Methanol Patents (Class 203/66)
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Patent number: 11220646Abstract: 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: GrantFiled: April 3, 2020Date of Patent: January 11, 2022Assignee: OMNIS MINERAL TECHOLOGIES, LLCInventors: James S. Swensen, Simon K. Hodson
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Patent number: 8900417Abstract: 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: GrantFiled: July 21, 2011Date of Patent: December 2, 2014Assignee: Daikin Industries, Ltd.Inventors: Takehiro Chaki, Kazuhiro Takahashi
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Patent number: 7846304Abstract: 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: GrantFiled: March 30, 2009Date of Patent: December 7, 2010Assignee: Toyo Boseki Kabushiki KaishaInventors: Toshikazu Oga, Toru Kofukuda
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Patent number: 7718040Abstract: 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: GrantFiled: March 23, 2007Date of Patent: May 18, 2010Assignee: Lyondell Chemical Technology, L.P.Inventor: Te Chang
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Publication number: 20080230369Abstract: 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: ApplicationFiled: March 23, 2007Publication date: September 25, 2008Inventor: Te Chang
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Patent number: 7091252Abstract: 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: GrantFiled: January 13, 2005Date of Patent: August 15, 2006Assignee: Catalytic Distillation TechnologiesInventors: Lawrence A. Smith, Jr., Mitchell E. Loescher
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Patent number: 6679975Abstract: 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: GrantFiled: January 7, 2002Date of Patent: January 20, 2004Assignee: Institut Francais du PetroleInventors: Géraldine Laborie, Fabrice Lecomte, Annick Pucci
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Patent number: 6559248Abstract: 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: GrantFiled: August 31, 2001Date of Patent: May 6, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: Dan E. Hendriksen, Minquan Cheng, Keith H. Kuechler, David R. Lumgair, Michael P. Nicoletti, Richard Shutt
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Patent number: 6531108Abstract: 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: GrantFiled: July 19, 2000Date of Patent: March 11, 2003Assignee: Toray Fine Chemicals Co., Ltd.Inventors: Kumiko Bansho, Yoshio Noguchi
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Patent number: 6359155Abstract: 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: GrantFiled: February 15, 2001Date of Patent: March 19, 2002Assignee: Kaneka CorporationInventors: Koichi Kinoshita, Tadashi Moroshima, Yoshifumi Yanagida, Nobuo Nagashima, Yasuhiro Saka, Tatsuya Honda, Yoshihide Fuse, Yasuyoshi Ueda
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Patent number: 6197163Abstract: 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: GrantFiled: November 29, 1993Date of Patent: March 6, 2001Assignee: Catalytic Distillation TechnologiesInventor: Claus-Peter Thomas Hälsig
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Patent number: 6030524Abstract: 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: GrantFiled: October 6, 1998Date of Patent: February 29, 2000Assignee: Exxon Research and Engineering CoInventors: David W. Savage, Guido Sartori
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Patent number: 5882485Abstract: 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: GrantFiled: June 23, 1997Date of Patent: March 16, 1999Assignee: Hoechst AktiengesellschaftInventors: Peter Roth, Erhard Leistner, Hans Haverkamp, Wolfgang Wendel, Michael Kleiber
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Patent number: 5830325Abstract: 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: GrantFiled: March 28, 1996Date of Patent: November 3, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Barry Asher Mahler, Ralph Newton Miller
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Patent number: 5698080Abstract: 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: GrantFiled: November 22, 1996Date of Patent: December 16, 1997Inventor: Lloyd Berg
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Patent number: 5470442Abstract: 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: GrantFiled: March 11, 1994Date of Patent: November 28, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Barry A. Mahler, Ralph N. Miller
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Patent number: 5466345Abstract: 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: GrantFiled: May 31, 1995Date of Patent: November 14, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5405505Abstract: 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: GrantFiled: January 14, 1994Date of Patent: April 11, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5405504Abstract: 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: GrantFiled: January 31, 1994Date of Patent: April 11, 1995Assignee: Lloyd BergInventors: Lloyd Berg, Randy W. Wytcherley
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Patent number: 5292993Abstract: 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: GrantFiled: August 5, 1992Date of Patent: March 8, 1994Assignee: The British Petroleum Company p.l.c.Inventor: Claus-Peter T. Halsig
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Patent number: 5227521Abstract: 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: GrantFiled: April 9, 1991Date of Patent: July 13, 1993Assignee: Catalytica Inc.Inventors: Michael A. Richard, William A. Sanderson
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Patent number: 5145989Abstract: 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: GrantFiled: July 14, 1987Date of Patent: September 8, 1992Assignee: Hoechst Celanese CorporationInventors: Edward F. Dougherty, Paul James L.
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Patent number: 4944847Abstract: 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: GrantFiled: June 12, 1989Date of Patent: July 31, 1990Assignee: Nalco Chemical CompanyInventor: Karis W. Snow
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Patent number: 4879407Abstract: 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: GrantFiled: October 16, 1987Date of Patent: November 7, 1989Assignee: Rhone-Poulenc ChimieInventor: Louis Amiet
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Patent number: 4798674Abstract: 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: GrantFiled: March 10, 1988Date of Patent: January 17, 1989Assignee: Texaco Inc.Inventors: Mordechai Pasternak, Craig R. Bartels, John Reale, Jr.
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Patent number: 4761492Abstract: An extractive distillation process for recovering trimethoxysilane from a trimethoxysilane-methanol mixture is provided using as the extractive solvent tetramethoxysilane.Type: GrantFiled: September 28, 1987Date of Patent: August 2, 1988Assignee: Union Carbide CorporationInventors: Thomas E. Childress, George M. Omietanski, Frank D. Mendicino
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Patent number: 4760165Abstract: 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: GrantFiled: November 10, 1986Date of Patent: July 26, 1988Assignee: Teijin Petrochemical Industries, Ltd.Inventors: Hideo Hasegawa, Takao Fujii
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Patent number: 4730082Abstract: 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: GrantFiled: June 12, 1986Date of Patent: March 8, 1988Assignee: Rhone-Poulenc Specialties ChimiquesInventor: Louis Amiet
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Patent number: 4714526Abstract: 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: GrantFiled: March 17, 1987Date of Patent: December 22, 1987Assignee: The University of RochesterInventors: Kenneth Pennisi, Eldred Chimowitz
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Patent number: 4476036Abstract: 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: GrantFiled: September 12, 1983Date of Patent: October 9, 1984Assignee: Allied CorporationInventors: Francis J. Figiel, Aaron Colbert
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Patent number: 4454356Abstract: 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: GrantFiled: October 14, 1982Date of Patent: June 12, 1984Assignee: Allied CorporationInventors: Divakaran Masilamani, Andiappan K. S. Murthy
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Patent number: 4414063Abstract: Removal of acrylonitrile from latex by azeotropic distillation with methanol.Type: GrantFiled: April 12, 1982Date of Patent: November 8, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: Robert A. Smiley
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Patent number: 4365080Abstract: 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: GrantFiled: May 20, 1981Date of Patent: December 21, 1982Assignee: El Paso Products CompanyInventor: Norbert F. Cywinski
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Patent number: 4365081Abstract: 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: GrantFiled: May 15, 1981Date of Patent: December 21, 1982Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.Inventors: Noboru Shimizu, Hiroshi Yoshida, Hiromiki Daigo, Shiyouichi Matumoto, Hiroyoshi Uchino
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Patent number: 4319980Abstract: 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: GrantFiled: March 7, 1980Date of Patent: March 16, 1982Inventor: Rodman Jenkins
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Patent number: 4311851Abstract: 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: GrantFiled: December 19, 1979Date of Patent: January 19, 1982Assignee: Chem Systems Inc.Inventors: John A. Jung, Jimmy Peress
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Patent number: 4299999Abstract: 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: GrantFiled: May 9, 1980Date of Patent: November 10, 1981Assignee: Institut Francais du petroleInventors: Paul Mikitenko, Lionel Asselineau
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Patent number: 4271315Abstract: 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: GrantFiled: November 15, 1979Date of Patent: June 2, 1981Assignee: El Paso Products CompanyInventor: Norbert F. Cywinski
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Patent number: 4262138Abstract: 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: GrantFiled: April 9, 1979Date of Patent: April 14, 1981Assignee: Chem Systems Inc.Inventor: Abraham P. Gelbein
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Patent number: 4260827Abstract: 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: GrantFiled: December 17, 1979Date of Patent: April 7, 1981Assignee: Bayer AktiengesellschaftInventors: Kurt Klinkmann, Raimund Wambach
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Patent number: 4256913Abstract: 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: GrantFiled: April 9, 1979Date of Patent: March 17, 1981Assignee: Chem Systems Inc.Inventors: John A. Jung, Jimmy Peress
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Patent number: 4250328Abstract: 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: GrantFiled: February 6, 1979Date of Patent: February 10, 1981Assignee: Kyowa Yuka Co., Ltd.Inventors: Kiyoshi Fujita, Yukiyoshi Ito, Shigeru Kamimori
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Patent number: 4243493Abstract: 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: GrantFiled: February 3, 1978Date of Patent: January 6, 1981Assignee: Mannesmannrohren-Werke A.G.Inventors: Kurt Gruber, Willi Keim, Klaus Hentschel
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Patent number: 4229263Abstract: 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: GrantFiled: December 21, 1978Date of Patent: October 21, 1980Assignee: Phillips Petroleum CompanyInventor: William V. Childs
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Patent number: 4163696Abstract: 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: GrantFiled: June 7, 1978Date of Patent: August 7, 1979Assignee: Arthur G. McKee & CompanyInventor: Wang-Mo Wong
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Patent number: 4053369Abstract: 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: GrantFiled: November 24, 1976Date of Patent: October 11, 1977Assignee: Phillips Petroleum CompanyInventor: Martin R. Cines
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Patent number: 4039395Abstract: 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: GrantFiled: August 11, 1975Date of Patent: August 2, 1977Assignee: Monsanto CompanyInventor: Roy T. Eby
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Patent number: RE31010Abstract: 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: GrantFiled: June 11, 1981Date of Patent: August 10, 1982Assignee: Chem Systems Inc.Inventor: Abraham P. Gelbein