Balancing the transesterification reactivity of isosorbide with diphenyl carbonate: preferential activation of exo-OH was written by Zhang, Ming;Tu, Yifei;Zhou, Zibo;Wu, Guozhang. And the article was included in Polymer Chemistry in 2020.Synthetic Route of C13H10O3 The following contents are mentioned in the article:
The exo-hydroxyl group (exo-OH) on isosorbide (ISB) has long been asserted as a highly reactive moiety compared with the endo-hydroxyl group (endo-OH). In this study, calculations based on d. functional theory and experiments without adding catalysts reveal that endo-OH has strong nucleophilic ability, and in the case of transesterification with di-Ph carbonate, the nucleophilic attack surmounts steric hindrance in rendering endo-OH more reactive than exo-OH. The kinetics of transesterification with different catalysts is investigated to determine the catalytic reactivity and mol. structure evolution. The results show that preferential activation of exo-OH moieties can be achieved either by reducing the coordination ability of catalytic cations (lg β1) or by enhancing the alkalinity of catalytic anions. Despite the low reactivity of exo-OH on ISB monomers, terminal exo-OH on carbonate oligomers exhibits higher reactivity than terminal endo-OH, justifying the exptl. fact that ISB-based polycarbonates (ISB-PCs) are mostly terminated by endo-OH. Balancing the reactivity between endo-OH and exo-OH can be promoted by increasing the reaction temperature, thus accelerating transesterification to a high equilibrium constant These findings help to clarify the mechanism of ISB transesterification and provide new strategies for the synthesis of high-mol.-weight ISB-PCs. This study involved multiple reactions and reactants, such as Diphenyl carbonate (cas: 102-09-0Synthetic Route of C13H10O3).
Diphenyl carbonate (cas: 102-09-0) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Synthetic Route of C13H10O3
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics