Ionic Liquid Purification of Olefins from Acetylenes

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Solution Overview

Problem

Current methods for purifying olefins from acetylenic compounds are costly, energy-intensive, and inefficient, leading to catalyst poisoning, product contamination, and explosive risks due to the formation of unstable copper or silver acetylides, and require complex regeneration processes.

Innovation Solution

The use of pyrrolidinium-based or piperidinium-based ionic liquid mixtures comprising copper (I) halide, which stabilizes copper (I) and selectively removes acetylenic compounds through absorption or extraction processes, preventing oxidation and acetylide formation, and allowing for simple and economical purification.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If partial hydrogenation of acetylenes into olefins using noble metal catalyst is used, then acetylenic compounds are removed from olefins, but over-hydrogenation occurs producing paraffins resulting in olefin loss and catalyst poisoning from carbon deposition

Engineering Contradiction:
Improveacetylene removal effectivenessVSAvoidolefin loss
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The invention changes the chemical environment parameters by using ionic liquids with specific cations (pyrrolidinium, piperidinium) and anions to create a selective coordination environment. This modifies the reaction parameters to achieve selective acetylene removal without over-hydrogenation, maintaining olefin integrity while removing acetylenic compounds

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The ionic liquid acts as an intermediary substance that facilitates selective interaction between copper(I) and acetylenic compounds. The ionic liquid mediates the removal process by forming stable complexes with acetylenes through copper(I), preventing direct harmful reactions while enabling selective separation without catalyst poisoning or olefin loss

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If solvent extraction using organic solvents like DMF or NMP is used, then acetylenes are separated from cracking process, but significant solvent loss occurs after multiple operations and selectivity of acetylenes over olefins is low

Engineering Contradiction:
Improveacetylene separation capabilityVSAvoidsolvent loss
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The invention changes the solvent system from conventional organic solvents (DMF, NMP) to ionic liquids with unique properties. The ionic liquid's low vapor pressure and high thermal stability change the physical parameters, eliminating solvent loss through evaporation while maintaining extraction efficiency and improving selectivity for acetylenes over olefins

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite material system consisting of ionic liquid combined with copper(I) halide. This composite provides both the extraction medium (ionic liquid) and the selective binding agent (copper(I)), creating a synergistic system that achieves high selectivity and prevents solvent loss simultaneously

Inventive Principle:
Principle #40Composite materials

3Reliability

If low temperature distillation is used to separate unsaturated compounds from saturated hydrocarbon mixtures, then separation is achieved, but energy consumption is high

Engineering Contradiction:
Improveseparation effectivenessVSAvoidenergy consumption
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The ionic liquid acts as a chemical intermediary that enables separation through selective complexation rather than physical distillation. By forming stable complexes with acetylenic compounds, the ionic liquid allows separation at ambient or mild temperatures, eliminating the need for energy-intensive low temperature distillation while achieving effective separation

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention replaces the mechanical/physical separation method (distillation requiring temperature control and energy input) with a chemical separation method based on selective complexation. The ionic liquid-copper(I) system chemically binds acetylenes, allowing separation through simple phase separation or filtration without energy-consuming distillation equipment

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

4Reliability

If molecular sieves are used to adsorb and remove unsaturated compounds, then CO and other unsaturated compounds are removed, but adsorption capacity is limited and high temperature and high vacuum pressure are required for stripping

Engineering Contradiction:
Improveunsaturated compound removalVSAvoidstripping process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention changes the adsorption mechanism from physical adsorption in molecular sieves to chemical complexation with ionic liquid-copper(I) system. This parameter change in the interaction mechanism allows for lower temperature operation and simpler stripping processes, as the complexation can be reversed under milder conditions without requiring high vacuum pressure

Inventive Principle:
Principle #35Parameter changes

5Reliability

If Cu(I) or Ag(I) salt is used for separation through reversible π-complexation, then acetylenic compounds are removed, but unstable copper- or silver-acetylides are produced creating explosion risks

Engineering Contradiction:
Improveacetylene removal selectivityVSAvoidexplosion risk from acetylide formation
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The ionic liquid serves as a protective intermediary that stabilizes copper(I) in solution and controls its reactivity. By dissolving copper(I) halide in the ionic liquid, the copper(I) is surrounded by ionic liquid molecules that prevent direct, uncontrolled reaction with acetylenes to form explosive acetylides, while still enabling selective complexation for removal

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The ionic liquid creates an inert chemical environment that stabilizes copper(I) and prevents formation of explosive acetylides. The ionic liquid's unique solvation properties and coordination chemistry create a controlled environment where copper(I) can selectively complex with acetylenes for removal without forming unstable, explosive compounds

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

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 method significantly improves the selective removal rate of acetylenic compounds, maintains capacity over time, and reduces the risk of explosion, with low loss rates and easy regenerability, compared to existing adsorption and membrane separation processes.

Implementation Method 1

removal of acetylenic compounds from olefin by using pyrrolidinium-based or piperidinium-based ionic liquid mixtures comprising copper (I) halide

Methodology Applied
Scientific EffectAbsorption: Absorption (physical)

Implementation Method 2

stabilizes copper (I) and selectively removes acetylenic compounds through absorption or extraction processes, preventing oxidation and acetylide formation

Methodology Applied
Scientific EffectStabilization:

Data Source

PatentUS8143470B2Method of purifying olefins using pyrrolidinium-based or piperidinium-based ionic liquids comprising copper (I) halide
Publication Date: 2012.03.27 KOLON INDUSTRIES INC
  • US8143470B2 patent drawing
  • US8143470B2 patent drawing
  • US8143470B2 patent drawing

AI summary

The present invention relates to a method of purifying olefin, the method comprising removing a small amount of acetylenic compounds contained in olefin by using pyrrolidinium-based or piperidinium-based ionic liquid mixtures comprising copper (I) halide. According to the method of the present invention, copper (I) halide is stabilized by pyrrolidinium-based or piperidinium-based ionic liquids, suppressing the oxidation of Cu(I) into Cu(II), whereby the capacity of removing acetylenic compounds can be maintained for a long time and the selective removal rate of acetylenic compounds to olefin can be significantly improved. In addition, since the ionic liquid mixtures comprising copper (I) halide used in the method of the present invention can be applied to both absorption and extraction processes, it can effectively remove acetylenic compounds from olefin in a more simple and economical way compared to the existing adsorption and membrane separation processes.