Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization

doi:10.1016/S1004-9541(14)60048-3

Chinese Journal of Chemical Engineering ›› 2014, Vol. 22 ›› Issue (3): 312-317.DOI: 10.1016/S1004-9541(14)60048-3

• 催化、动力学与反应工程 • 上一篇下一篇

Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization

程欲晓¹, 周宇艳¹, 张继东¹, 费旭东¹, 马腾洲¹, 梁学正²

1 Inspection Center of Industrial Products and Raw Materials, Shanghai Entry-Exit Inspection and Quarantine Bureau, Shanghai 200135, China;
2 Institute of Applied Chemistry, Shaoxing University, Shaoxing 312000, China

收稿日期:2012-05-27 修回日期:2013-03-14 出版日期:2014-03-28 发布日期:2014-03-05
通讯作者: LIANG Xuezheng
基金资助:
Supported by the Chinese National General Administration of Quality Supervision, Inspection and Quarantine (2012IK048, 2011IK041) and the National Natural Science Foundation of China (21103111).

Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization

CHENG Yuxiao¹, ZHOU Yuyan¹, ZHANG Jidong¹, FEI Xudong¹, MA Tengzhou¹, LIANG Xuezheng²

1 Inspection Center of Industrial Products and Raw Materials, Shanghai Entry-Exit Inspection and Quarantine Bureau, Shanghai 200135, China;
2 Institute of Applied Chemistry, Shaoxing University, Shaoxing 312000, China

Received:2012-05-27 Revised:2013-03-14 Online:2014-03-28 Published:2014-03-05
Contact: LIANG Xuezheng
Supported by:
Supported by the Chinese National General Administration of Quality Supervision, Inspection and Quarantine (2012IK048, 2011IK041) and the National Natural Science Foundation of China (21103111).

摘要/Abstract

摘要： The novel solid acid with both sulfonic and carbonyl acid groups has been synthesized from 3-((2-sulfoethoxy) carbonyl)acrylic acid and tetraethyl orthosilicate (TEOS). The catalytic activities were investigated through the acetalization. The results showed that the novel solid acid was very efficient for the reactions with the high yields. The high acidity, high stability and reusability were the key feature of the novel solid acid. Moreover, the sulfonic and carbonyl acid groups could cooperate during the catalytic process, which improved its catalytic activities. The catalyst shows recyclability, and hold great potential for replacement of homogeneous catalysts.

关键词: solid acid with sulfonic and carbonyl acid groups, acetalization, green chemistry

Abstract: The novel solid acid with both sulfonic and carbonyl acid groups has been synthesized from 3-((2-sulfoethoxy) carbonyl)acrylic acid and tetraethyl orthosilicate (TEOS). The catalytic activities were investigated through the acetalization. The results showed that the novel solid acid was very efficient for the reactions with the high yields. The high acidity, high stability and reusability were the key feature of the novel solid acid. Moreover, the sulfonic and carbonyl acid groups could cooperate during the catalytic process, which improved its catalytic activities. The catalyst shows recyclability, and hold great potential for replacement of homogeneous catalysts.

Key words: solid acid with sulfonic and carbonyl acid groups, acetalization, green chemistry

程欲晓, 周宇艳, 张继东, 费旭东, 马腾洲, 梁学正. Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization[J]. Chinese Journal of Chemical Engineering, 2014, 22(3): 312-317.

CHENG Yuxiao, ZHOU Yuyan, ZHANG Jidong, FEI Xudong, MA Tengzhou, LIANG Xuezheng. Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization[J]. Chin.J.Chem.Eng., 2014, 22(3): 312-317.

参考文献

1 Anastas, P.T., Kirchhoff, M.M., "Origins, current status, and future challenges of green chemistry", Acc. Chem. Res., 35, 686-694 (2002).

2 Anastas, P.T., Zimmermann, J.B., "Design through the 12 principles of green engineering", Environ. Sci. Technol., 37, 94A-101A (2003).

3 Clark, J.H., "Solid acids for green chemistry", Acc. Chem. Res., 35, 791-797 (2002).

4 Shu, Q., Gao, J., Liao, Y., Wang, J., "Reaction kinetics of biodiesel synthesis from waste oil using a carbon-based solid acid catalyst", Chin. J. Chem. Eng., 19, 163-168 (2011).

5 Misono, M., Acad, C.R., "Heterogeneous catalysis", Sci. Ser. Iic., 3, 471-475 (2000).

6 Okuhara, T., "Water-tolerant solid acid catalysts", Chem. Rev., 102, 3641-3666 (2002).

7 Hara, M., Yoshida, T., Takagaki, A., Takata, T., Kondo, J.N., Hayashi, S., Domen, K., "A carbon material as a strong protonic acid", Angew. Chem. Int. Ed., 43, 2955-2958 (2004).

8 Toda, M., Takagaki, A., Okamura, M., Kondo, J.N., Hayashi S., Domen, K., Hara, M., "Green chemistry: Biodiesel made with sugar catalyst", Nature, 438 (7065), 178 (2005).

9 Okamura, M., Takagaki, A., Toda, M., Kondo, J.N., Domen, K., Tatsumi, T., Hare, M., Hayashi S., "Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon", Chem. Mater., 18, 3039-3045 (2006).

10 Nakajima, K., Okamura, M., Kondo, J.N., Domen, K., Tatsumi, T., Hayashi, S., Hara, M., "Amorphous carbon bearing sulfonic acid groups in mesoporous silica as a selective catalyst", Chem. Mater., 21, 186-193 (2009).

11 Xia, Y., Mokaya, R., "On the hydrothermal stability of mesoporous aluminosilicate MCM-48 materials", J. Phys. Chem. B, 107, 6954-6960 (2003).

12 Li, C., "Chiral synthesis on catalysts immobilized in microporous and mesoporous materials", Catal. Rev., 46, 419-492 (2004).

13 Wang, Y.J., Caruso, F., "Mesoporous silica spheres as supports for enzyme immobilization and encapsulation", Chem. Mater., 17, 953-961 (2005).

14 Riego, J.M., Sedin, Z., Zaldívar, J.M., Marziano, N.C., Tortato, C., "Sulfuric acid on silica-gel: An inexpensive catalyst for aromatic nitration", Tetrahedron Lett., 37, 513-516 (1996).

15 Shaabani, A., Rahmati, A., "Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles", J. Mol. Catal. A Chem., 249, 246-248 (2006).

16 Izumi, Y., Hisano, K., Hida, T., "Acid catalysis of silica-included heteropolyacid in polar reaction media", Appl. Catal. A Gen., 181, 277-282 (1999).

17 Khadilkar, B.M., Borkar, S.D., "Synthesis of benzophenones using silica-gel supported Lewis acid catalyst", Tetrahedron Lett., 38, 1641-1642 (1997).

18 Shaterian, H. R., Shahrekipoor, F., Ghashang, M., "Silica supported perchloric acid (HClO₄-SiO₂): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions", J. Mol. Catal. A Chem., 272, 142-151 (2007).

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Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization

Synthesis of a Novel Solid Acid with both Sulfonic and Carbonyl Acid Groups and Its Catalytic Activities in Acetalization

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