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    Greener dye synthesis: continuous, solvent-free synthesis of commodity perylene diimides by twin-screw extrusion

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    Crawford_Angewandte_Chemie (1.267Mb)
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    Publication date
    2020-03
    Author
    Cao, Q.
    Crawford, Deborah E.
    Shi, C.
    James, S.L.
    Keyword
    Continuous extrusion
    Mechanochemistry
    Naphthalic imides
    Perylene diimides
    Solventless reactions
    Rights
    © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Cao Q, Crawford DE, Shi C et al (2020) Greener dye synthesis: continuous, solvent-free synthesis of commodity perylene diimides by twin-screw extrusion. Angewandte Chemie International Edition. 132(11): 4508-4513, which has been published in final form at https://doi.org/10.1002/ange.201913625. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    Peer-Reviewed
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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.
    URI
    http://hdl.handle.net/10454/17622
    Version
    Accepted manuscript
    Citation
    Cao Q, Crawford DE, Shi C et al (2020) Greener dye synthesis: continuous, solvent-free synthesis of commodity perylene diimides by twin-screw extrusion. Angewandte Chemie International Edition. 132(11): 4508-4513.
    Link to publisher’s version
    https://doi.org/10.1002/ange.201913625
    Type
    Article
    Collections
    Life Sciences Publications

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