Sulfolane Extractive Distillation for EG–EGDA Azeotrope Separation

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Solution Overview

Problem

Existing methods struggle to efficiently separate ethylene glycol (EG) and ethylene glycol diacetate (EGDA) due to their formation of azeotropic mixtures, leading to low purity and high production costs, especially when using toluene or benzene as entrainers.

Innovation Solution

Employing sulfolane as an entrainer in a two-stage distillation process involving an extractive distillation tower and an entrainer recovery tower, with specific operating conditions and plate configurations to achieve high purity separation of EG and EGDA.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional distillation is used to separate EG and EGDA, then the separation process is simple, but the purity of products cannot reach high levels due to azeotropic mixture formation

Engineering Contradiction:
Improvepurity of EG and EGDAVSAvoidcomplexity of separation process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent introduces a third component (entrainer) as an intermediary substance to facilitate the separation of EG and EGDA. The entrainer selectively interacts with one component of the azeotropic mixture, disrupting the azeotrope and enabling high-purity separation through distillation. This mediator approach transforms an otherwise intractable separation problem into a solvable process.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent employs extractive distillation which involves changing the physical-chemical parameters of the system by introducing an entrainer with specific properties (boiling point, selectivity). This parameter change allows the separation of components that cannot be separated by conventional distillation alone, achieving high purity products despite the added process complexity.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If toluene is used as extractant to separate EG and EDGA, then the separation effectiveness is improved, but the input cost increases and specific operating conditions are not disclosed

Engineering Contradiction:
Improvepurity of separated productsVSAvoidinput cost and process complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent seeks to replace expensive extractants like toluene with cheaper alternatives. The entrainer used in this patent is selected to be less costly than toluene while maintaining or improving separation effectiveness. This reduces the input cost associated with the extractant, making the process more economically viable.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent optimizes operating parameters including the ratio of entrainer to feed (5-7:1), tower pressures (7-8 kPa at top of extractive distillation tower), and temperatures (120-130°C at top, 160-170°C at bottom) to achieve high purity separation while controlling costs. These parameter specifications provide a complete, reproducible process.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If excess acetic acid is added to make EG completely converted, then the azeotropic mixture problem is solved, but the input cost increases and the process becomes more complicated with additional reactors

Engineering Contradiction:
Improvepurity of EGDA productVSAvoidnumber of reactors and process steps
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

Instead of adding more reaction steps or excess reagents, the patent extracts the separation problem from the reaction process. By using extractive distillation with an entrainer, the patent separates EG and EGDA directly from the reaction mixture without requiring complete conversion through excess acetic acid or additional reactors. This decouples the reaction and separation functions.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the separation approach from chemical conversion (using excess acetic acid) to physical separation (extractive distillation). This parameter change in the separation mechanism avoids the need for additional reactors and excess reagents, simplifying the overall process while maintaining high product purity.

Inventive Principle:
Principle #35Parameter changes

4Manufacturing precision

If extractive distillation with sulfolane is used to achieve high purity separation, then the purity and yield of products are improved, but the energy consumption and process complexity increase

Engineering Contradiction:
Improvepurity of EG and EGDAVSAvoidenergy consumption of distillation process
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The patent optimizes distillation parameters including operating pressure (7-8 kPa), temperatures (120-130°C at top, 160-170°C at bottom), and entrainer-to-feed ratio (5-7:1) to minimize energy consumption while achieving high purity separation. These optimized parameters reduce the energy penalty associated with extractive distillation compared to conventional approaches.

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

The method achieves EG and EGDA purities of 99.50% and 99.90% respectively, with improved yield and reduced energy consumption, while minimizing entrainer loss and process costs.

Implementation Method 1

obtaining the EG and a mixture of the EDGA and the sulfolane through separating a mixture of the EG and the EDGA under an action of the sulfolane by an extractive distillation tower

Methodology Applied
Scientific EffectExtractive distillation: Distillation

Implementation Method 2

utilizing the feature that EG is difficult to dissolve in toluene while the EDGA is easily to dissolve in the toluene

Methodology Applied
Scientific EffectSolubility difference: Solvation

Implementation Method 3

obtaining the EDGA and the sulfolane through separating the mixture of the EDGA and the sulfolane by an entrainer recovery tower

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 4

obtaining recycled sulfolane through cooling the sulfolane by a heat exchanger

Methodology Applied
Scientific EffectHeat exchange: Heat Exchanger

Implementation Method 5

cooling the sulfolane by a heat exchanger, and mixing the recycled sulfolane with fresh sulfolane

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentUS12428367B2Methods for separating the binary azeotropic mixture of ethylene glycol and ethylene glycol diacetate with sulfolane entrainer
Publication Date: 2025.09.30 CHANGZHOU UNIV
  • US12428367B2 patent drawing
  • US12428367B2 patent drawing

AI summary

Method for separating ethylene glycol (EG) and ethylene glycol diacetate (EGDA) with sulfolane entrainer, including: obtaining EG and a mixture of EGDA and sulfolane through separating a mixture of EG and EGDA under an action of sulfolane by an extractive distillation tower; obtaining EGDA and sulfolane through separating the mixture of the EGDA and the sulfolane by an entrainer recovery tower; and obtaining recycled sulfolane through cooling the sulfolane by a heat exchanger, and mixing the recycled sulfolane with fresh sulfolane and circulating into the extractive distillation tower for recycling. Through the method, a yield of the EG is greater than or equal to 99.50% and a mass purity of the EG is greater than or equal to 99.50%, and a yield of the EGDA is greater than or equal to 99.80% and a mass purity of the EGDA is greater than or equal to 99.90%.