Diels-Alder reactions of myrcene using intensified continuous-flow reactors

Area of Science:

• Organic Chemistry
• Chemical Engineering
• Sustainable Chemistry

Background:

• The Diels-Alder reaction is a fundamental organic chemistry transformation.
• Myrcene, a naturally occurring terpene, is a versatile butadiene derivative.
• Scaling up chemical synthesis efficiently is crucial for industrial applications.

Purpose of the Study:

• To explore the Diels-Alder reaction of myrcene with various dienophiles.
• To develop a continuous-flow synthesis for a myrcene-based surfactant.
• To demonstrate the advantages of continuous-flow reactors for process intensification.

Main Methods:

• Investigated Diels-Alder reactions using myrcene and diverse dienophiles.
• Scaled up the synthesis of a myrcene-acrylic acid adduct in a 105 mL plate-type continuous-flow reactor.
• Optimized reaction conditions for higher temperatures and shorter reaction times.

Main Results:

• Successfully synthesized a Diels-Alder adduct from myrcene and acrylic acid with surfactant properties.
• Achieved a daily throughput of 2.79 kg of the final product.
• Demonstrated the feasibility of continuous-flow processing for this synthesis.

Conclusions:

• Continuous-flow synthesis is a facile and efficient method for scaling up Diels-Alder reactions.
• This approach intensifies the synthesis protocol, enabling higher temperatures and shorter reaction times.
• The developed method provides a sustainable route for producing myrcene-based surfactants.