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Greener Dye Synthesis: Continuous, Solvent‐Free Synthesis of Commodity Perylene Diimides by Twin‐Screw Extrusion
Author(s) -
Cao Qun,
Crawford Deborah E.,
Shi Chengcheng,
James Stuart L.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913625
Subject(s) - perylene , yield (engineering) , extrusion , amine gas treating , solvent , chemistry , aniline , combinatorial chemistry , materials science , organic chemistry , molecule , composite material
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 K 2 CO 3 , 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 30×10 3 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.