Epoxidation of <em>α</em>-Pinene on Tin-Modified Mesoporous Molecular Sieve SBA-15

化学工业与工程

Chemcial Industry and Engineering

2016, Vol. 33

Issue (1) :29-34 DOI: 10.13353/j.issn.1004.9533.20141140

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Epoxidation of α-Pinene on Tin-Modified Mesoporous Molecular Sieve SBA-15

Liu Huiqing¹, Wu Chunhua¹, Chen Baosen², Gao Mingfu²

1. Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Kunming 650224, China;
2. Chuxiong Hongbang forestry Chemical Limited Company, Chuxiong 675005, China

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Abstract

By hydrothermal synthesis method, mesoporous molecular sieve SBA-15 was obtained with the template P123, then tin modified mesoporous molecular sieve SO₄^2-/Sn/SBA-15 was obtained by impregnation into solution of tin(IV) chloride pentahydrate, then into sulfuric acid. The infrared spectroscopy(IR), thermogravimetric analysis(TG), scanning electron microscopy(SEM) and transmission electron microscopy(TEM) were used to characterize the structure of the catalyst. The performance of the catalyst was studied by epoxidation of α-pinene. The influence of the molar ratio of SBA-15 and SnCl₄·5H₂O, the dosage of catalyst and the molar ratio of peroxyacetic and α-pinene were discussed.The results showed that the conversion rate of α-pinene could reach 95.4%, and the yield of 2,3-epoxypinane was 88.82% when the molar ratio of SBA-15 to SnCl₄·5H₂O was 5:1, dosage of SO₄^2-/Sn/SBA-15 catalyst was 2.5% (α-pinene weight),and the molar ratio of peroxyacetic to α-pinene was 1.2.

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	Liu Huiqing
	Wu Chunhua
	Chen Baosen
	Gao Mingfu

Keywords： mesoporous molecular sieve SBA-15； SO₄^2-/Sn/SBA-15； α-pinene； epoxidation

Received 2014-09-02;

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Liu Huiqing, Wu Chunhua, Chen Baosen, Gao Mingfu.Epoxidation of α-Pinene on Tin-Modified Mesoporous Molecular Sieve SBA-15[J] Chemcial Industry and Engineering, 2016,V33(1): 29-34

[1] Zhao D, Huo J, Stucky G D, et al. Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores[J]. Science, 1998, 279(5 350): 548-552
[2] Zhao D, Sun J, Li Q, et al. Morphological control of highly ordered mesoporous silica SBA-15[J]. Chem Mater, 2000, 12(2): 275-279
[3] Tatsumi T, Keiko A K, Tanaka Y, et al. Mechanochemical collapse of M41S mesoporous molecular sieves through hydrolysis of siloxane bonds[J]. Chemistry Letters, 1997, 1997(5): 469-470
[4] Humphrey H P Y, Paul A W, Nigel P B. Enzyme immobilisation using SBA-15 mesoporous molecular sieves with functionalised surfaces [J]. Journal of Molecular Catalysis B: Enzymatic,2001,15: 81-92
[5] 赵黔榕,吴春华,毕韵梅, 等. 四氯化锡催化合成乙酸松油酯[J]. 合成化学, 2006, 14(3): 290-292 Zhao Qianrong, Wu Chunhua, Bi Yunmei, et al. Synthesis of terpinyl acetate catalyzed by SnCl₄·5H₂O [J]. Chinese Journal of Synthetic Chemistry, 2006, 14(3): 290-292 (in Chinese)
[6] 翁文,许华丽,李国平,等.四氯化锡催化乙酸异戊酯的合成[J]. 应用化学, 2001, 18(3): 244-245 Weng Wen, Xu Huali, Li Guoping, et al. Synthesis of isoamyl acetate catalyzed by SnCl₄·5H₂O[J]. Chinese Journal of Applied Chemistry,2001, 18(3): 244-245 (in Chinese)
[7] 何千乐. 有机化学中的硬软酸碱原理[M]. 北京: 科学出版社, 1987
[8] 张剑锋, 胡岳华, 李晓如, 等. 相转移催化下蒎烯的环氧化反应[ J]. 中南工业大学学报, 2001, 32(1): 50-53 Zhang Jianfeng, Hu Yuehua, Li Xiaoru, et al. Phase-Transfer catalytic epoxidation of α-pinene and β-pinene [J]. Journal of Central South University of Technology, 2001, 32(1): 50-53 (in Chinese)
[9] Lavallee P,Bouthillier G.Efficient conversion of (1R,5R)-(+)-α-pinene to (1S, 5R)-(-)-nopinone[J].J Org Chem, 1986, 51 (8): 1 362-1 365
[10] Maraval V,Ancel J E,Meunier B. Manganese(IlI) porphyrin catalysts for the oxidation of terpene derivatives:A comparative study [J]. J Catal, 2002, 206: 349-357
[11] 丁宗彪,陆文聪,王全瑞.以过碳酸钠为试剂制备环氧蒎烷的方法:中国,1422853A[P].2003-06-11 Ding Zongbiao,Lu Wencong,Wang Quanrui.Method for preparing epoxypinane using sodium percarbonate as reagent:CN, 1422853A[P].2003-06-11 (in Chinese)
[12] Saladino R,Andreoni A,Neri V,et al.A novel and efficient catalystic epoxidation of olefins and monoterpenes with microencapsulated Lewis base adducts of methyltrioxorhenium [J]. Tetrahedron, 2005, 61(5): 1 069-1 073
[13] Silva J M, Vinhado F S, Mandelli D, et al. The chemical reactivity of some terpenes investigated by alumina catalyzed epoxidation with hydrogen peroxide and DFT calculations [J]. Journal of Molecular Catalysis A: Chemical, 2006, 252 (1/2):186-193
[14] Bordoloi A, Lefebvre F, Halligudi S B. Organotin-Oxometalate coordination polymer catalyzed oxyfunctionalization of monoterpenes[J]. Journal of Molecular Catalysis A: Chemical, 2007, 270(1/2):177-184
[15] Tangestaninejad S, Habibi M H, Mirhhani V, et al. Readily prepared polymer-supported molybdenum carbonyls as novel reusable and highly active epoxidation catalysts[J]. Inorganic Chemistry Communications, 2006, 9(6): 575-578
[16] Mirkhani V, Moghadam M, Tangestaninejad S. Host (nanocavity of zeolite-Y)-guest (manganese(Ⅲ) salophen complex) nanocomposite materials: An efficient catalyst for biomimetic alkene epoxidation and alkane hydroxylation with sodium periodate[J]. Applied Catalysis A: General, 2007, 321(1): 49-57
[17] Maksimchuk N V, Melgunov M S, Chesalov Y A, et al. Aerobic oxidations of α-pinene over cobalt-substituted polyoxometalate supported on amino-modified mesoporous silicates[J]. Journal of Catalysis, 2007, 246(2): 241-248
[18] Castro J M, Palomino P J, Salido S, et al. Enantiospecific synthesis, separation and olfactory evaluation of all diasteromers of a homologue of the sandal wood odorant polysantol [J]. Tetrahedron, 2005, 61(47): 11 192-11 203
[19] 王宗德,陈金珠,宋湛谦.8-羟基别二氢葛缕醇甲酸酯及其合成方法和用作驱避剂:中国,1730459A[P]. 2006-02-08 Wang Zongde, Chen Jinzhu, Song Zhanqian. 8-Hydroxyl-Allo-Dihydro-Carvyl formate and its synthesis method and uses as repellent: CN, 173045A [P]. 2006-02-08 (in Chinese)
[20] 袁兴东, 沈建, 李国辉, 等. 表面含磺酸基的介孔分子筛催化剂SBA-15-SO₃H的制备及其催化性能[J]. 高等学校化学学报, 2002, 23(12): 2 332-2 335 Yuan Xingdong, Shen Jian, Li Guohui, et al. Prepararion of highly active esterification catalyst SBA-15 mesoporous silica functionalized with sulfonic acid group [J]. Chemical Journal of Chinese Universities, 2002, 23(12): 2 332-2 335 (in Chinese)
[21] Orlov A, Klinowski J. Oxidation of volatile organic compounds on SBA-15 mesoporous-molecular sieves modifed with manganese[J]. Chemosphere, 2009, 74: 344-348
[22] Pallavi S, Arumugamangalam V R, Karoly L V R. Synthesis and characterization of tin oxide-modified mesoporous SBA-15 molecular sieves and catalytic activity in transesterification reaction[J]. Applied Catalysis A General, 2004, 273: 239-248
[23] 王宇红, 董顺喜, 卢冠忠. 不同稀土改性SO₄^2-/ZrO₂催化剂的结构和性能表征[J].无机化学学报, 2007, 23(4): 677-682 Wang Yuhong, Dong Shunxi, Lu Guanzhong. Structure and catalytic properties of SO₄^2-/ZrO₂ catalyst modified by different rare earth compounds[J]. Chinese Journal of Inorganic Chemistry, 2007, 23(4): 677-682 (in Chinese)
[24] 闫鹏, 郭海福, 舒华, 等. 固体超强酸SO₄^2-/SnO₂-Al₂O₃的红外光谱研究[J].化学研究与应用, 2006, 18(6): 638-642 Yan Peng, Guo Haifu, Shu Hua, et al. FTIR spectra of SO₄^2-/SnO₂-Al₂O₃ solid superacid[J]. Chemical Research and Application, 2006, 18(6): 638-642 (in Chinese)