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

doi:10.6023/cjoc201603044

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2232-2235.DOI: 10.6023/cjoc201603044 Previous Articles Next Articles

NOTE

异丙醇还原法制备甲基异丁基酮的研究

徐林^a,b,c, 王芳^d, 黄杰军^b, 徐清^b,c, 俞磊^a,b,c, 范以宁^a

a 南京大学化学化工学院南京 210093;
b 江苏扬农化工集团有限公司扬州 225009;
c 扬州大学化学化工学院扬州 225002;
d 扬州工业职业技术学院扬州 225127

收稿日期:2016-03-28 修回日期:2016-04-20 发布日期:2016-05-17
通讯作者: 俞磊, 范以宁 E-mail:yulei@yzu.edu.cn;ynfan@nju.edu.cn
基金资助:
国家自然科学基金（No.21202141）、浙江省自然科学杰出青年基金（No.LR14B020002）、江苏省高校优势学科项目、扬州市自然科学基金重大科技专项（No.YZ20122029）、扬州大学高端人才支持计划资助项目.

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

Xu Lin^a,b,c, Wang Fang^d, Huang Jiejun^b, Xu Qing^b,c, Yu Lei^a,b,c, Fan Yining^a

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:2016-03-28 Revised:2016-04-20 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.

1. Investigation on Preparation of Methyl Isobutyl Ketone through the Reduction by Isopropanol.PDF(354KB)

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.

Key words: Acetone, mesityl oxide (MO), catalysis, reduction, methyl isobutyl ketone (MIBK)

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]. Chin. J. Org. Chem., 2016, 36(9): 2232-2235.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[3]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[4]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[5]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[6]	Jing Huang, Yihua Yang, Zhanhui Zhang, Shouxin Liu. Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 409-420.
[7]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[8]	Yang Li, Yanan Dong, Yuehui Li. Efficient Synthesis of Nitrile Compounds through Amide Conversion via N-Boroamide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 638-643.
[9]	Sida Li, Xin Cui, Xing-Zhong Shu, Lipeng Wu. Titanium-Catalyzed Synthesis of 1,1-Diborylalkanes from Aryl Alkenes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 631-637.
[10]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[11]	Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu. Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 195-203.
[12]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[13]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[14]	Yanshuo Zhu, Hongyan Wang, Penghua Shu, Ke'na Zhang, Qilin Wang. Recent Advances on Alkoxy Radicals-Mediated C(sp³)—H Bond Functionalization via 1,5-Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 1-17.
[15]	Xianqiang Meng, Yi Yang, Wanjie Liang, Jingtao Wang, Rongkui Zhang, Hui Liu. Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 224-231.

异丙醇还原法制备甲基异丁基酮的研究

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

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments