Organic Material Which Contains Phosphorus, Arsenic, Or Antimony, In Addition To Nickel, Utilized (e.g., Zero-valent Nickel Complexes, Etc.) Patents (Class 558/338)
  • Publication number: 20080015379
    Abstract: The invention provides a process for hydrocyanation, comprising: contacting 2-pentenenitrile with hydrogen cyamide at a temperature in the range of about 0° C. to about 150° C. in the presence of at least one Lewis acid promoter and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one bidentate phosphite ligand selected from a member of the group represented by Formula I and Formula II, in which all like reference characters have the same meaning, except as further explicitly limited: wherein R1 and R5 are independently selected from the group consisting of C1 to C5 hydrocarbyl; and R2, R3, R4, R6, R7 and R8 are independently selected from the group consisting of H and C1 to C4 hydrocarbyl.
    Type: Application
    Filed: July 12, 2007
    Publication date: January 17, 2008
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: JAMES MICHAEL GARNER, Christian P. Lenges, Ronald J. McKinney, Wilson Tam
  • Publication number: 20080015381
    Abstract: The invention provides a hydrocyanation process for the production of adiponitrile and other dinitriles having six carbon atoms, the process comprising: a) forming a reaction mixture in the presence of at least one Lewis acid, said reaction mixture comprising ethylenically unsaturated nitrites having five carbon atoms, hydrogen cyanide, and a catalyst precursor composition, by continuously feeding ethylenically unsaturated nitrites, hydrogen cyanide, and a catalyst precursor composition; b) controlling X and Z, wherein X is the overall feed molar ratio of 2-pentenenitriles to all unsaturated nitriles and Z is the overall feed molar ratio of hydrogen cyanide to all unsaturated nitrites, by selecting a value for X in the range from about 0.001 to about 0.5, and a value for Z in the range from about 0.5/1 to about 0.
    Type: Application
    Filed: July 12, 2007
    Publication date: January 17, 2008
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: THOMAS FOO, James Michael Garner, Ron Ozer
  • Patent number: 7105696
    Abstract: The invention concerns a method for hydrocyanation of ethylenically unsaturated organic compounds comprising at least a nitrile function. The invention provides a method for hydrocyanation of an ethylenically unsaturated hydrocarbon compound by reacting in liquid medium the hydrogen cyanide in the presence of a catalyst comprising a metal element selected among transition metals and an organophosphorous ligand, characterised in that the organophosphorous ligand is a furylphosphine. The invention is in particular useful for synthesizing adiponitrile from butadiene.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: September 12, 2006
    Assignee: Rhodia Polymide Intermediates
    Inventors: Paolo Burattin, Alex Chamard, Jean-Christophe Galland
  • Patent number: 7098358
    Abstract: The invention concerns a method for hydrocyanation of ethylenically unsaturated organic compounds into compounds comprising at least a nitrile function. More particularly, it concerns a method for hydrocyanation of organic compounds comprising at least a ethylenical bond by reacting hydrogen cyanide, in the presence of a catalytic system comprising a transition metal and an organophosphorus ligand. The organophosphorus ligand is a compound with monophosphanorbornadiene structure. The invention concerns in particular hydrocyanation of butadiene into adiponitrile.
    Type: Grant
    Filed: October 3, 2001
    Date of Patent: August 29, 2006
    Assignee: Rhodia Polyamides Intermediates
    Inventors: Paolo Burattin, Jean-Christophe Galland, Alex Chamard
  • Patent number: 7084294
    Abstract: A process for the recovery of a Lewis acid from a reaction mixture (I) which has been obtained in the hydrocyanation of an olefinically unsaturated compound to a nitrile which has a miscibility gap with water under certain pressure and temperature conditions, in the presence of a catalyst system comprising a Lewis acid and a complex compound.
    Type: Grant
    Filed: July 4, 2003
    Date of Patent: August 1, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Tim Jungkamp, Jens Scheidel, Hermann Luyken, Michael Bartsch, Robert Baumann, Gerd Haderlein
  • Patent number: 7067685
    Abstract: The invention relates to phosphinites I of formulae (1) or (2), in which R1, R2, R5, R6, R7, R8, R9 independently represent hydrogen, an alkyl or alkylene group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms; R3 is H or methyl; R4 is i-propyl or t-butyl; X is F, Cl or CF3 and n is 1 or 2
    Type: Grant
    Filed: October 4, 2002
    Date of Patent: June 27, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Bartsch, Robert Baumann, Dagmar Pascale Kunsmann-Keitel, Gerd Haderlein, Tim Jungkamp, Marco Altmayer, Wolfgang Siegel, Ferenc Molnar
  • Patent number: 6936171
    Abstract: Disclosed herein is a process for recovering diphosphite-containing compounds from a mixture comprising diphosphite-containing compounds and organic dinitriles and Lewis acid, using liquid-liquid extraction, wherein the molar ratio of organic mononitrile present to organic dinitrile from about 0.01 to about 2.5 and wherein the mixtured is treated with a Lewis base compound selected from the group consisting of monodentate phosphite ligand, alcohol, water, organoamines, ammonia and basic resin, and wherein the extraction solvent is a saturated or unsaturated alkane or saturated or unsaturated cycloalkane; wherein the Lewis base compound is selected from the group consisting of water, methanol, ethanol, isopropanol, ethylene glycol, phenol, cresol, or xylenol. Also disclosed are pre-treatments to enhance extractability of the diphosphite-containing compounds.
    Type: Grant
    Filed: January 8, 2003
    Date of Patent: August 30, 2005
    Assignee: Invista North America S.a.r.l.
    Inventors: Scott C. Jackson, Ronald J. Mckinney
  • Patent number: 6897329
    Abstract: A process for preparing a hydrocyanation catalyst comprising contacting a bidentate phosphorous-containing ligand with nickel chloride in the presence of a nitrile solvent and a reducing metal which is more electropositive than nickel the nickel chloride being introduced as an aqueous solution and the water being removed concurrently with the reduction reaction by azeotropic distillation.
    Type: Grant
    Filed: January 14, 2003
    Date of Patent: May 24, 2005
    Assignee: Invista North America S.A.R.L.
    Inventors: Scott C. Jackson, Ronald J. McKinney
  • Patent number: 6852661
    Abstract: A catalyst comprising at least one complex of a metal of transition group VIII comprising at least one monodentate, bidentate or multidentate phosphinamidite ligand in which the phosphorus atom and the oxygen atom of the phosphinamidite group form part of a 5- to 8-membered heterocycle can be used for the hydroformylation and hydrocyanation of compounds containing at least one ethylenically unsaturated double bond. The phosphinamidite ligand is, for example, represented by the following formulae wherein represents an optionally substituted 5- to 8-membered heterocycle wherein A represents carbon ring members; represents an optionally substituted N-bonded heterocycle wherein (Het) indicates optional ring heteroatoms in addition to the N; and B is a carbon-carbon single bond or a divalent bridging group.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: February 8, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Ahlers, Heiko Maas, Michael Röper
  • Patent number: 6812352
    Abstract: Multidentate phosphite ligands are disclosed for use in reactions such as hydrocyanation and isomerization. The catalyst compositions made therefrom and the various catalytic processes which employ such multidentate phosphite ligands are also disclosed. In particular, the ligands have heteroatom-containing substituents on the carbon attached to the ortho position of the terminal phenol group.
    Type: Grant
    Filed: April 9, 2002
    Date of Patent: November 2, 2004
    Assignee: Invista North America S.a.r.l.
    Inventors: Kristina Ann Kreutzer, Wilson Tam, J. Michael Garner, John Ronald Boyles
  • Publication number: 20040138494
    Abstract: A process for preparing a hydrocyanation catalyst comprising contacting a bidentate phosphorous-containing ligand with nickel chloride in the presence of a nitrile solvent and a reducing metal which is more electropositive than nickel the nickel chloride being introduced as an aqueous solution and the water being removed concurrently with the reduction reaction by azeotropic distillation.
    Type: Application
    Filed: January 14, 2003
    Publication date: July 15, 2004
    Inventors: Scott C. Jackson, Ronald J. McKinney
  • Patent number: 6737539
    Abstract: Disclosed herein are processes for hydrocyanation and isomerization of olefins by using at least one multidentate phosphonite ligands, including organometallic phosphonite ligands with a Group VIII metal or Group VIII metal compound, and optionally, a Lewis acid promoter.
    Type: Grant
    Filed: June 4, 2003
    Date of Patent: May 18, 2004
    Assignee: E. I. DuPont de Nemours and Company
    Inventors: Christian P. Lenges, Helen S. M. Lu, Joachim C. Ritter
  • Patent number: 6642405
    Abstract: For the production of acrylonitrile by ammoxidation of propylene, there is provided a process capable of giving a high yield and maintaining such an effect for a long period of time. In producing acrylonitrile by ammoxidation of propylene, a fluidized bed catalyst is used and the reaction is carried out while appropriately adding a molybdenum-containing material, wherein the fluidized bed catalyst contains molybdenum, bismuth, iron, nickel, chromium, potassium, an F component and silica as essential components, and has a number of Mo/Me of from 0.8 to 1, wherein the Mo/Me is a number obtained by dividing the product 20 of a valence number of molybdenum as molybdic acid and an atomic ratio of molybdenum by the sum of respective products of respective valence numbers and atomic ratios of bismuth, iron, nickel, chromium, potassium, the F component element, a G component element and a Y component element.
    Type: Grant
    Filed: April 10, 2002
    Date of Patent: November 4, 2003
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kunio Mori, Yutaka Sasaki, Kenichi Miyaki, Hirokazu Watanabe
  • Publication number: 20030195372
    Abstract: Disclosed herein are processes for hydrocyanation and isomerization of olefins by using at least one multidentate phosphonite ligands, including organometallic phosphonite ligands with a Group VIII metal or Group VIII metal compound, and optionally, a Lewis acid promoter.
    Type: Application
    Filed: June 4, 2003
    Publication date: October 16, 2003
    Inventors: Christian P. Lenges, Helen S. M. Lu, Joachim C. Ritter
  • Patent number: 6521778
    Abstract: A catalyst which comprises at least one complex of a metal of subgroup VIII having at least one bidentate phosphonite ligand of the formula I or salts and mixtures thereof, a process for the preparation of mixtures of monoolefinic C5-mononitriles, a process for the catalytic isomerization of branched aliphatic monoalkenenitriles and a process for the preparation of adiponitrile.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: February 18, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jakob Fischer, Wolfgang Siegel, Dagmar Pascale Keitel, Lorenz Siggel
  • Publication number: 20030023110
    Abstract: Multidentate phosphite ligands are disclosed for use in reactions such as hydrocyanation and isomerization. The catalyst compositions made therefrom and the various catalytic processes which employ such multidentate phosphite ligands are also disclosed. In particular, the ligands have heteroatom-containing substituents on the carbon attached to the ortho position of the terminal phenol group.
    Type: Application
    Filed: April 9, 2002
    Publication date: January 30, 2003
    Inventors: Wilson Tam, J. Michael Garner, John Ronald Boyles
  • Publication number: 20030018208
    Abstract: A catalyst comprising a promoted mixed metal oxide is useful for the vapor phase oxidation of an alkane or a mixture of an alkane and an alkene to an unsaturated carboxylic acid and for the vapor phase ammoxidation of an alkane or a mixture of an alkane and an alkene to an unsaturated nitrile.
    Type: Application
    Filed: August 22, 2002
    Publication date: January 23, 2003
    Inventors: Sanjay Chaturvedi, Anne Mae Gaffney, Scott Han, Michele Doreen Hefener, Ruozhi Song
  • Patent number: 6486359
    Abstract: The invention relates to a catalyst which comprises at least one complex of a metal of group VIII, which comprises at least one uni-, bi- or multidentate phosphinite ligand in which the phosphorus atom and the oxygen atom of the phosphinite group are part of a 5- to 8-membered heterocycle, and to processes for hydroformylation and hydrocyanation of compounds which contain at least one ethylenic double bond in the presence of a catalyst of this type.
    Type: Grant
    Filed: December 12, 2000
    Date of Patent: November 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Heiko Maas, Rocco Paciello, Michael Röper, Jakob Fischer
  • Patent number: 6469194
    Abstract: Ethylenically unsaturated organic compounds, for example diolefins, olefinic nitriles and monoolefins, are noncontaminatingly hydrocyanated into corresponding nitriles by (a) reacting such ethylenically unsaturated organic compounds with hydrogen cyanide in the presence of an aqueous solution containing a catalytically effective amount of a catalyst which comprises at least one nickel compound and at least one water-soluble phosphine, (b) thereafter separating the organic phase from the aqueous phase which result, the separated aqueous phase comprising a solid phase formed during hydrocyanation, and (c) thence treating the separated aqueous phase, or a solid phase removed therefrom, with hydrogen cyanide to thus at least partially dissolve said solid phase contained therein or removed therefrom.
    Type: Grant
    Filed: June 22, 2001
    Date of Patent: October 22, 2002
    Assignee: Rhodia Fiber & Resin Intermediates
    Inventors: Paolo Burattin, Pierre Coqueret, Marc Huser
  • Patent number: 6380421
    Abstract: Hydrocyanation reactions employing multidentate phosphite ligands and multidentate phosphite ligands are disclosed. The ligands have phenyl containing substituents attached to the ortho position of the terminal phenol group and/or attached to the ortho position of the bridging group. Catalyst compositions havng such ligands achieve 97% or greater distribution in hydrocyanation.
    Type: Grant
    Filed: August 30, 2000
    Date of Patent: April 30, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Helen S. M. Lu, Nora Radu
  • Publication number: 20020026066
    Abstract: Hydrocyanation catalysts comprising aqueous solutions of at least one water-soluble phosphine and nickel values, well suited for the hydrocyanation of ethylenically unsaturated organic compounds such as diolefins, olefinic nitrites and monolefins, are produced by (a) admixing an aqueous solution of such at least one water-soluble phosphine with a nickel hydroxide, (b) adding hydrogen cyanide or a compound which generates hydrogen cyanide to the mixture thus formed, (c) stirring the resulting mixture until the nickel values have at least partially dissolved, and (d) reducing at least a portion of said nickel values having an oxidation state of greater than zero to the zero oxidation state.
    Type: Application
    Filed: June 22, 2001
    Publication date: February 28, 2002
    Inventors: Paolo Burattin, Pierre Coqueret, Marc Huser
  • Publication number: 20020022736
    Abstract: Ethylenically unsaturated organic compounds, for example diolefins, olefinic nitrites and monoolefins, are noncontaminatingly hydrocyanated into corresponding nitrites by (a) reacting such ethylenically unsaturated organic compounds with hydrogen cyanide in the presence of an aqueous solution containing a catalytically effective amount of a catalyst which comprises at least one nickel compound and at least one water-soluble phosphine, (b) thereafter separating the organic phase from the aqueous phase which result, the separated aqueous phase comprising a solid phase formed during hydrocyanation, and (c) thence treating the separated aqueous phase, or a solid phase removed therefrom, with hydrogen cyanide to thus at least partially dissolve said solid phase contained therein or removed therefrom.
    Type: Application
    Filed: June 22, 2001
    Publication date: February 21, 2002
    Inventors: Paolo Burattin, Pierre Coqueret, Marc Huser
  • Patent number: 6242633
    Abstract: A catalyst comprising at least one nickel(0) complex which comprises at least one mono-, bi- or multidentate phosphonite ligand of the formula I or salts and mixtures thereof, is prepared as described, and the catalysts are used to prepare mixtures of monoolefinic C5 mononitriles with nonconjugated C═C and C≡N bonds by catalytic hydrocyanation of butadiene or of a 1,3-butadiene-containing hydrocarbon mixture in the presence of a catalyst of this type.
    Type: Grant
    Filed: March 7, 2000
    Date of Patent: June 5, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Jakob Fischer, Wolfgang Siegel
  • Patent number: 6197992
    Abstract: The disclosure is a process for preparing mixtures of monoolefinic C5 mononitriles having nonconjugated C═C— and C≡N bonding by catalytic hydrocyanation of a hydrocarbon mixture containing 1,3-butadiene, by first diminishing the proportion of those components in the hydrocarbon mixture which impair the catalytic hydrocyanation and then subjecting the resulting mixture to catalytic hydrocyanation.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: March 6, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Jakob Fischer, Wolfgang Siegel, Klaus Mundinger, Gerald Meyer
  • Patent number: 6171996
    Abstract: A process for hydrocyanation of an aliphatic monoethylenically unsaturated compound, in which the ethylenic double bond is not conjugated to any other unsaturated group in the molecule, or a monoethylenically unsaturated compound in which the ethylenic double bond is conjugated to an ester group, which process uses a catalyst composition comprising a zero-valent nickel and a multidentate phosphite ligand in the presence of a Lewis acid promoter.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: January 9, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: James Michael Garner, Kristina Ann Kruetzer, Wilson Tam
  • Patent number: 6169198
    Abstract: A process for preparing mixtures of monoolefinic C5 mononitriles with nonconjugated C═C and C≡N bonds by catalytic hydrocyanation of 1,3-butadiene or a 1,3-butadiene-containing hydrocarbon mixture, wherein the hydrocyanation takes place in the presence of a catalyst which comprises at least one metallocene-phosphorus(III)-nickel(0) complex which comprises at least one monodentate or bidentate metallocene-phosphorus(III) ligand of the formula I or salts and mixtures thereof.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: January 2, 2001
    Assignee: BASF Aktiengesellshaft
    Inventors: Jakob Fischer, Wolfgang Siegel
  • Patent number: 6162942
    Abstract: A process for preparing aromatic nitriles from corresponding chloroaromatics by reaction with cyanides.
    Type: Grant
    Filed: August 17, 1999
    Date of Patent: December 19, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael-Harold Rock, Albrecht Marhold
  • Patent number: 6127567
    Abstract: A process for hydrocyanation of an aliphatic monoethylenically unsaturated compound, in which the ethylenic double bond is not conjugated to any other unsaturated group in the molecule, or a monoethylenically unsaturated compound in which the ethylenic double bond is conjugated to an ester group, which process uses a catalyst composition comprising a zero-valent nickel and a multidentate phosphite ligand in the presence of a Lewis acid promoter.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: October 3, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: James Michael Garner, Kristina Ann Kruetzer, Wilson Tam
  • Patent number: 6048996
    Abstract: An improved process for converting an acylcic monoolefin to its corresponding terminal organonitrile by reacting the monoolefin with hydrogen cyanide in the presence of zero-valent nickel, a phosphite ligand, and an insoluble Lewis acid promoter.
    Type: Grant
    Filed: August 26, 1999
    Date of Patent: April 11, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Lucy Mary Clarkson, Norman Herron, William C. Kalb, Ronald James McKinney, Edward Francis Moran, Jr.
  • Patent number: 6020516
    Abstract: Improved liquid phase process useful in the hydrocyanation of diolefinic compounds to produce nonconjugated acyclic nitrites and to the liquid phase process of isomerization of the nitriles to, among other things, 3- and/or 4-monoalkene linear nitrites. The improvement involves conducting the process in the presence of zero-valent nickel and a multidentate phosphite ligand.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: February 1, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Thomas Foo, James Michael Garner, Wilson Tam
  • Patent number: 5981772
    Abstract: Improved liquid phase process useful in the hydrocyanation of diolefinic compounds to produce nonconjugated acyclic nitrites and to the liquid phase process of isomerization of the nitrites to, among other things, 3- and/or 4-monoalkene linear nitrites. The improvement involves conducting the process in the presence of zero-valent nickel and a multidentate phosphite ligand. Novel multidentate phosphite ligands and catalyst precursor compositions made therefrom are also disclosed.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: November 9, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Thomas Foo, James Michael Garner, Wilson Tam
  • Patent number: 5959135
    Abstract: A process for hydrocyanation of an aliphatic monoethylenically unsaturated compound, in which the ethylenic double bond is not conjugated to any other unsaturated group in the molecule, which process uses a catalyst composition comprising a zero-valent nickel and a multidentate phosphite ligand in the presence of a Lewis acid promoter.
    Type: Grant
    Filed: July 8, 1998
    Date of Patent: September 28, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: James Michael Garner, Wilson Tam
  • Patent number: 5856555
    Abstract: The present invention relates to a process for the hydrocyanation of organic compounds containing ethylenic unsaturation to nitrites, in particular the hydrocyanation of diolefins or of substituted olefins, such as alkenenitriles.More specifically, it comprises a process for the hydrocyanation of organic compounds containing at least one ethylenic double bond by reaction with hydrogen cyanide in the presence of an aqueous solution of a catalyst comprising at least one transition metal compound and at least one water-soluble phosphine, characterized in that the said water-soluble phosphine is a monodentate or bidentate phosphine.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: January 5, 1999
    Assignee: Rhone-Poulenc Fiber & Resin Intermediates
    Inventors: Marc Huser, Robert Perron
  • Patent number: 5847191
    Abstract: The present invention provides a process for hydrocyanation comprising reacting a nonconjugated, ethylenically unsaturated compound in a two phase process solvent with HCN in the presence of a Lewis acid promoter and a catalyst system comprising zero-valent nickel and an organic phosphorous containing ligand having the structure (PR.sub.2).sub.n R' where n is an integer from 1 to 2, R and R' are organic residues which may be the same or different and where the R or R' contain at least one C9 to C40 aliphatic group positioned as a tail extending away from the primary ligand structure rendering the ligand lipophilic.
    Type: Grant
    Filed: July 29, 1997
    Date of Patent: December 8, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Emilio Enrique Bunel, Kenneth C. McNulty
  • Patent number: 5821378
    Abstract: Improved liquid phase process useful in the hydrocyanation of diolefinic compounds to produce nonconjugated acyclic nitrites and to the liquid phase process of isomerization of the nitrites to 3- and/or 4-monoalkene linear nitriles. The improvement involves conducting the process in the presence of zero-valent nickel and a multidentate phosphite ligand. The invention also provides a novel method of making phosphorochloridite.
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: October 13, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Thomas Foo, Wilson Tam
  • Patent number: 5723641
    Abstract: Processes for hydrocyanation of nonconjugated acyclic aliphatic monoolefins, monoolefins conjugated to an ester group, or monoolefins conjugated to a nitrile group which utilize a catalyst precursor composition comprising a bidentate phosphite ligand and zero-valent nickel preferably in the presence of a Lewis acid promoter. Catalyst precursor compositions are also disclosed.
    Type: Grant
    Filed: September 26, 1996
    Date of Patent: March 3, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Wilson Tam, Kristina Ann Kreutzer, Ronald James McKinney
  • Patent number: 5693843
    Abstract: Described herein is a process for the hydrocyanation of diolefins by employing a catalyst comprising the combination of a zero-valent nickel compound and certain bidentate phosphorus compounds, and a process for isomerizing 2-alkyl-3-monoalkenenitrile to form linear nitriles by the use of such catalyst.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: December 2, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Anne Irisa Breikss, Thomas Foo
  • Patent number: 5688986
    Abstract: Processes for hydrocyanation of nonconjugated acyclic aliphatic monoolefins, monoolefins conjugated to an ester group, or monoolefins conjugated to a nitrile group which utilize a catalyst precursor composition comprising a bidentate phosphite ligand and zero-valent nickel preferably in the presence of a Lewis acid prompter. Catalyst precursor compositions are also disclosed.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: November 18, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Wilson Tam, Kristina Ann Kreutzer, Ronald James McKinney
  • Patent number: 5543536
    Abstract: Catalyst compositions comprising zero-valent nickel and a mondentate phosphite ligand are provided, with a process for the hydrocyanation of monoolefins using these compositions in the presence of a Lewis acid promoter.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: August 6, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wilson Tam
  • Patent number: 5523453
    Abstract: A process for hydrocyanation of certain ethylenically unsaturated compounds which uses a catalyst composition comprising certain bidentate phosphorous compounds and zero-valent nickel in the presence of a Lewis Acid promoter.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: June 4, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Anne I. Breikss
  • Patent number: 5512695
    Abstract: Processes for hydrocyanation of nonconjugated aliphatic monoolefins or monoolefins conjugated to an ester group utilizing a catalyst precursor composition comprising an unsymmetrical bidentate phosphite ligand and zero-valent nickel, preferably in the presence of a Lewis acid promoter, to produce a terminal organonitrile. Catalyst precursor compositions are also disclosed.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: April 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Kristina A. Kreutzer, Wilson Tam
  • Patent number: 5512696
    Abstract: A process for hydrocyanation of an aliphatic monoethylenically unsaturated compound, in which the ethylenic double bond is not conjugated to any other unsaturated group in the molecule, or a monoethylenically unsaturated compound in which the ethylenic double bond is conjugated to an ester group, which process uses a catalyst composition comprising a zero-valent and a multidentate phosphite ligand in the presence of a Lewis acid promoter.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: April 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Kristina A. Kreutzer, Wilson Tam
  • Patent number: 5510470
    Abstract: A chiral, bidentate organophosphorus ligand containing a dideoxysaccharide used along with zero valent nickel as a catalyst for enantioselective hydrocyanation. The preferred organophosphorus ligand species is phenyl 2,3-bis-O-(3,5-bis(trifluoromethyl)phenyl)phosphine-4,6-O-benzylidene-B-D- glucopyranoside.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: April 23, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Albert L. Casalnuovo, Thaliyil V. Rajanbabu
  • Patent number: 5488129
    Abstract: Ethylenically unsaturated aliphatic nitriles, for example the linear pentenenitriles, are converted/hydrocyanated into their corresponding dinitriles, for example adiponitrile, by reacting such nitriles with hydrogen cyanide, in an aqueous reaction medium which comprises (1) a catalytically effective amount of a transition metal compound and a sulfonated phosphine, together with (2) a cocatalytically effective amount of at least one Lewis acid; the Lewis acid cocatalyst promotes the linearity of the final product dinitriles and/or prolongs the useful life of the catalyst.
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: January 30, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Huser, Robert Perron
  • Patent number: 5449807
    Abstract: A catalyzed vapor phase process for the hydrocyanation of acyclic diolefinic compounds to olefinic nitriles in which the olefinic double bond is not conjugated to the triple bond of the cyano group, wherein a catalyst composition comprising at least one bidentate phosphite ligand and zero-valent nickel is used.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: September 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joe D. Druliner
  • Patent number: 5312957
    Abstract: The invention provides a process for enantioselective hydrocyanation of aromatic vinyl compounds which produces nonracemic mixtures of chiral, arylpropionitriles; novel carbohydrate phosphorus and nickel catalyst compositions; and optically pure (S)-(-)-2-(6-methoxy-2-naphthalene)propionitrile.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: May 17, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Albert L. Casalnuovo, Thaliyil V. Rajanbabu, Lawrence W. Gosser, Ronald J. McKinney, Nugent, Jr. William A.
  • Patent number: 5175335
    Abstract: The invention provides a process for enantioselective hydrocyanation of aromatic vinyl compounds which produces nonracemic mixtures of chiral, arylpropionitriles; novel carbohydrate phosphorus and nickel catalyst compositions; and optically pure (S)-(-)-2-(6-metehoxy-2-naphthalene)propionitrile.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: December 29, 1992
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Albert L. Casalnuovo, Thaliyil V. Rajanbabu, Lawrence W. Gosser, Ronald J. McKinney, William A. Nugent, Jr.
  • Patent number: 5169971
    Abstract: The present invention relates to the production of a norcamphane dicarbonitrile and is directed to solving the problems of low conversion from the starting material, low selectivity and uneconomical production.According to the present invention, a norcamphane dicarbonitrile is produced by hydrocyanation of bicyclo [2,2,1]-5-heptene-2-carbonitrile in the presence of a zero-valent nickel complex catalyst and a Lewis acid.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: December 8, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masamitu Inomata, Naokazu Shiotani, Kazuo Koshizuka, Minato Karasawa
  • Patent number: 5143873
    Abstract: This invention concerns the use of M[BR.sub.3 H].sub.y reagents for activating or regenerating deactivated or degraded Ni catalyst used in Ni-catalyzed alkene hydrocyanation processes in the presence of an organic phosphorus compound, where M is an electropositive ion excluding nickel, such as, but not limited to, the Group 1A cations, the Group IIA cations, the lanthanide cations and the quaternary ammoniums and R is an organic radical of up to 18 carbon atoms, and where y is equal to the net charge of the cation. The invention also concerns a process for activation or regeneration of Ni-catalysts using MH and a catalytic amount of BR.sub.3.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: September 1, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Henry E. Bryndza, Albert L. Casalnuovo
  • Patent number: 5107012
    Abstract: Hydrocyanation of penetenenitriles using cyanohydrins as the HCN source and in which a solid dissociation additive is present in a slurry to facilitate the dissociation of the cyanohydrin.
    Type: Grant
    Filed: April 24, 1991
    Date of Patent: April 21, 1992
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Gerald C. Grunewald