Continuous Cyclic Carbonate Preparation via Halide Recycling

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Solution Overview

Problem

Existing continuous processes for preparing cyclic carbonate products face challenges such as high energy consumption, by-product formation, and thermal deactivation of catalysts due to exothermal reactions, particularly in tubular reactors.

Innovation Solution

A process involving a supported dimeric aluminium salen complex activated by a halide compound, where carbon dioxide reacts with an epoxide compound in a suspension of liquid cyclic carbonate, allowing for efficient heat transfer and catalyst reactivation, reducing the need for external cooling and nitrogen gas, and achieving high yields and selectivity through recycling of reactants and catalysts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If a tubular reactor is used for continuous preparation of cyclic carbonate, then the reaction can proceed under near-ambient temperature and atmospheric pressure, but external cooling is required to avoid overheating due to exothermal reaction

Engineering Contradiction:
Improvereaction temperatureVSAvoidenergy consumption
Core Design Contradiction:
TemperatureVSUse of energy by moving object

Solution Approach 1:

The exothermal heat of reaction, which was previously a harmful factor requiring external cooling, is converted into a beneficial heating source. The reaction mixture itself provides the heat needed to maintain the reaction temperature, eliminating the need for external heating and reducing energy consumption.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The reaction system becomes self-regulating through the exothermal reaction. The heat generated by the reaction itself maintains the required temperature, making the system self-sufficient for thermal management without requiring external cooling or heating systems.

Inventive Principle:
Principle #25Self-service

2Temperature

If a tubular reactor is used for continuous preparation of cyclic carbonate, then the reaction can proceed under near-ambient temperature and atmospheric pressure, but external cooling is required to avoid overheating due to exothermal reaction

Engineering Contradiction:
Improvereaction temperatureVSAvoidreactor complexity
Core Design Contradiction:
TemperatureVSDevice complexity

Solution Approach 1:

The exothermal heat, previously requiring complex external cooling systems, is converted into a beneficial feature that simplifies the reactor design by eliminating the need for external cooling infrastructure.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The reaction system self-regulates its temperature through the exothermal reaction, making the system self-sufficient and eliminating the need for external temperature control systems, thereby reducing device complexity.

Inventive Principle:
Principle #25Self-service

3Manufacturing precision

If supported dimeric aluminium salen complex is used as catalyst, then high selectivity and yield to cyclic carbonate can be achieved, but catalyst deactivation occurs due to thermal effects

Engineering Contradiction:
Improveselectivity to cyclic carbonateVSAvoidcatalyst stability
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The thermal effects that previously caused catalyst deactivation are converted into a beneficial heating source that maintains reaction temperature without requiring external heating, thereby preventing thermal deactivation while maintaining high selectivity.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The reaction system self-regulates temperature through exothermal reaction, preventing thermal runaway and catalyst deactivation while maintaining optimal reaction conditions for high selectivity and yield.

Inventive Principle:
Principle #25Self-service

4Productivity

If continuous process is used for cyclic carbonate preparation, then productivity is improved, but by-product formation increases due to thermal effects

Engineering Contradiction:
Improveproduction rateVSAvoidby-product formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The exothermal heat, previously causing by-product formation through thermal side reactions, is converted into a beneficial heating source that maintains optimal reaction temperature without external heating, thereby eliminating thermal by-products while maintaining high productivity.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The reaction system self-regulates temperature through exothermal reaction, preventing thermal runaway and by-product formation while maintaining continuous operation and high productivity.

Inventive Principle:
Principle #25Self-service

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 achieves high yields (up to 95%) and purity (above 99%) of cyclic carbonate products while minimizing energy consumption and by-product formation, maintaining catalyst activity through halide recycling and efficient separation techniques.

Implementation Method 1

reacting an epoxide compound with carbon dioxide in the presence of a supported dimeric aluminium salen complex

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

The liquid cyclic carbonate product is an efficient heat transfer medium which avoids local hot spots and possible thermal deactivation of the catalyst complex

Methodology Applied
Scientific EffectHeat transfer: Conduction (thermal)

Implementation Method 3

a supported dimeric aluminium salen complex which complex is activated by a halide compound

Methodology Applied
Scientific EffectChemical activation: Chemical Bonding

Data Source

PatentEP3728213B1Process to continuously prepare a cyclic carbonate
Publication Date: 2021.10.27 NEW GREEN WORLD BV
  • EP3728213B1 patent drawingFigure 1~2
  • EP3728213B1 patent drawingFigure 3
  • EP3728213B1 patent drawing

AI summary

Process to continuously prepare a cyclic carbonate product by reacting an epoxide compound with carbon dioxide in the presence of a supported dimeric aluminium salen complex which complex is activated by a halide compound comprising the following steps, (a) contacting carbon dioxide with the epoxide compound in a suspension of liquid cyclic carbonate and the supported dimeric aluminium salen complex which complex is activated by a halide compound, (b) separating part of the cyclic carbonate product from the supported dimeric aluminium salen complex, (c) separating the halide compound from the cyclic carbonate product to obtain purified cyclic carbonate product, (d) use all or part of the halide compound as obtained in step (c) to activate deactivated supported dimeric salen complex.