| dc.description.abstract | The Mitsunobu reaction was published by Japanese chemist Oyo Mitsunobu in 1967, is frequently employed in organic synthesis for forming carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds. It can also invert the configuration of a chiral carbon atom with a hydroxyl group. Due to its mild reaction conditions and ability to replace various functional groups, the Mitsunobu reaction is widely used in modern organic synthesis. Previous literature has often focused on the selection of substrates to synthesize new molecules via the Mitsunobu reaction. However, considering one of the most critical elements of new industrial processes is to help industries reduce pollution at the source, save energy, and lower consumption, thereby bringing economic benefits to enterprises. The by-product of the Mitsunobu reaction contains phosphorus and needs to be recycled. Discarding these by-products indiscriminately can lead to water eutrophication. Additionally, since phosphorus resources on Earth are limited, failing to utilize them will accelerate the depletion of those resources. Initially, we conducted a use test of all the components in the reaction and discovered a new polymorph of triphenylphosphine oxide. Therefore, this study primarily explores the recovery of by-products and the reuse of reactants from the Mitsunobu reaction. We utilized halide salts (calcium bromide) based on previous research to precipitate by-product triphenylphosphine oxide (TPPO), scaling up the process from laboratory scale to a 0.5 liter common stirred tank. The original 18 h process was reduced to 3 h, and concentrations of reactants, products, and by-products were monitored using liquid chromatography, which were then converted to weights to ensure mass balance. Furthermore, the precipitated compounds were cracked with water to recover triphenylphosphine oxide, achieving a 95.7 ± 11.8% yield in just 2 h. The water and calcium bromide were then recovered through vacuum distillation. Overall, this study demonstrates improved processes for large-scale manufacturing, shortened reaction times, energy savings, and the recovery of by-products and reactants. | en_US |