Abstract
Aldol condensation of methyl propionate (MP) and formaldehyde (FA) is a green and sustainable route to synthesize methyl methacrylate (MMA). In this work, lanthanum and cesium-loaded SBA-15 acid–base bifunctional catalysts for aldol condensation have been prepared by wetness impregnation method to maximize the yield of MMA. With the investigation of the relationship between the properties of catalysts and the catalytic performance, the appropriate acid–base sites for this reaction were provided. The results showed that La existed as LaONO3 on the catalysts and could constitute additional Lewis acid sites on the catalysts. The Cs-0.1La/SBA-15 (with La content of 0.1 %) exhibited higher catalytic activity than the other La-containing catalysts because of the higher density of medium base sites and medium acid sites. The catalysts calcined at 450 °C performed well on this reaction due to the formation of medium base sites on the catalysts as well as the big surface area around 400 m2/g and uniform pore size at 6 nm. When the MP/FA molar ratio was 1/1, the conversion of MP was 29.2 % and the selectivity of MMA could reach 90.4 %.
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Nagai K (2001) Appl Catal A 221:367–377
Nagai K, Ui T (2004) Sumitomo Chem 2:4–13
Spivey JJ, Gogate MR, Zoeller JR, Colberg RD (1997) Ind Eng chem Res 36:4600–4608
Kanno M, Yasukawa T, Ninomiya W, Ooyachi K, Kamiya Y (2010) J Catal 273:1–8
Langpape M, Millet JMM (2000) Appl Catal A 200:89–101
Brückner A, Scholz G, Heidemann D, Schneider M, Herein D, Bentrup U, Kant M (2007) J Catal 245:369–380
Mestl G, Ilkenhans T, Spielbauer D, Dieterle M, Timpe O, Kröhnert J, Jentoft F, Knözinger H, Schlögl R (2001) Appl Catal A 210:13–34
Zhou LL, Wang L, Zhang SJ, Yan RY, Diao YY (2015) J Catal 319:431–440
Ai M (1990) Bull Chem Soc Jpn 63:3722–3724
Ai M (2005) Appl Catal A 288:211–215
Li B, Yan RY, Wang L, Diao YY, Li ZX, Zhang SJ (2013) Catal Lett 143:829–838
Li B, Yan RY, Wang L, Diao YY, Li ZX, Zhang SJ (2014) Ind Eng Chem Res 53:1386–1394
Gogate MR, Spivey JJ, Zoeller JR (1997) Catal Today 36:243–254
Loghmani MH, Shojaei AF (2015) Int J Hydrogen Energy 40:6573–6581
Shu YY, Travert A, Schiller R, Ziebarth M, Wormsbecher R, Cheng WC (2015) Top Catal 58:334–342
Zhang G, Hattori H, Tanabe K (1988) Appl Catal 36:189–197
Chan KS, Ma J, Jaenicke S, Chuah GK, Lee JY (1994) Appl Catal A 107:201–227
Song KS, Kang SK, Kim SD (1997) Cattl Lett 45:65–68
Sfeir J, Buffat PA, Möckli P, Xanthopoulos N, Vasquez R, Mathieu HJ, Van Herle J, Thampi KR (2001) J Catal 202:229–244
Avert PV, Weckhuysen BM (2004) Phys Chem Chem Phys 6:52–56
Bhargav KK, Ram S, Labhsetwar N, Majumder SB (2015) Sensor Actuat B 206:389–398
Nakamura T, Petzow G, Gauckler LJ (1979) Mater Res Bull 14:649–659
Zwinkels MFM, Järås SG, Menon PG, Griffin TA (1993) Catal Rev 35:319–358
Kumar P, Srivastava VC, Mishra IM (2015) Catal Commun 60:27–31
Nguyen TTN, Ruaux V, Massin L, Lorentz C, Afanasiev P, Maugé F, Bellière-Baca V, Rey P, Millet JMM (2015) Appl Catal B 166–167:432–444
Zhao DY, Huo QS, Feng J, Chmelka BF, Stucky GD (1998) J Am Chem Soc 120:6024–6036
Russbueldt BM, Hoelderich WF (2010) J Catal 271:290–304
Karppinen M, Kyläkoski P, Niinistö L, Rodellas C (1989) J Therm Anal 35:347–353
Wang Y, Zhang GF, Li CS, Yan G, Lu YF (2011) Bull Mater Sci 34:1379–1383
Nicholson KT, Zhang KZ, Banaszak Holl MM (1999) J Am Chem Soc 121:3232–3233
Maileanu M, Crisan M, Petrache C, Crisan D, Jitianu A, Predoi D, Kuncser V, Filoti G (2005) J Phys 50:595–606
Gadzhiev AZ, Gafurov MM, Kirillov SA (1980) J Appl Spectrosc 33:1343–1346
Gobichon AE, Auffrédic JP, Louër D (1996) Solid State Ion 93:51–64
Chen H, Xue MW, Hu SH, Shen JY (2012) Chem Eng J 181–182:677–684
Hu SH, Xue MW, Chen H, Shen JY (2010) Chem Eng J 162:371–379
Meloni D, Sini MF, Cutrufello MG, Monaci R, Rombi E, Ferino I (2013) J Therm Anal Calorim 112:489–498
Gao J, Hou ZY, Guo JZ, Zhu YH, Zheng XM (2008) Catal Today 131:278–284
Acknowledgments
This work was financially supported by National Natural Science Foundation of China (NO. 21406244, 21276267), the Key Program of National Science Foundation of China (NO. 91434203) and the Key Laboratory of Applied Surface and Colloid Chemistry of Shaanxi Normal University.
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Wang, Y., Yan, R., Lv, Z. et al. Lanthanum and Cesium-Loaded SBA-15 Catalysts for MMA Synthesis by Aldol Condensation of Methyl Propionate and Formaldehyde. Catal Lett 146, 1808–1818 (2016). https://doi.org/10.1007/s10562-016-1810-x
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DOI: https://doi.org/10.1007/s10562-016-1810-x