BioTeam/ICPEES-ECPM, UMR CNRS 7515, Université de Strasbourg, 25 rue Becquerel, 67087, Strasbourg, Cedex 2, France.
Sci Rep. 2018 Jun 14;8(1):9134. doi: 10.1038/s41598-018-27450-w.
Bis(cyclo-carbonate) was successfully synthesized from D-sorbitol (Sorb-BisCC) through an environmentally friendly process with dimethyl carbonate (DMC) as a reactant. In agreement with green chemistry principles, solvent free reactions were catalyzed and took place at low temperature. The reaction yield was increased until 50%, with the use of 1.3.5-triazabicyclo[4.4.0]dec-5-ene as catalyst and a continuous DMC feed to limit the side-reactions or the loss of reactant by azeotropic flux with a reactional subsidiary product. The obtained Sorb-BisCC is a remarkable platform molecule which could compete with others polycyclic platform molecules (isosorbide). Sorb-BisCC can be e.g., used to synthesize different chemicals such as short and long polyols, or novel biobased non-isocyanate polyurethanes (NIPU). Two Sorb-BisCC molecules have been coupled to obtain novel cyclic diols with pendant side chains. Polyether polyols were also obtained by anionic ring opening polymerization. According to the synthesis conditions, these synthetized polyether polyols range from partially to highly cross-linked materials. Finally, NIPU were synthesized with short and biobased fatty diamines. These different modifications and synthesis highlight the versatility of the Sorb-BisCC and demonstrated its high potential as building block. Sorb-BisCC can be considered as a platform molecule to open the way to different original and biobased chemical architectures.
二（环碳酸酯）通过使用碳酸二甲酯（DMC）作为反应物的环保工艺，从 D-山梨糖醇（Sorb-BisCC）成功合成。根据绿色化学原则，无溶剂反应在低温下进行并进行催化。使用 1.3.5-三氮唑二环[4.4.0]癸-5-烯作为催化剂，并连续进料 DMC 以限制副反应或通过与反应性副产物共沸流损失反应物，从而将反应收率提高至 50%。得到的 Sorb-BisCC 是一种显著的平台分子，可与其他多环平台分子（异山梨醇）竞争。Sorb-BisCC 可用于合成不同的化学品，例如短链和长链多元醇，或新型生物基非异氰酸酯聚氨酯（NIPU）。两个 Sorb-BisCC 分子已耦合以获得具有侧链的新型环状二醇。还通过阴离子开环聚合获得聚醚多元醇。根据合成条件，这些合成的聚醚多元醇从部分交联到高度交联的材料不等。最后，使用短链和生物基脂肪二胺合成了 NIPU。这些不同的修饰和合成突出了 Sorb-BisCC 的多功能性，并展示了其作为构建块的高潜力。Sorb-BisCC 可以被认为是一种平台分子，为不同的原始和生物基化学结构开辟了道路。
