Synthesis, characterization of triphenyltin grafted on SBA-15 mesoporous silica and its catalytic performance for the synthesis of 4-methylacetophenone

doi:10.1016/j.cjche.2013.12.001

›› 2015, Vol. 23 ›› Issue (2): 384-388.DOI: 10.1016/j.cjche.2013.12.001

• 催化、动力学与反应工程 • 上一篇下一篇

Synthesis, characterization of triphenyltin grafted on SBA-15 mesoporous silica and its catalytic performance for the synthesis of 4-methylacetophenone

Qigang Deng, Zhile Qin, Ying Yang, Weiming Song

College of Chemistry and Chemical Engineering of Qiqihar University, Qiqihar 161000, China

收稿日期:2013-03-21 修回日期:2013-12-16 出版日期:2015-02-28 发布日期:2015-03-01
通讯作者: Qigang Deng
基金资助:
Supported by the National Science Foundation of Heilongjiang Province (B201010) and the Education Department of Heilongjiang Province (12511595).

Synthesis, characterization of triphenyltin grafted on SBA-15 mesoporous silica and its catalytic performance for the synthesis of 4-methylacetophenone

Qigang Deng, Zhile Qin, Ying Yang, Weiming Song

College of Chemistry and Chemical Engineering of Qiqihar University, Qiqihar 161000, China

Received:2013-03-21 Revised:2013-12-16 Online:2015-02-28 Published:2015-03-01
Supported by:
Supported by the National Science Foundation of Heilongjiang Province (B201010) and the Education Department of Heilongjiang Province (12511595).

摘要/Abstract

摘要： The production of Ph₃Sn-O-SBA-15 (Ph₃SnSBA) was achieved by heating triphenyltin chloride and SBA-15 in N-methylpyrrolidone at 190℃ for 5 h using triethylamine as a catalyst. The composition, structure, and surface physical and chemical properties of Ph₃SnSBA were characterized using inductively coupled plasma-atomic emission spectroscopy (ICP-AES), ¹³C, ¹¹⁹Sn and ²⁹Si solid-state nuclear magnetic resonance (NMR) spectroscopy in situ pyridine infrared spectroscopy (Py-IR), N₂ adsorption-desorption isotherms, X-ray diffraction (XRD) and transmission electron microscopy (TEM). The results of ICP-AES and organic elemental analysis showed that the grafting yield of Sn was 17% (by mass) for Ph₃SnSBA. The elemental analysis and solid-state NMR results for Ph₃SnSBA were consistent with grafting of triphenyltin on SBA-15. The N₂ adsorption-desorption, XRD and TEM analyses showed that Ph₃SnSBA retained an ordered hexagonal mesoporous structure, resulting in decreases in the surface area, pore size and mesopore volume, and an increase in acidity as compared with SBA-15. The Hammett acidity function (H₀) value and the number of acid sites for Ph₃SnSBA, obtained by the Hammett methods, were 2.77-3.30 and 2.07 mmol·g^-1, respectively. The Friedel-Crafts acylation of toluene and acetic anhydride over Ph₃SnSBA was investigated. The yield of methylacetophenone (MAP) and the selectivity for 4-methylacetophenone (PMAP) were 79.56% and 97.12%, respectively, when the conditions were n(toluene):n(anhydride)=2.0:1.0 with 6% (by mass) catalyst, and heating under reflux for 5 h. The PMAP selectivity still reached 93.11% when Ph₃SnSBA was used for the fifth time under the same reaction conditions.

关键词: SBA-15, Triphenyltin chloride, Grafting reaction, Catalysis, Friedel-Crafts

Abstract: The production of Ph₃Sn-O-SBA-15 (Ph₃SnSBA) was achieved by heating triphenyltin chloride and SBA-15 in N-methylpyrrolidone at 190℃ for 5 h using triethylamine as a catalyst. The composition, structure, and surface physical and chemical properties of Ph₃SnSBA were characterized using inductively coupled plasma-atomic emission spectroscopy (ICP-AES), ¹³C, ¹¹⁹Sn and ²⁹Si solid-state nuclear magnetic resonance (NMR) spectroscopy in situ pyridine infrared spectroscopy (Py-IR), N₂ adsorption-desorption isotherms, X-ray diffraction (XRD) and transmission electron microscopy (TEM). The results of ICP-AES and organic elemental analysis showed that the grafting yield of Sn was 17% (by mass) for Ph₃SnSBA. The elemental analysis and solid-state NMR results for Ph₃SnSBA were consistent with grafting of triphenyltin on SBA-15. The N₂ adsorption-desorption, XRD and TEM analyses showed that Ph₃SnSBA retained an ordered hexagonal mesoporous structure, resulting in decreases in the surface area, pore size and mesopore volume, and an increase in acidity as compared with SBA-15. The Hammett acidity function (H₀) value and the number of acid sites for Ph₃SnSBA, obtained by the Hammett methods, were 2.77-3.30 and 2.07 mmol·g^-1, respectively. The Friedel-Crafts acylation of toluene and acetic anhydride over Ph₃SnSBA was investigated. The yield of methylacetophenone (MAP) and the selectivity for 4-methylacetophenone (PMAP) were 79.56% and 97.12%, respectively, when the conditions were n(toluene):n(anhydride)=2.0:1.0 with 6% (by mass) catalyst, and heating under reflux for 5 h. The PMAP selectivity still reached 93.11% when Ph₃SnSBA was used for the fifth time under the same reaction conditions.

Key words: SBA-15, Triphenyltin chloride, Grafting reaction, Catalysis, Friedel-Crafts

Qigang Deng, Zhile Qin, Ying Yang, Weiming Song. Synthesis, characterization of triphenyltin grafted on SBA-15 mesoporous silica and its catalytic performance for the synthesis of 4-methylacetophenone[J]. , 2015, 23(2): 384-388.

参考文献

[1] V.A. Grinberg, A.A. Pasynskii, T.L. Kulova, N.A.Maiorova, A.M. Skundin, O.A. Khazova, C.G. Law, Tolerant-to-methanol cathodic electrocatalysts based on organometallic clusters, Russ. J. Electrochem. 44 (2) (2008) 202-213.
[2] M. Abrantes, M.S. Balula, A.A. Valente, F.A.A. Paz, M. Pillinger, C.C. Romão, J. Rocha, I.S. Goncalves, Structural and catalytic studies of a trimethyltin vanadate coordination polymer, J. Inorg. Organomet. Polym. Mater. 17 (1) (2007) 215-222.
[3] S. Baus, A. Mizar, T.S.B. Baul, E. Rivarola, ¹¹⁹Sn Mössbauer characterization of self assembled organotin(IV) complexes with Schiff bases containing amino acetate skeletons, Hyperfine Interact. 185 (2008) 95-102.
[4] N.P. Bharathi, M. Alam, A. TasleemJan, A.A. Hashmi, Bioactive organotin materials: synthesis, characterization and antimicrobial investigation, J. Inorg. Organomet. Polym. 19 (2009) 187-195.
[5] F. Lefebvre, P. Putaj, J.M. Basset, X.X. Wang, X.Z. Fu, Modification of the adsorption and catalytic properties of micro- and mesoporous materials by reactions with organometallic complexes, Sci. China B 53 (9) (2010) 1862-1869.
[6] X.X.Wang, X. Chen, Z.X. Fu, Preparation and properties of surface butyltin of mesoporous molecular sieves, Chin. J. Inorg. Chem. 18 (5) (2002) 465-468 (in Chinese).
[7] R.L. Wu, M.L. Deng, B. Kong, X.Z. Yang, Coarse-grained molecular dynamics simulation of ammonium surfactant self-assemblies: Micelles and vesicles, J. Phys. Chem. B 113 (45) (2009) 15010-15016.
[8] K.S. Yeung, M.E. Farkas, Z. Qiu, Friedel-Crafts acylation of indoles in acidic imidazolium chloroaluminate ionic liquid at room temperature, Tetrahedron Lett. 43 (8) (2002) 5793-5795.
[9] R.A. Wolf, Process research on the preparation of 1-(3-trimethylsilylphenyl)-2,2,2- trifluoroethanone by a Friedel-Crafts acylation reaction, Org. Process Res. Dev. 12 (1) (2008) 23-29.
[10] D.Y. Zhao, Q.S. Huo, J.L. Feng, B.F. Chmelka, G.D. Stucky, Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures, J. Am. Chem. Soc. 120 (24) (1998) 6024-6036.
[11] W.M. Song, X. Liu, T. Jing, Q.G. Deng, Characterization and catalytic properties of Al- MCM-41 mesoporous materials by reactions with tributyltin chloride, Chin. J. Chem. Eng. 20 (5) (2012) 900-905.
[12] Y. Kitayama, H. Asano, T. Kodama, J. Abe, Synthesis of Sn-incorporated folded sheets mesoporous materials (Sn-FSM-16), J. Porous. Mater. 5 (1998) 139-146.
[13] B.B. Fan, J.L. Zhang, R.F. Li, W.B. Fan, In situ preparation of functional heterogeneous organotin catalyst tethered on SBA-15, Catal. Lett. 121 (11) (2008) 297-302.
[14] H.A. Declercq, T.L. Gorski, E.H. Schacht, M.C. Cornelissen, Osteoblast behaviour on in situ photopolymerizable three-dimensional scaffolds based on D, L-lactide and ε-caprolactone: influence of pore volume, pore size and pore shape, J. Mater. Sci. Mater. Med. 19 (2008) 3105-3114.
[15] S. Selvakumar, A.P. Singh, Benzoylation of anisole over silicotungstic acid modified mesoporous alumina, Catal. Lett. 128 (11) (2009) 363-372.
[16] L. Chmielarz, P. Kus'trowski,M. Drozdek, M. Rutkowska, R. Dziembaj,M.Michalik, P. Cool, E.F. Vansant, SBA-15 mesoporous silica modified with rhodium by MDD method and its catalytic role for N₂O decomposition reaction, J. Porous. Mater. 18 (6) (2011) 483-491.
[17] R. Bosque, J. Sales, A QSPR study of the p solute polarity parameter to estimate retention in HPLC, J. Chem. Inf. Comput. Sci. 43 (4) (2003) 1240-1247.

Synthesis, characterization of triphenyltin grafted on SBA-15 mesoporous silica and its catalytic performance for the synthesis of 4-methylacetophenone

Synthesis, characterization of triphenyltin grafted on SBA-15 mesoporous silica and its catalytic performance for the synthesis of 4-methylacetophenone

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Baoyu Liu, Feng Xiong, Jianwen Zhang, Manna Wang, Yi Huang, Yanxiong Fang, Jinxiang Dong. Enhanced ortho-selective t–butylation of phenol over sulfonic acid functionalized mesopore MTW zeolites[J]. 中国化学工程学报, 2023, 60(8): 1-7.
[2]	Fei Li, Xuemei Wang, Pengze Zhang, Qinqin Wang, Mingyuan Zhu, Bin Dai. Nitrogen and phosphorus co-doped activated carbon induces high density Cu⁺ active center for acetylene hydrochlorination[J]. 中国化学工程学报, 2023, 59(7): 193-199.
[3]	Tingjun Fu, Ran Wang, Kun Ren, Liangliang Zhang, Zhong Li. Intensified shape selectivity and alkylation reaction for the two-step conversion of methanol aromatization to p-xylene[J]. 中国化学工程学报, 2023, 59(7): 240-250.
[4]	Haodi Tan, Minjiao Yang, Yingquan Chen, Xu Chen, Francesco Fantozzi, Pietro Bartocci, Roman Tschentscher, Federica Barontini, Haiping Yang, Hanping Chen. Preparation of aromatic hydrocarbons from catalytic pyrolysis of digestate[J]. 中国化学工程学报, 2023, 57(5): 1-9.
[5]	Chenyang Zhao, Yinhan Cheng, Guangfei Qu, Yongheng Yuan, Fenghui Wu, Ye Liu, Shan Liu, Junyan Li, Ping Ning. High-performance liquid-phase catalytic purification of phosphine in tail gas using Pd(II)/Cu(II) composite[J]. 中国化学工程学报, 2023, 57(5): 98-108.
[6]	Juan Du, Aibing Chen, Senlin Hou, Xueqing Gao. Self-deposition for mesoporous carbon nanosheet with supercapacitor application[J]. 中国化学工程学报, 2023, 55(3): 34-40.
[7]	Mengting Liu, Xuexue Dong, Zengjing Guo, Aihua Yuan, Shuying Gao, Fu Yang. Enabling tandem oxidation of benzene to benzenediol over integrated neighboring V-Cu oxides in mesoporous silica[J]. 中国化学工程学报, 2023, 55(3): 236-245.
[8]	Qian Zhu, Yan Zhuang, Hongqing Zhao, Peng Zhan, Cong Ren, Changsheng Su, Wenqiang Ren, Jiawen Zhang, Di Cai, Peiyong Qin. 2,5-Diformylfuran production by photocatalytic selective oxidation of 5-hydroxymethylfurfural in water using MoS₂/CdIn₂S₄ flower-like heterojunctions[J]. 中国化学工程学报, 2023, 54(2): 180-191.
[9]	Eid H. Alosaimi, Ibrahim Hotan Alsohaimi, Hassan M.A. Hassan, Qiao Chen, Saad Melhi, Ayman Abdelaziz Younes. Towards superior permeability and antifouling performance of sulfonated polyethersulfone ultrafiltration membranes modified with sulfopropyl methacrylate functionalized SBA-15[J]. 中国化学工程学报, 2023, 53(1): 89-100.
[10]	Wenjuan Yan, Puhua Sun, Chen Luo, Xingfan Xia, Zhifei Liu, Yuming Zhao, Shuxia Zhang, Liang Sun, Feng Du. PtCo-based nanocatalyst for oxygen reduction reaction: Recent highlights on synthesis strategy and catalytic mechanism[J]. 中国化学工程学报, 2023, 53(1): 101-123.
[11]	Kechang Gao, Shengjuan Shao, Zhixing Li, Jiaxin Jing, Weizhou Jiao, Youzhi Liu. Kinetics of the direct reaction between ozone and phenol by high-gravity intensified heterogeneous catalytic ozonation[J]. 中国化学工程学报, 2023, 53(1): 317-323.
[12]	Yishuang Wang, Na Li, Mingqiang Chen, Defang Liang, Chang Li, Quan Liu, Zhonglian Yang, Jun Wang. Glycerol steam reforming over hydrothermal synthetic Ni-Ca/attapulgite for green hydrogen generation[J]. 中国化学工程学报, 2022, 48(8): 176-190.
[13]	Jinglei Cui, Qian Wang, Jianming Gao, Yanxia Guo, Fangqin Cheng. The selective adsorption of rare earth elements by modified coal fly ash based SBA-15[J]. 中国化学工程学报, 2022, 47(7): 155-164.
[14]	Shuo Li, Jianlin Cao, Xiang Feng, Yupeng Du, De Chen, Chaohe Yang, Wenhua Wang, Wanzhong Ren. Insights into the confinement effect on isobutane alkylation with C₄ olefin catalyzed by zeolite catalyst: A combined theoretical and experimental study[J]. 中国化学工程学报, 2022, 47(7): 174-184.
[15]	Zhouxin Chang, Feng Yu, Zhisong Liu, Zijun Wang, Jiangbing Li, Bin Dai, Jinli Zhang. Ni-Al mixed metal oxide with rich oxygen vacancies: CO methanation performance and density functional theory study[J]. 中国化学工程学报, 2022, 46(6): 73-83.