Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into Methyl 3-Hydroxypropanoate

doi:10.6023/cjoc201812014

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1450-1455.DOI: 10.6023/cjoc201812014 Previous Articles Next Articles

Notes

丙二酸二甲酯均相催化加氢合成3-羟基丙酸甲酯的研究

方霄龙^a,b, 段宁^a, 章敏^a, 张春燕^b, 刘睿^b, 朱红平^b

a 池州学院化学与材料工程学院池州 247000;
b 厦门大学化学化工学院固体表面物理化学国家重点实验室醇醚酯清洁生产国家工程实验室厦门 361005

收稿日期:2018-12-10 修回日期:2019-01-10 发布日期:2019-01-31
通讯作者: 方霄龙, 朱红平 E-mail:xlfang@stu.xmu.edu.cn;hpzhu@xmu.edu.cn
基金资助:
国家自然科学基金青年基金（No.21802010）、安徽省自然科学基金（No.1808085QB48）及池州学院青年教师科研启动基金（No.2018YJRC001）资助项目.

Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into Methyl 3-Hydroxypropanoate

Fang Xiaolong^a,b, Duan Ning^a, Zhang Min^a, Zhang Chunyan^b, Liu Rui^b, Zhu Hongping^b

a College of Chemistry and Materials Engineering, Chizhou University, Chizhou 247000;
b State Key Laboratory of Physical Chemistry of Solid Surfaces, National Engineering Laboratory for Green Chemical Productions of Alcohols-Ethers-Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005

Received:2018-12-10 Revised:2019-01-10 Published:2019-01-31
Contact: 10.6023/cjoc201812014 E-mail:xlfang@stu.xmu.edu.cn;hpzhu@xmu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation for Young Scientists of China (No. 21802010), the Natural Science Foundation of Anhui Province (No. 1808085QB48), and the Starting Grants for Young Teachers of Chizhou University (No. 2018YJRC001).

1. Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into Methyl 3-Hydroxypropanoate.PDF(562KB)

Abstract

Ruthenium acetylacetonate and aminophosphine ligand were selected as the catalyst system and applied to the catalytic hydrogenation of dimethyl malonate into methyl 3-hydroxypropanoate. With the focus on the catalytic efficiency, the important factors with significant influences on the dimethyl malonate conversion and methyl 3-hydroxypropanoate selectivity were well discussed, including the structure and dosage of the ligand, temperature, reaction time, solvent, and so on. The results revealed that catalyst system of ruthenium acetylacetonate and o-(diphenylphosphino)aniline ligand could obtain significant catalytic results. Under the optimal reaction conditions, this catalyst system can also be applied to catalytic hydrogenation of some other esters with high efficiency.

Key words: ruthenium acetylacetonate, o-(diphenylphosphino)aniline, dimethyl malonate, methyl 3-hydroxypropanoate

Cite this article

Fang Xiaolong, Duan Ning, Zhang Min, Zhang Chunyan, Liu Rui, Zhu Hongping. Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into Methyl 3-Hydroxypropanoate[J]. Chin. J. Org. Chem., 2019, 39(5): 1450-1455.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kraus, G. A. Clean 2008, 36, 648.
[2] Arntz, D.; Wiegand, N. US 5015789, 1991.
[3] (a) Slaugh, L. H.; Weider, P. R. US 5256827, 1993.
(b) Powell, J. B.; Mullin, S. B.; Weider, P. R.; Eubanks, D. C.; Arhancet, J. P. US 5770776, 1998.
[4] (a) Kaur, G.; Srivastava, A. K.; Chand, S. Biochem. Eng. J. 2012, 64, 106.
(b) Lee, C. S.; Aroua, M. K.; Daud, W. M. A. W.; Cognet, P.; Pérès-Lucchese, Y.; Fabre, P. L.; Reynes, O.; Latapie, L. Renewable Sustainable Energy Rev. 2015, 42, 963.
[5] (a) Wang, Y.; Zhou, J.; Guo, X. RSC Adv. 2015, 5, 74611.
(b) Sun, D.; Yamada, Y.; Sato, S.; Ueda, W. Appl. Catal. B Environ. 2016, 193, 75.
[6] (a) Chen, L. F.; Guo, P. J.; Qiao, M. H.; Yan, S. R.; Li, H. X.; Shen, W.; Xu, H. L.; Fan, K. N. J. Catal. 2008, 257, 172.
(b) He, Z.; Lin, H.; He, P.; Yuan, Y. J. Catal. 2011, 277, 54.
(c) Peng, S. Y.; Xu, Z. N.; Chen, Q. S.; Chen, Y. M.; Sun, J.; Wang, Z. Q.; Wang, M. S.; Guo, G. C. Chem. Commun. 2013, 49, 5718.
(d) Ma, X. B.; Chi, H. W.; Yue, H. R.; Zhao, Y. J.; Xu, Y.; Lv, J.; Wang, S. P.; Gong, J. L. AIChE J. 2013, 59, 2530.
[7] (a) Ding, T.; Tian, H.; Liu, J.; Wu, W.; Zhao, B. Catal. Commun. 2016, 74, 10.
(b) Ding, T.; Tian, H.; Liu, J.; Wu, W.; Yu, J. Chin. J. Catal. 2016, 37, 484.
[8] (a) He, L.; Gong, X.; Ye, L.; Duan, X.; Yuan, Y. J. Energy Chem. 2016, 25, 1038.
(b) Yu, J.; Cao, J.; Du, L.; Wei, Y.; Wang, T.; Tian, H. Appl. Catal., A 2018, 555, 161.
[9] (a) Zhao, B. G.; Han, Z. B.; Ding, K. L. Angew. Chem., Int. Ed. 2013, 52, 4744.
(b) Werkmeister, S.; Junge, K.; Beller, M. Org. Process Res. Dev. 2014, 18, 289.
(c) Pritchard, J.; Filonenko, G. A.; van Putten, R.; Hensen, E. J. M.; Pidko, E. A. Chem. Soc. Rev. 2015, 44, 3808.
[10] Li, W.; Xie, J. H.; Yuan, M. L.; Zhou, Q. L. Green Chem. 2014, 16, 4081.
[11] Han, Z.; Rong, L.; Wu, J.; Zhang, L.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 13041.
[12] (a) Tan, X.; Wang, Y.; Liu, Y.; Wang, F.; Shi, L.; Lee, K. H.; Lin, Z.; Lv, H.; Zhang, X. Org. Lett. 2015, 17, 454.
(b) Tan, X.; Wang, Q.; Liu, Y.; Wang, F.; Lv, H.; Zhang, X. Chem. Commun. 2015, 51, 12193.
[13] (a) Fang, X.; Zhang, C.; Chen, J.; Zhu, H.; Yuan, Y. RSC Adv. 2016, 6, 45512.
(b) Fang, X.; Sun, M.; Zheng, J.; Li, B.; Ye, L.; Wang, X.; Cao, Z.; Zhu, H.; Yuan, Y. Sci. Rep. 2017, 7, 3961.
(c) Zhang, Y. W.; Chen, Y. L.; Fang, X. L.; Yuan, Y. Z.; Zhu, H. P. Chin. J. Org. Chem. 2017, 37, 2275(in Chinese). (张亦伟, 陈艺林, 方霄龙, 袁友珠, 朱红平, 有机化学, 2017, 37, 2275.)
[14] Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
[15] Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1997, 667.
[16] Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1998, 1367.
[17] (a) Geilen, F. M. A.; Engendahl, B.; Harwardt, A.; Marquardt, W.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2010, 49, 5510.
(b) Wesselbaum, S.; vom Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2012, 51, 7499.
[18] Saudan, L. A.; Saudan, C. M.; Debieux, C.; Wyss, P. Angew. Chem., Int. Ed. 2007, 46, 7473.
[19] Geilen, F. M. A.; Engendahl, B.; Hölscher, M.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2011, 133, 14349.
[20] (a) Van der Sluys, L. S.; Kubas, G. J.; Caulton, K. G. Organometallics 1991, 10, 1033.
(b) Chen, Y. Z.; Chan, W. C.; Lau, C. P.; Chu, H. S.; Lee, H. L.; Jia, G. Organometallics 1997, 16, 1241.
[21] Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006, 128, 13700.
[22] Mirza, C.; Christian, B.; Bernhard, R.; Wolfgang, A. H.; Fritz, E. K. Angew. Chem., Int. Ed. 2011, 50, 8510.
[23] Ito, M.; Ootsuka, T.; Watari, R.; Shiibashi, A.; Himizu, A.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 4240.
[24] (a) John, J. M.; Takebayashi, S.; Dabral, N.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2013, 135, 8578.
(b) Tan, X.; Wang, Y.; Liu, Y.; Wang, F.; Shi, L.; Lee, K. H.; Lin, Z.; Lv, H.; Zhang, X. Org. Lett. 2015, 17, 454.
[25] (a) Herd, O.; Heßler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69.
(b) Hingst, M.; Tepper, M.; Stelzer, O. Eur. J. Inorg. Chem. 1998, 1998, 73.
(c) Habtemariam, A.; Watchman, B.; Potter, B. S.; Palmer, R.; Parsons, S.; Parkin, A.; Sadler, P. J. J. Chem. Soc., Dalton Trans. 2001, 1306.
(d) Doherty, S.; Knight, J. G.; Scanlan, T. H.; Elsegood, M. R. J.; Clegg, W. J. Organomet. Chem. 2002, 650, 231.
(e) Han, F. B.; Zhang, Y. L.; Sun, X. L.; Li, B. G.; Guo, Y. H.; Tang, Y. Organometallics 2008, 27, 1924.
(f) Richard, V.; Ipouck, M.; Mérel, D. S.; Gaillard, S.; Whitby, R. J.; Witulski, B.; Renaud, J. L. Chem. Commun. 2014, 50, 593.

丙二酸二甲酯均相催化加氢合成3-羟基丙酸甲酯的研究

Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into Methyl 3-Hydroxypropanoate

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 1

Recommended Articles

Metrics

Comments