Noble Metal Containing Catalyst Utilized Patents (Class 568/690)
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Patent number: 10626072Abstract: The present invention relates to a method of preparing methyl tert-butyl ether including a reaction step of reacting methanol with iso-butene in the presence of an acid catalyst to generate methyl tert-butyl ether; and a purification step of purify the reaction product obtained by the reaction step by introducing the reaction product into a reaction distillation column including a packing stage containing an acid catalyst, wherein a flow ratio of a recycle to a fresh feed is different per the volume of each reactor. Accordingly, the amount of unreacted iso-butene and the amount of impurities included in the reactor may be reduced, resulting in reduction of the amount of thermal energy used in a reaction distillation column.Type: GrantFiled: January 4, 2018Date of Patent: April 21, 2020Assignee: LG CHEM, LTD.Inventors: Sung Ho Lee, Sang Beom Lee, Joon Ho Shin, In Yong Jeong
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Patent number: 8558030Abstract: In an improved process for telomerizing butadiene, contact butadiene and an organic hydroxy compound represented by formula ROH (I), wherein R is a substituted or unsubstituted C1-C20-hydrocarbyl and the organic hydroxy compound is not glycerol, in a reaction fluid in the presence of a palladium catalyst and a phosphine ligand represented by formula PAr3 (II), wherein each Ar is independently a substituted or unsubstituted aryl having a hydrogen atom on at least one ortho position, at least two Ar groups are ortho-hydrocarbyloxyl substituted aryls. The phosphine ligand has a total of two (2), three (3), four (4), five (5), or six (6) substituted or unsubstituted C1-C20-hydrocarbyloxyls, and optionally, any two adjacent substituents on an Ar group can be bonded to form a 5- to 7-membered ring.Type: GrantFiled: July 22, 2009Date of Patent: October 15, 2013Assignee: Dow Global Technologies LLCInventors: John R. Briggs, Jasson T. Patton, Sonet Vermaire-Louw, Peter M. Margl, Henk Hagen, Daryoosh Beigzadeh
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Patent number: 8269050Abstract: The invention relates to a process for preparing ETBE from technical mixtures which comprise at least 1-butene, isobutene, n-butane and 2-butenes, by reacting the isobutene present, distillatively removing a fraction comprising 1-butene and isobutene and again reacting the isobutene present therein to give ETBE.Type: GrantFiled: December 21, 2006Date of Patent: September 18, 2012Assignee: Evonik Oxeno GmbHInventors: Jochen Praefke, Armin Rix, Silvia Santiago Fernandez, Matthias Groemping, Frank Hoeper, Udo Peters, Joerg Leistner, Franz Nierlich, Dirk Roettger
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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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Patent number: 7842843Abstract: To provide a C4 fraction that contains significantly reduced amounts of butynes and methylallene and to provide a process for low-cost and effective production of ethers in which the C4 fraction is used as the starting material for a telomerization process. A mixture containing 25 to 80 mass % 1,3-butadiene, 13 to 68 mass % butenes and 2 to 15 mass % butanes with butynes and methylallene being contained in amounts of 50 ppm or less and 5 to 800 ppm, respectively.Type: GrantFiled: November 29, 2006Date of Patent: November 30, 2010Assignee: Kuraray Co., Ltd.Inventors: Jin Tokuyasu, Hideharu Iwasaki
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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: 7423168Abstract: A method for producing an allyl compound having a compositional formula different from that of an allyl starting material compound, which comprises reacting the allyl starting material compound with an oxygen nucleophilic agent having a structure different from that of the allyl starting material compound in the presence of a catalyst containing at least one transition metal compound containing a transition metal selected from the group consisting of transition metals belonging to Group 8 to Group 10 of the Periodic Table and a monodentate phosphite compound having a structure of the following formula (1): P(OR1)(OR2)(OR3)??(1) wherein R1, R2 and R3 are respectively independently an alkyl group which may have a substituent, carbon chains of R1, R2 and R3 may have at least one carbon-carbon double bond or triple bond, and at least two optional groups of R1, R2 and R3 may bond to each other to form at least one cyclic structure.Type: GrantFiled: August 28, 2003Date of Patent: September 9, 2008Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Yoshiyuki Tanaka
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Patent number: 7119222Abstract: A method for producing an allyl compound having a compositional formula different from that of an allyl starting material compound, which comprises reacting the allyl starting material compound with an oxygen nucleophilic agent in the presence of a catalyst containing at least one transition metal compound containing a transition metal selected from the group consisting of transition metals belonging to Group 8 to Group 10 of the Periodic Table and a multidentate phosphite compound.Type: GrantFiled: August 27, 2003Date of Patent: October 10, 2006Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Yoshiyuki Tanaka
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Patent number: 7026523Abstract: The invention provides a process for the telomerization of acyclic olefins having at least two conjugated double bonds (I) or mixtures comprising such olefins by means of nucleophiles (II) using a palladium-carbene complex as catalyst.Type: GrantFiled: May 4, 2002Date of Patent: April 11, 2006Assignee: OXENO Olefinchemie GmbHInventors: Dirk Röttger, Matthias Beller, Ralf Jackstell, Holger Klein, Klaus-Diether Wiese
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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: 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: 6037482Abstract: A process for the catalytic addition of nucleophilic agents to alkynes or allenes to form alkenes substituted by the nucleophile which may further react with the nucleophile and/or isomerize comprises using a catalyst comprising a wholly or partly ionized complex of univalent gold.Type: GrantFiled: June 15, 1998Date of Patent: March 14, 2000Assignee: BASF AktiengesellschaftInventors: Michael Schulz, Joaquim Henrique Teles
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Patent number: 5510541Abstract: Mono-alkadienyl alkyl ethers and di-alkadienyl alkyl ethers are prepared by telomerization of a conjugated diene, by causing said conjugated diene to react with an aliphatic alcohol or an aliphatic diol respectively, by operating in an aqueous/organic biphasic liquid system, in the presence of a catalytic system formed by:(a) a palladium salt or complex;(b) an alkyl-, alkylcycloalkyl-, or alkylarylphosphine ligand, bearing an acidic or neutral hydrophylic moiety, having the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, x and y are as defined in the disclosure; and(c) an either inorganic or organic base.Type: GrantFiled: February 25, 1994Date of Patent: April 23, 1996Assignee: Snamprogetti S.p.A.Inventors: Renata Patrini, Mario Marchionna
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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: 5254782Abstract: Continuous process for the telomerization of conjugated dienes comprising reacting a conjugated diene with a compound containing an active hydrogen atom in the liquid phase in the presence of a Group VIII transition metal catalyst, a ligand compound of a tertiary phosphorous, arsenic or antimony, and a catalyst promoter compound having basic properties.Type: GrantFiled: August 16, 1991Date of Patent: October 19, 1993Assignee: The Dow Chemical CompanyInventors: Barend J. Schaart, Hendrik L. Pelt, Grant B. Jacobsen
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Patent number: 5243099Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.Type: GrantFiled: September 9, 1992Date of Patent: September 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5198598Abstract: Alkadienyl ethers are prepared by the telomerization of conjugated dienes with polyols by continuous addition of the alkadiene to a reaction mixtue comprised of the polyol, secondary alcohol solvent, a portion of the alkadiene to be added, and low palladium catalyst concentration.Type: GrantFiled: July 19, 1991Date of Patent: March 30, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karlheinz Hill, Steven D. Axt, Kenneth J. Weese
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Patent number: 5169981Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.Type: GrantFiled: December 6, 1991Date of Patent: December 8, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5159121Abstract: A catalyst system for the selective production of isoprenylalkylethers from isoprene is described, characterized by satisfying the following empirical formulaPdLxL'ywhere L is a phosphorated binder in the form of an organic derivative of trivalent phosphorous of type R.sub.3 P or R.sub.2 P[CH(R)].sub.z PR.sub.2, 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' 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 R.sub.3 P or R.sub.2 P[CH(R)].sub.z PR.sub.2 type may or may not be present.Type: GrantFiled: January 24, 1992Date of Patent: October 27, 1992Assignee: Snamprogetti S.p.A.Inventors: Renata Patrini, Mario Marchionna, Massimo Lami, Francesco Ancillotti
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Patent number: 4831183Abstract: A process for the telomerization of a conjugated alkadiene with an organic hydroxy compound to produce an organo-oxyalkadiene is disclosed. A palladium catalyst having an ionic ligand is employed in a substantially oxygen-free environment in the presence of an aprotic polar solvent so that the reaction products may be separated from the catalyst by solvent extraction with a hydrocarbon solvent.Type: GrantFiled: October 17, 1988Date of Patent: May 16, 1989Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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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: 4642392Abstract: A process for the telomerization of a conjugated alkadiene with an alkanol is disclosed for the production of an organo-oxyalkadiene. A palladium catalyst having a phosphine or stibene ligand is employed in a substantially oxygen-free environment and in the presence of a high boiling solvent so that the reaction products may be separated from the catalyst by distillation. Vacuum fractional distillation is a preferred method for separating the products.Type: GrantFiled: September 30, 1985Date of Patent: February 10, 1987Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4399301Abstract: Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.Type: GrantFiled: September 13, 1979Date of Patent: August 16, 1983Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4277633Abstract: The palladium complex disclosed herein is bis[tri(ortho-tolyl)phosphine] :palladium which is produced by reacting a palladium salt with tri(ortho-tolyl)phosphine and reducing the resultant bis[tri(ortho-tolyl)phosphine] palladium salt with an alcoholic alkali. This complex is useful as a catalyst for the production of 1,3-diene oligomers.Type: GrantFiled: July 12, 1979Date of Patent: July 7, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
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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
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Patent number: 4146738Abstract: Acyclic conjugated diolefins of 4-6 carbon atoms can be telomerized or oligomerized by themselves or with H-acidic compounds in the presence of an activated palladium (triarylphosphine) catalyst prepared by oxidatative removal of 1-3.5 molar equivalents of triphenylphosphine from palladium tetrakis(triphenylphosphine). The thus-obtained, activated palladium complex is recovered, after termination of the telomerization and/or oligomerization, by adding 2-6 molar equivalents of triphenylphosphine to the reaction product, distilling the telomer or oligomer therefrom and recovering the thus-regenerated palladium tetrakis(triphenylphosphine) from the distillation residue.Type: GrantFiled: July 26, 1977Date of Patent: March 27, 1979Assignee: Chemische Werke Huels, AktiengesellschaftInventors: Hans Jadamus, Klaus Diebel