低共熔溶剂氯化胆碱-草酸催化合成乙酰水杨酸
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摘要
以水杨酸和乙酸酐作原料、低共熔溶剂氯化胆碱-草酸作反应介质和催化剂,探讨不同反应条件对乙酰水杨酸合成的影响。研究结果表明,在反应温度75℃、酸酐摩尔比1∶2.5、反应时间40 min、氯化胆碱-草酸用量1.2 g时,乙酰水杨酸的收率可达93%。该催化体系具有价格便宜、制备简单、易回收使用、生物相容性好等优点,符合绿色化工和清洁生产的发展要求,具有广阔的发展前景。
The influence of different reaction conditions on the synthesis of acetylsalicylic acid was discussed,in the presence of salicylic acid and acetic anhydride as raw materials,and the deep eutectic solvent of choline choline-oxalic acid as reaction medium and catalyst. The results show that the yield of acetylsalicylic acid could reach93%,under the conditions of reaction temperature 75 ℃,molar ratio of salicylic acid to acetic anhydride 1∶ 2. 5,reaction time 40 min,amount of choline choline-oxalic acid 1. 2 g. This catalytic system offers some advantages,such as low cost,simple preparation,easy recyclability and good biocompatibility,which meets the development requirements of green chemical industry and clean production,and possesses broad development prospect.
The influence of different reaction conditions on the synthesis of acetylsalicylic acid was discussed,in the presence of salicylic acid and acetic anhydride as raw materials,and the deep eutectic solvent of choline choline-oxalic acid as reaction medium and catalyst. The results show that the yield of acetylsalicylic acid could reach93%,under the conditions of reaction temperature 75 ℃,molar ratio of salicylic acid to acetic anhydride 1∶ 2. 5,reaction time 40 min,amount of choline choline-oxalic acid 1. 2 g. This catalytic system offers some advantages,such as low cost,simple preparation,easy recyclability and good biocompatibility,which meets the development requirements of green chemical industry and clean production,and possesses broad development prospect.
引文
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13严楠,熊云奎,夏剑辉,等.低共熔溶剂中新型螺环吲哚衍生物的绿色合成.有机化学,2015;35(2):384-389Yan Nan,Xiong Yunkui,Xia Jianhui,et al.Green synthesis of novel spirooxindole derivatives in deep eutectic solvent.Chinese Journal of Organic Chemistry,2015;35(2):384-389
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15 Shahcheragh S M,Habibi A,Khosravi S.Straightforward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloridebased deep eutectic solvent.Tetrahedron Letters,2016;58(9):855-859
16 Shaabani A,Hooshmand S E,Afaridoun H.A green chemical approach:a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents.Monatshefte für Chemie-chemical Monthly,2017;148(4):711-716
2李俊.阿司匹林衍生物的设计、合成及其抗肿瘤活性研究.青岛:中国海洋大学,2015Li Jun.The study of design,synthesis and anti-tumor activities of aspirin derivatives.Qingdao:Ocean University of China,2015
3 Zhang Q H,Vigier K D O,Royer S,et al.Deep eutectic solvents:syntheses,properties and applications.Chemical Society Reviews,2012;41(21):7108-7146
4 Smith E L,Abbott A P,Ryder K S.Deep eutectic solvents(DESs)and their applications.Chemical Reviews,2014;114(21):11060-11082
5 Liu P,Hao J W,Mo L P,et al.Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions.RSC Advances,2015;5(60):48675-48704
6熊兴泉,韩骞,石霖,等.低共熔溶剂在绿色有机合成中的应用.有机化学,2016;36(3):480-489Xiong Xingquan,Han Qian,Shi Lin,et al.Application of deep-eutectic solvents in green organic synthesis.Chinese Journal of Organic Chemistry,2016;36(3):480-489
7 Carolin R,Burkhard K.Low melting mixtures in organic synthesis-an alternative to ionic liquids?Green Chemistry,2012;14(11):2969-2982
8王爱玲,郑学良,赵壮志,等.深共融溶剂在有机合成中的应用.化学进展,2014;26(5):784-795Wang Ailing,Zheng Xueliang,Zhao Zhuangzhi,et al.Deep eutectic solvent in green organic synthesis.Progress in Chemistry,2014;26(5):784-795
9 Alonso D A,Baeza A,Chinchilla R,et al.Deep eutectic solvents:the organic reaction medium of the century.European Journal of Organic Chemistry,2016;612-632
10张盈盈,陆小华,冯新,等.胆碱类低共熔溶剂的物性及应用.化学进展,2013;25(6):881-892Zhang Yingying,Lu Xiaohua,Feng Xin,et al.Properties and applications of choline-based deep eutectic solvents.Progress in Chemistry,2013;25(6):881-892
11 Gadilohar B L,Shankarling G S.Choline based ionic liquids and their applications in organic transformation.Journal of Molecular Liquids,2017;227:234-261
12唐利平,赵仕林,罗峰,等.低共熔溶剂中β-吲哚衍生物的绿色合成.精细化工,2015;32(6):704-708Tang Liping,Zhao Shilin,Luo Feng,et al.Green synthesis ofβ-indole derivatives in deep eutectic solvent.Fine Chemicals,2015;32(6):704-708
13严楠,熊云奎,夏剑辉,等.低共熔溶剂中新型螺环吲哚衍生物的绿色合成.有机化学,2015;35(2):384-389Yan Nan,Xiong Yunkui,Xia Jianhui,et al.Green synthesis of novel spirooxindole derivatives in deep eutectic solvent.Chinese Journal of Organic Chemistry,2015;35(2):384-389
14 Kalmode H P,Vadagaonkar K S,Murugan K,et al.Deep eutectic solvent:a simple,environmentally benign reaction media for regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles.RSC Advances,2015;5(44):35166-35174
15 Shahcheragh S M,Habibi A,Khosravi S.Straightforward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloridebased deep eutectic solvent.Tetrahedron Letters,2016;58(9):855-859
16 Shaabani A,Hooshmand S E,Afaridoun H.A green chemical approach:a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents.Monatshefte für Chemie-chemical Monthly,2017;148(4):711-716