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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Patent number: 7563919Abstract: An alkanediol and a dialkyl carbonate are prepared in a process comprising: (a) contacting an alkylene carbonate with an alkanol feedstock under transesterification conditions in a reactive distillation zone to obtain a top stream comprising dialkyl carbonate and the alkanol and a bottom stream comprising an alkanediol; (b) separating the top stream comprising dialkyl carbonate and the alkanol into an alkanol-rich stream and a dialkyl carbonate-rich stream; (c) recovering the dialkyl carbonate from the dialkyl carbonate-rich stream; and (d) recycling at least part of the alkanol-rich stream to the reactive distillation zone as part of the alkanol feedstock, wherein the alkanol-rich stream is split in at least two portions, and at least one portion is condensed and freed from compounds with a lower boiling point than the alkanol. The process is especially suitable for the production of propylene glycol and dimethyl carbonate from propylene carbonate and methanol.Type: GrantFiled: February 22, 2007Date of Patent: July 21, 2009Assignee: Shell Oil CompanyInventors: Evert Van Der Heide, Timothy Michael Nisbet, Garo Garbis Vaporciyan
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Publication number: 20090156853Abstract: It is an object of the present invention to provide a specific process that enables a dialkyl carbonate and a diol to be produced on an industrial scale of not less than 2 ton/hr and not less than 1.3 ton/hr respectively with high selectivity and high productivity stably for a prolonged period of time through a reactive distillation system of taking a cyclic carbonate and an aliphatic monohydric alcohol as starting materials, continuously feeding the starting materials into a continuous multi-stage distillation column in which a catalyst is present, and carrying out reaction and distillation simultaneously in the column. Although there have been many proposals regarding processes for the production of the dialkyl carbonate and the diol through the reactive distillation method, these have all been on a small scale and short operating time laboratory level, and there have been no disclosures whatsoever on a specific process or apparatus enabling mass production on an industrial scale.Type: ApplicationFiled: December 6, 2006Publication date: June 18, 2009Applicant: Asahi Kasei chemcials corporationInventors: Shinsuke Fukuoka, Hironori Miyaji, Hiroshi Hachiya, Kazuhiko Matsuzaki
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Publication number: 20090149669Abstract: It is an object of the present invention to provide, for a case of producing a dialkyl carbonate and a diol from a cyclic carbonate and an aliphatic monohydric alcohol, a process that simultaneously satisfies the cyclic carbonate conversion being high, the selectivities for the dialkyl carbonate and diol to be produced being high, and a high-purity diol having a high UV transmittance and a low aldehyde content being obtained without carrying out complicated treatment such as feeding water into a diol distillation purification step.Type: ApplicationFiled: September 5, 2006Publication date: June 11, 2009Applicant: ASAHI KASEI CHEMICALS CORPORATIONInventors: Hironori Miyaji, Shinsuke Fukuoka, Hiroshi Hachiya
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Patent number: 7541482Abstract: A process for the production of alkyltin alkoxides which comprises subjecting at least one alkyltin compound selected from among organotin compounds having tin-oxygen-tin linkages as the starting compound and a hydroxyl compound as the reactant to dehydration to obtain an alkyltin alkoxide corresponding to the starting compound and the reactant, characterized by continuously feeding the starting compound and the reactant into a reactor, discharging a water-containing low boiling point component from the reactor, and continuously withdrawing a reaction fluid containing an alkyltin alkoxide as the bottom from the reactor.Type: GrantFiled: May 18, 2005Date of Patent: June 2, 2009Assignee: Asahi Kasei Chemicals CorporationInventors: Nobuhisa Miyake, Kazuhiro Onishi, Budianto Bijanto
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Publication number: 20090137833Abstract: It is an object of the present invention to provide a specific process that enables a dialkyl carbonate and a diol to be produced on an industrial scale of not less than 2 ton/hr and not less than 1.3 ton/hr respectively with high selectivity and high productivity stably for a prolonged period of time through a reactive distillation system of taking a cyclic carbonate and an aliphatic monohydric alcohol as starting materials, continuously feeding the starting materials into a continuous multi-stage distillation column in which a catalyst is present, and carrying out reaction and distillation simultaneously in the column. Although there have been many proposals regarding processes for the production of the dialkyl carbonate and the diol through the reactive distillation method, these have all been on a small scale and short operating time laboratory level, and there have been no disclosures whatsoever on a specific process or apparatus enabling mass production on an industrial scale.Type: ApplicationFiled: November 17, 2006Publication date: May 28, 2009Applicant: Asahi Kasei Chemicals CorporationInventors: Shinsuke Fukuoka, Hironori Miyaji, Hiroshi Hachiya, Kazuhiko Matsuzaki
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Patent number: 7531616Abstract: It is an object of the present invention to provide a specific process that enables aromatic carbonates to be produced with high selectivity and high productivity stably for a prolonged period of time on an industrial scale of not less than 1 ton per hour from a dialkyl carbonate and an aromatic monohydroxy compound using two continuous multi-stage distillation columns. Although there have been various proposals regarding processes for the production of aromatic carbonates by means of a reactive distillation method, these have all been on a small scale and short operating time laboratory level, and there have been no disclosures whatsoever on a specific process or apparatus enabling mass production on an industrial scale.Type: GrantFiled: July 12, 2005Date of Patent: May 12, 2009Assignee: Asahi Kasei Chemicals CorporationInventors: Shinsuke Fukuoka, Hiroshi Hachiya, Kazuhiko Matsuzaki
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Publication number: 20090105494Abstract: It is an object of the present invention, when producing a dialkyl carbonate and a diol industrially in a large amount (e.g. not less than 2 ton/hr for the dialkyl carbonate and not less than 1.3 ton/hr for the diol) through a reactive distillation system of taking a cyclic carbonate and an aliphatic monohydric alcohol as starting materials, continuously feeding the starting materials into a continuous multi-stage distillation column in which a catalyst is present, and carrying out reaction and distillation simultaneously in the column, is to provide a specific process that enables the dialkyl carbonate and the diol to be produced each with high selectivity and high productivity stably for a prolonged period of time (e.g. not less than 1000 hours, preferably not less than 3000 hours, more preferably not less than 5000 hours), and moreover enables the dialkyl carbonate produced to be separated out and purified stably for a prolonged period of time with high efficiency.Type: ApplicationFiled: December 20, 2006Publication date: April 23, 2009Inventors: Shinsuke Fukuoka, Hironori Miyaji, Hiroshi Hachiya, Kazuhiko Matsuzaki
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Publication number: 20090099384Abstract: The present invention provides a method of remedying deterioration of an insulating film which, during the remedial treatment of an insulating film deteriorated by plasma treatment, does not leave residual remedial agent on the wiring material such as the copper wiring layer, can be conducted using a dry process, and exhibits excellent applicability to mass production. The insulating film that has been deteriorated by plasma treatment is brought into contact with a remedial agent composed of a compound with a molecular structure having at least one of a nitro group and a carbonyl group, and at least one of a hydrocarbon group and a hydrogen group.Type: ApplicationFiled: April 18, 2007Publication date: April 16, 2009Inventors: Shuji Nagano, Satoshi Hasaka, Minoru Inoue, Toshinori Shibata
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Patent number: 7518012Abstract: The present invention provides a process for the preparation of dialkyl carbonates of general formula (1) wherein R=alkyl (C1-C8) or C6H5CH2 the said process comprises a reaction in between cyclic carbonate and alcohol, in the presence of a solid, double metal cyanide complex catalyst, at a temperature in the range of 140-180° C., for a period of 4-10 hrs, followed by the separation of catalyst from the above said reaction mixture by known methods to obtain the desired product.Type: GrantFiled: March 30, 2006Date of Patent: April 14, 2009Assignee: Council of Scientific & Industrial ResearchInventors: Darbha Srinivas, Rajendra Srivastava, Paul Ratnasamy
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Patent number: 7514521Abstract: 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: GrantFiled: August 14, 2001Date of Patent: April 7, 2009Assignee: SABIC Innovative Plastics IP B.V.Inventors: Eugene Pauling Boden, Ganesh Kailasam, Larry Neil Lewis, Ignacio Vic Fernandez
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Patent number: 7504527Abstract: 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: GrantFiled: August 15, 2003Date of Patent: March 17, 2009Assignee: Badger Licensing, LLCInventors: Richard H. Schlosberg, J. Scott Buchanan, Jose Guadalupe Santiesteban, Zhaozhong Jiang, William A. Weber
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Publication number: 20090054676Abstract: It is an object of the present invention to provide a specific apparatus and process for using a single distillation column on a low boiling point reaction mixture containing a large amount of a dialkyl carbonate and an aliphatic monohydric alcohol produced through a reactive distillation process of taking a cyclic carbonate and the aliphatic monohydric alcohol as starting materials, continuously feeding the starting materials into a continuous multi-stage distillation column in which a homogeneous catalyst is present, and carrying out reaction and distillation simultaneously in the column, so as to separate the low boiling point reaction mixture by distillation into a column top component BT having the aliphatic monohydric alcohol as a main component thereof and a column bottom component BB having the dialkyl carbonate as a main component thereof stably for a prolonged period of time industrially.Type: ApplicationFiled: December 15, 2006Publication date: February 26, 2009Applicant: ASAHI KASEI CHEMICALS CORPORATIONInventors: Shinsuke Fukuoka, Hironori Miyaji, Hiroshi Hachiya, Kazuhiko Matsuzaki
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Patent number: 7491837Abstract: 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: GrantFiled: August 15, 2003Date of Patent: February 17, 2009Assignee: Badger Licensing LLC.Inventors: Richard H. Schlosberg, J. Scott Buchanan, Jose Guadalupe Santiesteban, Zhaozhong Jiang, William A. Weber
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Publication number: 20090030223Abstract: It is an object of the present invention to provide a solution by providing a specific process that enables a dialkyl carbonate and a diol to be produced on an industrial scale of not less than 2 ton/hr and not less than 1.3 ton/hr respectively with high selectivity and high productivity stably for a prolonged period of time through a reactive distillation system of taking a cyclic carbonate and an aliphatic monohydric alcohol as starting materials, continuously feeding the starting materials into a continuous multi-stage distillation column in which a catalyst is present, and carrying out reaction and distillation simultaneously in the column. Although there have been many proposals regarding processes for the production of the dialkyl carbonate and the diol through the reactive distillation method, these have all been on a small scale and short operating time laboratory level, and there have been no disclosures whatsoever on a specific process or apparatus enabling mass production on an industrial scale.Type: ApplicationFiled: December 6, 2006Publication date: January 29, 2009Applicant: ASAHI KASEI CHEMICALS CORPORATIONInventors: Shinsuke Fukuoka, Hironori Miyaji, Hiroshi Hachiya, Kazuhiko Matsuzaki
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Publication number: 20090005585Abstract: A system and method for a high shear mechanical device incorporated into a process for the production of acetic anhydride as a reactor device is shown to be capable of decreasing mass transfer limitations, thereby enhancing the process. A system for the production of acetic anhydride including the mixing of catalyst and acetic acid via a high shear device.Type: ApplicationFiled: June 10, 2008Publication date: January 1, 2009Applicant: HRD CORP.Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7462336Abstract: An apparatus for preparing a dialkyl carbonate comprises means for reacting an alkanol, oxygen, carbon monoxide, and a catalyst to form a mixture comprising a dialkyl carbonate, an alkyl chloroformate, hydrochloric acid, water, carbon dioxide, and carbon monoxide; means for separating from the mixture a gaseous fraction comprising carbon monoxide and alkyl chloroformate; and means for removing alkyl chloroformate from the gaseous fraction.Type: GrantFiled: June 27, 2005Date of Patent: December 9, 2008Assignee: Sabic Innovative Plastics IP B.V.Inventors: Jan van de Broek, Stephan Bouwens, Maarten Campman, Daniel Favre, Cornelis Adrianus Maria van Gool, Leon Kalle, George P. Moloney, Jr.
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Patent number: 7453007Abstract: 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: June 9, 2005Date of Patent: November 18, 2008Assignee: Badger Licensing, LLCInventors: J. Scott Buchanan, Zhaozhong Jiang, Jose Guadalupe Santiesteban, William A. Weber
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Publication number: 20080249327Abstract: The invention relates to an improved catalyst for the synthesis of dimethyl carbonate by reacting methanol, carbon monoxide and oxygen in the gas phase and to the use thereof. The catalyst consists of a copper-containing zeolite produced by admixing one or more halide-free copper(II) compounds to a zeolite in a liquid medium, drying the zeolite modified by the admixture, and tempering at 400-900° C. under inert conditions, essentially retaining the crystallinity of the zeolite, said admixing being effected by means of a method selected from the group consisting of impregnation of the zeolite, ion exchange, precipitation of copper(II) hydroxide in the presence of the zeolite, and a combination of these methods. The catalyst shows high space-time yields, is constant over the period of operation and has no corrosive action.Type: ApplicationFiled: January 23, 2006Publication date: October 9, 2008Inventors: Reinhard Eckelt, Martin J.G. Fait, Rolf Fricke, Manfred Richter
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Publication number: 20080242882Abstract: A method for producing a dialkyl carbonate and a diol, comprising: (a) effecting a transesterification reaction between a cyclic carbonate and an aliphatic monohydric alcohol in the presence of a transesterification catalyst, thereby obtaining a reaction mixture containing a product dialkyl carbonate and a product diol, (b) withdrawing a dialkyl carbonate-containing liquid from the reaction mixture, followed by separation of the dialkyl carbonate from the dialkyl carbonate-containing liquid, and (c) withdrawing a diol-containing liquid from the reaction mixture, followed by separation of the diol from the diol-containing liquid, wherein the cyclic carbonate contains a cyclic ether in an amount of from 0.1 to 3,000 ppm by weight, and the product dialkyl carbonate contains a carbonate ether of not more than 10,000 ppm by weight.Type: ApplicationFiled: June 17, 2005Publication date: October 2, 2008Inventors: Masahiro Tojo, Hironori Miyaji
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Publication number: 20080241599Abstract: A carbonic acid ester is provided that is represented by the formula below and has a melting point of no greater than 0° C. (In the formula, R1 and R2 independently denote a saturated hydrocarbon group, R1 is a branched chain, and R2 is a straight or branched chain). There is also provided a magnetic recording medium that includes a non-magnetic support and, above the support, at least one magnetic layer including a ferromagnetic powder dispersed in a binder, the magnetic layer including the carbonic acid ester. Furthermore, there is provided a magnetic recording medium including a support and, above the support, a non-magnetic layer including a non-magnetic powder dispersed in a binder, and above the non-magnetic layer, at least one magnetic layer including a ferromagnetic powder dispersed in a binder, the non-magnetic layer and/or the magnetic layer including the carbonic acid ester.Type: ApplicationFiled: March 28, 2008Publication date: October 2, 2008Applicant: FUJIFILM CORPORATIONInventors: Akira IMAKUNI, Masahiko MORI, Yoshihiro NAKAI
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Publication number: 20080221349Abstract: Processes for preparing amides of retinoic acid are disclosed. Intermediates useful in the preparation of amides of retinoic acid are also disclosed. In one version of the invention, fenretinide is produced via activation of retinoic acid (tretinoin) via its corresponding mixed anhydride or mixed carbonate followed by reaction of the activated intermediate with 4-aminophenol. Other amides of retinoic acid and isomers of retinoic acid, such as the 9-cis-form or 13-cis-form can also be made by this invention.Type: ApplicationFiled: January 2, 2008Publication date: September 11, 2008Inventors: John E. Cabaj, Jeff J. Hutchison, James R. Zeller
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Publication number: 20080214856Abstract: Provided is a process for preparation of dialkyl carbonates, comprising the step of performing oxidative carbonylation of an alcohol in liquid phase in the presence of CO and O2, to form dialkyl carbonate in a catalyst system comprising a metal halide as catalyst and at least one nitrogen-containing compound selected from the group consisting of imidazole derivatives (excluding unsubstituted imidazole), benzoimidazole derivatives, pyridazine derivatives, carbazole, acridine and non-cyclic amines as auxiliary catalyst. The process of the invention, by using above catalyst system, can increase the conversion ratio of alcohol and the selectivity of the oxidative carbonylation reaction, thus increasing the total yield of dialkyl carbonate. In addition, the process of the invention has the advantages of reducing the required amount of the catalyst and causing less corrosion to the reactor.Type: ApplicationFiled: January 15, 2008Publication date: September 4, 2008Applicant: China Petrochemical Development CorporationInventors: Chih-Wei Chang, Chia-Jung Tsai, Ying-Tien Chen
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Publication number: 20080200714Abstract: A method of forming a dialkyl carbonate stream, includes obtaining a byproduct stream from a diaryl carbonate formation reaction that has alkanol, residual dialkyl carbonate, and residual aromatic compound. This byproduct stream is introduced to a distillation column to produce an alkanol tops stream and a first dialkyl carbonate bottoms stream. The alkanol tops stream is reacted with oxygen, carbon monoxide, and catalyst to form a second dialkyl carbonate stream that is introduced to the distillation column. The alkanol tops stream from the column contains alkanol, dialkyl carbonate, and less than 20 ppm aromatic compound. The first dialkyl carbonate bottoms stream from the column contains dialkyl carbonate, water, aromatic compound, and less than 2,000 ppm alkanol and is introduced to a water separation device to produce a product dialkyl carbonate stream and a water stream.Type: ApplicationFiled: February 15, 2008Publication date: August 21, 2008Applicant: SABIC INNOVATIVE PLASTICS IP BVInventor: Ignacio Vic Fernandez
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Publication number: 20080200713Abstract: The present invention provides methods of forming dialkyl carbonate wherein catalyst buildup in the reaction equipment, the separation equipment, and transfer lines there between is reduced and even eliminated. In one embodiment, the method includes introducing alkanol, carbon monoxide, oxygen, and a catalyst to a reactor having a gaseous head space and a liquid body space. The reactor is operated under conditions to form dialkyl carbonate and water. A product stream containing dialkyl carbonate, water, and residual reactants is removed from the head space of the reactor and introduced to a cyclone with a flushing stream. A liquid bottom stream is captured from the cyclone and introduced to the reactor. The gaseous top stream contains product dialkyl carbonate.Type: ApplicationFiled: February 15, 2008Publication date: August 21, 2008Applicant: SABIC INNOVATIVE PLASTICS IP BVInventors: Ignacio Vic Fernandez, Benoit Fillion, Vutukuru Murthy, Vinod Sankaran Nair, Mario Perez Collado
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Publication number: 20080183002Abstract: An alkanediol and a dialkyl carbonate are prepared in a process comprising: (a) reacting an alkylene carbonate and an alkanol feedstock in a first reaction zone under transesterification conditions to obtain a product mixture of dialkyl carbonate, unconverted alkanol, the alkanediol, unconverted alkylene carbonate and dimers of the alkanediol; (b) separating dialkyl carbonate and alkanol from the product mixture to obtain a bottom product stream containing alkanediol, unconverted alkylene carbonate and dimers of the alkanediol; (c) recovering the dialkyl carbonate; and (d) separating alkanediol from the bottom product stream to leave a recycle stream comprising unconverted alkylene carbonate and dimers of the alkanediol, which process further comprises (e) passing at least part of the recycle stream to a second reaction zone in which the dimers of the alkanediol are converted to higher-boiling oligomers of alkanediol, yielding an oligomers-containing effluent; (f) separating the higher-boiling oligomers fromType: ApplicationFiled: January 21, 2008Publication date: July 31, 2008Inventors: Timothy Michael Nisbet, Garo Garbis Vaporciyan, Cornelis Leonardus Maria Vrouwenvelder, Paul Wood
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Patent number: 7385070Abstract: A method for catalytic conversion of alkylene carbonate, wherein alkylene carbonate is contacted with C1-C5 aliphatic alcohol and/or water in the presence of Mg, Al mixed (hydr) oxide catalyst having a Mg:Al molar ratio in the range of from 4 to 20.Type: GrantFiled: July 14, 2005Date of Patent: June 10, 2008Assignee: Shell Oil CompanyInventors: Johannes Petrus De Jonge, Jean-Paul Lange, Dennis Humphrey Louis Pello
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Publication number: 20080103040Abstract: The invention relates to a catalytic composition comprising: a first component which is at least a component with one or more metals from groups 3A, 4A, 5A, 6A, 7A, 8, 1B, 2B, 3B, 4B; and a second component selected from (1) at least one ionic liquid which consists of a compound formed by cations and anions and which is a liquid at ambient temperature, (ii) a matrix to which the first component is bound or on which it is supported, and (iii) a combination of the two. The invention relates to the use of said catalytic composition in a method for the insertion of carbon dioxide into an organic compound and, preferably, a compound selected from epoxides, acetals and orthoesters. The invention also relates to catalytic compositions comprising said metallic compounds.Type: ApplicationFiled: August 24, 2005Publication date: May 1, 2008Inventors: Mercedes Alvaro Rodriguez, Esther Carbonell Llopis, Avelino Corma Canos, Hermenegildo Garcia Gomez
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Patent number: 7351848Abstract: 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: GrantFiled: August 23, 2002Date of Patent: April 1, 2008Assignee: General Electric CompanyInventors: Eugene Pauling Boden, Ganesh Kailasam, Larry Neil Lewis, Alberto Nisoli, John Yaw Ofori, Angel Sanchez Gonzalez
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Patent number: 7345187Abstract: 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: GrantFiled: August 14, 2001Date of Patent: March 18, 2008Assignee: General Electric CompanyInventors: Eugene Pauling Boden, Ganesh Kailasam, Larry Neil Lewis, Alberto Nisoli, John Yaw Ofori, Angel Sanchez Gonzalez
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Patent number: 7314947Abstract: A process for the production of dialkyl carbonates from the reaction of alcohol, for example C1-C3 alcohols, with urea is disclosed wherein the water and ammonium carbamates impurities in the feed are removed in a prereactor. The water is reacted with urea in the feed to produce ammonium carbamate which is decomposed along with the ammonium carbamates originally in the feed to ammonia and carbon dioxide. In addition some of the urea is reacted with the alcohol in the first reactor to produce alkyl carbamate which is a precursor to dialkyl carbonate. Dialkyl carbonates are produced in the second reaction zone. The undesired by-product N-alkyl alkyl carbamates are continuously distilled off from the second reaction zone along with ammonia, alcohol and dialkyl carbonates under the steady state reactor operation. N-alkyl alkyl carbamates can be converted to heterocyclic compounds in a third reaction zone to remove as solids from the system.Type: GrantFiled: February 21, 2006Date of Patent: January 1, 2008Assignee: Catalytic Distillation TechnologiesInventors: J. Yong Ryu, Abraham P. Gelbein
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Patent number: 7279592Abstract: A process for the production of dialkyl carbonates from the reaction of alcohol, for example C1-C3 alcohols, with urea is disclosed wherein the water and ammonium carbamates impurities in the feed are removed in a prereactor. The water is reacted with urea in the feed to produce ammonium carbamate which is decomposed along with the ammonium carbamates originally in the feed to ammonia and carbon dioxide. In addition some of the urea is reacted with the alcohol in the first reactor to produce alkyl carbamate which is a precursor to dialkyl carbonate. Dialkyl carbonates are produced in the second reaction zone. The undesired by-product N-alkyl alkyl carbamates are continuously distilled off from the second reaction zone along with ammonia, alcohol and dialkyl carbonates under the steady state reactor operation. N-alkyl alkyl carbamates can be converted to heterocyclic compounds in a third reaction zone to remove as solids from the system.Type: GrantFiled: February 21, 2006Date of Patent: October 9, 2007Assignee: Catalytic Distillation TechnologiesInventors: J. Yong Ryu, Abraham P. Gelbein
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Patent number: 7094917Abstract: Processes for refining dialkyl carbonate-containing compositions are described, wherein a composition comprising a dialkyl carbonate is provided; and the composition is subjected to a rectification wherein low-boiling impurities are removed, and a rectification wherein high-boiling impurities are removed; and subsequently to a deodorization wherein medium-boiling impurities are removed.Type: GrantFiled: August 13, 2002Date of Patent: August 22, 2006Assignee: Cognis Deutschland GmbH & Co., KGInventors: Richard Ridinger, Levent Yueksel, Georg Fieg
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Patent number: 7084292Abstract: 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: GrantFiled: June 22, 2001Date of Patent: August 1, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jose G. Santiesteban, William A. Weber
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Patent number: 7074951Abstract: A process for the production of dialkyl carbonates from the reaction of alcohol, for example C1–C3 alcohols, with urea is disclosed wherein the water and ammonium carbamates impurities in the feed are removed in a prereactor. The water is reacted with urea in the feed to produce ammonium carbamate which is decomposed along with the ammonium carbamates originally in the feed to ammonia and carbon dioxide. In addition some of the urea is reacted with the alcohol in the first reactor to produce alkyl carbamate which is a precursor to dialkyl carbonate. Dialkyl carbonates are produced in the second reaction zone. The undesired by-product N-alkyl alkyl carbamates are continuously distilled off from the second reaction zone along with ammonia, alcohol and dialkyl carbonates under the steady state reactor operation. N-alkyl alkyl carbamates can be converted to heterocyclic compounds in a third reaction zone to remove as solids from the system.Type: GrantFiled: April 8, 2004Date of Patent: July 11, 2006Inventors: J. Yong Ryu, Abraham P. Gelbein
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Patent number: 7049457Abstract: A non-corrosive process for the preparation of dialkyl carbonate by reacting carbon monoxide, alkanol and an oxygen-containing gas in the presence of a ionic halogen free copper catalyst.Type: GrantFiled: September 5, 2003Date of Patent: May 23, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Robert T. Stibrany, Christian P. Mehnert, Michael G. Matturro
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Patent number: 6989459Abstract: Applicant has discovered an in situ method of preparing quaternary ammonium methocarbonate salts and quaternary ammonium alkylcarbonate salts in high yield from tertiary amines, methanol, and at least one of a cyclic carbonate, an aliphatic polyester (such as a polycarbonate), or an ester (such as a carbonate ester), and their subsequent conversion to quaternary ammonium bicarbonates, quaternary ammonium carbonates or both in a one-pot reaction. According to one embodiment of the invention, the method includes reacting an amine and methanol with at least one of a cyclic carbonate and an aliphatic polyester to yield a quaternary ammonium methocarbonate. This method does not produce or require the handling of corrosive quaternary ammonium hydroxides. Another embodiment is a method of preparing quaternary ammonium alkylcarbonate salts by reacting tertiary amines, methanol, and an ester.Type: GrantFiled: February 10, 2004Date of Patent: January 24, 2006Assignee: Lonza Inc.Inventor: Leigh E. Walker
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Patent number: 6977308Abstract: 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: GrantFiled: June 2, 2003Date of Patent: December 20, 2005Assignee: General Electric CompanyInventors: Jan van de Broek, Stephan Bouwens, Maarten Campman, Daniel Favre, Cornelis Adrianus Maria van Gool, Leon Kalle, George P. Moloney, Jr.
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Patent number: 6953864Abstract: A method for catalytic conversion of alkylene carbonate, wherein alkylene carbonate is contacted with C1-C5 aliphatic alcohol and/or water in the presence of Mg, Al mixed (hydr) oxide catalyst having a Mg:Al molar ratio in the range of from 4 to 20.Type: GrantFiled: November 12, 2002Date of Patent: October 11, 2005Assignee: Shell Oil CompanyInventors: Johannes Petrus De Jonge, Jean-Paul Lange, Dennis Humphrey Louis Pello
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Patent number: 6930195Abstract: 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: July 15, 2003Date of Patent: August 16, 2005Assignee: ExxonMobil Chemical Patents Inc.Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jose Guadalupe Santiesteban, William A. Weber
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Patent number: 6897343Abstract: The invention relates to a process for the preparation of 1,2-propanediol from propylene oxide, which process involves contacting propylene oxide with carbon dioxide in the presence of a homogeneous phosphorus containing catalyst to obtain propylene carbonate, optionally removing at least part of the carbon dioxide, adding water and/or an alcohol to the reaction product containing propylene carbonate and phosphorus containing catalyst and contacting the mixture with a heterogeneous catalyst to obtain 1,2-propanediol in combination with dialkylcarbonate and/or carbon dioxide, and separating 1,2-propanediol from the reaction product obtained.Type: GrantFiled: December 19, 2003Date of Patent: May 24, 2005Assignee: Shell Oil CompanyInventors: Klaas Lambertus Von Hebel, Jean-Paul Lange
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Patent number: 6844287Abstract: The present invention provides a process for preparing supported zinc dicarboxylate catalysts with high activity for the copolymerization of carbon dioxide and epoxides by supporting zinc dicarboxylate on silica support. The zinc dicarboxylate may be synthesized from zinc oxide and dicarboxylic acid such as succinic acid, glutaric acid, adipic acid, pimelic acid and suberic acid. The silica support can be selected from the group consisting of aerosil, silica gel for chromatography or reagent grade silicon dioxide. The supporting process is performed in a planetary ball grinder under vacuum.Type: GrantFiled: December 13, 2002Date of Patent: January 18, 2005Assignee: Guangzhou Institute of Chemistry, Chinese Academy of SciencesInventors: Yuezhong Meng, Quan Zhu, Shizhen Zhang, Xiuhua Li, Longchao Du
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Patent number: 6835858Abstract: The invention relates to a method for the catalytic conversion of organic carbonate to the corresponding alcohol, wherein the organic carbonate is contacted with alcohol and/or water in the presence of a zinc supported catalyst.Type: GrantFiled: September 10, 2003Date of Patent: December 28, 2004Assignee: Shell Oil CompanyInventors: Johannes Petrus De Jonge, Jean-Paul Lange
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Publication number: 20040242914Abstract: Processes for refining dialkyl carbonate-containing compositions are described, wherein a composition comprising a dialkyl carbonate is provided; and the composition is subjected to a rectification wherein low-boiling impurities are removed, and a rectification wherein high-boiling impurities are removed; and subsequently to a deodorization wherein medium-boiling impurities are removed.Type: ApplicationFiled: February 23, 2004Publication date: December 2, 2004Inventors: Richard Ridinger, Levent Yueksel, Georg Fieg
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Publication number: 20040218346Abstract: 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: June 3, 2004Publication date: November 4, 2004Applicant: SHOWA DENKO K.K.Inventors: Masataka Takeuchi, Shuichi Naijo, Ayako Nishioka
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Patent number: 6784307Abstract: Applicant has discovered an in situ method of preparing quaternary ammonium methocarbonate salts and quaternary ammonium alkylcarbonate salts in high yield from tertiary amines, methanol, and at least one of a cyclic carbonate, an aliphatic polyester (such as a polycarbonate), or an ester (such as a carbonate ester), and their subsequent conversion to quaternary ammonium bicarbonates, quaternary ammonium carbonates or both in a one-pot reaction. According to one embodiment of the invention, the method includes reacting an amine and methanol with at least one of a cyclic carbonateand an aliphatic polyester to yield a quaternary ammonium methocarbonate. This method does not produce or require the handling of corrosive quaternary ammonium hydroxides. Another embodiment is a method of preparing quaternary ammonium alkylcarbonate salts by reacting tertiary amines, methanol, and an ester.Type: GrantFiled: July 2, 2002Date of Patent: August 31, 2004Assignee: Lonza Inc.Inventor: Leigh E. Walker
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Patent number: 6774256Abstract: 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: GrantFiled: March 25, 2002Date of Patent: August 10, 2004Assignee: ExxonMobil Chemical Patents Inc.Inventors: Richard H. Schlosberg, J. Scott Buchanan, Jose Guadalupe Santiesteban, Zhaozhong Jiang, William A. Weber
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Patent number: 6768020Abstract: 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: GrantFiled: November 12, 2002Date of Patent: July 27, 2004Assignee: Shell Oil CompanyInventors: Johannes Petrus De Jonge, Jean-Paul Lange, Ingrid Maria Van Vegchel
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Patent number: 6723868Abstract: The invention relates to a novel process for the preparation of an aminoalcohol of the formula racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide of the formula to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae and then cyclized to give the end compounds.Type: GrantFiled: November 24, 1998Date of Patent: April 20, 2004Assignee: Lonza AGInventors: Walter Brieden, Josef Schröer, Christine Bernegger-Egli, Eva Maria Urban, Michael Petersen, Jean-Paul Roduit, Katja Berchtold, Holger Breitbach
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Publication number: 20040044240Abstract: The invention relates to DMC catalysts which comprise at least 10% by weight, based on the weight of the DMC catalysts, of a crystalline multimetal cyanide compound whose X-ray diffractogram shows sharp reflections at least at the d values ofType: ApplicationFiled: August 28, 2002Publication date: March 4, 2004Inventors: Georg Heinrich Grosch, Edward Bohres, Raimund Ruppel, Kathrin Harre, Eva Baum, Michael Stosser, Jeffery T. Miller, Richard B. Prager
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Patent number: 6683112Abstract: The present invention relates to novel prodrugs of gabapentin and to pharmaceutical formulations and sustained release formulations containing the prodrugs.Type: GrantFiled: October 23, 2001Date of Patent: January 27, 2004Assignee: Andrx CorporationInventors: Chih-Ming Chen, Jane Chen