NOTE

Investigation on Preparation of Methyl Isobutyl Ketone through the Reduction by Isopropanol

  • Xu Lin ,
  • Wang Fang ,
  • Huang Jiejun ,
  • Xu Qing ,
  • Yu Lei ,
  • Fan Yining
Expand
  • a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093;
    b Jiangsu Yangnong Chemical Group Co. Ltd., Yangzhou 225009;
    c School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002;
    d Yangzhou Polytechnology Institute, Yangzhou 225127

Received date: 2016-03-28

  Revised date: 2016-04-20

  Online published: 2016-05-17

Supported by

Project supported by the National Natural Science Fundation of China (No.21202141), the Zhejiang Natural Science Foundation for Distinguished Young Scholars (No.LR14B020002), the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Key Science & Technology Specific Projects of Yangzhou (No.YZ20122029), and the High Level Talent Support Project of Yangzhou University.

Abstract

The production capacity of acetone is excess in China at present. Conversion of acetone into high-value products with huge market demands is of practical value. Methyl isobutyl ketone (MIBK) is an important industrial intermediate with very broad applications and large market requirement. Thus, there are tremendous prospects for industrial applications for the synthesis of MIBK from acetone. This article reports a convenient access to MIBK from acetone through condensation and reduction procedures. Compared with conventional procedures, the method employed isopropanol as an alternative reductant to the dangerous H2 to reduce mesityl oxide (MO) into MIBK. The by-product from the reductant isopropanol was acetone and could be reused as the starting material to produce MO. After conditional optimizations, the MO conversion rate was enhanced to 95.8%, while the selectivity of MIBK was 98.8%. The two steps of reaction could be performed in one-pot.

Cite this article

Xu Lin , Wang Fang , Huang Jiejun , Xu Qing , Yu Lei , Fan Yining . Investigation on Preparation of Methyl Isobutyl Ketone through the Reduction by Isopropanol[J]. Chinese Journal of Organic Chemistry, 2016 , 36(9) : 2232 -2235 . DOI: 10.6023/cjoc201603044

References

[1] Bai, W.-B.; Yu, X.-H.; Ding, W.; Xing, R.-T.; Liu, Y. Chem. Ent. Manage. 2013, (3), 84(in Chinese). (白卫兵, 余咸旱, 丁伟, 杏若婷, 刘源, 化工管理, 2013, (3), 84.)
[2] Liang, C. Techno-Econmics Petrochem. 2004, 20, 35(in Chinese). (梁诚, 石油化工技术经济, 2004, 20, 35.)
[3] (a) Nan, J; Yu, H. B.; Zhang, J. C.; Zhang, Y. T. CN 104355975, 2015[Chem. Abstr. 2015, 162, 352865]. (b) Zhu, R.-H.; Lv, Z.-H.; Ai, F.-B; Liu, X.-S; Song, L.-Z; Su, J. CN 1080564, 1994[Chem. Abstr. 1995, 122, 268628]. (c) Li, W.-H.; Hu, J.-X.; Ma, Y.-G; Zhong, B. CN 1385241, 2002[Chem. Abstr. 2003, 140, 425230].
[4] (a) Yang, S. M.; Wu, Y. M. Appl. Catal. A:Gen. 2000, 192, 211. (b) Unnikrishnan, R.; Narayanan S. J. Mol. Catal. A:Chem. 1999, 144, 173. (c) Chen, Y. Z.; Liaw, B. J.; Tan, H. R.; Shen, K. L. Appl. Catal. A:Gen. 2001, 205, 61. (d) Diaz, Y.; Melo, L.; Mediavilla, M.; Albornoz, A.; Brito, J. L. J. Mol. Catal. A:Chem. 2005, 227, 7. (e) Yang, P.-P.; Shang, Y.-C.; Wang, J.; Yu, J.-F.; Wu, T.-H. React. Kinet. Catal. Lett. 2007, 91, 2, 391. (f) Yang, P.-P.; Yu, J.-F.; Wang, Z.-L.; Xu, M.-P.; Liu, Q.-S.; Yang, X.-W.; Wu, T.-H. Catal. Commun. 2005, 6, 107. (g) Kozhevnikova, E. F.; Kozhevnikov, I. V. J. Catal. 2006, 238, 286.
[5] (a) Deng, S.-C.; Zhuang, K.; Xu, B.-L.; Ding, Y.-H.; Yu, L.; Fan, Y.-N. Catal. Sci. Technol. 2016, 6, 1772. (b) Zhang, X.; Sun, J.-J.; Ding, Y.-H.; Yu, L. Org. Lett. 2015, 17, 5840. (c) Yu, L.; Huang, Y.-P.; Wei, Z.; Ding, Y.-H.; Su, C.-L.; Xu, Q. J. Org. Chem. 2015, 80, 8677. (d) Zhang, X.; Ye, J.-Q.; Yu, L.; Shi, X.-K.; Zhang, M.; Xu, Q.; Lautens, M. Adv. Synth. Catal. 2015, 357, 955. (e) Yu, L.; Li, H.-Y.; Zhang, X.; Ye, J.-Q.; Liu, J.-P.; Xu, Q.; Lautens, M. Org. Lett. 2014, 16, 1346. (f) Yu, L.; Wu, Y.-L.; Cao, H.-E.; Zhang, X.; Shi, X.-K.; Luan, J.; Chen, T.; Pan, Y.; Xu, Q. Green Chem. 2014, 16, 287. (g) Yu, L.; Wang, J.; Cao, H.-E.; Ding, K.-H.; Xu, Q. Chin. J. Org. Chem. 2014, 34, 1986(in Chinese) (俞磊, 王俊, 曹洪恩, 丁克鸿, 徐清, 有机化学, 2014, 34, 1986.) (h) Yu, L.; Wu, Y.-L.; Chen, T.; Pan, Y.; Xu, Q. Org. Lett. 2013, 15, 144. (i) Yu, L.; Wang, J.; Chen, T.; Ding, K-H.; Pan, Y. Chin. J. Org. Chem. 2013, 33, 1096(in Chinese) (俞磊, 王俊, 陈天, 丁克鸿, 潘毅, 有机化学, 2013, 33, 1096.)
[6] Xu, L.; Huang, J.-J.; Liu, Y.-B.; Wang, Y.-N.; Xu, B.-L.; Ding, K.-H.; Ding, Y.-H.; Xu, Q.; Yu, L.; Fan, Y.-N. RSC Adv. 2015, 5, 42178.
[7] (a) Watson, A. J. A.; Williams, J. M. J. Science 2010, 329, 635. (b) Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J. Dalton Trans. 2009, 753. (c) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. (d) Guillena, G.; Ramón, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611. (e) Suzuki, T. Chem. Rev. 2011, 111, 1825. (f) Bähn, S.; Imm, S.; Neubert, L.; Zhang, M.; Neumann, H.; Beller, M. ChemCatChem 2011, 3, 1853.

Outlines

/