Citation: Nianzhe Li, Yuan Gao, Xinxin Zhang, Zhanjun Yu, Lei Shi, Qi Sun. Oxidation of styrene to benzaldehyde by p-toluenesulfonic acid using hydrogen peroxide in the presence of activated carbon[J]. Chinese Journal of Catalysis, ;2015, 36(5): 721-727. doi: 10.1016/S1872-2067(14)60314-4 shu

Oxidation of styrene to benzaldehyde by p-toluenesulfonic acid using hydrogen peroxide in the presence of activated carbon

1.
Institute of Chemistry for Functionalized Materials, Faculty of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, Liaoning, China

Corresponding author: Qi Sun,
Received Date: 25 December 2014
Available Online: 30 January 2015
Fund Project: 国家自然科学基金(21173110). (21173110)

The selective oxidation of styrene to benzaldehyde catalyzed by p-toluenesulfonic acid (p-TsOH) in the presence of activated carbon (AC) was investigated with H₂O₂ as the oxidant. The reaction parameters of reaction time, temperature, catalyst mass, and styrene/H₂O₂ molar ratios were evaluated. A strong promoting effect of AC on the p-TsOH/H₂O₂ system was observed. The appropriate ratio and amounts of AC and p-TsOH were an important factor. The acidity of p-TsOH does not play a significant role. p-TsOH reacted with H₂O₂ by a non-radical process to oxidize styrene. The function of the AC was to activate H₂O₂and to help the p-TsOH/H₂O₂ system in styrene oxidation. The reduction of oxygen containing groups (-OH, -COOH) on AC by a high temperature treatment or introduction of -SO₃H groups onto AC affected the styrene conversion. The -SO₃H groups were more effective than the oxygen-containing groups on the AC in promoting styrene oxidation.
- Styrene,
- Hydrogen peroxide,
- p-Toluenesulfonic acid,
- Activated carbon,
- Oxidation
1. [1]
  [1] Thao N T, Trung H H. Catal Commun, 2014, 45: 153
2. [2]
  [2] Dhakshinamoorthy A, Primo A, Concepcion P, Alvaro M, Garcia H. Chem Eur J, 2013, 19: 7547
3. [3]
  [3] Nemanashi M, Meijboom R. Catal Lett, 2013, 143: 324
4. [4]
  [4] Sharma S, Sinha S, Chand S. Ind Eng Chem Res, 2012, 51: 8806
5. [5]
  [5] Adam F, Iqbal A. Chem Eng J, 2010, 160: 742
6. [6]
  [6] Patel A, Patel K. Inorg Chim Acta, 2014, 419: 130
7. [7]
  [7] Tong J H, Cai X D, Wang H Y, Zhang Q P. Mater Res Bull, 2014, 55: 205
8. [8]
  [8] Jury F A, Polaert I, Pierella L B, Estel L. Catal Commun, 2014, 46: 6
9. [9]
  [9] Zhuang J Q, Ma D, Yan Z M, Liu X M, Han X W, Bao X H, Zhang Y H, Guo X W, Wang X S. Appl Catal A, 2004, 258: 1
10. [10]
  [10] Saux C, Pierella L B. Appl Catal A, 2011, 400: 117
11. [11]
  [11] Navalon S, Dhakshinamoorthy A, Alvaro M, Garcia H. ChemSusChem, 2011, 4: 1712
12. [12]
  [12] Maggi R, Piscopo C G, Sartori G, Storaro L, Moretti E. Appl Catal A, 2012, 411-412: 146
13. [13]
  [13] Zhang B H, Ren J W, Liu X H, Guo Y, Guo Y L, Lu G Z, Wang Y Q. Catal Commun, 2010, 11: 629
14. [14]
  [14] Saikia L, Satyartthi J K, Srinivas D, Ratnasamy P. J Catal, 2007, 252: 148
15. [15]
  [15] Mo X H, López D E, Suwannakarn K, Liu Y J, Lotero E, Goodwin J G Jr, Lu C Q. J Catal, 2008, 254: 332
16. [16]
  [16] Zhou L P, Dong B B, Tang S, Ma H, Chen C, Yang X M, Xu J. J Energy Chem, 2013, 22: 659
17. [17]
  [17] Usui Y, Sato K, Tanaka M. Angew Chem Int Ed, 2003, 42: 5623
18. [18]
  [18] de Jong M C, Feijt R, Zondervan E, Nijhuis T A, de Haan A B. Appl Catal A, 2009, 365: 141
19. [19]
  [19] Mun S P, Jang J P. J Ind Eng Chem, 2009, 15: 743
20. [20]
  [20] Hassanabadi A. J Chem Res, 2013, 37: 152
21. [21]
  [21] Anuradha V, Srinivas P V, Aparna P, Rao J M. Tetrahedron Lett, 2006, 47: 4933
22. [22]
  [22] Rostami A, Hassanina F, Ghorbani-Choghamarani A, Saadati S. Phosphorus Sulfur Silicon Related Elements, 2013, 188: 833
23. [23]
  [23] Boehm H P. Carbon, 1994, 32: 759
24. [24]
  [24] Ramirez J H, Costa C A, Madeira L M, Mata G, Vicente M A, Rojas-Cervantes M L, López-Peinado A J, Martín-Aranda R M. Appl Catal B, 2007, 71: 44
25. [25]
  [25] Oliveira L C A, Sillva C N, Yoshida M I, Lago R M. Carbon, 2004, 42: 2279
26. [26]
  [26] Santos V P, Pereira M F R, Faria P C C, Órfão J J M. J Hazard Mater, 2009, 162: 736
27. [27]
  [27] Lücking F, Köser H, Jank M, Ritter A. Water Res, 1998, 32: 2607
28. [28]
  [28] Georgi A, Kopinke F D. Appl Catal B, 2005, 58: 9
29. [29]
  [29] Rey A, Zazo J A, Casas J A, Bahamonde A, Rodriguez J J. Appl Catal A, 2011, 402: 146
30. [30]
  [30] Dandekar A, Baker R T K, Vannice M A. Carbon, 1998, 36: 1821
31. [31]
  [31] Shin S, Jang J, Yoon S H, Mochida I. Carbon, 1997, 35: 1739
32. [32]
  [32] Figueiredo J L, Pereira M F R, Freitas M M A, Órfão J J M. Carbon, 1999, 37: 1379
33. [33]
  [33] Khalil L B, Girgis B S, Tawfik T A M. J Chem Technol Biotechnol, 2001,76: 1132
34. [34]
  [34] Ishibashi K, Fujishima A, Watanabe T, Hashimoto K. Elecochem Commun, 2000, 2: 207
35. [35]
  [35] Chang B B, Fu J, Tian Y L, Dong X P. J Phys Chem C, 2013, 117: 6252
36. [36]
  [36] van Vliet M C A, Arends I W C E, Sheldon R A. Synlett, 2001, 2: 248
37. [37]
  [37] Wahlen J, De Vos D E, Jacobs P A. Org Lett, 2003, 5: 1777
38. [38]
  [38] Shaabani A, Rezayan A H. Catal Commun, 2007, 8: 1112
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