Cyclopropane Synthesis via Copper Catalysis and Microreactor Control
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Solution Overview
Problem
The high cost and environmental hazards associated with using rhodium and palladium catalysts in the production of cyclopropane derivatives, along with the need for a more efficient and cost-effective method that minimizes waste and energy consumption, drive the need for an alternative catalytic process.
Innovation Solution
The use of copper metal or copper oxide as a catalyst in a continuous process for the addition of carbenes to olefins, eliminating the need for separation and reducing the risk of hazardous reactions by employing a microreactor system, which allows for controlled conditions and efficient production of cyclopropane derivatives.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If rhodium or palladium complex catalysts are used for carbene addition to olefins, then the production of cyclopropane derivatives is achieved, but the cost of the process increases significantly
Solution Approach 1:
The patent replaces expensive rhodium or palladium complex catalysts with inexpensive copper metal or copper oxide catalysts. The copper catalyst can be used in its metallic form or as copper oxide, both of which are significantly cheaper than precious metal complexes. The catalyst may be used in disposable form or regenerated in situ, eliminating the need for expensive catalyst recovery and purification processes.
2Reliability
If metal complex catalysts are used for carbene addition, then the reaction proceeds effectively, but a separation step is required to remove the catalyst from the product
Solution Approach 1:
The patent extracts the catalyst function from complex metal complexes to simple copper metal or copper oxide. The copper catalyst can be easily separated from the reaction mixture by filtration or decantation, or it can be immobilized on a solid support for easy removal. This eliminates or simplifies the separation step required when using soluble metal complex catalysts.
3Reliability
If diazo compounds are used to generate carbenes, then the carbene addition reaction can proceed, but the risk of hazardous reactions and explosions increases
Solution Approach 1:
The patent introduces copper metal or copper oxide as an intermediary catalyst that facilitates carbene generation from diazo compounds under milder and safer conditions. The copper catalyst enables the reaction to proceed at lower temperatures and with better control, reducing the risk of runaway reactions and explosions associated with thermal decomposition of diazo compounds.
4Reliability
If conventional batch processes are used for cyclopropane derivative production, then the reaction can be carried out, but waste generation and energy consumption increase
Solution Approach 1:
The patent employs a continuous flow process where the reaction mixture passes through a reactor containing copper catalyst. This continuous operation allows for better control of reaction parameters, improved heat and mass transfer, and reduced waste generation. The continuous process enables better integration with downstream separation and purification steps, minimizing energy consumption and waste treatment requirements.
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 provides an economically favorable and safer method for producing cyclopropane derivatives, reducing waste and energy consumption, while avoiding the use of expensive transition metal catalysts and minimizing the risk of hazardous reactions.
Implementation Method 1
copper metal or copper oxide as a catalyst... copper metal and copper oxide have a catalytic effect in the addition of certain carbenes to olefins
Implementation Method 2
The use of copper metal or copper oxide as a catalyst in a continuous process... employing a microreactor system, which allows for controlled conditions
Data Source
AI summary
A process for the preparation of a cyclopropane derivative of Formula (I), by reacting an olefin of Formula (II), with a carbene of the formula :CR1 R2, in a reaction vessel, optionally in the presence of a solvent, wherein, R1 and R2 are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, -C(O)R7 or -NR8 2; R3, R4, R5 and R6 are each independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, aryl, aryloxy, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, -C(O)R9, -NR10 2, -SR11, -S(O)R11, or -SO2R11, or R3 and R6 are as defined above and R4 and R5 together form a ring, which ring is carbocyclyl, heterocyclyl, aromatic or heteroaromatic; R7 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy, heteroaryl or -NR10 2; R8 is hydrogen, C1-C6 alkyl, C1 -C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; R9 is hydrogen, hydroxy, C1-C6 alkyl, C1 -C6 alkoxy, aryl, aryloxy or heteroaryl; R10 is hydrogen, C1 -C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl, heterocyclyl or C(O)R12; R11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; and R12 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, or aryloxy, in the presence of copper metal or copper oxide, wherein the process is a continuous process.