Patents Represented by Attorney, Agent or Law Firm Marie F. Zuckerman
  • Patent number: 7906688
    Abstract: A calixarene bisphosphite composition for use as a ligand in a transition metal-ligand complex catalyst and in a complex catalyst precursor. The ligand is especially useful in catalysts and catalyst precursors for hydroformylation processes wherein a raffinate stream comprising a mixture of alpha, beta, and iso-olefinic isomers is hydroformylated in the presence of carbon monoxide, hydrogen, and the transition metal-ligand complex catalyst to form a mixture of linear and branched aldehyde products. The complex catalyst selectively converts the alpha and beta olefin reactants more rapidly than the iso-olefin reactant resulting in an improved molar ratio of normal (linear) to branched aldehyde products. The unconverted iso-olefinic isomer is thereafter readily separated from the aldehyde product mixture.
    Type: Grant
    Filed: April 3, 2008
    Date of Patent: March 15, 2011
    Inventors: Michael A. Brammer, Wei-Jun Peng, John M. Maher
  • Patent number: 7485759
    Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an ?-electron-withdrawing group, such as, an ?,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.
    Type: Grant
    Filed: January 24, 2008
    Date of Patent: February 3, 2009
    Assignee: Dow Technology Investments LLC
    Inventors: John R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
  • Patent number: 7351868
    Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an a-electronwithdrawing group, such as, an a,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.
    Type: Grant
    Filed: June 28, 2004
    Date of Patent: April 1, 2008
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
  • Patent number: 7294729
    Abstract: A novel bis-chelating composition characterized by formula I: wherein M is a Group VB element; R1 and R2 are each independently selected from hydrogen and monovalent hydrocarbyl radicals; or R1 and R2 are bonded together to form a diradical; or one of R1 or R2 is hydrogen or a monovalent hydrocarbyl radical, while the other of R1 or R2 is a hydrocarbyl radical bonded to an atom in Ar; wherein Ar is selected from 1,2-arylenes; Q is selected from 1,2-arylenes, 2,2?-bisarylenes and alkyl diradicals; and W is selected from II, III, IV, or V: wherein M is as defined hereinbefore; each R is independently selected from hydrogen and monovalent hydrocarbyl radicals; X is selected from alkyl and aryl diradicals; Ar1 and Ar2 are each independently selected from 1,2-arylenes;Ar3 and Ar4 are each independently selected from monovalent aryl radicals; and n in formula IV is 0 or 1.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: November 13, 2007
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Wei-Jun Peng, Johnathan E Holladay
  • Patent number: 7273941
    Abstract: A process of preparing an olefin oxide, preferably propylene oxide, and an alcohol, such as ?-ethylphenyl alcohol, the process involving contacting an olefin, such as propylene, and an organic hydroperoxide, such as ethylbenzene hydroperoxide, in the presence of an epoxidation catalyst, preferably, a homogeneous molybdenum catalyst, in a single reactor system or in a multi-reactor system containing a plurality of sequentially interconnected reactors. Each reactor in the single or multi-reactor system is preferably divided into a plurality of reaction zones designed to facilitate plug flow behavior. The olefin is fed to a first reaction zone in the single reactor system or to a first reactor in the multi-reactor system. The organic hydroperoxide feed is split into a plurality of split organic hydroperoxide feedstreams, and the split feedstreams are distributed throughout the reaction zones, or the reactors, or both.
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: September 25, 2007
    Assignee: Dow Global Technologies Inc.
    Inventors: Gary R. Strickler, George J. Quarderer, Jr., Joerg P. Lindner
  • Patent number: 7196230
    Abstract: A novel organophosphorus composition and synthesis thereof, the composition being characterized by one phosphite moiety, one phosoxophite moiety, and a plurality of sterically bulky substituents. The novel composition finds utility as a ligand in Group VIII transition metal phosoxophite complex catalysts and complex catalyst precursors that are used in carbonylation processes, preferably, hydroformylation processes. Additionally, there is disclosed a novel method of preparing a phosphoromonochloridite composition that finds utility as a precursor to the novel phosoxophite composition.
    Type: Grant
    Filed: March 4, 2003
    Date of Patent: March 27, 2007
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Wei-Jun Peng, David Robert Bryant
  • Patent number: 7176336
    Abstract: A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.
    Type: Grant
    Filed: September 14, 2004
    Date of Patent: February 13, 2007
    Assignee: Dow Global Technologies Inc.
    Inventors: Bob R. Maughon, Kenneth A. Burdett, Zenon Lysenko
  • Patent number: 7122491
    Abstract: A method of increasing the lifetime of a hydro-oxidation catalyst comprising, preferably, gold, silver, or mixtures thereof, and optionally one or more promoters, on a titanium-containing support, such as a titanosilicate or titanium dispersed on silica. The method of the invention involves contacting the catalyst support with a hydroxy-functionalized organosilicon compound, a carboxy-functionalized organosilicon compound, or a mixture of hydroxy- and carboxy-functionalized organosilicon compounds, such as, sodium methyl siliconate or (2-carboxypropyl)tetramethyldisiloxane. The contacting is preferably conducted during deposition of the catalytic metal(s) and optional promoters(s) onto the support. A catalyst composition and hydro-oxidation process utilizing the silicon-treated catalyst support are also claimed.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: October 17, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: David G. Barton, Robert G. Bowman, George E. Hartwell, Howard W. Clark, Alexander Kuperman
  • Patent number: 7119216
    Abstract: An olefin metathesis process involving contacting an unsaturated fatty acid ester or unsaturated fatty acid, such as methyloleate or oleic acid, with a lower olefin, preferably ethylene, in the presence of a metathesis catalyst so as to prepare a first product olefin, preferably, a reduced chain ?-olefin, such as methyl-9-decenoate or 9-decenoic acid, respectively. The metathesis catalyst contains ruthenium or osmium and a chelating ligand, preferably, a chelating ligand containing a carbene moiety and a second donor moiety of a Group 15 or 16 element Optionally, the catalyst can be supported on a catalyst support, such as, a cross-linked polymeric resin.
    Type: Grant
    Filed: February 27, 2002
    Date of Patent: October 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Thomas H. Newman, Cynthia L. Rand, Kenneth A. Burdett, Bob R. Maughon, Donald L. Morrison, Eric P. Wasserman
  • Patent number: 7097770
    Abstract: A solid bed adsorptive process for separating a seed oil into two substantially pure triglyceride fractions. The process involves contacting a seed oil, such as castor oil, preferably as a concentrate, with an adsorbent in a bed, the adsorbent having a particle size greater than about 40 microns, and thereafter contacting the adsorbent with a desorbent material, preferably under minimal flow conditions, to obtain a raffinate output stream containing predominantly a second triglyceride and an extract output stream containing predominantly a first triglyceride. Purified fatty acid triglyceride esters obtainable from castor, vernonia, and lesquerella plant oils provide renewable, non-petroleum-based sources of chemical feedstocks.
    Type: Grant
    Filed: March 21, 2002
    Date of Patent: August 29, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Zenon Lysenko, Sanjeev Katti, Richard Stringfield, Thomas Gregory, George J. Quarderer, Jr.
  • Patent number: 7018948
    Abstract: A process of activating a fresh catalyst or regenerating a deactivated catalyst which is used in a hydro-oxidation process, preferably, the hydro-oxidation of an olefin in the presence of oxygen and hydrogen to an olefin oxide. The hydro-oxidation catalyst preferably comprises at least one metal selected from gold, silver, the platinum group metals, the lanthanide metals, and combinations thereof, incorporated onto a titanium- , vanadium- , or zirconium-containing support, more preferably, a titanium-containing support, such as titanium oxide or a titanosilicate. The activation or regeneration process involves contacting the fresh catalyst or the deactivated catalyst with ozone.
    Type: Grant
    Filed: December 7, 2000
    Date of Patent: March 28, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Deborah H. Parker, Robert G. Bowman, Howard W. Clark, George E. Hartwell, Alex Kuperman
  • Patent number: 6984607
    Abstract: A process of preparing a catalyst comprising gold on a titanium-containing support. The method involves impregnating a support with a gold compound, a reducing agent, and optionally a promoter metal, wherein the reducing agent and/or the support contains titanium, and optionally heating the impregnated support. The catalyst is useful in the hydro-oxidation of olefins, such as propylene, with oxygen in the presence of hydrogen to olefin oxides, such as propylene oxide.
    Type: Grant
    Filed: March 15, 2004
    Date of Patent: January 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Alex Kuperman, Robert G. Bowman, Howard W. Clark, George E. Hartwell, Garmt R. Meima
  • Patent number: 6984763
    Abstract: An oxidative halogenation and optional dehydrogenation process involving contacting a reactant hydrocarbon having three or more carbon atoms, such as propane or propene, or a halogenated derivative thereof, with a source of halogen, and optionally, a source of oxygen in the presence of a rare earth halide or rare earth oxyhalide catalyst, so as to form a halogenated hydrocarbon product, such as allyl chloride, having three or more carbon atoms and having a greater number of halogen substituents as compared with the reactant hydrocarbon, and optionally, an olefinic co-product, such as propene. The less desired of the two products, that is, the halogenated hydrocarbon or the olefin as the case may be, can be recycled to the process to maximize the production of the desired product.
    Type: Grant
    Filed: April 23, 2002
    Date of Patent: January 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Albert E. Schweizer, Mark E. Jones, Daniel A. Hickman
  • Patent number: 6821924
    Abstract: An oxidative halogenation process involving contacting a hydrocarbon, for example, ethylene, or a halogenated hydrocarbon with a source of halogen, such as hydrogen chloride, and a source of oxygen in the presence of a catalyst so as to form a halocarbon, preferably a chlorocarbon, having a greater number of halogen substituents than the starting hydrocarbon or halogenated hydrocarbon, for example, 1,2-dichloroethane. The catalyst is a novel composition comprising copper dispersed on a porous rare earth halide support, preferably, a porous rare earth chloride support. A catalyst precursor composition comprising copper dispersed on a porous rare earth oxyhalide support is disclosed. Use of the porous rare earth halide and oxyhalide as support materials for catalytic components is disclosed.
    Type: Grant
    Filed: November 12, 2003
    Date of Patent: November 23, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Robert J. Gulotty, Jr., Mark E. Jones, Daniel A. Hickman
  • Patent number: 6821923
    Abstract: A process of preparing a catalyst comprising gold on a titanium-containing support. The method involves impregnating a support with a gold compound, a reducing agent, and optionally a promoter metal, wherein the reducing agent and/or the support contains titanium, and optionally heating the impregnated support. The catalyst is useful in the hydro-oxidation of olefins, such as propylene, with oxygen in the presence of hydrogen to olefin oxides, such as propylene oxide.
    Type: Grant
    Filed: April 7, 2000
    Date of Patent: November 23, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Alex Kuperman, Robert G. Bowman, Howard W. Clark, George E. Hartwell, Garmt R. Meima
  • Patent number: 6680415
    Abstract: An oxidative halogenation process involving contacting a hydrocarbon, for example, ethylene, or a halogenated hydrocarbon with a source of halogen, such as hydrogen chloride, and a source of oxygen in the presence of a catalyst so as to form a halocarbon, preferably a chlorocarbon, having a greater number of halogen substituents than the starting hydrocarbon or halogenated hydrocarbon, for example, 1,2-dichloroethane. The catalyst is a novel composition comprising copper dispersed on a porous rare earth halide support, preferably, a porous rare earth chloride support. A catalyst precursor composition comprising copper dispersed on a porous rare earth oxyhalide support is disclosed. Use of the porous rare earth halide and oxyhalide as support materials for catalytic components is disclosed.
    Type: Grant
    Filed: May 14, 2002
    Date of Patent: January 20, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Robert J. Gulotty, Jr., Mark E. Jones, Daniel A. Hickman
  • Patent number: 6646142
    Abstract: A process and catalysts for the direct oxidation of an olefin having three or more carbon atoms, such as propylene, by oxygen to an olefin oxide, such as prbpylene oxide. The process involves contacting the olefin under reaction conditions with oxygen in the presence of hydrogen and a catalyst. The catalyst contains silver and titanium, optionally gold, and optionally, at least one promoter element selected from Group 1, Group 2, zinc, cadmium, the platinum group metals, the lanthanide rare earths, the actinide elements, and combinations thereof. In preferred embodiments, the catalyst is calcined prior to use, rather than reduced prior to use. Suitable titanium-containing supports include titanium dioxide, titanium dioxide on silica, titanosilicates, promoter metal titanates, titanium dispersed on silica and promoter metal silicates.
    Type: Grant
    Filed: July 9, 2001
    Date of Patent: November 11, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Garmt R. Meima, Howard W. Clark, Robert G. Bowman, Alex Kuperman, George E. Hartwell
  • Patent number: 6479715
    Abstract: The present invention relates to a catalytic process for the preparation of alkylene glycols from alkylene oxide and water. Further, the invention relates to a method of preservation of catalysts in alkylene oxide containing systems. More in particular, it has been found that particular acids have a positive effect on the lifetime of catalyst systems based on anion exchange resins, and particularly those in the bicarbonate form.
    Type: Grant
    Filed: April 9, 2002
    Date of Patent: November 12, 2002
    Assignee: Dow Global Technologies Inc.
    Inventors: Gary R. Strickler, Guo-Shuh J. Lee, William J. Rievert, Daniel J. LaPrairie, Edward E. Timm
  • Patent number: 6362349
    Abstract: A process for the direct oxidation of an olefin by oxygen to the corresponding olefin oxide in the presence of a reducing agent and a catalyst. The catalyst comprises a metal component, such as a transition metal oxide, dispersed on a metal ion-exchanged metallosilicates, such as a Group 1 or Group 2 ion-exchanged porous aluminosilicate. Selectivity to the olefin oxide is high and the catalyst is readily regenerated.
    Type: Grant
    Filed: October 4, 2000
    Date of Patent: March 26, 2002
    Assignee: The Dow Chemical Company
    Inventors: Alex Kuperman, Robert G. Bowman, Howard W. Clark, George E. Hartwell
  • Patent number: 6362367
    Abstract: This invention relates to a process for producing one or more organic acids in high purity which process comprises (i) oxidizing in a liquid oxidation reactor one or more organic liquids with essentially pure oxygen or oxygen-enriched air containing at least about 50% oxygen, at a temperature sufficiently stable to prevent cycling of reaction rate, to produce a crude reaction product fluid, and (ii) refining said crude reaction product fluid to give said one or more organic acids in high purity. The oxidation temperature is preferably controlled to within about ±3° C. of a target temperature. The organic acids described herein is useful in a variety of applications, such as intermediates in the manufacture of chemical compounds, pharmaceutical manufacture and the like.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: March 26, 2002
    Assignee: Union Carbide Chemicals & Plastics Technology Corp.
    Inventors: John Braithwaite, David Robert Bryant, David James Miller, John Earl Logsdon