脱羧
化学
甲酰胺类
氨基酸
催化作用
有机化学
胺气处理
产量(工程)
生物化学
冶金
材料科学
作者
Laurens Claes,Michiel H. A. Janssen,Dirk De Vos
出处
期刊:Chemcatchem
[Wiley]
日期:2019-07-29
卷期号:11 (17): 4297-4306
被引量:23
标识
DOI:10.1002/cctc.201900800
摘要
Abstract Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio‐based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal‐free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO 2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2‐propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N ‐formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one‐pot catalytic system.
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