Distillation Control for Solvent-Nickel Catalyst Separation

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Solution Overview

Problem

The existing processes for producing adiponitrile (ADN) face challenges in efficiently separating catalysts containing nickel and bidentate phosphorus-containing ligands, particularly due to isomerization of 3-pentenenitrile to 2-methyl-3-butenenitrile in distillation column bottoms, which leads to yield loss and catalyst inefficiency.

Innovation Solution

A method is introduced to control the ratio of 2-pentenenitrile to 3-pentenenitrile in the distillation zone, where the catalyst solution comprising nickel and a bidentate phosphorus-containing ligand is subjected to distillation conditions to form a solvent-depleted catalyst solution, with a targeted ratio of 3-pentenenitrile to 2-pentenenitrile of 14 or less, thereby reducing unwanted isomerization and enhancing catalyst concentration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of substance

If distillation is used to separate solvent from catalyst, then solvent removal is achieved, but isomerization of 3-pentenenitrile to 2-methyl-3-butenenitrile occurs causing yield loss

Engineering Contradiction:
Improveadiponitrile yieldVSAvoidseparation process
Core Design Contradiction:
Loss of substanceVSEase of manufacture

Solution Approach 1:

The patent changes the chemical composition parameters of the distillation system by adding 2-pentenenitrile as an intermediate boiler and adjusting the nickel catalyst to bidentate phosphorus ligand complex. This modifies the distillation behavior to reduce isomerization while maintaining separation efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

2-pentenenitrile is introduced as an intermediate boiler that mediates the distillation process. It has a boiling point between the solvent and catalyst components, allowing it to act as a buffer that reduces thermal stress on 3-pentenenitrile and minimizes isomerization to 2-methyl-3-butenenitrile

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If high temperature distillation is used to remove solvent, then separation efficiency increases, but catalyst degradation and isomerization increase

Engineering Contradiction:
Improveseparation rateVSAvoidcatalyst efficiency
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent changes the boiling point parameters of the system by introducing 2-pentenenitrile with intermediate volatility. This creates a stepped distillation profile that allows solvent removal at lower temperatures, preventing catalyst degradation and isomerization while maintaining separation productivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses 2-pentenenitrile as a substitute intermediate that copies the functional role of traditional intermediate boilers but with optimized properties for reducing isomerization. It serves as a proxy substance that protects the main catalyst system from thermal stress

Inventive Principle:
Principle #26Copying

3Quantity of substance

If conventional distillation conditions are used, then solvent removal is achieved, but 3-pentenenitrile isomerizes to 2-methyl-3-butenenitrile

Engineering Contradiction:
Improvesolvent removalVSAvoidpentenenitrile isomer composition
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

2-pentenenitrile acts as an intermediary substance that stabilizes the composition during distillation. Its presence creates a buffer zone in the distillation column that prevents direct thermal contact between 3-pentenenitrile and high-temperature zones, maintaining compositional stability

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent modifies the compositional parameters by adding 2-pentenenitrile and adjusting the nickel to bidentate phosphorus ligand complex ratio. These parameter changes shift the distillation equilibrium to favor solvent removal while suppressing isomerization reactions

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach effectively minimizes the isomerization of 3-pentenenitrile to 2-methyl-3-butenenitrile, thereby increasing adiponitrile yield and maintaining catalyst efficiency by concentrating the catalyst solution while optimizing distillation conditions.

Implementation Method 1

A method is introduced to control the ratio of 2-pentenenitrile to 3-pentenenitrile in the distillation zone, where the catalyst solution comprising nickel and a bidentate phosphorus-containing ligand is subjected to distillation conditions to form a solvent-depleted catalyst solution

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

the catalyst solution comprising nickel and a bidentate phosphorus-containing ligand is subjected to distillation conditions to form a solvent-depleted catalyst solution

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentUS10759741B2Separating a solvent from a nickel catalyst by distillation
Publication Date: 2020.09.01 INV NYLON CHEMICALS AMERICAS LLC
  • US10759741B2 patent drawing
  • US10759741B2 patent drawing
  • US10759741B2 patent drawing

AI summary

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.