Invista North America S.a.r.l.

Invista Technologies S.a.r.l.

Invista Textiles Limited

Thomas E Vos

William J Tenn, Iii

Sudhir N V K Aki

Tseng H Chao

Sudhir Aki

Joachim C Ritter

James Michael Garner

John Arthur Turner

Keith Whiston

Larry E Moerbe

Bruce Edwin Murphree

Stewart Forsyth

James E McIntosh

Mark D Rogers

Michael W Wensing

Charles Nelson Campbell, Ii

Mark Anstrom

Wyatte E Allen

William J Tenn Iii

Sudhir NVK Aki

William J Iii Tenn

Charles Nelson Ii Campbell

Wyatt E Allen

Mark A Anstrom

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

A process of hydrolyzing a monodentate, bidentate or tridentate phosphorus-based phosphite ester ligand or ligand blend for a transition metal catalyst comprising contacting the ligand or ligand blend with a hydrolysis catalyst of the formula (RX)P(OH)where n is 0, 1 or 2 wherein the ligand or ligand blend 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), (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;K&#x2014;P(X&#x2014;R)&#x2014;(X&#x2014;R) or (iii) a monodentate phosphite ligand of formula (IV) P(X&#x2014;R)(X&#x2014;R)(X&#x2014;R) where each X is oxygen or a bond and each Y is an optionally substituted C6-C20 arylene, followed by separation of the ligand hydrolysis products.

Hydrolysis catalyst and process

The invention provides methods useful in the industrial scale process for hydrocyanation of butadiene to adiponitrile for recycle of unwanted byproduct 2-methyl-3-butenenitrile (2M3BN) by conversion to process intermediate pentenenitrile. The invention provides a process for generating catalysts useful for carrying out the hydrocyanation of butadiene to adiponitrile, the process comprising contacting the 2M3BN and a solution of a nickel-ligand catalyst in cis-2-pentenenitrile (cis-2PN), trans-2-pentenenitrile (trans-2PN), or a mixture thereof. The improved methods of the invention can provide improved catalyst solubility for bidentate ligands without a requirement for a Lewis acid catalyst promoter such as zinc chloride to be present.

Process for producing pentenenitriles

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

In the hydrocyanation reaction of butadiene proceeding through pentenenitriles to adiponitrile, catalysis by complexes of zerovalent nickel with bidentate phosphorus-based ligands of the NiLA type wherein Lis 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.

Composition for improved nickel-ligand solubility

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.

Claimed is a process for producing a phosphorus-containing ligand, preferably a diphosphite ligand structure (DLS) such as structure I. The method includes contacting a phosphorochloridite (structure II) with a compound having the structure X&#x2014;OH (which can be a bisaryl compound), and a tertiary organic amine to provide structure I' and as preferred embodiment structure I. 

Method for making organodiphosphites from phosphorochloridites characterized by measuring side-product levels to determine further additions

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.

Process for making nitriles

Disclosed is a method for making a diphosphite of Structure I, 

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Beaumont, TX, United States of America

Thomas E Vos