Abstract:
Phosphorus-containing ligands are recovered from mixtures comprising 3-pentenenitrile (3PN) and adiponitrile (ADN), using liquid-liquid extraction. ADN is produced by hydrocyanation of 3PN. The ADN is hydrogenated to produce a hexamethyiene diamine (HMD) and at Ieast one byproduct including bis-hexamethylene triamine (BHMT) or 1,2-diaminocyclohexane. At Ieast a portion of the HMD product or byproduct is used to enhance the liquid-liquid extraction to recover phosphorus-containing ligand.
Abstract:
The invention provides a method of forming a phosphonate diester compound from a ligand hydrolysis product (LHP) of a phosphite ligand used in a nickel-phosphite hydrocyanation catalyst, such as for conversion of 3-pentenenitrile to adiponitrile, which serves to eliminate acidic LHP compound for a hydrocyanation reaction milieu where the acidic LHP can catalyze further catalyst ligand destruction. The invention further provides phosphonate disester compounds prepared by alkylation of diarylphosphite LHP in the presence of a nickel-phosphite catalyst comprising a bidentate ligand, and a continuous hydrocyanation process for production of adiponitrile wherein catalyst ligand breakdown is inhibited through inactivation of ligand hydrolysis products towards further breakdown. A method of stabilizing a hydrocyanation catalyst is provided.
Abstract:
Die vorliegende Erfindung bezieht sich auf die Herstellung von 3-Cyano-3,5,5- trimethylcyclohexanon (Isophoronnitril, kurz IPN) unter Verwendung eines Calciumalkoholates, im besonderen Calciumethanolat, als Katalysator.
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 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, which separates catalyst degradation products and reaction byproducts, such as mononitriles having 9 carbon atoms, from the catalyst.
Abstract:
La présente invention concerne un procédé de fabrication de composés hydrocarbonés comprenant au moins une fonction nitrile. Elle concerne plus particulièrement un procédé de fabrication de composés nitriles par hydrocyanation de composés comprenant au moins une insaturation éthylénique. Selon l'invention, ce procédé comprend une étape de traitement par hydrodésazotation des sous-produits non valorisables comprenant au moins une fonction nitrile tels que le méthylglutaronitrile pour les transformer en ammoniac et composés hydrocarbonés valorisables.
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.
Abstract:
The invention provides a hydrocyanation process for the production of adiponitrile and other dinitriles having six carbon atoms, the process comprising: a) forming a reaction mixture in the presence of at least one Lewis acid, said reaction mixture comprising ethylenically unsaturated nitrites having five carbon atoms, hydrogen cyanide, and a catalyst precursor composition, by continuously feeding ethylenically unsaturated nitrites, hydrogen cyanide, and a catalyst precursor composition; b) controlling X and Z, wherein X is the overall feed molar ratio of 2-pentenenitriles to all unsaturated nitrites 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 0.99/1, such that the value of quotient Q, Formula (I), wherein Q is in the range from about 0.2 to about 10, wherein 3PN is 3- pentenenitriles and 4PN is 4-pentenenitrile; and c) withdrawing a reaction product mixture comprising adiponitrile; wherein the ratio of the concentration of 2-pentenenitriles to the concentration of 3-pentenenitriles in the reaction mixture is from about 0.2/1 to about 10/1; wherein the catalyst precursor composition comprises a zero-valent nickel and at least one multidentate phosphorus-containing ligand; wherein the multidentate phosphorus-containing ligand is 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 wherein the multidentate phosphorus-containing ligand gives acceptable results according to at least one protocol of the 2- Pentenenitrile Hydrocyanation Test Method.
Abstract:
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Adipodinitril enthaltenden Mischungen, das durch die vorliegenden Verfahrensschritte gekennzeichnet ist: a) Umsetzung von 3-Pentennitril mit Cyanwasserstoff in Gegenwart eines Hydrocya- nierungskatalysators, eines Promotors und eines Verdünnungsmittels unter Erhalt eines Hydrocyanierungsaustrages, der 3-Pentennitril, Adipodinitril, Methylglutardinitril, Ethylsuccinonitril, das Verdünnungsmittel, den Hydrocyanierungskatalysator, den Promotor und gegebenenfalls Abbauprodukte des Katalysators enthält; b) Destillation des Hydrocyanierungsaustrags aus Schritt a) unter Erhalt eines Stromes (1) als Kopfprodukt, der 3-Pentennitril enthält, und eines Stromes (2) als Sumpfprodukt, der Adipodinitril, Methylglutardinitril, Ethylsuccinonitril, den überwiegenden Teil des Verdünnungsmittels, des Hydrocyanierungskatalysators und des Promotors enthält; c) Extraktion des Stromes (2) mit einem Extraktionsmittel unter Erhalt eines Stromes (3), der den überwiegenden Teil des Verdünnungsmittels, des Hydrocyanierungskatalysators und des Extraktionsmittels enthält, und eines Stromes (4), der den überwiegenden Teil des Adipodinitrils, Methylglutardinitrils, Ethylsuccinonitrils und des Promotors enthält.
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.