A Review on Catalyzed Dimerization of Acrylonitrile

doi:10.6023/cjoc201405004

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 1986-1991.DOI: 10.6023/cjoc201405004 Previous Articles Next Articles

Reviews

丙烯腈催化二聚反应的研究进展

俞磊^a,b,c, 王俊^a, 曹洪恩^a, 丁克鸿^a,b,c, 徐清^a,b,c

a. 江苏省环境材料与环境工程重点实验室扬州大学化学化工学院扬州 225002;
b. 温州大学化学与材料工程学院温州 325035;
c. 江苏扬农化工集团有限公司扬州 225009

收稿日期:2014-05-04 修回日期:2014-05-21 发布日期:2014-06-11
通讯作者: 俞磊 E-mail:yulei@yzu.edu.cn;yzuyulei@163.com
基金资助:
国家自然科学基金（No. 21202141）、江苏省高校优势学科、江苏省环境材料与工程重点实验室开放基金（Nos. K100027，K090030）及贵州大学教育部绿色农药与农业生物工程重点实验室开放基金（No. 2010GDGP0106）资助项目.

A Review on Catalyzed Dimerization of Acrylonitrile

Yu Lei^a,b,c, Wang Jun^a, Cao Hongen^a, Ding Kehong^a,b,c, Xu Qing^a,b,c

a. Jiangsu Key Laboratory of Environmental Material and Environmental Engineering, School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002;
b. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035;
c. Jiangsu Yangnong Chemical Engineering Co. Ltd., Yangzhou 225009

Received:2014-05-04 Revised:2014-05-21 Published:2014-06-11
Supported by:
Project supported by the National Natural Science Fundation of China (No. 21202141), the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Opening Foundation of the Key Laboratory of Environmental Materials and Engineering of Jiangsu Province (Nos. K100027, K090030) and the Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University (No. 2010GDGP0106).

Acrylonitrile (AN) is a cheap and accessible industrial material. Linear dimerization of acrylonitrile affords the skeleton of adiponitrile, which leads to hexamethylene diamine through further hydrogenation. Hexamethylene diamine is an important industrial intermediate with comprehensive applications and wide market requirement and is mainly applied in the synthesis of nylon 66. Therefore, linear dimerization of acrylonitrile is a very important organic reaction. Compared with the electrolytic process which has already been applied in industrial production, the catalyzed dimerization needs low energy consumption and low equipment requirements. Besides, the catalyzed dimerization of acrylonitrile may also afford the branched dimer 2-methyleneglutaronitrile, which is the important intermediate in the synthesis of bromothalonil. Although the market requirement of bromothalonil is not as huge as nylon 66, it is also one of the important chemical industrial products. However, currently, there was no systematic review on AN dimerization. Therefore, this review aims to reorganize and systematically describe the advances of catalyzed dimerization of acrylonitrile for reference of the related technicians in China, including the Ru-catalyzed dimerization, other metal-catalyzed dimerization and phosphorus-catalyzed dimerization.

Key words: acrylonitrile, dimerization, catalysis, adiponitrile, hexamethylene diamine, polymer, nylon 66, bromothalonil

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Yu Lei, Wang Jun, Cao Hongen, Ding Kehong, Xu Qing. A Review on Catalyzed Dimerization of Acrylonitrile[J]. Chin. J. Org. Chem., 2014, 34(10): 1986-1991.

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References

[1] Chem. Word 1963, 458 (in Chinese).
(化学世界, 1963, 458.)
[2] Ciganek, E. Org. React. 1997, 51, 340.
[3] http://www.mining120.com/show/1312/ 20131220_130710.html
[4] Misono, A.; Uchida, Y.; Hidai, M.; Kanai, H. Chem. Commun. 1967, 357.
[5] Dewhirst, K. C. Inorg. Chem. 1966, 5, 319.
[6] Massey, A. G. J. Inorg. Nuclear Chem. 1962, 24, 1172.
[7] Misono, A.; Uchida, Y.; Hidai, M. Bull. Chem. Soc. Jpn. 1968, 41, 396.
[8] Misono, A.; Uchida, Y.; Hidai, M.; Inomata, I. Chem. Commun. 1968, 704.
[9] McClure, J. D.; Owyang, R.; Slaugh, L. H. J. Organomet. Chem. 1968, 12, P8.
[10] Hallman, P. S.; Evans, D.; Osborn, J. A.; Wilkinson, G. Chem. Commun. 1967, 305
[11] Tsou, D. T.; Burrington, J. D.; Maher, E. A.; Grasselli, R. K. J. Mol. Catal. 1983, 22, 29.
[12] As shown in Scheme 2, one of the H atom on the methylene came from hydrogen.
[13] Tsou, D. T.; Burrington, J. D.; Maher, E. A.; Grasselli, R. K. J. Mol. Catal. 1985, 30, 219.
[14] Fukuoka, A.; Nagano, T.; Furuta, S.; Yoshizawa, M.; Hirano, M.; Komiya, S. Bull. Chem. Soc. Jpn. 1998, 71, 1409.
[15] Kashiwagi, K.; Sugise, R.; Shimakawa, T.; Matuura, T.; Shirai, M.; Kakiuchi, F.; Murai, S. Organometallics 1997, 16, 2233.
[16] Kashiwagi, K.; Sugise, R.; Shimakawa, T.; Matuura, T.; Shirai, M. Chem. Lett. 2006, 35, 186.
[17] Kashiwagi, K.; Sugise, R.; Shimakawa, T.; Matuura, T. Chem. Lett. 2007, 36, 1384
[18] Kashiwagi, K.; Sugise, R.; Shimakawa, T.; Matuura, T.; Shirai, M. J. Mol. Catal. A: Chem. 2007, 264, 9.
[19] Kashiwagi, K.; Sugise, R.; Shimakawa, T.; Matuura, T.; Shirai, M. J. Mol. Catal. A: Chem. 2008, 286, 120.
[20] (a) Komiya, S.; Fukuoka, A.; Hirano, M. JP 09286769, 1997 [Chem. Abstr. 1997, 128, 3449].
(b) Suzuki, Y.; Kiso, Y. JP 9504307, 1997 [Chem. Abstr. 1997, 126, 157193].
(c) Murai, S.; Oodan, K.; Sugise, R.; Shirai, M.; Shimakawa, T. JP 06009531, 1994 [Chem. Abstr. 1994, 120, 191146].
[21] Sugise, R.; Shirai, M.; Shimakawa, T.; Kashiwagi, K. JP 05286918, 1993 [Chem. Abstr. 1994, 120, 54210].
[22] Angès, G.; Chiusoli, G. P.; Cometti, G. Chem. Commun. 1968, 1515.
[23] Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. Bull. Chem. Soc. Jpn. 1970, 43, 877.
[24] Watanabe, Y.; Takeda, M. Bull. Chem. Soc. Jpn. 1973, 46, 883.
[25] Nomura, K.; Ishino, M. J. Mol. Catal. 1992, 73, L15.
[26] For reviews see: (a) Xie, P.-Z.; Huang, Y. Eur. J. Org. Chem. 2013, 6213.
(b) Xu, S.-L.; He, Z.-J. RSC Adv. 2013, 3, 16885.
(c) Wang, Y.-R.; Pan, J.-J.; Chen, Z.-D.; Sun, X.-Q.; Wang, Z.-M. Mini-Rev. Med. Chem. 2013, 13, 836.
(d) Wang, Z.-M.; Kwon, O. In Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology, Ed.: Trabocchi, A., Wiley-VCH, Hoboken, 2013, p. 97.
(e) Xu, S.-L.; He, Z.-J. Chin. J. Org. Chem. 2012, 32, 1159 (in Chinese).
(徐四龙, 贺峥杰, 有机化学, 2012, 32, 1159.)
(f) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035.
[27] Selected recent articles: (a) Zheng, S.-Q.; Lu, X.-Y. Org. Lett. 2008, 10, 4481.
(b) Lu, Z.; Zheng, S.-Q.; Zhang, X.-M.; Lu, X.-Y. Org. Lett. 2008, 10, 3267.
(c) Tian, J.-J.; Zhou, R.; Sun, H.-Y.; Song, H.-B.; He, Z.-J. J. Org. Chem. 2011, 76, 2374.
(d) Zhou, R.; Wang, J.-F.; Song, H.-B.; He, Z.-J. Org. Lett. 2011, 13, 580.
(e) Cruz, D.; Wang, Z.-M.; Kibbie, J.; Modlin, R.; Kwon, O. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6769.
(f) Wang, Z.-M.; Castellano, S.; Kinderman, S. S.; Argueta, C. E.; Beshir, A. B.; Fenteany, G.; Kwon, O. Chem. Eur. J. 2011, 17, 649.
(g) Zhou, R.; Wang, J.-F.; Duan, C.; He, Z.-J. Org. Lett. 2012, 14, 6134.
(h) Zhou, R.; Wang, J.-F.; Tian, J.-J.; He, Z.-J. Org. Bioorg. Chem. 2012, 10, 773.
(i) Zheng, J.; Huang, Y.; Li, Z.-M. Org. Lett. 2013, 15, 5064.
(j) Hu, C.-C.; Zhang, Q.-L.; Huang, Y. Chem. Asian J. 2013, 8, 1981.
(k) Li, E.-Q.; Huang, Y.; Liang, L.; Xie, P.-Z. Org. Lett. 2013, 15, 3138.
(l) Zhou, R.; Wang, J.-F.; Yu, J.; He, Z.-J. J. Org. Chem. 2013, 78, 10596.
(m) Tian, J.-J.; He, Z.-J. Chem. Commun. 2013, 49, 2058.
[28] (a) McClure, J. D. J. Org. Chem. 1970, 35, 3045.
(b) McClure, J. D. US 3225083, 1965 [Chem. Abstr. 1966, 64, 103655].
[29] Jennings, J. R.; Cozens, R. J. Appl. Catal. A: Gen. 1995, 124, 297.
[30] Jennings, J. R.; Cozens, R. J.; Wade, K. Appl. Catal. A: Gen. 1995, 130, 175.
[31] Jennings, J. R.; Cozens, R. J. Appl. Catal. A: Gen. 1996, 135, 163.
[32] Yu, L.; Wang, J.; Zhang, X.; Cao, H.-E.; Wang, G.-L.; Ding, K.-H.; Xu, Q.; Lautens, M. RSC Adv. 2014, 4, 19122. (a) Charardes, P.; Grard, C.; Lafont P.; Thiers, M. FR 1366081, 1964 [Chem. Abstr. 1964, 61, 83787].
(b) Baizer, M. M.; Anderson, J. D. J. Org. Chem. 1965, 30, 1357.
(c) Jenner, G. Tetrahedron Lett. 2000, 41, 3091.
(d) Araki, Y.; Maki, T. JP 05001008, 1993 [Chem. Abstr. 1993, 118, 212465].
(e) Araki, Y.; Maki, T. JP 04368362, 1992 [Chem. Abstr. 1993, 118, 254412].
(f) Saito, M. JP 2012001521, 2012 [Chem. Abstr. 2012, 156, 122960].
(g) Ichikawa, S.; Iwane, H. JP 11180941, 1999 [Chem. Abstr. 1999, 131, 58603].
(h) Heckle, W. A., Mathews Ⅲ, M. J.; Peoples, P. R. US 4952541, 1990 [Chem. Abstr. 1990, 113, 172961].

丙烯腈催化二聚反应的研究进展

A Review on Catalyzed Dimerization of Acrylonitrile

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