随着绿色化学的发展,将磺酸基团负载到固体表面制备磺酸型固体酸代替传统的硫酸催化剂越来越受到了人们的关注。为此,综述了磺酸型硅基固体酸的制备方法及应用,介绍了浸渍、接枝和共缩合3种制备方法,探讨了固体酸在酯化、醚化、脱水等反应中的催化活性。
With the development of green chemistry,sulfonic acid group loading to solid surface to prepare sulfonate solid acid instead of traditional sulfuric acid catalyst is getting more and more attention.The preparation methods and application of silica-functionalized sulfonic solid acid catalysts were reviewed,and the three methods including impregnation,grafting and co-condensation were presented.The catalytic activity of sulfonate solid acid in the esterification,etherification,dehydration and so on was discussed.
[1] Yan X M,Lei J H,Liu D et al.Synthesis and catalytic properties of mesoporous phosphotungstic acid/SiO2 in a self-generated acidic environment by evaporation-induced self-assembly[J].Materials Research Bulletin,2007,42(11):1905-1913.
[2] Zhen B,Jiao Q Z,Zhang Y P,et al.Acidic ionic liquid immobilized on magnetic mesoporous silica:preparation and catalytic performance in esterification[J].Applied Catalysis A:General,2012,s445-446(47):239-245.
[3] Karimi B,Zareyee D.A high loading sulfonic acid-functionalized ordered nanoporous silica as an efficient and recyclable catalyst for chemoselective deprotection of tert-butyldimethylsilyl ethers[J].Cheminform,2005,46(27):4661-4665.
[4] Ken-ichi Shimizu,Eidai Hayashi,Tsuyoshi Hatamachi et al.Acidic properties of sulfonic acid-functionalized FSM-16 mesoporous silica and its catalytic efficiency for acetalization of carbonyl compounds[J].Journal of Catalysis,2005,231(1):131-138.
[5] Landge S M,Berryman M,Török B.Microwave-assisted solid acid-catalyzed one-pot synthesis of isobenzofuran-1(3H)-ones[J].Cheminform,2008,49(29-30):4505-4508.
[6] Daryoush Zareyee,Babak Karimi.A novel and highly efficient method for the silylation of alcohols with hexamethyldisilazane(HMDS) catalyzed by recyclable sulfonic acid-functionalized ordered nanoporous silica[J].Tetrahedron Letters,2007,38(19):1277-1280.
[7] Nishita Lucas,Ankur Bordoloi,Amol P,et al.A comparative study on liquid phase alkylation of 2-methylnaphthalene with long chain olefins using different solid acid catalysts[J].Applied Catalysis A:General,2009,352(1-2):74-80.
[8] 胡明华.硅胶负载型催化剂催化下含氮杂环化合物的合成[D].苏州:苏州大学,2014.
[9] 高登征,王力,刘丽华,等.直接法合成疏水介孔分子筛SBA-15-SO3H固体酸及其催化性能[J].山东科技大学学报(自然科学版),2010,29(1):77-80.
[10] 常玥,移永杰,刘婷,等.疏水性SBA-15-SO3H介孔固体酸催化合成偏苯三酸三辛酯[J].西北师范大学学报(自然科学版),2017,53(2):65-69.
[11] 薛来奇.Cu-Al/MCM-41催化剂的改性及在环己醇脱水制环己烯中的应用[J].石河子大学学报(自然版),2017,35(1):34-38.
[12] 吴洁,曾丹林,裴阳,等.SiO2固体酸微球制备及催化性能研究[J].化工新型材料,2017(10):148-150.
[13] Ziarani G M,Badiei A,Abbasi A,et al.Cross-aldol condensation of cycloalkanones and aromatic aldehydes in the presence of nanoporous silica-based sulfonic acid(SiO2-Pr-SO3H) under solvent free conditions[J].Chinese Journal of Chemistry,2009,27(8):1537-1542.
[14] Hermida Lilis,Ahmad Zuhairi Abdullah,Abdul Rahman Mohamed.Synthesis of monoglyceride through glycerol esterification with lauric acid over propyl sulfonic acid post-synthesis functionalized SBA-15 mesoporous catalyst[J].Chemical Engineering Journal,2011,174(2-3):668-676.
[15] Das D,Lee J F,Cheng S.Sulfonic acid functionalized mesoporous MCM-41 silica as a convenient catalyst for bisphenol-a synthesis[J].Chemical Communications,2001,21:2178-2179.
[16] Diaz I,Pariente E,Sastre.Synthesis of MCM-41 materials functionalised with dialkylsilane groups and their catalytic activity in the esterification of glycerol with fatty acids[J].Appl Catal A:Gen,2003,242(1):161-169.
[17] Diaz I,Mohino F,Blasco T,et al.Influence of the alkyl chain length of HSO3-R-MCM-41 on the esterification of glycerol with fatty acids[J].Micropor Mesopor Mater,2005,80(1/2/3):33-42.
[18] 陈静,韩梅,孙蕊,等.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,2006,22(9):1568-1572.
[19] 高国华,周文娟,何鸣元.磺酸基功能化MCM-41有机-无机杂化材料的合成与表征[J].催化学报,2005,26(5):357-359.
[20] 曾昌凤,陈军,张利雄,等.磺酸型固体酸催化剂的制备与应用研究进展[J].南京工业大学学报(自然科学版),2009,31(6):104-110.
[21] Testa M L,Parola V L,Venezia A M.Esterification of acetic acid with butanol over sulfonic acid-functionalized hybrid silicas[J].Catalysis Today,2010,158(1-2):109-113.
[22] Testa M L,Parola V L,Venezia A M.Transesterification of short chain esters using sulfonic acid-functionalized hybrid silicas:effect of silica morphology[J].Catalysis Today,2014,223(223):115-121.
[23] Usai E M,Sini M F,Meloni D,et al.Sulfonic acid-functionalized mesoporous silicas:microcalorimetric characterization and catalytic performance toward biodiesel synthesis[J].Microporous and Mesoporous Materials,2013,179(17):54-62.
[24] Sharifi M,Schneide J,Wark M.Investigation on the optimal oxidation agent for a maximum yield of sulfonic acid groups in MCM-41[J].Microporous and Mesoporous Materials,2012,151(11):506-510.
[25] Gong S,Epasinghe D J,Zhang W,et al.Synthesis of antimicrobial silsesquioxane-silica hybrids by hydrolytic co-condensation of alkoxysilanes[J].Polymer Chemistry,2013,5(2):454-462.
[26] 袁兴东,沈健,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):2332-2335.
[27] 张立,袁兴东,亓玉台,等.含磺酸基的介孔分子筛SBA-15-SO3H催化合成乙酸乙酯[J].辽宁石油化工大学学报,2003,23(2):20-23.
[28] 亢宇,谢伦嘉,王彦强,等.高比表面磺酸基改性介孔材料SBA-16的合成与催化活性[J].硅酸盐学报,2009,37(11):1859-1863.
[29] 方少明,康华魁,王培远,等.磺酸功能化介孔材料的合成及催化性能研究[J].化工新型材料,2014(8):43-45.
[30] Zhou F,Tang J,Fei Z,et al.Efficient cyclohexyl acrylate production by direct addition of acrylic acid and cyclohexene over SBA-15-SO3H[J].Journal of Porous Materials,2014,21(2):149-155.
[31] 刘汝宽,杨喜平,王瑞霞,等.制备生物柴油的催化剂研究进展[J].中国粮油学报,2006,21(3):273-276.
[32] 李飞云,熊开峰,王哲,等.固体酸催化剂在生物柴油制备中的应用研究进展[J].齐鲁工业大学学报,2017,31(1):38-44.
[33] 张景玉,任立国.二氧化硅-磺酸催化棉籽油酯交换制备生物柴油[J].辽宁石油化工大学学报,2009,29(3):41-43.
[34] 任立国,张晓丽,高文艺.二氧化硅负载甲烷磺酸催化酯交换制备生物柴油[J].工业催化,2009,17(10):40-44.
[35] Zuo D,Lane J,Dan C,et al.Sulfonic acid functionalized mesoporous SBA-15 catalysts for biodiesel production[J].Applied Catalysis B Environmental,2013,129(3):342-350.
[36] Tucker M H,Crisci A J,Wigington B N,et al.Acid-functionalized SBA-15-type periodic mesoporous organosilicas and their use in the continuous production of 5-hydroxymethylfurfural[J].Acs Catalysis,2012,2(9):1865-1876.
[37] 蒋成君,尹红,陈志荣.醚化反应法合成乙二醇醚催化剂研究进展[J].工业催化,2004,12(6):20-24.
[38] 史立杰,李晨佳,常俊石.甲醇制二甲醚用全氟磺酸树脂催化剂的研究[J].化工进展,2014,33(8):2066-2071.
[39] González M D,Cesteros Y,Llorca J,et al.Boosted selectivity toward high glycerol tertiary butyl ethers by microwave-assisted sulfonic acid-functionalization of SBA-15 and beta zeolite[J].Journal of Catalysis,2012,290(6):202-209.
[40] Sow B,Hamoudi S,Zahedi-Niaki M H,et al.1-Butanol etherification over sulfonated mesostructured silica and organo-silica[J].Microporous & Mesoporous Materials,2005,79(1-3):129-136.
[41] Tucker M H,Crisci A J,Wigington B N,et al.Acid-functionalized SBA-15-type periodic mesoporous organosilicas and their use in the continuous production of 5-hydroxymethylfurfural[J].Acs Catalysis,2012,2(9):1865-1876.
[42] Graaff W N P V D,Olvera K G,Pidko E A,et al.Stability and catalytic properties of porous acidic (organo)silica materials for conversion of carbohydrates[J].Journal of Molecular Catalysis A Chemical,2014,388-389(s388-389):81-89.
[43] Karimi B,Mirzaei H.The influence of hydrophobic/hydrophilic balance of the mesoporous solid acid catalysts in the selective dehydration of fructose into HMF[J].Rsc Advances,2013,3(43):20655-20661.
[44] Shi X,Wu Y,Yi H,et al.Selective preparation of furfural from xylose over sulfonic acid functionalized mesoporous SBA-15 materials[J].Energies,2011,4(4):669-684.
[45] 胡建,夏成波,彭静,等.磺酸化介孔二氧化硅的合成及催化苯甲醛和乙二醇的加成反应[J].武汉工程大学学报,2011,33(5):34-37.
[46] Daryoush,Zareyee,Rezvaneh,et al.Silylation of alcohols and phenols with hexamethyldisilazane over highly reusable propyl sulfonic acid functionalized nanostructured SBA-15[J].Chinese Journal of Catalysis,2011,32(12):1864-1868.
基金资助
国家自然科学基金项目(21473126);湖北省教育科学规划课题(2016GB023)
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