文献类型：期刊文献

英文题名：Resolution of trans-1,2-cyclohexanedicarboxylic acid containing two carboxylic groups by forming diastereomeric salts based on feeding molar ratio control

作者：Xin, Xiaoyu[1];Zhou, Junjie[1];He, Quan[2];Peng, Yangfeng[1,3];Wei, Yongming[1,3];Zhao, Hongliang[1];Tong, Tianzhong[1]

机构：[1]East China Univ Sci & Technol, Sch Chem Engn, Shanghai, Peoples R China;[2]Dalhousie Univ, Fac Agr, Dept Engn, Truro, NS, Canada;[3]East China Univ Sci & Technol, Sch Chem Engn, China 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2024

卷号：36

期号：2

外文期刊名：CHIRALITY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001115023500001)】；

基金：The authors are thankful for the financial support provided by the National Natural Science Foundation of China (21978082).

语种：英文

外文关键词：crystal structure; diastereomeric salts; phenylethylamine; stoichiometric ratios; trans-1,2-cyclohexane dicarboxylic acid

摘要：To investigate the thermodynamic and molecular self-assembly mechanism of trans-1,2-cyclohexane dicarboxylic acid containing two carboxylic acid groups in the chiral resolution process, (S)-phenylethylamine was used as the chiral resolving agent. Two stoichiometric salts were formed when the raw materials were fed at different molar ratios: cyclohexane dicarboxylate monophenylethylamine salt and cyclohexane dicarboxylate diphenylethylamine salt. When the molar ratio of the (S)-phenylethylamine to trans-1,2-cyclohexane dicarboxylic acid was less than 3:1, trans-(1S,2S)-cyclohexane dicarboxylic acid was obtained with 97 e.e% purity. But when the molar ratio exceeded 3:1, the product was the racemic trans-(1,2)-cyclohexane dicarboxylic acid. In addition, single crystal structures of more soluble mono-salt, less soluble mono-salt, and less soluble di-salt were obtained. The weak intermolecular interactions and the way of the molecules packing in the crystals were analyzed. The hydrogen bond was stronger in the less soluble salt than that in the more soluble salt. And a "lock-and-key" structure in the hydrophobic layers makes it more tightly packed through the van der Waals interaction, which is responsible for the stability of less soluble salts.