Skip to content
Publicly Available Published by De Gruyter November 5, 2011

Hydrogenation of methyl laurate to produce lauryl alcohol over Cu/ZnO/Al2O3 with methanol as the solvent and hydrogen source

  • Shuguang Liang , Huizhen Liu , Jinli Liu , Weitao Wang , Tao Jiang , Zhaofu Zhang and Buxing Han

Hydrogenation of methyl laurate was conducted over a Cu/ZnO/Al2O3 catalyst, using methanol as the solvent and hydrogen source, to give lauryl alcohol. In this process, the solvent underwent partial decomposition in contact with the catalyst to generate hydrogen, which served as the hydrogenation agent. The effect of different factors on the reaction was examined, to optimize production of lauryl alcohol with high conversion efficiency and selectivity. Use of methanol as the solvent not only favored the reaction, but also suppressed a side reaction involving transesterification between methyl laurate and lauryl alcohol. Under optimal reaction conditions, 91.8 % conversion of methyl laurate and 88.8 % yield of lauryl alcohol could be achieved.


1 10.1016/S1872-2067(08)60050-9, M. H. Looi, S. T. Lee, S. B. Abd-hamid. Chin. J. Catal.29, 566 (2008).Search in Google Scholar

2 M. Myers. Surfactant Science and Technology, John Wiley, New York (2006).10.1002/047174607XSearch in Google Scholar

3 G. C. Gervajio. Bailey’s Industrial Oil and Fat Products, John Wiley, New York (2005).Search in Google Scholar

4 10.1007/BF02678792, U. R. Kreutzer. J. Am. Oil Chem. Soc.61, 343 (1984).Search in Google Scholar

5 10.1007/BF02678794, T. Voeste, H. Buchold. J. Am. Oil Chem. Soc.61, 350 (1984).Search in Google Scholar

6 H. Buchold. Chem. Eng.90, 42 (1983).Search in Google Scholar

7 10.1007/BF02671350, E. C. Leonard. J. Am. Oil Chem. Soc.60, 1160 (1983).Search in Google Scholar

8 R. Tsushima. Inform8, 362 (1997).Search in Google Scholar

9 D. S. Brands, E. K. Peols, A. Bliek. Appl. Catal., A184, 279 (1999).Search in Google Scholar

10 10.1021/ja01354a042, H. Adkins, K. Folkers. J. Am. Chem. Soc.53, 1095 (1931).Search in Google Scholar

11 10.1080/01614949408013931, T. Turek, D. L. Trimm, N. W. Cant. Catal. Rev.—Sci. Eng.36, 645 (1994).Search in Google Scholar

12 10.1007/s11746-997-0088-y, R. D. Rieke, D. S. Thakur, B. D. Roberts, G. T. White. J. Am. Oil Chem. Soc.74, 333 (1997).Search in Google Scholar

13 10.1007/s11746-997-0089-x, R. D. Rieke, D. S. Thakur, B. D. Roberts, G. T. White. J. Am. Oil Chem. Soc.74, 341 (1997).Search in Google Scholar

14 10.1016/S1872-2067(09)60087-5, P. Yuan, Z. Y. Liu, W. Q. Zhang, H. J. Sun, S. C. Liu. Chin. J. Catal.31, 769 (2010).Search in Google Scholar

15 F. T. van der Scheur, L. H. Staal. Appl. Catal., A108, 63 (1994).10.1016/0926-860X(94)85181-6Search in Google Scholar

16 10.1007/s11814-009-0267-7, H. Huang, G. Cao, C. Fan, S. Wang, S. Wang. Korean J. Chem. Eng.26, 1574 (2009).Search in Google Scholar

17 10.1007/s10562-009-0247-x, H. Huang, S. Wang, S. Wang, G. Cao. Catal. Lett.134, 351 (2010).Search in Google Scholar

18 10.1007/BF00807616, D. S. Brands, E. K. Poels, T. A. Krieger, O. V. Makarova, C. Weber, S. Veer, A. Bliek. Catal. Lett.36, 175 (1996).Search in Google Scholar

19 10.1007/s11746-000-0202-6, Y. Hattori, K. Yamamoto, J. Kaita, M. Matsuda, S. Yamada. J. Am. Oil Chem. Soc.77, 1283 (2000).Search in Google Scholar

20 10.1023/A:1019010600765, Y. Z. Chen, C. L. Chang. Catal. Lett.48, 101 (1997).Search in Google Scholar

21 D. S. Brands, E. K. Poels, A. Bliek. Appl. Catal., A184, 279 (1999).Search in Google Scholar

22 A. H. Sijpkes, N. van der Puil, P. J. van der Brink, H. S. B. Abdul, H. J. F. der K. Adrianus. U.S. Patent 20070207921 (2007).Search in Google Scholar

23 10.1016/0021-9517(90)90227-B, V. M. Deshpande, K. Ramnarayan, C. S. Narasimhan. J. Catal.121, 174 (1990).Search in Google Scholar

24 Y. Pouilloux, A. Piccirilli, J. Barrault. J. Mol. Catal., A108, 161 (1996).10.1016/1381-1169(96)00010-6Search in Google Scholar

25 10.1006/jcat.1998.2044, Y. Pouilloux, F. Autin, C. Guimon, J. Barrault. J. Catal.176, 215 (1998).Search in Google Scholar

26 M. Toda, S. Tanaka, S. Niwa, F. Mizukami, Z. Koppany, L. Guczi, K.-Y. Cheah, T.-S. Tang. Appl. Catal. A: Gen.189, 243 (1999).Search in Google Scholar

27 Y. Hara, K. Endou. Appl. Catal., A239, 181 (2003).10.1016/S0926-860X(02)00388-5Search in Google Scholar

28 T. Miyake, T. Makino, S. Taniguchi, H. Watanuki, T. Niki, S. Shimizu, Y. Kojima, M. Sano. Appl. Catal., A364, 108 (2009).10.1016/j.apcata.2009.05.036Search in Google Scholar

29 G. H. Graaf, E. J. Stamhuis, A. Beenackers. Chem. Eng. Sci.43, 3185 (1988).Search in Google Scholar

30 10.1023/A:1023555415577, A. Y. Rozovskii, G. I. Lin. Top Catal.22, 137 (2003).Search in Google Scholar

31 10.1016/S0920-5861(00)00503-4, J. P. Lange. Catal. Today64, 3 (1999).Search in Google Scholar

32 10.1021/ie020979s, X. M. Liu, G. Q. Lu, Z. F. Yan, J. Beltramini. Ind. Eng. Chem. Res.42, 6518 (2003).Search in Google Scholar

33 10.1016/j.jcat.2008.07.004, C. Baltes, S. Vukojevi, F. Schüth. J. Catal.258, 334 (2008).Search in Google Scholar

34 10.1016/S0021-9517(03)00221-5, J. Agrell, H. Birgersson, M. Boutonnet, I. Melian-Cabrera, R. M. Navarro, J. L. G. Fierro. J. Catal.219, 389 (2003).Search in Google Scholar

35 10.1016/S0920-5861(02)00235-3, J. P. Shen, C. Song. Catal. Today77, 89 (2002).Search in Google Scholar

36 10.1021/ja0706302, K. M. K. Yu, C. M. Y. Yeung, S. C. Tsang. J. Am. Chem. Soc.129, 6360 (2007).Search in Google Scholar PubMed

37 10.1039/c0cc00751j, J. L. Liu, C. K. Guo, Z. F. Zhang, T. Jiang, H. Z. Liu, J. L. Song, H. L. Fan, B. X. Han. Chem. Commun. 5770 (2010).Search in Google Scholar PubMed

38 D. Zhang, H. Yin, C. Ge, J. Xue, T. Jiang, L. Yu, Y. Shen. J. Ind. Eng. Chem.15, 537 (2009).Search in Google Scholar

39 10.1007/s10562-007-9366-4, D. Zhang, H. Yin, R. Zhang, J. Xue, T. Jiang. Catal. Lett.122, 176 (2008).Search in Google Scholar

40 10.1016/j.catcom.2006.06.009, T. Hu, H. Yin, R. Zhang, H. Wu, T. Jiang, Y. J. Wada. Catal. Commun.8, 193 (2007).Search in Google Scholar

41 10.1016/j.catcom.2004.06.005, J. Yang, H. Zheng, Y. Zhu, G. Zhao, C. Zhang, B. Teng, H. Xiang, Y. Li. Catal. Commun.5, 505 (2004).Search in Google Scholar

42 10.1039/b109658n, Y. L. Zhu, H. W. Xiang, G. Wu, L. Bai, Y. W. Li. Chem. Commun. 254 (2002).Search in Google Scholar

43 10.1007/s11746-999-0151-y, S. van den Hark, M. Härröd, P. Moller. J. Am. Oil Chem. Soc.76, 1363 (1999).Search in Google Scholar

44 S. van den Hark, M. Härröd. Appl. Catal., A210, 207 (2001).10.1016/S0926-860X(00)00826-7Search in Google Scholar

45 10.1039/b003039m, M. B. O. Andersson, J. W. King, L. G. Blomberg. Green Chem.2, 230 (2000).Search in Google Scholar

46 10.1007/s11746-002-0438-1, D. S. Brands, E. K. Poels, A. C. Dimian, A. Bliek. J. Am. Oil Chem. Soc.79, 75 (2002).Search in Google Scholar

47 10.1016/S0196-8904(02)00234-0, A. Demirbas. Energy Convers. Mgmt.44, 2093 (2003).Search in Google Scholar

48 10.1016/S0016-2361(00)00083-1, S. Saka, K. Dadan. Fuel80, 225 (2001).Search in Google Scholar

49 10.1016/S0016-2361(00)00140-X, D. Kusdiana, S. Saka. Fuel80, 693 (2001).Search in Google Scholar

50 10.1016/S0196-8904(01)00170-4, A. Demirbas. Energy Convers. Mgmt.43, 2349 (2002).Search in Google Scholar

51 10.1016/S0960-8524(03)00201-3, D. Kusdiana, S. Saka. Bioresour. Technol.91, 289 (2004).Search in Google Scholar

52 10.1016/S0960-8524(03)00202-5, Y. Warabi, D. Kusdiana, S. Saka. Bioresour. Technol.91, 283 (2004).Search in Google Scholar

53 A. F. M. Barton. Handbook of Solubility and Other Cohesion Parameters, CRC Press, Florida (1985).Search in Google Scholar

54 10.1016/j.fluid.2007.01.034, Y. Shimoyama, Y. Iwai, B. S. Jin, T. Hirayama, Y. Arai. Fluid Phase Equilibr.257, 217 (2007).Search in Google Scholar

55 10.1126/science.1179713, H. Z. Liu, T. Jiang, B. X. Han, S. G. Liang, Y. X. Zhou. Science326, 1250 (2009).Search in Google Scholar PubMed

Online erschienen: 2011-11-5
Erschienen im Druck: 2011-11-5

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 22.9.2023 from
Scroll to top button