Synthesis of new heterocyclic resveratrol analogues in milli- and microreactors: intensification of the Wittig reaction

• Milena Mlakić^a, Lucija Rajič^a,b, Anabela Ljubić^b, Vitomir Vušak^b, Bruno Zelić^c,d, Martin Gojun^c, Ilijana Odak^e, Ivona Čule^e, Ivana Šagud^b, Anita Šalić^c, Irena Škorić^a

• ^aDepartment of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10 000, Zagreb, Croatia
• ^bPliva R&D, Teva Pharmaceutical Industries Ltd, Prilaz baruna Filipovića 29, HR-10 000, Zagreb, Croatia
• ^cDepartment of Reaction Engineering and Catalysis, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10 000, Zagreb, Croatia
• ^dDepartment of Packaging, Recycling and Environmental Protection, University North, Trg dr. Žarka Dolinara 1, HR-48 000, Koprivnica, Croatia
• ^eDepartment of Chemistry, Faculty of Science and Education, University of Mostar, Matice hrvatske bb, 88 000, Mostar, Bosnia and Herzegovina

Resveratrol is a natural bioactive non-flavonoid polyphenol that protects from cardiovascular disease, neurodegenerative diseases and various cancers. Unfortunately, the amounts of resveratrol in plants are low and therefore, chemical synthesis is still the main way to obtain this valuable structure. In this work, Wittig reaction was chosen as the synthetic route for the study on technology influence in batch vs. micro- or milliflow reactors during the production of new resveratrol-like compounds. A series of reactions was carried out by batch synthesis, and intensified in a milli- and a microreactor, changing the reaction conditions to increase the efficiency and productivity of the process. Results were compared based on conversion, yield, productivity and trans/cis ratio. Similar yields and conversions were obtained in all reaction systems, but in much shorter time in the milli- and microscale compared to the batch reactor. On the other hand, higher productivities were obtained in the millireactor and microreactor, making them better systems for the proposed reactions of new heterocyclic resveratrol analogues synthesis.

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