固体酸催化剂的制备及其催化合成二芳基乙烷的研究
摘要
二芳基乙烷(PXE)因其具有沸点高、粘度小、高溶解、凝点低、显色能力强以及耐高电压等优点,被广泛用于无碳复写纸压敏染料的溶剂及电气绝缘油等。目前,国内二芳基乙烷产品主要靠进口,市场几乎全部被国外厂商占领。因此研究新型催化合成二芳基乙烷的方法无论在理论上还是在工业上都具有重要的意义。
考察了模板剂、硅铝比等制备条件对合成分子筛A1-MCM-41的影响。得出较佳合成条件为:以硅酸钠为硅源,硫酸铝为铝源,以CTAB为模板剂,采用水热法合成了负载型固体酸A1-MCM-41介孔分子筛。并通过X射线衍射(XRD)、热重差热分析(TG-DTA)、扫描电镜(SEM)、透射电镜(TEM)和红外(IR)等对其进行了表征,从而检测了催化剂的活性物质组成、结构。
考察了磷钨酸负载型固体酸催化剂的制备条件,其较佳制备条件为:以HM沸石为载体,采用超声浸渍法制备了的磷钨酸负载型固体酸PW-HM催化剂,并通过XRD、IR、SEM和TEM等方法对其进行了表征。
主要研究了包括Al-MCM-41分子筛和丝光沸石负载磷钨酸型固体酸两类催化剂。同时对该催化剂催化合成二芳基乙烷的合成工艺进行了研究。得出较佳合成条件为:原料苯乙烯与二甲苯质量之比为1∶7 .5,反应温度为140℃,催化剂用量为1 %(总投料质量百分比),反应时间为3 h,产率可达87.1 %,比传统催化剂浓硫酸提高了17 %,研究结果表明,该催化剂是替代传统液体酸催化剂合成二芳基乙烷的理想固体酸催化剂,可以消除以往用液体酸作为催化剂时对设备的腐蚀,避免产生大量的废酸、废水等。为实现以固体酸为催化剂催化合成二芳基乙烷提供了理论依据。
Diphenylethane (PXE) is a colorless synthetic liquid with many excellent properties, such as high-boiling point, small viscosity, low-pour point, strong color ability and high voltage-resistance,which are suitable for various industrial applications, e.g., a solvent for pressure-sensitive record materials, electric-insulating oil etc. At present, The PXE products depend mainly on abroad. So it is significant to study new catalytic synthesis methods of PXE both theoretically and industrially.
The effects of preparation conditions such as the templates, Si-Al ratio on the synthesis of molecular sieve A1-MCM-41 were discussed. The results showed that the optimal conditions were: Na2SiO3 as silica source, Al2(SO4)3 as aluminum source, and cetyltrimethylammonium bromide (CTAB) as template agent under hydrothermal condition. The composition and configuration of A1-MCM-41 molecular sieve are determined by characterization of X-ray diffraction (XRD), thermogravimetry differential thermal analysis (TG-DTA), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and infrared spectroscopy (IR).
The proper conditions of preparating supported catalyst PW/HM have been obtained: it was prepared by ultrasonic treatment during the impregnation step, with HM zeolite as a carrier. Structural and physical properties of the catalysts were characterized by XRD、IR、SEM and TEM.
Two kinds of catalysts Al-MCM-41 mesoporous sieves catalysts and H3PW12O40 supported mordenite(HM)catalysts have been prepared in this thesis. The synthesis of diphenylethane with these catalysts and their catalytic performance were investigated. The optimal conditions were: the mass percent of catalyst was 1 % of feed stock; the weight ratio of xylene to styrene was 7.5: 1; the reaction temperature was 140°C and the time was 3 h. The yield of diphenylethane under such conditions was about 87.1 %, which was 17 % higher than that catalyzed by sulfuric acid. The results showed that Al-MCM-41 and PW-HM might be promising solid acid catalysts instead of liquid acid for synthesis of diphenylethylane. The solid acid can be used to eliminate the corrosion of equipment, and avoid discharge of waste acid and waste water. This work provides a theoretical basis on systhesizing PXE with solid acid as catalyst.
考察了模板剂、硅铝比等制备条件对合成分子筛A1-MCM-41的影响。得出较佳合成条件为:以硅酸钠为硅源,硫酸铝为铝源,以CTAB为模板剂,采用水热法合成了负载型固体酸A1-MCM-41介孔分子筛。并通过X射线衍射(XRD)、热重差热分析(TG-DTA)、扫描电镜(SEM)、透射电镜(TEM)和红外(IR)等对其进行了表征,从而检测了催化剂的活性物质组成、结构。
考察了磷钨酸负载型固体酸催化剂的制备条件,其较佳制备条件为:以HM沸石为载体,采用超声浸渍法制备了的磷钨酸负载型固体酸PW-HM催化剂,并通过XRD、IR、SEM和TEM等方法对其进行了表征。
主要研究了包括Al-MCM-41分子筛和丝光沸石负载磷钨酸型固体酸两类催化剂。同时对该催化剂催化合成二芳基乙烷的合成工艺进行了研究。得出较佳合成条件为:原料苯乙烯与二甲苯质量之比为1∶7 .5,反应温度为140℃,催化剂用量为1 %(总投料质量百分比),反应时间为3 h,产率可达87.1 %,比传统催化剂浓硫酸提高了17 %,研究结果表明,该催化剂是替代传统液体酸催化剂合成二芳基乙烷的理想固体酸催化剂,可以消除以往用液体酸作为催化剂时对设备的腐蚀,避免产生大量的废酸、废水等。为实现以固体酸为催化剂催化合成二芳基乙烷提供了理论依据。
Diphenylethane (PXE) is a colorless synthetic liquid with many excellent properties, such as high-boiling point, small viscosity, low-pour point, strong color ability and high voltage-resistance,which are suitable for various industrial applications, e.g., a solvent for pressure-sensitive record materials, electric-insulating oil etc. At present, The PXE products depend mainly on abroad. So it is significant to study new catalytic synthesis methods of PXE both theoretically and industrially.
The effects of preparation conditions such as the templates, Si-Al ratio on the synthesis of molecular sieve A1-MCM-41 were discussed. The results showed that the optimal conditions were: Na2SiO3 as silica source, Al2(SO4)3 as aluminum source, and cetyltrimethylammonium bromide (CTAB) as template agent under hydrothermal condition. The composition and configuration of A1-MCM-41 molecular sieve are determined by characterization of X-ray diffraction (XRD), thermogravimetry differential thermal analysis (TG-DTA), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and infrared spectroscopy (IR).
The proper conditions of preparating supported catalyst PW/HM have been obtained: it was prepared by ultrasonic treatment during the impregnation step, with HM zeolite as a carrier. Structural and physical properties of the catalysts were characterized by XRD、IR、SEM and TEM.
Two kinds of catalysts Al-MCM-41 mesoporous sieves catalysts and H3PW12O40 supported mordenite(HM)catalysts have been prepared in this thesis. The synthesis of diphenylethane with these catalysts and their catalytic performance were investigated. The optimal conditions were: the mass percent of catalyst was 1 % of feed stock; the weight ratio of xylene to styrene was 7.5: 1; the reaction temperature was 140°C and the time was 3 h. The yield of diphenylethane under such conditions was about 87.1 %, which was 17 % higher than that catalyzed by sulfuric acid. The results showed that Al-MCM-41 and PW-HM might be promising solid acid catalysts instead of liquid acid for synthesis of diphenylethylane. The solid acid can be used to eliminate the corrosion of equipment, and avoid discharge of waste acid and waste water. This work provides a theoretical basis on systhesizing PXE with solid acid as catalyst.
引文
[1]韩金梅,赵超,李鹏.发展中的无碳复写纸[J].山东轻工业学院学报, 2006, 20(1): 61-66.
[2]胡惠仁,徐立新,董荣业.造纸化学品[M].北京:化学工业出版社, 2002. 414-418.
[3]曾建平.无碳复写纸生产工艺初探[J].湖南造纸, 1996, (01): 25-28.
[4]马石辉.无碳复写纸市场探析[J].国际造纸, 1998, 17(2): 48-49.
[5]薛之扬.二异丙基萘—生产无碳复写纸的新溶剂[J].煤炭转化, 1992, 15(2): 40-45.
[6]郑鹏宇,秦鹤年.环烷基原油的特性、加工及应用[J].现代商贸工业, 2008, 20(4): 267-269.
[7] B.S Kwak, T.J Kim. Synthesis of 1-phenyl-1-xylyl ethane by Friedel–Craftsalkylation of xylene withα-methylbenzyl alcohol over mordenite[J]. Catalysis Letters, 1999, 59: 55-60.
[8]林晨,李瑞莲.合成二芳基乙烷技术进展[J].福建化工, 2004, 1: 19-21.
[9] B.S. Kwak. Applications of heterogeneous catalytic processesto the environmentally friendly synthesis of fine chemicals[J]. Catalysis Surveys from Asia, 2005, 9(2): 103-116.
[10]王春华,纪春暖,曲荣君,孙昌梅,王静.稀土La3+掺杂固体超强SO42-/TiO2催化合成二芳基乙烷的研究[J].化学研究与应用, 2005, 17(1): 78-80.
[11]任涛,侯鑫,王富丽,肖兵,王学丽,连丕勇.新型固体超强酸SO42-/ZrO2/MCM-41催化合成二芳基乙烷的研究[J].工业催化, 2006, 14(11): 37-40.
[12]王春华,曲荣君,纪春暖,孙昌梅,陈希磊.合成二芳基乙烷新工艺的研究[J].化学世界, 2004, 5: 258-261.
[13]唐清华.稀土固体超强酸SO42-/TiO2/Sm3+催化合成二芳基乙烷的研究[J].化学工程师, 2005, 4: 11-13.
[14] Aida Yoshiaki,Torii Michiaki, Isoo shimizu.α-Methylbenzylation of alkylberzenes with styrene: Japan, 4897858[P]. 1973-12-13.
[15] E Eldon. Stahly.High energy fuels and methods: USA, 3272879[P].1966-09-13.
[16] Baba Minoru. PreParation of 1,1-diarylethanes: Japan, 55136237[P]. 1980-10-23.
[17]杜诗初,丁颖,狄兆祥.二芳基乙烷合成的研究[J].河南科学, 1992, 10(3): 246-249.
[18]张力.无碳复写纸用溶剂油的研制及应用[J].造纸化学品, 2000, (4): 45-46.
[19] Rober L.Mclaughlin. Aralkylation of arortmtics with styrenes: USA, 3069478[P]. 1962-12- 18.
[20] Naruse Yoshihiro, Yamamoto Seiji, Takagi Katsuhiko. PreParation of diPheny-lalkarles by Y zeolite-catalyzed addition reaction of styrenes with alkylbenzenes: Japan, 63238028[P]. 1988-10-04.
[21]部柄声,洪承权,金泰镇.制备二芳基乙烷的方法: CN, 1288452A[P]. 2001-03-21.
[22] KWAK Byong Sung, HONG Seung Dweon, KIM Tae Jin. Method for diarylethane: W0, 9936377[P]. 1999-07-22.
[23] Byong Sung Kwak, Seung Dweon Hong, Tae Jin KIM. Method for diarylethane: US, 6395947[P]. 2002-05-28.
[24]陈莹莹,强敏,李莉.新型粘土固体酸催化剂合成二芳基乙烷[J].应用化工, 2007, 36(1): 58-60.
[25]张江. MCM-41固载超强酸SO2-4/ZrO2(Ⅱ)催化合成二芳基乙烷的研究[J].首都师范大学学报(自然科学版), 2008, 29(2): 27-30.
[26] D H Everett. IUPAC manual of symbols and terminology[J]. Pure Appl Chem, 1972, 31: 578- 638.
[27]王旭华.模板法制备介孔材料及其表征[D].安徽:安徽大学, 2004.
[28] Y. Cesteros, G.L. Haller. Several factors affecting Al-MCM-41 synthesis[J]. Microporous and Mesoporous Materials, 2001, 43: 171-179.
[29] M.V. Landau, E. Dafa, M.L Kaliya, T.Sen, M. Herskowiz. Mesoporous alumina catalytic material prepared by grafting wide-pore MCM-41 with an alumina multilayer[J]. Microporous and Mesoporous Materials, 2001, 49: 65-81.
[30] X.S. Zhao, G.Q. Lu, X. Hu. Characterization of the structural and surface properties of chemi- cally modified MCM-41 material[J]. Microporous and Mesoporous Materials, 2000, 41: 37-47.
[31]马广伟,葛学贵,黄少云.活性元素负载中孔分子筛的合成及表征研究[J].应用化工, 2003, 32(1): 1-4.
[32] M. Karthik, A.K. Tripathi, N.M. Gupta, A. Vinuc, M. Hartmann, M. Palanichamy, V. Muru- gesan. Characterization of Co,Al-MCM-41 and its activity in the t-butylation of phenol using isobutanol [J]. Applied Catalysis A: General, 2004, 268: 139-149.
[33]张立德,牟季美.纳米材料和纳米结构[M].北京:科学出版社, 2001, 413-437.
[34] Kugita Tsuyoshi, K. Jana Suman, Owada Tomo, Naoki Hashimoto, Onaka Makoto, Namba Seitaro. Mesoporous Al-containing MCM-41 molecular sieves: highly active catalysts for Diels– Alder reaction of cyclopentadiene withα,β-unsaturated aldehydes[J]. Applied Catalysis A: General, 2003, 245: 253-362.
[35]张君.不同孔径介孔分子筛MCM-41的合成与其吸附性能研究[D].北京:中国地质大学, 2006.
[36]许俊强,储伟,陈慕华,罗仕忠,张涛.介孔分子筛V-MCM-41的水热法制备与合成机理[J].催化学报, 2006, 27(8): 671-676.
[37]曾国坪,李湘祁,林辉,汤德平. MCM-41的微波合成与比较[J].材料导报, 2005, 19: 45-48.
[38]覃红丽,李湘祁,曾国坪,陈彗巧,林辉,汤德平. Y-MCM-41介孔分子筛的微波合成与表征[J].福州大学学报(自然科学版), 2005, 33(2): 273-277.
[39]赵杉林,张扬健,孙桂大,翟玉春.钛硅沸石分子筛Ti-MCM-41的微波合成与表征[J].催化学报, 1999, 20(1): 93-95.
[40] H P Lin, C Y Mou, H.S Sheu. Post-synthesis treatment of acid made mesoporous silica materials by ammonia hydrothermal process[J]. Microporous and Mesoporous Materials, 2001, 129: 44-45.
[41] J He, X R Yang. New methods to remove organic templates from porous materials[J]. Mater Chem Phys, 2003, 77: 270-276.
[42] T Shunsuke. N Norikazu. Yoshiaki. Improve thermal stability of mesoporous molecular sieves by vapor infiltration treatment[J]. Microporous and Mesoporous Materials, 2003, 63: 105-109.
[43]钱家盛,王旭华,章于川.介孔材料的制备及表征[J].中国粉体技术, 2005, 11(1): 36-38.
[44] S Cui, C Z Lu, Y L Qiao. Large-scale Preparation of Carbon Nanotubes by Nickel Catalyzed Decomposition of Methane at 100℃[ J]. Carbon, 1999, 37(12): 2070-2081.
[45]刘永梅,赵彦生,窦涛.超声波对合成介孔材料Al-MCM-41的有序度的影响[J].应用声学, 2008, 27(3): 239-243.
[46]秦英月.超声波条件下MCM-41介孔分子筛的合成[D].山西:太原理工大学, 2005.
[47] S Chiarakorn, T Areerob, N Grisdanurak. Influence of functional silanes on hydrophobicity of MCM-41 synthesized from rice husk[J]. Science and Technology of Advanced Materials, 2007(8): 110-115.
[48]侯贵华,罗驹华,陈景文.用稻壳灰为硅源合成有序介孔二氧化硅材料的研究[J].材料科学与工程学报, 2006, 24(4): 528-530.
[49]赵伟,姚建东,黄茜丹,李全芝.以混合非离子-阳离子表面活性剂为模板合成中孔MCM-48[J].科学通报, 2001, (7): 1089-1091.
[50] M. Tiemann, M. Froba, G. Rapp. Nonaqueous Synthesis of Mesostructured Aluminphosphate / Surfactant Composites : Sythesis, Characterization, and In-Situ SAXS Studies[J]. Chem. Mater, 2000, (12): 1342-1348.
[51]刘超,成国祥.模板法制备介孔材料的研究进展[J].离子交换与吸附, 2003, 19(4): 374 -384.
[52] J S Beck, J C Vartuli, W J Roth. A new family of mesoporous molecular sieves prepared with liquid crystal templates[J], Am Chem Soe, 1992, 114: 10834-10843.
[53] Leandro Martins, Tito J. Bonagamba, R Eduardo. de Azevedo, Pascal Bargiela. Surfactant containing Si-MCM-41: An efficient basic catalyst for the Knoevenagel condensation[J]. Applied Catalysis A: General, 2006, 312: 77-85.
[54] A Comm, A Martinez. Hydrocraeking of vacuum gasoil on the novel mesoporous MCM-4 1 aluminosilieates catalysts[J]. Catalysis, 1995, 153: 25-31.
[55] T Blaseo, A Corma, T Navarro. Synthesis, characterization, and catalytic acitivity of Ti, MCM-41 structures[J]. Catalysis, 1995, 156: 65-74.
[56] P V Adhyapak, P Karandikar, K Vijayamohanan. Syhthesis of silver nanowires inside mesoporous MCM-41 host[J]. Mater Lett, 2004, 58: l168-1171.
[57] M T Bore, H N Pham, E Switzer. The role of pore size and structure on the thermal stability of gold nanoparticles within mesoporous silica[J]. Phys Chem B, 2005, 109(7): 2873-288.
[58]赵修松,王情遐,徐龙伢.一种新型中孔3.8nm沸石MCM-41的合成[J].科学通报, 1995, 40(16): 1476-1479.
[59]孙研,林文勇,庞文琴.中孔分子筛MCM-41的合成与表征[J].高等学校化学学报, 1995, 16(9): 1334-133.
[60]袁忠勇,刘述全,龙湘云.含钛MCM-41分子筛的合成与表征[J].离子交换与吸附, 1995, 11(4): 354-359.
[61]何静,段雪, Howe R F. Cr/MCM-41催化剂的结构特征及其纳米尺寸孔内聚乙烯的形成[J].化学学报, 1999, 57: 125-131.
[62]何农跃,鲍书林,须沁华.含La的Si-MCM-41的合成及其水热稳定性[J].科学通报, 1997, 42(2): 165-168.
[63]郑珊,高濂,郭景坤.金属Pl团簇在氧化钛修饰MCM-41中的组装[J].无机材料学报, 2001, 16(6): 1235-1238.
[64]申宝剑,任申勇,郭巧霞.茂锆金属配合物在介孔分子筛MCM-41上的接枝研究[J].分子催化, 2004, 18(2): 93-97.
[65]陈静,韩梅,孙蕊,王锦堂.苄基磺酸接枝MCM-41介孔分子筛的合成与表征[J].无机化学学报, 2006 (9): 25-29.
[66]张铭金,郑安民,邓风,岳勇,叶朝辉.沸石分子筛催化剂的表面化学修饰及其蔡烷基化反应性能[J].中国科学(B辑), 2002, 32(6): 509-514.
[67]王大全,于世涛,刘福胜,张培青,吕志果,李露,刘仕伟.固体酸与精细化工[M].北京:化学工业出版社, 2006. 76-79.
[68]蒋冬梅.改性沸石负载杂多酸烷烃异构化催化剂研究[D].南京:南京工业大学, 2003.
[69] J.-H. Kim, y. Sugi, T. Matsuzaki, T. Hanaoka, Y. Kubota, X. Tu. Effect of SiO2/A1203 ratio of H-mordenite on the isopropylation ofnaphthalene with propylene[J]. Microporous Materials, 1995, 5: 113-121.
[70]柯于勇,张盈珍,王军,周贤敏,许章林.改性丝光沸石上甲醇胺化的研究—水汽处理对沸石性能的影响[J].分子催化, 1997, 2: 121-126.
[71]李晓峰,吕志平,李玉平.丝光沸石应用研究进展[J].应用研究, 2004, (3): 73-77.
[72] J.-H. Kim, Y. Sugi, T. Matsuzaki, T. Hanaoka, y. Kubota, X. Tu, M. Matsumoto, S. Nakata, A. Kato, G. Seo, C. Pak. Cerium impregnated H-mordenite as a catalyst for shape-selective isopropy- lation of naphthalene.Selective deactivation of acid sites on the external surface[J]. Applied Catalysis A: General, 1995, 131: 15-32.
[73] T.Hanaoka, K. Nakajima, Y.Sugi, T.Matsuzaki, Y.Kubota, S. Tawada, K. Kunimori and A. Igarashi. Effects of SiO2/Al2O3 ratio of H-mordenite on encapsulated products inside the pores in shape- selective isopropylation of biphenyl[J]. Catalysis Letters, 1998, 50: 149-152.
[74]刘琪英,王军,武文良,王延儒.改性丝光沸石催化剂上合成2,6-二异丙基萘[J].南京工业大学学报, 2004, 26(2): 8-13.
[75]周志伟,武文良,罗娟,余丽品,王军. H型丝光沸石催化剂催化甲苯与叔丁醇的烷基化反应[J].石油化工, 2006, 35(1): 79-83.
[76]武文良.萘的异丙基化反应催化剂研究[D].南京:南京工业大学, 2005.
[77]李忠燕,涂永善,杨朝合. MCM-41介孔分子筛改性研究新进展[J].工业催化, 2005, 13(2): 12-18.
[78] Congxia Xie, Fusheng Liu, Shitao Yu, Fangfei Xie, LuLi, Shufen Zhang, Jinzong Yang. Study on catalytic pyrolysis of polystyrene over base modified silicon mesoporous molecular sieve[J]. Catalysis Communications, 2008, 9: 1132-1136.
[79]迟彩霞,李晓旭,魏长平. Al-MCM-41介孔材料的合成与表征[J].长春理工大学学报, 2006, 29(3): 85-87.
[80]张铭金,姚瑞平,赵惠忠,陈雷,邓风.杂原子介孔分子筛MCM-41的合成与表征[J].武汉科技大学学报(自然科学版), 2005, 28(2): 154-157.
[81] J.S Beck, J.C Vartuli, W.J Roth, M E Leonowicz, C T Kresge, K D Schmitt, C T-W Chu, D H Olson, E W Sheppard, S B McCullen, J B Higgins, J L Schlenkert. A new family of mesoporous molecular sieves prepared with liquid crystal template[J]. Journal of American Chemical Society, 1992, 114(27): 10834-10843.
[82]谢芳菲,刘福胜,解从霞,于世涛,葛晓萍.中孔分子筛AI-MCM-41的制备及催化聚乙烯裂解反应[J].青岛科技大学学报, 2007, 28(1): 34-38.
[83] Griselda A. Eimer, Liliana B. Pierella, Gustavo A. Monti, Oscar A. Anunziata. Preparation and characterization of aluminium-containing MCM-41[J]. Catalysis Communications, 2003, 4: 118-123.
[84] A Palani, A Pandurangan. Esterification of Terephthalic Acid with Methanol over Mesoporous Al-MCM-41 Molecular Sieves[J]. J Mole Catal A: Chemical, 2006, 245:101-109.
[85]陶涛. MCM-41介孔分子筛的合成方法及催化性能研究[D].江苏:江苏大学, 2006.
[86]赵忠奎,李宗石,王桂茹,乔卫红,程侣伯.杂多酸催化剂及其在精细化学品合成中的应用[J].化学进展, 2004, 16 (4): 620-630.
[87] I V Kozhevnikov. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions[J]. Chem Rev, 1998, 98: 171-198.
[88]吴越,叶兴凯,杨向光.杂多酸的固载化-关于制备负载型酸催化剂的一般原理[J].分子催化, 1996, 10 (4): 299-319.
[89] T Nakato; H Vazquez; T Nishimura. Microstructure of cesium hydrogen salts of 12-tungstophoric acid relevant to novel acid catalysis[J]. Chem. Mater, 2000, 12 (8): 2230-2238.
[90] T Yamase; H Vazquez. Photoredox chemistry of Keggin dodecatungstoborate and role of heterogeneous catalysis in hydrogen formation[J]. J. Chem. Soc., Dalton Trans, 1987: 1597-1604.
[91]王新平,叶兴凯,吴越.杂多酸的固载化研究[J].物理化学学报, 1994, 4: 115-124.
[92] S Kasztelan; J B Moffat. The oxidation of methane on heteropolyoxometalatesⅠ: catalytic properties of silica-supported heteropolyacids[J]. J Catal, 1987, 106: 512-514.
[93]王少鹏,薛建伟,刘春丽.分子筛负载杂多酸催化剂的研究[J].山西化工, 2006, 26(6): 26-39.
[94]梁新义,张黎明,丁宏远,秦永宁.超声促进浸渍法制备催化剂LaCoO3/γ-A1203[J].物理化学学报, 2003, 19(7): 666-669.
[95] Dingfeng Jin, Zhaoyin Hou, Yongming Luo, Xiaoming Zheng. Synthesis of dimethyl- diphenylmethane over supported 12-tungstophosphoric acid (H3PW12O40)[J]. Journal of Molecular Catalysis A: Chemical, 2006243: 233-238.
[96] Dhanashri P. Sawant, A. Vinub, S.P. Mirajkar, F. Lefebvre, K. Ariga, S. Anandanb, T. Mori, C. Nishimura, S.B. Halligudi. Silicotungstic acid/zirconia immobilized on SBA-15 for esterifications [J]. Journal of Molecular Catalysis A: Chemical, 2007,271: 46-56.
[97] Joon Ching Juan, Jingchang Zhang, Mohd Ambar Yarmo. 12-Tungstophosphoric acid supported on MCM-41 for esterification of fatty acid under solvent-free condition[J]. Journal of Molecular Catalysis A: Chemical, 2007, 267: 265-271.
[98] Abd El Rahman S. Khder. Preparation, characterization and catalytic activity of tin oxide- supported 12-tungstophosphoric acid as a solid catalyst[J]. Applied Catalysis A: General, 2008,343: 109-116.
[99] E. Rafiee, F. Paknezhad, Sh. Shahebrahimi, M. Joshaghani, S. Eavani, S. Rashidzadeh. Acid catalysis of different supported heteropoly acids for a one-pot synthesis of _-acetamido ketones[J]. Journal of Molecular Catalysis A: Chemical, 2008, 282: 92-98.
[100] B. Rabindran Jermy, A. Pandurangan. H3PW12O40 supported on MCM-41 molecular sieves: An effective catalyst for acetal formation[J]. Applied Catalysis A: General, 2005, 295: 185-192.
[101] B. Rabindran Jermy, A. Pandurangan. Synthesis of geminal diacetates (acylals) using hetero- geneous H3PW12O40 supported MCM-41 molecular sieves[J]. Catalysis Communications, 2008, 9: 577-583.
[2]胡惠仁,徐立新,董荣业.造纸化学品[M].北京:化学工业出版社, 2002. 414-418.
[3]曾建平.无碳复写纸生产工艺初探[J].湖南造纸, 1996, (01): 25-28.
[4]马石辉.无碳复写纸市场探析[J].国际造纸, 1998, 17(2): 48-49.
[5]薛之扬.二异丙基萘—生产无碳复写纸的新溶剂[J].煤炭转化, 1992, 15(2): 40-45.
[6]郑鹏宇,秦鹤年.环烷基原油的特性、加工及应用[J].现代商贸工业, 2008, 20(4): 267-269.
[7] B.S Kwak, T.J Kim. Synthesis of 1-phenyl-1-xylyl ethane by Friedel–Craftsalkylation of xylene withα-methylbenzyl alcohol over mordenite[J]. Catalysis Letters, 1999, 59: 55-60.
[8]林晨,李瑞莲.合成二芳基乙烷技术进展[J].福建化工, 2004, 1: 19-21.
[9] B.S. Kwak. Applications of heterogeneous catalytic processesto the environmentally friendly synthesis of fine chemicals[J]. Catalysis Surveys from Asia, 2005, 9(2): 103-116.
[10]王春华,纪春暖,曲荣君,孙昌梅,王静.稀土La3+掺杂固体超强SO42-/TiO2催化合成二芳基乙烷的研究[J].化学研究与应用, 2005, 17(1): 78-80.
[11]任涛,侯鑫,王富丽,肖兵,王学丽,连丕勇.新型固体超强酸SO42-/ZrO2/MCM-41催化合成二芳基乙烷的研究[J].工业催化, 2006, 14(11): 37-40.
[12]王春华,曲荣君,纪春暖,孙昌梅,陈希磊.合成二芳基乙烷新工艺的研究[J].化学世界, 2004, 5: 258-261.
[13]唐清华.稀土固体超强酸SO42-/TiO2/Sm3+催化合成二芳基乙烷的研究[J].化学工程师, 2005, 4: 11-13.
[14] Aida Yoshiaki,Torii Michiaki, Isoo shimizu.α-Methylbenzylation of alkylberzenes with styrene: Japan, 4897858[P]. 1973-12-13.
[15] E Eldon. Stahly.High energy fuels and methods: USA, 3272879[P].1966-09-13.
[16] Baba Minoru. PreParation of 1,1-diarylethanes: Japan, 55136237[P]. 1980-10-23.
[17]杜诗初,丁颖,狄兆祥.二芳基乙烷合成的研究[J].河南科学, 1992, 10(3): 246-249.
[18]张力.无碳复写纸用溶剂油的研制及应用[J].造纸化学品, 2000, (4): 45-46.
[19] Rober L.Mclaughlin. Aralkylation of arortmtics with styrenes: USA, 3069478[P]. 1962-12- 18.
[20] Naruse Yoshihiro, Yamamoto Seiji, Takagi Katsuhiko. PreParation of diPheny-lalkarles by Y zeolite-catalyzed addition reaction of styrenes with alkylbenzenes: Japan, 63238028[P]. 1988-10-04.
[21]部柄声,洪承权,金泰镇.制备二芳基乙烷的方法: CN, 1288452A[P]. 2001-03-21.
[22] KWAK Byong Sung, HONG Seung Dweon, KIM Tae Jin. Method for diarylethane: W0, 9936377[P]. 1999-07-22.
[23] Byong Sung Kwak, Seung Dweon Hong, Tae Jin KIM. Method for diarylethane: US, 6395947[P]. 2002-05-28.
[24]陈莹莹,强敏,李莉.新型粘土固体酸催化剂合成二芳基乙烷[J].应用化工, 2007, 36(1): 58-60.
[25]张江. MCM-41固载超强酸SO2-4/ZrO2(Ⅱ)催化合成二芳基乙烷的研究[J].首都师范大学学报(自然科学版), 2008, 29(2): 27-30.
[26] D H Everett. IUPAC manual of symbols and terminology[J]. Pure Appl Chem, 1972, 31: 578- 638.
[27]王旭华.模板法制备介孔材料及其表征[D].安徽:安徽大学, 2004.
[28] Y. Cesteros, G.L. Haller. Several factors affecting Al-MCM-41 synthesis[J]. Microporous and Mesoporous Materials, 2001, 43: 171-179.
[29] M.V. Landau, E. Dafa, M.L Kaliya, T.Sen, M. Herskowiz. Mesoporous alumina catalytic material prepared by grafting wide-pore MCM-41 with an alumina multilayer[J]. Microporous and Mesoporous Materials, 2001, 49: 65-81.
[30] X.S. Zhao, G.Q. Lu, X. Hu. Characterization of the structural and surface properties of chemi- cally modified MCM-41 material[J]. Microporous and Mesoporous Materials, 2000, 41: 37-47.
[31]马广伟,葛学贵,黄少云.活性元素负载中孔分子筛的合成及表征研究[J].应用化工, 2003, 32(1): 1-4.
[32] M. Karthik, A.K. Tripathi, N.M. Gupta, A. Vinuc, M. Hartmann, M. Palanichamy, V. Muru- gesan. Characterization of Co,Al-MCM-41 and its activity in the t-butylation of phenol using isobutanol [J]. Applied Catalysis A: General, 2004, 268: 139-149.
[33]张立德,牟季美.纳米材料和纳米结构[M].北京:科学出版社, 2001, 413-437.
[34] Kugita Tsuyoshi, K. Jana Suman, Owada Tomo, Naoki Hashimoto, Onaka Makoto, Namba Seitaro. Mesoporous Al-containing MCM-41 molecular sieves: highly active catalysts for Diels– Alder reaction of cyclopentadiene withα,β-unsaturated aldehydes[J]. Applied Catalysis A: General, 2003, 245: 253-362.
[35]张君.不同孔径介孔分子筛MCM-41的合成与其吸附性能研究[D].北京:中国地质大学, 2006.
[36]许俊强,储伟,陈慕华,罗仕忠,张涛.介孔分子筛V-MCM-41的水热法制备与合成机理[J].催化学报, 2006, 27(8): 671-676.
[37]曾国坪,李湘祁,林辉,汤德平. MCM-41的微波合成与比较[J].材料导报, 2005, 19: 45-48.
[38]覃红丽,李湘祁,曾国坪,陈彗巧,林辉,汤德平. Y-MCM-41介孔分子筛的微波合成与表征[J].福州大学学报(自然科学版), 2005, 33(2): 273-277.
[39]赵杉林,张扬健,孙桂大,翟玉春.钛硅沸石分子筛Ti-MCM-41的微波合成与表征[J].催化学报, 1999, 20(1): 93-95.
[40] H P Lin, C Y Mou, H.S Sheu. Post-synthesis treatment of acid made mesoporous silica materials by ammonia hydrothermal process[J]. Microporous and Mesoporous Materials, 2001, 129: 44-45.
[41] J He, X R Yang. New methods to remove organic templates from porous materials[J]. Mater Chem Phys, 2003, 77: 270-276.
[42] T Shunsuke. N Norikazu. Yoshiaki. Improve thermal stability of mesoporous molecular sieves by vapor infiltration treatment[J]. Microporous and Mesoporous Materials, 2003, 63: 105-109.
[43]钱家盛,王旭华,章于川.介孔材料的制备及表征[J].中国粉体技术, 2005, 11(1): 36-38.
[44] S Cui, C Z Lu, Y L Qiao. Large-scale Preparation of Carbon Nanotubes by Nickel Catalyzed Decomposition of Methane at 100℃[ J]. Carbon, 1999, 37(12): 2070-2081.
[45]刘永梅,赵彦生,窦涛.超声波对合成介孔材料Al-MCM-41的有序度的影响[J].应用声学, 2008, 27(3): 239-243.
[46]秦英月.超声波条件下MCM-41介孔分子筛的合成[D].山西:太原理工大学, 2005.
[47] S Chiarakorn, T Areerob, N Grisdanurak. Influence of functional silanes on hydrophobicity of MCM-41 synthesized from rice husk[J]. Science and Technology of Advanced Materials, 2007(8): 110-115.
[48]侯贵华,罗驹华,陈景文.用稻壳灰为硅源合成有序介孔二氧化硅材料的研究[J].材料科学与工程学报, 2006, 24(4): 528-530.
[49]赵伟,姚建东,黄茜丹,李全芝.以混合非离子-阳离子表面活性剂为模板合成中孔MCM-48[J].科学通报, 2001, (7): 1089-1091.
[50] M. Tiemann, M. Froba, G. Rapp. Nonaqueous Synthesis of Mesostructured Aluminphosphate / Surfactant Composites : Sythesis, Characterization, and In-Situ SAXS Studies[J]. Chem. Mater, 2000, (12): 1342-1348.
[51]刘超,成国祥.模板法制备介孔材料的研究进展[J].离子交换与吸附, 2003, 19(4): 374 -384.
[52] J S Beck, J C Vartuli, W J Roth. A new family of mesoporous molecular sieves prepared with liquid crystal templates[J], Am Chem Soe, 1992, 114: 10834-10843.
[53] Leandro Martins, Tito J. Bonagamba, R Eduardo. de Azevedo, Pascal Bargiela. Surfactant containing Si-MCM-41: An efficient basic catalyst for the Knoevenagel condensation[J]. Applied Catalysis A: General, 2006, 312: 77-85.
[54] A Comm, A Martinez. Hydrocraeking of vacuum gasoil on the novel mesoporous MCM-4 1 aluminosilieates catalysts[J]. Catalysis, 1995, 153: 25-31.
[55] T Blaseo, A Corma, T Navarro. Synthesis, characterization, and catalytic acitivity of Ti, MCM-41 structures[J]. Catalysis, 1995, 156: 65-74.
[56] P V Adhyapak, P Karandikar, K Vijayamohanan. Syhthesis of silver nanowires inside mesoporous MCM-41 host[J]. Mater Lett, 2004, 58: l168-1171.
[57] M T Bore, H N Pham, E Switzer. The role of pore size and structure on the thermal stability of gold nanoparticles within mesoporous silica[J]. Phys Chem B, 2005, 109(7): 2873-288.
[58]赵修松,王情遐,徐龙伢.一种新型中孔3.8nm沸石MCM-41的合成[J].科学通报, 1995, 40(16): 1476-1479.
[59]孙研,林文勇,庞文琴.中孔分子筛MCM-41的合成与表征[J].高等学校化学学报, 1995, 16(9): 1334-133.
[60]袁忠勇,刘述全,龙湘云.含钛MCM-41分子筛的合成与表征[J].离子交换与吸附, 1995, 11(4): 354-359.
[61]何静,段雪, Howe R F. Cr/MCM-41催化剂的结构特征及其纳米尺寸孔内聚乙烯的形成[J].化学学报, 1999, 57: 125-131.
[62]何农跃,鲍书林,须沁华.含La的Si-MCM-41的合成及其水热稳定性[J].科学通报, 1997, 42(2): 165-168.
[63]郑珊,高濂,郭景坤.金属Pl团簇在氧化钛修饰MCM-41中的组装[J].无机材料学报, 2001, 16(6): 1235-1238.
[64]申宝剑,任申勇,郭巧霞.茂锆金属配合物在介孔分子筛MCM-41上的接枝研究[J].分子催化, 2004, 18(2): 93-97.
[65]陈静,韩梅,孙蕊,王锦堂.苄基磺酸接枝MCM-41介孔分子筛的合成与表征[J].无机化学学报, 2006 (9): 25-29.
[66]张铭金,郑安民,邓风,岳勇,叶朝辉.沸石分子筛催化剂的表面化学修饰及其蔡烷基化反应性能[J].中国科学(B辑), 2002, 32(6): 509-514.
[67]王大全,于世涛,刘福胜,张培青,吕志果,李露,刘仕伟.固体酸与精细化工[M].北京:化学工业出版社, 2006. 76-79.
[68]蒋冬梅.改性沸石负载杂多酸烷烃异构化催化剂研究[D].南京:南京工业大学, 2003.
[69] J.-H. Kim, y. Sugi, T. Matsuzaki, T. Hanaoka, Y. Kubota, X. Tu. Effect of SiO2/A1203 ratio of H-mordenite on the isopropylation ofnaphthalene with propylene[J]. Microporous Materials, 1995, 5: 113-121.
[70]柯于勇,张盈珍,王军,周贤敏,许章林.改性丝光沸石上甲醇胺化的研究—水汽处理对沸石性能的影响[J].分子催化, 1997, 2: 121-126.
[71]李晓峰,吕志平,李玉平.丝光沸石应用研究进展[J].应用研究, 2004, (3): 73-77.
[72] J.-H. Kim, Y. Sugi, T. Matsuzaki, T. Hanaoka, y. Kubota, X. Tu, M. Matsumoto, S. Nakata, A. Kato, G. Seo, C. Pak. Cerium impregnated H-mordenite as a catalyst for shape-selective isopropy- lation of naphthalene.Selective deactivation of acid sites on the external surface[J]. Applied Catalysis A: General, 1995, 131: 15-32.
[73] T.Hanaoka, K. Nakajima, Y.Sugi, T.Matsuzaki, Y.Kubota, S. Tawada, K. Kunimori and A. Igarashi. Effects of SiO2/Al2O3 ratio of H-mordenite on encapsulated products inside the pores in shape- selective isopropylation of biphenyl[J]. Catalysis Letters, 1998, 50: 149-152.
[74]刘琪英,王军,武文良,王延儒.改性丝光沸石催化剂上合成2,6-二异丙基萘[J].南京工业大学学报, 2004, 26(2): 8-13.
[75]周志伟,武文良,罗娟,余丽品,王军. H型丝光沸石催化剂催化甲苯与叔丁醇的烷基化反应[J].石油化工, 2006, 35(1): 79-83.
[76]武文良.萘的异丙基化反应催化剂研究[D].南京:南京工业大学, 2005.
[77]李忠燕,涂永善,杨朝合. MCM-41介孔分子筛改性研究新进展[J].工业催化, 2005, 13(2): 12-18.
[78] Congxia Xie, Fusheng Liu, Shitao Yu, Fangfei Xie, LuLi, Shufen Zhang, Jinzong Yang. Study on catalytic pyrolysis of polystyrene over base modified silicon mesoporous molecular sieve[J]. Catalysis Communications, 2008, 9: 1132-1136.
[79]迟彩霞,李晓旭,魏长平. Al-MCM-41介孔材料的合成与表征[J].长春理工大学学报, 2006, 29(3): 85-87.
[80]张铭金,姚瑞平,赵惠忠,陈雷,邓风.杂原子介孔分子筛MCM-41的合成与表征[J].武汉科技大学学报(自然科学版), 2005, 28(2): 154-157.
[81] J.S Beck, J.C Vartuli, W.J Roth, M E Leonowicz, C T Kresge, K D Schmitt, C T-W Chu, D H Olson, E W Sheppard, S B McCullen, J B Higgins, J L Schlenkert. A new family of mesoporous molecular sieves prepared with liquid crystal template[J]. Journal of American Chemical Society, 1992, 114(27): 10834-10843.
[82]谢芳菲,刘福胜,解从霞,于世涛,葛晓萍.中孔分子筛AI-MCM-41的制备及催化聚乙烯裂解反应[J].青岛科技大学学报, 2007, 28(1): 34-38.
[83] Griselda A. Eimer, Liliana B. Pierella, Gustavo A. Monti, Oscar A. Anunziata. Preparation and characterization of aluminium-containing MCM-41[J]. Catalysis Communications, 2003, 4: 118-123.
[84] A Palani, A Pandurangan. Esterification of Terephthalic Acid with Methanol over Mesoporous Al-MCM-41 Molecular Sieves[J]. J Mole Catal A: Chemical, 2006, 245:101-109.
[85]陶涛. MCM-41介孔分子筛的合成方法及催化性能研究[D].江苏:江苏大学, 2006.
[86]赵忠奎,李宗石,王桂茹,乔卫红,程侣伯.杂多酸催化剂及其在精细化学品合成中的应用[J].化学进展, 2004, 16 (4): 620-630.
[87] I V Kozhevnikov. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions[J]. Chem Rev, 1998, 98: 171-198.
[88]吴越,叶兴凯,杨向光.杂多酸的固载化-关于制备负载型酸催化剂的一般原理[J].分子催化, 1996, 10 (4): 299-319.
[89] T Nakato; H Vazquez; T Nishimura. Microstructure of cesium hydrogen salts of 12-tungstophoric acid relevant to novel acid catalysis[J]. Chem. Mater, 2000, 12 (8): 2230-2238.
[90] T Yamase; H Vazquez. Photoredox chemistry of Keggin dodecatungstoborate and role of heterogeneous catalysis in hydrogen formation[J]. J. Chem. Soc., Dalton Trans, 1987: 1597-1604.
[91]王新平,叶兴凯,吴越.杂多酸的固载化研究[J].物理化学学报, 1994, 4: 115-124.
[92] S Kasztelan; J B Moffat. The oxidation of methane on heteropolyoxometalatesⅠ: catalytic properties of silica-supported heteropolyacids[J]. J Catal, 1987, 106: 512-514.
[93]王少鹏,薛建伟,刘春丽.分子筛负载杂多酸催化剂的研究[J].山西化工, 2006, 26(6): 26-39.
[94]梁新义,张黎明,丁宏远,秦永宁.超声促进浸渍法制备催化剂LaCoO3/γ-A1203[J].物理化学学报, 2003, 19(7): 666-669.
[95] Dingfeng Jin, Zhaoyin Hou, Yongming Luo, Xiaoming Zheng. Synthesis of dimethyl- diphenylmethane over supported 12-tungstophosphoric acid (H3PW12O40)[J]. Journal of Molecular Catalysis A: Chemical, 2006243: 233-238.
[96] Dhanashri P. Sawant, A. Vinub, S.P. Mirajkar, F. Lefebvre, K. Ariga, S. Anandanb, T. Mori, C. Nishimura, S.B. Halligudi. Silicotungstic acid/zirconia immobilized on SBA-15 for esterifications [J]. Journal of Molecular Catalysis A: Chemical, 2007,271: 46-56.
[97] Joon Ching Juan, Jingchang Zhang, Mohd Ambar Yarmo. 12-Tungstophosphoric acid supported on MCM-41 for esterification of fatty acid under solvent-free condition[J]. Journal of Molecular Catalysis A: Chemical, 2007, 267: 265-271.
[98] Abd El Rahman S. Khder. Preparation, characterization and catalytic activity of tin oxide- supported 12-tungstophosphoric acid as a solid catalyst[J]. Applied Catalysis A: General, 2008,343: 109-116.
[99] E. Rafiee, F. Paknezhad, Sh. Shahebrahimi, M. Joshaghani, S. Eavani, S. Rashidzadeh. Acid catalysis of different supported heteropoly acids for a one-pot synthesis of _-acetamido ketones[J]. Journal of Molecular Catalysis A: Chemical, 2008, 282: 92-98.
[100] B. Rabindran Jermy, A. Pandurangan. H3PW12O40 supported on MCM-41 molecular sieves: An effective catalyst for acetal formation[J]. Applied Catalysis A: General, 2005, 295: 185-192.
[101] B. Rabindran Jermy, A. Pandurangan. Synthesis of geminal diacetates (acylals) using hetero- geneous H3PW12O40 supported MCM-41 molecular sieves[J]. Catalysis Communications, 2008, 9: 577-583.
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