Noble Metal Containing Catalyst Utilized Patents (Class 568/690)
  • Patent number: 10626072
    Abstract: 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: Grant
    Filed: January 4, 2018
    Date of Patent: April 21, 2020
    Assignee: LG CHEM, LTD.
    Inventors: Sung Ho Lee, Sang Beom Lee, Joon Ho Shin, In Yong Jeong
  • Patent number: 8558030
    Abstract: 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: Grant
    Filed: July 22, 2009
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: John R. Briggs, Jasson T. Patton, Sonet Vermaire-Louw, Peter M. Margl, Henk Hagen, Daryoosh Beigzadeh
  • Patent number: 8269050
    Abstract: 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: Grant
    Filed: December 21, 2006
    Date of Patent: September 18, 2012
    Assignee: Evonik Oxeno GmbH
    Inventors: Jochen Praefke, Armin Rix, Silvia Santiago Fernandez, Matthias Groemping, Frank Hoeper, Udo Peters, Joerg Leistner, Franz Nierlich, Dirk Roettger
  • 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
  • Patent number: 7842843
    Abstract: 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: Grant
    Filed: November 29, 2006
    Date of Patent: November 30, 2010
    Assignee: Kuraray Co., Ltd.
    Inventors: Jin Tokuyasu, Hideharu Iwasaki
  • 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: 7423168
    Abstract: 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: Grant
    Filed: August 28, 2003
    Date of Patent: September 9, 2008
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaki Takai, Yoshiyuki Tanaka
  • Patent number: 7119222
    Abstract: 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: Grant
    Filed: August 27, 2003
    Date of Patent: October 10, 2006
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaki Takai, Yoshiyuki Tanaka
  • Patent number: 7026523
    Abstract: 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: Grant
    Filed: May 4, 2002
    Date of Patent: April 11, 2006
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Dirk Röttger, Matthias Beller, Ralf Jackstell, Holger Klein, Klaus-Diether Wiese
  • 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: 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: 6037482
    Abstract: 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: Grant
    Filed: June 15, 1998
    Date of Patent: March 14, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Schulz, Joaquim Henrique Teles
  • Patent number: 5510541
    Abstract: 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: Grant
    Filed: February 25, 1994
    Date of Patent: April 23, 1996
    Assignee: Snamprogetti S.p.A.
    Inventors: Renata Patrini, Mario Marchionna
  • 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: 5254782
    Abstract: 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: Grant
    Filed: August 16, 1991
    Date of Patent: October 19, 1993
    Assignee: The Dow Chemical Company
    Inventors: Barend J. Schaart, Hendrik L. Pelt, Grant B. Jacobsen
  • Patent number: 5243099
    Abstract: 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: Grant
    Filed: September 9, 1992
    Date of Patent: September 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5198598
    Abstract: 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: Grant
    Filed: July 19, 1991
    Date of Patent: March 30, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karlheinz Hill, Steven D. Axt, Kenneth J. Weese
  • Patent number: 5169981
    Abstract: 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: Grant
    Filed: December 6, 1991
    Date of Patent: December 8, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5159121
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: October 27, 1992
    Assignee: Snamprogetti S.p.A.
    Inventors: Renata Patrini, Mario Marchionna, Massimo Lami, Francesco Ancillotti
  • Patent number: 4831183
    Abstract: 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: Grant
    Filed: October 17, 1988
    Date of Patent: May 16, 1989
    Assignee: National Distillers and Chemical Corporation
    Inventor: Ronnie M. Hanes
  • 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: 4642392
    Abstract: 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: Grant
    Filed: September 30, 1985
    Date of Patent: February 10, 1987
    Assignee: National Distillers and Chemical Corporation
    Inventor: Ronnie M. Hanes
  • Patent number: 4399301
    Abstract: 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: Grant
    Filed: September 13, 1979
    Date of Patent: August 16, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4277633
    Abstract: 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: Grant
    Filed: July 12, 1979
    Date of Patent: July 7, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
  • 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
  • Patent number: 4146738
    Abstract: 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: Grant
    Filed: July 26, 1977
    Date of Patent: March 27, 1979
    Assignee: Chemische Werke Huels, Aktiengesellschaft
    Inventors: Hans Jadamus, Klaus Diebel