Preparing By Reacting An Acyclic Ethylenically Unsaturated Compound And An Organic Hydroxy Containing Compound (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/689)
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Patent number: 11401227Abstract: A process produces a mono vinyl ether, R—O—CH?CH2. R represents an organic group with at least three carbon atoms. The process involves reacting a mono hydroxy compound. R—OH, with acetylene in presence of a catalyst to get a product mixture containing the mono vinyl ether, unconverted mono hydroxy compound, and the catalyst. To the product mixture, an ester is added that contains at least one ester group, X—O2C—. X is a hydrocarbon group containing less carbon atoms than R. The remaining mono hydroxy compound R—OH is reacted with the ester in the presence of the catalyst to get a transesterification product containing at least one ester group, R—O2C—, and an alcohol, X—OH. The mono vinyl ether is isolated from the product mixture obtained after the ester addition, optionally followed by purification of the mono vinyl ether by distillation.Type: GrantFiled: August 19, 2019Date of Patent: August 2, 2022Assignee: BASF SEInventors: Frank Bienewald, Martin Voelkert, Rolf Pinkos
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Patent number: 8796492Abstract: An ?-(unsaturated alkoxyalkyl)acrylate composition is provided which enables an ?-(unsaturated alkoxyalkyl)acrylate product to be stored at a high purity for an extended period of time and can fully suppress problems such as discoloration and gelation from arising during polymerization, and a method of safely preparing ?-(unsaturated alkoxyalkyl)acrylate compositions industrially, with high purity. The composition includes an ?-(unsaturated alkoxyalkyl)acrylate of a specific structure and an antioxidant, the content of the antioxidant being from 0.03 to 0.5 wt % per 100 wt % of the ?-(unsaturated alkoxyalkyl)acrylate.Type: GrantFiled: March 31, 2010Date of Patent: August 5, 2014Assignee: Nippon Shokubai Co., Ltd.Inventors: Makoto Saito, Hiroko Izumi, Toshimitsu Moriguchi, Tomomasa Kaneko, Atsushi Tachibana, Mitsuaki Makino, Yasuhiro Mimura
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Publication number: 20130261342Abstract: A process for the telomerization of butadiene comprises reacting 1,3-butadiene and an alkanol, in the presence of a catalyst promoter and an alkoxydimerization catalyst comprising a Group VIII transition metal and a triarylphosphine ligand, which includes one phenyl that is mono-ortho-alkoxy substituted and at least one other phenyl including at least one substituent that withdraws electrons from the phosphorus atom. The product includes an alkoxy-substituted octadiene, which may then be used to produce 1-octene. The catalyst shows improved stability, activity and selectivity toward the alkoxy-substituted octadiene.Type: ApplicationFiled: December 14, 2011Publication date: October 3, 2013Applicant: Dow Global Technologies LLCInventors: John R. Briggs, Jasson T. Patton, Daryoosh Beigzadeh, Peter M. Margl, Henk Hagen, Sonet Vermaire-Louw
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Publication number: 20110213186Abstract: A tubular reactor is described, for catalytic reactions involving thermal exchanges, in particular for etherification reactions between branched olefins and linear alcohol, for dimerization reactions of branched olefins or cracking reactions, essentially consisting of a vertical tube-bundle exchanger whose tubes contain catalyst, having inlet and outlet nozzles for each passage side of the reagents, catalyst and thermal exchange liquid, characterized in that it has one or more metallic supports situated outside the lower tube plate in the lower part of the reactor for sustaining the catalyst so that the same catalyst is contained not only in the tubes of the tube-bundle but also in said lower part outside the lower tube plate and also in the upper part outside the upper tube plate.Type: ApplicationFiled: August 7, 2008Publication date: September 1, 2011Applicant: Saipem S.P.A.Inventors: Marco Di Girolamo, Maura Brianti, Massimo Conte
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Patent number: 7977520Abstract: Process for telomerizing noncyclic olefins having at least two conjugated double bonds with at least one nucleophile using a catalyst containing a metal of group 8, 9 or 10 of the Periodic Table of the Elements, wherein the overall telomerization process has a process step of catalyst recycling, in which hydrogen is added via a hydrogen source to the mixture present in this process step.Type: GrantFiled: August 23, 2005Date of Patent: July 12, 2011Assignee: EVONIX OXENO GmbHInventors: Cornelia Borgmann, Dirk Roettger, Dagmara Ortmann, Reiner Bukohl, Stephan Houbrechts, Franz Nierlich
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Publication number: 20100249465Abstract: A process for producing a high-purity vinyl ether, which comprises: a step of subjecting an alcohol represented by the general formula (1) R—O—H??(1) to a vinyl ether formation reaction in the presence of a catalyst to synthesize a vinyl ether represented by the general formula (2), R—O—CH?CH2??(2) a step of removing the catalyst from the reaction mixture obtained in the above step to obtain a crude vinyl ether containing the vinyl ether and the unreacted raw material alcohol, a step of reacting the unreacted raw material alcohol in the crude vinyl ether, with the vinyl ether in the presence of an acid catalyst, to convert the alcohol into an acetal represented by the general formula (3), and a step of subjecting a crude vinyl ether containing the acetal (III) to distillation to obtain a high-purity vinyl ether.Type: ApplicationFiled: March 23, 2010Publication date: September 30, 2010Applicant: MARUZEN PETROCHEMICAL CO., LTD.Inventors: Ryuichi TENJIMBAYASHI, Ichiro Kimura
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Patent number: 7759528Abstract: An enhanced ether production process from an olefinic cut containing at least one iso-olefin and from an alcohol comprises a stage of removal of the acetonitrile present in the hydrocarbon feed by liquid-liquid extraction, the extraction solvent being a non-aqueous ionic liquid of general formula Q+A?, wherein Q+ is an ammonium, phosphonium and/or sulfonium cation, and A? an anion likely to form a liquid salt with said cation. Advantageously, the method according to the invention generally allows the amount of water at the etherification reactor inlet to be divided by at least two and thus the purity of the ether produced to be improved.Type: GrantFiled: December 11, 2007Date of Patent: July 20, 2010Assignee: Institut Francais du PetroleInventors: Renaud Cadours, Alain Forestiere, Christophe Vallee
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Patent number: 7732646Abstract: An allyl type crosslinking agent for use in production of a super water-absorbent polymer comprising a polymerizable compound having a carbon-carbon double bond or a salt thereof. The crosslinking agent comprises a linear hydroxypolyallyl ether having at least one hydroxyl group and at least two allyl groups obtained by allyletherification of hydroxyl groups in a linear polyol compound selected from the group consisting of erythritol, xylitol and sorbitol. This allyl type crosslinking agent is highly soluble in an aqueous solvent, and can give an excellent super water-absorbent polymer, which cannot be obtained in the prior arts, having high levels of both of water absorptivity under atmospheric pressure and water absorptivity under pressurized conditions.Type: GrantFiled: January 3, 2005Date of Patent: June 8, 2010Assignee: Daiso Co., Ltd.Inventors: Shin-ichiro Nakamura, Yasumi Shimizu, Tohru Matsutomi, Thomas Daniel
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Patent number: 7728180Abstract: A method for producing ethers comprises the following steps: initiating telomerization process of a conjugated diene compound with an hydroxyl compound represented by the following formula (I): R1OH??(I) in the presence of a palladium compound, a tertiary isocyanide represented by the following formula (II): R2NC??(II), and a base; and adding halfway through the telomerization process a tertiary phosphine represented by the following formula (III): PR3R4R5??(III) (the respective symbols are defined in the description).Type: GrantFiled: June 8, 2005Date of Patent: June 1, 2010Assignee: Kuraray Co., Ltd.Inventors: Jin Tokuyasu, Taketoshi Okuno, Takashi Hori, Hideharu Iwasaki
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Patent number: 7670464Abstract: Process for distillatively separating a mixture containing a vinyl ether of the general formula (I) R1—O—CH?CH2??(I) and alcohol of the general formula (II) R2—OH??(II) in which R1 and R2 are each independently a saturated or unsaturated, aliphatic or cycloaliphatic radical having from 2 to 10 carbon atoms, and in which the alcohol (II) has a boiling point which is at least 1° C. higher, measured at or extrapolated to 0.1 MPa abs, than the vinyl ether (I), by a) passing the mixture into a first distillation column and withdrawing, as a top product, an azeotrope containing vinyl ether (I) and alcohol (II) and, as a bottom product, a stream enriched with the alcohol (II); b) passing the azeotrope containing vinyl ether (I) and alcohol (II) from the first distillation column into a second distillation column which is operated at a pressure which is from 0.Type: GrantFiled: June 8, 2004Date of Patent: March 2, 2010Assignee: BASF AktiengesellschaftInventors: Katrin Klass, Heike Becker, Regina Vogelsang, Alexander Hauk, Markus Siegert, Jochem Henkelmann
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Publication number: 20080262272Abstract: A method for producing ethers comprises the following steps: initiating telomerization process of a conjugated diene compound with an hydroxyl compound represented by the following formula (I): R1OH ??(I) in the presence of a palladium compound, a tertiary isocyanide represented by the following formula (II): R2NC ??(II) , and a base; and adding halfway through the telomerization process a tertiary phosphine represented by the following formula (III): PR3R4R5 ??(III) (the respective symbols are defined in the description).Type: ApplicationFiled: June 8, 2005Publication date: October 23, 2008Applicant: Kuraray Co., Ltd.Inventors: Jin Tokuyasu, Taketoshi Okuno, Takashi Hori, Hideharu Iwasaki
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Publication number: 20080154068Abstract: An enhanced ether production process from an olefinic cut containing at least one iso-olefin and from an alcohol comprises a stage of removal of the acetonitrile present in the hydrocarbon feed by liquid-liquid extraction, the extraction solvent being a non-aqueous ionic liquid of general formula Q+A?, wherein Q+ is an ammonium, phosphonium and/or sulfonium cation, and A? an anion likely to form a liquid salt with said cation. Advantageously, the method according to the invention generally allows the amount of water at the etherification reactor inlet to be divided by at least two and thus the purity of the ether produced to be improved.Type: ApplicationFiled: December 11, 2007Publication date: June 26, 2008Inventors: Renaud Cadours, Alain Forestiere, Christophe Vallee
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Patent number: 7314961Abstract: According to the present invention, a method of producing ethers, which includes subjecting a conjugated diene compound and an alcohol to a telomerization reaction in the presence of a composition containing a palladium compound, an isocyanide represented by the formula (I) R1R2R3CNC ??(I) and a base represented by the formula (II) M(OR4)n ??(II) as a catalyst is provided. According to the method of the present invention, by telomerization reaction of a conjugated diene compound and an alcohol, ethers can be produced industrially advantageously. (In the above-mentioned formulas, each symbol is as defined in the specification.Type: GrantFiled: January 20, 2004Date of Patent: January 1, 2008Assignee: Kuraray Co., Ltd.Inventors: Hiroshige Ishino, Hideharu Iwasaki
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Patent number: 6867307Abstract: Intermediate compounds which can be used in the preparation of phytone and Vitamin E, a process for the preparation thereof, and a process for the preparation of phytone and Vitamin E from these intermediate compounds.Type: GrantFiled: July 12, 2001Date of Patent: March 15, 2005Assignee: Adisseo France S.A.S.Inventors: Jean-Erick Ancel, Pierre Meilland
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Patent number: 6835325Abstract: A crosslinking agent containing a polyallyl ether compound having at least one hydroxyl group derived from a glycidyl group and at least two allyl groups can be used for the production of a highly water-absorbing polymer comprising a polymerizable compound having a carbon-carbon double bond or a salt thereof, has a high solubility in aqueous solution of the monomer and gives a highly water-absorbing polymer having water absorptivity required at practical levels.Type: GrantFiled: April 19, 2002Date of Patent: December 28, 2004Assignee: Daiso Co., Ltd.Inventors: Shin-ichiro Nakamura, Yasumi Shimizu, Tohru Matsutomi
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Publication number: 20040249222Abstract: Heterogeneous surface with polar functional groups as nucleation points. These nucleation points cause precipitation of a substance, for example ice or salt, in a fluid at these nucleation points under suitable physical conditions because the Gibbs free energy of the system is lower at the nucleation points than between the nucleation points, where said system comprises said surface and said fluid with said substance near said surface.Type: ApplicationFiled: July 19, 2004Publication date: December 9, 2004Inventor: Thomas Zwieg
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Publication number: 20040210093Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first aType: ApplicationFiled: May 5, 2004Publication date: October 21, 2004Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventors: Willibrord A. Groten, Mario J. Maraschino
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Publication number: 20030229240Abstract: The invention relates to a process for synthesizing tertiary phosphines by reacting halophosphines with organomagnesium compounds in the presence of copper compounds and optionally of salts.Type: ApplicationFiled: April 17, 2003Publication date: December 11, 2003Inventors: Florian Rampf, Hans-Christian Militzer
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Publication number: 20030212284Abstract: Compounds of the formula (I) and (Ia) in the form of racemates, mixtures of diastereomers or in essentially enantiomerically pure form, (I), (Ia), where R is hydrogen, C1-C8alkyl, C5-C12cycloakyl, phenyl or phenyl substituted by from 1 to 3 C1-C4alky or C1-C4alkoxy groups; n is 0 or an integer from 1 to 4 and R1 are identical or different subtitutuents selected from the group consisting of C1-C4alkyl, C1-C4fluoroalkyl and C1-C4alkoxy; X1 and X2 are each, indenpendently of one another, secondary phosphino; T is C6-C20arylene or C3-C16heteroarylene; and X2 is bound in the ortho position relative to the T-cyclopenitadienyl bond.Type: ApplicationFiled: December 31, 2002Publication date: November 13, 2003Inventors: Walter Weissensteiner, Thomas Sturm, Felix Spindler
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Publication number: 20030139632Abstract: This invention concerns a process and an apparatus for producing ether and the use of a dimerised reaction product as the olefinic feedstock in etherification. According to the present process alcohol and C8-C12 olefin(s) are fed to a first reaction zone (21-25) comprising at least one reactor, the olefin(s) and alcohol are subjected to an etherification reaction in the presence of an acidic catalyst. The effluent from the first reaction zone (21-25) is fed to a fractionation zone (26). From the fractionation zone (26) is withdrawn a side-flow which is conducted either back to the first reaction zone (21-25) or to a second reaction zone. The effluent of the first reaction zone (21-25) or the second reaction zone is circulated back to the fractionation zone (26), and the ether is recovered from the fractionation zone (26).Type: ApplicationFiled: December 16, 2002Publication date: July 24, 2003Inventors: Outi Krause, Reetta Karinen, Juhani Aittamaa
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Publication number: 20030130544Abstract: Process for the telomerization of a conjugated diene,Type: ApplicationFiled: November 4, 2002Publication date: July 10, 2003Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerald Pringle, Renata Helena van der Made
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Publication number: 20030105306Abstract: Methods are provided for carrying out nucleophilic addition reactions using oxo, sulfido or amido complexes of transition metals as reaction catalysts. Exemplary catalysts are oxo complexes of Group 7 transition metals, with rhenium (V) oxo complexes, including dioxo complexes, preferred. Nucleophilic addition reactions that can be catalyzed using the present methods include silylation, hydrosilylation, hydroamination, silylmetalation, carbometalation, aldol reactions, hydro- and carbometalation initiated cyclization/polymerization, and epoxide/aziridine opening. The invention also pertains to novel transition metal complexes that have utility in catalyzing such reactions.Type: ApplicationFiled: May 21, 2002Publication date: June 5, 2003Inventors: Robert H. Grubbs, F. Dean Toste
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Patent number: 6573411Abstract: A process to obtain fluoropolyoxyalkylenes having the structure: T—O—(CF2CF(CF3)O)n−1—(CF(CF3)O)m—CF2—CH2OH (I) wherein: T=C1-C3 perfluoroalkyl containing one Cl atom; n=an integer from 1 to 15; m/n=0-0.5, m+n such to have a number molecular weight in the range 280-4,000; said process comprising: a) the gradual addition of a metal hydride in admixture with a solvent to an ester precursor having the structure T—O—(CF2CF(CF3)O)n−1—(CF(CF3)O)m—CF2—COOR (II) wherein R=C1-C20 alkyl, or aromatic, cycloalkyl or heterocyclic residue, b) the hydrolysis of the reaction mixture obtained in step a) with an aqueous acid solution, the subsequent separation from the obtained organic phase of the compounds of structure (I).Type: GrantFiled: May 16, 2002Date of Patent: June 3, 2003Assignee: Ausimont S.p.A.Inventors: Antonio Russo, Claudio Tonelli
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Patent number: 6548714Abstract: A process for preparing polyetherols by ring-opening polymerization of alkylene oxides onto H-functional initiator molecules comprises at least one process step a) in which a compound of the formula (I) M′aM″b(OH)cOd* Ae*Lf (I), is applied to a solid inert support or incorporated in the latter or molded to form a shaped body is used as catalyst, and at least one process step b) in which a multimetal cyanide compound of the formula (II) M1a[M2(CN)b(A)c]d·fM1gXn·h(H20) eL (II) is applied to a solid, inert support or incorporated in the latter or molded to form a shaped body or in powder or paste form is used as catalyst.Type: GrantFiled: January 24, 2001Date of Patent: April 15, 2003Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Harald Larbig, Reinhard Lorenz, Dieter Junge, Kathrin Harre
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Patent number: 6531635Abstract: Processes for the preparation of 3-alkoxyalkanols useful as solvents for coating materials, photoresists, or the like.Type: GrantFiled: November 19, 2001Date of Patent: March 11, 2003Assignee: Idemitsu Petrochemicals Co., Ltd.Inventors: Toshihide Yoshitome, Hiroshi Kawasaki, Naoya Kawano
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Patent number: 6525228Abstract: The present invention is related to a process for telomerizing a conjugated diene which comprises reacting said conjugated diene with a compound containing active hydrogen in the presence of a catalyst system comprising at least one transition metal compound, at least one phosphorus-containing compound, and at least one salt which forms a liquid under the conditions of the telomerization process.Type: GrantFiled: October 22, 2001Date of Patent: February 25, 2003Assignee: Celanese Chemicals Europe GmbHInventors: Yves Chauvin, Lionel Magna, Gerald Peter Niccolai, Jean-Marie Basset
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Patent number: 6504064Abstract: Enol ethers of the formula (I) where R1 to R3 are each, independently of one another, hydrogen or a carbon-containing organic radical and R4 is an unsubstituted or substituted alkyl radical, are prepared by reacting alcohols of the formula (II) R4—OH (II), with alkynes of the formula (IlIa), alkadienes of the formula (IIIb) R1—C≡C—CHR2R3 (IIIa), R1—CH═C═CR2R3 (IIIb) or mixtures thereof, where R1 to R4 are as defined above, in the presence of an alkali metal alkoxide and a polar, aprotic solvent.Type: GrantFiled: June 21, 2001Date of Patent: January 7, 2003Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Heike Becker, Juan Aiscar, Boris A. Trofimov, Nina K. Gusarova, Ludmilla A. Oparina
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Patent number: 6329555Abstract: Described is a process for preparing substituted butenes of the formula I and/or II, where the radical R is unsubstituted or mono- or di-C1-C10-alkoxy-substituted or mono- or dihydroxy-substituted C2-C20-alkyl or alkenyl or is C6-C10-aryl, C7-C11-aralkyl or methyl by reacting 1,3-butadiene with an alcohol of the formula ROH in which R is as defined in the presence of an acidic particulate catalyst insoluble in the reaction medium, which involves contacting the butadiene, the alcohol and the catalyst in a fluidized bed reactor which is flow-approached from below and is operated at above the loosening point.Type: GrantFiled: November 2, 1999Date of Patent: December 11, 2001Assignee: BASF AktiengesellschaftInventors: Maik Aron, Ralf Böhling, Peter Zehner
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Patent number: 6271423Abstract: A process for preparing butenyl ethers of the formula I CH3—CH═CH—CH2—OR I by reacting butadiene or butadiene-containing hydrocarbon streams with alcohols of the formula II ROH II at elevated temperature and superatmospheric pressure in the presence of transition metal complexes containing ligands of compounds of elements of group V of the Periodic Table of the Elements to form an isomer mixture of butenyl ethers of the formula I and butenyl ethers of the formula III CH2═CH—CH(OR)—CH3 III and, optionally, isomerizing the butenyl ethers of the formula III to butenyl ethers of the formula I, where R is as defined in the specification and the catalyst used is a complex of a transition metal of group VIII of the Periodic Table of the Elements with ligands of the formula IV where M is an iron, cobalt, nickel, or ruthenium atom, X is a bridge and where n, y and R1-R6 are as defined in the specification.Type: GrantFiled: December 8, 1999Date of Patent: August 7, 2001Assignee: BASF AktiengesellschaftInventor: Jürgen Dahlhaus
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Patent number: 6235944Abstract: The present invention relates to a general synthesis for producing secondaryalkoxy-1-alkenes in commercial quantities in good yields by reacting cyclic and acyclic ketones and the corresponding alcohol with a secondary alkyl orthoformate ester in the presence of an acid catalyst, a Lewis acid, ferric chloride being preferred, and recovering the produce as a liquid of high purity.Type: GrantFiled: January 21, 1999Date of Patent: May 22, 2001Assignee: Creanova Inc.Inventors: Thomas V. John, Chitoor S. Subramaniam, Zheng Wang, Richard J. Kucera, Jr.
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Patent number: 5609654Abstract: A process for production of alkyl tertiary alkyl ethers in C.sub.4 + hydrocarbon streams rich in isoolefins, typically containing catalyst deactivating amounts of dienes and/or compounds containing heteroatoms. The process is especially advantageous in extending the cycle length for the zeolite catalyzed etherification of isoolefins in C.sub.4 + FCC gasoline by reducing catalyst aging. It has been discovered that if hydrogen is cofed with the alkanol and C.sub.4 + isoolefin rich feedstreams to an etherification reaction catalyzed by acidic zeolite wherein the zeolite has been impregnated with a noble metal the rate of catalyst aging or deactivation is substantially lowered. The process is especially effective, i.e., catalyst aging is particularly reduced, when hydrogen is cofed to an etherification reaction using acidic zeolite Beta catalyst containing palladium.Type: GrantFiled: May 31, 1995Date of Patent: March 11, 1997Assignee: Mobil Oil CorporationInventors: Quang N. Le, Robert T. Thomson
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Patent number: 5600045Abstract: A process for conversion of crude hydrocarbon mixtures comprising tertiary olefins and gum-forming constituents with an alcohol in the presence of hydrogen, which process comprises contacting the crude hydrocarbon mixture, the alcohol, and hydrogen with a catalyst comprising an acidic molecular sieve containing an active hydrogenation metal component, as well as a stabilized crude hydrocarbon mixture containing alkyl tertiary alkyl ethers. A process for conversion of a tertiary olefin which contains one or more additional ethylenically or acetylenically unsaturated bonds.Type: GrantFiled: December 2, 1993Date of Patent: February 4, 1997Assignee: The Dow Chemical CompanyInventors: Matheus J. Van Der Aalst, Levien J. Everaert, Juan M. Garces
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Patent number: 5489719Abstract: A process is disclosed for the production of alkyl tertiary alkyl ethers in C.sub.4 + hydrocarbon streams rich in isoolefins, typically containing catalyst deactivating amounts of dienes and/or compounds containing heteroatoms. The process is especially advantageous in extending the cycle length for the zeolite catalyzed etherification of isoolefins in C.sub.4 + FCC gasoline by reducing catalyst aging. It has been discovered that if hydrogen is cofed with the alkanol and C.sub.4 + isoolefin rich feedstreams to an etherification reaction catalyzed by acidic zeolite wherein the zeolite has been impregnated with a noble metal the rate of catalyst aging or deactivation is substantially lowered. The process is especially effective, i.e., catalyst aging is particularly reduced, when hydrogen is cofed to an etherification reaction using acidic zeolite Beta catalyst containing palladium.Type: GrantFiled: June 6, 1994Date of Patent: February 6, 1996Assignee: Mobil Oil CorporationInventors: Quang N. Le, Robert T. Thomson
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Patent number: 5473105Abstract: A process for concurrently producing diisopropyl ether and isopropyl ethyl ether from water, ethanol from an independent source, and propylene, has been developed. The product mixture may be used as a high octane number booster due mainly to the presence of the diisopropyl ether and to a lesser extent, the isopropyl ethyl ether. Furthermore, the product mixture, upon blending with gasoline, incorporates a renewable resource into the gasoline since the isopropyl ethyl ether is produced from ethanol. Optionally, the product mixture may be passed through an acid removal zone to remove acid, if present, before being recycled or further processed. A portion of the product mixture is recycled to the reaction zone to increase the conversion of reactants to products.Type: GrantFiled: October 4, 1994Date of Patent: December 5, 1995Assignee: UOPInventors: Terry L. Marker, Robert J. Schmidt, Richard E. Marinangeli, Allyn T. Gilbert
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Patent number: 5393867Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of a palladium(O) catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, m/(n+m) is greater than 0.30 and up to 0.Type: GrantFiled: January 18, 1994Date of Patent: February 28, 1995Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Falling: Stephen N.
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Patent number: 5210324Abstract: A new process for producing allyl ethers, usually C.sub.8-30 alkyl (CH.sub.2 CH.sub.2 O).sub.5-100 allyl ether, by forming a solution of an alcohol, usually a surfactant alcohol, in a solvent capable of forming an azeotrope with water, azeotroping the mixture to remove substantially all the water, adding an alkalimetal alkoxide, usually sodium methoxide, removing the alkanol formed, usually by azeotroping with the solvent, adding a halide, usually allyl chloride, and recovering the allyl ether. The ethers are useful as monomers, for example to produce polymers by copolymerising with copolymerisable ethylenically unsaturated comonomers for a wide range of applications.Type: GrantFiled: October 11, 1989Date of Patent: May 11, 1993Assignee: Allied Colloids LimitedInventors: David Farrar, Malcolm Hawe
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Patent number: 5120868Abstract: A catalyst system for the selective production of isoprenylalkylethers from isoprene is described, characterized by satisfying the following empirical formulaPdLxL.sup.' ywhereL is a phosphorated binder in the form of an organic derivative of trivalent phosphorus of type R3P or R2P[CH(R)]zPR2, in which the substituents R, which can be identical or different, are either hydrogen atoms or alkyl, cycloalkyl, aryl, alkoxy, aryloxy, arylthio or arylalkyl groups, and in which z is a whole number between 1 and 5;L.sup.' is an easily displaceable binder chosen from dienes, olefins, anhydrides, diketones and nitriles;x is a whole number between 0 and 4 and y is a whole number between 0 and 3,in which system excess phosphorated compounds of R3P or R2P[CH(R)]zPR2 type may or may not be present.Type: GrantFiled: March 28, 1991Date of Patent: June 9, 1992Assignee: Snamprogetti S.p.A.Inventors: Renata Patrini, Mario Marchionna, Massimo Lami, Francesco Ancillotti
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Patent number: 4843180Abstract: Conjugated diolefins such as 1,3-butadiene are converted to ethers by reaction with aliphatic hydroxyl-containing compounds such as ethylene glycol in the presence of a chelating phosphine adduct of zero valent nickel. A preferred chelating phosphine ligand is 1,2-bis(diphenylphosphino)ethane.Type: GrantFiled: June 21, 1988Date of Patent: June 27, 1989Assignee: The Dow Chemical CompanyInventor: Michael J. Mullins
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Patent number: 4721820Abstract: A process for isomerizing allylic ethers is disclosed. In this process a compound having the structural formulaCH.sub.2 .dbd.CH--CH(OR)--R.sup.1where R is hydrocarbyl; and R.sup.1 is an organo group is contacted with a hydroxy-containing compound and a catalytically effective amount of a catalyst selected from the group consisting of cupric chloride, cupric bromide, a mixture of cupric chloride and palladium chloride, a mixture of cupric chloride and palladium bromide, a mixture of cupric bromide and palladium chloride and a mixture of cupric bromide and palladium bromide whereby a compound having the structural formulaRO--CH.sub.2 --CH.dbd.CH--R.sup.1where R and R.sup.1 have the meanings given above is formed.Type: GrantFiled: December 22, 1986Date of Patent: January 26, 1988Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4590300Abstract: Allyl methyl ethers are transetherified with alcohols by use of a catalyst of a solid acid that contains no mercury or cuprous salt catalyst.Type: GrantFiled: January 9, 1985Date of Patent: May 20, 1986Assignee: The Dow Chemical CompanyInventors: Michael J. Mullins, Percy J. Hamlin
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Patent number: 4503275Abstract: Butane-1,4-diol is produced by converting allyl alcohol to an allyl t-alkyl or -cycloalkyl ether of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.Type: GrantFiled: September 16, 1983Date of Patent: March 5, 1985Assignee: Davy McKee (London) LimitedInventors: Norman Harris, Alan J. Dennis, George E. Harrison
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Patent number: 4442042Abstract: An improved process for making propane sulfonates without isolating intermediates is provided comprising using an aqueous NaOH system instead of metallic sodium and recycling a portion of the product phase transfer as catalyst.Type: GrantFiled: April 30, 1981Date of Patent: April 10, 1984Assignee: Mobil Oil CorporationInventor: Kirk D. Schmitt
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Patent number: 4338469Abstract: In the acid-catalyzed etherification of olefins with alcohols, substantially complete recovery of alcohol and catalyst is obtained when small amounts of water (1-10%) are added to the reaction. The addition of water provides a two-phase reaction medium in which olefin and ether are in the upper phase and alcohol and catalyst are in the lower phase. These phase are maintained during the course of the reaction, which continues as a two-phase system.Certain novel ethers produced by this process are likewise disclosed herein.Type: GrantFiled: December 22, 1977Date of Patent: July 6, 1982Assignee: Suntech, Inc.Inventors: James E. Lyons, Peter Hosler
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Patent number: 4311862Abstract: Process for the preparation of olefinically unsaturated ethers by reacting a conjugated diene and a lower alkanol with the aid of an acidic catalyst in the presence of a non-basic aprotic polar solvent. The olefinically unsaturated ethers are of interest as solvents and gasoline additives and can also be used as starting materials for e.g. the synthesis of ketones.Type: GrantFiled: July 24, 1980Date of Patent: January 19, 1982Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4302394Abstract: Butyrolactone is produced by oxidizing an aldehyde-ether of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, to form an acid ether of the general formula: ##STR2## followed by deetherification, dehydration and cyclization. Oxidation can be carried out with e.g. gaseous oxygen. Deetherification can be accomplished by contact with an acid catalyst, while cyclization may occur spontaneously. A cyclic process is described in which allyl alcohol is converted by reaction with a suitable olefin, e.g.Type: GrantFiled: April 11, 1980Date of Patent: November 24, 1981Assignee: Davy McKee (Oil & Chemicals) LimitedInventor: Alan J. Dennis
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Patent number: 4292219Abstract: In the acid-catalyzed etherification of olefins with alcohols, substantially complete recovery of alcohol and catalyst is obtained when small amounts of water (1-10%) are added to the reaction. The addition of water provides a two-phase reaction medium in which olefin and ether are in the upper phase and alcohol and catalyst are in the lower phase. These phases are maintained during the course of the reaction, which continues as a two-phase system. Certain novel ethers produced by this process are likewise disclosed herein.Type: GrantFiled: December 10, 1979Date of Patent: September 29, 1981Assignee: Suntech, Inc.Inventors: James E. Lyons, Peter Hosler
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Patent number: 4261839Abstract: A fiber preparation containing or consisting of a tertiary butyl ether of the general formula ##STR1## in which R.sub.1 is a straight-chain or branched C.sub.12 -C.sub.22 -alkyl or alkenyl group.Type: GrantFiled: March 19, 1979Date of Patent: April 14, 1981Assignee: Hoechst AktiengesellschaftInventors: Rolf Kleber, Siegfried Billenstein
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Patent number: 4262145Abstract: A process for converting an olefin, or a mixture of olefins, to an ether, or a mixture of ethers, which comprises reacting said olefin, or said mixture of olefins, with an alkanol in contact with silicatungstic acid.Type: GrantFiled: December 10, 1979Date of Patent: April 14, 1981Assignee: Gulf Research & Development CompanyInventors: Charles M. Selwitz, John G. McNulty
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Patent number: 4256465Abstract: A method for producing methyl tert-butyl ether which comprises the steps of: allowing isobutylene-containing hydrocarbon and methyl alcohol in a given molar ratio to react at a given temperature, pressure and liquid space velocity in the presence of strongly acidic cation-exchange resin catalyst; then passing the reaction product through a fixed bed filled with a water-insoluble, solid particulate acid-neutralizing agent; and subjecting the effluent to flashing operation, preferably also to rectification, to obtain methyl tert-butyl ether. Further included in the invention is the preparation of a fuel composition by mixing the thus obtained methyl tert-butyl ether into an internal combustion fuel.Type: GrantFiled: July 20, 1979Date of Patent: March 17, 1981Assignee: Nippon Oil Co., Ltd.Inventors: Tetsuya Takezono, Yasuo Fujiwara
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Patent number: 4219677Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: July 19, 1978Date of Patent: August 26, 1980Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz