Diethylene Glycol Ether Production via Solid Acid Catalyst and Vacuum Distillation

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Solution Overview

Problem

Current methods for producing diethylene-glycol tert-butyl ether (DEGtBE) face challenges such as high costs due to expensive raw materials, generation of byproducts, and difficulties in improving selectivity and purity, particularly with traditional epoxide and olefin-based methods, and the use of strong acid catalysts which are corrosive and exacting.

Innovation Solution

The method involves mixing isobutylene (IB) and diethylene glycol (DEG) with a solid acid catalyst, specifically an acidic cation exchanged resin, and processing the mixture through two stages of vacuum distillation under controlled temperature and pressure conditions to achieve high selectivity and purity of DEGtBE, while recycling the byproduct diethylene-glycol di-tert-butyl ether (DEGDtBE) for transetherification to enhance IB conversion and reduce byproduct generation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If traditional epoxide and ether method is used to produce DEGtBE, then production scale can be increased, but selectivity and purity deteriorate due to generation of multiple byproducts including multi-EG butyl ether

Engineering Contradiction:
Improveproduction scaleVSAvoidselectivity and purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent segments the reaction process into two distinct stages: first producing DEG butyl ether as the main product, then converting it to DEGtBE through transetherification. This segmentation allows each stage to be optimized independently, achieving high selectivity (90% or more) and purity while maintaining production scale.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent changes reaction parameters including using solid acid catalysts with specific acidity (0.01-1.00 mmol/g), controlling reaction temperature (30-150°C), and adjusting reactant ratios (DEG/IB= between 0.5-10.0) to achieve high selectivity and purity of DEGtBE while maintaining productive output.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If olefin and glycol etherification method is used, then IB= solving amount is enhanced and reaction activity is heightened, but byproduct generation increases and separation becomes difficult due to azeotrope formation between ether alcohol and double ether

Engineering Contradiction:
ImproveIB= solving amountVSAvoidbyproduct generation and separation difficulty
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and removes the harmful azeotrope formation issue by using solid acid catalysts that prevent ether alcohol byproduct generation, thereby eliminating the separation difficulty that plagues conventional olefin etherification methods.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent uses solid acid catalysts that can be easily separated and reused, replacing the need for complex separation systems required by conventional methods that generate difficult-to-separate byproducts.

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

3Ease of manufacture

If strong acid catalyst (H2SO4) is used for dehydration synthesis, then reaction can proceed at 140-180°C, but corrosion increases and operation becomes exacting

Engineering Contradiction:
Improvereaction feasibilityVSAvoidcorrosion and operational complexity
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent introduces solid acid catalysts as intermediaries that mediate the dehydration synthesis reaction, replacing strong liquid acid catalysts like H2SO4. These solid catalysts provide the necessary acidity while being non-corrosive and easily separable, thus eliminating the harmful effects of strong acids.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent replaces the chemical mechanism of strong acid catalysis with a solid acid catalyst system, substituting a corrosive chemical system with a mechanically separable solid catalyst system that achieves the same reaction function without the harmful side effects.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

4Quantity of substance

If EG ether is used as solvent, then cost is reduced, but environmental protection deteriorates due to harm to human body

Engineering Contradiction:
Improvecost effectivenessVSAvoidenvironmental and health impact
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameter of the glycol ether product by controlling the reaction to produce DEGtBE with specific molecular structure and properties, creating a product that maintains the cost-effectiveness of EG ethers while improving environmental and health safety profiles.

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 results in a cost-effective production of DEGtBE with high selectivity and purity, effectively recycling byproducts and optimizing IB conversion, thereby addressing the limitations of existing methods.

Implementation Method 1

mixing isobutylene (IB) and diethylene glycol (DEG) with a solid acid catalyst, specifically an acidic cation exchanged resin

Methodology Applied
Scientific EffectAcid catalysis: Catalysis

Implementation Method 2

processing the mixture through two stages of vacuum distillation under controlled temperature and pressure conditions

Methodology Applied
Scientific EffectVacuum distillation: Vacuum Distillation

Data Source

PatentUS8269049B2Method of producing diethylene-glycol tert-butyl ether using isobutylene and diethylene glycol
Publication Date: 2012.09.18 CHINESE PETROLEUM CORP TAIWAN
  • US8269049B2 patent drawing
  • US8269049B2 patent drawing
  • US8269049B2 patent drawing

AI summary

The present invention fabricates diethylene-glycol tert-butyl ether (DEGtBE) by using isobutylene and diethylene glycol (DEG) coordinated with an acidic cation exchanged resin as catalyst. Through two stages of vacuum distillations, highly selective and pure DEGtBE is produced. Moreover, a byproduct of diethylene-glycol di-tert-butyl ether (DEGDtBE) can be recycled.