Continuous Flow Reactor for Carbonate Ester Synthesis

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Solution Overview

Problem

Conventional batch processes for preparing organic carbonate esters are expensive and difficult to scale up for use in rechargeable battery systems, necessitating the development of more efficient methods.

Innovation Solution

A continuous process involving the contact of an alcohol or epoxide with a reactive carbonyl source, such as an alkyl chloroformate or carbon dioxide, in the presence of a catalyst within a continuous flow reactor at controlled temperatures, followed by purification through distillation, to produce organic carbonate solvents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional batch processes are used to prepare organic carbonate esters, then the process can be implemented with standard equipment, but the production cost increases and scalability becomes difficult

Engineering Contradiction:
Improveease of manufactureVSAvoidproductivity
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent applies continuous flow processing instead of batch processing to prepare organic carbonate esters. The reaction is conducted continuously through a flow reactor, allowing for sustained production without the interruptions inherent in batch processes. This continuity enables better scalability and reduced production costs while maintaining ease of manufacture with standard equipment.

Inventive Principle:
Principle #20Continuity of useful action

2Ease of manufacture

If conventional batch processes are used to prepare organic carbonate esters, then the process can be implemented with standard equipment, but scaling up becomes difficult

Engineering Contradiction:
Improveease of manufactureVSAvoidscalability
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The continuous flow process allows for easy scaling by simply increasing the flow rate or extending the reaction time, without requiring a complete redesign of the process. The modular nature of continuous flow reactors enables straightforward scale-up from laboratory to industrial production, addressing the scalability limitation of conventional batch processes.

Inventive Principle:
Principle #20Continuity of useful action

3Productivity

If continuous flow processing is used to prepare organic carbonate esters, then productivity and scalability are improved, but the process complexity increases

Engineering Contradiction:
ImproveproductivityVSAvoiddevice complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

While continuous flow processing does introduce some additional complexity compared to batch processing, the patent demonstrates that this complexity is justified by the significant improvements in productivity and scalability. The continuous flow reactor system, though more complex, provides better process control, enhanced safety, and improved efficiency that outweigh the additional device complexity.

Inventive Principle:
Principle #20Continuity of useful action

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 the efficient and scalable production of organic carbonate esters, achieving high conversion rates and maximizing the use of reactants while minimizing byproducts, thus addressing the cost and scalability issues of conventional batch processes.

Implementation Method 1

contacting an alcohol or epoxide with a reactive carbonyl source (e.g., an alkyl chloroformate, a fluoroalkyl chloroformate, carbonyldiimidazole (CDI), or carbon dioxide) in the presence of a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

in a continuous flow reactor at a temperature in the range of about 20° C. to about 160° C.

Methodology Applied
Scientific EffectHeating: Heating

Implementation Method 3

The crude product is then purified, e.g., by distillation to obtain the organic carbonate compound of Formula (I)

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS11708345B2Continuous method for preparing carbonate esters
Publication Date: 2023.07.25 UCHICAGO ARGONNE LLC
  • US11708345B2 patent drawing
  • US11708345B2 patent drawing
  • US11708345B2 patent drawing

AI summary

In one embodiment, a continuous process for preparing organic carbonate solvent of Formula (I) as described herein comprises contacting a first reactant (an alcohol) with a reactive carbonyl source (carbonyldiimidazole (CDI) or an alkylchloroformate) in the presence of a catalyst in reaction stream flowing through a continuous flow reactor at temperature 20° C. to about 160° C. and at a flow rate providing a residence time in the range of about 0.1 minute to about 24 hours; collecting a reactor effluent exiting from the continuous flow reactor; recovering a crude product from the reactor effluent; and distilling the crude product to obtain the organic carbonate compound of Formula (I). In another embodiment, the first reactant is an epoxide and the carbonyl source is carbon dioxide.