A novel and efficient procedure for the preparation of benzyl alcohol by hydrolysis of benzyl chloride catalyzed by PEG1000-DAIL[BF4]/Fe2(SO4)3 under homogeneous catalysis in aqueous media

Subject Areas : Journal of the Iranian Chemical Research

Ming Lu ¹ , Hui Jiang ²

1 - College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, PR China
2 - College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, PR China

Received: 2011-10-18 Accepted : 2012-03-27 Published : 2012-09-20

Keywords: Benzyl alcohol, Benzyl chloride, Hydrolysis, Thermoregulated ionic liquid biphasic system,

Abstract :

In this work, benzyl alcohol was obtained in 96% excellent yield by hydrolysis of benzyl chloride catalyzedby the recyclable temperature-dependant phase-separation system that comprised the ionic liquid PEG1000-DAIL[BF4], toluene and ferric sulfate under homogeneous catalysis in aqueous media. This novel methodnot only enhanced the yield, but also made the operating units easy workup. The catalytic system can berecycled or reused without any significant loss of catalytic activity. The mechanism of hydrolysis reactionand the process of catalysis in the thermoregulated ionic liquid bi-phase system were also proposed.

References:

[1] M.D. Zammit, T.P. Davis and G.D. Willett, Inc. J. Polym. Sci. A: Polym. Chem. 35 (1997) 2311-2321.
[2] S. Roy, R. Jung, B.A. Kerwin, W.R. Theodore and F C John, J. Pharm. Sci. 94 (2005) 382-396.
[3] Y. Zhang, S. Roy and L.S Jones, J. Pharm. Sci. 93 (2004) 3076-3089.
[4] J.W. Cho, G.W. Lee and B.C. Chun, J. Appl. Polymr Sci. 62 (1996) 771-778
[5] S.P. and B.K. Mishra, Inc Int. J. Chem. Kinet. 38 (2006) 651-656.
[6] T. Qiu, X.Y. Xu and X.H. Qian, J. Chem. Technol Biotechnol. 84 (2009) 1051-1055.
[7] B.W. Mao, J.F. Wu, M.Y. Hung and Y.Y. Jiang, Polym. Adv. Technol. 13 (2002) 301-304.
[8] D.R. Bryant, J.E. Mckeon and B.C. Ream. J. Org. Chem. 33 (1968) 4123-4127.
[9] M. Periasamy, G.P. Muthukumaragopal and N. Sanjeevakumar, Tetrahedron Lett. 48 (2007), 6966-6969.
[10] A. Sharfi, M.M. Mojtahedi. and M.R. Saidi, Tetrahedron Lett. 40 (1999) 1179-1180.
[11] J.S. Cha and H.C. Brown, J. Org. Chem. 58 (1993) 3974-3979.
[12] G. Kokotos and C.Noula, J. Org. Chem. 61(1996) 6994-6996.
[13] K. S. Ravikumar. and C. Srinivasan, J. Org. Chem. 61(1996) 826-830.
[14] S. Narasimhan, S. Madhavan and K. G. Prasad, J. Org. Chem. 60 (1995) 5314-5315.
[15] H.W. Withers and J. L. Rose, US Pat. (1971) 3557222.
[16] D.S. Mathew and V.G. Gaikar, Ind. Eng. Chem. Res. 44 (2005) 434-441.
[17] H.A. Zahalka and Y. Sasson, J. Mol. Catal. 18 (1983) 51-60.
[18] G.D. Yadav and P.H. Mehta, Catal. Lett. 21 (1993) 391-4031.
[19] R.S. Varma and K. Pitchumani, and K. P. Naicker, Green Chem. 1 (1999) 95-97.
[20] G. Cerichelli, S.Cerritelli, M. Chiarini, and P.D. Maria, Chem. Eur. J. 8 (2002) 5204-5210.
[21] I. Roberts and L.P. Hammett, J. Am. Chem. Soc. 59 (1937) 1063-1070.
[22] G.W. beste and L.P. Hammett, J. Am. Chem. Soc. 62 (1940) 2481-2487.
[23] K. Saramma and R. Anantaraman, P. Math. Sci. 49 (1959) 111-116.
[24] M. Shi and Y.S. Feng, J. Org. Chem. 66 (2001) 3235-3237.
[25] L.G. Menchikov, A.V. Vorogushin, O.S. Korneva and O.M. Nefedov, Mendeleev. Commu. 5(1995)
223-224.
[26] R.N. Gedye, W. Rank and K.C. Westaway, Can. J. Chem. 69 (1991) 706-711.
[27] N.Tanaka, K. Hosoya, K. Iwaguchi and M. Araki, J. Am. Chem. Soc. 106 (1984) 3057-3059.
[28] W.G. Hendrikus and U. H. Brinker, Tetrahedron. 58 (2002) 4963-4967.
[29] H.J. Buysch and U. Jansen, US Pat. (1998), 5750801.
[30] H.J. Buysch and E. Hoffmann, US Pat. (1998) 5728897.
[31] J. L. Kaar, A.M. Jesionowski, J.A. Berberich, R. Moulton and A.J. Russell, J. Am. Chem. Soc. 125
(2003) 4125-4131.
[32] J.Y. Weng, W. Congmin , L. Haoran and Y.W.Green. Chem. 8 (2006) 96-99.
[33] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare and A. Zare, Scientia Iranica Transactions C: Chemistry
and chemical Engineering, 17 (2010) 31-36.
[34] C. Cinzia and P. Daniela, J. Phys. Org. Chem. 18 (2005) 275-297.
[35] A. Kumar and S.S. Pawar, J. Org. Chem. 69 (2004)1419-1420.
[36] A.C. Cole, J.L. Jensen, I. Ntai, K.L. Tran, K.J. Weaver, D.C. Forbes and J.H. Davis, J. Am. Chem. Soc.
124 (2002) 5962-5963.
[37] T. Ooi and K. Maruoka, Angew Chem. Int. Ed. 46 (2007) 4222-4266.
[38] J.A. Gladysz, Chem. Rev. 102 (2002) 3215-3216.
[39] S. Sunitha, S. Kanjilal and R. B. N. Prasad, Tetrahedron Lett. 48 (2007) 6962-6965.
H. Jiang & H. Jiang, J. Iranian Chem. Res. 5 (3) (2012) 129-136
136
[40] Y. Leng, J. Wang, Z. Dunru, R.X. Qian, and L.Shen. Angew Chem. Int. Ed. 48 (2009)168-171
[41] B. Tan, J.Y. Jiang, Y.H.Wang, L. Wei, D.J. Chen and Z. L.Jin, Appl. Organomet. Chem. 22(2008) 620-
623.
[42] H.Z. Zhi , J. Luo. and C.X. Lu, Chem. J. Chin. Univ. 29 (2008) 2007-2010.
[43] H. Z. Zhi, C.X. Lu, Q. Zhang and J. Luo, Chem. Commun. (2009) 2878-2880.
[44] S.J. Zhang and X.M. Lu, Science Press, Beijing, (2006) 149-162.