酯化反应中SO_4~(2-)/氧化物固体超强酸催化剂的研究进展
|
摘要
SO_4~(2-)/氧化物型固体超强酸催化剂在酯化反应中表现出较高的催化活性和重复使用性能,且该催化剂具有易于与产物分离、不腐蚀设备、绿色环保等优点,因此,近年来在工业生产中受到越来越多的关注。简述了固体超强酸的成酸机制及催化反应机制,简要概述了近年来国内外几种SO_4~(2-)/氧化物型固体超强酸催化剂在酯化反应中的研究进展,并对催化剂的制备、相关理论探索、工业应用研究方面进行了展望。
SO_4~(2-)/oxide solid superacid catalyst has been proved to be very effective from the viewpoint of activity and reusability in esterification reaction,which has the advantages of easy product separation,no corrosion of equipment,green environmental protection and so on. Much attention has been paid on its industrial production.The acid-forming mechanism and catalytic mechanism of solid superacid were briefly described,and the research progress of several SO_4~(2-)/oxide solid superacid catalysts in esterification at home and abroad in recent years was summarized.The progress in preparation,theoretical exploration and industrial application of catalysts was discussed.
SO_4~(2-)/oxide solid superacid catalyst has been proved to be very effective from the viewpoint of activity and reusability in esterification reaction,which has the advantages of easy product separation,no corrosion of equipment,green environmental protection and so on. Much attention has been paid on its industrial production.The acid-forming mechanism and catalytic mechanism of solid superacid were briefly described,and the research progress of several SO_4~(2-)/oxide solid superacid catalysts in esterification at home and abroad in recent years was summarized.The progress in preparation,theoretical exploration and industrial application of catalysts was discussed.
引文
[1]林丹.酯化反应催化剂研究新进展[J].能源化工,2017,38(2):41.
[2] REDDY B M,PATIL M K.Organic syntheses and transformations catalyzed by sulfated zirconia[J]. Chemical reviews,2009,109(6):2185.
[3] JING H W,WANG X M,LIU Y,et al. Preparation of magnetic nanocomposites of solid acid catalysts and their applicability in esterification[J].Chinese journal of catalysis,2015,36(2):244.
[4]汪颖军,李言,所艳华,等.负载型氧化物固体超强酸改性的研究进展[J].石油学报(石油加工),2012,28(3):525.
[5] NIU Y,LI F Y,YANG K,et al.Preparation and characterization of sulfated Ti O2with rhodium modification used in esterification reaction and decomposition of methyl orange[J].Chinese journal chemical engineering,2016(24):767.
[6]孟瑶,李锋,宋华.SO2-4/MxOy型固体超强酸酸中心结构及其在轻质烷烃异构化反应中的机理研究进展[J].化工进展,2015,34(11):3906.
[7] LI X,HUANG W.Synthesis of biodiesel from rap oil over sulfated titania-based solid superacid catalysts[J]. Energy sources(recovery,utilization,and environmental effects),2009,31(18):1666.
[8] MANTILLA A,FERRAT G,LOPEZ-ORTEGA A,et al.Catalytic behavior of sulfated Ti O2in light olefins oligomerization[J].Journal of molecular catalysis A(chemical),2005,228(1/2):333.
[9] KHDER A S,EL-SHARKWAY E A,El-HAKAM S A,et al.Surface characterization and catalytic activity of sulfated tin oxide catalyst[J].Catalysis communications,2008,9(5):769.
[10]陈宝树,网凶铃,赵久生,等.新型精细化工讲座[J].精细石油化工,1990(5):63.
[11]周晶,聂晓安,戴伟娣.负载型固体酸催化剂制备生物柴油研究进展[J].生物质化学工程,2008,4(1):41.
[12]于世涛,刘福成.固体酸与精细化工[M].北京:化学工业出版社,2006:15-19.
[13]卢冠忠,江娴,王药松.多组元SO2-4/MxOy型固体超强酸催化酯化反应的研究[J].工业催化,1994(2):14.
[14]曾健青,罗庆云,王琴,等.SO2-4/MxOy型固体超强酸的研究进展[J].石油化工,1994,23(3):191.
[15] HINO M,ARATA K. Synthesis of solid super acid of tuugsten oxide supported on zirconia and its catalysis action for reaction of butane and pentane[J]. Journal of the Chemical Society,Chemical Communication,1988,18:1259.
[16]蒋平平,李良阔.一种偏苯三酸三(C8-10醇)酯的制备方法:1769260[P].2006-05-10.
[17] HUANG Z X,LIN Y X,LI L. Preparation and shaping of solid acid SO42-/Ti O2and its application for esterification of propylene glycol monomethyl ether and acetic acid[J]. Chinese journal chemical engineering,2017,(25):1207.
[18]于龙,樊其艳,吴文雷,等.固体超强酸SO2-4/Fe2O3催化合成尼泊金丁酯[J].食品工业科技,2012,33(10):300.
[19] CORMA A,GARCA H. Organic reaction catalyzed over solid acids[J].Catalysis today,1997,(38):257.
[20]谢小红.B2O3/WO3-Zr O2的制备及应用[D].兰州:兰州理工大学,2007.
[21]翟德伟,乐英红,华伟明,等.Al2O3掺杂SO2-4/SnO2固体酸催化剂上的酯化和酯交换反应[J].物理化学学报,2010,26(7):1867.
[22] HUANG C C,YANG C J,GAO P J,et al.Characterization of an alkaline earth metal-doped solid superacid and its activity for the esterification of oleic acid with methanol[J]. Green chemistry,2015,17:3609.
[23]杨辉荣,邓鹏飞,宋晓锐,等.固体超强酸SO2-4/Zr O2-Ti O2催化剂的研制及其催化合成草莓酸酯的研究[J].精细化工,2000,17(9):534.
[24]张志宏,薛来奇,祁洪江,等.固体超强酸SO2-4/Ti O2-Fe2O3催化合成乳酸丁酯[J].化学试剂,2000,22(4):231.
[25] TOMINAKA S,MOMMA T,SCROSATI B,et al.Sulfated zirconia as a proton conductor for fuel cells:stability to hydrolysis and influence on catalysts[J].Power sources,2010(195):4065.
[26]宋华,杨东明,李锋,等.SO2-4/MxOy型固体超强酸催化剂的研究进展[J].化工进展,2007,26(2):145.
[27] YU G X,ZHOU X L,LI C L,et al.Esterification over rare earth oxide and alumina promoted SO2-4/Zr O2[J]. Catalysis today,2009,(148):169.
[28]李家贵,朱万仁,陈渊,等.新型稀土铁系固体超强酸的制备和三醋酸甘油酯的催化合成[J].合成化学,2004,12(4):355.
[29] LI Y,ZHANG X D,SUN L,et al.Fatty acid methyl ester synthesis catalyzed by solid superacid catalyst SO2-4/Zr O2-Ti O2/La3+[J].Applied energy,2010,87:156.
[30] WANG J X,PAN H,CHEN L,et al. Synthesis characterization and catalytic properties of S2O82-/x wt%Ce-Al-Fe-O solid acid catalysts in the esterification reaction of acetic acid with n-butanol[J].Reaction kinetics mechanisms catalysis,2014,113:407.
[31]陈建军,孙秀菊,高文艺,等.氧化铝-硫酸固体酸催化剂催化油酸与甲酸酯化反应及其动力学研究[J].油脂化工,2014,39(9):48.
[32]夏金虹.稀土改性SO2-4/Ti O2固体超强酸催化合成肉桂酸正丁酯[J].应用化工,2004,33(3):34.
[33]武永军,王杜娟,王红艳,等.SO2-4/Ti O2-Al2O3催化合成三羟甲基丙烷油酸酯[J].生物化工,2015,1(1):24.
[34]张萍,许保恩,魏青,等.用Si O2负载纳米级SO2-4/Ti O2固体超强酸催化合成柠檬酸三正丁酯[J].化学试剂,2008,30(2):13.
[35]绕蔚兰,潘志权,向守信.稀土固体超强酸的制备及其对硬脂肪酸酯化反应的催化[J].应用化学,2011,28(8):907.
[36]胡春燕,李双全.稀土固体超强酸Gd3+-SO2-4/Zr O2催化合成乙酸正丁酯[J].湿法冶金,2011,30(4):344.
[37] YADAV G D,YADAV R A.Insight into esterification of eugenol to eugenol benzoateusing a solid superacidic modified zirconia catalyst UDCaT-5[J]. Chemical engineering journal,2012,192:146.
[38]任小宁.几种固体酸催化剂催化合成柠檬酸酯的研究[D].兰州:西北师范大学,2011
[39]张小曼.磁性固体超强酸催化合成乳酸丁酯[J].化学世界,2003(3):140.
[40] GUAN D H,FAN M Q,WANG J. Synthesis and properties of magnetic solid superacid:SO2-4/Zr O2-B2O3-Fe3O4[J].Materials chemistry and physics,2010(122):278.
[41]石香玉,王拥军.磁性纳米SO2-4/Fe3O4-Zr O2固体超强酸催化合成己二酸二正辛酯[J].化学工程,2006,34(6):37.
[42]陈丹云,周慧,何建英.固体超强酸SO2-4/SnO2-CeO2-高岭土催化合成乳酸丁酯[J].化学试剂,2010,32(8):735.
[43]潘会,高素云,粟智,等.蒙脱石负载铝基固体酸的制备及其催化性能[J].精细化工,2016,33(6):660.
[44]常癑,应婵娟,任小宁,等.坡缕石负载纳米SO2-4/Ti O2固体超强酸催化合成偏苯三酸三辛酯[J].精细化工,2011,28(7):693.
[45]张海荣,邬国英,林西平.固体酸催化酯化酸化油合成生物柴油的研究[J].石油与天然气化工,2007,36(2):114.
[46]赵立芳,何柱生,马玉英.负载型固体超强酸催化合成富马酸二甲酯[J].宝鸡文理学院学报,2002,22(2):138.
[47]蒋金龙,杨勇,许莹,等.磁性SO2-4/Ti O2/Fe3O4/PAL固体酸催化剂的制备及其催化酯化性能[J].非金属矿,2013,36(4):1.
[48]汤晓君.磁性碳微球负载SO2-4/Ti O2固体酸的制备及催化酯化性能研究[J].高师理科学刊,2016,36(5):32.
[49]郭锡坤,秦国平,谌宁.介孔固体超强酸催化剂的制备与结构表征[J].化学学报,2004,62(2):208.
[2] REDDY B M,PATIL M K.Organic syntheses and transformations catalyzed by sulfated zirconia[J]. Chemical reviews,2009,109(6):2185.
[3] JING H W,WANG X M,LIU Y,et al. Preparation of magnetic nanocomposites of solid acid catalysts and their applicability in esterification[J].Chinese journal of catalysis,2015,36(2):244.
[4]汪颖军,李言,所艳华,等.负载型氧化物固体超强酸改性的研究进展[J].石油学报(石油加工),2012,28(3):525.
[5] NIU Y,LI F Y,YANG K,et al.Preparation and characterization of sulfated Ti O2with rhodium modification used in esterification reaction and decomposition of methyl orange[J].Chinese journal chemical engineering,2016(24):767.
[6]孟瑶,李锋,宋华.SO2-4/MxOy型固体超强酸酸中心结构及其在轻质烷烃异构化反应中的机理研究进展[J].化工进展,2015,34(11):3906.
[7] LI X,HUANG W.Synthesis of biodiesel from rap oil over sulfated titania-based solid superacid catalysts[J]. Energy sources(recovery,utilization,and environmental effects),2009,31(18):1666.
[8] MANTILLA A,FERRAT G,LOPEZ-ORTEGA A,et al.Catalytic behavior of sulfated Ti O2in light olefins oligomerization[J].Journal of molecular catalysis A(chemical),2005,228(1/2):333.
[9] KHDER A S,EL-SHARKWAY E A,El-HAKAM S A,et al.Surface characterization and catalytic activity of sulfated tin oxide catalyst[J].Catalysis communications,2008,9(5):769.
[10]陈宝树,网凶铃,赵久生,等.新型精细化工讲座[J].精细石油化工,1990(5):63.
[11]周晶,聂晓安,戴伟娣.负载型固体酸催化剂制备生物柴油研究进展[J].生物质化学工程,2008,4(1):41.
[12]于世涛,刘福成.固体酸与精细化工[M].北京:化学工业出版社,2006:15-19.
[13]卢冠忠,江娴,王药松.多组元SO2-4/MxOy型固体超强酸催化酯化反应的研究[J].工业催化,1994(2):14.
[14]曾健青,罗庆云,王琴,等.SO2-4/MxOy型固体超强酸的研究进展[J].石油化工,1994,23(3):191.
[15] HINO M,ARATA K. Synthesis of solid super acid of tuugsten oxide supported on zirconia and its catalysis action for reaction of butane and pentane[J]. Journal of the Chemical Society,Chemical Communication,1988,18:1259.
[16]蒋平平,李良阔.一种偏苯三酸三(C8-10醇)酯的制备方法:1769260[P].2006-05-10.
[17] HUANG Z X,LIN Y X,LI L. Preparation and shaping of solid acid SO42-/Ti O2and its application for esterification of propylene glycol monomethyl ether and acetic acid[J]. Chinese journal chemical engineering,2017,(25):1207.
[18]于龙,樊其艳,吴文雷,等.固体超强酸SO2-4/Fe2O3催化合成尼泊金丁酯[J].食品工业科技,2012,33(10):300.
[19] CORMA A,GARCA H. Organic reaction catalyzed over solid acids[J].Catalysis today,1997,(38):257.
[20]谢小红.B2O3/WO3-Zr O2的制备及应用[D].兰州:兰州理工大学,2007.
[21]翟德伟,乐英红,华伟明,等.Al2O3掺杂SO2-4/SnO2固体酸催化剂上的酯化和酯交换反应[J].物理化学学报,2010,26(7):1867.
[22] HUANG C C,YANG C J,GAO P J,et al.Characterization of an alkaline earth metal-doped solid superacid and its activity for the esterification of oleic acid with methanol[J]. Green chemistry,2015,17:3609.
[23]杨辉荣,邓鹏飞,宋晓锐,等.固体超强酸SO2-4/Zr O2-Ti O2催化剂的研制及其催化合成草莓酸酯的研究[J].精细化工,2000,17(9):534.
[24]张志宏,薛来奇,祁洪江,等.固体超强酸SO2-4/Ti O2-Fe2O3催化合成乳酸丁酯[J].化学试剂,2000,22(4):231.
[25] TOMINAKA S,MOMMA T,SCROSATI B,et al.Sulfated zirconia as a proton conductor for fuel cells:stability to hydrolysis and influence on catalysts[J].Power sources,2010(195):4065.
[26]宋华,杨东明,李锋,等.SO2-4/MxOy型固体超强酸催化剂的研究进展[J].化工进展,2007,26(2):145.
[27] YU G X,ZHOU X L,LI C L,et al.Esterification over rare earth oxide and alumina promoted SO2-4/Zr O2[J]. Catalysis today,2009,(148):169.
[28]李家贵,朱万仁,陈渊,等.新型稀土铁系固体超强酸的制备和三醋酸甘油酯的催化合成[J].合成化学,2004,12(4):355.
[29] LI Y,ZHANG X D,SUN L,et al.Fatty acid methyl ester synthesis catalyzed by solid superacid catalyst SO2-4/Zr O2-Ti O2/La3+[J].Applied energy,2010,87:156.
[30] WANG J X,PAN H,CHEN L,et al. Synthesis characterization and catalytic properties of S2O82-/x wt%Ce-Al-Fe-O solid acid catalysts in the esterification reaction of acetic acid with n-butanol[J].Reaction kinetics mechanisms catalysis,2014,113:407.
[31]陈建军,孙秀菊,高文艺,等.氧化铝-硫酸固体酸催化剂催化油酸与甲酸酯化反应及其动力学研究[J].油脂化工,2014,39(9):48.
[32]夏金虹.稀土改性SO2-4/Ti O2固体超强酸催化合成肉桂酸正丁酯[J].应用化工,2004,33(3):34.
[33]武永军,王杜娟,王红艳,等.SO2-4/Ti O2-Al2O3催化合成三羟甲基丙烷油酸酯[J].生物化工,2015,1(1):24.
[34]张萍,许保恩,魏青,等.用Si O2负载纳米级SO2-4/Ti O2固体超强酸催化合成柠檬酸三正丁酯[J].化学试剂,2008,30(2):13.
[35]绕蔚兰,潘志权,向守信.稀土固体超强酸的制备及其对硬脂肪酸酯化反应的催化[J].应用化学,2011,28(8):907.
[36]胡春燕,李双全.稀土固体超强酸Gd3+-SO2-4/Zr O2催化合成乙酸正丁酯[J].湿法冶金,2011,30(4):344.
[37] YADAV G D,YADAV R A.Insight into esterification of eugenol to eugenol benzoateusing a solid superacidic modified zirconia catalyst UDCaT-5[J]. Chemical engineering journal,2012,192:146.
[38]任小宁.几种固体酸催化剂催化合成柠檬酸酯的研究[D].兰州:西北师范大学,2011
[39]张小曼.磁性固体超强酸催化合成乳酸丁酯[J].化学世界,2003(3):140.
[40] GUAN D H,FAN M Q,WANG J. Synthesis and properties of magnetic solid superacid:SO2-4/Zr O2-B2O3-Fe3O4[J].Materials chemistry and physics,2010(122):278.
[41]石香玉,王拥军.磁性纳米SO2-4/Fe3O4-Zr O2固体超强酸催化合成己二酸二正辛酯[J].化学工程,2006,34(6):37.
[42]陈丹云,周慧,何建英.固体超强酸SO2-4/SnO2-CeO2-高岭土催化合成乳酸丁酯[J].化学试剂,2010,32(8):735.
[43]潘会,高素云,粟智,等.蒙脱石负载铝基固体酸的制备及其催化性能[J].精细化工,2016,33(6):660.
[44]常癑,应婵娟,任小宁,等.坡缕石负载纳米SO2-4/Ti O2固体超强酸催化合成偏苯三酸三辛酯[J].精细化工,2011,28(7):693.
[45]张海荣,邬国英,林西平.固体酸催化酯化酸化油合成生物柴油的研究[J].石油与天然气化工,2007,36(2):114.
[46]赵立芳,何柱生,马玉英.负载型固体超强酸催化合成富马酸二甲酯[J].宝鸡文理学院学报,2002,22(2):138.
[47]蒋金龙,杨勇,许莹,等.磁性SO2-4/Ti O2/Fe3O4/PAL固体酸催化剂的制备及其催化酯化性能[J].非金属矿,2013,36(4):1.
[48]汤晓君.磁性碳微球负载SO2-4/Ti O2固体酸的制备及催化酯化性能研究[J].高师理科学刊,2016,36(5):32.
[49]郭锡坤,秦国平,谌宁.介孔固体超强酸催化剂的制备与结构表征[J].化学学报,2004,62(2):208.