| 武 琦1，赵 漫1，刘梅香1，邓淑蕾1，张双龙1，刘 铭2，石建军1*.邻苯二甲酸二烷基酯的高选择性单水解[J].海南师范大学学报自科版,2021,34(2):159-165 |
| 邻苯二甲酸二烷基酯的高选择性单水解 |
| Highly Selective Monohydrolysis of Dialkyl Phthalates |
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| DOI：10.12051/j.issn.1674-4942.2021.02.007 |
| 中文关键词: 邻苯二甲酸二烷基酯 半酯 单水解 共溶剂 |
| 英文关键词: dialkyl phthalates half ester monohydrolysis co-solvent |
| 基金项目:海南省高等学校科学研究项目（Hnky2019-33）；海南省科协青年科技英才学术创新计划项目（QCXM201925） |
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| 中文摘要: |
| 半酯是有机化学中合成各种化合物的重要原料之一，二酯的选择性单水解对于制备半
酯的研究具有重要意义。本研究选择了DMSO、THF和CH3CN作为共溶剂体系，在碱溶液中对邻苯
二甲酸二烷基酯进行了高选择性的单水解反应，并讨论了不同的共溶剂、碱及其用量对水解反应的
影响。结果表明DMSO对水解反应的选择性和反应活性最好，水解反应在40 min完成，半酯产率为
94%；采用KOH、LiOH、NaOH、CsOH四种不同的碱溶液进行水解反应，KOH的效果最好。由于酯基
疏水性对单水解影响显著，因此探讨了不同共溶剂体系下邻苯二甲酸二酯衍生物疏水性对单水解
的影响。研究表明，低浓度共溶剂条件下疏水性增强的对称二酯活性显著下降，通过提高共溶剂比
例，选择性水解得到了极大的改善。对比THF和CH3CN，DMSO对水解反应的促进最为明显，能够
缩短反应时间，提高反应活性，高产率地制备半酯。本研究结果为有机合成半酯提供了重要依据。 |
| 英文摘要: |
| Half ester is one of the important ingredients for the synthesis of various compounds in organic chemistry, the
selective monohydrolysis of diesters is of great significance to the study of the preparation of half ester. A highly selective
monohydrolysis reaction in the alkali solution was studied using DMSO, THF and CH3CN as co-solvent, and the effect of
different co-solvent, different bases and their dosage on hydrolysis reaction were discussed. The results showed that the se⁃
lectivity and reactivity of DMSO to the hydrolysis reaction were the best, the monohydrolysis was completed whitin 40 min,
and the yield of half ester was 94%. Monohydrolysis in four different alkali solutions (including LiOH, NaOH, CsOH and
KOH) was explored, and KOH solution had the best results. The hydrophobicity of ester group had significant effect on
monohydrolysis, therefore the influence of the hydrophobicity of phthalate diester derivatives on monohydrolysis under dif⁃
ferent co-solvent systems was discussed. The results showed that the activity of the diester with enhanced hydrophobicity
was significantly reduced under low concentration of co-solvent. By increasing the co-solvent ratio, the selective hydrolysis
has been greatly improved. Comparing with THF and CH3CN, DMSO promotes the hydrolysis reaction most obviously. High
concentration of DMSO can shorten the reaction time and increase the reactivity to prepare half ester with high yields. This
study provides an important basis for organic synthesis of half ester. |
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