Hydration of DCPD over sulfonic acid-functionalized SBA-15 catalyst

Yu-Cheng Lin; Yu-Wei Huang; Ku-Hsiang Sung; Tsung-Han Lin; Soofin Cheng

Journal of Industrial and Engineering Chemistry, Vol.44, 60-66, December, 2016

DOI10.1016/j.jiec.2016.08.013 Export Citation

Hydration of DCPD over sulfonic acid-functionalized SBA-15 catalyst

Yu-Cheng Lin, Yu-Wei Huang, Ku-Hsiang Sung¹, Tsung-Han Lin, and Soofin Cheng^†

Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan, ROC
¹Chemical Systems Research Division, National Chung-Shan Institute of Science and Technology, Taoyuan 32599, Taiwan, ROC

E-mail:

Sulfonic acid-functionalized SBA-15 materials (SA-SBA-15) with ordered channeling pores were synthesized by one-pot co-condensation and used to catalyze the hydration of dicyclopentadiene (DCPD). The target product, cydecanol (DCPD-OH) has been used as a modifier for polyester or alkyd resin. Propylsulfonic acid functionalized SBA-15 was found to be more efficient than the silica gel counterpart or arylsulfonic acid functionalized material in catalyzing DCPD hydration to yield DCPD-OH.The DCPD conversion and DCPD-OH yield increased with the decrease in H2O/DCPD ratio. Optimal DCPD conversion and DCPD-OH selectivity were obtained with the molar composition of DCPD:H2O:H+-catalyst = 1:30:0.1.

Keywords:DCPD;Hydration;Solid catalyst;Mesoporous materials;Sulfonic acid;SBA-15

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[2] Moffett RB, Org. Synth. Coll., 4, 238 (1962)

[3] Bruson HA, Riener TW, J. Am. Chem. Soc., 67, 723 (1945)

[4] Kasei H, Jpn. Patent Kokai 55-19205, 56-59723.

[5] Talwalkar S, Kumbhar P, Mahajani S, Catal. Commun., 7, 717 (2006)

[6] Okazaki S, Harada H, Chem. Lett., 17, 1313 (1988)

[7] Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS, Nature, 359, 710 (1992)

[8] Fang X, Frywell GE, Wang LQ, Kim AY, Liu J, Kemner KM, Science, 276, 923 (2007)

[9] Sun JM, Zhang H, Tian RJ, Ma D, Bao XH, Su DS, Zou HF, Chem. Commun., 1322 (2006)

[10] Corma A, Chem. Rev., 97, 237 (1997)

[11] Chen SY, Lee JF, Cheng S, J. Catal., 270(1), 196 (2010)

[12] Chen SY, Tang CY, Lee JF, Jang LY, Tatsumi T, Cheng S, J. Mater. Chem., 21, 2255 (2011)

[13] Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)

[14] Berube F, Nohair B, Kleitz F, Kaliaguine S, Chem. Mater., 22, 1988 (2010)

[15] Wroblewska A, Makuch E, Sokalska E, Malko M, React. Kinet. Mech. Catal., 113, 519 (2014)

[16] Wroblewska A, Molecules, 19, 19907 (2014)

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[18] Wroblewska A, Makuch E, React. Kinet. Mech. Catal., 105, 451 (2012)

[19] Kulawik K, Schulz-Ekloff G, Rathousky J, Zukal A, Had J, Collect. Czech. Chem. Commun., 60, 451 (1995)

[20] Lee GD, Kim SG, Jeong HH, Park SS, Hong SS, Solid State Phenom., 124-126, 1793 (2007)

[21] Yang L, Jiang Z, Lai S, Jiang C, Zhong H, Int. J. Chem. Eng., Article ID 691562, 7 pp. (2014)

[22] Wroblewska A, Makuch E, Pol. J. Chem. Technol., 4(15), 111 (2013)

[23] Wroblewska A, Makuch E, J. Adv. Oxid. Technol., 17(1), 44 (2014)

[24] Chen SY, Yokoi T, Tang CY, Jang LY, Tatsumi T, Chan JCC, Cheng S, Green Chem., 13, 2920 (2011)

[25] Wang XG, Lin KSK, Chan JCC, Cheng SF, J. Phys. Chem. B, 109(5), 1763 (2005)

[26] Cheng S, Wang X, Chen SY, Top. Catal., 52, 681 (2009)

[27] Walcarius A, Delacote C, Chem. Mater., 15, 4181 (2003)

[28] Macquarrie DJ, Jackson DB, Chem. Commun., 1781 (1997)

[29] Nakato T, Toyoshi Y, Kimura M, Okuhara T, Catal. Today, 52(1), 23 (1999)

[30] Chen CC, Cheng S, Jang LY, Microporous Mesoporous Mater., 109, 258 (2008)