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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 04: 794 - 798

DOI: https://doi.org/10.6023/cjoc1109212

Notes

Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride

  • Dong Jianxun ,
  • Yan Zhifeng ,
  • Shi Yukun ,
  • Hu Xiaojing ,
  • Ding Zhenzhen ,
  • Zhao Weiling ,
  • Song Juanjuan ,
  • Huang Weiping
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  • a College of Chemistry, Nankai University, Tianjin 300071;
    b Henan Weihua Safety Assessment Company Limited, Zhengzhou 450000

Received date: 2011-09-21

  Revised date: 2011-11-12

  Online published: 2012-04-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 21071086).

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Abstract

The isomerization of 3-chloro-1-butene to crotyl chloride was carried out in the homogeneous catalytic system containing cuprous salt and dimethylformamide. Factors such as solvent, temperature, and content of catalyst that influence the reaction were investigated. The type of solvent and content of catalyst had great effect on the isomerization. Equilibrium constant of the title reaction reached 3.88, which was kept for 5 h at 60 ℃ under the optimal condition. The process of isomerization was monitored with in-situ FTIR-ATR and the possible reaction mechanism was suggested in this paper.

Key words： 3-chloro-1-butene; crotyl chloride; cuprous chloride; isomerization

Cite this article

Dong Jianxun , Yan Zhifeng , Shi Yukun , Hu Xiaojing , Ding Zhenzhen , Zhao Weiling , Song Juanjuan , Huang Weiping . Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 794 -798 . DOI: 10.6023/cjoc1109212

References

[1] Xu, K.-X. Handbook of Organic Chemical Materials and Intermediates, Liaoning Petrochemical Engineering Technical Information Master Station, Shenyang, 1989, p. 60 (in Chinese). (徐克勋, 有机化工原料及中间体便览, 辽宁省石油化工技术情 报总站, 沈阳, 1989, p. 60.)  

[2] Kharasch, M. S.; Margolis, E. T.; Mayo, F. R. J. Org. Chem. 1936, 1, 393.  

[3] Mascavage, L. M.; Dalton, D. R. Tetrahedron Lett. 1991, 32, 3461.  

[4] DeWolfe, R. H.; Young, W. G. Chem. Rev. 1956, 56, 753.  

[5] Hemmingson, J. A. J. Chem. Soc. B 1971, 1347.

[6] Dittmer, D. C.; Marcantonio, A. F. J. Org. Chem. 1964, 29, 3473.  

[7] Winstein, S.; Young, W. G. J. Am. Chem. Soc. 1936, 58, 104.  

[8] Kharasch, M. S.; Kritchevsky, J.; Mayo, F. R. J. Org. Chem. 1937, 2, 489.  

[9] Lane, J. F.; Fentress, J.; Sherwood Jr, L. T. J. Am. Chem. Soc. 1944, 66, 545.  

[10] Yang, L.; Houser, R. P. Inorg. Chem. 2006, 45, 9416.  

[11] Chadha, S.; Nelson, W. H.; Emrich, R.; Lindesmith, E. Appl. Spectrosc. 1993, 47, 475.  

[12] Lu, M.; Wang, S.-W.; Li, J. J. Nanjing Univ. Sci. Technol. 2007, 31, 533 (in Chinese). (陆明, 汪水旺, 李剑, 南京理工大学学报, 2007, 31, 533.)

[13] Braude, E. A. Quart. Rev. 1950, 4, 419.

[14] Young, W. G.; Winstein, S.; Goering, H. L. J. Am. Chem. Soc. 1951, 73, 1958.  

[15] Puentes, E.; Mamalis, I.; Noels, A. F. J. Catal. 1983, 82, 365.  

[16] Mamalis, I.; Grandjean, J.; Noels, A. F. Catal. Today 1987, 1, 59.  

[17] Cristol, S. J.; Lee, G. A. J. Am. Chem. Soc. 1969, 91, 7554.  

[18] Schei, S. H.; Klaeboe, P. Acta Chem. Scand. A 1983, 37, 315.

[19] Schei, S. H. J. Mol. Struct. 1984, 118, 319.  

[20] Crowder, G. A.; Smyrl, N. J. Mol. Struct. 1971, 10, 373.  

[21] Klemperer, W.; Rice, S. A.; Berry, R. S. J. Am. Chem. Soc. 1957, 79, 1810.  
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