4.8 Article

Catalytic Amination of Polylactic Acid to Alanine

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 40, Pages 16358-16363

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c08159

Keywords

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Funding

  1. Natural Science Foundation of China [21725301, 22072002, 21932002, 21821004]
  2. National Key R&D Program of China [2017YFB0602200]
  3. Key Research Program of Nanjing IPE Institute of Green Manufacturing Industry
  4. Beijing Outstanding Young Scientist Program [BJJWZYJH01201914430039]
  5. Tencent Foundation through the XPLORER PRIZE

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A one-pot catalytic method has been demonstrated to convert polylactic acid into alanine using a Ru/TiO2 catalyst and ammonia solution treatment. The process achieves a 77% yield of alanine at 140 degrees C with an overall selectivity of 94% through recycling experiments.
In comparison to the traditional petroleum-based plastics, polylactic acid, the most popular biodegradable plastic, can be decomposed into carbon dioxide and water in the environment. However, the natural degradation of polylactic acid requires a substantial period of time and, more importantly, it is a carbon-emitting process. Therefore, it is highly desirable to develop a novel transformation process that can upcycle the plastic trash into value-added products, especially with high chemical selectivity. Here we demonstrate a one-pot catalytic method to convert polylactic acid into alanine by a simple ammonia solution treatment using a Ru/TiO2 catalyst. The process has a 77% yield of alanine at 140 degrees C, and an overall selectivity of 94% can be reached by recycling experiments. Importantly, no added hydrogen is used in this process. It has been verified that lactamide and ammonium lactate are the initial intermediates and that the dehydrogenation of ammonium lactate initiates the amination, while Ru nanoparticles are essential for the dehydrogenation/rehydrogenation and amination steps. The process demonstrated here could expand the application of polylactic acid waste and inspire new upcycling strategies for different plastic wastes.

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