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    • 2. 发明申请
    • SYNTHESIS OF DIACIDS, DIALDEHYDES, OR DIAMINES FROM THF-DIOLS
    • 从THF-DIOLS合成DIA,DIALDEHYDES或DIAMINES
    • WO2015057365A2
    • 2015-04-23
    • PCT/US2014057399
    • 2014-09-25
    • ARCHER DANIELS MIDLAND CO
    • STENSRUD KENNETH
    • C07D307/14
    • C07D307/16C07D307/12C07D307/14
    • A simple and elegant chemical process for the synthesis of oxygenated products, such as acids and aldehydes, or other derivative products, such as amines and nitriles, of cyclic bifunctional molecules made from renewable, bio-based sources such as HMF and/or its reduction product, 2,5-bis(hydroxymethyl)-tetrahydrofuran (bHMTHF) is described. In general, the process involves: a) generating a tetrahydrofuran-2,5-diyl-bis(methylene)-bis(sulfonate) from bHMTHFs using a sulfonate; b) displacing nucleophilically at least a sulfonate leaving group from the tetrahydrofuran-2,5-diyl-bis(methylene)-bis(sulfonate) to form a THF-dinitrile; and either c) oxidizing the THF-dinitrile with an acid having a pKa of ≤ 0 to generate a di-acid, or d) reducing partially the THF-dinitrile to generate a di-aldehyde, or e) reducing fully the THF-dinitrile to generate a di-amine.
    • 用于合成氧化产物(例如酸和醛)或其它衍生产物(例如胺和腈)的由可再生生物基源(例如HMF和/或其还原)制备的环状双功能分子的简单而优雅的化学方法 产物,2,5-双(羟甲基) - 四氢呋喃(bHMTHF)。 通常,该方法包括:a)使用磺酸盐从bHMTHF生成四氢呋喃-2,5-二基 - 双(亚甲基) - 双(磺酸酯); b)从四氢呋喃-2,5-二基 - 双(亚甲基) - 双(磺酸酯)中至少亲核取代磺酸酯离去基团以形成THF-二腈; 和c)用pKa≤0的酸氧化THF-二腈以产生二酸,或d)部分地还原THF-二腈以产生二醛,或e)完全还原THF-二腈 以产生二胺。