Greener Dye Synthesis: Continuous,Solvent-Free Synthesis of Commodity Perylene Diimides by Twin-Screw Extrusion |
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Authors: | Dr. Qun Cao Dr. Deborah E. Crawford Chengcheng Shi Prof. Stuart L. James |
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Affiliation: | School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, 39–123 Stranmillis Road, Belfast, BT9 5AG Northern Ireland, UK |
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Abstract: | A continuous, scalable, and solvent-free method for the synthesis of various naphthalic imides and perylene diimides (PDIs) using twin-screw extrusion (TSE) is reported. Using TSE, naphthalic imides were obtained quantitatively without the need for excess amine reactant or product purification. With good functional-group tolerance, alkyl and benzyl amine derived PDIs (incl. commercial dyes) were obtained in 50–99 % yield. Use of K2CO3, enabled synthesis of more difficult aniline-derived PDIs. Furthermore, an automated continuous TSE process for Pigments Black 31 and 32 is demonstrated, with a throughput rate of about 1500 g day−1, corresponding to a space time yield of about 30×103 kg m−3 day−1, which is 1–2 orders of magnitude greater than for solvent-based batch methods. These methods provide substantial waste reductions and improved efficiency compared to conventional solvent-based methods. |
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Keywords: | Farbstoffe/Pigmente Mechanochemie Imide Festkörperreaktionen Synthesemethoden |
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