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)
  • Patent number: 11401227
    Abstract: 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: Grant
    Filed: August 19, 2019
    Date of Patent: August 2, 2022
    Assignee: BASF SE
    Inventors: Frank Bienewald, Martin Voelkert, Rolf Pinkos
  • Patent number: 8796492
    Abstract: 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: Grant
    Filed: March 31, 2010
    Date of Patent: August 5, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Makoto Saito, Hiroko Izumi, Toshimitsu Moriguchi, Tomomasa Kaneko, Atsushi Tachibana, Mitsuaki Makino, Yasuhiro Mimura
  • Publication number: 20130261342
    Abstract: 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: Application
    Filed: December 14, 2011
    Publication date: October 3, 2013
    Applicant: Dow Global Technologies LLC
    Inventors: John R. Briggs, Jasson T. Patton, Daryoosh Beigzadeh, Peter M. Margl, Henk Hagen, Sonet Vermaire-Louw
  • Publication number: 20110213186
    Abstract: 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: Application
    Filed: August 7, 2008
    Publication date: September 1, 2011
    Applicant: Saipem S.P.A.
    Inventors: Marco Di Girolamo, Maura Brianti, Massimo Conte
  • Patent number: 7977520
    Abstract: 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: Grant
    Filed: August 23, 2005
    Date of Patent: July 12, 2011
    Assignee: EVONIX OXENO GmbH
    Inventors: Cornelia Borgmann, Dirk Roettger, Dagmara Ortmann, Reiner Bukohl, Stephan Houbrechts, Franz Nierlich
  • Publication number: 20100249465
    Abstract: 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: Application
    Filed: March 23, 2010
    Publication date: September 30, 2010
    Applicant: MARUZEN PETROCHEMICAL CO., LTD.
    Inventors: Ryuichi TENJIMBAYASHI, Ichiro Kimura
  • Patent number: 7759528
    Abstract: 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: Grant
    Filed: December 11, 2007
    Date of Patent: July 20, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Renaud Cadours, Alain Forestiere, Christophe Vallee
  • Patent number: 7732646
    Abstract: 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: Grant
    Filed: January 3, 2005
    Date of Patent: June 8, 2010
    Assignee: Daiso Co., Ltd.
    Inventors: Shin-ichiro Nakamura, Yasumi Shimizu, Tohru Matsutomi, Thomas Daniel
  • Patent number: 7728180
    Abstract: 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: Grant
    Filed: June 8, 2005
    Date of Patent: June 1, 2010
    Assignee: Kuraray Co., Ltd.
    Inventors: Jin Tokuyasu, Taketoshi Okuno, Takashi Hori, Hideharu Iwasaki
  • Patent number: 7670464
    Abstract: 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: Grant
    Filed: June 8, 2004
    Date of Patent: March 2, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Katrin Klass, Heike Becker, Regina Vogelsang, Alexander Hauk, Markus Siegert, Jochem Henkelmann
  • Publication number: 20080262272
    Abstract: 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: Application
    Filed: June 8, 2005
    Publication date: October 23, 2008
    Applicant: Kuraray Co., Ltd.
    Inventors: Jin Tokuyasu, Taketoshi Okuno, Takashi Hori, Hideharu Iwasaki
  • Publication number: 20080154068
    Abstract: 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: Application
    Filed: December 11, 2007
    Publication date: June 26, 2008
    Inventors: Renaud Cadours, Alain Forestiere, Christophe Vallee
  • Patent number: 7314961
    Abstract: 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: Grant
    Filed: January 20, 2004
    Date of Patent: January 1, 2008
    Assignee: Kuraray Co., Ltd.
    Inventors: Hiroshige Ishino, Hideharu Iwasaki
  • Patent number: 6867307
    Abstract: 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: Grant
    Filed: July 12, 2001
    Date of Patent: March 15, 2005
    Assignee: Adisseo France S.A.S.
    Inventors: Jean-Erick Ancel, Pierre Meilland
  • Patent number: 6835325
    Abstract: 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: Grant
    Filed: April 19, 2002
    Date of Patent: December 28, 2004
    Assignee: Daiso Co., Ltd.
    Inventors: Shin-ichiro Nakamura, Yasumi Shimizu, Tohru Matsutomi
  • Publication number: 20040249222
    Abstract: 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: Application
    Filed: July 19, 2004
    Publication date: December 9, 2004
    Inventor: Thomas Zwieg
  • Publication number: 20040210093
    Abstract: 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 a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20030229240
    Abstract: 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: Application
    Filed: April 17, 2003
    Publication date: December 11, 2003
    Inventors: Florian Rampf, Hans-Christian Militzer
  • Publication number: 20030212284
    Abstract: 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: Application
    Filed: December 31, 2002
    Publication date: November 13, 2003
    Inventors: Walter Weissensteiner, Thomas Sturm, Felix Spindler
  • Publication number: 20030139632
    Abstract: 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: Application
    Filed: December 16, 2002
    Publication date: July 24, 2003
    Inventors: Outi Krause, Reetta Karinen, Juhani Aittamaa
  • Publication number: 20030130544
    Abstract: Process for the telomerization of a conjugated diene,
    Type: Application
    Filed: November 4, 2002
    Publication date: July 10, 2003
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerald Pringle, Renata Helena van der Made
  • Publication number: 20030105306
    Abstract: 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: Application
    Filed: May 21, 2002
    Publication date: June 5, 2003
    Inventors: Robert H. Grubbs, F. Dean Toste
  • Patent number: 6573411
    Abstract: 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: Grant
    Filed: May 16, 2002
    Date of Patent: June 3, 2003
    Assignee: Ausimont S.p.A.
    Inventors: Antonio Russo, Claudio Tonelli
  • Patent number: 6548714
    Abstract: 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: Grant
    Filed: January 24, 2001
    Date of Patent: April 15, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Georg Heinrich Grosch, Harald Larbig, Reinhard Lorenz, Dieter Junge, Kathrin Harre
  • Patent number: 6531635
    Abstract: Processes for the preparation of 3-alkoxyalkanols useful as solvents for coating materials, photoresists, or the like.
    Type: Grant
    Filed: November 19, 2001
    Date of Patent: March 11, 2003
    Assignee: Idemitsu Petrochemicals Co., Ltd.
    Inventors: Toshihide Yoshitome, Hiroshi Kawasaki, Naoya Kawano
  • Patent number: 6525228
    Abstract: 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: Grant
    Filed: October 22, 2001
    Date of Patent: February 25, 2003
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Yves Chauvin, Lionel Magna, Gerald Peter Niccolai, Jean-Marie Basset
  • Patent number: 6504064
    Abstract: 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: Grant
    Filed: June 21, 2001
    Date of Patent: January 7, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochem Henkelmann, Heike Becker, Juan Aiscar, Boris A. Trofimov, Nina K. Gusarova, Ludmilla A. Oparina
  • Patent number: 6329555
    Abstract: 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: Grant
    Filed: November 2, 1999
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Maik Aron, Ralf Böhling, Peter Zehner
  • Patent number: 6271423
    Abstract: 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: Grant
    Filed: December 8, 1999
    Date of Patent: August 7, 2001
    Assignee: BASF Aktiengesellschaft
    Inventor: Jürgen Dahlhaus
  • Patent number: 6235944
    Abstract: 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: Grant
    Filed: January 21, 1999
    Date of Patent: May 22, 2001
    Assignee: Creanova Inc.
    Inventors: Thomas V. John, Chitoor S. Subramaniam, Zheng Wang, Richard J. Kucera, Jr.
  • Patent number: 5609654
    Abstract: 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: Grant
    Filed: May 31, 1995
    Date of Patent: March 11, 1997
    Assignee: Mobil Oil Corporation
    Inventors: Quang N. Le, Robert T. Thomson
  • Patent number: 5600045
    Abstract: 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: Grant
    Filed: December 2, 1993
    Date of Patent: February 4, 1997
    Assignee: The Dow Chemical Company
    Inventors: Matheus J. Van Der Aalst, Levien J. Everaert, Juan M. Garces
  • Patent number: 5489719
    Abstract: 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: Grant
    Filed: June 6, 1994
    Date of Patent: February 6, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Quang N. Le, Robert T. Thomson
  • Patent number: 5473105
    Abstract: 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: Grant
    Filed: October 4, 1994
    Date of Patent: December 5, 1995
    Assignee: UOP
    Inventors: Terry L. Marker, Robert J. Schmidt, Richard E. Marinangeli, Allyn T. Gilbert
  • Patent number: 5393867
    Abstract: 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: Grant
    Filed: January 18, 1994
    Date of Patent: February 28, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Falling: Stephen N.
  • Patent number: 5210324
    Abstract: 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: Grant
    Filed: October 11, 1989
    Date of Patent: May 11, 1993
    Assignee: Allied Colloids Limited
    Inventors: David Farrar, Malcolm Hawe
  • Patent number: 5120868
    Abstract: 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: Grant
    Filed: March 28, 1991
    Date of Patent: June 9, 1992
    Assignee: Snamprogetti S.p.A.
    Inventors: Renata Patrini, Mario Marchionna, Massimo Lami, Francesco Ancillotti
  • Patent number: 4843180
    Abstract: 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: Grant
    Filed: June 21, 1988
    Date of Patent: June 27, 1989
    Assignee: The Dow Chemical Company
    Inventor: Michael J. Mullins
  • Patent number: 4721820
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: January 26, 1988
    Assignee: National Distillers and Chemical Corporation
    Inventor: Ronnie M. Hanes
  • Patent number: 4590300
    Abstract: 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: Grant
    Filed: January 9, 1985
    Date of Patent: May 20, 1986
    Assignee: The Dow Chemical Company
    Inventors: Michael J. Mullins, Percy J. Hamlin
  • Patent number: 4503275
    Abstract: 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: Grant
    Filed: September 16, 1983
    Date of Patent: March 5, 1985
    Assignee: Davy McKee (London) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4442042
    Abstract: 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: Grant
    Filed: April 30, 1981
    Date of Patent: April 10, 1984
    Assignee: Mobil Oil Corporation
    Inventor: Kirk D. Schmitt
  • Patent number: 4338469
    Abstract: 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: Grant
    Filed: December 22, 1977
    Date of Patent: July 6, 1982
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, Peter Hosler
  • Patent number: 4311862
    Abstract: 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: Grant
    Filed: July 24, 1980
    Date of Patent: January 19, 1982
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4302394
    Abstract: 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: Grant
    Filed: April 11, 1980
    Date of Patent: November 24, 1981
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventor: Alan J. Dennis
  • Patent number: 4292219
    Abstract: 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: Grant
    Filed: December 10, 1979
    Date of Patent: September 29, 1981
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, Peter Hosler
  • Patent number: 4261839
    Abstract: 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: Grant
    Filed: March 19, 1979
    Date of Patent: April 14, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rolf Kleber, Siegfried Billenstein
  • Patent number: 4262145
    Abstract: 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: Grant
    Filed: December 10, 1979
    Date of Patent: April 14, 1981
    Assignee: Gulf Research & Development Company
    Inventors: Charles M. Selwitz, John G. McNulty
  • Patent number: 4256465
    Abstract: 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: Grant
    Filed: July 20, 1979
    Date of Patent: March 17, 1981
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Tetsuya Takezono, Yasuo Fujiwara
  • Patent number: 4219677
    Abstract: 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: Grant
    Filed: July 19, 1978
    Date of Patent: August 26, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Emile Kuntz