Preparing By Alcoholysis, Hydrolysis Or Saponification Of An Ester Patents (Class 568/858)
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Patent number: 6867337Abstract: A process for producing glycerin is comprised of the steps of: (1) contacting a fat with water at a temperature and pressure sufficient to produce hydrolyzed fat and a sweet water stream comprised of water, fat and glycerin; (2) introducing the sweet water stream into a vertical constant temperature zone and heating the sweet water stream to a temperature of at least 200° C.; (3) allowing sweet water stream of step (2) to separate into a top layer comprised of fat and a bottom layer comprised of glycerin and water while maintaining a temperature of the two layers of at least about 200° C. for a period of time sufficient to deactivate the prions; (4) separating the glycerin from the water.Type: GrantFiled: September 23, 2003Date of Patent: March 15, 2005Assignee: Cognis CorporationInventors: Herbert C. Ahting, David A. Krabacher
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Patent number: 6835858Abstract: The invention relates to a method for the catalytic conversion of organic carbonate to the corresponding alcohol, wherein the organic carbonate is contacted with alcohol and/or water in the presence of a zinc supported catalyst.Type: GrantFiled: September 10, 2003Date of Patent: December 28, 2004Assignee: Shell Oil CompanyInventors: Johannes Petrus De Jonge, Jean-Paul Lange
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Patent number: 6740785Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: July 26, 2002Date of Patent: May 25, 2004Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Patent number: 6720448Abstract: The present invention relates to a method of recovering a solution comprising the chemical species obtained by depolymerization of PET from a material containing poly(ethylene terephthalate) in the form of bottles, by making said material react, in the absence of water, with a reagent consisting of one or more metal salts of a weaker acid than the terephthalic acid and of ethylene glycol, until a water-soluble intermediate product is obtained, and subsequently carrying out dissolution in water, stirring and filtering.Type: GrantFiled: October 2, 2001Date of Patent: April 13, 2004Inventor: Massimo Broccatelli
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Patent number: 6717001Abstract: A process for the vapor phase oxidation of ethylene to ethylene oxide, which process involves reacting a reaction mixture having ethylene and oxygen in the presence of a supported highly selective silver-based catalyst by: operating at an initial operation phase wherein fresh catalyst is used, and operating at a further operation phase when a cumulative ethylene oxide production exceeds 0.01 kT ethylene oxide per m3 of catalyst, wherein in said further operation phase the concentration of ethylene in the reaction mixture is increased; and a method of using ethylene oxide into the 1.2-ethanediol or the 1,2-ethanediol ether wherein the ethylene oxide has been obtained by the process for the production of ethylene oxide.Type: GrantFiled: December 6, 2002Date of Patent: April 6, 2004Assignee: Shell Oil CompanyInventors: Wayne Errol Evans, Peter Ingraham Chipman
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Publication number: 20040059164Abstract: A process for producing glycerin is comprised of the steps of: (1) contacting a fat with water at a temperature and pressure sufficient to produce hydrolyzed fat and a sweet water stream comprised of water, fat and glycerin; (2) introducing the sweet water stream into a vertical constant temperature zone and heating the sweet water stream to a temperature of at least 200° C.; (3) allowing sweet water stream of step (2) to separate into a top layer comprised of fat and a bottom layer comprised of glycerin and water while maintaining a temperature of the two layers of at least about 200° C. for a period of time sufficient to deactivate the prions; (4) separating the glycerin from the water.Type: ApplicationFiled: September 23, 2003Publication date: March 25, 2004Inventors: Herbert C. Ahting, David A. Krabacher
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Patent number: 6649792Abstract: The proposed method of chemical recycling of polyethylene terephthalate waste to terephthalic acid and ethandiol is based on a continuous series of gradual steps, namely (a) separation of the polyethylene terephthalate component of the input material by its conversion to brittle form through crystallization, grinding and subsequent sifting, followed by (b) continuous two-stage hydrolysis of the polyethylene terephthalate, carried out in the first stage by feeding steam to the polymer melt, and in the second stage, by the reaction of the products of the first stage of hydrolysis with ammonium hydroxide, followed by (c) condensation of terephthalic acid from an aqueous solution of the second-stage hydrolysis products by inorganic acid, and its separation by means of filtration, and finally (d) rectification separation of ethandiol from a solution of the products of the second stage of hydrolysis, after the separation of terephthalic acid.Type: GrantFiled: September 13, 2002Date of Patent: November 18, 2003Inventors: Milan {haeck over (S)}irek, Jaroslav Jirou{haeck over (s)}ek
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Publication number: 20030119666Abstract: A catalyst which contains at least one element selected from the group consisting of Group V elements, Group VI elements, Group VII elements, Group VIII elements, Group IX elements, Group X elements, and Group XI elements in the periodic table, and is to be used for subjecting an epoxy alcohol represented by a general formula (1) to a hydrogenolysis reaction in the presence of at least one solvent selected from the group consisting of ethers, esters, aromatic hydrocarbon compounds, alicyclic hydrocarbon compounds and aliphatic hydrocarbon compounds. By use of such a catalyst, a both end-hydroxyl group-terminated diol having a high purity can be produced efficiently.Type: ApplicationFiled: March 26, 2002Publication date: June 26, 2003Inventors: Yasushi Kadowaki, Masato Kaneda, Hiroshi Uchida
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Publication number: 20030105366Abstract: A method for catalytic conversion of alkylene carbonate, wherein alkylene carbonate is contacted with C1-C5 aliphatic alcohol and/or water in the presence of Mg, Al mixed (hydr) oxide catalyst having a Mg:Al molar ratio in the range of from 4 to 20.Type: ApplicationFiled: November 12, 2002Publication date: June 5, 2003Inventors: Johannes Petrus De Jonge, Jean-Paul Lange, Dennis Humphrey Louis Pello
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Patent number: 6555720Abstract: A method and system for producing 1,4-butanediol (1,4-BG), and optionally additionally tetrahydrofuran (THF), that promotes more efficient usage of water (H2O) is provided. In one aspect, the method is comprised of supplying at least one feed stream including 1,4-diacetoxybutane (1,4-DAB), 1,4-hydroxyacetoxybutane (1,4-HAB) and H2O to at least one reactor. 1,4-DAB, 1,4-HAB and H2O are reacted in the reactor to produce at least one effluent stream that includes 1,4-BG, 1,4-HAB, H2O, unreacted 1,4-DAB and acetic acid. The effluent stream is supplied to a separation system having one or more separators where at least a portion of the 1,4-HAB is removed from the effluent stream and recycled back to the reaction. Alternatively, 1,4-HAB may be supplied directly to the reactor as a feed stream, or a combination of feed stream and recycled 1,4-HAB may be used.Type: GrantFiled: April 28, 2000Date of Patent: April 29, 2003Assignee: Mitsubishi Chemical CorporationInventors: Lionel O'Young, Kazuyuki Ookubo, Nobuo Toratani, Hiroshi Iwasaka
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Publication number: 20030032840Abstract: The proposed method of chemical recycling of polyethylene terephthalate waste to terephthalic acid and ethandiol is based on a continuous series of gradual steps, namely (a) separation of the polyethylene terephthalate component of the input material by its conversion to brittle form through crystallization, grinding and subsequent sifting, followed by (b) continuous two-stage hydrolysis of the polyethylene terephthalate, carried out in the first stage by feeding steam to the polymer melt, and in the second stage, by the reaction of the products of the first stage of hydrolysis with ammonium hydroxide, followed by (c) condensation of terephthalic acid from an aqueous solution of the second-stage hydrolysis products by inorganic acid, and its separation by means of filtration, and finally (d) rectification separation of ethandiol from a solution of the products of the second stage of hydrolysis, after the separation of terephthalic acid.Type: ApplicationFiled: September 13, 2002Publication date: February 13, 2003Inventors: Milan Sirek, Jaroslav Jirousek
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Patent number: 6515036Abstract: A method of recovering a decomposition product from a polyurethane, the method comprising the steps of thermally decomposing a polyurethane into a liquid containing a polyol and a urea compound which is soluble in the polyol, and solids containing a urea compound which is insoluble in the liquid in the presence of a polyamine compound at a temperature of 120 to 250° C.; removing the solids; hydrolyzing the residue with water retained at a high temperature of 200 to 320° C. and a high pressure; and recovering the resulting polyamine and/or polyol.Type: GrantFiled: April 2, 2001Date of Patent: February 4, 2003Assignee: Mitsui Takeda Chemicals Inc.Inventors: Koichi Murayama, Katsuhisa Kodama, Takashi Kumaki
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Patent number: 6489373Abstract: The present invention provides a method of recovering a polyamine compound and/or a polyol compound useful for starting materials of polyurethane resin in an industrially advantageous manner by first dissolving the polyurethane resin such as polyurethane foams discharged in a large amount as industrial wastes in a solubilizing agent containing a polyamine compound, a low molecular glycol or an amino alcohol, hydrolyzing the resulting solution with liquid water at 200 to 320° C., then recovering the polyamino compound and/or polyol compound thus formed.Type: GrantFiled: October 1, 1999Date of Patent: December 3, 2002Assignee: Mitsui Takeda Chemicals Inc.Inventors: Katsuhisa Kodama, Kouichi Murayama, Takashi Kumaki
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Publication number: 20020065430Abstract: The present invention relates to a method of recovering a solution comprising the chemical species obtained by depolymerization of PET from a material containing poly(ethylene terephthalate) in the form of bottles, by making said material react, in the absence of water, with a reagent consisting of one or more metal salts of a weaker acid than the terephthalic acid and of ethylene glycol, until a water-soluble intermediate product is obtained, and subsequently carrying out dissolution in water, stirring and filtering.Type: ApplicationFiled: October 2, 2001Publication date: May 30, 2002Inventor: Massimo Broccatelli
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Patent number: 6380419Abstract: Ethylene glycol and a carbonate ester are simultaneously produced by reacting ethylene oxide and carbon dioxide to form ethylene carbonate, hydrolyzing of the solution containing the ethylene carbonate to obtain ethylene glycol, purifying ethylene glycol, transesterifying ethylene carbonate and a hydroxyl group-containing compound to form the corresponding carbonate ester and ethylene glycol, separating the carbonate ester and separating ethylene carbonate.Type: GrantFiled: January 17, 2001Date of Patent: April 30, 2002Assignee: Mitsubishi Chemical CorporationInventor: Kazuki Kawabe
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Publication number: 20020049258Abstract: The present invention provides a method of recovering a polyamine compound and/or a polyol compound useful for starting materials of polyurethane resin in an industrially advantageous manner by first dissolving the polyurethane resin such as polyurethane foams discharged in a large amount as industrial wastes in a solubilizing agent containing a polyamine compound, a low molecular glycol or an amino alcohol, hydrolyzing the resulting solution with liquid water at 200 to 320° C., then recovering the polyamino compound and/or polyol compound thus formed.Type: ApplicationFiled: October 1, 1999Publication date: April 25, 2002Inventors: KATSUHISA KODAMA, KOUICHI MURAYAMA, TAKASHI KUMAKI
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Patent number: 6329558Abstract: In a process for isolating alkylene glycol having a low aldehyde content, in which a mixture comprising alkylene glycol is subjected to a final distillation, formic acid or a formate or a mixture of two or more formates or a mixture of formic acid and one or more formates is present in the mixture comprising alkylene glycol.Type: GrantFiled: June 23, 2000Date of Patent: December 11, 2001Assignee: BASF AktiengesellschaftInventors: Jürgen Mohr, Toni Dockner
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Patent number: 6281394Abstract: A process for preparing vicinal diols or polyols from an organic reaction mixture containing formic esters of vicinal diols or polyols, in which water is added to the reaction mixture, without addition of bases, and the formic esters are hydrolyzed in a subsequent thermal treatment, the aqueous formic acid is removed, and vicinal diols or polyols remain behind.Type: GrantFiled: March 23, 2000Date of Patent: August 28, 2001Assignee: BASF AktiengesellschaftInventors: Alfred Oftring, Thomas Bogenstätter, Christian Ott
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Patent number: 6207850Abstract: A method is provided for co-producing dialkyl carbonate and alkanediol by reacting alkylene carbonate with alkanol in the presence of a IIIA metal oxide catalyst, preferably alumina.Type: GrantFiled: November 3, 1999Date of Patent: March 27, 2001Assignee: Mobil Oil CorporationInventors: Zhaozhong Jiang, Rene B. LaPierre, Jose G. Santiesteban, Hye Kyung Cho Timken, William A. Weber
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Patent number: 6187972Abstract: A process for producing an alkylene glycol, which is a continuous process for producing an alkylene glycol comprising the following steps (1) to (4), wherein the hydrolysis step (2) is divided into a plurality of stages, and the hydrolysis is carried out so that the water concentration in a reaction stage wherein the conversion of the alkylene carbonate is at least 60%, is from 15 to 30 wt %: (1) a carbonating step of reacting an alkylene oxide with carbon dioxide gas in the presence of a carbonating catalyst to form a reaction solution containing an alkylene carbonate, (2) a hydrolysis step of hydrolyzing the reaction solution obtained in step (1) while releasing carbon dioxide gas, to form an aqueous alkylene glycol solution, (3) a distillation step of distilling the aqueous alkylene glycol solution to obtain at least a dehydrated alkylene glycol and a solution containing the carbonating catalyst, and (4) a recycling step of supplying the solution containing the carbonating catalyst to the carbonating sType: GrantFiled: August 9, 1999Date of Patent: February 13, 2001Assignee: Mitsubishi Chemical CorporationInventors: Kazuki Kawabe, Kouichi Nagata
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Patent number: 6162940Abstract: A method is provided for co-producing dialkyl carbonate and alkanediol by reacting alkylene carbonate with alkanol in the presence of a complex salt catalyst having a formula A.sub.x (M.sub.y O.sub.z), wherein A is an alkali metal or alkaline earth metal, M is a Group 5 or Group 6 transition metal, O is oxygen, x is 1 or 2, y is 1 or 2, and z is an integer from 3 to 6.Type: GrantFiled: December 14, 1999Date of Patent: December 19, 2000Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Larry E. Hoglen, Zhaozhong Jiang, Rene B. LaPierre
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Patent number: 6080897Abstract: Disclosed is a method for producing monoethylene glycol, which is a method for producing ethylene glycol that comprises a carbonation step in which ethylene oxide is allowed to react with carbon dioxide in the presence of a carbonation catalyst thereby effecting formation of a reaction solution containing ethylene carbonate, a hydrolysis step in which the reaction solution is converted into an ethylene glycol aqueous solution by hydrolyzing ethylene carbonate in the reaction solution and a distillation step in which purified ethylene glycol and a catalyst solution containing the carbonation catalyst are obtained from the ethylene glycol aqueous solution by distillation, wherein the improvement resides in that the reaction is carried out in the presence of a carbonation catalyst using a bubble column reactor by supplying ethylene oxide, carbon dioxide and water into the reactor.Type: GrantFiled: March 18, 1999Date of Patent: June 27, 2000Assignee: Mitsubishi Chemical CorporationInventor: Kazuki Kawabe
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Patent number: 6023003Abstract: A process and a system is disclosed for recovering glycol from glycol and brine mixtures produced from oil or natural gas wells that combines energy efficiency with a capability for handling salt and other solids contained in the mixture. The system comprises three effect evaporator systems in series. Each effect evaporator system comprises an evaporator, a separator vessel, product pumps, and a solids removal system.The process utilizes the system to remove salt and other solids as well as excess water leaving a glycol stream that can be reused as a hydrate inhibitor. The process begins by preheating a glycol/brine stream comprising approximately fifty percent (50%) glycol. The stream is then subjected to three evaporation cycles. The first evaporation cycle comprises introducing the preheated stream into a suppressed boiling point evaporator where the stream is heated under a constant pressure. The stream pressure is then dropped to cause a portion of the water contained in the stream to vaporize or flash.Type: GrantFiled: January 13, 1998Date of Patent: February 8, 2000Assignee: Reading & Bates Development Co.Inventors: Timothy R. Dunning, Ralph L. Hicks, Rita W. Girau, Kiel M. Divens, Richard I. Evans
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Patent number: 5976202Abstract: Reaction products of polyolefins having predominantly a terminal double bond and a number average molecular weight of from 250 to 10,000, which possess an aliphatic hydrocarbon skeleton which is straight-chain or carries C.sub.1 -C.sub.4 -alkyl side chains, with from 1 to 10 mol, per equivalent of double bond, of one or more vinyl esters I ##STR1## are obtainable by reacting the stated polyolefins with the vinyl esters I in the presence of a free radical initiator at from 80 to 200.degree. C., it being possible for these reaction products subsequently to have been hydrolyzed to the corresponding alcohols or converted into the corresponding amines by reductive amination with amines II ##STR2## .Type: GrantFiled: July 20, 1995Date of Patent: November 2, 1999Assignee: BASF AktiengesellschaftInventors: Hans Peter Rath, Helmut Mach, Harald Schwahn, Hans-Joachim Muller, Wolfgang Reif, Thomas Ruhl
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Patent number: 5840553Abstract: A novel glycerol derivative, a process for preparing the same, and a process for preparing a triazole derivative. An optically active 2-arylglycerol derivative which is novel and useful as a synthetic intermediate of medicament is provided, and furthermore, (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)-propane-1,2-diol, which is useful as an antifungal agent, is prepared.Type: GrantFiled: March 11, 1997Date of Patent: November 24, 1998Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
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Patent number: 5808107Abstract: Preparation of 4-hydroxy substituted butyrolactones is described. A process for the preparation of 3-hydroxybutyrolactone, 1,2,4-trihydroxybutane and 3,4-dihydroxy acid methyl ester from malic acid is particularly described. The preparation of 4-hydroxymethyl-4-hydroxybutyric acid -1-methyl ester and 4-hydroxymethyl butyrolactone is particularly described. The compounds are intermediates to various pharmaceutical and agricultural products.Type: GrantFiled: October 31, 1997Date of Patent: September 15, 1998Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 5763691Abstract: The present invention relates to a process for producing ethylene glycol from ethylene oxide wherein ethylene oxide in a gas resulting from oxidation of ethylene is absorbed in a specific absorbing solution, is allowed to react with carbon dioxide, converted into ethylene carbonate, and then subjected to hydrolysis to produce ethylene glycol.According to the present invention, a large energy consuming step such as stripping of ethylene oxide and separation of excess amounts of water during the ethylene glycol production becomes unnecessary and the process can be greatly simplified by combining the ethylene oxide absorption step and the carbonation step.Type: GrantFiled: November 26, 1996Date of Patent: June 9, 1998Assignee: Mitsubishi Chemical CorporationInventors: Kazuki Kawabe, Kazuhiko Murata, deceased, Toshiyuki Furuya
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Patent number: 5672780Abstract: There is described a process for removing dimethyl terephthalate contaminants from ethylene glycol. The process comprises distilling ethylene glycol in the presence of an ester exchange catalyst to cause reaction between ethylene glycol and dimethyl terephthalate to form compounds that are less volatile than either ethylene glycol or dimethyl terephthalate, such as bishydroxyethyl terephthalate.Type: GrantFiled: July 26, 1996Date of Patent: September 30, 1997Assignee: Eastman Kodak CompanyInventors: William James Gamble, Andrius Algimantas Naujokas
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Patent number: 5635542Abstract: The present invention relates to a process for the production of hydroxyl-group-containing compounds suitable for the polyisocyanate polyaddition process from polyurea and/or polyurethane polyurea wastes by treating polyurea and/or polyurethane polyurea wastes with diols and/or polyols at temperatures from 160.degree. to 260.degree. C., the water present in the reaction vessel preferably being removed by distillation during the heating-up phase, characterized in that 1,3-dicarbonyl compounds are added to the reaction mixture before or during the reaction.Type: GrantFiled: June 16, 1995Date of Patent: June 3, 1997Assignee: Bayer AktiengesellschaftInventors: Thomas Munzmay, Werner Rasshofer, Walter Meckel
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Patent number: 5583270Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of productiong 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: June 23, 1994Date of Patent: December 10, 1996Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5493063Abstract: This invention provides a process for producing an optically active 1,2-diol derivative by optical resolution. The optically active 1,2-diol derivative of the formula (I) which is capable of utilizing as an intermediate of fungicidal optically-active azole derivatives can be produced by esterifying a 1,2-diol derivative of the formula (I) as a substrate with a carboxylic acid derivative of the formula (II) as a reagent in the presence of a lipase as a catalyst. ##STR1## wherein R.sup.1 is C1-C5 alkyl group, C3-C7 cycloalkyl group or C1-C5 haloalkyl group, R.sup.2 is C1-C3 alkyl group substituted by a phenyl group which may have one or two halogen atoms and/or C1-C4 alkyl groups, C2-C3 alkenyl group substituted by a phenyl group which may have one or two halogen atoms and/or C1-C4 alkyl groups, or C1-C3 alkyl group substituted by a phenoxy group which may have one or two halogen atoms and/or C1-C4 alkyl groups, R.sup.3 is C1-C10 alkyl group or aryl group, and R.sup.Type: GrantFiled: November 21, 1994Date of Patent: February 20, 1996Assignee: Kureha Kagaku Kogyo K.K.Inventors: Eisaku Takahashi, Takashi Kimura, Satoru Kumazawa
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Patent number: 5426217Abstract: A process for the production of terephthalic acid comprises subjecting polyalkylene terephthalate to hydrolysis using a ratio of water to polyalkylene terephthalate in the mixture prior to heating and carrying out the reaction under conditions such that, at the reaction temperature, a significant proportion of the terephthalic acid produced is in the solid phase. The degree of recrystallization necessary to recover the terephthalic acid produced is thereby reduced. The reaction can with advantage be carried out with alkylene glycol present in the mixture prior to hydrolysis.Type: GrantFiled: January 6, 1993Date of Patent: June 20, 1995Assignee: Imperial Chemical Industries, PLCInventors: David J. Royall, James L. Harvie
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Patent number: 5345004Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of producing 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: December 8, 1993Date of Patent: September 6, 1994Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5266716Abstract: A process for the continuous splitting of polycarbonates into dihydroxy compounds and carbonic acid esters is disclosed. Accordingly there are reacted in a distillation column a polycarbonate resin and a monohydroxy compound in the presence of a transesterification catalyst. The polycarbonate, in molten form or as a solute, is continuously fed into the upper part of the column and the monohydroxy compound in vapor phase is continuously fed into the lower part of the column. The resulting carbonic acid ester and dihydroxy compounds are continuously being removed from the column. The process is eminently suitable for the recycling of polycarbonate waste.Type: GrantFiled: December 9, 1992Date of Patent: November 30, 1993Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Norbert Schon, Steffen Kuhling
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Patent number: 5214182Abstract: A process is disclosed for the cogeneration of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a heterogeneous, phosphine-bound polymer catalyst. Dimethyl carbonate and ethylene glycol are generated in greater than 98% selectivity.Type: GrantFiled: July 1, 1991Date of Patent: May 25, 1993Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5210336Abstract: A process is provided for the conversion of an olefin to the corresponding glycol wherein a mixture of olefin, oxygen, carbon dioxide and water is reacted in a solvent at supercritical conditions with respect to the reaction mixture.Type: GrantFiled: January 24, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Anne M. Gaffney, John A. Sofranko
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Patent number: 4924026Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen, and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.Type: GrantFiled: August 11, 1989Date of Patent: May 8, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
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Patent number: 4822925Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.Type: GrantFiled: February 6, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4734518Abstract: A process is disclosed for the cosynthesis of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a homogeneous catalyst from the group consisting of soluble miscible tertiary phosphines arsines, and stibines and soluble, miscible bivalent sulphur and selenium compounds.Type: GrantFiled: January 12, 1987Date of Patent: March 29, 1988Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4691041Abstract: A process is disclosed for the preparation of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a series of heterogenous catalyst systems including ion exchange resins with tertiary amine, quaternary ammonium, sulfonic acid and carboxylic acid functional groups, alkali and alkaline earth silicates impregnated into silica and ammonium exchanged zeolites.Type: GrantFiled: January 3, 1986Date of Patent: September 1, 1987Assignee: Texaco Inc.Inventors: Roger G. Duranleau, Edward C. Y. Nieh, John F. Knifton
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Patent number: 4661609Abstract: A process is disclosed for the cosynthesis of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a catalyst selected from the group consisting of zirconium, titanium and tin.Type: GrantFiled: July 31, 1986Date of Patent: April 28, 1987Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4645855Abstract: A process for the preparation of succinic acid diesters by carbonylation of acrylic acid esters in the presence of alcohols, using a cobalt carbonyl complex as the catalyst and a heterocyclic nitrogen base as the promoter, at 80.degree.-200.degree. C. and under a carbon monoxide pressure of 60-300 bar, wherein the reaction is carried out in the presence of not less than 20% by weight, based on the amount of all the liquid constituents of the reaction mixture, of an inert liquid and the concentration of the acrylic acid ester is kept, for the predominant part of the reaction time, at below 15% by weight, again based on the amount of all liquid constituents.Type: GrantFiled: August 24, 1984Date of Patent: February 24, 1987Assignee: BASF AktiengesellschaftInventors: Johannes G. Reuvers, Wolfgang Richter, Rudolf Kummer
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Patent number: 4620032Abstract: There is disclosed a process for reducing the reaction time in the hydrolysis of a condensation polymer wherein molten condensation polymer is intimately admixed with a depolymerizing agent which is either (i) one of the products resulting from the complete hydrolytic depolymerization of the condensation polymer; or (ii) water. The depolymerization agent is present in the mixture in an amount which is less than the weight of the condensation polymer and the materials are intimately admixed for a time sufficient that the molecular of the condensation polymer is reduced by at least 50%. The treated condensation polymer of lower molecular weight is thereafter subjected to neutral hydrolysis. In addition to decreasing the overall time required to effect complete hydrolytic depolymerization, this process additionally permits the use of a smaller hydrolysis vessel, thereby reducing the fabrication cost of the hydrolysis unit.Type: GrantFiled: December 11, 1984Date of Patent: October 28, 1986Assignee: Celanese CorporationInventor: Marvin L. Doerr
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Patent number: 4602102Abstract: It has been surprisingly discovered in accordance with the present invention that when dimethoxymethane is reacted with formaldehyde in the presence of an organic peroxide, the reaction preferentially involves an addition of the formaldehyde to the dimethoxymethane to provide a reaction product containing alkyl glycolates such as methyl glycolate and ethyl glycolate as principle products of the reaction. The alkyl glycolates are useful as raw materials for the manufacture of ethylene glycol.Type: GrantFiled: December 19, 1984Date of Patent: July 22, 1986Assignee: Texaco Inc.Inventors: Ernest L. Yeakey, John R. Sanderson
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Patent number: 4602103Abstract: C.sub.4 olefins comprising cis- and trans-butane-2 and butene-1 may be oxidized to their corresponding mono- and diacetates in the presence of acetic acid and an olefin-activated palladium catalyst under mild conditions. With this catalyst, and depending in part upon the solvent employed, as well as other operating conditions, the formation of linear allylic 1-acetates over the corresponding branched compounds can be favored in order to increase the yield of the corresponding linear 1,4-diacetates. The latter, in turn, may then be converted, for example, to butanediol by known hydrogenation methods.In a similar manner, isobutylene may be converted to a dialcohol.Type: GrantFiled: April 10, 1985Date of Patent: July 22, 1986Assignee: Sun Refining and Marketing CompanyInventor: James E. Lyons
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Patent number: 4578510Abstract: A process is described for reducing the amount of low molecular weight oligomers formed during the hydrolysis of a condensation polymer. This process comprises the neutral aqueous hydrolysis of a condensation polymer in which conditions are controlled such that the following two conditions are met:(1) the amount of water and the condensation polymer present in the hydrolysis zone are such that the least soluble final depolymerization product would not exceed its solubility limits, assuming all of the polymer is converted to final depolymerization products; and(2) temperature conditions and aqueous concentration of final depolymerization products are controlled so that at equilibrium, the amount of low molecular weight oligomers is no greater than 7% of the theoretical, based on the amount of polymer added.Type: GrantFiled: December 11, 1984Date of Patent: March 25, 1986Assignee: Celanese CorporationInventor: Marvin L. Doerr
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Patent number: 4578502Abstract: Solid scrap polyethylene terephthalate (PET) resin may be reprocessed by depolymerizing said scrap in the presence of water or methanol, recovering the monomers resulting from the depolymerization reaction and repolymerizing the monomers to form polymeric polyethylene phthalate.Type: GrantFiled: January 22, 1985Date of Patent: March 25, 1986Inventor: Warner J. G. Cudmore
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Patent number: 4556748Abstract: Prepare alkylene glycols by hydrolyzing alkylene carbonates under specific conditions, and a reactor specially designed therefor.Type: GrantFiled: October 31, 1983Date of Patent: December 3, 1985Assignee: The Dow Chemical CompanyInventors: Albert C. Tsang, Thomas L. Holland, Johnny W. Masey
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Patent number: 4544767Abstract: Hydrogenation of an acyloxyolefin is effected in the presence of at least one of an alkali and an alkaline earth metal salt of a carboxylic acid. In one embodiment, 1,4-diacetoxy-2-butene is converted to 1,4-diacetoxybutane employing potassium acetate.Type: GrantFiled: August 1, 1980Date of Patent: October 1, 1985Assignee: Phillips Petroleum CompanyInventor: Kiplin D. Cowan
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Patent number: 4524224Abstract: This invention is concerned with producing glycols of the formulaHOCHRCH.sub.2 OHfrom hydrolysis, in a homogeneous liquid phase mixture, of an alkylene carbonate of the formula ##STR1## in which R is either hydrogen or methyl. This is accomplished by using an amount of water in excess of stoichiometry and using potassium carbonate as the preferred catalyst. The reaction is effected under a carbon dioxide pressure of at least 80 psig and the reaction temperature is desirably between about 85.degree. C. and 500.degree. C.Type: GrantFiled: May 20, 1983Date of Patent: June 18, 1985Assignee: Union Carbide CorporationInventors: Glenn A. Taylor, Philip F. Wolf