Dinitrile Purification via Ion-Exchange Resin Extraction

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Solution Overview

Problem

Current processes for manufacturing dinitrile compounds, such as adiponitrile, involve the use of Lewis acids that can generate impurities and pose environmental and economic concerns due to their removal as effluents during distillation.

Innovation Solution

A process involving hydrocyanation with hydrogen cyanide in the presence of an organometallic complex and a cocatalyst, where the reaction medium is treated with an ion-exchange resin to extract the metal cocatalyst and organometallic complex, thereby separating dinitrile compounds without the need for Lewis acids during distillation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If Lewis acid is maintained in the reaction medium during distillation, then catalytic activity is preserved, but impurity generation increases and environmental harm occurs

Engineering Contradiction:
Improvecatalytic activityVSAvoidimpurity generation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and removes the Lewis acid from the reaction medium before distillation. The Lewis acid is separated from the dinitrile product through extraction techniques, allowing distillation to proceed without the harmful presence of Lewis acid while preserving catalytic activity through recovery and reuse of the extracted Lewis acid in subsequent batches.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent performs preliminary extraction of the Lewis acid from the reaction medium before the distillation step. This preliminary action removes the source of impurity generation and environmental harm before the distillation process begins, allowing clean separation of the dinitrile product while the Lewis acid is recovered for reuse.

Inventive Principle:
Principle #10Preliminary action

2Object-generated harmful factors

If Lewis acid is removed as effluent, then impurity generation is reduced, but process economics deteriorate and environmental harm increases

Engineering Contradiction:
Improveimpurity generationVSAvoidLewis acid loss
Core Design Contradiction:
Object-generated harmful factorsVSLoss of substance

Solution Approach 1:

Instead of discarding the Lewis acid as waste effluent, the patent recovers and reuses it. The extraction process separates the Lewis acid from the reaction medium, allowing it to be recovered, purified, and reused in subsequent catalytic cycles. This eliminates both impurity generation during distillation and the need to discard valuable Lewis acid material.

Inventive Principle:
Principle #34Discarding and recovering

3Manufacturing precision

If ion-exchange resin is used to extract metal cocatalyst, then purification is improved, but process complexity increases

Engineering Contradiction:
ImprovepurificationVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent introduces an ion-exchange resin as an intermediary substance to facilitate the extraction of metal cocatalyst from the reaction medium. The resin acts as a mediator that selectively binds to metal ions, enabling efficient separation and purification of the dinitrile product. While this adds a step, the resin can be regenerated and reused, managing the complexity through a standardized purification technique.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 process reduces impurity generation, prevents side reactions, and allows for the recovery and reuse of cocatalysts, enhancing process economics and environmental sustainability.

Implementation Method 1

treating the said second medium E2 by passing over an ion-exchange resin in order to extract at least the metal forming the cocatalyst

Methodology Applied
Scientific EffectIon exchange: Ion Exchange

Implementation Method 2

carrying out the hydrocyanation of an olefin, such as butadiene, to produce compounds comprising a nitrile functional group and an ethylenic unsaturation in the presence of a catalytic system comprising an organometallic complex

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

the catalytic system comprises a cocatalyst generally composed of a Lewis acid... compounds which accept electron pairs

Methodology Applied
Scientific EffectLewis acid catalysis:

Data Source

PatentUS8373001B2Method of producing dinitrile compounds
Publication Date: 2013.02.12 INV NYLON CHEMICALS AMERICAS LLC
  • US8373001B2 patent drawing
  • US8373001B2 patent drawing
  • US8373001B2 patent drawing

AI summary

The present invention relates to a process for the manufacture of compounds comprising two nitrile functional groups. It relates more particularly to a process for the manufacture of dinitrile compounds from compounds comprising a nitrile functional group and an ethylenic unsaturation in the presence of a catalytic system comprising an organometallic complex and a cocatalyst of the Lewis acid type. The process of the invention comprises a stage of treatment of the reaction medium resulting from the hydrocyanation which makes it possible to extract and recover the metal element of the Lewis acid.