Invista North America S.a.r.l.

Inv Nylon Chemicals Americas, LLC

Invista Technologies S.a.r.l.

Invista Textiles Limited

William J Tenn, Iii

Thomas E Vos

Sudhir N V K Aki

Tseng H Chao

Sudhir Aki

James Michael Garner

Gregory S Kirby

Larry E Moerbe

Bruce Edwin Murphree

Benjamin D Herzog

Milind V Kantak

James E McIntosh

Michael W Wensing

Wyatte E Allen

Mark Anstrom

Charles Nelson Campbell, Ii

Sudkir N V K Aki

Mark D Rogers

Sudhir NVK Aki

Disclosed is a process for preparing adiponitrile from acrylonitrile in an electrolytic cell. An aqueous electrolyte comprising acrylonitrile converts to adiponitrile in the presence of a solid anode and in the absence of a solid cathode. The cathode comprises gas plasma.

Production of adiponitrile

A solvent is at least partially separated from a catalyst. The catalyst comprises nickel and a bidentate phosphorus-containing ligand. The method for separation involves distilling a catalyst solution. The ratio of 2-pentenenitrile to 3-pentenenitrile in distillation column bottoms is controlled to reduce the amount of 3-pentenenitrile which is isomerized to form 2-methyl-3-butenenitrile. Isomerization of 3-pentenenitrile to 2-methyl-3-butenenitrile and subsequent isomerization of 2-methyl-3-butenenitrile to 2-methyl-2-butenenitrile, and/or hydrocyanation of 2-methyl-3-butenenitrile to methylglutaronitrile represents a loss in adiponitrile yield in a process for making adiponitrile.

Separating a solvent from a nickel catalyst by distillation

Disclosed is a method for inhibiting the formation of by-products from dinitriles, such as the formation of cyclopentylideneimine (CPI) from Adiponitrile (ADN), comprising adding an effective amount of a Br&#xf8;nsted acid to the ADN. Also disclosed is a method of refining a dinitrile compound by distillation the method comprising the steps of: (a) supplying (i) a feedstream comprising the dinitrile compound and (ii) a Br&#xf8;nsted acid to a distillation apparatus; and (b) withdrawing from the distillation apparatus an overhead distillate stream comprising the dinitrile compound.

Inhibiting CPI formation from adiponitrile

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 least one byproduct including bis-hexamethylene triamine (BHMT) or 1,2-diaminocyclohexane. At least a portion of the HMD product or byproduct is used to enhance the liquid-liquid extraction to recover phosphorus-containing ligand.

Integrated process for nitrile manufacture with enhanced liquid-liquid extraction

Disclosed herein are methods for recovering phosphorus-containing ligand from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the phosphorus-containing ligand.

Enhanced extraction of impurities from mixture comprising nitriles

The present invention relates to an improved process for addition of hydrogen cyanide across olefins and, in particular, to the use of a specific aluminum oxide to catalyze the reaction. The aluminum oxide catalyst must have total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 3,000 ppm by weight.

Heterogeneous hydrocyanation

A process of stabilizing a bidentate or tridentate phosphorus-based phosphite ester ligand or mixture thereof in a hydrocyanation reaction milieu comprising water, wherein the ligand or ligand mixture comprises one or more of (i) a bidentate biphosphite ligand of formula (III), (R&#x2014;X) (R&#x2014;X) P&#x2014;X&#x2014;Y&#x2014;X&#x2014;P(X&#x2014;R) (X&#x2014;R) or (ii) a tridentate triphosphite ligand of formula (IIIA) (R&#x2014;X) (R&#x2014;X) P&#x2014;X&#x2014;Y&#x2014;X&#x2014;P(X&#x2014;R)&#x2014;(X&#x2014;Y&#x2014;R&#x2014;P(X&#x2014;R)&#x2014;(X&#x2014;R) where each X is oxygen or a bond and each Y is an optionally substituted C6-C20 arylene group, comprising admixing the bidentate and/or tridentate with a stabilizing amount of one or more monodentate phosphite ligand of formula P(X&#x2014;R)(X&#x2014;R)(X&#x2014;R) where each X is oxygen or a bond, wherein the monodentate ligand has a rate of hydrolysis greater than the rate of hydrolysis of the bidentate or tridentate ligand in the presence of water in a hydrocyanation reaction milieu, and thereby preserve concentrations and proportions of the bidentate and/or tridentate ligand(s) in the ligand blend.

Stable ligand mixtures and processes for making same

Disclosed herein are methods for recovering diphosphonite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using multistage countercurrent liquid-liquid extraction. Recovery is enhanced with one or more method steps. In a first step, a portion of the heavy phase from the settling section of the first stage is recycled to the settling section of the first stage. In a second step, a portion of the light phase from the settling section of the first stage is recycled to the mixing section of the first stage. In a third step, the first stage takes place in a mixer-settler, a Lewis base is introduced into the settling section of the first stage, and a complex of Lewis acid and Lewis base is formed in this settling section. In a fourth step, a polyamine is added to the first stage.

Extraction solvent control for reducing stable emulsions

Pentenenitrile oligomers formed in a process for isomerizing cis-2-pentenenitrile to 3-pentenenitrile are minimized in the presence of an aluminum oxide catalyst. The process comprises providing an aluminum oxide catalyst having an alkali metal and/or alkaline earth metal and/or iron content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide and/or iron oxide, respectively of less than 5000 ppm by weight.

Pentenenitrile isomerization

Disclosed is a process for isomerizing cis-2-pentenenitrile to 3-pentenenitrile in the presence of a non-aluminum metal oxide catalyst, wherein: (a) the metal in the catalyst has an oxidation state in the range from +1 to +4; (b) the metal has a cation radius in the range from 0.35 to 1.0 &#x212b;; (c) the metal of the catalyst has a polarizing power, C/r, is in the range from 2 to &#x3e;8, wherein C is the charge of the metal and r is the ionic radius in &#x212b;; (d) the bond network of the catalyst has a % ionicity of &#x3e;20; (e) the metal oxide has an acidity strength in the range from strong to very weak; and (f) the metal oxide has a basicity (nucleophilicity) strength of weak to strong.

Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the diphosphite-containing compounds.

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.

Process for stabilizing hydrocyanation catalyst

Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are pre-treatments to enhance extractability of the diphosphite-containing compounds.

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.

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Beaumont, TX, United States of America

William J Tenn, Iii