Purification Or Recovery Patents (Class 568/621)
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Patent number: 6734151Abstract: A process for efficiently producing a high purity compound having oxygen which has a high volume specific resistance and a lubricating oil comprising the high purity compound having oxygen are provided. The process for producing a high purity compound having oxygen selected from a group consisting of high purity polyvinyl ether compounds, high purity polyalkylene glycol compounds, high purity polyol ester compounds, high purity cyclic polyether compounds and high purity carbonate compounds comprises a step of treating with an adsorbent at least one crude compound having oxygen selected from a group consisting of crude polyvinyl ether compounds, crude polyalkylene glycol compounds, crude polyol ester compounds, crude cyclic polyether compounds and crude carbonate compounds. The lubricating oil comprises the high purity compound having oxygen obtained in accordance with this process.Type: GrantFiled: March 11, 2002Date of Patent: May 11, 2004Assignees: Idemitsu Kosan Co., Ltd., Kyowa Yuka Co., Ltd.Inventors: Minoyuki Kubota, Kazuhiko Suzuki, Hirotaka Yamazaki, Tokuyuki Yoshimoto, Akihisa Ogawa, Shigeru Kamimori
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Patent number: 6670406Abstract: The present invention relates to a process for the production of a polyether polyol by polyaddition of an alkylene oxide onto a starter compound containing active hydrogen atoms conducted in the presence of a double metal cyanide catalyst comprising conducting a reaction mixture at least once through a zone which has an energy density of at least 5×106 J/m3, wherein the dwell time of the reaction mixture in this zone is at least 10−6 seconds per pass.Type: GrantFiled: February 19, 2002Date of Patent: December 30, 2003Assignees: Bayer Aktiengesellschaft, Bayer Polymers LLCInventors: Jörg Hofmann, Stephan Ehlers, Bernd Klinksiek, Bert Klesczewski, Christian Steinlein, Lars Obendorf, Harald Pielartzik, Jose F. Pazos
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Patent number: 6620976Abstract: Polyethylene glycol for use in fields with application to a living body wherein the sum of the contents of ethylene glycol and diethylene glycol in the polyethylene glycol is less than or equal to that expressed in the following formula [I]: Sum ⁢ ⁢ of ⁢ ⁢ ethylene ⁢ ⁢ glycol ⁢ ⁢ and ⁢ ⁢ diethylene ⁢ ⁢ glycol ⁢ ⁢ contents ⁢Type: GrantFiled: March 27, 2002Date of Patent: September 16, 2003Assignee: NOF CorporationInventors: Kenji Sakanoue, Kouzoh Sanchika, Tohru Yasukohchi
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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: 6504062Abstract: A process for the preparation of odor-lean polyether polyols from polyether polyol product stream obtained by reacting a starting compound having a plurality of active hydrogen atoms with one or more alkylene oxides, which process comprises the steps of: (a) contacting the polyether polyol product with an excess of acid having a pKa of less than 5 under hydrolysis conditions, (b) contacting the reaction mixture with excessive amount of water to form a two-phase system under hydrolysis conditions by adding an amount of water to form an organic phase and a water phase to reduce the amount of cyclic-ether compounds present in the polyether polyol product, and (c) recovering the odor-lean polyether polyol.Type: GrantFiled: September 6, 2000Date of Patent: January 7, 2003Assignee: Shell Oil CompanyInventors: Henricus Maria Johannes Brons, Hans De Vos
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Publication number: 20020183560Abstract: Process for the preparation of odour-lean polyether polyols from a polyether polyol starting product which is obtained by reacting a starting compound having a plurality of active hydrogen atoms with one or more alkylene oxides, which process comprises the steps of: (a) contacting the neutralised or unneutralised polyether polyol product with an excess of an acid having a pKa of less than 5 under hydrolysis conditions, (b) contacting the reaction mixture with water under hydrolysis conditions, and (c) recovering the odour-lean polyether polyol.Type: ApplicationFiled: September 6, 2000Publication date: December 5, 2002Inventors: Henricus Maria Johannes Brons, Hans De Vos
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Patent number: 6486354Abstract: Embodiments of the present invention generally relate to carrying out organic chemistry on solid supports comprising derivatised functionalities, methods for synthesizing said supports, methods for synthesizing compounds comprising amine groups or N-containing heterocycles using said solid supports, intermediate compounds linked to said supports and uses thereof.Type: GrantFiled: April 17, 2000Date of Patent: November 26, 2002Assignee: Akzo Nobel N.V.Inventors: David Gani, Friedrich Erich Karl Kroll, Michael John Plater, John Richard Morphy, David Rees
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Publication number: 20020137973Abstract: A process for the purification or fractionation of aqueous soluble polymers using an aqueous two-phase system is described. The concentrations of the polymer to be fractionated and of an aqueous soluble salt, and the temperature of the aqueous fractionation medium are adjusted so that two phases form, the lower molecular weight polymer molecules partition into the high salt concentration phase, and the higher molecular weight polymer molecules partition into the low salt concentration phase. The resulting high molecular weight polymers are characterized by a higher average molecular weight and a narrower molecular weight distribution and decreased unsaturation than the unfractionated polymers. After being subjected to the fractionation process, polyol polymers that form hydrogels in aqueous solution exhibited higher viscosities and a liquid to gel transition over a narrower temperature range than the unfractionated polyol polymers.Type: ApplicationFiled: August 13, 2001Publication date: September 26, 2002Inventors: Lorraine E. Reeve, Michael G. Hinsberg
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Patent number: 6455639Abstract: An oxirane derivative and process for preparation of the same, having a high purity characterized in terms of gel permeation chromatography and thin layer chromatography. The oxirane derivative is useful as a starting material for medical purposes, and mainly drug delivery systems.Type: GrantFiled: August 19, 1999Date of Patent: September 24, 2002Assignee: NOF CorporationInventors: Tohru Yasukohchi, Kouzoh Sanchika, Chika Itoh, Kei-ichi Maruyama
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Patent number: 6448371Abstract: A novel process for the purification of poloxamers which contain aldehyde impurities, and particularly for the purification of the poloxamers named poloxamer 188 and poloxamer 407, which process includes dissolving the poloxamer(s) in a solvent which solvent may optionally contain an acid or a mixture of acids; if the solvent in which the poloxamer(s) has been dissolved is free from acid, acid is added; whereafter the aldehydes are removed.Type: GrantFiled: September 8, 2000Date of Patent: September 10, 2002Assignee: Maillefer Instruments Trading S.a.r.l.Inventors: Mats Berg, Alf Djurle, Magnus Melin, Peter Nyman
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Patent number: 6444858Abstract: The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide. The result is an alkoxylated product containing less flocculant.Type: GrantFiled: April 19, 1999Date of Patent: September 3, 2002Assignee: Baker Hughes IncorporatedInventor: Philip Leung
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Patent number: 6437195Abstract: A particularly useful process which includes the steps of providing a feedstream comprising methanol, a soluble condensation promoting component capable of activating a heterogeneous acidic catalyst and a source of formaldehyde formed by conversion of methanol in the presence of a catalyst comprising copper and zinc, and heating this feedstream with the heterogeneous acidic catalyst in a catalytic distillation column to convert methanol and formaldehyde present to methylal and higher polyoxymethylene dimethyl ethers and to separate the methylal from the higher polyoxymethylene dimethyl ethers is disclosed. Advantageously, methylal and higher polyoxymethylene dimethyl ethers are formed and separated in a catalytic distillation column. By including within the column a section containing an anion exchange resin, an essentially acid-free product is obtained.Type: GrantFiled: July 11, 2001Date of Patent: August 20, 2002Assignee: BP Corporation North America Inc.Inventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6410676Abstract: The object is to provide a method for producing a polyoxyalkylene polyol and a method for producing a derivative thereof wherein the remaining catalyst compound is efficiently removed from a crude polyoxyalkylene polyol by a simple manner, and a method for producing a polyoxyalkylene polyol wherein a crude polyoxyalkylene polyol is produced by addition polymerization of an epoxide compound to an active hydrogen compound using as a catalyst a compound having a P═N bond, then, the crude polyoxyalkylene polyol is allowed to contact with a solid acid having a specific surface area of 450 to 1200 m2/g and an average pore diameter of 40 to 100 Å to control the catalyst-remaining amount in the polyoxyalkylene polyol to 150 ppm or less, and a method for producing a derivative of the-above-described polyol are provided.Type: GrantFiled: May 30, 2000Date of Patent: June 25, 2002Assignee: Mitsui chemicals, Inc.Inventors: Satoshi Yamasaki, Yasunori Hara, Tamotsu Kunihiro, Fumio Yamazaki, Mikio Matsufuji, Ariko Nishikawa, Shinsuke Matsumoto, Tsukuru Izukawa, Masahiro Isobe, Kazuhiko Ohkubo, Kaoru Ueno
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Patent number: 6403842Abstract: Disclosed are a process for producing a poly(alkylene ether) glycol which comprises polymerizing a cyclic ether in the presence of at least a catalyst and a carboxylic acid anhydride, wherein the carboxylic acid anhydride has a ketene dimer content of 50 ppm or lower, and a process for producing a poly(alkylene ether) glycol which comprises polymerizing a cyclic ether in the presence of at least a catalyst and acetic anhydride, wherein the acetic anhydride is purified acetic anhydride obtained by treating acetic anhydride by contacting with at least one of a metal oxide and a mixed oxide, and optionally, distilling the acetic anhydride simultaneously with or after the contact treatment.Type: GrantFiled: January 13, 2000Date of Patent: June 11, 2002Assignee: Mitsubishi Chemical CorporationInventors: Mitsuharu Kobayashi, Nobuyuki Murai
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Patent number: 6392102Abstract: A particularly useful process which includes the steps of providing a feedstream comprising providing a source of formaldehyde formed by conversion of dimethyl ether in the presence of a catalyst comprising tungsten oxide; and (i) heating the feedstream with the heterogeneous acidic catalyst in a catalytic distillation column to convert methanol and formaldehyde present to methylal and higher polyoxymethylene dimethyl ethers and to separate the methylal from the higher polyoxymethylene dimethyl ethers is disclosed, and/or (ii) contacting the source of formaldehyde and a predominately dimethyl ether feedstream with a heterogeneous, condensation promoting catalyst capable of hydrating dimethyl ether under conditions of reaction sufficient to form an effluent comprising water, methanol, formaldehyde, dimethyl ether, and polyoxymethylene dimethyl ethers is disclosed. Unreacted dimethyl ether is recovered from the effluent and recycled to the formation of polyoxymethylene dimethyl ethers.Type: GrantFiled: April 12, 2000Date of Patent: May 21, 2002Assignee: BP Corporation North America Inc.Inventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6384216Abstract: A process for purifying alkenyl compounds having a divalent or trivalent heteroatom in the &agr;-position relative to the double bond by distillation comprises carrying out at least two distillations in which the purified alkenyl compounds are obtained from the gas phase by condensation, where the time between the first distillation after the synthesis of the alkenyl compounds and at least one further distillation is at least one day and the purified alkenyl compounds have an APHA color number of <30.Type: GrantFiled: August 9, 2001Date of Patent: May 7, 2002Assignee: BASF AktiengesellschaftInventors: Rudolf Erich Lorenz, Arnd Böttcher, Rolf Pinkos
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Patent number: 6372923Abstract: The present invention provides a process for preparing an alcohol derivative, where the alcohol derivative is an ester, acetal, ketal, ether glycoside, or alkyl glycoside, by reacting an alcohol with a carbonyl compound, alcohol, olefin, epoxy compound or saccharide, where C2-4 vicinal alkylene oxides are excluded, in the presence of (A) an aluminum alkoxide and (B) sulfuric acid or phosphoric acid.Type: GrantFiled: May 31, 2000Date of Patent: April 16, 2002Assignee: Kao CorporationInventors: Mitsuru Uno, Munehisa Okutsu, Tomohito Kitsuki
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Patent number: 6362126Abstract: Double-metal cyanide catalysts of the formula M1a[M2(CN)b(A)c]d. fM1gXn. h (H2O).Type: GrantFiled: September 9, 2000Date of Patent: March 26, 2002Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Harald Larbig, Reinhard Lorenz, Dieter Junge, Ulrich Kammel
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Patent number: 6350919Abstract: Oxygenated organic compounds exhibiting the desired combination of advantageous properties have structures represented by the formula CH3 E (CH2O)x (CHO)y E′ where E is selected from the group consisting of CH3O— and CH3CH2O—, E′ is selected from the group consisting of —CH3 and —CH2CH3, x is a number from 0 to about 10, y is number from 0 to about 10 such that the sum (x+y) is at least 2. Economical processes are disclosed for production of a mixture of oxygenated organic compounds which are suitable components for blending into fuel having improved qualities for use in compression ignition internal combustion engines (diesel engines).Type: GrantFiled: April 19, 2000Date of Patent: February 26, 2002Assignee: BP Corporation North America Inc.Inventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6350920Abstract: Polyether polyols can be prepared by reacting polyols with epoxides in the presence of basic catalysts, by treating the polyether polyols containing the basic catalysts with OH-functional solid compounds of metals of groups III to VIII of the periodic system of the elements (Mendeleyev), the compounds being insoluble in the polyether polyols and having BET surface areas of from 10 to 1000 m2/g, isolating the solid inorganic compounds laden with the basic catalysts from the polyether polyol and using them in the reaction of polyols with epoxides, or bringing the isolated inorganic compounds laden with the basic catalysts into contact with the polyols that are to be used in the reaction with epoxides, separating those polyols from the inorganic compounds and delivering them to the reaction with epoxides.Type: GrantFiled: March 20, 2000Date of Patent: February 26, 2002Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Manfred Dietrich, Pramod Gupta, Pieter Ooms
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Patent number: 6306263Abstract: A distillation procedure is provided for the separation of impurities from organic materials such as glycols and glycol ethers whereby a liquid stripping component is interfaced into a distillation column with or below the organic material introduction, heat being provided by a reboiler, the stripping component and impurities being removed overhead.Type: GrantFiled: March 31, 1999Date of Patent: October 23, 2001Assignee: Arco Chemical Technology, L.P.Inventor: Vijai P. Gupta
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Patent number: 6211415Abstract: A hexafluoropropylene oxide oligomer of the formula: RfO[CF(CF3)CF2O]nCF(CF3)COF in which Rf is a group represented by the formula: F(CF2)m— in which m is an integer of 1 to 8, or the formula: (CF3)2CF(CF2)q— in which q is an integer of 0 to 6, and n is a number of 3 to 20 is heated and thermally decomposed in a solvent at a temperature of at least 100° C. in the presence of a compound which generates a fluoride (F−) ion to obtain mainly the dimer, trimer and tetramer of hexafluoropropylene oxide. Thus, the valuable low molecular weight oligomers of hexafluoropropylene oxide can be obtained from high molecular weight oligomers of hexafluoropropylene oxide which have been discarded.Type: GrantFiled: May 21, 1999Date of Patent: April 3, 2001Assignee: Daikin Industries, Ltd.Inventors: Shigeru Morita, Toshihiko Amano
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Patent number: 6191315Abstract: Most generally, the invention provides a method for making a neutralized polyether polyol, comprising the steps of a) Polymerizing one or more alkylene oxides in the presence of an alkaline catalyst to form a polyalkylene oxide intermediate; and b) Neutralizing the intermediate, after the polymerization step a) is complete, with an organic acid of general formula where R1 is hydrogen, methyl, or ethyl; R2 is methyl or ethyl; and R3 is an alkyl, aryl, or aralkyl group containing one to twelve carbon atoms. The invention also comprises the novel compositions made by the above process.Type: GrantFiled: February 11, 1999Date of Patent: February 20, 2001Assignee: BASF CorporationInventors: Chacko Thankachan, Brian J. Betke, Michael C. Welch
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Patent number: 6166266Abstract: A particularly useful process which includes the steps of providing a source of formaldehyde formed by conversion of methanol in the presence of a catalyst comprising oxides of molybdenum as an essential catalyst component; and contacting the source of formaldehyde and a predominately dimethyl ether feedstream with a heterogeneous, condensation promoting catalyst capable of hydrating dimethyl ether under conditions of reaction sufficient to form an effluent comprising water, methanol, formaldehyde, dimethyl ether, and polyoxymethylene dimethyl ethers is disclosed. Unreacted dimethyl ether is recovered from the effluent and recycled to the formation of polyoxymethylene dimethyl ethers. The resulting dimethyl ether-free liquid mixture is heated in the presence of an acidic catalyst to convert at least the methanol and formaldehyde present to polyoxymethylene dimethyl ethers. Advantageously, methylal and higher polyoxymethylene dimethyl ethers are formed and separated in a catalytic distillation column.Type: GrantFiled: November 12, 1998Date of Patent: December 26, 2000Assignee: BP Amoco CorporationInventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6160174Abstract: A particularly useful process which includes the steps of providing a source of formaldehyde formed by conversion of methanol in the presence of a catalyst comprising silver as an essential catalyst component; and contacting the source of formaldehyde and a predominately dimethyl ether feedstream with a heterogeneous, condensation promoting catalyst capable of hydrating dimethyl ether under conditions of reaction sufficient to form an effluent comprising water, methanol, formaldehyde, dimethyl ether, and polyoxymethylene dimethyl ethers is disclosed. Unreacted dimethyl ether is recovered from the effluent and recycled to the formation of polyoxymethylene dimethyl ethers. The resulting dimethyl ether-free liquid mixture is heated in the presence of an acidic catalyst to convert at least the methanol and formaldehyde present to polyoxymethylene dimethyl ethers. Advantageously, methylal and higher polyoxymethylene dimethyl ethers are formed and separated in a catalytic distillation column.Type: GrantFiled: November 12, 1998Date of Patent: December 12, 2000Assignee: BP Amoco CorporationInventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6160186Abstract: A particularly useful process which includes the steps of providing a source of formaldehyde formed by conversion of dimethyl ether in the presence of a catalyst comprising copper and zinc; and contacting the source of formaldehyde and a predominately dimethyl ether feedstream with a heterogeneous, condensation promoting catalyst capable of hydrating dimethyl ether under conditions of reaction sufficient to form an effluent comprising water, methanol, formaldehyde, dimethyl ether, and polyoxymethylene dimethyl ethers is disclosed. Unreacted dimethyl ether is recovered from the effluent and recycled to the formation of polyoxymethylene dimethyl ethers. The resulting dimethyl ether-free liquid mixture is heated in the presence of an acidic catalyst to convert at least the methanol and formaldehyde present to polyoxymethylene dimethyl ethers. Advantageously, methylal and higher polyoxymethylene dimethyl ethers are formed and separated in a catalytic distillation column.Type: GrantFiled: November 12, 1998Date of Patent: December 12, 2000Assignee: BP Amoco CorporationInventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6093855Abstract: The divinyl ethers of diethylene glycol or triethylene glycol are separated from the monovinyl ether of the corresponding oligoethylene glycol by distillation, a metal hydroxide being added to the vinyl ether mixture.Type: GrantFiled: September 23, 1998Date of Patent: July 25, 2000Assignee: BASF AktiengesellschaftInventor: Rudolf Erich Lorenz
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Patent number: 6087539Abstract: A process for producing an ether compound represented by the general formula (II) or (III): ##STR1## wherein R.sup.1 and R.sup.2 represent each an alkyl group or a cycloalkyl group and n represents an integer of 1 to 50, which comprises bringing an acetal compound represented by the general formula (I): ##STR2## into reaction with hydrogen in the presence of a solid catalyst comprising (A) nickel in an amount corresponding to 10 to 70% by weight of metallic nickel, and (B) at least one compound selected from the group consisting of oxides of silicon, aluminum, magnesium, titanium, and zirconium; and synthetic or natural inorganic oxides containing one or more of these oxides as the constituents thereof. A vinyl ether polymer having a terminal ether group can be obtained with a good yield without causing corrosion of the apparatus used for the reaction.Type: GrantFiled: October 20, 1997Date of Patent: July 11, 2000Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hirotaka Yamasaki, Akihisa Ogawa, Shigeru Kamimori, Yoshikazu Hirao, Keiji Fujita, Tokuyuki Yoshimoto
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Patent number: 6034281Abstract: The present invention provides a method for purifying diethylene glycol monoethyl ether, which is commonly known as Carbitol.TM. or Ethyl Carbitol.TM.. The method according to the present invention includes combining n-heptanol as an azeotrope-forming agent to crude diethylene glycol monoethyl ether which contains ethylene glycol as an impurity to form a mixture, subjecting the mixture to distillation whereby an overhead product comprising an azeotrope of ethylene glycol and n-heptanol and a bottoms product are produced, and recovering purified diethylene glycol monoethyl ether from the bottoms product. By practicing the method of the present invention, the ethylene gylcol content of diethylene glycol monoethyl ether can be reduced from thousands of parts per million to less than about twenty-five parts per million such that the purified diethylene glycol monoethyl ether is suitable for use as a solvent in pharmaceutical manufacturing applications.Type: GrantFiled: November 24, 1998Date of Patent: March 7, 2000Assignee: Ferro CorporationInventors: Charles R. Egedy, Christian C. Clause
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Patent number: 5962749Abstract: This invention relates to a process for the purification of polyether polyols. This process enables the removal of residual alkaline metal catalyst from produced polyether polyol. It comprises a) adding glycerine to a polyether polyol that contains Group IA alkaline metal catalyst to form a precipitate, and b) separating the precipitate formed in a) to provide a purified polyether polyol. The present invention also relates to the purified polyether polyol produced by this process, the precipitate produced by this process, and the use of the precipitate as an alkaline metal catalyst in a process for the production of polyether polyols.Type: GrantFiled: December 24, 1997Date of Patent: October 5, 1999Assignee: Bayer CorporationInventors: Harold R. Parsons, Donald C. Dunham, Steven L. Schilling, Keith J. Headley
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Patent number: 5962748Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step comprising reacting propylene oxide with an initiator having at least two hydroxyl groups in the presence of a basic catalyst, a second step of contacting the polyether product of the first step having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.Type: GrantFiled: October 23, 1997Date of Patent: October 5, 1999Assignee: Huntsman Petrochemical CorporationInventor: Timothy L. Lambert
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Patent number: 5951829Abstract: A method of separating heteropoly compounds from mixtures of polyethers, polyesters and/or polyether esters, a protic component and heteropoly compounds, wherein the protic component is removed from the mixture and subsequently separating off the heteropoly compound as a separate phase. The polymer phase which remains is preferably brought into further contact with a solid adsorbent that is capable of adsorbing heteropoly compounds.Type: GrantFiled: March 27, 1997Date of Patent: September 14, 1999Assignee: BASF AktiengesellschaftInventors: Hans-Jurgen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Muller
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Patent number: 5912342Abstract: The invention relates to a compound of the formula (I) wherein whereinY is the fraction of a solid or soluble support, where Y may include a residue of a functional group having been attached to said support, said functional group having been hydroxy, amino, thio, epoxy or halogen,R.sup.1 is aryl, heteroaryl, alkyl chain or ring or ring system, which may include a heteroatom, or R.sup.1 is nothing, and R.sup.2 is vinyl;CH.sub.2 CH.sub.2 X, where X is halogen; orR.sup.3 C.dbd.CHR or R.sup.3 CH--CH.sub.2 R.sup.4 X, where R.sup.3 and R.sup.4 are the same or different and are alkyl, acyl, carbonyl, cyano or nitro groups and X is halogen.The invention also relates to a method for preparation of compound (I) and to its use as a substrate in the synthesis of tertiary amines. The invention still concerns a group of alpha-2-receptor active tetrahydroisoquinoline derivatives.Type: GrantFiled: August 12, 1997Date of Patent: June 15, 1999Inventors: Petri Heinonen, Harri Lonnberg, Victor Cockcroft
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Patent number: 5910614Abstract: Separation process of bifunctional macromolecules having hydroxylic termination from non functional and/or monofunctional macromolecules having hydroxylic termination contained in admixture in perfluoropolyoxyalkylenes (I) comprising the following phases:addition of the macromer (I) to a suspension of stationary phase in polar solvent, said stationary phase being formed by a compound containing sites and/or active groups, capable of establishing bonds or interactions of polar type, or hydrogen bonds, with the hydroxylic terminals of the perfluoropolyoxyalkylenes contained in the mixture of formula (I), the macromer/stationary phase ratio ranging from 2/3 to 1/1 w/w; solvent/(stationary phase+macromer) ratio ranging from 0.8/1 to 1.Type: GrantFiled: July 30, 1997Date of Patent: June 8, 1999Assignee: Ausimont S.p.A.Inventors: Stefano Turri, Claudio Tonelli, Carlo Pogliani
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Patent number: 5852218Abstract: A method for converting the diester of a polyether polyol (e.g., the diacetate ester of polytetramethylene ether, PTMEA) to a corresponding dihydroxy polyether polyol (e.g., polytetramethylene ether glycol, PTMEG) involving reactive distillation wherein a diester of polyether polyol is fed to the top portion of the column along with an effective amount of at least one alkali metal oxide or alkaline earth metal oxide, hydroxide or alkoxide catalyst (e.g., sodium methoxide) and with a C.sub.1 to C.sub.4 alkanol (e.g., methanol) while simultaneously adding to the bottom of the reactive distillation column hot alkanol vapor to sweep any alkanol ester formed by alkanolysis of the diester of polyether polyol upwardly. Such a process is useful for achieving high levels of conversion PTMEA to PTMEG on a commercial scale with the overhead from the column being amenable to azeotropic separation of the methyl acetate and recycle of the methanol.Type: GrantFiled: December 14, 1995Date of Patent: December 22, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Suriyanarayan Dorai
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Patent number: 5800711Abstract: A process for the fractionation of polyoxyalkylene block copolymers wherein the polydispersity of the polyether is reduced. The fractionation process, which removes lower molecular weight species such as polyoxyalkylene homopolymer, truncated polyoxyalkylene diblock polymers, or other reaction byproducts, comprises salt extraction and liquid phase separation to provide a product with a narrower molecular weight distribution, lower degree of unsaturation, and distinctly different physical characteristics compared to the starting material.Type: GrantFiled: October 18, 1996Date of Patent: September 1, 1998Assignee: MDV Technologies, Inc.Inventors: Lorraine E. Reeve, Michael G. Hinsberg
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Patent number: 5767324Abstract: Process for reducing the level of unsaturation in a polyether polyol having an oxypropylene content of at least 30% by weight calculated on the total amount of oxyalkylene units in the polyol and having a number average equivalent weight of at least 1000 by subjecting the polyol to ultrafiltration.Type: GrantFiled: November 6, 1996Date of Patent: June 16, 1998Assignee: Imperial Chemical Industries PLCInventors: Pierre Gilbert Henri Jean Chaffanjon, Minh Son Le, Robert Henry Carr, Howard Matthew Colquhoun, Jan Frans Hernalsteen, Julien Armand Devos
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Patent number: 5767323Abstract: Substantially transition metal-free polyoxyalkylene polyethers may be prepared by double metal cyanide complex-catalyzed oxyalkylation of a suitable hydric oxyalkylation initiator molecule by employing 15 ppm or less of a double metal cyanide complex oxyalkylation catalyst having a propylene oxide polymerization rate greater than 5 g propylene oxide/minute. The induction periods associated with oxyalkylation employing double metal cyanide complex catalysts may be reduced by preparing preactivated master batches and by increasing the oxyalkylation reactor temperature during at least the induction period.Type: GrantFiled: December 22, 1995Date of Patent: June 16, 1998Assignee: ARCO Chemical Technology, L.P.Inventors: Yiannakis Televantos, Bi Le-Khac
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Patent number: 5739208Abstract: A poly(ethylene glycol) derivative is disclosed that is activated with a sulfone moiety for selective attachment to thiol moieties on molecules and surfaces. The activated PEG is water soluble, hydrolytically stable for extended periods, and forms hydrolytically stable linkages with thiol moieties. The linkages generally are not reversible in reducing environments. The PEG derivative is useful for modifying the characteristics of substances including modifying biologically active molecules and surfaces for biocompatibility. Methods for synthesizing the active PEG and for preparing conjugates of the active PEG and other substances, including biologically active substances, are also disclosed.Type: GrantFiled: June 7, 1995Date of Patent: April 14, 1998Assignee: Shearwater Polymers, Inc.Inventor: J. Milton Harris
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Patent number: 5714523Abstract: Process for alcoholizing and hydrolysing a flexible polyurethane foam by bringing a flexible polyurethane foam in contact with an alcoholizing polyol, allowing the foam and the polyol to react in the presence of a catalyst which enhances alcoholysis and hydrolysis of the foam in an amount of 0.001 to 0.25 and preferably 0.001 to 0.08% by weight based on the weight of the foam, then allowing the mixture to separate in an upper phase and a lower phase and collecting these phases in separate containers, wherein the hydrolysis is conducted by adding water and allowing the mixture to react with the water after the foam has been combined with the polyol and before the mixture is allowed to separate.Type: GrantFiled: January 21, 1997Date of Patent: February 3, 1998Assignee: Imperial Chemical Industries PLCInventors: Julian Francis George Hopper, Patrick Margriet Gaston Goegebeur, Harry Kooren
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Patent number: 5698746Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step of contacting a polyether having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.Type: GrantFiled: November 4, 1996Date of Patent: December 16, 1997Assignee: Huntsman Petrochemical CorporationInventor: Timothy L. Lambert
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Patent number: 5689012Abstract: A continuous process for the preparation of polyoxyalkylene polyethers using DMC catalysts as the polyoxyalkylation catalyst employs continuous addition of alkylene oxide in conjunction with continuous addition of starter and catalyst to a continuous oxyalkylation reactor. Despite the continuous introduction of starter, the molecular weight distribution of the polyether product is quite narrow, as indicated by the exceptionally low polydispersity of the product. The presence of low molecular weight species during the majority of the polyoxyalkylation also substantially eliminates extremely high molecular weight fractions having molecular weights greater than 100,000 Da, again without appreciably broadening molecular weight distribution. By withdrawing intermediate molecular weight polyether product or diverting a portion of the end product to prepare a catalyst/starter mixture, rapid and sustained reaction rates can be achieved while employing low molecular weight starters.Type: GrantFiled: July 18, 1996Date of Patent: November 18, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Jose F. Pazos, T. Thomas Shih
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Patent number: 5672768Abstract: Low-odor, higher molecular weight polyether polyols are produced by purifying the polyether polyols at temperatures of 110.degree. to 150.degree. C. and pressures of 10 to 70 hPa with the addition of 5 to 30% by weight of water, wherein the water is passed in finely divided form, with a droplet diameter of about 5 to 100.mu., through the polyether polyols to be purified for a time of metered addition of 1 to 5 hours.Type: GrantFiled: January 8, 1997Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Pramod Gupta, Gundolf Jacobs, Joel Leuridan
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Patent number: 5648557Abstract: Cyclic ethers are polymerized or copolymerized in homogeneous liquid phase using very low concentrations of heteropolyacid catalyst to produce essentially linear polyoxyalkylene polymers. The product of the polymerization contains less than 2 weight percent cyclic oligomer by-product and has a molecular weight distribution (M.sub.w /M.sub.n) between 1 and 2. Alcohols, acyl-containing compounds and alkalies can be used as end-caping groups to terminate polymerization or modify the properties of the polymer produced. The process produces novel polyoxyalkylene copolymers and block copolymers that are useful as lubricants. The copolymers have a high viscosity index and are compatible with mineral oil and synthetic hydrocarbon lubricants. Preferred comonomers are tetrahydrofuran, C.sub.2 -C.sub.20 monoepoxides and oxetan.Type: GrantFiled: October 27, 1994Date of Patent: July 15, 1997Assignee: Mobil Oil CorporationInventor: Liwen Wei
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Patent number: 5630914Abstract: A method for decontaminating a liquid of a contaminant having a vapor pressure which is higher than the vapor pressure of the liquid. A contaminated liquid is directed through an inclined conduit. A gas is directed into the inclined conduit, whereby the gas contacts the liquid and transports the contaminant, which has volatilized in the inclined conduit, out of the inclined conduit, thereby decontaminating the liquid. The liquid is discharged from the inclined conduit.Type: GrantFiled: June 7, 1995Date of Patent: May 20, 1997Assignee: Pharm-Eco Laboratories, Inc.Inventors: Yesh P. Sachdeva, Richard L. Gabriel
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Patent number: 5585458Abstract: A method for preparing polyether glycol is disclosed. An ester end-capped polyalkylene ether and an alcohol are subjected to alcoholysis at a temperature of 35.degree.-150.degree. C. and a pressure of 1-10 atm in the presence of a mixed metal oxide as a catalyst. The mixed metal oxide includes an alkaline earth metal oxide and at least one component selected from alumina, silica, and zinc oxide.Type: GrantFiled: June 27, 1995Date of Patent: December 17, 1996Assignee: Industrial Technology Research InstituteInventors: Wen-Fa Lin, Yu-Wen Chen, Jih-Chen Huang, Hsueh-Ying Chen
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Patent number: 5562808Abstract: A method and apparatus are disclosed for decontaminating a liquid surfactant of a dioxane having a vapor pressure which is higher than the surfactant. A contaminated liquid surfactant is directed through an inclined conduit. A gas is directed into the inclined conduit, whereby the gas contacts the surfactant and transports the dioxane contaminant, which has volatilized in the inclined conduit, out of the inclined conduit, thereby decontaminating the surfactant. The liquid surfactant is discharged from the inclined conduit.Type: GrantFiled: September 21, 1993Date of Patent: October 8, 1996Assignee: Pharm-Eco Laboratories, Inc.Inventors: Yesh P. Sachdeva, Richard L. Gabriel
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Patent number: 5545712Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered, alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 23, 1995Date of Patent: August 13, 1996Assignee: Mitsu Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5468840Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered. alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 29, 1994Date of Patent: November 21, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5449841Abstract: A process for reducing the level of metal ions and/or metal compounds in a polyoxyalkylene monool or polyol having a number average molecular weight of above 500-25000 by bringing the monool or polyol into contact with an extracting compound which is a polyol or a polyol mixture having a number average molecular weight of at most 500 and being immiscible with the polyoxyalkylene monool or polyol, mixing the extracting compound and the polyoxyalkylene monool or polyol, allowing the extracting compound and the polyoxyalkylene monool or polyol to separate and removing the extracting compound.Type: GrantFiled: October 12, 1994Date of Patent: September 12, 1995Assignee: Imperial Chemical Industries PLCInventor: Patrick M. G. Goegebeur