Two Identical Or Diverse Alkyl Groups Bonded Directly To The -o-c(=o)o- Group (e.g., Dimethyl Carbonate, Methyl Ethyl Carbonate, Etc.) Patents (Class 558/277)
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Publication number: 20030236428Abstract: A method of preparing a dialkyl carbonate includes reacting an alkanol, oxygen, carbon monoxide, and a catalyst to form a mixture that includes a dialkyl carbonate and an alkyl chloroformate. The mixture is separated into a liquid fraction and a gaseous fraction, and alkyl chloroformate is removed from the gaseous fraction. Also described is an apparatus for carrying out the method. The method is particularly useful for preventing corrosion in a cold wash unit that removes further organic impurities from the gaseous fraction.Type: ApplicationFiled: June 2, 2003Publication date: December 25, 2003Applicant: GENERAL ELECTRIC COMPANYInventors: Jan van de Broek, Stephan Bouwens, Maarten Campman, Daniel Favre, Cornelis Adrianus Maria van Gool, Leon Kalle, George P. Moloney
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Patent number: 6620958Abstract: A method for separating at least one lower polarity fluid from a mixture of fluids having varying polarity, comprising contacting at least one low polarity or non-polar polymeric membrane with the mixture of fluids under conditions such that the at least one lower polarity fluid selectively permeates through the membrane, wherein the membrane is one which has a ratio of heteroatoms chemically bonded to the carbon atoms in the membrane to the number of carbon atoms of less than about 0.2, preferably less than about 0.05.Type: GrantFiled: June 26, 2001Date of Patent: September 16, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: J. Scott Buchanan, Lawrence J. Altman, John W. Diehl
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Patent number: 6620959Abstract: A process for the production of a dialkyl carbonate and a diol, such as dimethyl carbonate and ethylene glycol, by reacting a feed containing a cyclic carbonate, a hydroxy alkyl carbonate and an aliphatic monohydric alcohol in the presence of a transesterification catalyst is described. In another aspect, a process is described which is particularly useful for producing unsymmetric dialkyl carbonates, such as ethyl methyl carbonate.Type: GrantFiled: April 16, 2002Date of Patent: September 16, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jose Guadalupe Santiesteban, William A. Weber
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Publication number: 20030153782Abstract: Unexpected corrosion of downstream sections of a dialkyl carbonate manufacturing apparatus has been traced to alkyl chloroformate impurities, which slowly decompose to yield hydrochloric acid. An improved process and apparatus for dialkyl carbonate synthesis reduce corrosion by physically removing or chemically decomposing the alkyl chloroformate impurities within the corrosion-resistant upstream sections of the apparatus. The alkyl chloroformate may be decomposed by passing it through a passageway at a temperature of about 30° C. to about 130° C. for a time of about 0.5 hour to about 10 hours. The passageway may include one or more holding vessels or a tubular section that promotes plug flow.Type: ApplicationFiled: August 23, 2002Publication date: August 14, 2003Inventors: Eugene Pauling Boden, Ganesh Kailasam, Larry Neil Lewis, Alberto Nisoli, John Yaw Ofori, Angel Sanchez Gonzalez, Ignacio Vic Fernandez
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Patent number: 6600061Abstract: The present invention provides a method for making aromatic carbonates. In this method, an aryl alcohol is reacted with a dialkyl carbonate in a reactor (e.g., a distillation column) to produce an arylalkyl carbonate and diaryl carbonate. The total yield of arylalkyl carbonate and diaryl carbonate together is at least 40%. Also, the selectivity of diaryl carbonate versus diaryl carbonate and arylalkyl carbonate together is preferably at least 25%.Type: GrantFiled: November 15, 2000Date of Patent: July 29, 2003Assignee: General Electric CompanyInventors: Stephan Mathys Bouwens, Marcel Vieveen
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Patent number: 6596895Abstract: The present invention provides a method for making polycarbonates. One embodiment of the method comprises reacting diphenylcarbonate with a dihydric phenol. The diphenylcarbonate is made by reacting a reaction mixture comprising aryl alcohol together with a dialkyl carbonate in a reactor to produce aryl alkylcarbonate and diaryl carbonate.Type: GrantFiled: February 21, 2002Date of Patent: July 22, 2003Assignee: General Electric CompanyInventors: Stephan Mathys Bouwens, Marcel Vieveen
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Publication number: 20030105346Abstract: Aromatic carbonates can be prepared economically and efficiently by reacting an aromatic hydroxy compound with carbon monoxide and oxygen in the presence of a catalyst wherein a palladium compound is supported on a perovskite-type composite oxide represented by the following formula (1) or (1′):Type: ApplicationFiled: December 10, 2002Publication date: June 5, 2003Applicant: TEIJIN LIMITEDInventor: Eishin Yoshisato
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Patent number: 6573396Abstract: A process for the production of a dialkyl carbonate and a diol from a cyclic carbonate and an aliphatic monohydric alcohol wherein the cyclic carbonate and aliphatic monohydric alcohol are reacted in the presence of a transesterification catalyst to form a crude product stream which contains a dialkyl carbonate, a diol, a hydroxy alkyl carbonate, which is formed as an intermediate of the two step transesterification reaction, unreacted aliphatic monohydric alcohol and unreacted cyclic carbonate. The dialkyl carbonate and unreacted aliphatic monohydric alcohol are separated from the crude product stream and then the hydroxy alkyl carbonate is diminished, reduced or eliminated from the crude product stream, prior to the separation and purification steps needed to recover the diol, resulting in improved yields and product purity.Type: GrantFiled: October 12, 2001Date of Patent: June 3, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: J. Scott Buchanan, Jose G. Santiesteban, Zhaozhong Jiang
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Publication number: 20030097016Abstract: A method for the catalytic conversion of organic carbonate, wherein organic carbonate is contacted with alcohol and/or water in the presence of a lanthanum catalyst comprising at least about 7 wt. % of lanthanum supported on a support.Type: ApplicationFiled: November 12, 2002Publication date: May 22, 2003Inventors: Johannes Petrus De Jonge, Jean-Paul Lange, Ingrid Maria Van Vegchel
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Publication number: 20030078448Abstract: A process for the production of a dialkyl carbonate and a diol from a cyclic carbonate and an aliphatic monohydric alcohol wherein the cyclic carbonate and aliphatic monohydric alcohol are reacted in the presence of a transesterification catalyst to form a crude product stream which contains a dialkyl carbonate, a diol, a hydroxy alkyl carbonate, which is formed as an intermediate of the two step transesterification reaction, unreacted aliphatic monohydric alcohol and unreacted cyclic carbonate. The dialkyl carbonate and unreacted aliphatic monohydric alcohol are separated from the crude product stream and then the hydroxy alkyl carbonate is diminished, reduced or eliminated from the crude product stream, prior to the separation and purification steps needed to recover the diol, resulting in improved yields and product purity.Type: ApplicationFiled: October 12, 2001Publication date: April 24, 2003Inventors: J. Scott Buchanan, Jose G. Santiesteban, Zhaozhong Jiang
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Publication number: 20030060650Abstract: Unexpected corrosion of downstream sections of a dialkyl carbonate manufacturing apparatus has been traced to alkyl chloroformate impurities, which slowly decompose to yield hydrochloric acid. An improved process and apparatus for dialkyl carbonate synthesis reduce corrosion by physically removing or chemically decomposing the alkyl chloroformate impurities within the corrosion-resistant upstream sections of the apparatus.Type: ApplicationFiled: August 14, 2001Publication date: March 27, 2003Inventors: Eugene Pauling Boden, Ganesh Kailasam, Larry Neil Lewis, Alberto Nisoli, John Yaw Ofori, Angel Sanchez Gonzalez, Ignacio Vic Fernandez
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Publication number: 20030045739Abstract: An integrated process for the production of a dialkyl carbonate and a diol from an alkylene oxide, carbon dioxide and an aliphatic monohydric alcohol is described in which an alkylene oxide is first reacted with carbon dioxide in the presence of a homogeneous carbonation catalyst to provide a corresponding cyclic carbonate and the cyclic carbonate is then reacted with an aliphatic monohydric alcohol in the presence of the homogeneous carbonation catalyst and/or a heterogeneous transesterification catalyst and recycling the homogeneous carbonation catalyst to provide a corresponding dialkyl carbonate and diol.Type: ApplicationFiled: June 22, 2001Publication date: March 6, 2003Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jose G. Santiesteban, William A. Weber
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Publication number: 20030028044Abstract: A method for separating at least one lower polarity fluid from a mixture of fluids having varying polarity, comprising contacting at least one low polarity or non-polar polymeric membrane with the mixture of fluids under conditions such that the at least one lower polarity fluid selectively permeates through the membrane, wherein the membrane is one which has a ratio of heteroatoms chemically bonded to the carbon atoms in the membrane to the number of carbon atoms of less than about 0.2, preferably less than about 0.05.Type: ApplicationFiled: June 26, 2001Publication date: February 6, 2003Inventors: J. Scott Buchanan, Lawrence J. Altman, John W. Diehl
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Publication number: 20030023109Abstract: An integrated process for the production of a dialkyl carbonate and a diol from an alkylene oxide, carbon dioxide and an aliphatic monohydric alcohol is described in which an alkylene oxide is first reacted with carbon dioxide in the presence of a halogen-free carbonation catalyst to provide a corresponding cyclic carbonate and the cyclic carbonate is then reacted with an aliphatic monohydric alcohol in the presence of the carbonation catalyst and/or a transesterification catalyst and recycling the carbonation catalyst to provide a corresponding dialkyl carbonate and diol, wherein the dialkyl carbonate product exhibits a halogen concentration of about 5 ppm or less.Type: ApplicationFiled: March 25, 2002Publication date: January 30, 2003Inventors: Richard H. Schlosberg, J. Scott Buchanan, Jose Guadalupe Santiesteban, Zhaozhong Jiang, William A. Weber
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Patent number: 6479689Abstract: A method for continuously producing a dialkyl carbonate and a diol, comprising: (1) continuously feeding a cyclic carbonate and an aliphatic monohydric alcohol to a continuous multi-stage distillation column, and continuously effecting a transesterification between the cyclic carbonate and the aliphatic monohydric alcohol in the presence of a transesterification catalyst in the distillation column, while continuously withdrawing a low boiling point mixture in a gaseous form containing the produced dialkyl carbonate and the unreacted aliphatic monohydric alcohol from an upper portion of the distillation column and continuously withdrawing a high boiling point mixture in a liquid form containing the produced diol and the unreacted cyclic carbonate from a lower portion of the distillation column, and (2) continuously feeding the high boiling point mixture withdrawn from the lower portion of the distillation column to a continuous etherification reactor, to thereby effect a continuous etherification reaction betwType: GrantFiled: June 11, 2001Date of Patent: November 12, 2002Assignee: Asahi Kasei Kabushiki KaishaInventors: Masahiro Tojo, Kazuhiro Oonishi
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Patent number: 6469071Abstract: Polyester based polycarbonate (meth)acrylates prepared by the reaction of a alkylene or arylene diol polycarbonate with an anhydride or its dicarboxylic acid to form a carboxyl terminated diester, reacting the diester with a diglycidyl ether and an acrylic or methacrylic acid to form an acrylate terminate polymer which is useful for radiation cured coatings which have superior adhesion and reverse impact strength when applied to plastic substrates.Type: GrantFiled: April 13, 2001Date of Patent: October 22, 2002Assignee: Sartomer Technology Company, Inc.Inventors: Mingxin Fan, Gary Ceska, James Horgan, Robert Adams, William Schaeffer, Josh Oliver
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Patent number: 6462217Abstract: Organolead compounds such as tetraethyllead are useful in catalyst compositions for the oxidative carbonylation of hydroxyaromatic compounds to diaryl carbonates. They are employed in combination with a Group 8, 9, or 10 metal such as palladium, or a compound thereof, and a bromide or chloride such as tetraethylammonium bromide.Type: GrantFiled: October 30, 2000Date of Patent: October 8, 2002Assignee: General Electric CompanyInventors: Kirill Vladimirovich Shalyaev, Bruce Fletcher Johnson
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Patent number: 6452036Abstract: The invention generally concerns methods for the synthesis of dialkyl carbonates, and more specifically dimethyl carbonate (DMC) and diethyl carbonate (DEC). Methods according to the invention generally comprise reacting an alcohol or diol, a base and a halogen in the presence of an amine salt catalyst thereby forming a first intermediate. The first intermediate is reacted with carbon monoxide forming a second intermediate which then reacts with the alcohol or diol in the presence of the amine salt catalyst forming the dialkyl carbonate product.Type: GrantFiled: May 2, 2002Date of Patent: September 17, 2002Assignee: Jacam Chemicals, L.L.C.Inventors: Gene H. Zaid, Beth Ann Wolf
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Patent number: 6407279Abstract: An integrated process for the production of a dialkyl carbonate and a diol from an alkylene oxide, carbon dioxide and an aliphatic monohydric alcohol is described in which an alkylene oxide is first reacted with carbon dioxide in the presence of a carbonation catalyst to provide a corresponding cyclic carbonate and impurities and the cyclic carbonate, which contains the impurities, is then reacted with an aliphatic monohydric alcohol in the presence of a transesterification catalyst to provide a corresponding dialkyl carbonate and diol.Type: GrantFiled: November 19, 1999Date of Patent: June 18, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jocelyn A. Kowalski, Jose G. Santiesteban
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Patent number: 6392078Abstract: A process for producing dialkyl carbonates, such as dimethyl carbonate, from the reaction of a primary alcohol with urea in the presence of a catalyst which is a complex compound represented by R2Sn(OCH3)2.&khgr;L, wherein R=CnH2n+1, n=1 to 12, &khgr;=1 or 2, and L is oxygen atom containing organic complexing agent which is carried out by conducting the reaction continuously under reactive distillation conditions wherein the product DMC is stripped from the reaction mixture with methanol and further including the recovery of product dimethyl carbonate (DMC) made in the process by contacting a stream containing the DMC, such as a azeotropic mixture with methanol, with diethyl oxylate under conditions of extractive distillation to selectively separate the DMC from methanol.Type: GrantFiled: May 25, 2001Date of Patent: May 21, 2002Assignee: Catalytic Distillation TechnologiesInventors: J. Yong Ryu, Abraham P. Gelbein
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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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Patent number: 6365767Abstract: A method is provided for co-producing dialkyl carbonate and alkanediol by reacting alkylene carbonate with alkanol in the presence of a zeolite catalyst which contains alkali metal, alkaline earth metal, or a combination thereof present in excess of a stoichiometric amount.Type: GrantFiled: August 20, 1999Date of Patent: April 2, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: Clarence D. Chang, Zhaozhong Jiang, Rene B. LaPierre, Suzanne E. Schramm, Hye Kyung Cho Timken
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Patent number: 6359163Abstract: A process for producing a dialkyl carbonate which comprises performing reaction of allophanate represented by the following general formula (1) and an alkyl alcohol represented by the following general formula (2) as raw materials, thereby producing a dialkyl carbonate represented by the following general formula (3). RO—CO—NH—CO—NH2 (1) ROH (2) RO—CO—OR (3) wherein R is an alkyl group.Type: GrantFiled: June 11, 2001Date of Patent: March 19, 2002Assignee: Mitsubishi Gas Chemical Company Inc.Inventors: Masamichi Mizukami, Yoshihisa Arai, Hidefumi Harada
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Patent number: 6355824Abstract: A method and catalyst system for producing aromatic carbonates from aromatic hydroxy compounds. In one embodiment, the method includes the step of contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system having an effective amount of an iron source in the absence of a Group VIII B metal source. In various alternative embodiments, the carbonylation catalyst system can include at least one inorganic co-catalyst, as well as a halide composition and/or a base.Type: GrantFiled: December 4, 2000Date of Patent: March 12, 2002Assignee: General Electric CompanyInventors: Ben Purushotam Patel, Grigorii Lev Soloveichik, Donald Wayne Whisenhunt, Jr., Kirill Vladimirovich Shalyaev
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Publication number: 20020018938Abstract: The present invention provides a solid polymer electrolyte; a polymerizable composition having low viscosity and excellent processability for obtaining the solid polymer electrolyte; and a polymerizable compound having low viscosity, and good polymerizability and stability for use in the polymerizable composition. The present invention also provides primary and secondary batteries capable of working with high capacity and current; an electric double-layer capacitor ensuring high output voltage, large takeout current, and good processability; and an electrochromic device favored with high response speed. Each thereof use the solid polymer electrolyte of the present invention and are ensured with long life, excellent safety free of liquid leakage, high reliability and production at a low cost.Type: ApplicationFiled: July 10, 2001Publication date: February 14, 2002Applicant: SHOWA DENKO KABUSHIKI KAISHAInventors: Masataka Takeuchi, Shuichi Naijo, Ayako Nishioka
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Patent number: 6346638Abstract: A method for continuously producing a (A) dialkyl carbonate and a (B) diol, comprising continuously feeding a cyclic carbonate and an aliphatic monohydric alcohol to a continuous multi-stage distillation column to thereby effect a transesterification therebetween, thereby continuously producing a dialkyl carbonate and a diol, while continuously withdrawing a low boiling point mixture containing the produced dialkyl carbonate (A) in a gaseous form from an upper portion of the distillation column and continuously withdrawing a high boiling point mixture containing the produced diol (B) in a liquid form from a lower portion of the distillation column, wherein the transesterification is performed under conditions wherein: (a) the reaction pressure of the column bottom is 5×104 Pa or less; (b) the reaction temperature of the column bottom is in the range of from −20° C. to less than 60° C.; and (c) the distillation column has an F-factor in the range of from 0.2 to 5.Type: GrantFiled: November 6, 2000Date of Patent: February 12, 2002Assignee: Asahi Kasel Kabushiki KaishaInventors: Masahiro Tojo, Kazuhiro Oonishi
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Patent number: 6342623Abstract: A method is provided for co-producing dialkyl carbonate and alkanediol by reacting alkylene carbonate with alkanol in the presence of an amorphous aluminosilicate catalyst containing alkali metal, alkaline earth metal, or a combination thereof.Type: GrantFiled: February 4, 2000Date of Patent: January 29, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: Clarence D. Chang, Larry E. Hoglen, Zhaozhong Jiang, Rene B. LaPierre
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Patent number: 6331535Abstract: The present invention relates to novel retinol derivatives having the formula (I): and to processes for preparing them. The invention also relates to the use of these compounds in or for the preparation of compositions intended for treating conditions of the skin or scalp, for example in preventing or combating acne and/or chronological or actinic ageing of the skin.Type: GrantFiled: May 30, 2000Date of Patent: December 18, 2001Assignee: L'OrealInventors: Remy Tuloup, Maria Dalko, Gilles Rubinstenn
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Patent number: 6315868Abstract: A method of separating methanol and dimethyl carbonate in a distillation column through extractive distillation. The extractive distillation is conducted in the presence of an extractive distillation agent which modifies the azeotropic behavior of the dimethyl carbonate/methanol mixture. A vapor side stream is removed from the distillation column.Type: GrantFiled: April 26, 1999Date of Patent: November 13, 2001Assignee: General Electric CompanyInventors: Alberto Nisoli, Stephan Mathijs Bouwens, Michael Francis Doherty, Michael Francis Malone
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Patent number: 6284911Abstract: A method for making a vinyl carbonate represented by the formula (I): CH2═CHOC(O)X1R1 (I) wherein X1 is oxygen or sulfur and R1 is a substituted or an unsubstituted aliphatic alkyl, aryl, aryl alkyl, olefinic, vinyl, or cycloaliphatic group comprises: (a) reacting a compound represented by the formula (II): X2C(O)X1R1 (II) wherein X2 is a halogen other than fluorine, with a compound represented by the formula (III): M1—F (III) wherein M1 is selected from a Group IA metal, in the presence of a first phase transfer catalyst and a first organic solvent, to form a compound represented by the formula (IV): FC(O)X1R1 (IV); and (b) reacting a compound represented by the formula (IV) with a compound represented by the formula (V): CH2═CHOSi(R2)3 (V) wherein R2 is a substituted or an unsubstituted aliphatic alkyl, aryl, aryl alkyl olefinic, vinyl, or cycloaliphatic group, or any combination thereof, in the presence of a metal saltType: GrantFiled: June 28, 2000Date of Patent: September 4, 2001Assignee: Wright Chemical CorporationInventors: David Lewis Allen, Heather Fort Henry, Becky Lynn Cahill, John Ponton, Jr., Kathryn Marie Church
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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: 6169197Abstract: A process for separation between dialkyl carbonate and alkyl carbamate which comprises adding an aromatic hydroxy compound to a liquid comprising alkyl carbamate having an alkyl group having 3 to 6 carbon atoms and dialkyl carbonate having alkyl group having 3 to 6 carbon atoms to obtain a mixed liquid, and distilling the mixed liquid thus obtained in a distillation column to obtain a mixture comprising the dialkyl carbonate and the aromatic hydroxy compound from a top section of the distillation column and a liquid comprising the alkyl carbamate from a bottom section of the distillation column.Type: GrantFiled: June 15, 1999Date of Patent: January 2, 2001Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takuo Ohshida, Hiroaki Ohgi, Yoshihisa Arai, Masamichi Mizukami
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Patent number: 6166240Abstract: A method is provided for co-producing dialkyl carbonate and alkanediol by reacting alkylene carbonate with alkanol in the presence of a Group 5 or Group 6 metal oxide catalyst.Type: GrantFiled: February 22, 2000Date of Patent: December 26, 2000Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Larry E. Hoglen, Zhaozhong Jiang, Rene B. LaPierre
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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: 6063952Abstract: Carbonate ester is produced by acid hydrolysis of the reaction product of cupric alkoxide induced reaction between a hydroxy compound and a sulfur compound in a melt process. Diaryl carbonate is produce by hydrolysis of the resulting orthoester.Type: GrantFiled: August 14, 1998Date of Patent: May 16, 2000Assignee: General Electric CompanyInventors: Deborah Ann Haitko, Marsha Mottel Grade
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Patent number: 6037298Abstract: A particularly useful process of contacting a feedstream containing dioxygen, carbon monoxide, ether, and alkanol which can be vaporized under conditions of reaction, with a blend of catalysts which are heterogeneous to the feedstream, under conditions of reaction sufficient to form a mixture containing at least one higher molecular weight oxygenated organic compound. In another aspect this invention relates to a blend of catalysts consisting of at least one molecular sieve, natural or synthetic, which has been found useful for hydrocarbon conversion reactions and a catalyst comprising a metal halide or a mixed metal halide supported on active carbon which is effective in catalyzing direct formation of organic carbonates.Type: GrantFiled: November 18, 1997Date of Patent: March 14, 2000Assignee: BP Amoco CorporationInventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6031122Abstract: A process for producing a dialkyl carbonate which comprises reacting at least one member selected from the group consisting of urea and alkyl carbamate with alcohol in the presence of both a catalyst and a high boiling point organic compound having a boiling point of 180.degree. C. or above.Type: GrantFiled: March 12, 1998Date of Patent: February 29, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masamichi Mizukami, Yoshihisa Arai, Hidefumi Harada, Takuo Ohshida, Hiroaki Ohgi
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Patent number: 6008399Abstract: A process for preparing organic carbonates, such as dimethyl carbonate, without the use of phosgene and with a high yield and selectivity to the desired carbonate, by reacting a formaldehyde-acetal with a source of oxygen, in the presence of a catalyst.Type: GrantFiled: March 11, 1999Date of Patent: December 28, 1999Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Jose G. Santiesteban
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Patent number: 5986125Abstract: The invention relates to a process for the production of higher dialkyl carbonates corresponding to formula (I):(R.sup.1 O)(R.sup.2 O)CO (I)which R.sup.1 and R.sup.2 may be the same or different and represent a linear or branched, saturated or unsaturated and/or alkoxylated alkyl group, by transesterification of lower dialkyl carbonates with higher alcohols in the presence of a catalyst. The process is characterized in that the transesterification is carried out in a column equipped with packings or internals through which the reactants flow in countercurrent to one another. Predominantly symmetrical dialkyl carbonates are obtained.Type: GrantFiled: March 4, 1998Date of Patent: November 16, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Erich Reuter, Walter Knoerr, Bernhard Gutsche
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Patent number: 5980445Abstract: A process for producing diaryl carbonate which comprises (A) a step for producing dialkyl carbonate represented by the general formula RO--CO--OR by reacting urea with alkyl alcohol represented by the general formula ROH, (B) a step for producing both alkyl aryl carbonate represented by the general formula RO--CO--OAr and diaryl carbonate represented by the general formula ArO--CO--OAr by reacting dialkyl carbonate produced in the above step (A) with an aromatic hydroxy compound represented by the general formula ArOH, and (C) a step for producing diaryl carbonate represented by the general formula ArO--CO--OAr by allowing to conduct disproportionation reaction of unreacted alkyl aryl carbonate produced in the above step (B), wherein R shows an alkyl group and Ar shows a non-substituted phenyl group or a phenyl group substituted by alkyl group, alkoxy group, aryl group, aryloxy group or halogen.Type: GrantFiled: November 6, 1997Date of Patent: November 9, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masamichi Mizukami, Yoshihisa Arai, Hidefumi Harada, Takuo Ohshida, Hiroaki Ohgi
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Patent number: 5973184Abstract: A dialkyl carbonate (e.g., dimethyl carbonate) is prepared at a high yield and a high selectivity by decarbonylation of a dialkyl oxalate (e.g., dimethyl oxalate) in a gaseous phase in the presence of an alkali metal compound (e.g., potassium carbonate).Type: GrantFiled: November 9, 1998Date of Patent: October 26, 1999Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Ryoji Sugise, Masayuki Nishio, Toshio Kurafuji, Toshihiro Shimakawa
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Patent number: 5962699Abstract: A process for decolorizing organic carbonates, for example, cyclic alkylene carbonates, which involves contacting a discolored organic carbonate with hydrogen peroxide, is disclosed.Type: GrantFiled: July 23, 1998Date of Patent: October 5, 1999Assignee: Huntsman Petrochemical CorporationInventors: Edward T. Marquis, Robert E. Baldwin
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Patent number: 5962720Abstract: The present invention relates to an improved method of synthesizing unsymmetric linear organic carbonates comprising the reaction of two symmetric dialkyl carbonates, R.sup.1 and R.sup.2, in the presence of a nucleophilic reagent or an election donating reductant as a catalyst, wherein R.sup.1 and R.sup.2 can be either saturated or unsaturated alkyl or aryl groups, is described. The present invention further provides a preparation method for a nonaqueous organic electrolyte having an unsymmetric linear organic carbonate as a co-solvent.Type: GrantFiled: May 29, 1997Date of Patent: October 5, 1999Assignee: Wilson Greatbatch Ltd.Inventors: Hong Gan, Marcus Palazzo, Esther S. Takeuchi
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Patent number: 5907051Abstract: A method of producing a carbonic diester involves allowing an alcohol to react with carbon monoxide and oxygen in the presence of a supported catalyst wherein the support is an activated carbon obtained from a vegetable or polymeric raw material, a support having an aluminum content of up to 2% by weight, or a support having sulfur content of up to 1% by weight.Type: GrantFiled: December 23, 1993Date of Patent: May 25, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Hirokazu Matsuda, Shingo Oda, Mitsuru Ohno
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Patent number: 5902894Abstract: A process for producing dialkyl carbonates, such as dimethyl carbonate, from the reaction of a primary alcohol with urea in the presence of a novel organotin catalyst complex with a high boiling electron donor compound acting as solvent which are (1) materials having the general formula RO?CH.sub.2 (CH.sub.2).sub.k CH.sub.2 O!.sub.m R, wherein each R is independently selected from C.sub.1-12 alkyl, alkaryl or aralkyl moieties, k=0,1, 2 or 3 and m=1, 2, 3, 4 or 5 and (2) bidentate ligand which form 1:1 bidentate and/or 1:2 monodentate adducts with R'.sub.2 SnX.sub.2 (X=Cl, R'O, R'COO or R'COS), R'.sub.3 SnX, R'SnO, Ph.sub.3-n R'SnX.sub.n or Ph.sub.4-n SnX.sub.n (wherein R'=C.sub.q H.sub.2q-1 n=0, 1 or 2 and q=2 to 12) and mixtures thereof.Type: GrantFiled: August 26, 1998Date of Patent: May 11, 1999Assignee: Catalytic Distillation TechnologiesInventor: J. Yong Ryu
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Patent number: 5892091Abstract: A catalyst composed of an organic phosphorus compound having a trivalent or pentavalent phosphorus atom and at least one carbon-phosphorus bonding or a combination of the organic phosphorus compound and a halogen atom-containing compound is effective for decarbonylation, that is, for releasing carbon monoxide from a compound containing a moiety of --CO--CO--O-- in its molecular structure.Type: GrantFiled: July 8, 1997Date of Patent: April 6, 1999Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Yoichi Imbe, Keigo Nishihira, Shuji Tanaka, Satoru Fujitsu, Ryoji Sugise, Koichi Kashiwagi, Toshihiko Sumida, Takashi Doi, Masayuki Nishio
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Patent number: 5869729Abstract: An ester compound, for example, carbonic acid ester or succinic acid ester, is produced by catalytically reacting, in gas phase, carbon monoxide with a nitrous acid ester and optionally an olefin in the presence of a catalyst and in the presence of a chlorine-containing substance, bringing the reaction product-containing mixed gas into contact with a solid catalyst such as activated carbon or inorganic oxide to reduce the content of the chlorine-containing substance, cool-condensing the resultant mixed gas, and collecting the target ester compound from the condensed liquid.Type: GrantFiled: June 27, 1996Date of Patent: February 9, 1999Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Shuji Tanaka, Yuki Nishida, Noriaki Manada, Toshio Kurafuji, Masato Murakami
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Patent number: 5856553Abstract: The invention relates to the compounds having the structures I and II: ##STR1## The invention also relates to a method of making the compound having the structure I by mixing 2,2,4,4-tetramethyl-1,3-cyclobutanediol; dimethyl carbonate; and a basic catalyst, and heating the mixture.Type: GrantFiled: December 23, 1997Date of Patent: January 5, 1999Assignee: Eastman Chemical CompanyInventors: Theodore R. Walker, Jean C. Fleischer, William R. Darnell
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Patent number: 5847188Abstract: A novel carbonate compound represented by the general formula ?I!:R.sup.1 CH.sub.2 O--CO--OCH.sub.2 R.sup.2 ?I!wherein R.sup.1 represents a hydrogen atom, an alkyl group or an alkyl group substituted with one or more halogen atoms, and R.sup.2 represent an alkyl group having no hydrogen atom at the .alpha.-position thereof or an alkyl group substituted with one or more halogen atoms having no hydrogen atom at the .alpha.-position thereof, with the proviso that R.sup.1 is not identical to R.sup.2, which has excellent properties as solvent, is disclosed. A non-aqueous electrolytic solution and a battery utilizing the novel carbonate compound are also disclosed.Type: GrantFiled: April 17, 1997Date of Patent: December 8, 1998Assignee: Mitsui Chemicals, Inc.Inventors: Keiichi Yokoyama, Akio Hiwara, Shigeru Fujita, Atsuo Omaru
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Patent number: RE37337Abstract: A process for producing dialkyl carbonates, such as dimethyl carbonate, from the reaction of a primary alcohol with urea in the presence of a novel organotin catalyst complex with a high boiling electron donor compound acting as solvent which are (1) materials having the general formula RO[CH2(CH2)kCH2O]mR, wherein each R is independently selected from C1-12 alkyl, alkaryl or aralkyl moieties, k=0,1, 2 or 3 and m=1, 2, 3, 4 or 5 and (2) bidentate ligand which form 1:1 bidentate and/or 1:2 monodentate adducts with R′2SnX2(X═Cl, R′O, R′COO or R′COS), R′3SnX, R′SnO, Ph3-nR′SnXn or Ph4-nSnXn (wherein R′=CqH2q-1n=0, 1 or 2 and q=2 1 to 12) and mixtures thereof, such as materials having the general formula RO[CH2(CH2)xCH2O]mR, wherein each R is independently selected from C1-12 alkyl, alkaryl or aralkyl moieties, k=0,1, 2 or 3 and m=1, 2, 3, 4, or 5.Type: GrantFiled: August 17, 1999Date of Patent: August 21, 2001Assignee: Catalytic Distillation TechnologiesInventor: J. Yong Ryu