酸催化山梨醇脱水制异山梨醇的研究进展
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摘要
异山梨醇是一种生物基功能性二元醇,近年来因其在聚合物工业中的潜在应用价值而备受关注。山梨醇脱水反应是生物质转化合成异山梨醇的关键步骤,目前普遍采用酸催化体系,且在酸性催化剂开发及工艺研究方面均取得了良好进展。本工作主要介绍了已报道的酸性催化剂结构与性质对催化活性及选择性的影响,指出强酸性均相催化剂具有高催化活性,但腐蚀性强,且不易循环利用;多相催化剂催化活性与酸性位点、酸度、酸容量、孔结构、表面性质和结构等都有关系,且这些性质随催化剂组成和结构改变而相互影响。针对目前山梨醇脱水反应催化剂均相催化腐蚀性强、催化剂循环性差,多相催化剂催化活性不高的现状,高催化活性可循环使用的离子液体催化剂是一种具有发展潜力的均相催化剂,对多相催化剂构效关系还应进行更多的研究以指导新型催化剂的开发。
Isosorbide is a biomass-derived functional diol, with wide applications in the synthesis of several pharmaceutical molecules and fine chemicals. It attracted much attention recently due to its potential applications in the polymer industry. The catalytic dehydration of sorbitol represents a key and challenging step in the synthesis of isosorbide from biomass. Up to now, the acid catalytic system has been extensively explored and significant progresses were made with respect to both of catalyst designing and process optimization. This review mainly provides the relationship between structure and activity of different acid catalyst types. The first section comprehensively introduces the acid-catalyzed dehydration of sorbitol to isosorbide and the mechanism involved. The following two sections describe the progresses made in the homogenous and heterogeneous catalysts, respectively. The homogeneous catalyst mainly includes Br?nsted mineral acids, Lewis acids and ionic liquids, and the focus of was put on the influence of acid sites, acidity, stability and reaction solvent to sorbitol dehydration. The heterogeneous catalyst mainly includes acid resin, zeolite, supported metal oxide, heteropolyacid, sulphate and phosphate metal oxides, acid polymer and macromolecule catalyst. In addition to acid sites, acidity and stability, the acid capacity, pore structure, and surface structure and nature also have importantly effects on the activity of heterogeneous catalyst. Moreover, the effects of preparation methods of heterogeneous catalysts on their properties will be discussed. This article pointed out that Br?nsted mineral acids of strong acidity provided better catalytic activity, which, however, had the worst corrodibility and are difficult to be recycled. Latest reported acidic ionic liquids with tunable acidity and non-volatility in principle enables catalyst recycling, which may become competitive catalysts to replace mineral acids. For the heterogeneous catalytic system, the catalytic activity is closely related to the composition and structure of catalysts launched. More researches about the relationship between structure and activity needs to be carried out to develop efficient solid catalyst.
Isosorbide is a biomass-derived functional diol, with wide applications in the synthesis of several pharmaceutical molecules and fine chemicals. It attracted much attention recently due to its potential applications in the polymer industry. The catalytic dehydration of sorbitol represents a key and challenging step in the synthesis of isosorbide from biomass. Up to now, the acid catalytic system has been extensively explored and significant progresses were made with respect to both of catalyst designing and process optimization. This review mainly provides the relationship between structure and activity of different acid catalyst types. The first section comprehensively introduces the acid-catalyzed dehydration of sorbitol to isosorbide and the mechanism involved. The following two sections describe the progresses made in the homogenous and heterogeneous catalysts, respectively. The homogeneous catalyst mainly includes Br?nsted mineral acids, Lewis acids and ionic liquids, and the focus of was put on the influence of acid sites, acidity, stability and reaction solvent to sorbitol dehydration. The heterogeneous catalyst mainly includes acid resin, zeolite, supported metal oxide, heteropolyacid, sulphate and phosphate metal oxides, acid polymer and macromolecule catalyst. In addition to acid sites, acidity and stability, the acid capacity, pore structure, and surface structure and nature also have importantly effects on the activity of heterogeneous catalyst. Moreover, the effects of preparation methods of heterogeneous catalysts on their properties will be discussed. This article pointed out that Br?nsted mineral acids of strong acidity provided better catalytic activity, which, however, had the worst corrodibility and are difficult to be recycled. Latest reported acidic ionic liquids with tunable acidity and non-volatility in principle enables catalyst recycling, which may become competitive catalysts to replace mineral acids. For the heterogeneous catalytic system, the catalytic activity is closely related to the composition and structure of catalysts launched. More researches about the relationship between structure and activity needs to be carried out to develop efficient solid catalyst.
引文
[1]Hockett R C,Fletcher Jr H G,Sheffield E L,et al.Hexitol anhydrides:1.the structure of isosorbide,a crystalline dianhydrosorbitol[J].Journal of the American Chemical Society,1946,68(6):927-930.
[2]Parker J D,Parker J O.Nitrate therapy for stable angina pectoris[J].New England Journal of Medicine,1998,338(8):520-531.
[3]Battegazzore D,Bocchini S,Nicola G,et al.Isosorbide,a green plasticizer for the rmoplastic starch that does not retrogradate[J].Carbohydrate Polymers,2015,119:78-84.
[4]Lavergne A,Zhu Y,Molinier V,et al.Aqueous phase behavior of isosorbide-based non-ionic surfactants[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2012,404:56-62.
[5]Tundo P,AricòF,Gauthier G,et al.Green synthesis of dimethyl isosorbide[J].ChemSusChem,2010,3(5):566-570.
[6]Medem H,Schreckenberg M,Dhein R,et al.Thermoplastic polycarbonates,their preparation and their use as shaped articles and films:US 4506066[P].1985-03-19.
[7]Gohil R M.Properties and strain hardening character of polyethylene terephthalate containing isosorbide[J].Polymer Engineering and Science,2009,49(3):544-553.
[8]Lee C H,Takagi H,Okamoto H,et al.Synthesis,characterization,and properties of polyurethanes containing 1,4,3,6-dianhydro-D-sorbitol[J].Journal of Polymer Science Part A:Polymer Chemistry,2009,47(22):6025-6031.
[9]Steenwijk J,Langerock R,Es D S,et al.Long-term heat stabilisation by(natural)polyols in heavy metal-and zinc-free poly(vinyl chloride)[J].Polymer Degradation and Stability,2006,91(1):52-59.
[10]Dutta S,Pal S.Promises in direct conversion of cellulose and lignocellulosic biomass to chemicals and fuels:combined solventnanocatalysis approach for biorefinary[J].Biomass Bioenergy,2014,62:182-197.
[11]Van Gorp K,Boerman E,Cavenaghi C V,et al.Catalytic hydrogenation of fine chemicals:sorbitol production[J].Catalysis Today,1999,52(2/3):349-361.
[12]Silveira M,Jonas R.The biotechnological production of sorbitol[J].Applied Microbiology and Biotechnology,2002,59(4/5):400-408.
[13]Xiu Y H,Zhu W W,Hou Z S.Recent progress in catalytic selective dehydration of sorbitol[J].Chinese Science Bulletin,2015,60(16):1443-1451.
[14]Dussenne C,Delaunay T,Wiatz V,et al.Synthesis of isosorbide:an overview of challenging reactions[J].Green Chemistry,2017,19(22):5332-5344.
[15]Barker R.Conversion of acyclic carbohydrates to tetrahydrofuran derivatives:acidcatalyzed dehydration of hexitols[J].Journal of Organic Chemistry,1970,35(2):461-464.
[16]Bock K,Pedersen C,Thqgersen H.Acid catalyzed dehydration of alditols:part I[J].Acta Chemica Scandinavica,Series B:Organic Chemistry and Biochemistry,1981,35(6):441-449
[17]Do?en-Mi?ovi?L,?ekovi??.Conformational effects on the mechanism of acidcatalyzed dehydration of hexitols[J].Journal of Physical Organic Chemistry,1998,11(12):887-894.
[18]Dabbawala A A,Mishra D K,Huber G W,et al.Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide[J].Applied Catalysis A:General,2015,492:252-261.
[19]Li J,Buijs W,Berger R J,et al.Sorbitol dehydration in a ZnCl2molten salt hydrate medium:molecular modeling[J].Catalysis Science&Technology,2014,4(1):152-163.
[20]Yabushita M,Kobayashi H,Shrotri A,et al.Sulfuric acid-catalyzed dehydration of sorbitol:mechanistic study on preferential formation of 1,4-sorbitan[J].Bulletin of the Chemical Society of Japan,2015,88(7):996-1002.
[21]Deng J,Xu B H,Wang Y F,et al.Br?nsted acidic ionic liquidcatalyzed dehydrative formation of isosorbide from sorbitol:introduction of a continuous process[J].Catalysis Science&Technology,2017,7(10):2065-2073.
[22]Hartmann L A.Purification of isosorbide:US 3160641[P].1964-12-08.
[23]Kamlesh K B.Integated continuous process for anhydro sugar alcohol manufacture:US 6864378 B2[P].2005-03-08.
[24]Fletcher Jr H G,Goepp Jr R M.Hexitol anhydrides-1,4,3,6-dianhydro-l-iditol and the structures of isomannide and isosorbide[J].Journal of the American Chemical Society,1946,68(6):939-941.
[25]Fleche G,Huchette M.Isosorbide:preparation,properties and chemistry[J].Starch-St?rke,1986,38(1):26-30.
[26]Yamaguchi A,Hiyoshi N,Sato O,et al.Sorbitol dehydration in high temperature liquid water[J].Green Chemisrty,2011,13(4),873-881.
[27]Yamaguchi A,Muramatsu N,Mimura N,et al.Intramolecular dehydration of biomass-derived sugar alcohols in high-temperature water[J].Physical Chemistry Chemical Physics,2017,19(4):2714-2722.
[28]Shirai M,Sato O,Hiyoshi N,et al.Enhancement of reaction rates for catalytic benzaldehyde hydrogenation and sorbitol dehydration in water solvent by addition of carbon dioxide[J].Journal of Chemical Sciences,2014,126(2):395-401.
[29]Duclos A,Fayet C,Gelas J.A simple conversion of polyols into anhydroalditols[J].Synthesis,1994,1994(10):1087-1090.
[30]Li J,Spina A,Moulijn J A,et al.Sorbitol dehydration into isosorbide in a molten salt hydrate medium[J].Catalysis Science&Technology,2013,3(6):1540-1546.
[31]Robinson J M,Wadle A M,Reno M D,et al.Solvent-and microwave-assisted dehydrations of polyols to anhydro and dianhydro polyols[J].Energy Fuels,2015,29(10):6529-6535.
[32]Kamimura A,Murata K,Tanaka Y,et al.Rapid conversion of sorbitol to isosorbide in hydrophobic ionic liquids under microwave irradiation[J].ChemSusChem,2014,7(12):3257-3259.
[33]Tanabe K,H?lderich W F.Industrial application of solid acid-base catalysts[J].Applied Catalysis A:General,1999,181(2):399-434.
[34]Nicewicz D A,MacMillan D W C.Merging photoredox catalysis with organocatalysis:the direct asymmetric alkylation of aldehydes[J].Science,2008,322(5898):77-80.
[35]Sun P,Yu D H,Hu Y,et al.H3PW12O40/SiO2 for sorbitol dehydration to isosorbide:high efficient and reusable solid acid catalyst[J].Korean Journal of Chemical Engineering,2011,28(1):99-105.
[36]Ahmed I,Khan N A,Mishra D K,et al.Liquid-phase dehydration of sorbitol to isosorbide using sulfated titania as a solid acid catalyst[J].Chemical Engineering Science,2013,93:91-95.
[37]Xia J J,Yu D H,Hu Y,et al.Sulfated copper oxide:an efficient catalyst for dehydration of sorbitol to isosorbide[J].Catalysis Communications,2011,12(6):544-547.
[38]Dabbawala A A,Mishra D K,Hwang J S.Sulfated tin oxide as an efficient solid acid catalyst for liquid phase selective dehydration of sorbitol to isosorbide[J].Catalysis Communications,2013,42:1-5.
[39]Rusu O A,Hoelderich W F,Wyart H,et al.Metal phosphate catalyzed dehydration of sorbitol under hydrothermal conditions[J].Applied Catalysis B:Environmental,2015,176:139-149.
[40]Gu M,Yu D,Zhang H,et al.Metal(IV)phosphates as solid catalysts for selective dehydration of sorbitol to isosorbide[J].Catalysis Letters,2009,133(1/2):214-220.
[41]Cao D,Yu B,Zhang S,et al.Isosorbide production from sorbitol over porous zirconium phosphate catalyst[J].Applied Catalysis A:General,2016,528:59-66.
[42]Zhang X,Yu D,Zhao J,et al.The effect of P/Ta ratio on sorbitol dehydration over modified tantalum oxide by phosphoric acid[J].Catalysis Communications,2014,43:29-33.
[43]Tang Z C,Yu D H,Sun P,et al.Phosphoric acid modified Nb2O5catalyst for dehydration of sorbitol to isosorbide[J].Bulletin of the Korean Chemical Society,2010,31(12):3679-3683.
[44]Khan N A,Mishra D K,Ahmed I,et al.Liquid-phase dehydration of sorbitol to isosorbide using sulfated zirconia as a solid acid catalyst[J].Applied Catalysis A:General,2013,452:34-38.
[45]Dabbawala A A,Park J J,Valekar A H,et al.Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide[J].Catalysis Communications,2015,69:207-211.
[46]Zhang J,Wang L,Liu F,et al.Enhanced catalytic performance in dehydration of sorbitol to isosorbide over a superhydrophobic mesoporous acid catalyst[J].Catalysis Today,2015,242:249-254.
[47]Kobayashi H,Yokoyama H,Feng B,et al.Dehydration of sorbitol to isosorbide over H-beta zeolites with high Si/Al ratios[J].Green Chemistry,2015,17(5):2732-2735.
[48]Xiu Y,Chen A,Liu X,et al.Selective dehydration of sorbitol to 1,4-anhydro-D-sorbitol catalyzed by a polymer-supported acid catalyst[J].RSC Advances,2015,5(36):28233-28241.
[49]Shi J,Shan Y,Tian Y,et al.Hydrophilic sulfonic acid-functionalized micro-bead silica for dehydration of sorbitol to isosorbide[J].RSCAdvances,2016,6(16):13514-13521.
[50]Thombal R S,Jadhav V H.Application of glucose derived magnetic solid acid for etherification of 5-HMF to 5-EMF,dehydration of sorbitol to isosorbide,and esterification of fatty acids[J].Tetrahedron Letters,2016,57(39):4398-4400.
[51]Kamimura A,Murata K,Kawamoto T.An efficient and selective conversion of sorbitol in ionic liquids:use of ion exchange resin as a solid acid catalyst[J].Tetrahedron Letters,2017,58(37):3616-3618.
[52]Che P,Lu F,Si X,et al.A strategy of ketalization for the catalytic selective dehydration of biomass-based polyols over H-beta zeolite[J].Green Chemistry,2018,20:634-640.
[53]Polaert I,Felix M C,Fornasero M,et al.A greener process for isosorbide production:Kinetic study of the catalytic dehydration of pure sorbitol under microwave[J].Chemical Engineering Journal,2013,222:228-239.
[54]Otomo R,Yokoi T,Tatsumi T.Synthesis of isosorbide from sorbitol in water over high-silica aluminosilicate zeolites[J].Applied Catalysis A:General,2015,505:28-35.
[55]Morita Y,Furusato S,Takagaki A,et al.Intercalation-controlled cyclodehydration of sorbitol in water over layered-niobiummolybdate solid acid[J].ChemSusChem,2014,7(3):748-752.
[56]Zou J,Cao D,Tao W,et al.Sorbitol dehydration into isosorbide over a cellulose-derived solid acid catalyst[J].RSC Advances,2016,6(55):49528-49536.
[57]Morales G,Iglesias J,Melero J A,et al.Isosorbide production from sorbitol over heterogeneous acid catalysts:screening and kinetic study[J].Topics in Catalysis,2017,60(15/16):1027-1039.
[58]Ginés-Molina M J,Moreno-Tost R,Santamaría-González J,et al.Dehydration of sorbitol to isosorbide over sulfonic acid resins under solvent-free conditions[J].Applied Catalysis A:General,2017,537:66-73.
[2]Parker J D,Parker J O.Nitrate therapy for stable angina pectoris[J].New England Journal of Medicine,1998,338(8):520-531.
[3]Battegazzore D,Bocchini S,Nicola G,et al.Isosorbide,a green plasticizer for the rmoplastic starch that does not retrogradate[J].Carbohydrate Polymers,2015,119:78-84.
[4]Lavergne A,Zhu Y,Molinier V,et al.Aqueous phase behavior of isosorbide-based non-ionic surfactants[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2012,404:56-62.
[5]Tundo P,AricòF,Gauthier G,et al.Green synthesis of dimethyl isosorbide[J].ChemSusChem,2010,3(5):566-570.
[6]Medem H,Schreckenberg M,Dhein R,et al.Thermoplastic polycarbonates,their preparation and their use as shaped articles and films:US 4506066[P].1985-03-19.
[7]Gohil R M.Properties and strain hardening character of polyethylene terephthalate containing isosorbide[J].Polymer Engineering and Science,2009,49(3):544-553.
[8]Lee C H,Takagi H,Okamoto H,et al.Synthesis,characterization,and properties of polyurethanes containing 1,4,3,6-dianhydro-D-sorbitol[J].Journal of Polymer Science Part A:Polymer Chemistry,2009,47(22):6025-6031.
[9]Steenwijk J,Langerock R,Es D S,et al.Long-term heat stabilisation by(natural)polyols in heavy metal-and zinc-free poly(vinyl chloride)[J].Polymer Degradation and Stability,2006,91(1):52-59.
[10]Dutta S,Pal S.Promises in direct conversion of cellulose and lignocellulosic biomass to chemicals and fuels:combined solventnanocatalysis approach for biorefinary[J].Biomass Bioenergy,2014,62:182-197.
[11]Van Gorp K,Boerman E,Cavenaghi C V,et al.Catalytic hydrogenation of fine chemicals:sorbitol production[J].Catalysis Today,1999,52(2/3):349-361.
[12]Silveira M,Jonas R.The biotechnological production of sorbitol[J].Applied Microbiology and Biotechnology,2002,59(4/5):400-408.
[13]Xiu Y H,Zhu W W,Hou Z S.Recent progress in catalytic selective dehydration of sorbitol[J].Chinese Science Bulletin,2015,60(16):1443-1451.
[14]Dussenne C,Delaunay T,Wiatz V,et al.Synthesis of isosorbide:an overview of challenging reactions[J].Green Chemistry,2017,19(22):5332-5344.
[15]Barker R.Conversion of acyclic carbohydrates to tetrahydrofuran derivatives:acidcatalyzed dehydration of hexitols[J].Journal of Organic Chemistry,1970,35(2):461-464.
[16]Bock K,Pedersen C,Thqgersen H.Acid catalyzed dehydration of alditols:part I[J].Acta Chemica Scandinavica,Series B:Organic Chemistry and Biochemistry,1981,35(6):441-449
[17]Do?en-Mi?ovi?L,?ekovi??.Conformational effects on the mechanism of acidcatalyzed dehydration of hexitols[J].Journal of Physical Organic Chemistry,1998,11(12):887-894.
[18]Dabbawala A A,Mishra D K,Huber G W,et al.Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide[J].Applied Catalysis A:General,2015,492:252-261.
[19]Li J,Buijs W,Berger R J,et al.Sorbitol dehydration in a ZnCl2molten salt hydrate medium:molecular modeling[J].Catalysis Science&Technology,2014,4(1):152-163.
[20]Yabushita M,Kobayashi H,Shrotri A,et al.Sulfuric acid-catalyzed dehydration of sorbitol:mechanistic study on preferential formation of 1,4-sorbitan[J].Bulletin of the Chemical Society of Japan,2015,88(7):996-1002.
[21]Deng J,Xu B H,Wang Y F,et al.Br?nsted acidic ionic liquidcatalyzed dehydrative formation of isosorbide from sorbitol:introduction of a continuous process[J].Catalysis Science&Technology,2017,7(10):2065-2073.
[22]Hartmann L A.Purification of isosorbide:US 3160641[P].1964-12-08.
[23]Kamlesh K B.Integated continuous process for anhydro sugar alcohol manufacture:US 6864378 B2[P].2005-03-08.
[24]Fletcher Jr H G,Goepp Jr R M.Hexitol anhydrides-1,4,3,6-dianhydro-l-iditol and the structures of isomannide and isosorbide[J].Journal of the American Chemical Society,1946,68(6):939-941.
[25]Fleche G,Huchette M.Isosorbide:preparation,properties and chemistry[J].Starch-St?rke,1986,38(1):26-30.
[26]Yamaguchi A,Hiyoshi N,Sato O,et al.Sorbitol dehydration in high temperature liquid water[J].Green Chemisrty,2011,13(4),873-881.
[27]Yamaguchi A,Muramatsu N,Mimura N,et al.Intramolecular dehydration of biomass-derived sugar alcohols in high-temperature water[J].Physical Chemistry Chemical Physics,2017,19(4):2714-2722.
[28]Shirai M,Sato O,Hiyoshi N,et al.Enhancement of reaction rates for catalytic benzaldehyde hydrogenation and sorbitol dehydration in water solvent by addition of carbon dioxide[J].Journal of Chemical Sciences,2014,126(2):395-401.
[29]Duclos A,Fayet C,Gelas J.A simple conversion of polyols into anhydroalditols[J].Synthesis,1994,1994(10):1087-1090.
[30]Li J,Spina A,Moulijn J A,et al.Sorbitol dehydration into isosorbide in a molten salt hydrate medium[J].Catalysis Science&Technology,2013,3(6):1540-1546.
[31]Robinson J M,Wadle A M,Reno M D,et al.Solvent-and microwave-assisted dehydrations of polyols to anhydro and dianhydro polyols[J].Energy Fuels,2015,29(10):6529-6535.
[32]Kamimura A,Murata K,Tanaka Y,et al.Rapid conversion of sorbitol to isosorbide in hydrophobic ionic liquids under microwave irradiation[J].ChemSusChem,2014,7(12):3257-3259.
[33]Tanabe K,H?lderich W F.Industrial application of solid acid-base catalysts[J].Applied Catalysis A:General,1999,181(2):399-434.
[34]Nicewicz D A,MacMillan D W C.Merging photoredox catalysis with organocatalysis:the direct asymmetric alkylation of aldehydes[J].Science,2008,322(5898):77-80.
[35]Sun P,Yu D H,Hu Y,et al.H3PW12O40/SiO2 for sorbitol dehydration to isosorbide:high efficient and reusable solid acid catalyst[J].Korean Journal of Chemical Engineering,2011,28(1):99-105.
[36]Ahmed I,Khan N A,Mishra D K,et al.Liquid-phase dehydration of sorbitol to isosorbide using sulfated titania as a solid acid catalyst[J].Chemical Engineering Science,2013,93:91-95.
[37]Xia J J,Yu D H,Hu Y,et al.Sulfated copper oxide:an efficient catalyst for dehydration of sorbitol to isosorbide[J].Catalysis Communications,2011,12(6):544-547.
[38]Dabbawala A A,Mishra D K,Hwang J S.Sulfated tin oxide as an efficient solid acid catalyst for liquid phase selective dehydration of sorbitol to isosorbide[J].Catalysis Communications,2013,42:1-5.
[39]Rusu O A,Hoelderich W F,Wyart H,et al.Metal phosphate catalyzed dehydration of sorbitol under hydrothermal conditions[J].Applied Catalysis B:Environmental,2015,176:139-149.
[40]Gu M,Yu D,Zhang H,et al.Metal(IV)phosphates as solid catalysts for selective dehydration of sorbitol to isosorbide[J].Catalysis Letters,2009,133(1/2):214-220.
[41]Cao D,Yu B,Zhang S,et al.Isosorbide production from sorbitol over porous zirconium phosphate catalyst[J].Applied Catalysis A:General,2016,528:59-66.
[42]Zhang X,Yu D,Zhao J,et al.The effect of P/Ta ratio on sorbitol dehydration over modified tantalum oxide by phosphoric acid[J].Catalysis Communications,2014,43:29-33.
[43]Tang Z C,Yu D H,Sun P,et al.Phosphoric acid modified Nb2O5catalyst for dehydration of sorbitol to isosorbide[J].Bulletin of the Korean Chemical Society,2010,31(12):3679-3683.
[44]Khan N A,Mishra D K,Ahmed I,et al.Liquid-phase dehydration of sorbitol to isosorbide using sulfated zirconia as a solid acid catalyst[J].Applied Catalysis A:General,2013,452:34-38.
[45]Dabbawala A A,Park J J,Valekar A H,et al.Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide[J].Catalysis Communications,2015,69:207-211.
[46]Zhang J,Wang L,Liu F,et al.Enhanced catalytic performance in dehydration of sorbitol to isosorbide over a superhydrophobic mesoporous acid catalyst[J].Catalysis Today,2015,242:249-254.
[47]Kobayashi H,Yokoyama H,Feng B,et al.Dehydration of sorbitol to isosorbide over H-beta zeolites with high Si/Al ratios[J].Green Chemistry,2015,17(5):2732-2735.
[48]Xiu Y,Chen A,Liu X,et al.Selective dehydration of sorbitol to 1,4-anhydro-D-sorbitol catalyzed by a polymer-supported acid catalyst[J].RSC Advances,2015,5(36):28233-28241.
[49]Shi J,Shan Y,Tian Y,et al.Hydrophilic sulfonic acid-functionalized micro-bead silica for dehydration of sorbitol to isosorbide[J].RSCAdvances,2016,6(16):13514-13521.
[50]Thombal R S,Jadhav V H.Application of glucose derived magnetic solid acid for etherification of 5-HMF to 5-EMF,dehydration of sorbitol to isosorbide,and esterification of fatty acids[J].Tetrahedron Letters,2016,57(39):4398-4400.
[51]Kamimura A,Murata K,Kawamoto T.An efficient and selective conversion of sorbitol in ionic liquids:use of ion exchange resin as a solid acid catalyst[J].Tetrahedron Letters,2017,58(37):3616-3618.
[52]Che P,Lu F,Si X,et al.A strategy of ketalization for the catalytic selective dehydration of biomass-based polyols over H-beta zeolite[J].Green Chemistry,2018,20:634-640.
[53]Polaert I,Felix M C,Fornasero M,et al.A greener process for isosorbide production:Kinetic study of the catalytic dehydration of pure sorbitol under microwave[J].Chemical Engineering Journal,2013,222:228-239.
[54]Otomo R,Yokoi T,Tatsumi T.Synthesis of isosorbide from sorbitol in water over high-silica aluminosilicate zeolites[J].Applied Catalysis A:General,2015,505:28-35.
[55]Morita Y,Furusato S,Takagaki A,et al.Intercalation-controlled cyclodehydration of sorbitol in water over layered-niobiummolybdate solid acid[J].ChemSusChem,2014,7(3):748-752.
[56]Zou J,Cao D,Tao W,et al.Sorbitol dehydration into isosorbide over a cellulose-derived solid acid catalyst[J].RSC Advances,2016,6(55):49528-49536.
[57]Morales G,Iglesias J,Melero J A,et al.Isosorbide production from sorbitol over heterogeneous acid catalysts:screening and kinetic study[J].Topics in Catalysis,2017,60(15/16):1027-1039.
[58]Ginés-Molina M J,Moreno-Tost R,Santamaría-González J,et al.Dehydration of sorbitol to isosorbide over sulfonic acid resins under solvent-free conditions[J].Applied Catalysis A:General,2017,537:66-73.