residue of the third distillation will be used for producing sterols and vitamin E. By using bio-ethanol, vegetable glycerol and the vegetable hydrocarbons of the method, with the method it is possible to extract each of the four unsaponifiables without any solvent of petroleum origin and claim the labels of products obtained by natural physical and chemical methods.
    Type: Application
    Filed: July 2, 2009
    Publication date: September 15, 2011
    Inventors: Jacques Margnat, Georges Cecchi, Olivier Guillon
  • Publication number: 20110168541
    Abstract: A method of treating a coal-derived liquid byproduct from a coal gasification process includes subjecting the coal-derived liquid to a vacuum distillation process, thereby separating the coal-derived liquid into condensed gas and coal-derived liquid bottoms. The coal-derived liquid bottoms are mixed with a bottoms solvent capable of dissolving the coal-derived liquid bottoms. The solvent/bottoms mixture is introduced along with a linear chain hydrocarbon solvent into a liquid extractor. The Raffinate is separated from the solvent for the coal-derived liquid/bottoms mixture, thereby producing in a heavy extract. The condensed gas is subjected to atmospheric distillation producing a bottoms fraction and another condensed fraction. The bottoms fraction may be used as fuel or for diesel fuel production. The condensed fraction is extracted with a linear hydrocarbon solvent in an extractor to produce light neutral oil and a Raffinate which is a cresylic acid feed stock.
    Type: Application
    Filed: March 23, 2011
    Publication date: July 14, 2011
    Inventors: James S. Warwick, James P. Frederick
  • Publication number: 20090223805
    Abstract: Processes comprising: (a) reacting dimethylamine and ethylene oxide to form a product mixture comprising N,N-dimethylethanolamine and N,N-dimethylaminoethoxyethanol; (b) distilling the product mixture to obtain a bottom fraction comprising N,N-dimethylaminoethoxyethanol; and (c) distilling the bottom fraction to separate at least a portion of the N,N-dimethylaminoethoxyethanol from the bottom fraction; and apparatus for carrying out said processes.
    Type: Application
    Filed: March 20, 2007
    Publication date: September 10, 2009
    Applicant: BASF Aktiengesellschaft
    Inventors: Frank-Friedrich Pape, Alfred Krause, Johann-Peter Melder, Bernd Stein, Joachim-Thierry Anders, Frank Haese
  • Patent number: 7563360
    Abstract: A top temperature T1 of a distillation tower 1 is held below a liquefying temperature of a light fraction by returning a part of an exhaust gas W, which is cooled by a condenser 5, to the upper zone of the distillation tower 1. A bottom temperature T2 is raised up to 300° C. at highest by returning a part of a liquid product P from a re-boiler 3 to a lower zone of the distillation tower 1. When a liquid hydrocarbon L comes in countercurrent contact with a stripping gas G inside the distillation tower 1 with the temperature profile that an inner temperature gradually falls down along an upward direction, mercury is efficiently transferred from the liquid L to a vapor phase without effusion of the light fraction in accompaniment with the exhaust gas W.
    Type: Grant
    Filed: January 26, 2005
    Date of Patent: July 21, 2009
    Assignee: Japan Petroleum Exploration Co., Ltd.
    Inventors: Yoshiyuki Yamaguchi, Senichiro Kaku, Kazutoshi Chaki
  • Patent number: 7241365
    Abstract: The invention relates to an apparatus and a process for the preparation of anhydrous or substantially anhydrous formic acid. This apparatus is constructed partly or entirely of substantially zirconium-free materials. The extractant employed is a liquid of the general formula I where the radicals R1 and R2 are alkyl, cycloalkyl, aryl or aralkyl groups, or R1 and R2 jointly, together with the N atom, form a heterocyclic 5- or 6-membered ring, and only one of the radicals is an aryl group, and where R3 is hydrogen or a C1–C4-alkyl group. The apparatus has a synthesis reactor (6), a hydrolysis reactor (1), three distillation devices (2,4,5) and an extraction device (3).
    Type: Grant
    Filed: January 24, 2001
    Date of Patent: July 10, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Gerhard Wagner, Till Adrian
  • Patent number: 6712942
    Abstract: A mixture (M1) comprising an alkene and oxygen is worked up by a process in which (i) oxygen is removed from the mixture (M1) by a nondistillative method to give a mixture (M2) and (ii) the alkene is separated off from the mixture (M2) by distillation.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: March 30, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Alwin Rehfinger, Peter Bassler, Norbert Rieber, Werner Hefner, Anne Wenzel, Peter Rudolf
  • Patent number: 6695952
    Abstract: A method for the separation and purification of an aqueous mixture of main components, namely acetic acid and formic acid and non-volatiles by extraction, uses a solvent in a circulatory system. A raffinate stream is mixed with the larger proportion of water from a solvent stripper column (11) for the removal of water. The extraction stream is introduced into a solvent distillation column (8), from which in a first step involving the use of a mixture (A) containing a larger proportion of the solvent is separated out via a header and a mixture (B) of formic acid, water and solvent is separated out via a side offtake and a mixture (C) of acetic acid and non-volatiles is also separated out. A mixture (B) is introduced into a formic acid distillation column (4) for further processing, and a mixture (C) is introduced into an acetic acid distillation column (5), and purified acetic acid is subsequently isolated in the acetic acid distillation column (5) from the header.
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: February 24, 2004
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Christoph Rüdinger, Harald Herbert Voit, Michael Hallmann, Mehmet Günaltay, Barbara Geborene Neé Reil Wild, Hans Jürgen Eberle
  • Patent number: 6623604
    Abstract: Methods of recovering free fatty acids having a low ester content from alkanol-containing solutions and oil mixtures containing tocopherols are disclosed which involve atmospheric or vacuum stripping at low temperatures. The recovered fatty acids have a high acid value, and have high commercial value in the production of high quality (high acid value) products, e.g., dimerized fatty acids, useful in polyamide resins.
    Type: Grant
    Filed: June 5, 2000
    Date of Patent: September 23, 2003
    Assignee: Cognis Corporation
    Inventors: A. Fred Elsasser, C. William Blewett
  • Publication number: 20030121768
    Abstract: A process for the separation and purification of acrylic acid is disclosed, wherein ethyl propionate is employed as an extraction solvent.
    Type: Application
    Filed: December 13, 2001
    Publication date: July 3, 2003
    Inventors: Salvador Aldrett Lee, Diane Elizabeth Allen, Christopher Lawrence Wilkins
  • Patent number: 6514387
    Abstract: The invention relates to a rectifying column for extractive distillation, comprising a column main section (204) and a raffinate section (205) above said main section, an evaporator (208) situated on the lower end of the column, an inlet (214) disposed between the main section of the column and the raffinate section and a solvent inlet (215) arranged on the top side of the raffinate section (205) for feeding an extracting agent. According to the invention, the main section (204) has two chambers (216, 217) connected in parallel. A stripping section (222) is disposed between the bottom of the column (221) and the main section (204), in which concentration of the extracting agent occurs from the top down. The bottom (221) is connected to the solvent inflow (215) by a device (223) for recycling the extracting agent.
    Type: Grant
    Filed: August 1, 2000
    Date of Patent: February 4, 2003
    Assignee: Krupp Uhde GmbH
    Inventors: Gerd Emmrich, Bärbel Kolbe, Helmut Gehrke, Frank Ennenbach, Uwe Ranke
  • Patent number: 6488818
    Abstract: A process for removing impurities from 3-(2′-acetoxyethyl)dihydro-2(3H)furanone (I), where the 3-(2′-acetoxyethyl)dihydro-2(3H)furanone containing the undesirable impurities is initially prepared in a manner known per se by acetylation of 3-(2′-hydroxyethyl)dihydro-2(3H)furanone and the resulting product is subsequently subjected to a distillation or rectification, includes carrying out the distillation or rectification in a plurality of steps, where high-boiling impurities are removed in a first step, the product which is drawn off via the top is subsequently subjected to at least one further step in which low-boilers and intermediate boilers are drawn off via the top and the desired pure I is obtained as bottom product.
    Type: Grant
    Filed: September 8, 1999
    Date of Patent: December 3, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Maywald, Horst Hartmann, Norbert Götz, Gernot Reissenweber, Hartmann König
  • Patent number: 6294055
    Abstract: Process for the separation of hydrogen fluoride from its mixtures with a hydrofluoroalkane containing from 3 to 6 carbon atoms, by extraction using an organic solvent.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: September 25, 2001
    Assignee: Solvay S.A.
    Inventors: Ralf Herkelmann, Carsten Brosch, Vincent Wilmet
  • Publication number: 20010004961
    Abstract: Process for the separation of hydrogen fluoride from its mixtures with a hydrofluoroalkane containing from 3 to 6 carbon atoms, by extraction using an organic solvent.
    Type: Application
    Filed: September 11, 1998
    Publication date: June 28, 2001
    Inventors: RALF HERKELMANN, CARSTEN BROSCH, VINCENT WILMET
  • Patent number: 6210583
    Abstract: A process for pre-treating a spent caustic stream prior to oxidation which includes countercurrent multi-stage elevated temperature solvent extraction of dissolved organic material from the spent caustic using a solvent to yield a spent caustic raffinate containing only residual amounts of organic solute and steam distilling the spent caustic raffinate to remove the residual organic solutes, yielding a pretreated spent caustic stream substantially free of organic material which is then subjected to wet air oxidation and thereafter to ozonolysis to yield a wastewater stream having a low COD and BOD, which is neutralized to a pH of 8.5 to 9.0.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: April 3, 2001
    Assignee: Stone & Webster Engineering
    Inventors: Sabah A. Kurukchi, Joseph M. Gondolfe, Stephen Z. Masoomian
  • Patent number: 6193837
    Abstract: A process for producing a brightness stabilization mixture of water-soluble organic compounds from biomass pyrolysis oils comprising: a) size-reducing biomass material and pyrolyzing the size-reduced biomass material in a fluidized bed reactor; b) separating a char/ash component while maintaining char-pot temperatures to avoid condensation of pyrolysis vapors; c) condensing pyrolysis gases and vapors, and recovering pyrolysis oils by mixing the oils with acetone to obtain an oil-acetone mixture; d) evaporating acetone and recovering pyrolysis oils; e) extracting the pyrolysis oils with water to obtain a water extract; f) slurrying the water extract with carbon while stirring, and filtering the slurry to obtain a colorless filtrate; g) cooling the solution and stabilizing the solution against thermally-induced gelling and solidification by extraction with ethyl acetate to form an aqueous phase lower layer and an organic phase upper layer; h) discarding the upper organic layer and extracting the aqueous
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: February 27, 2001
    Assignee: Midwest Research Institute
    Inventors: Foster A. Agblevor, Serpil Besler-Guran
  • Patent number: 6143856
    Abstract: A phenolic-rich pyrolysis oil is produced by pyrolysing lignocellulosic material at a temperature of no more than about 550.degree. C under an absolute pressure of no more than about 50 kPa to produce pyrolysis vapors, and condensing the pyrolysis vapors to obtain a condensate consisting of a phenolic-rich pyrolysis oil having a dew point of about 65 to about 75.degree. C. under an absolute pressure of about 15 to about 20 kPa. Such a phenolic-rich pyrolysis can be directly used in making phenol-formaldehyde resol resins.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: November 7, 2000
    Assignee: Pyrovac Technologies Inc.
    Inventors: Christian Roy, Xiao Lu, Hooshang Pakdel
  • Patent number: 6096673
    Abstract: An improved process is provided for the recovery of catalyst components from oligomeric impurities which are formed during the industrial preparation of 2,5-dihydrofuran by the catalytic isomerization of vinyl oxirane followed by an essential separation of the oligomeric by-products which otherwise cause deactivation of the catalyst. The catalyst components consist essentially of (a) an onium iodide and (b) a Lewis acid selected from the group consisting of the chloride, bromide or iodide of the metals zinc, tin, cobalt and bismuth, preferably zinc, where the catalyst optionally includes a donor ligand.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: August 1, 2000
    Assignee: BASF Aktiengesellschaft
    Inventor: Martin Fischer
  • Patent number: 6015477
    Abstract: Highly purified ammonia for use in processes for the production of high-precision electronic components is prepared on-site by drawing ammonia vapor from a liquid ammonia reservoir, passing the vapor through a filter capable of filtering out particles of less than 0.005 micron in size, and scrubbing the filtered vapor in a high-pH aqueous scrubber.
    Type: Grant
    Filed: May 22, 1998
    Date of Patent: January 18, 2000
    Assignee: Air Liquide America Corporation
    Inventors: Joe G. Hoffman, R. Scot Clark
  • Patent number: 5885422
    Abstract: A process for pretreating a spent caustic stream prior to oxidation includes countercurrent multi-stage elevated temperature solvent extraction of dissolved organic material from the spent caustic using a solvent to yield a spent caustic raffinate containing only residual amounts of organic solute. The raffinate is steam distilled to remove the residual organic solutes, yielding a pretreated spent caustic stream substantially free of organic material. The pretreated spent caustic is suitable for use in a Kraft paper process or for oxidation prior to recycle or disposal. Solvent extract from the extractor is regenerated in a solvent regenerator having an overhead stream for purging light ends, a bottom stream for purging heavy ends, and a heart-cut side stream for recycling solvent to the extractor.
    Type: Grant
    Filed: February 26, 1997
    Date of Patent: March 23, 1999
    Assignee: Stone & Webster Engineering Corporation
    Inventors: Sabah A. Kurukchi, Joseph M. Gondolfe
  • Patent number: 5811598
    Abstract: Phenol dissolved in an aqueous sulphatic stream discharged from a reactor in which cumene hydroperoxide is oxidized to phenol and acetone is recovered by extracting phenol present in said aqueous sulphatic stream containing phenol, Na.sub.2 SO.sub.4 and organic impurities, in a multi-step extractor with an organic solvent, thereby forming an extracted product organic phase and a refined aqueous product phase, the ratio of the extracted product phase to the refined product phase ranging from 0.1 to 1 v/v at a temperature ranging from 20.degree.-70.degree. C., and obtaining phenol by distillation or re-extraction of the recovered extracted product organic phase.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: September 22, 1998
    Assignee: Enichem S.p.A.
    Inventors: Vanni Alessi, Sabrina Astori, Francesco Celin, Cecilia Gradella, Renzo Penzo
  • Patent number: 5811597
    Abstract: Methyl tertiary butyl ether is prepared from contaminated TBA by reactively distilling the contaminated TBA in a reactive distillation column to provide a lower boiling isobutylene fraction and a higher boiling aqueous TBA fraction, by distilling the higher boiling aqueous TBA fraction to provide a lower boiling TBA fraction, by charging the lower boiling isobutylene fraction, the lower boiling tertiary butyl alcohol fraction and methanol to an etherification reactor to form an etherification reaction product, by distilling the etherification reaction product to provide a lower boiling fraction containing isobutylene, methanol and methyl tertiary butyl ether by charging the lower boiling fraction to a finishing reactor to react the isobutylene and methanol contained therein to from additional MTBE and by recovering MTBE from the etherification reaction product and the isobutylene conversion product.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: September 22, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Rei-Yu Judy Hwan, Mark Elliott Taylor, John Frederick Knifton, Melvin Ernest Stockton, John Ronald Sanderson
  • Patent number: 5763695
    Abstract: 3-Methyl-1-butanol cannot be separated from 1-pentanol by distillation or rectification because of the closeness of their boiling points. 3-Methyl-1-butanol is readily separated from 1-pentanol by extractive distillation. Effective agents are butyl benzoate, 2-undecanone and diethylene glycol methyl ether.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: June 9, 1998
    Inventor: Lloyd Berg
  • Patent number: 5763694
    Abstract: 3-Methyl-1-butanol cannot be separated from 1-pentanol by distillation or rectification because of the closeness of their boiling points. 3-Methyl-1-butanol is readily separated from 1-pentanol by azeotropic distillation. Effective agents are methylcyclohexane, methyl formate and tetrahydrofuran.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: June 9, 1998
    Inventor: Lloyd Berg
  • Patent number: 5744010
    Abstract: The invention relates to a process for the preparation of acesulfam salts by reaction of salts of amidosulfonic acid with diketene to give a salt of acetoacetamidosulfonic acid (I), ring closure by the action of at least about an equivalent amount of SO.sub.3, at least this ring closure reaction being carried out in the presence of a halogenated, aliphatic hydrocarbon as an inert solvent, treatment of the cyclization product with water and conversion of the resulting acesulfam-H (II) into the form of a non-toxic salt, which comprises, in the work-up by distillation of the resulting crude solvent, after removal of water and low-boilers and recovery of solvent sufficiently pure for reuse in the preparation of compounds (I) and/or (II), directly returning :he remaining, solvent-containing distillation residue, without further purification, into the system downstream of the reaction vessel for carrying out the ring closure reaction.
    Type: Grant
    Filed: June 19, 1995
    Date of Patent: April 28, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Roscher, Heinz Litterer, Axel Engelmann, Wolf-Dietmar Kaufmann, Bernd Laugwitz, Hans-Dietmar Schnabel
  • Patent number: 5565068
    Abstract: In the multistage distillation of a methyl tertiary butyl ether reaction product comprising methyl tertiary butyl ether, tertiary butyl alcohol, methanol, isobutylene and water, the methyl tertiary butyl ether reaction product is separated in a primary methyl tertiary butyl ether distillation column into a lower boiling methyl tertiary butyl ether fraction and a higher boiling aqueous tertiary butyl alcohol fraction; the lower boiling aqueous tertiary butyl alcohol fraction is separated in a tertiary butyl alcohol distillation column into a vaporized overhead tertiary butyl alcohol fraction and a higher boiling water fraction; cooling water is charged to the reflux condenser for the tertiary butyl alcohol distillation column to liquify the vaporized, overhead tertiary butyl alcohol fraction and to convert the cooling water to wet steam, and the wet steam is independently charged to the reboiler for the primary methyl tertiary butyl ether distillation zone to supply the heat necessary for the distillation to b
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: October 15, 1996
    Assignee: Texaco Development Corporation
    Inventors: Stuart J. Parker, Arlen G. Sliger, Rei-Yu J. Hwan
  • Patent number: 5447607
    Abstract: Process equipment is provided for separating ether, alcohol and hydrocarbon components from various etherifications of C.sub.4 or C.sub.5 isoolefins with an alcohol such as methanol or ethanol, and wherein identical process vessels are utilized for recovery of MTBE, ETBE, TAME, or TAEE. In use the process vessels are serially arranged in three zones. The first zone includes a first water wash vessel followed by a first fractionator and provides the ether product, the second zone includes a second wash vessel followed by a hydrocarbon stripper and recovers a stabilized hydrocarbon stream, the third zone includes a second fractionator which recovers an alcohol suitable for recycling.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: September 5, 1995
    Assignee: Phillips Petroleum Company
    Inventors: John H. Eason, Joseph Klepac
  • Patent number: 5409579
    Abstract: Disclosed is a method and apparatus for recovering acetic acid from an acetic acid/water waste stream which includes a dehydration column into which the stream is fed and a liquid-liquid extraction system for recovering acetic acid from the condensate of the overhead stream of the dehydration column. Optionally, low pressure and/or high pressure absorber systems are provided to process vapor and/or liquid streams associated with the recovery system and/or the plant in which the acetic acid is used to further the recovery of acetic acid and reduce atmospheric pollution.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: April 25, 1995
    Assignee: Glitsch, Inc.
    Inventors: Ronald G. Gualy, Wiston Lamshing, Joseph C. Gentry, Fernando Varela
  • Patent number: 5348624
    Abstract: For separating ETBE and ethanol the following principal stages are employed:(1) Extraction of ethanol by water, the raffinate being ETBE saturated in water and the extract an ethanol/water mixture containing a small proportion of ETBE;(2) Concentration of the above mixture, the distillate being a mixture close to the ethanol/water azeotrope in composition and containing a very small proportion of ETBE;(3) Heteroazeotropic distillation of this distillate in two coupled columns with an overhead decanter, this distillation using ETBE as azeotroping agent; the residue of the first column being ethanol which is ca. 99% by mole and the residue of the second column being practically pure water, this water and the water recovered during the concentration stage being used as extraction solvent in stage (1).Stage (3) may be an ethanol dehydration unit using ETBE as dehydrating agent.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: September 20, 1994
    Assignee: Institut Francais du Petrole
    Inventors: Annick Pucci, Paul Mikitenko, Massimo Zuliani
  • Patent number: 5215630
    Abstract: The present invention provides a continuous method of purifying eicosapentaenoic acid and esters of eicosapentanoic acid, comprising (a) fractionally distilling a starting mixture containing eicosapentaenoic acid or esters of eicosapentaenoic acid using a system of at least three distillation columns connected in flow arrangement to separate a fraction containing eicosapentaenoic acid or esters of eicosapentaenoic acid and other C.sub.20 fatty acids from a fraction containing lower-number carbon fatty acids and from a fraction containing higher-number carbon fatty acids, and (b) continuously collecting the fraction containing eicosapentaenoic acid or esters of eicosapentaenoic acid, wherein the pressure in the distillation columns is maintained at 10 Torr or below and wherein the bottom temperature of the distillation columns is maintained at 210.degree. C. or below.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: June 1, 1993
    Assignees: Nippon Suisan Kaisha, Ltd., Kansai Chemical Engineering Co., Ltd.
    Inventors: Kazuhiko Hata, Hideo Noda, Masahiro Makuta
  • Patent number: 5076896
    Abstract: A process for the separation of propylene glycol from a mixture of low-boiling fatty alcohols and propylene glycol which comprises extracting the mixture with water to produce a water-propylene glycol mixture and fractionating the water-propylene glycol mixture to produce propylene glycol that is substantially anhydrous and an apparatus for carrying out the process.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: December 31, 1991
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Franz-Josef Carduck, Lutz Jeromin, Gerd Geobel, Wilhelm Johannisbauer, Georg Fieg, Theo Fleckenstein
  • Patent number: 5057192
    Abstract: Disclosed is an improved process for the removal of acetone from a production system wherein acetic anhydride is produced by contacting a mixture containing methyl iodide and methyl acetate and/or dimethyl ether with carbon monoxide in the presence of a carbonylation catalyst or catalyst system. The process involves a water-methyl iodide extraction step wherein acetone is separated from a mixture of methyl acetate, methyl iodide and acetone.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: October 15, 1991
    Assignee: Eastman Kodak Company
    Inventors: Joseph R. Zoeller, Steven L. Cook, Charles E. Outlaw, Robert M. Schisla, Jr.
  • Patent number: 4997547
    Abstract: In the method for the production of an aromate concentrate suitable for use as blending component for gasifier fuel, feed hydrocarbon mixtures having boiling ranges substantially between 40.degree. and 170.degree. C., are subjected, without any previous separation into individual fractions, to an extractive distillation employing N-substituted morpholine, substituents of which display no more than seven C-atoms, as selective solvent. Herewith, the lower boiling non-aromates with a boiling range up to about 105.degree. C., practically completely, and most of the higher boiling non-aromates with a boiling range between about 105.degree. and 160.degree. C., are recovered as raffinate, whereas the aromates, which are to be employed in whole or in part as blending component, come down in the extract of the extractive distillation.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: March 5, 1991
    Assignee: Krupp Koppers GmbH
    Inventors: Gerd Emmrich, Bernhard Firnhaber, Martin Schulze
  • Patent number: 4902385
    Abstract: Practically anhydrous crude sec-butyl alcohol produced by catalytic direct hydration of n-butenes is freed by means of water from the azeotropically boiling and low-boiling by-products by continuous azeotropic distillation in a separation column, the prepurified anhydrous sec-butyl alcohol obtained is withdrawn and the high-boiling by-products are subsequently separated in a separate column.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: February 20, 1990
    Assignee: Deutsche Texaco Aktiengesellschaft
    Inventor: Gunther Osterburg
  • Patent number: 4886581
    Abstract: By extracting hydrogen fluoride from 2,2,3,3-tetrafluorooxetane with a halogenated hydrocarbon, a mixture of 2,2,3,2-tetrafluorooxetane and the halogenated hydrocarbon containing a small amount of hydrogen fluoride is obtained. The mixture may be distilled at least twice to obtain a mixture of 2,2,3,2-tetrafluorooxetane and the halogenated hydrocarbon containing substantially no hydrogen fluoride.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: December 12, 1989
    Assignee: Daikin Industries Ltd.
    Inventors: Yohnosuke Ohsaka, Shoji Takaki, Hiroo Sakai
  • Patent number: 4836896
    Abstract: Meta- and para-diisopropylbenzenes cannot be easily separated from each other by distillation because of the closeness of their vapor pressures. m-Diisopropylbenzene can be readily removed from p-diispropylbenzene by azeotropic distillation using acetophenone. The acetophenone - m-diisopropylbenzene azeotrope can be separated by solvent extraction with propylene glycol to remove the acetophenone and the propylene glycol - acetophenone mixture is readily separated from each other by rectification.
    Type: Grant
    Filed: January 9, 1989
    Date of Patent: June 6, 1989
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 4769112
    Abstract: A method and apparatus for removing water from a liquid mixture of water and ethanol contacts it with liquid carbon dioxide so that the ethanol is preferentially transferred into solution, dries the solution using an adsorbent, and then recovers dry ethanol by distilling off the carbon dioxide. This process is particularly energy efficient especially when it includes a fermentation process to generate the ethanol and uses the carbon dioxide generated during the fermentation as the source of liquid carbon dioxide. In this case the method and apparatus provide an additional product of dry carbon dioxide.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: September 6, 1988
    Assignee: United Distillers P.L.C.
    Inventor: Alfred G. Wheldon
  • Patent number: 4764256
    Abstract: A method is provided for continuous removal of polychlorinated biphenyl compounds (PCB) from oil contaminated therewith, comprising the steps of continuously extracting PCB compounds from contaminated oil with a PCB-selective solvent in the stripping section of a multistage extraction zone, partially distilling the extract from the extraction zone in a distillation zone, cooling and separating the bottom residue into a solvent phase and an oil/PCB phase, continuously recycling a major portion of the oil/PCB phase as extract reflux to the enriching section of the extraction zone where PCB compounds are extracted from the recycled portion by the solvent phase produced in the stripping section of the extraction zone to increase the PCB content of the extract, and withdrawing a minor portion of the oil/PCB phase from the separation step as a disposable PCB residue.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: August 16, 1988
    Assignee: Electric Power Research Institute, Inc.
    Inventor: Peter F. Way
  • Patent number: 4740273
    Abstract: A process for purifying diethoxymethane from a mixture containing ethanol and, optionally, water. The process involves the addition of an amount of water, DEM, or an appropriate mixture of any two or three of water, DEM and ethanol that is effective in moving the mixture into the two liquid phase region on an equilibrium tie-line which crosses the critical distillation boundary without the need for additional azeotrope-forming agents such as cyclohexane.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventors: Daniel L. Martin, Peter W. Raynolds
  • Patent number: 4615771
    Abstract: A method for the separation of bis-(2-aminoethyl)ether from N-(2-methoxyethyl)morpholine via azeotropic distillation using an entrainer such as monoethanolamine is described. The N-(2-methoxyethyl)morpholine is selectively removed by the monoethanolamine. The N-(2-methoxyethyl)morpholine is then separated from the monoethanolamine by liquid-liquid extraction using a non polar hydrocarbon or aromatic extraction solvent and distillation.The N-(2-methoxyethyl)morpholine-monoethanolamine stream previously had no economic use. The separation is now economically effected and the N-(2-methoxyethyl)morpholine used as a polyurethane catalyst.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: October 7, 1986
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Roger G. Duranleau