Regioselective Cellulose Ester Production via Halide Ionic Liquid Recycling

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Solution Overview

Problem

The production of ionic liquids for use in cellulose esterification processes is hindered by high costs and inefficiencies in recycling, as well as the presence of residual metals, sulfur, and halides in existing methods, which affect the quality and feasibility of cellulose ester production.

Innovation Solution

A process involving the use of halide ionic liquids for dissolving cellulose, followed by esterification with acylating reagents, and subsequent separation and recycling of the ionic liquid, allowing for the production of regioselectively substituted cellulose esters with improved properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods are used to produce ionic liquids, then ionic liquids can be obtained, but residual metals, sulfur, and halides are present affecting product quality

Engineering Contradiction:
Improvepurity of ionic liquidVSAvoidresidual metals, sulfur, and halides
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and removes harmful residual metals, sulfur, and halides from the ionic liquid through purification steps including filtration and washing processes, thereby obtaining high-purity ionic liquid suitable for cellulose esterification

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the purity parameter of the ionic liquid by implementing multiple purification stages, transforming the ionic liquid from a crude product containing impurities to a refined product meeting strict purity requirements for pharmaceutical applications

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If ionic liquids are used in cellulose esterification, then regioselectively substituted cellulose esters can be produced, but the process cost increases due to ionic liquid expense

Engineering Contradiction:
Improveregioselectivity of cellulose esterVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent recovers and reuses the ionic liquid catalyst after the esterification reaction through separation and purification steps, converting it from a consumable expense to a recyclable catalyst, thereby reducing overall production costs while maintaining regioselectivity

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The ionic liquid serves a dual function as both reaction medium and catalyst, and its self-recycling capability eliminates the need for continuous external supply, reducing operational costs

Inventive Principle:
Principle #25Self-service

3Productivity

If ionic liquids are recycled, then costs are reduced, but recycling efficiency is insufficient in existing methods

Engineering Contradiction:
Improverecycling efficiencyVSAvoidrecycling loss
Core Design Contradiction:
ProductivityVSLoss of energy

Solution Approach 1:

The patent implements a feedback mechanism where the recycled ionic liquid is characterized and its quality is monitored, and this information feeds back into the purification process optimization to maintain high recycling efficiency and minimize losses

Inventive Principle:
Principle #23Feedback

Solution Approach 2:

The patent uses composite separation systems combining multiple purification techniques to achieve high-efficiency ionic liquid recycling with minimal energy loss and maximum recovery rate

Inventive Principle:
Principle #40Composite materials

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 enables the efficient production of regioselectively substituted cellulose esters with specific Rth values, enhancing their suitability for applications such as compensation films in liquid crystalline displays, while also recycling and purifying the ionic liquids to reduce waste and costs.

Implementation Method 1

introducing a reaction medium comprising cellulose, a halide ionic liquid and a binary component into an esterification zone

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

combining at least one acylating reagent with said reaction medium in said esterification zone to esterify at least a portion of said cellulose

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Implementation Method 3

contacting said acylated cellulose solution with a non-solvent to cause at least a portion of said cellulose ester to precipitate

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Data Source

PatentEP2313438B1Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom
Publication Date: 2019.09.18 EASTMAN CHEM CO
  • EP2313438B1 patent drawingFigure 1
  • EP2313438B1 patent drawingFigure 2
  • EP2313438B1 patent drawingFigure 3

AI summary

This invention relates to novel compositions comprising regioselectively substituted cellulose esters. One aspect of the invention relates to processes for preparing regioselectively substituted cellulose esters from cellulose dissolved in ionic liquids. Another aspect of the invention relates to the utility of regioselectively substituted cellulose esters in applications such as protective and compensation films for liquid crystalline displays.