Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are dipentene, anisole and ethyl benzene.
Abstract: 3-Methyl-2-butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 2-pentanol by azeotropic distillation. Effective agents are 2,2-dimethyl butane, ethyl acetate and dioxane.
Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are sec. butyl acetate, hexene-1 and 1,3-dioxolane.
Abstract: A distillation process is used to separate methanol from a mixture of methanol with methyl acrylate or methyl methacrylate, as well as from a mixture of methanol and water with methyl acrylate or methyl methacrylate with the use of an azeotropic solvent, which forms an azeotropic mixture with methanol. In distilling such a mixture by the use of a distillation column:(1) part of the condensate of vapors distilled over from the top of the distillation column top is returned to the top of the column;(2) the remaining condensate is separated into two layers;(3) the upper layer essentially composed of an azeotropic solvent from the two separated layers is fed to an intermediate portion of the distillation column;(4) the lower layer essentially composed of methanol from the above two separated layers is withdrawn from the distillation system; and(5) methyl acrylate or methyl methacrylate, or else, methyl acrylate or methyl methacrylate and water, are recovered from the bottom of the column.
Type:
Grant
Filed:
August 30, 1993
Date of Patent:
July 25, 1995
Assignees:
Mitsubishi Rayon Co., Ltd., Osaka Organic Chemical Ind. Co., Ltd.
Abstract: Excess alcohol, e.g. methanol contained in a C.sub.4 -C.sub.6 hydrocarbon stream is removed in process using less water and energy than a conventional water wash by subjecting the stream to a first single stage water wash with 2 to 10 wt % water based on the hydrocarbon where most of the alcohol is removed and then washing the raffinate having reduced methanol therefrom subjected to multistage water wash to remove the remainder of the alcohol.
Abstract: 2-Butanone is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanone can be readily separated from isopropanol by azeotropic distillation. Effective agents are 3-methyl pentane, methyl t-amyl ether and acetonitrile.
Abstract: 3-Methyl-2-butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 2-pentanol by extractive distillation. Effective agents are acetamide or 2,2,2-trichloroethanol.
Abstract: 1-Butanol is difficult to semarate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be readily separated from 2-pentanol by azeotropic distillation. Effective agents are 1-octene, hexane and methyl cyclohexane.
Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are acetonitrile and methylene chloride.
Abstract: 3-Methyl-2-butanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 1-butanol by azeotropic distillation. Effective agents are methyl acetoacetate and dioxane.
Abstract: 3-Methyl-2-butanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 1-butanol by extractive distillation. Effective agents are ethyl n-valerate, dimethylacetamide and dimethylsulfoxide.
Abstract: 3-Methyl-2-butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 2-pentanol by azeotropic distillation. Effective agents are pentane, 2,2-dimethyl butane and dioxane.
Abstract: Carbonaceous preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are activated or regenerated by treatment with an aqueous cobalt salt solution in the presence of a light alcohol having from about 4 to 7 carbon atoms and syn gas prior to exposure to or processing with any other organic stream at a temperature of about 120.degree. C. to 190.degree. C. and a pressure of about 13 MPa to 32 MPa for about 2 to 50 hours.
Abstract: 1-Butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be readily separated from 2-pentanol by extractive distillation. Effective agents are ethyl benzene, d-limonene and terpinolene.
Abstract: A method for recovering 1,4-butanediol from a hydrolysate obtained by hydrolyzing diacetoxybutane, by (1) supplying the hydrolysate to a first distillation column, distilling off substantially all the amounts of water and acetic acid as the top stream from the first distillation column, and supplying a bottom liquid to a second distillation column, (2) distilling off diacetoxybutane and hydroxyacetoxybutane as the top or upper side stream from of the second distillation column, and circulating the distillates to a hydrolysis zone, while withdrawing crude 1,4-butanediol as a lower side stream in vapor phase from the second distillation column, (3) supplying the crude 1,4-butanediol and hydrogen gas to a hydrogenation reaction zone packed with a hydrogenation catalyst, and (4) supplying the hydrogenation reaction product to a third distillation column, distilling off low boiling point components and withdrawing 1,4-butanediol as the bottom or side stream from the third distillation column.
Abstract: This invention provides an environmentally acceptable method for recovery of phenolic and brominated phenolic compounds, alcohol solvent, and bromide values from the a reaction medium liquid mixture formed in the production of a tetrabromobisphenol-A predominant product. The process comprises (a) separating the tetrabromobisphenol-A predominant product and alkyl bromide from the reaction medium thereby forming a liquid mixture containing alcohol, phenolic and brominated phenolic compounds, HBr, and water; (b) treating the liquid mixture with a sufficient amount of alkaline or alkaline earth metal hydroxide so as to form a treated aqueous mixture having a pH in the range of from about 9.5 to about 14.0, and containing MBr.sub.
Type:
Grant
Filed:
May 19, 1994
Date of Patent:
March 7, 1995
Assignee:
Albemarle Corporation
Inventors:
Robert E. Williams, William J. Cranston, III
Abstract: An apparatus and method for treating chemical production plant process condensate such that a contaminant-rich stream and a relatively pure aqueous stream is separately recoverable from the condensate, wherein the contaminants are substantially removed from the condensate by steam stripping and subsequent rectification in a relatively low pressure stripping/rectification tower. The tower overhead is then condensed with a portion of the condensed overhead being returned to the top of the rectification section of the tower as reflux and the balance being withdrawn as a concentrated stream for reuse in the plant. In a second embodiment, separate stripping and rectification towers operate in series whereby the overhead of the stripping tower is delivered to the lower section of the rectification tower and the rectification bottoms are returned to the top of the stripping tower.
Abstract: A first alkanol having 1 to 3 C atoms or a mixture of this first alkanol with water or water itself can be separated off from oxygen-containing organic compounds having 3 to 7 C atoms from the group comprising second alkanols and dialkyl carbonates, which always have at least 2 C atoms more than the first alkanol, by permeation on membranes if a membrane obtained by plasma polymerization is employed.
Type:
Grant
Filed:
October 6, 1993
Date of Patent:
November 1, 1994
Assignee:
Bayer Aktiengesellschaft
Inventors:
Andreas Nickel, Wolfgang Arlt, Ingo Janisch, Paul Wagner, Alexander Klausener
Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by extractive distillation. Effective agents are methyl caproate, adiponitrile and cyclopentanone.
Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by extractive distillation. Effective agents are isobutyl acetate, isobornyl methyl acetate and ethyl butyrate.
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
Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are methyl caproate, cyclopentane and isobutyl acetate.
Abstract: A methanol refining column and method using an intermediate reboiler. Use of the intermediate reboiler reduces methanol production energy requirements. A side stream at or near a fusel oil takeoff point is heated in an intermediate reboiler by a low temperature heating medium (relative to a bottoms reboiler) and returned to the column at or near the fusel oil take-off tray. The take-off tray is operated at 85.degree.-110.degree. C., and 70-90 percent of the reboiler duty is supplied through the intermediate reboiler. The remaining heat load is supplied by a bottoms steam reboiler.
Type:
Grant
Filed:
June 18, 1993
Date of Patent:
September 13, 1994
Assignee:
The M. W. Kellogg Company
Inventors:
Edward J. Cialkowski, Thomas P. Ognisty
Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by azeotropic distillation. Effective agents are ethyl acetoacetate, nitroethane and 3-pentanone.
Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are methyl ethyl ketone, cyclopentane and 2-pyrrolidinone.
Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by azeotropic distillation. Effective agents are t-butyl methyl ether, 1,4-dioxane and ethyl formate.
Abstract: 1-Pentanol is difficult to separate from cyclopentanol by conventional distillation or rectification because of the closeness of their boiling points. 1-Pentanol can be readily separated from cyclopentanol by extractive distillation. Effective agents are ethylene glycol and sulfolane.
Abstract: A method for separating a water soluble noble metal catalyst from a crude reaction product of a noble metal-catalyzed process for preparing octadienol from butadiene in aqueous solution, in an aqueous emulsion or as an aqueous suspension, the crude reaction product including an aqueous phase containing a water soluble Group VIII noble metal-ligand complex catalyst, and an organic phase containing unreacted butadiene feed and an organic octadienol reaction product, which comprises: (a) contacting the crude reaction product with a hydrophobic membrane capable of allowing a substantial portion of the unreacted butadiene feed and organic octadienol reaction product to pass therethrough while retaining a substantial portion of the water soluble Group VIII noble metal-ligand complex catalyst; (b) removing unreacted butadiene feed and the organic octadienol reaction product which passes through the hydrophobic membrane as permeate; and (c) retaining the water soluble Group VIII noble metal-ligand complex catalyst as
Abstract: Disclosed is a purification process for removing lipophilic impurities coined in an aqueous crude ethanol solution, in particular, for efficiently removing impurities consisting of C.sub.3 -C.sub.4 alcohols. The process involves (a) a first extraction step wherein the aqueous crude ethanol solution is extracted with an extractant for removing the lipophilic impurities, except for the C.sub.3 -C.sub.4 alcohols, contained in the aqueous crude ethanol solution by subjecting the aqueous crude ethanol solution to extraction with the extractant in a pressurized state containing carbon dioxide in a liquidized state or carbon dioxide gas in a supercritical state; (b) a concentration-distillation step wherein a raffinate obtained in the first extraction step is fed to a distilling column to thereby obtain a highly concentrated aqueous ethanol solution from a top of the distilling column and withdraw fraction containing C.sub.3 -C.sub.
Type:
Grant
Filed:
February 3, 1993
Date of Patent:
February 8, 1994
Assignee:
Basic Industries Bureau of Ministry of International Trade and Industry
Abstract: A stream of raw phenol, coming from the acidic cracking of cumene hydroperoxide, is purified by a process of extractive distillation carried out in the presence of acetophenone.
Type:
Grant
Filed:
May 24, 1991
Date of Patent:
November 16, 1993
Assignee:
Enimont Anic S.r.l.
Inventors:
Loreno Lorenzoni, Salvatore Simula, Giuseppe Messina, Vittorio Bruzzi
Abstract: The separation of ethyl tertiobutyl ether from mixtures with ethanol is based on heteroazeotropic distillation with water as the entrainer using two distillation columns, coupled with an overhead decanter. Purified ethanol is collected from the bottom of the first column and purified ETBE from the bottom of the second column. The separation method may be incorporated into an ETBE production unit in which isobutene (contained in a C.sub.4 -cut from steam cracking, catalytic cracking, or dehydrogenation of isobutane) is etherified by ethanol. Ethanol separated from the ETBE is then recycled to the etherification zone.
Type:
Grant
Filed:
March 9, 1992
Date of Patent:
October 5, 1993
Assignee:
Institut Francais du Petrole
Inventors:
Annick Pucci, Paul Mikitenko, Massimo Zuliani
Abstract: Motor-fuel tertiary butyl alcohol contaminated with residual amounts of tertiary butyl hydroperoxide, ditertiary butyl peroxide and allyl tertiary butyl peroxide (which is prepared, for example, by reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and a motor fuel grade tertiary butyl alcohol reaction product) can be effectively catalytically treated under mild conversion conditions including a temperature of about 160.degree. to 200.degree. C. with a catalyst consisting essentially of vitrified silica to substantially completely decompose the peroxide contaminants to thereby provide a treated tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides.
Type:
Grant
Filed:
June 12, 1992
Date of Patent:
September 7, 1993
Assignee:
Texaco Chemical Company
Inventors:
John R. Sanderson, Yu-Hwa E. Sheu, Michael W. Peters
Abstract: The present invention is a process for the recovery of normal alcohols, especially C.sub.1 -C.sub.20 n-alcohols, preferably n-C.sub.4 -C.sub.14 alcohols, most preferably n-C.sub.6 -C.sub.11 alcohols from n-paraffins by means of pervaporation through a membrane. The alcohols/paraffin feed mixture may be that produced in the Fischer-Tropsch synthesis process wherein mixtures of CO and H.sub.2 are reacted to produce paraffin waxes and a minor but still valuable amount of alcohols.
Type:
Grant
Filed:
November 2, 1992
Date of Patent:
July 27, 1993
Assignee:
Exxon Research and Engineering Company
Inventors:
Charles P. Darnell, Russell J. Koveal, Tan J. Chen, W. S. Winston Ho
Abstract: A process for purifying 2,3-dichloro-1-propanol is disclosed, which comprises introducing a chlorination reaction mixture obtained by chlorination of allyl alcohol in a hydrochloric acid aqueous solution in a reactor, to a degassing tower, where hydrogen chloride is released, returning the hydrogen chloride to the chlorination reactor, cooling the residual liquid to separate into an aqueous layer and an oily layer, and returning the aqueous layer to the chlorination reactor while recovering 2,3-dichloro-1-propanol from the oily layer, wherein said oily layer is introduced to a first distillation tower, where hydrogen chloride, part of the produced 2,3-dichloro-1-propanol, and other low-boiling components are recovered as a distillate, cooling the distillate to separate it into an aqueous layer and an oily layer, returning the aqueous layer of the distillate to the chlorination reactor, and recovering 2,3-dichloro-1-propanol from the oily layer of the distillate and a high-boiling fraction of the first distill
Type:
Grant
Filed:
November 25, 1992
Date of Patent:
July 13, 1993
Assignee:
Showa Denko K.K.
Inventors:
Toshio Mori, Hiromitu Nojima, Koji Kudo, Tatsuharu Arai
Abstract: A method and apparatus for conducting a catalytic distillation process is provided which allows for maintaining a liquid level in selected portions of the catalyst bed. Three particular processes disclosed are the production of methyl tertiary butyl ether, tertiary butyl alcohol and cumene.
Abstract: The present invention relates to stabilizing unmilled or partially milled brown rice by contact thereof with ethanol vapors. The present invention also encompasses products of said stabilizing including, stabilized unmilled or partially milled brown rice, and partially stabilized flour produced by grinding of said stabilized unmilled or partially milled brown rice.
Type:
Grant
Filed:
May 2, 1991
Date of Patent:
May 11, 1993
Assignee:
The United States of America as represented by the Secretary of Agriculture
Inventors:
Elaine T. Champagne, Robert J. Hron, Sr., George Abraham
Abstract: Tetrachloroethylene cannot be completely separated from methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, 1-pentanol, 2-pentanol, 3-methyl-1-butanol or t-amyl alcohol by conventional distillation or rectification because of the minimum boiling azeotropes. Tetrachloroethylene can be readily separated from these alcohols by extractive distillation. A typical effective agent is dimethylsulfoxide.
Abstract: A method for drying erythritol crystals having a moisture content of from 1 to 10% by weight to reduce to the moisture content of 0.15% by weight or below, which comprises drying under fluidized state wherein a temperature of a gas to be used in the fluidized drying is controlled within a range of from 10.degree. to 60.degree. C. at least until the moisture content of said crystals is reduced to 0.5% by weight or below.The moisture content of erythritol crystals (moisture content: 1 to 10% by weight) can be highly efficiently reduced to 0.15% by weight or below in a stable form without deteriorating the crystalline properties and form by fluidized drying said erythritol crystals with the use of a gas flow of a relatively low specific temperature.
Abstract: 1,1,1-Trichloroethane cannot be completely separated from methanol, ethanol, n-propanol, isopropanol, 2-butanol or t-butanol by conventional distillation or rectification because of the minimum boiling azeotropes. 1,1,1-Trichloroethane can be readily separated from these alcohols by extractive distillation. A typical effective agent is dimethylsulfoxide.
Abstract: Methanol contaminated with residual amounts of peroxide contaminants such as tertiary butyl hydroperoxide, ditertiary butyl peroxide, allyl tertiary butyl peroxide, etc., can be effectively catalytically treated with a catalyst consisting essentially of titania-supported transition metals to substantially completely decompose the peroxide contaminants to thereby provide a treated methanol product substantially free from contaminating quantities of such peroxides.
Abstract: Tetracholorethylene cannot be completely separated from n-butanol, isobutanol or 2-butanol by conventional distillation or rectification because of minimum boiling azeotropes. Tetrachloroethylene can be readily separated from n-butanol, isobutanol or 2-butanol by extractive distillatiion. Typical effective agents are: for n-butanol, dipropylene glycol methyl ether; for isobutanol, dimethylsulfoxide and isobutyl butyrate; for 2-butanol, ethylene glycol methyl ether and isobornyl acetate.
Abstract: For the separation of tert. butyl ethyl ether from mixtures with ethanol, there are provided two distillation stages, the first being carried out at a pressure p.sub.1 equal to or higher than 1 bar, the second at a pressure p.sub.2 below p.sub.1 by a value .DELTA.p or 0.5 to 12 bars, p.sub.2 then being 0.5 to 10 bars. The second column distillate is partly supplied as reflux to the head of the second column and is in part recycled to the head of the first column. The purified TBEE is collected at the bottom of the first column and the purified ethanol at the bottom of the second column.This separation process can be integrated into a TBEE production unit comprising etherification by ethanol of the isobutylene contained in a C.sub.4 fraction from a catalytic cracking or steam cracking stage. The ethanol separated from the TBEE is then recycled to the etherification zone.
Type:
Grant
Filed:
April 9, 1991
Date of Patent:
October 27, 1992
Assignee:
Institut Francais du Petrole
Inventors:
Annick Pucci, Paul Mikitenko, Massimo Zuliani
Abstract: Methylene chloride cannot be completely separated from methanol or ethanol by conventional distillation or rectification because of the mimimum boiling azeotrope. Methyelne chloride can be readily separated from methanol or ethanol by azeotropic or extractive distillation. Typical effective agents are: for methanol by azeotropic distillation, isopropanol or t-butanol; by extractive distillation, 1-nitropropane or n-butanol; for ethanol by extractive distillation, isobutanol or n-propyl acetate.
Abstract: According to the process of this invention, alcohols are recovered from aqueous acid solution by permeation of the alcohol through an organic-acid modified polymer membrane. An improved process for the manufacture of alcohols by acid absorption of olefins is also disclosed, the improvement residing in the use of an organic-acid modified polymer membrane to selectively permeate alcohols from the concentrated aqueous strong acid solution thereof co-produced in their synthesis from olefins.
Type:
Grant
Filed:
March 13, 1989
Date of Patent:
September 8, 1992
Assignee:
Exxon Chemicals Patents Inc.
Inventors:
Abraham D. Cohen, William D. Diana, James J. Baiel
Abstract: Chloroform cannot be completely separated from methanol, ethanol or isopropanol by conventional distillation or rectification because of the minimum boiling azeotrope between chloroform and the alcohols. Chloroform can be readily separated from methanol, ethanol or isopropanol by extractive distillation. Typical effective agents are: for methanol, isopropanol or 4-methyl-2-pentanone; for ethanol, n-butanol or isobutyl acetate; for isopropanol, butyl acetate or ethylene glycol ethyl ether.
Abstract: Trichloroethylene cannot be completely separated from n-butanol, isobutanol, 2-butanol or t-butanol by conventional distillation or rectification because of the minimum boiling azeotropes. Trichloroethylene can be readily separated from n-butanol, isobutanol, 2-butanol or t-butanol by extractive distillation. Typical effective agents are: for n-butanol, dimethylsulfoxide; for isobutanol, n-octanol; for 2-butanol, 2-methyl-1-pentanol and for t-butanol, n-butyl acetate.
Abstract: A method of producing ethanol from a fermentation source for direct blending into gasoline to form gasohol is provided by extracting ethanol from the fermentation broth with a non-toxic solvent compatible with gasoline. The invention includes extraction outside of the fermentor and the recycling of the extracted broth back to the fermentor. An extracting column is used for the extraction and recycling and the extract can be dried before blending it with the gasoline. The preferred solvent is an alkylate.
Type:
Grant
Filed:
June 13, 1990
Date of Patent:
May 5, 1992
Assignee:
The Board of Trustees of the University of Little Rock Arkansas
Inventors:
Jim L. Turpin, Robert B. Eldridge, Sharon Booth-McGee
Abstract: The invention relates to a process for concentrating TBHP while avoiding flammability and explosion hazards by distilling a mixture of TBHP and TBA under reduced pressure of up to 300 mm Hg and separating a liquid TBHP concentrate containing at least 65 wt. % TBHP.
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
Abstract: A method for recovering hydrobromic acid and methanol from a filtrate obtained by brominating bisphenol A in a methanol solvent and filtering off the resulting brominated bisphenol A, which comprises adding water to the filtrate, followed by distillation for purification.