Methanol Patents (Class 203/66)
  • Patent number: 11220646
    Abstract: The coal-derived solid hydrocarbon particles are discrete particles of coal-derived carbonaceous matter having a particle size less than about 10 ?m that are substantially free of inherent or entrained mineral matter. The particles of have an average particle size in the range from 1 ?m to 8 ?m. The particles of coal-derived carbonaceous matter are milled to a size approximately the same as a size of coal-derived mineral matter inherent in the coal source to release inherent coal-derived mineral matter particles such that the particles of carbonaceous matter and the particles of mineral matter are discrete and separable solid particles. Following separation, less than 1.5 wt. % discrete coal-derived mineral matter particles are associated with the discrete particles of coal-derived carbonaceous matter. Particles of coal-derived solid hydrocarbon matter are blended with a gaseous or liquid hydrocarbon fuel to form a two-phase hydrocarbon fuel feedstock.
    Type: Grant
    Filed: April 3, 2020
    Date of Patent: January 11, 2022
    Assignee: OMNIS MINERAL TECHOLOGIES, LLC
    Inventors: James S. Swensen, Simon K. Hodson
  • Patent number: 8900417
    Abstract: This invention provides a method for purifying HFO-1234yf by removing HF from a mixture of HFO-1234yf and HF under simple and economically advantageous conditions.
    Type: Grant
    Filed: July 21, 2011
    Date of Patent: December 2, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Takehiro Chaki, Kazuhiro Takahashi
  • Patent number: 7846304
    Abstract: The present invention provides a process for purifying 2-chloro-5-chloromethyl-1,3-thiazole represented by the formula (I): characterized in that a crude 2-chloro-5-chloromethyl-1,3-thiazole represented by the formula (I) is treated with a lower alcohol before the distillation, and then is distilled. The present purification process is a new one for purifying 2-chloro-5-chloromethyl-1,3-thiazole, suitable for industrial practice.
    Type: Grant
    Filed: March 30, 2009
    Date of Patent: December 7, 2010
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Toshikazu Oga, Toru Kofukuda
  • Patent number: 7718040
    Abstract: Product propylene oxide in a reaction mixture resulting from the reaction of propylene, oxygen and hydrogen or from the reaction of propylene and hydrogen peroxide is separated from propylene and/or propane by extractive distillation using methanol and/or water extractive distillation solvent.
    Type: Grant
    Filed: March 23, 2007
    Date of Patent: May 18, 2010
    Assignee: Lyondell Chemical Technology, L.P.
    Inventor: Te Chang
  • Publication number: 20080230369
    Abstract: Product propylene oxide in a reaction mixture resulting from the reaction of propylene, oxygen and hydrogen or from the reaction of propylene and hydrogen peroxide is separated from propylene and/or propane by extractive distillation using methanol and/or water extractive distillation solvent.
    Type: Application
    Filed: March 23, 2007
    Publication date: September 25, 2008
    Inventor: Te Chang
  • Patent number: 7091252
    Abstract: Bubble columns fractionate with vapor-liquid mass transfer efficiencies approaching that of distillation towers when vapor velocities in excess of 50% of jet flood are used. If the vapor velocities are pushed above about 70% of jet flood then the distillation performance of a given column packing becomes similar for both liquid continuous operation (bubble column mode) and vapor continuous operation (ordinary distillation tower mode).
    Type: Grant
    Filed: January 13, 2005
    Date of Patent: August 15, 2006
    Assignee: Catalytic Distillation Technologies
    Inventors: Lawrence A. Smith, Jr., Mitchell E. Loescher
  • Patent number: 6679975
    Abstract: The present invention aims to isolate the azeotropes formed in a distillation column (B1) by methanol, propane and butane. The azeotropes are then liquefied in heat exchanger (E2) and mixed in contactor (M1) with water in order to dissolve the methanol in water. The mixture is then fed into a decantation tank (D2) to separate the aqueous phase from the liquid hydrocarbon phase. Finally, an aqueous phase containing methanol is discharged and the methanol-depleted hydrocarbon phase is recycled to distillation column (B1) as reflux.
    Type: Grant
    Filed: January 7, 2002
    Date of Patent: January 20, 2004
    Assignee: Institut Francais du Petrole
    Inventors: Géraldine Laborie, Fabrice Lecomte, Annick Pucci
  • Patent number: 6559248
    Abstract: Disclosed is a method of purifying olefin containing oxygenate contaminants. The method incorporates the use of extractive distillation. Under the appropriate conditions, olefins containing very low levels of oxygenate contaminants can be recovered.
    Type: Grant
    Filed: August 31, 2001
    Date of Patent: May 6, 2003
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Dan E. Hendriksen, Minquan Cheng, Keith H. Kuechler, David R. Lumgair, Michael P. Nicoletti, Richard Shutt
  • Patent number: 6531108
    Abstract: This invention provides a highly pure and highly concentrated free hydroxylamine aqueous solution substantially not containing any salt or organic substance. This invention is a process for obtaining a free hydroxylamine aqueous solution, comprising the steps of letting an aqueous solution or slurry containing hydroxylammonium sulfate and an alkali react with each other, to obtain an aqueous solution or slurry containing free hydroxylamine and dissolved or partially precipitated sulfates; mixing the obtained reaction solution and a lower alcohol, to precipitate solid sulfates; separating a solution containing the lower alcohol and some of water by distillation from the aqueous solution remaining after separating and removing the solid sulfates; and obtaining a free hydroxylamine aqueous solution from the remaining solution by distillation.
    Type: Grant
    Filed: July 19, 2000
    Date of Patent: March 11, 2003
    Assignee: Toray Fine Chemicals Co., Ltd.
    Inventors: Kumiko Bansho, Yoshio Noguchi
  • Patent number: 6359155
    Abstract: An industrial advantage process for producing high-purity 3-hydroxytetrahydrofuran easily and simply, which comprises reducing a 4-halo-3-hydroxybutyric acid ester (1) with a boron hydride compound and/or an aluminum hydride compound as a reducing agent in an organic solvent immiscible with water; treating the reaction mixture with an acid and water to thereby effect conversion to the corresponding 4-halo-1,3-butanediol and at the same time giving an aqueous solution containing said compound; carrying out the cyclization reaction of the 4-halo-1,3-butanediol in said aqueous solution; extracting the resulting 3-hydroxytetrahydrofuran from the 3-hydroxytetrahydrofuran-containing aqueous solution using an organic solvent immiscible with water; and isolating the 3-hydroxytetrahydrofuran by concentration and/or distillation of the solution obtained.
    Type: Grant
    Filed: February 15, 2001
    Date of Patent: March 19, 2002
    Assignee: Kaneka Corporation
    Inventors: Koichi Kinoshita, Tadashi Moroshima, Yoshifumi Yanagida, Nobuo Nagashima, Yasuhiro Saka, Tatsuya Honda, Yoshihide Fuse, Yasuyoshi Ueda
  • Patent number: 6197163
    Abstract: The impurity content, e.g. propionitrile, in a fraction containing C5 or C6 tertiary olefins obtained by cracking hydrocarbons is reduced by distilling with an alkanol and removing the impurity as a higher boiling point fraction.
    Type: Grant
    Filed: November 29, 1993
    Date of Patent: March 6, 2001
    Assignee: Catalytic Distillation Technologies
    Inventor: Claus-Peter Thomas Hälsig
  • Patent number: 6030524
    Abstract: In an atmospheric pipestill stripping process where steam is utilized as the stripping gas to strip bottoms and side stream products, the improvement comprising utilizing methanol or a methanol and steam mixture as said stripping gas. In a refinery atmospheric pipestill stripping process utilizing a stripping gas, said process comprising utilizing a gas selected from the group consisting of methanol and a mixture of methanol and steam as said stripping gas.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: February 29, 2000
    Assignee: Exxon Research and Engineering Co
    Inventors: David W. Savage, Guido Sartori
  • Patent number: 5882485
    Abstract: A process for the separation of dimethyl ether and chloromethane in mixturesA process for the separation of dimethyl ether and chloromethane in mixtures by two distillation steps. In the first step, the mixture is subjected to an extractive distillation with water, aqueous salt solutions or organic liquids as extractant, the top product being chloromethane. In the second step, the dimethyl ether is separated from the extractant.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: March 16, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Roth, Erhard Leistner, Hans Haverkamp, Wolfgang Wendel, Michael Kleiber
  • Patent number: 5830325
    Abstract: The disclosure relates to separating 1,1,1-trifluoroethane (HFC-143a from fluorocarbon impurities by using extractive distillation with an extractive agent comprising an alcohol. Examples of suitable extractive agents comprise at least one member from the group of methanol, butanol, ethanol, propanol, their isomers and cyclic compounds thereof, among others.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: November 3, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Barry Asher Mahler, Ralph Newton Miller
  • Patent number: 5698080
    Abstract: Phellandrene is difficult to separate from limonene because of the proximity of their boiling points. They are readily separated by azeotropic distillation. Effective agents are ethanol, dioxolane and acetonitrile.
    Type: Grant
    Filed: November 22, 1996
    Date of Patent: December 16, 1997
    Inventor: Lloyd Berg
  • Patent number: 5470442
    Abstract: The disclosure relates to separating 1,1,2,2 tetrafluoroethane (HFC-134) and 1,1,1,2 tetrafluoroethane (HFC-134a) from each other and/or from fluorocarbon impurities by using extractive distillation with an extractive agent comprising an alcohol. Examples of suitable extractive agents comprise at least one member from the group of methanol, butanol, ethanol, propanol, their isomers and cyclic compounds thereof, among others.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: November 28, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Barry A. Mahler, Ralph N. Miller
  • Patent number: 5466345
    Abstract: o-Xylene cannot be separated from p-xylene and m-xylene by conventional distillation or rectification because of the proximity of their boiling points. o-Xylene can be readily separated from mixtures of p-xylene and m-xylene by azeotropic distillation. Effective agents are 3-methyl-1-butanol, methyl propionate and 3-pentanone.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: November 14, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5405504
    Abstract: 1-Decene is impossible to separate from 2-octanone by conventional distillation or rectification because the two compounds form a minimum boiling azeotrope. 1-Decene can be readily separated from 2-octanone by azeotropic distillation. Effective agents are 1-propanol, 2-ethoxyethanol, and methanol.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: April 11, 1995
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randy W. Wytcherley
  • Patent number: 5405505
    Abstract: Benzene is difficult to separate from cyclohexane or cyclohexene by conventional distillation or rectification because of the close proximity of their boiling points. Benzene can be readily separated from cyclohexane or cyclohexene by using azeotropic distillation. Effective agents are: for benzene from cyclohexane, dimethoxymethane; for benzene from cyclohexene, methanol.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: April 11, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5292993
    Abstract: The impurity content, e.g. propionitrile, in a fraction containing C.sub.5 or C.sub.6 tertiary olefins obtained by cracking hydrocarbons is reduced by distilling with an alkanol and removing the impurity as a higher boiling point fraction.
    Type: Grant
    Filed: August 5, 1992
    Date of Patent: March 8, 1994
    Assignee: The British Petroleum Company p.l.c.
    Inventor: Claus-Peter T. Halsig
  • Patent number: 5227521
    Abstract: This invention is a process for the production of trialkyl acetic acids, particularly of pivalic acid, from branched olefins, particularly isobutene, and carbon monoxide using catalytic amounts of a Lewis acid such as boron trifluoride.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: July 13, 1993
    Assignee: Catalytica Inc.
    Inventors: Michael A. Richard, William A. Sanderson
  • Patent number: 5145989
    Abstract: Black acid or the sulfuric acid residue obtained in the manufacture of ethyl acrylate by reaction of ethylene and acrylic acid in the presence of sulfuric acid is heated and distilled in the presence of a solvent for recovery of acrylic acid and ethyl acrylate.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: September 8, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Edward F. Dougherty, Paul James L.
  • Patent number: 4944847
    Abstract: A method of inhibiting fouling in distillation towers, overhead lines, reflux lines, and condensers operating in a process to manufacture and purify epichlorohydrin. This method resides in treating process streams entering or exiting such towers, lines and condensers, including feed streams, reflux streams, gaseous or liquid overhead streams, with an effective antifouling amount of a C.sub.3 -C.sub.9 linear or branched alkyl substituted catechol, or mixtures thereof.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: July 31, 1990
    Assignee: Nalco Chemical Company
    Inventor: Karis W. Snow
  • Patent number: 4879407
    Abstract: A process for the preparation of ethyl trifluoroacetate, in which:in a first stage, trifluoroacetic acid is brought into contact with a slight excess of ethanol in the presence of concentrated sulfuric acid and a solvent, the solvent having a boiling point higher than that of trifluoroacetic acid and specific gravity relative to water less than 1 and which solvent does not form an azeotrope with ethyl trifluoroacetate, and then carrying out a phase separation and removing the sulfuric layer, followed, if required, by an additional stage in which concentrated sulfuric acid is added to complete the esterification;in a second stage, an additional quantity of sulfuric acid and trifluoroacetic acid is introduced and a phase separation is then carried out to remove the sulfuric layer; andin a third stage, the mixture obtained in the second stage is distilled to recover ethyl trifluoroacetate.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: November 7, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventor: Louis Amiet
  • Patent number: 4798674
    Abstract: Mixtures containing methanol and dimethyl carbonate or methanol and methyl t-butyl ether may be treated by pervaporation to recover product containing decreased quantity of methanol.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: January 17, 1989
    Assignee: Texaco Inc.
    Inventors: Mordechai Pasternak, Craig R. Bartels, John Reale, Jr.
  • Patent number: 4761492
    Abstract: An extractive distillation process for recovering trimethoxysilane from a trimethoxysilane-methanol mixture is provided using as the extractive solvent tetramethoxysilane.
    Type: Grant
    Filed: September 28, 1987
    Date of Patent: August 2, 1988
    Assignee: Union Carbide Corporation
    Inventors: Thomas E. Childress, George M. Omietanski, Frank D. Mendicino
  • Patent number: 4760165
    Abstract: A method of recovering useful components at least containing dimethyl terephthalate from high-boiling byproducts occurring in the production of dimethyl terephthalate, which comprises oxidizing p-xylene and/or methyl p-toluate with a molecular oxygen-containing gas in the presence of a heavy metal oxidation catalyst, subjecting the resulting oxidation product to esterification with methanol, separating dimethyl terephthalate and esters having lower boiling points than dimethyl terephthalate from the esterification reaction product by distillation, and thereafter treating the distillation residue containing byproducts having higher boiling points than dimethyl terephthalate with methanol to recover at least dimethyl terephthalate from the treated product; wherein the treatment of the distillation residue with methanol is carried out at a temperature of 110.degree. to 240.degree. C. under a pressure sufficient to maintain methanol in the liquid phase.
    Type: Grant
    Filed: November 10, 1986
    Date of Patent: July 26, 1988
    Assignee: Teijin Petrochemical Industries, Ltd.
    Inventors: Hideo Hasegawa, Takao Fujii
  • Patent number: 4730082
    Abstract: A process for the preparation of methyltrifluoroacetate. Trifluoroacetic acid is contacted with an excess of methanol and distilled to form a methyltrifluoroacetate/methanol azeotrope. The azeotrope is contacted with trifluoroacetic acid in the presence of a catalytic quantity of a strong acid followed by distillation to obtain methyltrifluoroacetate. The methyltrifluoroacetate can be used as a synthesis intermediate in the pharmaceutical industry.
    Type: Grant
    Filed: June 12, 1986
    Date of Patent: March 8, 1988
    Assignee: Rhone-Poulenc Specialties Chimiques
    Inventor: Louis Amiet
  • Patent number: 4714526
    Abstract: A process for extracting pure components from a multi-component system, said system comprising a mixture of at least two solids or liquids in a supercritical fluid at constant pressure, which involves making use of the cross-over pressure points of the components which comprise the system.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: December 22, 1987
    Assignee: The University of Rochester
    Inventors: Kenneth Pennisi, Eldred Chimowitz
  • Patent number: 4476036
    Abstract: Quaternary azeotropic mixtures of 1,1,2-trichloro-1,2,2-trifluoroethane, methylene chloride, methanol and cyclopentane are provided. These azeotropic mixtures are useful as solvents to remove buffing compounds residues. These mixtures are useful not only because of their high solvency characteristics but also because they exhibit essentially the constant boiling characteristics of an azeotrope which is formed between these components, thereby facilitating handling and purification of the solvent mixtures without significantly altering their compositions. [The quaternary mixtures disclosed herein exhibit certain advantageous solvency characteristics of glycol based compositions, over the known binary or ternary azeotropic systems containing 1,1,2-trichloro-1,2,2-trifluoroethane, methylene chloride, methanol and cyclopentane.
    Type: Grant
    Filed: September 12, 1983
    Date of Patent: October 9, 1984
    Assignee: Allied Corporation
    Inventors: Francis J. Figiel, Aaron Colbert
  • Patent number: 4454356
    Abstract: Methanol is reacted with branched monoolefins such as isobutylene, or mixtures of hydrocarbons such as mixed C-4's from or in a refinery, in the presence of methanesulfonic acid. A column (10) operation is described wherein methanesulfonic acid (11) and methanol (12) are fed in countercurrent fashion to hydrocarbons (13). Crude product ether is removed as a liquid sidestream (25) above the feed of methanesulfonic acid (11), while hydrocarbons depleted of the reactive branched monoolefins (24) are removed overhead. The methanesulfonic acid suppresses the vapor pressure of methanol relative to product ether.
    Type: Grant
    Filed: October 14, 1982
    Date of Patent: June 12, 1984
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Andiappan K. S. Murthy
  • Patent number: 4414063
    Abstract: Removal of acrylonitrile from latex by azeotropic distillation with methanol.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: November 8, 1983
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Robert A. Smiley
  • Patent number: 4365080
    Abstract: This invention provides an improved process for the separation and recovery of byproducts associated with the isolation of C.sub.4 -C.sub.6 dicarboxylic acids contained in a waste byproduct stream derived from an adipic acid manufacturing operation involving nitric acid oxidation of a cyclohexanone/cyclohexanol feedstream.The main byproducts which are recovered are high purity dimethyl succinate, dimethyl glutarate and dimethyl adipate.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: December 21, 1982
    Assignee: El Paso Products Company
    Inventor: Norbert F. Cywinski
  • Patent number: 4365081
    Abstract: In a process for producing a 2-hydroxyalkyl acrylate or methacrylate which comprises esterifying acrylic or methacrylic acid with an alkylene oxide having 2 to 4 carbon atoms in the presence of an esterification catalyst and distilling the resulting reaction mixture in a distillation column, the improvement wherein the vapor of the ester monomer from the distillation column, while being maintained in the superheated state, is introduced into a condenser of the gas-liquid direct contact type whose inner wall corresponding to its gas inlet portion is kept at a temperature below the boiling point of the ester at the operating pressure, to contact it directly with a concurrently flowing spray liquid of the ester-precooled to a temperature below the boiling point of the ester at the operating pressure, whereby said vapor is condensed to a liquid at said temperature below the boiling point of the ester at the operating pressure.
    Type: Grant
    Filed: May 15, 1981
    Date of Patent: December 21, 1982
    Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.
    Inventors: Noboru Shimizu, Hiroshi Yoshida, Hiromiki Daigo, Shiyouichi Matumoto, Hiroyoshi Uchino
  • Patent number: 4319980
    Abstract: A process is described for obtaining a refined, carbonaceous product from essentially raw coal by treating the coal with an amine solution to dissolve a portion of the coal, leaving undissolved coal and waste material such as ash. The dissolved coal is separated from the undissolved components and the amine removed to leave the refined carbonaceous extract of the invention. The undissolved coal and waste are separated and amine removed from the undissolved coal to produce a residue. Amine is advantageously recovered for further use. Prior to treatment with amine the coal may be subjected to pre-treatment such as crushing, drying or digestion in alkali metal carbonate solution. Residual amine is advantageously removed from the refined product and residue by stripping with alcohol.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: March 16, 1982
    Inventor: Rodman Jenkins
  • Patent number: 4311851
    Abstract: The invention includes a process wherein an olefin is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, and the catalyst is recovered from the desired reaction product and the reaction by-products and is recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed to form a reaction mass containing the BF.sub.3, the alcohol, and carboxylic acid esters in a 2:1:1 molar ratio. In the first step, the one mole of free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. An azeotrope of the product carboxylic acid ester and the alcohol and residual alcohol are removed by the distillation, leaving a residue containing a 1:2 BF.sub.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: January 19, 1982
    Assignee: Chem Systems Inc.
    Inventors: John A. Jung, Jimmy Peress
  • Patent number: 4299999
    Abstract: Process for producing and isolating methyl-tert-butyl ether (MTBE) comprising etherifying isobutene, contained in a C.sub.4 hydrocarbons mixture, with methanol in the presence of a recycle stream of C.sub.5 and/or C.sub.6 hydrocarbons, separating from the obtained reaction product, by fractionation, at least the major part of the unconverted C.sub.4 hydrocarbons, and discharging them, and fractionating the remaining product in two fractions, one of which contains an azeotrope of methanol with the C.sub.5 and/or C.sub.6 hydrocarbons and is recycled, the other fraction containing the purified MTBE.
    Type: Grant
    Filed: May 9, 1980
    Date of Patent: November 10, 1981
    Assignee: Institut Francais du petrole
    Inventors: Paul Mikitenko, Lionel Asselineau
  • Patent number: 4271315
    Abstract: This invention provides a process for improving the recovery of byproducts associated with the isolation of C.sub.4 -C.sub.6 dicarboxylic acids contained in a waste byproduct stream, derived from an adipic acid manufacturing operation wherein there is involved nitric acid oxidation of a cyclohexanone/cyclohexanol feedstream.The main byproducts which are isolated are high purity dimethyl succinate, dimethyl glutarate and dimethyl adipate. Monomethyl esters of these dicarboxylic acids are recovered and recycled in the process.
    Type: Grant
    Filed: November 15, 1979
    Date of Patent: June 2, 1981
    Assignee: El Paso Products Company
    Inventor: Norbert F. Cywinski
  • Patent number: 4262138
    Abstract: In a process wherein ethylene or propylene is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, the invention concerns a technique wherein the catalyst is recovered from the reaction product and recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed, to form a reaction mass containing the BF.sub.3, the alcohol, and the carboxylic acid ester in a 2:1:1 molar ratio. In the first step, the one mole of the free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the three aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. A carboxylic acid ester/alcohol azeotrope and residual alcohol are removed by the distillation, to leave a residue containing a 1:2 BF.sub.3 /alcohol complex. This complex is combined with an additional mole of BF.sub.
    Type: Grant
    Filed: April 9, 1979
    Date of Patent: April 14, 1981
    Assignee: Chem Systems Inc.
    Inventor: Abraham P. Gelbein
  • Patent number: 4260827
    Abstract: The invention is directed to a process for the purification of aqueous solutions of low molecular weight polyhydroxyl compounds containing calcium or lead compounds or mixtures thereof. Methanol and a precipitant for calcium and/or lead ions in a quantity equivalent to the ions to be removed are added to the solutions. The deposits thus formed are removed and the residual solutions are treated with a cation exchanger followed by distillation of the low-boiling fractions. The distillation sump which essentially contains the low molecular weight polyhydroxyl compounds is then treated with an anion exchanger.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: April 7, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Klinkmann, Raimund Wambach
  • Patent number: 4256913
    Abstract: Propylene and ethylene may be carbonylated to form carboxylic acid esters or carboxylic acids in the presence of a catalyst complex containing 1 mole of BF.sub.3 and 1 mole of a second complexing component. The carboxylic acid product or acid portion of the ester product has one more carbon atom than the olefin reacted. High yields of these products are obtained. In the case of the formation of the ester, the second complexing component is an alcohol, while in the case of the preparation of carboxylic acid, the second complexing component is water. Methyl isobutyrate and methyl propionate formed by the carbonylation of propylene and ethylene, respectively, in the presence of a BF.sub.3.CH.sub.3 OH catalyst may be dehydrogenated to prepare methyl methacrylate and methyl acrylate, respectively. Similarly, the isobutyric acid and propionic acid formed from propylene and ethylene, respectively, in the presence of BF.sub.3.H.sub.
    Type: Grant
    Filed: April 9, 1979
    Date of Patent: March 17, 1981
    Assignee: Chem Systems Inc.
    Inventors: John A. Jung, Jimmy Peress
  • Patent number: 4250328
    Abstract: An improved method for separating an ester formed in a reaction mixture is disclosed. The method comprises controlling the ratio of organic acid and alcohol utilized and the removal of unreacted alcohol as an alcohol-ester azeotrope.
    Type: Grant
    Filed: February 6, 1979
    Date of Patent: February 10, 1981
    Assignee: Kyowa Yuka Co., Ltd.
    Inventors: Kiyoshi Fujita, Yukiyoshi Ito, Shigeru Kamimori
  • Patent number: 4243493
    Abstract: An improved petroleum distillation process in which methanol is added to the petroleum to be distilled and methanol/hydrocarbon azeotrope is recovered boiling at about 63.degree. C. which can be used as a fuel. The methanol can be derived from natural gas or another fossil fuel source. A methanol crude oil emulsion from a long distance pipeline can be distilled by this process without preliminary treatment.
    Type: Grant
    Filed: February 3, 1978
    Date of Patent: January 6, 1981
    Assignee: Mannesmannrohren-Werke A.G.
    Inventors: Kurt Gruber, Willi Keim, Klaus Hentschel
  • Patent number: 4229263
    Abstract: Esters are treated with alkali metal borohydride to produce alcohols. Substantially constant boiling admixtures of: methanol/methyl heptafluorobutyrate, water/1,1-dihydroheptafluorobutanol, and water/methyl heptafluorobutyrate are described.
    Type: Grant
    Filed: December 21, 1978
    Date of Patent: October 21, 1980
    Assignee: Phillips Petroleum Company
    Inventor: William V. Childs
  • Patent number: 4163696
    Abstract: There is disclosed an azeotropic distillation process for separating toluene from methyl isobutyl ketone (MIBK) in a spent liquor mixture. A toluene azeotrope former, preferably methanol, is added to the liquor in an amount sufficient to form an azeotrope with all of the toluene present in the mixture. The methanol is added in an amount of at least about 2.62, typically an excess amount of about 3.4 to about 6.3 parts by weight of methanol per 1.0 part by weight of toluene. The resulting azeotrope of methanol and toluene is then separated by distillation from the MIBK. The methanol may be subsequently recovered from the toluene by extraction with water. Other toluene azeotrope formers may be utilized.
    Type: Grant
    Filed: June 7, 1978
    Date of Patent: August 7, 1979
    Assignee: Arthur G. McKee & Company
    Inventor: Wang-Mo Wong
  • Patent number: 4053369
    Abstract: In a process of extractive distillation, the combination of operating with two liquid phases in at least the uppermost trays of the column, preferably while maintaining the column operation at substantially an optimum reflux ratio, results in increased efficiencies and minimum requirements for selective solvent.
    Type: Grant
    Filed: November 24, 1976
    Date of Patent: October 11, 1977
    Assignee: Phillips Petroleum Company
    Inventor: Martin R. Cines
  • Patent number: 4039395
    Abstract: A process is provided for purification and drying of acetic acid containing water and methyl iodide and hydrogen iodide as contaminants. The process comprises distillation in a two-zone system wherein the major part of the methyl iodide and hydrogen iodide and some water are removed as overhead and bottoms, respectively, from the first zone; a stream from the middle section of the first zone is introduced into a second zone into which there is also introduced a stream of methanol; and a stream of dry purified acid is recovered from the bottom of said second zone. The process provides both for the recovery of the iodine components and the methanol added for re-use in production of additional acetic acid by the reaction of methanol and/or methyl acetate with carbon monoxide in contact with a catalyst system formed on mixing of a rhodium or iridium component and an iodine component in the presence of carbon monoxide.
    Type: Grant
    Filed: August 11, 1975
    Date of Patent: August 2, 1977
    Assignee: Monsanto Company
    Inventor: Roy T. Eby
  • Patent number: RE31010
    Abstract: In a process wherein ethylene or propylene is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, the invention concerns a technique wherein the catalyst is recovered from the reaction product and recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed, to form a reaction mass containing the BF.sub.3, the alcohol, and the carboxylic acid ester in a 2:1:1 molar ratio. In the first step, the one mole of the free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the three aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. A carboxylic acid ester/alcohol azeotrope and residual alcohol are removed by the distillation, to leave a residue containing a 1:2 BF.sub.3 /alcohol complex. This complex is combined with an additional mole of BF.sub.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: August 10, 1982
    Assignee: Chem Systems Inc.
    Inventor: Abraham P. Gelbein