Purification Or Recovery Patents (Class 549/541)
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Patent number: 6316641Abstract: The invention concerns a method for preparing an epoxide, in particular glycidol, wherein a cyclic organic carbonate, in particular glycerol carbonate, is heated under reduced pressure so as to carry out a reaction to contract the carbonate ring into an epoxide ring. According to the present invention, the reaction is carried out in a solid/liquid system in the presence of a polyol and a solid catalyst consisting of a type A zeolite or &ggr;-alumina. The method, which may be carried out continuously, enables the epoxide to be formed in a single step, the epoxide being exhausted in the form of vapor which only has to be extracted and separated from the carbon dioxide formed.Type: GrantFiled: September 8, 1999Date of Patent: November 13, 2001Assignee: Organisation Nationale Interprofessionelle des Oleagineux (O.N.I.D.OL.)Inventors: Jeong-Woo Yoo, Zéphirin Mouloungui, Antoine Gaset
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Patent number: 6278003Abstract: A process for refining epoxy compounds, wherein the process comprises: (a) providing a washed and dried organic phase comprising at least one epoxide compound; (b) contacting the organic phase with at least one basic solid selected from the group consisting of aluminum oxides, aluminum hydroxides and alkali metal silicates; and (c) separating the organic phase and the at least one basic solid, is disclosed.Type: GrantFiled: June 27, 2000Date of Patent: August 21, 2001Assignee: Cognis Deutschland GmbHInventor: Ralf Bohlander
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Patent number: 6211389Abstract: In accordance with the present invention, methods have been developed for the reduction of the chloride content of epoxy compound starting materials. Invention methods comprise subjecting specifically defined combinations comprising an epoxy resin starting material and other components to conditions sufficient to produce a treated epoxy compound (i.e., an epoxy compound having a chloride content which is reduced relative to that of the epoxy resin starting material), and separating the treated epoxy compound from the combination. Other components contemplated for use in the practice of the present invention comprise, alternatively, mixtures of crown ether, organic solvent and suitable base; mixtures of crown ether-like solvent and suitable base; mixtures of aprotic solvents and hydrides (other than tin hydride); mixtures of nonhalogenated organic solvent and reducing metal; and the like. In accordance with a further aspect of the present invention, products (i.e.Type: GrantFiled: May 23, 2000Date of Patent: April 3, 2001Assignee: Dexter CorporationInventor: Mark Thomas Dimke
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Patent number: 6136991Abstract: The invention provides for a purified glycidyl ester product prepared from neo acids wherein said ester product is recovered as a light fraction from a glycidyl ester reaction product composition that has been subjected to conditions of temperature and vacuum in a thin film, short pass distillation evaporator, said purified glycidyl ester product further characterized that its polymerizable reaction product with methacrylic acid has a higher effective glass transition temperature as compared with the polymerizable reaction product with methacrylic acid of said glycidyl ester reaction product composition prior to purification.Type: GrantFiled: November 10, 1997Date of Patent: October 24, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Richard William Ryan, Gerald G. McGlamery, Jr., Ralph Martin Kowalik, Michael J. Keenan
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Patent number: 6127558Abstract: Epoxy resins which are diglycidyl ethers of tetrabromobisphenol A having a crystalline structure and in particulate form have an epoxy equivalent weight between 320 and 380 g/eq and a chlorine content that is smaller than 0.3%.Type: GrantFiled: May 5, 1998Date of Patent: October 3, 2000Assignee: Bromine Compounds Ltd.Inventors: Yoav Bar-Yaakov, Daniel Plewinski
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Patent number: 6123812Abstract: A process for distilling ethylene oxide out of a mixture including ethylene oxide in a column at an absolute pressure of from 2 to 10 bar and a temperature of 20 to 180.degree. C. by withdrawing pure ethylene oxide in the liquid or gaseous state overhead or via a sidestream in the rectifying section of the column includes effecting the distillation in a column having on its inside a plurality of successive zones of structured sheet-metal packing or dumped beds of packing elements, these zones being assigned one or more extinguishing systems on the outside of the column.Type: GrantFiled: May 18, 1998Date of Patent: September 26, 2000Assignee: BASF AktiengesellschaftInventors: Bernd Bessling, Sebastian Zeck, Jurgen Pluckhan, Thomas Mayer, Ulrich Loffler, Gunter Spiegel, Rubens Ballenweg, Gerhard Brudi, Klaus Gieselberg, Lutz Hilprecht, Winfried Terjung, Heinz Auer, Axel Werner Polt, Stephan Scholl
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Patent number: 6040337Abstract: Compounds useful as angiogenesis inhibiting agents and processes for their preparation are disclosed. In one embodiment, the compounds of the invention are represented by Formula 1: ##STR1## Also disclosed is a pharmaceutical composition for inhibiting angiogenesis in a mammal, said composition comprising a compound of Formula 1, or a pharmaceutically acceptable salt thereof, as an active ingredient.Type: GrantFiled: May 13, 1999Date of Patent: March 21, 2000Assignee: Chong Kun Dang CorporationInventors: Chung Hong, II, Jung Woo Kim, Sang Joon Lee, Soon Kil Ahn, Nam Song Choi, Ryung Kee Hong, Hyoung Sik Chun, Seung Kee Moon, Hong Woo Lee
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Patent number: 6024839Abstract: A method of inhibiting fouling of one or more pieces of equipment for processing crude epichlorohydrin by treating at least one epichlorohydrin stream entering or exiting the one or more pieces of equipment with hydroquinone as an antifoulant.Type: GrantFiled: November 6, 1997Date of Patent: February 15, 2000Assignee: Shell Oil CompanyInventor: Duane Mark Schufeldt
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Patent number: 5958192Abstract: An extractive distillation agent used for the distillation of propylene oxide contaminated with water, acetone, acetaldehyde and methanol and consisting essentially of ethylene glycol monomethyl ether is fed to an extractive distillation column within about 2 to about 15 stages from the top of the tower to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone, acetaldehyde and methanol, and a heavier bottoms distillation fraction containing substantially all of the ethylene glycol monomethyl ether, water and acetone and some of the methanol introduced into the distillation column.Type: GrantFiled: August 27, 1997Date of Patent: September 28, 1999Assignee: Huntsman Specialty Chemicals CorporationInventor: Peter Stephen Morford
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Patent number: 5883264Abstract: Process for preparing optically active trans-3-phenylglycidamide compound, which comprises subjecting racemic trans-3-phenylglycidamide compound of the formula (I) ##STR1## wherein Ring A is substituted or unsubstituted benzene, and R.sup.1 is H or lower alkyl, to optical resolution using a microorganism having ability of preferentially hydrolyzing one of (2S,3R) isomer or (2R,3S) isomer thereof, and process for preparing an optically active 1,5-benzothiazepine derivative from the thus-obtained optically active trans-3-phenylglycidamide compound.Type: GrantFiled: March 6, 1997Date of Patent: March 16, 1999Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Hiroaki Matsumae, Akiko Idei, Takuo Nishida, Yasuhiko Ozaki, Takeji Shibatani
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Patent number: 5880297Abstract: A process for the distillation of the glycidyl ester reaction product of a straight or branched chain saturated monocarboxylic acid or salt thereof and an halo-substituted monoepoxidc is disclosed, wherein the reaction product is subjected to conditions of temperature and vacuum in a thin film, short pass distillation apparatus such as a wiped film evaporator. The product distillate has significantly reduced color than the reaction product prior to distillation, and has improved heat and color stability.Type: GrantFiled: May 21, 1997Date of Patent: March 9, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Richard William Ryan, Gerald G. McGlamery, Jr., Ralph Martin Kowalik
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Patent number: 5849938Abstract: Propylene is separated from the methanol present as a solvent in a crude olefin epoxidation product by means of an extractive distillation wherein a relatively heavy polar solvent having hydroxy groups such as water or propylene glycol is used as the extractive solvent. The method is also useful for removing water and impurities such as acetaldehyde from the propylene oxide.Type: GrantFiled: September 2, 1997Date of Patent: December 15, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Michael A. Rueter, John C. Jubin, Jr.
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Patent number: 5834570Abstract: An epoxy resin composition of this invention is obtained by solidifying epoxy resins represented by the following general formula (1) (wherein G is glycidyl group and R.sup.1 to R.sup.8 are hydrogen atoms, halogen atoms or hydrocarbon groups with 1 to 6 carbon atoms, and n is an integer of 0 to 10) by crystallization and adding epoxy resin curing agents to the resulting solid. It shows good flow and low moisture absorption, cures with excellent heat resistance at soldering temperature and is useful for a variety of applications, in particular, for encapsulating semiconductor devices.Type: GrantFiled: August 27, 1997Date of Patent: November 10, 1998Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Masashi Kaji, Takanori Aramaki, Kazuhiko Nakahara, Hisayuki Nagino
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Patent number: 5830324Abstract: In the continuous purification of a propylene oxide feedstock contaminated with water, methanol and acetone wherein an acetone buffer is established in the column, normal distillation conditions are maintained or restored during or after an upset by continuously monitoring predetermined distillation conditions in the acetone buffer zone, and adding additional acetone to the extractive distillation column when the monitored distillation condition deviates from a predetermined value by a predetermined amount.Type: GrantFiled: October 17, 1996Date of Patent: November 3, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: James Joseph Downs, Andrew Charles Hiester, Mark Elliott Taylor, Mark Allan Mueller, Michael Warren Peters, William Pleasie Nelson
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Patent number: 5772854Abstract: In the purification of an aqueous acetone-contaminated propylene oxide feedstock in an extractive distillation column in the presence of an oxyalkylene glycol extractive distillation agent under distillation conditions selected to promote the formation and maintenance of an acetone buffer in the distillation column, a higher boiling (heavier) distillation fraction containing substantially all of the oxyalkylene glycols, water, and acetone introduced into the extractive distillation column is continuously withdrawn and the higher boiling (heavier) distillation fraction is partially vaporized in a first reboiler; the remaining liquid being partially vaporized in a second reboiler and the vapors being recycled to the extractive distillation column.Type: GrantFiled: August 17, 1995Date of Patent: June 30, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: William Pleasant Nelson, Mark Elliott Taylor
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Patent number: 5756780Abstract: Disclosed are an improvement of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate, and a stabilized 3,4-epoxycyclohexyl methyl(meth)acrylate.Type: GrantFiled: August 23, 1996Date of Patent: May 26, 1998Assignee: Daicel Chemical Industries, Ltd.Inventors: Kyuichi Ohyama, Akira Horiguchi
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Patent number: 5693193Abstract: Propylene oxide is recovered through the use of an additive in a distillation solution, resulting in suppressed side reactions and reduced loss of product. Propylene oxide is produced by oxidizing ethylbenzene in a liquid phase with molecular oxygen to a obtain a reaction liquid containing ethylbenzene hydroperoxide; distilling the reaction liquid to obtain a concentrated solution of ethylbenzene hydroperoxide; further mixing and reacting the concentrated solution with propylene to obtain a mixed solution containing propylene oxide; and distilling the mixed solution to separate and recover propylene oxide. At least one compound selected from aliphatic saturated alcohols having 2 to 4 carbon atoms, allyl alcohol, saturated aliphatic hydrocarbons having 6 or 7 carbon atoms, benzene, ethers, ketones, nitriles, amines, pyridines, diamines, and aminoalcohols is added to the mixed distillation solution in an amount of 0.01-100 parts by weight per 100 parts by weight of propylene oxide.Type: GrantFiled: March 23, 1995Date of Patent: December 2, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi DeGuchi, Kazuo Kimura, Naoto Meki, Masaru Ishino, Tetsuya Suzuta
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Patent number: 5637740Abstract: The reaction mixture obtained in the production of 2,3-epoxypropyltrialkylammonium chlorides by treatment of chlorohydroxypropyltrialkylammonium chlorides with alkaline acting materials in aqueous medium containing impurities which create problems in the subsequent use of the 2,3-epoxypropyltrialkylammonium chloride. According to the invention the reaction mixture is freed from these impurities by separating it from undissolved impurities by employing at least about 0.2 mole of 2,3-epoxypropyltrialkylammonium chloride per mole of water.Type: GrantFiled: March 8, 1995Date of Patent: June 10, 1997Assignee: Degussa AktiengesellschaftInventors: Wolfgang Fischer, Manfred Langer, Gert Roessler
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Patent number: 5620568Abstract: An extractive distillation agent of 1-propanol is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate fraction of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the 1-propanol, water and acetone, some of the methanol and heavier by-products of propylene oxide formed in the distillation column.Type: GrantFiled: June 3, 1996Date of Patent: April 15, 1997Assignee: Texaco Chemical, Inc.Inventors: William A. Smith, Mark A. Mueller
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Patent number: 5576362Abstract: An insulating material characterized by that said insulating material is made by curing a mixture composed of a bisphenol A type epoxy resin having purity which is equal to or more than 90% and an organic filler, the thermal conductivity thereof is in a range of 5.0.times.10.sup.-3 to 18.0.times.10.sup.-3 (cal/.degree.C..multidot.cm.multidot.sec) and the glass transition temperature thereof is in a range of 164.degree. to 240.degree. C.Type: GrantFiled: April 20, 1993Date of Patent: November 19, 1996Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Chiharu Watanabe, Tatsuo Nakano, Kazuo Kato
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Patent number: 5559255Abstract: The present invention relates to a method of recovering ethylene oxide comprising the steps of:bringing a mixed gas containing ethylene oxide into contact with an absorbent so as to cause the absorbent to absorb the ethylene oxide; andstripping and separating said ethylene oxide to recover it from the absorbent, where the absorbent contains propylene carbonate. By employing the present invention, it is possible to reduce the heat recovery loss resulting from cooling the absorbent at the time of transfer from the stripping step to the absorption step, to about one-third that compared with a conventional system using water, without producing the by-product ethylene glycol.Type: GrantFiled: September 5, 1995Date of Patent: September 24, 1996Assignee: Mitsubishi Chemical CorporationInventors: Kazuki Kawabe, Kazuhiko Murata, Toshiyuki Furuya
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Patent number: 5547758Abstract: An insulating material characterized by that said insulating material is made by curing a mixture composed of a bisphenol A type epoxy resin having purity which is equal to or more than 90% and an organic filler, the thermal conductivity thereof is in a range of 5.0.times.10.sup.-3 to 18.0.times.10.sup.-3 (cal/.degree. C..multidot.cm.multidot.sec) and the glass transition temperature thereof is in a range of 164.degree. to 240.degree. C.Type: GrantFiled: March 2, 1995Date of Patent: August 20, 1996Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Chiharu Watanabe, Tatsuo Nakano, Kazuo Kato
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Patent number: 5527927Abstract: There are disclosed a process for producing glycidyl acrylate or glycidyl methacrylate by the transesterification of glycidol and methyl methacrylate, etc. which process comprises carrying out the transesterification in the presence of a polymerization inhibitor by using, as a catalyst, a quaternary ammonium salt represented by the general formula (I) or a quaternary phosphonium salt represented by the general formula (II)(R.sup.1 R.sup.2 R.sup.3 R.sup.4)NX (I)(R.sup.1 R.sup.2 R.sup.3 R.sup.4)PX (II)wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each an alkyl group having 1 to 20 carbon atoms, or the like, and X is a cyanide ion, cyanate ion or the like to complete the reaction; thereafter arresting the reaction by adding a catalyst deactivator represented by the general formula (III)SB (iii)wherein S is a sulfonic acid or a heteropolyacid and B is an alkali metal excluding potassium or an alkaline earth metal; and distilling away unreacted methyl methacrylate, etc.Type: GrantFiled: May 10, 1995Date of Patent: June 18, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masahiro Kurokawa, Akihiro Honma, Tsuyoshi Isozaki
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Patent number: 5519152Abstract: A process of manufacturing ethylene oxide is presented in ethylene and free oxygen are reacted in the presence of methane, carbon dioxide, and argon in a reactor to form an effluent comprising ethylene oxide; the effluent is then withdrawn and ethylene oxide is removed from the effluent to obtain a recycle stream; carbon dioxide and argon are removed from the recycle stream to obtain a treated recycle stream which is supplied to the reactor along with additional reactants and methane, wherein removing argon comprises separating a side stream from the recycle stream, passing the side stream to the feed inlet of a membrane unit, removing an argon-containing stream from the permeate outlet of the membrane unit, removing a retentate stream from the retentate outlet of the membrane unit, adding the retentate stream to the recycle stream, and purging the permeate side of the membrane unit with inert gas.Type: GrantFiled: April 5, 1995Date of Patent: May 21, 1996Assignee: Shell Oil CompanyInventor: Jeffrey P. Gorcester
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Patent number: 5514818Abstract: A method of resolving a mixture of stereoisomers of an aliphatic epoxide containing two or less oxygen atoms is provided. The method comprises utilizing a polysaccharide or a derivative thereof as a resolving agent.Type: GrantFiled: February 10, 1995Date of Patent: May 7, 1996Assignee: Daicel Chemical Industries, Ltd.Inventor: Kozo Tachibana
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Patent number: 5503813Abstract: Epoxidate from the molybdenum catalyzed epoxidation of an olefin such as propylene with a hydroperoxide such as ethylbenzene hydroperoxide is treated with 2 to 15 times the stoichiometric equivalent of aqueous base such as sodium hydroxide to form Na.sub.2 MoO.sub.4 and the resulting mixture is phase separated to separate an organic phase reduced in molybdenum and a net aqueous stream containing removed molybdenum, the mass ratio of the organic phase to the net aqueous stream being 450-3,000/I.Type: GrantFiled: May 12, 1995Date of Patent: April 2, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Thomas I. Evans
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Patent number: 5489366Abstract: A distillation method for the purification of crude propylene oxide containing contaminating quantities of water and methanol by partially purifying the crude propylene oxide in a plural stage distillation zone to provide a vaporized overhead distillate propylene oxide fraction containing a minor contaminating amount of vaporized water, andpassing the propylene oxide vapor fraction through a drying chamber containing a porous hygroscopic solid absorbent to selectively absorb water vapor onto the absorbent,and liquefying and recovering the thus-dehydrated purified propylene oxide.Type: GrantFiled: March 28, 1994Date of Patent: February 6, 1996Assignee: Texaco Chemical Inc.Inventor: Huibert S. Jongenburger
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Patent number: 5478954Abstract: Process for preparing highly pure enantiomers of oxirane alcohols, which comprises recrystallizing a mixture of the isomeric oxirane alcohols, in which the desired enantiomer is present in an excess of at least 60% ee, in a solvent or solvent mixture at a temperature just below the melting point of the oxirane alcohol.Oxirane alcohols prepared according to the invention are distinguished by high enantiomer purity. Ferroelectric liquid crystals, which contain highly pure enantiomers of oxirane alcohols according to the invention and/or derivatives derived therefrom, have particularly short switching times.Type: GrantFiled: July 28, 1993Date of Patent: December 26, 1995Assignee: Hoechst AktiengesellschaftInventor: Javier Manero
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Patent number: 5464505Abstract: Propylene oxide adducts of oxyethylene glycols are used as extractive distillation agents in an extractive distillation column in the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead propylene oxide distillate fraction contaminated with reduced quantities of water, acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the extractive distillation agent, and acetone and some of the methanol and water introduced into the distillation column.Type: GrantFiled: May 31, 1994Date of Patent: November 7, 1995Assignee: Texaco Chemical Inc.Inventors: Michael W. Peters, William A. Smith, Mark A. Mueller, William K. Culbreth, III
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Patent number: 5453521Abstract: Process for producing 10-deacetylbaccatin III from the various parts of the yew (Taxus sp.) by extraction and selective crystallization from a methanolic extract of the plant mass.Type: GrantFiled: September 17, 1993Date of Patent: September 26, 1995Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Claude Gaullier, Bernadette Mandard, Rodolphe Margraff
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Patent number: 5453160Abstract: An extractive distillation agent comprising a mixture of polyoxypropylene glycols is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate anhydrous propylene oxide fraction contaminated with reduced quantities of methanol and a heavier bottoms distillation fraction containing the polyoxypropylene glycols, water and acetone and some of the methanol introduced into the distillation column.Type: GrantFiled: May 31, 1994Date of Patent: September 26, 1995Assignee: Texaco Chemical Inc.Inventors: Michael W. Peters, William K. Culbreth, III, Mark A. Mueller
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Patent number: 5446176Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl (meth)acrylate and 3,4-epoxycyclohexyl methyl (meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl (meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl (meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.Type: GrantFiled: January 10, 1995Date of Patent: August 29, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Akihiro Kuwana, Kimihide Honda, Kunio Koga
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Patent number: 5405977Abstract: A method for removing organic halide contaminants from alkylene carbonates is disclosed. Organic halide contaminants are removed from alkylene carbonates by contacting the contaminated alkylene carbonate with hydrotalcite.Type: GrantFiled: January 4, 1993Date of Patent: April 11, 1995Assignee: Huntsman CorporationInventors: Michael Cuscurida, Edward T. Marquis
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Patent number: 5384420Abstract: A gas stream from a reaction in which ethylene oxide is produced by reacting ethylene with oxygen which gas stream comprises oxides of nitrogen and steam the gas stream is cooled to condense water, condensed water is removed, and ethylene oxide is then recovered from the gas stream. A substantial amount of the oxides of nitrogen is removed from the gas stream during the condensation.Type: GrantFiled: February 19, 1993Date of Patent: January 24, 1995Assignee: Imperial Chemical Industries plcInventors: James R. Jennings, Percy Hayden, Andrew J. Allchurch
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Patent number: 5382676Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate and 3,4-epoxyeyclohexyl methyl(meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl(meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl(meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.Type: GrantFiled: August 19, 1993Date of Patent: January 17, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Akihiro Kuwana, Kimihide Honda, Kunio Koga
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Patent number: 5354430Abstract: Contaminants are removed from impure propylene oxide by fractionating in a first column to remove overhead essentially all of the pentenes and pentanes and most of the oxygen-containing impurities to provide a partially purified first propylene oxide bottoms fraction, extractively distilling the first bottoms fraction in a second extractive column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a second overhead fraction comprising propylene oxide, hexenes, hexanes, water, residual quantities of pentenes and pentanes and oxygen-containing impurities, extractively distilling the second overhead fraction in a third column using a C.sub.6 to C.sub.10 alkane hydrocarbon extractive distillation agent to form a third bottoms fraction comprising the extractive distillation agent, propylene oxide, hexenes, hexanes, residual quantities of pentenes and pentanes and water, and extractively distilling said third bottoms fraction in a fourth column using a C.sub.6 to C.sub.Type: GrantFiled: October 26, 1993Date of Patent: October 11, 1994Assignee: Texaco Chemical CompanyInventors: William K. Culbreth, III, Yu-Hwa E. Sheu, David G. Pottratz
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Patent number: 5354431Abstract: Crude propylene oxide is purified by a distillation process wherein it is (a) extractively distilled in a first column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a first overhead fraction comprising propylene oxide, C.sub.5 -C.sub.7 hydrocarbons, methanol, water and oxygen-containing impurities, (b) wherein the first overhead fraction is separated in a plurality of intermediate distillation columns to provide an intermediate propylene oxide overhead fraction consisting essentially of propylene oxide and water, and (c) the intermediate propylene oxide overhead fraction is charged to a final distillation column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a final overhead fraction consisting essentially of propylene oxide.Type: GrantFiled: September 23, 1993Date of Patent: October 11, 1994Assignee: Texaco Chemical CompanyInventor: Mark E. Taylor
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Patent number: 5340446Abstract: An extractive distillation agent consisting essentially of a mixture of triethylene glycol with a lower boiling cosolvent selected from the group consisting of 2-methyl-2,4-pentanediol, tertiary butyl alcohol and ethylene glycol is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the extractive distillation agent, water and acetone and some of the methanol introduced into the distillation column.Type: GrantFiled: October 23, 1992Date of Patent: August 23, 1994Assignee: Texaco Chemical CompanyInventors: William P. Nelson, William A. Smith
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Patent number: 5296618Abstract: A method is provided for supplying the desired optical isomer of a derivative of epoxypropionic acid from a racemix mixture. A representative derivative of epoxypropionic acid is an ester of (p-methoxyphenyl)epoxypropionic acid. The racemic mixture initially is dissolved in carbon dioxide and the resulting solution is passed through a chromatographic column. The desired isomer is subsequently separated from the resulting eluant. In a preferred embodiment the chromatographic column is packed with microcrystallized cellulosetriacetate, cellulose-tris-(3,5-dimethylphenylcarbamate), or cellulose-tris-(p-methylphenylcarbamate).Type: GrantFiled: May 10, 1993Date of Patent: March 22, 1994Assignee: Orion-yhtyma Oy FermionInventors: Olli Aaltonen, Veikko Komppa, Martti Alkio, Pekka Kairisalo, Martti Hytonen, Anneli Hase
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Patent number: 5294683Abstract: There is disclosed a solid composition of polyglycidyl compounds having a molecular weight of less than 1500, which composition consists of one or more than one solid polyglycidyl compound and altogether not less than 5% by weight of one or of a mixture of more than one polyglycidyl compound, which compound or mixture is normally in liquid form, said amount being based on the total amount of all polyglycidyl compounds in the composition, which composition contains the said solid polyglycidyl compounds or at least part of the said solid polyglycidyl compounds in form of one or a mixture of more than one solid mixed phase, which solid mixed phase or mixture of more than one solid mixed phase essentially comprises the total amount of the polyglycidyl compounds which are normally in liquid form as additional component or components.Type: GrantFiled: September 28, 1992Date of Patent: March 15, 1994Assignee: Ciba-Geigy CorporationInventors: Jacques-Alain Cotting, Philippe-Guilhaume Gottis
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Patent number: 5288882Abstract: A method of recovering optically active epoxy alcohols from asymmetric epoxidation reaction mixture is provided whereby the epoxy alcohol may be obtained in high yield with minimal degradation of optical purity. The process is also suitable for the synthesis of useful organic sulfonate derivatives of chiral epoxy alcohols.Type: GrantFiled: December 21, 1992Date of Patent: February 22, 1994Assignee: Arco Chemical Technology, L.P.Inventors: T. Thomas Shih, Wilfred P.-S. Shum
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Patent number: 5262017Abstract: Impure propylene oxide is purified by a distillation process wherein it is (a) extractively distilled in a first column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a first overhead fraction comprising propylene oxide, C.sub.5 -C.sub.7 hydrocarbons methanol, water and oxygen-containing impurities, (b) wherein the first overhead fraction is separated in a second column into a second overhead fraction comprising most of the pentanes, pentenes and oxygen-containing impurities and a partially purified propylene oxide bottoms fraction comprising propylene oxide, hexenes, hexanes, and only residual quantities of pentenes and pentanes, (c) wherein the partially purified bottoms fraction is extracting distilled in a third column using a C.sub.7 -C.sub.Type: GrantFiled: April 19, 1993Date of Patent: November 16, 1993Assignee: Texaco Chemical CompanyInventors: Robert A. Meyer, William A. Smith, Mark A. Mueller, Gregory B. Demoll
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Patent number: 5256803Abstract: A method for preparing .beta.-phenylglycidic-(2R, 3R) acid optionally in the form of salt or ester by precipitation of the salt of the .beta.-phenylglycidic-(2R,3R) acid with (+)-.alpha.-methylbenzylamine-(R) in a solution of a mixture of salts of cis and trans .beta.-phenylglycidic acids with (+)-.alpha.-methylbenzylamine(R)- and the use of the resulting product for preparing taxol and its analogs.Type: GrantFiled: August 21, 1992Date of Patent: October 26, 1993Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Pierre Duchesne, Michel Mulhauser
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Patent number: 5252759Abstract: Organic sulfonate derivatives of optically active epoxy alcohols such as (R)- or (S)- glycidol are conveniently prepared from aqueous solutions of the epoxy alcohols.Type: GrantFiled: January 29, 1993Date of Patent: October 12, 1993Assignee: Arco Chemical Technology, L.P.Inventor: Wilfred P. Shum
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Patent number: 5248794Abstract: A process for purifying propylene oxide containing an unacceptable quantity of a poly(propylene oxide) polymer contaminant having a molecular weight of at least about 50,000, comprising the step of filtering propylene oxide containing such polymer contaminant through one or more membranes to provide a propylene oxide product fraction having an acceptable quantity of poly(propylene oxide) polymer contaminant therein and a second fraction which is more highly concentrated in such polymer contaminant.Type: GrantFiled: February 16, 1993Date of Patent: September 28, 1993Assignee: The Dow Chemical CompanyInventors: Michael L. Chappell, Cameron T. Costain
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Patent number: 5207874Abstract: The purification by distillation of glycidyl (meth)acrylate containing light products containing epichlorohydrin and light impurities, and heavy impurities comprises: in a first stage, a distillation of the glycidyl (meth)acrylate to be purified is conducted in the presence of a first solvent, e.g., water, capable of forming a low boiling point heteroazeotrope with the light impurities and epichlorohydrin, so as to obtain a head fraction which consists essentially of a solvent-light products heteroazeotrope; and, in a second stage, the glycidyl (meth)acrylate thus freed from the light products is subjected to a distillation in the presence of a second solvent, e.g.Type: GrantFiled: June 20, 1991Date of Patent: May 4, 1993Assignee: AtochemInventors: Raymond Hess, Christian Lacroix
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Patent number: 5169964Abstract: The present invention relates to a process for preparing ultrapure epichlorohydrin from epichlorohydrin containing technical impurities, by fractional distillation under particular conditions, preferably with continuous operation, that yield a product of very high purity and very low content of halogenated hydrocarbons. Epoxy resins made with such ultrapure epichlorohydrin are especially well suited for use in fabricating electrical components and microchips.Type: GrantFiled: April 4, 1989Date of Patent: December 8, 1992Assignee: Deutsche Solvay-Werke GmbHInventors: Gerald Jakobson, Werner Siemanowski
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Patent number: 5160587Abstract: An extractive distillation agent consisting essentially of dipropylene glycol is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the dipropylene glycol, water and acetone and some of the methanol introduced into the distillation column.Type: GrantFiled: November 1, 1991Date of Patent: November 3, 1992Assignee: Texaco Chemical CompanyInventors: Edward T. Marquis, George P. Speranza, Yu-Hwa E. Sheu, William K. Culbreth, III, David G. Pottratz
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Patent number: 5154804Abstract: An extractive distillation agent consisting essentially of a monohydroxy alkoxyalkanol containing 5 to 8 carbon atoms is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide, and a heavier bottoms distillation fraction containing substantially all of the monohydroxy alkoxyalkanol and water introduced into the distillation column.Type: GrantFiled: November 1, 1991Date of Patent: October 13, 1992Assignee: Texaco Chemical CompanyInventors: Edward T. Marquis, George P. Speranza, Yu-Hwa E. Sheu, William K. Culbreth, III, David G. Pottratz
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Patent number: 5154803Abstract: An extractive distillation agent consisting essentially of 2-methyl-2,4-pentanediol is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the 2-methyl-2,4-pentanediol, water and acetone and some of the methanol introduced into the distillation column.Type: GrantFiled: November 1, 1991Date of Patent: October 13, 1992Assignee: Texaco Chemical CompanyInventors: Edward T. Marquis, George P. Speranza, Yu-Hwa E. Sheu, William K. Culbreth, III, David G. Pottratz