Organic Material Which Contains Phosphorus, Arsenic, Or Antimony, In Addition To Nickel, Utilized (e.g., Zero-valent Nickel Complexes, Etc.) Patents (Class 558/338)
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Publication number: 20080015379Abstract: 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: ApplicationFiled: July 12, 2007Publication date: January 17, 2008Applicant: INVISTA NORTH AMERICA S.A R.L.Inventors: JAMES MICHAEL GARNER, Christian P. Lenges, Ronald J. McKinney, Wilson Tam
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Publication number: 20080015381Abstract: 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: ApplicationFiled: July 12, 2007Publication date: January 17, 2008Applicant: INVISTA NORTH AMERICA S.A R.L.Inventors: THOMAS FOO, James Michael Garner, Ron Ozer
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Patent number: 7105696Abstract: 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: GrantFiled: December 21, 2001Date of Patent: September 12, 2006Assignee: Rhodia Polymide IntermediatesInventors: Paolo Burattin, Alex Chamard, Jean-Christophe Galland
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Patent number: 7098358Abstract: 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: GrantFiled: October 3, 2001Date of Patent: August 29, 2006Assignee: Rhodia Polyamides IntermediatesInventors: Paolo Burattin, Jean-Christophe Galland, Alex Chamard
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Patent number: 7084294Abstract: 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: GrantFiled: July 4, 2003Date of Patent: August 1, 2006Assignee: BASF AktiengesellschaftInventors: Tim Jungkamp, Jens Scheidel, Hermann Luyken, Michael Bartsch, Robert Baumann, Gerd Haderlein
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Patent number: 7067685Abstract: 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 2Type: GrantFiled: October 4, 2002Date of Patent: June 27, 2006Assignee: BASF AktiengesellschaftInventors: Michael Bartsch, Robert Baumann, Dagmar Pascale Kunsmann-Keitel, Gerd Haderlein, Tim Jungkamp, Marco Altmayer, Wolfgang Siegel, Ferenc Molnar
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Patent number: 6936171Abstract: 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: GrantFiled: January 8, 2003Date of Patent: August 30, 2005Assignee: Invista North America S.a.r.l.Inventors: Scott C. Jackson, Ronald J. Mckinney
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Patent number: 6897329Abstract: 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: GrantFiled: January 14, 2003Date of Patent: May 24, 2005Assignee: Invista North America S.A.R.L.Inventors: Scott C. Jackson, Ronald J. McKinney
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Patent number: 6852661Abstract: 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: GrantFiled: March 23, 2000Date of Patent: February 8, 2005Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Heiko Maas, Michael Röper
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Patent number: 6812352Abstract: 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: GrantFiled: April 9, 2002Date of Patent: November 2, 2004Assignee: Invista North America S.a.r.l.Inventors: Kristina Ann Kreutzer, Wilson Tam, J. Michael Garner, John Ronald Boyles
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Publication number: 20040138494Abstract: 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: ApplicationFiled: January 14, 2003Publication date: July 15, 2004Inventors: Scott C. Jackson, Ronald J. McKinney
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Patent number: 6737539Abstract: 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: GrantFiled: June 4, 2003Date of Patent: May 18, 2004Assignee: E. I. DuPont de Nemours and CompanyInventors: Christian P. Lenges, Helen S. M. Lu, Joachim C. Ritter
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Patent number: 6642405Abstract: 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: GrantFiled: April 10, 2002Date of Patent: November 4, 2003Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kunio Mori, Yutaka Sasaki, Kenichi Miyaki, Hirokazu Watanabe
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Publication number: 20030195372Abstract: 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: ApplicationFiled: June 4, 2003Publication date: October 16, 2003Inventors: Christian P. Lenges, Helen S. M. Lu, Joachim C. Ritter
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Patent number: 6521778Abstract: 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: GrantFiled: November 30, 2000Date of Patent: February 18, 2003Assignee: BASF AktiengesellschaftInventors: Jakob Fischer, Wolfgang Siegel, Dagmar Pascale Keitel, Lorenz Siggel
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Publication number: 20030023110Abstract: 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: ApplicationFiled: April 9, 2002Publication date: January 30, 2003Inventors: Wilson Tam, J. Michael Garner, John Ronald Boyles
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Publication number: 20030018208Abstract: 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: ApplicationFiled: August 22, 2002Publication date: January 23, 2003Inventors: Sanjay Chaturvedi, Anne Mae Gaffney, Scott Han, Michele Doreen Hefener, Ruozhi Song
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Patent number: 6486359Abstract: 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: GrantFiled: December 12, 2000Date of Patent: November 26, 2002Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Rocco Paciello, Michael Röper, Jakob Fischer
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Patent number: 6469194Abstract: 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: GrantFiled: June 22, 2001Date of Patent: October 22, 2002Assignee: Rhodia Fiber & Resin IntermediatesInventors: Paolo Burattin, Pierre Coqueret, Marc Huser
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Patent number: 6380421Abstract: 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: GrantFiled: August 30, 2000Date of Patent: April 30, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Helen S. M. Lu, Nora Radu
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Publication number: 20020026066Abstract: 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: ApplicationFiled: June 22, 2001Publication date: February 28, 2002Inventors: Paolo Burattin, Pierre Coqueret, Marc Huser
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Publication number: 20020022736Abstract: 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: ApplicationFiled: June 22, 2001Publication date: February 21, 2002Inventors: Paolo Burattin, Pierre Coqueret, Marc Huser
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Patent number: 6242633Abstract: 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: GrantFiled: March 7, 2000Date of Patent: June 5, 2001Assignee: BASF AktiengesellschaftInventors: Jakob Fischer, Wolfgang Siegel
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Patent number: 6197992Abstract: 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: GrantFiled: June 14, 1999Date of Patent: March 6, 2001Assignee: BASF AktiengesellschaftInventors: Jakob Fischer, Wolfgang Siegel, Klaus Mundinger, Gerald Meyer
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Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor
Patent number: 6171996Abstract: 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: GrantFiled: July 13, 1999Date of Patent: January 9, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: James Michael Garner, Kristina Ann Kruetzer, Wilson Tam -
Patent number: 6169198Abstract: 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: GrantFiled: February 1, 2000Date of Patent: January 2, 2001Assignee: BASF AktiengesellshaftInventors: Jakob Fischer, Wolfgang Siegel
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Patent number: 6162942Abstract: A process for preparing aromatic nitriles from corresponding chloroaromatics by reaction with cyanides.Type: GrantFiled: August 17, 1999Date of Patent: December 19, 2000Assignee: Bayer AktiengesellschaftInventors: Michael-Harold Rock, Albrecht Marhold
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Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor
Patent number: 6127567Abstract: 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: GrantFiled: July 23, 1998Date of Patent: October 3, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: James Michael Garner, Kristina Ann Kruetzer, Wilson Tam -
Patent number: 6048996Abstract: 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: GrantFiled: August 26, 1999Date of Patent: April 11, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Lucy Mary Clarkson, Norman Herron, William C. Kalb, Ronald James McKinney, Edward Francis Moran, Jr.
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Patent number: 6020516Abstract: 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: GrantFiled: July 23, 1998Date of Patent: February 1, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Thomas Foo, James Michael Garner, Wilson Tam
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Patent number: 5981772Abstract: 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: GrantFiled: July 23, 1998Date of Patent: November 9, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Thomas Foo, James Michael Garner, Wilson Tam
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Patent number: 5959135Abstract: 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: GrantFiled: July 8, 1998Date of Patent: September 28, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: James Michael Garner, Wilson Tam
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Patent number: 5856555Abstract: 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: GrantFiled: April 11, 1997Date of Patent: January 5, 1999Assignee: Rhone-Poulenc Fiber & Resin IntermediatesInventors: Marc Huser, Robert Perron
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Patent number: 5847191Abstract: 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: GrantFiled: July 29, 1997Date of Patent: December 8, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio Enrique Bunel, Kenneth C. McNulty
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Patent number: 5821378Abstract: 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: GrantFiled: November 28, 1995Date of Patent: October 13, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Thomas Foo, Wilson Tam
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Patent number: 5723641Abstract: 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: GrantFiled: September 26, 1996Date of Patent: March 3, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Wilson Tam, Kristina Ann Kreutzer, Ronald James McKinney
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Patent number: 5693843Abstract: 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: GrantFiled: December 22, 1995Date of Patent: December 2, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Anne Irisa Breikss, Thomas Foo
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Patent number: 5688986Abstract: 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: GrantFiled: April 26, 1995Date of Patent: November 18, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Wilson Tam, Kristina Ann Kreutzer, Ronald James McKinney
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Patent number: 5543536Abstract: 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: GrantFiled: April 26, 1994Date of Patent: August 6, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Wilson Tam
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Patent number: 5523453Abstract: 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: GrantFiled: March 22, 1995Date of Patent: June 4, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Anne I. Breikss
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Patent number: 5512695Abstract: 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: GrantFiled: March 7, 1995Date of Patent: April 30, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Kristina A. Kreutzer, Wilson Tam
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Patent number: 5512696Abstract: 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: GrantFiled: July 21, 1995Date of Patent: April 30, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Kristina A. Kreutzer, Wilson Tam
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Patent number: 5510470Abstract: 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: GrantFiled: April 19, 1995Date of Patent: April 23, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Albert L. Casalnuovo, Thaliyil V. Rajanbabu
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Patent number: 5488129Abstract: 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: GrantFiled: November 3, 1994Date of Patent: January 30, 1996Assignee: Rhone-Poulenc ChimieInventors: Marc Huser, Robert Perron
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Patent number: 5449807Abstract: 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: GrantFiled: November 18, 1994Date of Patent: September 12, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joe D. Druliner
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Patent number: 5312957Abstract: 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: GrantFiled: October 15, 1992Date of Patent: May 17, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Albert L. Casalnuovo, Thaliyil V. Rajanbabu, Lawrence W. Gosser, Ronald J. McKinney, Nugent, Jr. William A.
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Patent number: 5175335Abstract: 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: GrantFiled: November 12, 1991Date of Patent: December 29, 1992Assignee: E. I. du Pont de Nemours and CompanyInventors: Albert L. Casalnuovo, Thaliyil V. Rajanbabu, Lawrence W. Gosser, Ronald J. McKinney, William A. Nugent, Jr.
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Patent number: 5169971Abstract: 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: GrantFiled: May 6, 1992Date of Patent: December 8, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masamitu Inomata, Naokazu Shiotani, Kazuo Koshizuka, Minato Karasawa
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Patent number: 5143873Abstract: 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: GrantFiled: December 17, 1990Date of Patent: September 1, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Henry E. Bryndza, Albert L. Casalnuovo
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Patent number: 5107012Abstract: 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: GrantFiled: April 24, 1991Date of Patent: April 21, 1992Assignee: E. I. du Pont de Nemours and CompanyInventor: Gerald C. Grunewald