Organic Material Which Contains Phosphorus, Arsenic, Or Antimony, In Addition To Nickel, Utilized (e.g., Zero-valent Nickel Complexes, Etc.) Patents (Class 558/338)
  • Patent number: 10143999
    Abstract: Disclosed are nickel-containing complexation precursors having high complexation activity for bidentate phosphite ligands. Also disclosed are methods of making the complexation precursors. The disclosed method of generating the nickel-containing complexation precursor includes including contacting a nickel starting material with a reductant under conditions sufficient to generate a nickel-containing complexation precursor having at least about 1,500 ppmw sulfur in the form of sulfide.
    Type: Grant
    Filed: November 11, 2015
    Date of Patent: December 4, 2018
    Assignee: INVISTA NORTH AMERICA S.A R.L.
    Inventors: Joan Fraga-Dubreuil, Vinay Medhekar, John A. Turner, Keith Whiston
  • Patent number: 9994802
    Abstract: Cleaning industrial plant components to remove silane, metal halide, and organometallic halide contaminants and mixtures thereof, involves treating the plant components with a liquid nitrile or amine or mixture thereof or with a solution of a nitrile or amine or mixture thereof in an aprotic solvent.
    Type: Grant
    Filed: March 25, 2015
    Date of Patent: June 12, 2018
    Assignee: WACKER CHEMIE AG
    Inventors: Javad Mohsseni, Konrad Mautner, Peter Nuernberg, Christian Kaltenmarkner, Klaus Kaeppler, Andreas Bockholt
  • Patent number: 9687835
    Abstract: In the hydrocyanation reaction of butadiene proceeding through pentenenitriles to adiponitrile, catalysis by complexes of zerovalent nickel with bidentate phosphorus-based ligands of the NiL2A type wherein L2 is a bidentate ligand and A is an unsaturated compound, can be rate-limited by the solubility of the catalytic complex. The present invention concerns solvent compositions for the nickel-ligand complex comprising mixtures of unsaturated nitriles that provide for increased metal solubility, particularly in the absence of a Lewis acid promoter, resulting in higher hydrocyanation reaction rates in an industrial-scale process for production of important nylon manufacturing intermediates. The mixed nitrile solvent compositions can include mixtures of pentenenitriles and/or methylbutenenitriles. The mixtures of mixed unsaturated nitriles can be, at least in part, from recycle streams from the hydrocyanation reaction for which the nickel-bidentate ligand complexes are used as catalysts.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: June 27, 2017
    Assignee: INVISTA NORTH AMERICA S.A.R.L.
    Inventor: Thomas E. Vos
  • Patent number: 9371346
    Abstract: The present invention relates to a method of preparing a nickel complex including nickel and at least one phosphorus-containing ligand by reacting at least a portion of a nickel metal with at least one phosphorus-containing ligand. The nickel metal is prepared from a nickel composition including nickel(II).
    Type: Grant
    Filed: June 13, 2011
    Date of Patent: June 21, 2016
    Assignee: INVISTA North America S.a.r.l.
    Inventor: John J. Ostermaier
  • Patent number: 9233917
    Abstract: A process for the hydrocyanation of a hydrocarbon-based compound having at least one site of ethylenic unsaturation into a nitrile compound includes reaction thereof, in a liquid medium, with hydrogen cyanide in the presence of a catalyst containing a metal element selected from among the transition metals and an organophosphorus ligand, wherein the organophosphorus ligand is a mixture of at least one monodentate organophosphite compound and at least one monodentate organophosphine compound; the subject process is especially useful for the synthesis of adiponitrile from butadiene.
    Type: Grant
    Filed: June 5, 2009
    Date of Patent: January 12, 2016
    Assignee: INVISTA NORTH AMERICA S.A R.L.
    Inventor: Sergio Mastroianni
  • Patent number: 9061970
    Abstract: Compounds containing at least one nitrile functional group are produced by hydrocyanation of an organic compound having at least one site of non-conjugated unsaturation, having from 2 to 20 carbon atoms, by reaction with hydrogen cyanide in the presence of a catalytic system containing a complex of nickel having the oxidation state of zero with at least one organophosphorus ligand selected from the group consisting of organophosphites, organophosphonites, organophosphinites and organosphosphines and a cocatalyst of the Lewis acid type of formula: in which M1 and M2 are each elements selected from the group consisting of zinc, boron, aluminum, cadmium, gallium, indium and tin.
    Type: Grant
    Filed: January 12, 2009
    Date of Patent: June 23, 2015
    Assignee: INVISTA North America S.a.r.l.
    Inventor: Sergio Mastroianni
  • Patent number: 9040735
    Abstract: The present invention relates to a process for hydrocyanating 3-pentenenitrile. The process can include feeding 3-pentenenitrile and HCN to a hydrocyanation reaction zone that includes a Lewis acid promoter, nickel, and a phosphorus-containing ligand. In various embodiments, the process can also include controlling water concentration within the hydrocyanation reaction zone sufficient to maintain a high activity of the ligand catalyst complex while recycling at least a portion of the ligand catalyst complex.
    Type: Grant
    Filed: October 4, 2012
    Date of Patent: May 26, 2015
    Assignee: INVISTA North America S.a.r.l.
    Inventors: Sudhir Aki, Wyatte E. Allen, Mark Anstrom, Charles Nelson Campbell, II, Tseng Chao, James E. McIntosh, Larry E. Moerbe, Bruce Edwin Murphree, Mark D. Rogers, William J. Tenn, III, Thomas E. Vos, Michael W. Wensing
  • Patent number: 9040734
    Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. The reaction of 1,3-butadiene with hydrogen cyanide to produce 3-pentenenitrile also produces small amounts of dinitrile compounds, including adiponitrile (ADN) and methylglutaronitrile (MGN). Methylglutaronitrile is removed to provide an adiponitrile-enriched stream, which is used in a catalyst purification step.
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: May 26, 2015
    Assignee: INVISTA North America S.a r.l.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Patent number: 9024049
    Abstract: Nickel(II) compositions for use in manufacturing nickel metal (Ni(0)) compositions, and specifically to methods of making basic nickel carbonates used to produce nickel metal compositions are disclosed. By varying the molar ratios of carbonates and bicarbonates to nickel salts, the methods provide basic nickel carbonates that produce superior nickel metal-containing solids that are well-suited to forming nickel-ligand complexes with phosphorus-containing ligands. The phosphorus-containing ligands can be monodentate or bidentate phosphorus-containing ligands.
    Type: Grant
    Filed: June 13, 2011
    Date of Patent: May 5, 2015
    Assignee: INVISTA North America S.a.r.l.
    Inventor: John J. Ostermaier
  • Patent number: 8937198
    Abstract: A hydrocyanation reaction is used to react 1,3-butadiene with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles, as well as reaction byproducts, such as methylglutaronitrile (MGN). The effluent from the hydrocyanation reaction is distilled in a particular manner to produce a pentenenitrile-enriched stream, a catalyst-enriched stream and a stream enriched in methylglutaronitrile (MGN). At least a portion of the catalyst enriched stream may be recycled to the hydrocyanation reaction. 3-pentenenitrile may be recovered and, optionally, further reacted with HCN to make adiponitrile (ADN).
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: January 20, 2015
    Assignee: INVISTA North America S.a.r.l.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20140235887
    Abstract: The present invention relates to a process for hydrocyanating 3-pentenenitrile. The process can include feeding 3-pentenenitrile and HCN to a hydrocyanation reaction zone that includes a Lewis acid promoter, nickel, and a phosphorus-containing ligand. In various embodiments, the process can also include controlling water concentration within the hydrocyanation reaction zone sufficient to maintain a high activity of the ligand catalyst complex while recycling at least a portion of the ligand catalyst complex.
    Type: Application
    Filed: October 4, 2012
    Publication date: August 21, 2014
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: Sudhir Aki, Wyatte E. Allen, Mark Anstrom, Charles Nelson Campbell, Tseng Chao, James E. Mcintosh, Larry E. Moerbe, Bruce Edwin Murphree, Mark D. Rogers, William J. Tenn, Thomas E. Vos, Michael W. Wensing
  • Patent number: 8772527
    Abstract: The present invention relates to an improved process for batchwise or continuous isomerization of cis-2-pentenenitrile to 3-pentenenitriles in the presence of 1,4-diazabicyclo[2.2.2]octane as catalyst.
    Type: Grant
    Filed: April 22, 2013
    Date of Patent: July 8, 2014
    Assignee: BASF SE
    Inventors: Rolf-Hartmuth Fischer, Alfred Oftring, Robert Baumann, Hermann Luyken
  • Publication number: 20130289299
    Abstract: The present invention relates to an improved process for batchwise or continuous isomerization of cis-2-pentenenitrile to 3-pentenenitriles in the presence of 1,4-diazabicyclo[2.2.2]octane as catalyst.
    Type: Application
    Filed: April 22, 2013
    Publication date: October 31, 2013
    Applicant: BASF SE
    Inventors: Rolf-Hartmuth Fischer, Alfred Oftring, Robert Baumann, Hermann Luyken
  • Publication number: 20130267728
    Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. Both reactions take place in the presence of a catalyst comprising zero valent nickel and a phosphorus-containing ligand. The ligand is partially degraded by hydrolysis or oxidation. Phosphorus-containing ligand degradation products are removed during the production of 3-pentenenitrile and adiponitrile.
    Type: Application
    Filed: June 16, 2011
    Publication date: October 10, 2013
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20130211126
    Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. The reaction of 1,3-butadiene with hydrogen cyanide to produce 3-pentenenitrile also produces small amounts of dinitrile compounds, including adiponitrile (ADN) and methylglutaronitrile (MGN). Methylglutaronitrile is removed to provide an adiponitrile-enriched stream, which is used in a catalyst purification step.
    Type: Application
    Filed: June 16, 2011
    Publication date: August 15, 2013
    Applicant: INVISTA NORTH AMERICA S.A.R.L.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20130211127
    Abstract: An improved multi-reaction zone process provides improved nitrile product quality and yield. In a first reaction zone, 1,3-butadiene is reacted with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles comprising 3-pentenenitrile and 2-methyl-3-butenenitrile. In a second reaction zone, 2-methyl-3-butenenitrile, recovered from the first reaction zone, is isomerized to 3-pentenenitrile. In a third reaction zone, 3-pentenenitrile recovered from the first and second reaction zones is reacted with hydrogen cyanide in the presence of a catalyst and a Lewis acid to produce adiponitrile. Unwanted production and build-up of dinitriles, including methylglutaronitrile, in the first reaction zone for the hydrocyanation of 1,3-butadiene is prevented by limiting the flow of Lewis acid into the first reaction zone.
    Type: Application
    Filed: June 16, 2011
    Publication date: August 15, 2013
    Applicant: INVISTA NORTH AMERICA S.A.R.L. Three Little Falls Centre
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20130211125
    Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The 1,3-butadiene feed includes a small amount of tertiary-butylcatechol. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process.
    Type: Application
    Filed: June 16, 2011
    Publication date: August 15, 2013
    Applicant: INVISTA NORTH AMERICA S.A.R.L.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20130150610
    Abstract: A hydrocyanation reaction is used to react 1,3-butadiene with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles, as well as reaction byproducts, such as methylglutaronitrile (MGN). The effluent from the hydrocyanation reaction is distilled in a particular manner to produce a pentenenitrile-enriched stream, a catalyst-enriched stream and a stream enriched in methylglutaronitrile (MGN). At least a portion of the catalyst enriched stream may be recycled to the hydrocyanation reaction. 3-pentenenitrile may be recovered and, optionally, further reacted with HCN to make adiponitrile (ADN).
    Type: Application
    Filed: June 16, 2011
    Publication date: June 13, 2013
    Applicant: INVISTA NORTH AMERICA S.A.R.L.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20130144082
    Abstract: A novel nickel particulate form is provided that efficiently forms a zero-valent nickel complex with a phosphorus-containing ligands in an organic liquid to form a hydrocyanation catalyst. Particles in the nickel particulate form comprise nickel crystallites. For example, the nickel particulate form can have a BET Specific Surface Area of at least about 1 m2/gm; an average crystallite size less than about 20-25 nm, the nickel particulate form can have at least 10% of the crystallites in the nickel form can have can have a diameter (C10) of less than about 10 nm, and/or there are on average at least about 1015 surface crystallites per gram nickel. A ratio of BET SSA to C50 for the nickel particulate form can be at least about 0.1×109 m/gm and preferably at least about 0.4×109 m/gm. Methods of preparation and use are also provided.
    Type: Application
    Filed: June 6, 2012
    Publication date: June 6, 2013
    Applicant: INVISTA North America S.a r.l.
    Inventors: Joan Fraga-Dubreuil, Vinay Medhekar, Thomas A. Micka, Keith Whiston
  • Patent number: 8394981
    Abstract: The invention provides a process for hydrocyanation, comprising: contacting 2-pentenenitrile with hydrogen cyanide 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: Grant
    Filed: February 7, 2011
    Date of Patent: March 12, 2013
    Assignee: Invista North America S.A R.L.
    Inventors: James Michael Garner, Christian P. Lenges, Ronald J. McKinney, Wilson Tam
  • Publication number: 20120035387
    Abstract: The invention provides a process for hydrocyanation, comprising: contacting 2-pentenenitrile with hydrogen cyanide 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: February 7, 2011
    Publication date: February 9, 2012
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: James Michael Garner, Christian P. Lenges, Ronald J. McKinney, Wilson Tam
  • Patent number: 8088943
    Abstract: The invention provides a hydrocyanation process to produce adiponitrile and other dinitriles having six carbon atoms, in the presence of catalyst composition comprising a zero-valent nickel and at least one bidentate phosphorus-containing ligand wherein the bidentate phosphorus-containing ligand gives acceptable results according to at least one protocol of the 2-Pentenenitrile Hydrocyanation Test Method.
    Type: Grant
    Filed: January 14, 2009
    Date of Patent: January 3, 2012
    Assignee: Invista North America S.A R.L.
    Inventors: Thomas Foo, James Michael Garner, Ron Ozer, Paul S. Pearlman
  • Publication number: 20110288327
    Abstract: A method for producing compounds including at least one nitrile function by the hydrocyanation of a compound including at least one non-conjugated unsaturation is described. A method for producing compounds including at least one nitrile function by the hydrocyanation of an organic compound including at least one non-conjugated unsaturation including 2 to 20 carbon atoms by reacting with hydrogen cyanide in the presence of a catalytic system including at least one nickel complex in a zero oxidation state with at least one organophosphorus ligand selected from the group including organophosphites, organophosphonites, organophosphinites and organosphosphines and a co-catalyst such as a Lewis acid consisting of a mixture of Lewis acids is also described.
    Type: Application
    Filed: January 18, 2010
    Publication date: November 24, 2011
    Applicant: RHODIA OPERATIONS
    Inventor: Sergio Mastroianni
  • Patent number: 8039660
    Abstract: The present invention relates to the manufacture of nitrile compounds from unsaturated organic compounds by reaction with hydrogen cyanide. It relates more particularly to the manufacture of nitrile compounds of use in the synthesis of adiponitrile, an important chemical intermediate in the manufacture of major chemical compounds, such as hexamethylenediamine and ?-caprolactam. The invention provides a process for the manufacture of organic compounds comprising at least one nitrile functional group by carrying out a hydrocyanation reaction between hydrogen cyanide and an organic compound comprising at least one ethylenic unsaturation. This reaction is carried out in the presence of a catalytic system comprising a metal element chosen from the group consisting of nickel, platinum and palladium and an organophosphorus ligand, the reaction medium additionally comprising an ionic liquid in the liquid state at least at the temperature at which the hydrocyanation reaction is carried out.
    Type: Grant
    Filed: October 2, 2008
    Date of Patent: October 18, 2011
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Jean-Marie Basset, Yves Chauvin, Jean-Christophe Galland, Gerald Niccolai, Christine Valerio, Christophe Vallee
  • Publication number: 20110196168
    Abstract: Nickel-metal-containing solids for use in manufacturing nickel metal complexes are disclosed. The nickel-metal-containing solids are made by reducing basic nickel carbonates. By varying the molar ratios of carbonates and bicarbonates to nickel salts, the methods provide basic nickel carbonates that produce superior nickel metal-containing solids that react more effectively with phosphorous-containing ligands. The phosphorous containing ligands can be both monodentate and bidentate phosphorous-containing ligands.
    Type: Application
    Filed: December 15, 2010
    Publication date: August 11, 2011
    Applicant: INVISTA NORTH AMERICA S.A. R.L.
    Inventor: JOHN J. OSTERMAIER
  • Patent number: 7977502
    Abstract: The invention provides an integrated, continuous process for the production of 3-pentenenitrile, the refining of 3-pentenenitrile, and the refining of 2-methyl-3-butenenitrile, the process comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a butadiene-containing feed, and a catalyst composition, wherein the catalyst composition comprises a zero-valent nickel and at least one bidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, a mixed phosphorus-containing ligand, and combination thereof; (b) maintaining a residence time in the reaction zone sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the reaction mixture; (c) distilling the reaction mixture to obtain a first stream compr
    Type: Grant
    Filed: January 14, 2009
    Date of Patent: July 12, 2011
    Assignee: Invista North America S.A R.L.
    Inventors: Thomas Foo, Sigridur S. Kristjansdottir, Ronald J. McKinney, Ron Ozer, Paul S. Pearlman
  • Publication number: 20110166376
    Abstract: A process for the hydrocyanation of a hydrocarbon-based compound having at least one site of ethylenic unsaturation into a nitrile compound includes reaction thereof, in a liquid medium, with hydrogen cyanide in the presence of a catalyst containing a metal element selected from among the transition metals and an organophosphorus ligand, wherein the organophosphorus ligand is a mixture of at least one monodentate organophosphite compound and at least one monodentate organophosphine compound; the subject process is especially useful for the synthesis of adiponitrile from butadiene.
    Type: Application
    Filed: June 5, 2009
    Publication date: July 7, 2011
    Applicant: RHODIA OPERATIONS
    Inventor: Sergio Mastroianni
  • Patent number: 7935229
    Abstract: A process for extractively removing homogeneously dissolved catalysts from a reaction effluent of a hydrocyanation of unsaturated mononitriles to dinitriles with a hydrocarbon H, including performing the steps of a) concentrating the reaction effluent before step b) by distillation at pressures of from 0.1 to 5000 mbar and temperatures of from 10 to 150° C., b) adding a hydrocarbon H to the concentrated reaction effluent to obtain a stream I, and c) feeding stream I, without prior separation of the liquid phases, into an extraction apparatus and extracting it at a temperature T with the hydrocarbon H to obtain a stream II comprising the hydrocarbon H enriched with the catalyst and a stream III having a low catalyst content.
    Type: Grant
    Filed: October 12, 2005
    Date of Patent: May 3, 2011
    Assignee: BASF SE
    Inventors: Petra Deckert, Peter Bassler, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel, Peter Pfab, Tobias Aechtner, Wolfgang Siegel
  • Patent number: 7919646
    Abstract: The invention provides a process for hydrocyanation, comprising: contacting 2-pentenenitrile with hydrogen cyanide 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: Grant
    Filed: July 12, 2007
    Date of Patent: April 5, 2011
    Assignee: Invista North America S.A R.L.
    Inventors: James Michael Garner, Christian P. Lenges, Ronald J. McKinney, Wilson Tam
  • Patent number: 7880028
    Abstract: The invention provides a continuous process for the production of 3-pentenenitrile, comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a 1,3-butadiene-containing feed, and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one multidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, and a mixed phosphorus-containing ligand or a combination of such members; and (b) maintaining a residence time sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the reaction mixture.
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: February 1, 2011
    Assignee: Invista North America S.A R.L.
    Inventors: Thomas Foo, Sigridur S. Kristjansdottir, Ronald J. McKinney, Ron Ozer, Paul S. Pearlman
  • Patent number: 7816551
    Abstract: An adiponitrile/methylglutaronitrile preparation process includes distilling a reaction stream to obtain stream 3 depleted in pentenenitriles (bottom product) and stream 4 enriched in pentenenitriles (top product); extracting stream 3 obtaining stream 6 enriched with extractant (top product) and stream 7 depleted in extractant (bottom product); distilling stream 6 obtaining stream 8 comprising the catalyst (bottom product) and stream 9 comprising the extractant (top product); distilling stream 7 obtaining stream 10 (bottom product) and stream 11 comprising the extractant (top product); distilling stream 10 obtaining stream 12 comprising catalyst degradation products, at least one promotor, adiponitrile and methylglutaronitrile (bottom product) and stream 13 comprising pentenenitriles (top product); distilling stream 12 obtaining stream 14 comprising catalyst degradation products and the promotor(s) (bottom product) and stream 15 comprising adiponitrile and methylglutaronitrile (top product); distilling stream
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: October 19, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Tim Jungkamp, Robert Baumann, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel
  • Patent number: 7709675
    Abstract: A process is described for continuously hydrocyanating 1,3-butadiene in the presence of at least one nickel(0) catalyst with chelate ligands, wherein 1,3-butadiene and hydrogen cyanide are used in a molar ratio of from 1.6:1 to 1.1:1.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: May 4, 2010
    Assignee: BASF SE
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Jens Scheidel, Tim Jungkamp, Hermann Luyken
  • Patent number: 7709674
    Abstract: A hydrocyanation process produces adiponitrile and other dinitriles having six carbon atoms. The process involves forming a reaction mixture in the presence of at least one Lewis acid. The reaction mixture includes ethylenically unsaturated nitrites having five carbon atoms, hydrogen cyanide, and a catalyst precursor compositions. The reaction mixture is continuously fed while controlling the overall feed molar ratio of 2-pentenenitriles to all unsaturated nitriles and the overall feed molar ratio of hydrogen cyanide to all unsaturated nitrites. In the reaction product mixture, including adiponitrile, the ratio of the concentration of 2-pentenenitriles to the concentration of 3-pentenenitriles from about 0.2/1 to about 10/1. Included in the catalyst precursor composition is a zero-valent nickel and at least one multidentate phosphorus-containing ligand.
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: May 4, 2010
    Assignee: Invista North America S.A R.L
    Inventors: Thomas Foo, James Michael Garner, Ron Ozer, Paul S. Pearlman
  • Patent number: 7687655
    Abstract: The present invention relates to a process for the manufacture of dinitrile compounds by double hydrocyanation of an olefin. It relates particularly to a process for the manufacture of dinitrile compounds by double hydrocyanation of an olefin present in a mixture of hydrocarbons, such as a petroleum fraction and more particularly still a petroleum fraction known under the name of C4 fraction. The process of the invention comprises a sequence of stages for the separation of the various compounds which makes it possible to remove the byproducts, such as the products from the trimerization of alkynes, present in the C4 fraction and thus to prevent their accumulation in the hydrocyanation reactors.
    Type: Grant
    Filed: November 30, 2005
    Date of Patent: March 30, 2010
    Assignee: Rhodia Chimie
    Inventors: Philippe Leconte, Beatrice Barateau
  • Patent number: 7671229
    Abstract: A process is described for hydrocyanating 1,3-butadiene over at least one nickel(0) complex having phosphorus ligands as a catalyst, wherein the 1,3-butadiene is used in a mixture with n-butane and the mixture contains from 60 to 90% by volume of 1,3-butadiene and from 40 to 10% by volume of n-butane.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: March 2, 2010
    Assignee: BASF SE
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Götz-Peter Schindler, Tim Jungkamp, Hermann Luyken, Jens Scheidel, Andreas Brodhagen
  • Patent number: 7659422
    Abstract: A hydrocyanation process produces adiponitrile and other dinitriles having six carbon atoms. The process involves forming a reaction mixture in the presence of at least one Lewis acid. The reaction mixture includes ethylenically unsaturated nitriles having five carbon atoms, hydrogen cyanide, and a catalyst precursor composition. The reaction mixture is continuously fed while controlling the overall feed molar ratio of 2-pentenenitriles to all unsaturated nitriles and the overall feed molar ratio of hydrogen cyanide to all unsaturated nitriles. In the reaction product mixture, including adiponitrile, the ratio of the concentration of 2-pentenenitriles to the concentration of 3-pentenenitriles is from about 0.2/1 to about 10/1. Included in the catalyst precursor composition is a zero-valent nickel and at least one bidentate phosphite ligand.
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: February 9, 2010
    Assignee: Invista North America S.A.R.L.
    Inventors: Thomas Foo, James Michael Garner, Ron Ozer
  • Publication number: 20090247780
    Abstract: The present invention relates to the manufacture of nitrile compounds from unsaturated organic compounds by reaction with hydrogen cyanide. It relates more particularly to the manufacture of nitrile compounds of use in the synthesis of adiponitrile, an important chemical intermediate in the manufacture of major chemical compounds, such as hexamethylenediamine and ?-caprolactam. The invention provides a process for the manufacture of organic compounds comprising at least one nitrile functional group by carrying out a hydrocyanation reaction between hydrogen cyanide and an organic compound comprising at least one ethylenic unsaturation. This reaction is carried out in the presence of a catalytic system comprising a metal element chosen from the group consisting of nickel, platinum and palladium and an organophosphorus ligand, the reaction medium additionally comprising an ionic liquid in the liquid state at least at the temperature at which the hydrocyanation reaction is carried out.
    Type: Application
    Filed: October 2, 2008
    Publication date: October 1, 2009
    Applicant: RHODIA POLYAMIDE INTERMEDIATES
    Inventors: Jean-Marie BASSET, Yves Chauvin, Jean-Christophe Galland, Gerald Niccolai, Christine Valerio, Christophe Vallee
  • Publication number: 20090198082
    Abstract: The present invention is to provide a process for producing dicyanonorbornane characterized by causing hydrogen cyanide to undergo addition reaction with cyanonorbornene (bicyclo[2.2.1]-5-heptene-2-carbonitrile) in the presence of a zerovalent nickel complex catalyst which is produced by using a phosphite represented by P(x)(y)(z) (wherein P is a phosphorus atom, and x, y and z are each OR, where R represents an aryl group having not more than 18 carbon atoms) as a ligand to reduce a nickel halide with at least one metal selected among zinc, cadmium, beryllium, aluminum, iron and cobalt, wherein the phosphite is one which has a phosphate content of 1.0 weight % or lower based on the whole phosphite.
    Type: Application
    Filed: June 22, 2007
    Publication date: August 6, 2009
    Applicant: MITSUI CHEMICALS , INC.
    Inventors: Norihiko Fukatsu, Hiroyuki Morijiri, Chitoshi Shimakawa, Koichi Tokunaga, Seiichi Kobayashi
  • Publication number: 20090182163
    Abstract: The invention provides an integrated, continuous process for the production of 3-pentenenitrile, the refining of 3-pentenenitrile, and the refining of 2-methyl-3-butenenitrile, the process comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a butadiene-containing feed, and a catalyst composition, wherein the catalyst composition comprises a zero-valent nickel and at least one bidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, a mixed phosphorus-containing ligand, and combination thereof; (b) maintaining a residence time in the reaction zone sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the reaction mixture; (c) distilling the reaction mixture to obtain a first stream compr
    Type: Application
    Filed: January 14, 2009
    Publication date: July 16, 2009
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: THOMAS FOO, Sigridur S. Kristjansdottir, Ronald J. McKinney, Ron Ozer, Paul S. Pearlman
  • Publication number: 20090182164
    Abstract: The invention provides a hydrocyanation process to produce adiponitrile and other dinitriles having six carbon atoms, in the presence of catalyst composition comprising a zero-valent nickel and at least one bidentate phosphorus-containing ligand wherein the bidentate phosphorus-containing ligand gives acceptable results according to at least one protocol of the 2-Pentenenitrile Hydrocyanation Test Method.
    Type: Application
    Filed: January 14, 2009
    Publication date: July 16, 2009
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: Thomas Foo, James Michael Garner, Ron Ozer, Paul S. Pearlman
  • Publication number: 20090099386
    Abstract: The present invention relates to a process for the manufacture of dinitrile compounds by double hydrocyanation of an olefin. It relates particularly to a process for the manufacture of dinitrile compounds by double hydrocyanation of an olefin present in a mixture of hydrocarbons, such as a petroleum fraction and more particularly still a petroleum fraction known under the name of C4 fraction. The process of the invention comprises a sequence of stages for the separation of the various compounds which makes it possible to remove the byproducts, such as the products from the trimerization of alkynes, present in the C4 fraction and thus to prevent their accumulation in the hydrocyanation reactors.
    Type: Application
    Filed: November 30, 2005
    Publication date: April 16, 2009
    Applicant: Rhodia Chimie
    Inventors: Philippe Leconte, Beatrice Barateau
  • Patent number: 7462263
    Abstract: A process for dewatering hydrocyanic acid by distillation, which includes distilling crude hydrocyanic acid containing from 50 to 99.9% by weight of HCN, from 0.1 to 40% by weight of water, from 0 to 15% by weight of carbon oxides and optionally from 0.01 to 1% by weight of an involatile stabilizer, at a pressure of from 1 bar to 2.5 bar, a bottom temperature of from 100° C. to 130° C. and a top temperature of from 25° C. to 54° C., in the absence of a volatile stabilizer, in a distillation column to obtain a top draw stream containing purified, anhydrous hydrocyanic acid and carbon oxides and a bottom draw stream including water and, optionally, the involatile stabilizer.
    Type: Grant
    Filed: April 15, 2004
    Date of Patent: December 9, 2008
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Miquel Angel Flores, Tim Jungkamp, Hermann Luyken, Jens Scheidel, Wolfgang Siegel, Dagmar Pascale Kunsmann-Keitel, Peter Bassler
  • Publication number: 20080275266
    Abstract: A process is described for hydrocyanating 1,3-butadiene over at least one nickel(0) complex having phosphorus ligands as a catalyst, wherein the 1,3-butadiene is used in a mixture with n-butane and the mixture contains from 60 to 90% by volume of 1,3-butadiene and from 40 to 10% by volume of n-butane.
    Type: Application
    Filed: January 27, 2005
    Publication date: November 6, 2008
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Gotz-Peter Schindler, Tim Jungkamp, Hermann Luyken, Jens Scheidel, Andreas Brodhagen
  • Patent number: 7442825
    Abstract: The present invention concerns a process for hydrocyanating ethylenically unsaturated organic compounds to compounds containing at least one nitrile function. It relates more particularly to the hydrocyanation of diolefins such as butadiene or of substituted olefins such as alkenenitriles, for instance pentenenitriles. According to the process of the invention the reaction is implemented in the presence of a metal complex catalyst comprising a transition metal such as nickel and an organic ligand.
    Type: Grant
    Filed: July 11, 2003
    Date of Patent: October 28, 2008
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Jean-Christophe Galland, Blaise Didillon, Philippe Marion, Damien Bourgeois
  • Patent number: 7439381
    Abstract: A process is described for preparing 3-pentenenitrile by hydrocyanating 1,3-butadiene with hydrogen cyanide over at least one catalyst, wherein the 1,3-butadiene and/or hydrogen cyanide is contacted with at least one microporous solid before the reaction.
    Type: Grant
    Filed: January 26, 2005
    Date of Patent: October 21, 2008
    Assignee: BASF SE
    Inventors: Tim Jungkamp, Dagmar Pascale Kunsmann-Keitel, Michael Bartsch, Robert Baumann, Gerd Haderlein, Hermann Luyken, Jens Scheidel
  • Publication number: 20080242886
    Abstract: A process is described for continuously hydrocyanating 1,3-butadiene in the presence of at least one nickel(0) catalyst with chelate ligands, wherein 1,3-butadiene and hydrogen cyanide are used in a molar ratio of from 1.6:1 to 1.1:1.
    Type: Application
    Filed: January 27, 2005
    Publication date: October 2, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Jens Scheidel, Tim Jungkamp, Hermann Luyken
  • Publication number: 20080227214
    Abstract: A process is described for preparing 3-pentenenitrile by hydrocyanating 1,3-butadiene in the presence of at least one catalyst, wherein unhydrocyanated 1,3-butadiene is removed from the effluent of the hydrocyanation and recycled into the process, and the recycled 1,3-butadiene is monitored for the content of hydrogen cyanide.
    Type: Application
    Filed: January 26, 2005
    Publication date: September 18, 2008
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Tim Jungkamp, Robert Baumann, Thorsten Schroder, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel
  • Patent number: 7385071
    Abstract: Process for hydrocyanating a substrate selected from 2-, 3-, or 4-pentenenitrile and/or 2-methyl-3-butenenitrile or mixtures thereof by contacting the substrate with HCN in the presence of a zero-valent nickel catalyst and a promoter that is obtained as a byproduct of titanium ore chlorination.
    Type: Grant
    Filed: October 28, 2003
    Date of Patent: June 10, 2008
    Assignee: Invista North America S.A.R.L.
    Inventors: Thomas Foo, Christian Peter Lenges
  • Publication number: 20080015380
    Abstract: The invention provides a continuous process for the production of 3-pentenenitrile, comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a 1,3-butadiene-containing feed, and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one multidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, and a mixed phosphorus-containing ligand or a combination of such members; and (b) maintaining a residence time sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the reaction mixture.
    Type: Application
    Filed: July 12, 2007
    Publication date: January 17, 2008
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventors: THOMAS FOO, Sigridur S. Kristjansdottir, Ronald J. McKinney, Ron Ozer, Paul S. Pearlman
  • 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