US20040260112A1 - Method of producing nitrile compounds - Google Patents

Method of producing nitrile compounds Download PDF

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US20040260112A1
US20040260112A1 US10/489,838 US48983804A US2004260112A1 US 20040260112 A1 US20040260112 A1 US 20040260112A1 US 48983804 A US48983804 A US 48983804A US 2004260112 A1 US2004260112 A1 US 2004260112A1
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process according
reaction
group
compounds
ionic liquid
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Jean-Marie Basset
Yves Chauvin
Jean-Christophe Galland
Gerald Niccolai
Christine Valerio
Christophe Vallee
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
    • C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/04—Preparation of carboxylic acid nitriles by reaction of cyanogen halides, e.g. ClCN, with organic compounds

Definitions

  • the present invention relates to the manufacture of nitrile compounds from unsaturated organic compounds by reaction with hydrogen cyanide.
  • 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.
  • major chemical compounds such as hexamethylenediamine and ⁇ -caprolactam.
  • the last two compounds are used in particular in the manufacture of polymers, such as polyamides, and more particularly polyamide-6 and polyamide-6,6, or other polymers, such as polyurethanes.
  • This process consists, basically, in carrying out the addition, in a first stage, of one molecule of HCN to one ethylenic unsaturation, to produce an unsaturated nitrile compound.
  • this stage leads to the production of numerous isomers of unsaturated nitrites.
  • the addition of a further molecule of HCN results, in a following stage, in a polynitrile, for example in a dinitrile, such as adiponitrile when the starting olefin is 1,3-butadiene.
  • the process comprises, after the first hydrocyanation stage, a stage known as the “isomerization stage”, which consists in converting most of the branched nitrile isomers to linear nitrile isomers, such as, in the case of the hydrocyanation of butadiene, to 3- and 4-pentenenitriles.
  • the ligands are generally organophosphorus compounds, such as phosphites, phosphinites, phosphonites or phosphines. They can be monodentate or polydentate. In the case of processes in a two-phase medium, these organophosphorus ligands advantageously comprise one or more ionizable groups, such as sulphonate, phosphonate, carboxylate or ammonium groups, for example, to render them soluble in the polar phase.
  • organophosphorus ligands advantageously comprise one or more ionizable groups, such as sulphonate, phosphonate, carboxylate or ammonium groups, for example, to render them soluble in the polar phase.
  • French Patent No. 2 338 253 it also discloses a process for the synthesis of adiponitrile by hydrocyanation of butadiene.
  • the reaction is carried out in a two-phase liquid medium, the catalyst being present in an aqueous phase.
  • This process makes it possible to recover the adiponitrile, devoid of catalyst and therefore of metal, in the organic phase.
  • the catalyst disclosed is also a catalyst based on a metal, such as nickel, in combination with a ligand of the phosphine type.
  • this ligand comprises sulphonate radicals, making it possible to render the catalyst soluble or dispersible in water.
  • nickel-based catalyst with promoters, such as Lewis acids, such as, for example, zinc chloride or triphenylborane, for the hydrocyanation of an unsaturated nitrile compound.
  • promoters such as Lewis acids, such as, for example, zinc chloride or triphenylborane
  • One of the aims of the present invention is to provide a novel process for the manufacture of nitrites by hydrocyanation of an olefin by reaction with hydrogen cyanide which makes it possible to obtain high yields of and high selectivities for linear nitrites and an improved stability of the catalytic system.
  • 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.
  • the latter compound will be referred to, for greater simplicity, in the present invention as an olefin or polyolefin, when it comprises several ethylenic unsaturations.
  • organic compounds suitable for the invention should not be interpreted as limiting the organic compounds suitable for the invention to hydrocarbons but it also relates to organic compounds comprising at least one ethylenic unsaturation and which can comprise atoms other than carbon and hydrogen or mixtures of hydrocarbons, such as the mixture obtained by distillation of oil known in the hydrocarbons field as the C 4 cut.
  • This cut is advantageously treated to remove or convert impurities, such as compounds comprising an acetylenic unsaturation, for example by hydrogenation, as disclosed in U.S. Pat. No. 6,197,992.
  • a compound will be regarded as an “olefin” within the meaning of the present invention which comprises an unsaturation and a nitrile functional group, such as, for example, the unsaturated nitrile compounds obtained by the reaction of HCN with a polyolefin.
  • the 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 which is in the liquid state at least at the temperature at which the hydrocyanation reaction is carried out.
  • 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 which is in the liquid state at least at the temperature at which the hydrocyanation reaction is carried out.
  • the ionic liquid and the compound to be hydrocyanated are completely miscible, at least at the reaction temperature.
  • the hydrocyanation reaction is carried out in a homogeneous or single-phase medium.
  • the ionic liquid and the compound to be hydrocyanated are immiscible or are only partially miscible at the reaction temperature.
  • the reaction is carried out in a nonhomogeneous or two-phase medium.
  • the catalytic system is advantageously soluble in the ionic liquid.
  • a solvent of low polarity can be added from the beginning of the reaction but can also be used only after the end of the reaction, in order thus to promote the separation of the hydrocyanated products and of the ionic liquid, in particular in order to make possible the extraction of the catalytic system. This is because the solvent of low polarity has the role of rendering the ionic liquid insoluble in the phase composed of the said solvent, the unconverted olefin and the nitrile compounds formed.
  • the catalytic system it is preferable for the catalytic system to be at least partially miscible in the ionic liquid.
  • this miscibility can be obtained by the presence of at least one ionizable group in the molecule of the organophosphorus ligand.
  • ionizable groups of groups of anionic type, such as sulphonate, phosphonate, phosphinate, carboxylate or sulphinate, or of cationic type, such as guanidinium, ammonium, pyridinium, imidazolium, phosphonium or sulphonium, for example.
  • the number and the nature of these ionic groups are preferably chosen in order to render the ligand soluble in the ionic liquid. It can be advantageous for the nature of the ionizable group to be identical to that of the anion or of the cation associated with the ionic liquid.
  • the catalytic systems suitable for the invention are those which preferably comprise the element nickel in the zero oxidation state or a complex with organophosphorus ligands which can comprise several ionizable groups described above or more generally compounds comprising phosphorus capable of giving a coordination compound with transition metals and more particularly the abovementioned catalytic metals, in particular with nickel.
  • organophosphorus ligands which can comprise several ionizable groups described above or more generally compounds comprising phosphorus capable of giving a coordination compound with transition metals and more particularly the abovementioned catalytic metals, in particular with nickel.
  • These compounds can be mono-, bi- or polydentate and can exhibit a hydrophobic or hydrophilic nature.
  • These compounds have been disclosed in numerous patents relating to the hydrocyanation of butadiene and belong to several classes, including in particular the organophosphites, organophosphonites, organophosphinites and organophosphines.
  • organic phosphorus compounds which are suitable for the invention, of alkylphosphines, arylphosphines, alkylarylphosphines, alkyl phosphites, aryl phosphites, alkylaryl phosphites, alkylphosphinites, arylphosphinites, alkylarylphosphinites, alkylphosphonites, arylphosphonites or alkylarylphosphonites, the organic moiety of which comprises up to 36 carbon atoms and which are preferably substituted by one or more ionic groups described above.
  • tributylphosphine dimethyl(n-octyl)phosphine, tricyclohexylphosphine, triphenylphosphine, tolylphosphine, tris(p-methoxyphenyl)phosphine, diphenylethylphosphine, dimethylphenylphosphine, 1,4-bis(diphenylphosphino)butane, triethyl phosphite or diphenyl phosphite, the said compounds preferably comprising at least one ionic group described above.
  • TPPMSNa triphenylphosphine(mono meta sodium sulphate)
  • TPPMSNa triphenylphosphine(mono meta sodium sulphate)
  • 5-sodiocarboxyfur-2-yl 5-sodiocarboxyfur-2-yl
  • 3-sodiosulphinatophenyl diphenylphosphine
  • the catalyst can be prepared before its introduction into the medium or in situ.
  • the compounds of the metals forming the catalytic element such as nickel, which are added to a medium in which the organophosphorus ligand is also soluble.
  • a medium can be the ionic liquid.
  • the catalytic system thus formed is added to the hydrocyanation medium.
  • the preferred compounds among the abovementioned compounds are those of nickel. Mention may be made, as nonlimiting examples, of:
  • the compounds in which the nickel is in the zero oxidation state such as potassium tetracyanonickelate K 4 [Ni(CN) 4 ], bis(acrylonitrile)nickel(0), bis(1,5-cyclooctadiene)nickel and derivatives comprising ligands from Group Va, such as tetrakis(triphenylphosphine)nickel(0);
  • the nickel compounds in which the nickel is in an oxidation state greater than zero such as the carboxylates (in particular the acetate), carbonate, bicarbonate, borate, bromide, chloride, citrate, thiocyanate, cyanide, formate, hydroxide, hydrophosphite, phosphite, phosphate and derivatives, iodide, nitrate, sulphate, sulphite, aryl- and alkylsulphonates, allyl or acetylacetonate.
  • carboxylates in particular the acetate
  • carbonate bicarbonate
  • borate bromide
  • chloride citrate
  • thiocyanate cyanide
  • formate hydroxide
  • hydrophosphite phosphite
  • phosphate and derivatives iodide
  • nitrate sulphate
  • sulphite sulphite
  • aryl- and alkylsulphonates allyl or
  • the nickel compound it is not necessary for the nickel compound to be itself soluble in the preparation medium, such as the ionic liquid. This is because it is sufficient for the complex to be soluble, that is to say for the dissolution of the nickel to take place during the addition of the ligand to the ionic liquid.
  • a reducing agent for nickel which preferably reacts with the latter under the reaction conditions is added to the reaction medium.
  • This reducing agent can be organic or inorganic or hydrogen. Mention may be made, as nonlimiting examples, of Zn powder, magnesium, KBH 4 , NaBH 4 and borohydrides preferably soluble in water.
  • This reducing agent is added in an amount such that the number of oxidation/reduction equivalents is between 1 and 10. However, values of less than 1 and greater than 10 are not excluded.
  • the nickel compound used corresponds to the 0 oxidation state of nickel
  • a reducing agent of the type of those mentioned above can also be added but this addition is not essential.
  • the reducing agents can, in addition, be components of the reaction medium (phosphine, solvent, olefin).
  • the reaction medium comprises an ionic liquid.
  • This ionic liquid is an ionic compound, the cation of which is of onium type having at least one heteroatom, such as N, P or S, carrying the positive charge in conjunction with a 5- or 6-membered aromatic ring, and an anion.
  • the ionic liquid comprises at least one cation chosen from the group consisting of the structures tetraalkylammonium, N-alkylimidazolium, N-alkylpyridinium, N-alkylpicolinium, N-alkyltriazolium, N-alkylfluoropyrazolium, N-pyrrolidinium, alkylsulphonium, tetraalkylphosphonium and alkyloxonium.
  • alkylimidazoliums such as 1,3-dimethylimidazolium, 1-butyl-2,3-dimethylimidazolium, 1-butyl-3-methylimidazolium or 1,2,3-trimethylimidazolium.
  • an anion chosen from halides, nitrate, phosphate, hydrosulphate, perfluoroalkylsulphonates, bis(perfluoroalkylsulphonyl)amides, bis(fluorosulphonyl)amide, bis(fluorophosphoryl)amide, tris(perfluoroalkylsulphonyl)me
  • the preferred anions of the invention are Br ⁇ , I ⁇ , BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , AlCl 4 ⁇ , ZnCl 3 ⁇ , SnCl 3 ⁇ and (CF 3 SO 2 ) 2 N ⁇ .
  • the ionic liquid to be suitable for the process of the invention, must be in the liquid state at least at the temperature at which the hydrocyanation reaction is carried out.
  • ionic liquids which are found in the liquid state at a temperature of less than 100° C. are preferred as they make possible better separation and extraction of the catalyst from the reaction medium in the case of a two-phase system.
  • the ionic liquid which becomes miscible or at least partially miscible in the reaction medium only at the temperature at which the hydrocyanation reaction is carried out, or in the vicinity of the latter, is entirely compatible for the implementation of the invention.
  • the immiscibility of the ionic liquid is preferably obtained by addition to the reaction medium of a solvent of low polarity.
  • This solvent dissolves the olefins to be hydrocyanated and the nitrites produced and renders the ionic liquid insoluble in the olefins and nitrites produced.
  • Mention may be made, as solvent of low polarity, of saturated hydrocarbons, such as hexane, heptane, octane or toluene, or ethers, such as diethyl ether, diisopropyl ether or methyl isobutyl ether.
  • the amount of nickel compound or compound of another transition metal used is chosen in order to obtain a concentration as moles of transition metal per mole of organic compounds to be hydrocyanated or isomerized of between 10 ⁇ 4 and 1 and preferably between 0.005 and 0.5 mol of nickel or of the other transition metal employed.
  • the amount of ligand used to form the catalyst is chosen so that the number of moles of this compound with respect to 1 mol of transition metal is between 0.5 and 50 and preferably between 2 and 10.
  • the hydrocyanation reaction is generally carried out at a temperature of between 10° C. and 200° C. and preferably between 30° C. and 120° C.
  • the process of the invention can be carried out continuously or batchwise.
  • the hydrogen cyanide employed can be prepared from metal cyanides, in particular sodium cyanide, or cyanohydrins, such as acetone cyanohydrin, or by any other known synthetic process.
  • the hydrogen cyanide is introduced into the reactor in the gaseous form or in the liquid form. It can also be dissolved beforehand in an organic solvent.
  • reaction mixture is withdrawn after cooling and the reaction products are isolated, for example by separation of the phase comprising the catalytic system and of the phase formed by the solvent of low or no polarity, the hydrocyanated products and those which have not been converted, in the case of a two-phase system.
  • the products from the latter phase can be separated, for example by distillation.
  • other separation means can be employed, such as, for example, distillation or liquid/liquid extraction.
  • the product to be hydrocyanated is an unsaturated compound comprising a nitrile functional group
  • a cocatalyst comprising at least one Lewis acid
  • This reaction consists in particular in converting aliphatic nitrites comprising ethylenic unsaturation, in particular linear pentenenitriles, such as 3-pentenenitrile, 4-pentenenitrile and their mixtures, obtained by hydrocyanation of butadiene, to dinitriles, more specifically to adiponitrile.
  • linear pentenenitriles such as 3-pentenenitrile, 4-pentenenitrile and their mixtures, obtained by hydrocyanation of butadiene, to dinitriles, more specifically to adiponitrile.
  • pentenenitriles can comprise amounts, generally minor amounts, of other compounds, such as 2-methyl-3-butenenitrile, 2-methyl-2-butenenitrile, 2-pentenenitrile, valeronitrile, adiponitrile, 2-methylglutaronitrile, 2-ethylsuccinonitrile or butadiene, originating from the prior reaction for the hydrocyanation of butadiene and/or from the isomerization of 2-methyl-3-butenenitrile to pentenenitriles.
  • other compounds such as 2-methyl-3-butenenitrile, 2-methyl-2-butenenitrile, 2-pentenenitrile, valeronitrile, adiponitrile, 2-methylglutaronitrile, 2-ethylsuccinonitrile or butadiene, originating from the prior reaction for the hydrocyanation of butadiene and/or from the isomerization of 2-methyl-3-butenenitrile to pentenenitriles.
  • the Lewis acid used as cocatalyst makes it possible in particular, in the case of the hydrocyanation of aliphatic nitrites comprising ethylenic unsaturation, to improve the linearity of the dinitriles obtained, that is to say the percentage of linear dinitriles with respect to all the dinitriles formed, and/or to increase the activity and the lifetime of the catalyst.
  • Lewis acid is understood to mean, in the present text, according to the usual definition, compounds which accept electron pairs.
  • Lewis acids which can be employed as cocatalysts in the present process are chosen from the compounds of the elements from Groups Ib, IIb, IIIa, IIIb, IVa, IVb, Va, Vb, VIIb, VIIb and VIII of the Periodic Table.
  • These compounds are generally salts, in particular halides, such as chlorides or bromides, sulphates, sulphonates, halosulphonates, perhaloalkylsulphonates, in particular fluoroalkylsulphonates or perfluoroalkylsulphonates, carboxylates, phosphates, bis(perfluoroalkylsulphonyl)amides and tris(perfluoroalkylsulphonyl)methides.
  • halides such as chlorides or bromides
  • sulphates sulphonates, halosulphonates
  • perhaloalkylsulphonates in particular fluoroalkylsulphonates or perfluoroalkylsulphonates, carboxylates, phosphates, bis(perfluoroalkylsulphonyl)amides and tris(perfluoroalkylsulphonyl)methides.
  • Lewis acids of zinc chloride, zinc bromide, zinc iodide, manganese chloride, manganese bromide, cadmium chloride, cadmium bromide, stannous chloride, stannous bromide, stannous sulphate, stannous tartrate, indium trifluoromethylsulphonate, the chlorides or bromides of rare-earth metal elements, such as lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, hafnium, erbium, thallium, ytterbium and lutetium, cobalt chloride, ferrous chloride or yttrium chloride.
  • rare-earth metal elements such as lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, ha
  • Lewis acid Use may also be made, as Lewis acid, of organometallic compounds, such as triphenylborane or titanium diisopropoxide. It is, of course, possible to employ mixtures of several Lewis acids.
  • the choice will preferably be made of a Lewis acid having an anion identical to or of the same nature as the anion of the ionic liquid, such as, for example, zinc chloride when the ionic liquid comprises ZnCl 3 ⁇ as anion, aluminium chloride when the anion of the ionic liquid is the anion AlCl 4 ⁇ , lanthanum tris(bistrifluoromethylsulphonylamide) when the ionic medium is composed of the bistrifluoromethylsulphonylamide anion, or neodymium tris(trifluoromethylsulphonate) when the anion of the ionic medium is the trifluoromethysulphonate anion.
  • a Lewis acid having an anion identical to or of the same nature as the anion of the ionic liquid such as, for example, zinc chloride when the ionic liquid comprises ZnCl 3 ⁇ as anion, aluminium chloride when the anion of the ionic liquid is the anion AlCl 4
  • an ionic liquid composed of a mixture of polynuclear anions, such as the anion Zn 2 Cl 5 ⁇ and of ZnCl 3 ⁇ , or Al 2 Cl 7 ⁇ 0 and of AlCl 4 ⁇ .
  • the Lewis acid will be contributed by the anion of the ionic liquid.
  • This ionic liquid itself contributes the effect of cocatalyst to the medium.
  • the Lewis acid cocatalyst employed generally represents from 0.01 to 50 mol per mole of transition metal compound, more particularly of nickel compound, and preferably from 1 to 10 mol per mole.
  • the 2-methyl-3-butenenitrile subjected to isomerization according to the invention can be employed alone or as a mixture with other compounds.
  • 2-methyl-3-butenenitrile can be used as a mixture with 2-methyl-2-butenenitrile, 4-pentenenitrile, 3-pentenenitrile, 2-pentenenitrile, butadiene, adiponitrile, 2-methylglutaronitrile, 2-ethylsuccinonitrile or valeronitrile.
  • the isomerization reaction is generally carried out at a temperature of 10° C. to 200° C. and preferably of 60° C. to 120° C.
  • the catalytic system used for the isomerization can be prepared before its introduction into the reaction region. It is also possible to prepare the catalytic system “in situ” by simple mixing of these various constituents. The amount of transition metal compound and more particularly of nickel compound used and the amount of ligand are the same as for the hydrocyanation reaction.
  • the preparation of dinitrile compounds by hydrocyanation of an olefin such as butadiene can be carried out using a reaction system in accordance with the invention for the stages of formation of the unsaturated nitrites and the stage of isomerization above, it being possible for the reaction for the hydrocyanation of the unsaturated nitrites to dinitriles to be carried out with a reaction system in accordance with the invention or any other catalytic system already known for this reaction.
  • reaction for the hydrocyanation of the olefin to unsaturated nitrites and the isomerization of the latter can be carried out with a reaction system different from that of the invention, the stage of hydrocyanation of the unsaturated nitrites to dinitriles being carried out with a reaction system in accordance with the invention.
  • TY (X) true yield of the compound X, corresponding to the ratio of the number of moles of X formed to the maximum number of moles of X
  • TPPMSNa sodium triphenylphosphate
  • the tube is closed, then stirred and heated at 100° C. for 3 hours with head cooling. At the end of the reaction, the tubes are cooled in liquid nitrogen. A known amount of butylbenzene (approximately 40 mg, to act as chromatography internal standard) is added to the two-phase reaction medium, which is diluted and homogenized by the addition of 10 ml of THF. The solution obtained is filtered through a short silica column and injected in gas chromatography (GC).
  • GC gas chromatography
  • the starting materials comprise 2M3BN and other products.
  • the molar formulation of these products is given in Table I below (the main components are shown).
  • TABLE I Component Abbreviation Mol % 2-Methyl-3-butenenitrile 2M3BN 79 2-Methyl-2-butenenitrile 2M2BN 12.70 2-Pentenenitrile 2PN 6.30 4-Pentenenitrile 4PN 0 3-Pentenenitrile 3PN 1.30

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Publication number Priority date Publication date Assignee Title
US20090247780A1 (en) * 2001-09-18 2009-10-01 Rhodia Polyamide Intermediates Method of producing nitrile compounds
US7880028B2 (en) 2006-07-14 2011-02-01 Invista North America S.A R.L. Process for making 3-pentenenitrile by hydrocyanation of butadiene
US7897801B2 (en) 2003-05-12 2011-03-01 Invista North America S.A R.L. Process for the preparation of dinitriles
US7919646B2 (en) 2006-07-14 2011-04-05 Invista North America S.A R.L. Hydrocyanation of 2-pentenenitrile
US7973174B2 (en) 2005-10-18 2011-07-05 Invista North America S.A.R.L. Process of making 3-aminopentanenitrile
US7977502B2 (en) 2008-01-15 2011-07-12 Invista North America S.A R.L. Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile
US8088943B2 (en) 2008-01-15 2012-01-03 Invista North America S.A R.L. Hydrocyanation of pentenenitriles
US8101790B2 (en) 2007-06-13 2012-01-24 Invista North America S.A.R.L. Process for improving adiponitrile quality
US8178711B2 (en) 2006-03-17 2012-05-15 Invista North America S.A R.L. Method for the purification of triorganophosphites by treatment with a basic additive
US8247621B2 (en) 2008-10-14 2012-08-21 Invista North America S.A.R.L. Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols
US8338636B2 (en) 2009-08-07 2012-12-25 Invista North America S.A R.L. Hydrogenation and esterification to form diesters
US8373001B2 (en) 2003-02-10 2013-02-12 Invista North America S.A R.L. Method of producing dinitrile compounds
US8906334B2 (en) 2007-05-14 2014-12-09 Invista North America S.A R.L. High efficiency reactor and process

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WO2005014547A1 (en) * 2003-07-17 2005-02-17 Novartis Ag Mixtures of ionic liquids with lewis acids
FR2926549B1 (fr) * 2008-01-18 2015-05-01 Rhodia Operations Procede de fabrication de composes nitriles
FR2928910B1 (fr) * 2008-03-20 2010-03-12 Arkema France Procede ameliore de production d'acide cyanhydrique
FR2932476B1 (fr) * 2008-06-17 2010-07-30 Rhodia Operations Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
CN102786449A (zh) * 2008-12-05 2012-11-21 华中科技大学 一种由全氟烷基磺酰亚胺碱金属盐合成的离子液体
US11267707B2 (en) 2019-04-16 2022-03-08 Honeywell International Inc Purification of bis(fluorosulfonyl) imide
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6197992B1 (en) * 1996-12-16 2001-03-06 Basf Aktiengesellschaft Monoolefinic C5 mononitriles, method for the production and the use thereof
US6559344B2 (en) * 2001-02-19 2003-05-06 Basf Aktiengesellschaft Hydroformylation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2338253A1 (fr) * 1976-01-13 1977-08-12 Rhone Poulenc Ind Procede d'hydrocyanation de composes organiques insatures comportant au moins une double liaison ethylenique
FR2711987B1 (fr) * 1993-11-03 1995-12-15 Rhone Poulenc Chimie Procédé d'hydrocyanation de nitriles insaturés en dinitriles.
FR2739378B1 (fr) * 1995-09-29 1997-10-31 Rhone Poulenc Fibres Procede d'hydrocyanation de composes organiques a insaturation ethylenique
AU2165000A (en) * 1998-12-04 2000-06-19 Symyx Technologies, Inc. Combinatorial discovery and testing of ionic liquids
FR2787446B1 (fr) * 1998-12-22 2001-02-02 Rhone Poulenc Fibres Procede d'hydrocyanation de composes organiques a insaturations ethyleniques
FR2829763B1 (fr) 2001-09-18 2004-12-03 Rhodia Polyamide Intermediates Procede de fabrication de composes nitriles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6197992B1 (en) * 1996-12-16 2001-03-06 Basf Aktiengesellschaft Monoolefinic C5 mononitriles, method for the production and the use thereof
US6559344B2 (en) * 2001-02-19 2003-05-06 Basf Aktiengesellschaft Hydroformylation

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8039660B2 (en) 2001-09-18 2011-10-18 Rhodia Polyamide Intermediates Method of producing nitrile compounds
US20090247780A1 (en) * 2001-09-18 2009-10-01 Rhodia Polyamide Intermediates Method of producing nitrile compounds
US8373001B2 (en) 2003-02-10 2013-02-12 Invista North America S.A R.L. Method of producing dinitrile compounds
US7897801B2 (en) 2003-05-12 2011-03-01 Invista North America S.A R.L. Process for the preparation of dinitriles
US7973174B2 (en) 2005-10-18 2011-07-05 Invista North America S.A.R.L. Process of making 3-aminopentanenitrile
US8178711B2 (en) 2006-03-17 2012-05-15 Invista North America S.A R.L. Method for the purification of triorganophosphites by treatment with a basic additive
US7919646B2 (en) 2006-07-14 2011-04-05 Invista North America S.A R.L. Hydrocyanation of 2-pentenenitrile
US7880028B2 (en) 2006-07-14 2011-02-01 Invista North America S.A R.L. Process for making 3-pentenenitrile by hydrocyanation of butadiene
US8394981B2 (en) 2006-07-14 2013-03-12 Invista North America S.A R.L. Hydrocyanation of 2-pentenenitrile
US8906334B2 (en) 2007-05-14 2014-12-09 Invista North America S.A R.L. High efficiency reactor and process
US8101790B2 (en) 2007-06-13 2012-01-24 Invista North America S.A.R.L. Process for improving adiponitrile quality
US7977502B2 (en) 2008-01-15 2011-07-12 Invista North America S.A R.L. Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile
US8088943B2 (en) 2008-01-15 2012-01-03 Invista North America S.A R.L. Hydrocyanation of pentenenitriles
US8247621B2 (en) 2008-10-14 2012-08-21 Invista North America S.A.R.L. Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols
US8338636B2 (en) 2009-08-07 2012-12-25 Invista North America S.A R.L. Hydrogenation and esterification to form diesters

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US20090247780A1 (en) 2009-10-01
EP1427695A1 (fr) 2004-06-16
CN100455562C (zh) 2009-01-28
FR2829763B1 (fr) 2004-12-03
JP2005503410A (ja) 2005-02-03
US8039660B2 (en) 2011-10-18
RU2004111655A (ru) 2005-04-10
KR20040068537A (ko) 2004-07-31
FR2829763A1 (fr) 2003-03-21
CN1564807A (zh) 2005-01-12
WO2003024919A1 (fr) 2003-03-27
JP4166155B2 (ja) 2008-10-15
RU2265591C2 (ru) 2005-12-10

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