Continuous E-cyclooctene Production via Liquid-Liquid Extraction

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Solution Overview

Problem

Existing methods for producing E-cyclooctene are not continuous, efficient, and scalable, often requiring additional unit operations and becoming saturated with silica gel, which complicates the process.

Innovation Solution

A continuous method involving liquid-liquid extraction where E-cyclooctene is produced by contacting an organic liquid containing Z-cyclooctene with an aqueous liquid, utilizing a third compound like silver nitrate to enhance solubility and facilitate extraction, eliminating the need for silica gel and allowing easy scaling.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If batch extraction with silica gel is used to separate trans-cyclooctene, then separation is achieved, but the process becomes complex and silica gel becomes saturated over time

Engineering Contradiction:
Improveseparation efficiencyVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention extracts the separation function from the complex batch process with silica gel and implements it as a continuous liquid-liquid extraction process using aqueous silver nitrate solution, eliminating the saturation problem and simplifying the overall process while maintaining high separation efficiency

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention transitions from batch extraction to continuous liquid-liquid extraction, where the aqueous silver nitrate solution continuously contacts the organic phase to extract trans-cyclooctene, preventing silica gel saturation and enabling sustained high-efficiency separation without interruption

Inventive Principle:
Principle #20Continuity of useful action

2Productivity

If additional unit operations are added to produce E-cyclooctene, then production capability is improved, but process complexity increases

Engineering Contradiction:
Improveproduction capabilityVSAvoidnumber of unit operations
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention merges the isomerization and separation functions into a single continuous process where Z-cyclooctene is isomerized to E-cyclooctene in the organic phase, and the E-isomer is simultaneously extracted by the aqueous silver nitrate solution, eliminating the need for multiple separate unit operations

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The aqueous silver nitrate solution serves multiple functions: it acts as a extracting agent for separation, a sensitizer for photoisomerization, and a means to maintain continuous operation, thereby reducing the number of required unit operations while enhancing production capability

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Manufacturing precision

If silica gel is used for extraction, then separation is achieved, but scaling up becomes difficult

Engineering Contradiction:
Improveseparation qualityVSAvoidscalability
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention employs liquid-liquid extraction using aqueous silver nitrate solution instead of solid silica gel, allowing the process to be easily scaled up by simply increasing the flow rates and volumes of the liquid phases without the complexity of scaling solid phase extraction systems

Inventive Principle:
Principle #29Pneumatics and hydraulics

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 enables efficient and continuous production of E-cyclooctene with improved solubility and purity, eliminating the need for additional steps and silica gel saturation, thus facilitating easy scaling and high yield.

Implementation Method 1

A continuous method involving liquid-liquid extraction where E-cyclooctene is produced by contacting an organic liquid containing Z-cyclooctene with an aqueous liquid

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 2

utilizing a third compound like silver nitrate to enhance solubility and facilitate extraction

Methodology Applied
Scientific EffectSolubility enhancement by silver nitrate: Solvation

Implementation Method 3

A direct route to synthesize E-cyclooctenes is by photo-isomerization of Z-cyclooctenes ('cis-cyclooctenes') with ultraviolet light (UV light) with a wavelength in the range of 254 nm

Methodology Applied
Scientific EffectPhoto-isomerization: Photochromism

Data Source

PatentEP3357903B1Method for a continuous production of a z-cyclooctene
Publication Date: 2020.11.04 STICHTING KATHOLIEKE UNIV
  • EP3357903B1 patent drawingFigure 1
  • EP3357903B1 patent drawingFigure 2
  • EP3357903B1 patent drawingFigure 3

AI summary

The invention provides a method for a continuous production of a first compound (12), the method comprising continuously providing a first liquid (10) to a mixing zone (110) in an extraction unit (100), wherein the first liquid (10) comprises the first compound (12) and a second compound (13), mixing in the mixing zone (110) the first liquid (10) with a second liquid (20), wherein the first liquid (10) and the second liquid (20) are not miscible, wherein the first compound (12), optionally in combination with a third compound (22), has a higher solubility in the second liquid (20) than the second compound (13) optionally in combination with the third compound (22), wherein in a first withdrawal zone (120) in the extraction unit (100), in fluid contact with the mixing zone (110), at least part of the first liquid (10) or the second liquid (20) is continuously removed from the extraction unit (100), wherein the first compound (12) is an E-cyclooctene, wherein the second compound (13) is a Z-cyclooctene, wherein the first liquid (10) is an organic liquid (11), wherein the second liquid (20) is an aqueous liquid (21), and wherein the third compound (22) is a metal salt (23). The invention further provides a system (1) for a continuous production of such first compound (12).