Glucose-derived solid acids and their stability enhancement for upgrading biodiesel via esterification
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摘要
Utilization of biomass-derived materials or chemicals plays a significant role in reducing the dependence of unsustainable resources of petroleum and coal. A series of sulfonated glucose-derived solid acids(SGSAs) were developed in this study through a one-step method. These catalysts were characterized by XRD, FT-IR, SEM,and BET to determine their physiochemical properties, and their acid content was measured by acid–base titration. The catalytic performances of SGSA catalysts were evaluated in two esterification reactions: propionic acid or oleic acid with methanol(a typical reaction to upgrade biodiesel). Conversion of oleic acid and selectivity of methyl oleate can reach as high as 93.3% and 94.7% respectively over SGSA-6, which has the highest -SO_3 H density. Moreover, regeneration of spent catalysts by sulfuric acid solution can significantly enhance their stability and reusability.
Utilization of biomass-derived materials or chemicals plays a significant role in reducing the dependence of unsustainable resources of petroleum and coal. A series of sulfonated glucose-derived solid acids(SGSAs) were developed in this study through a one-step method. These catalysts were characterized by XRD, FT-IR, SEM,and BET to determine their physiochemical properties, and their acid content was measured by acid–base titration. The catalytic performances of SGSA catalysts were evaluated in two esterification reactions: propionic acid or oleic acid with methanol(a typical reaction to upgrade biodiesel). Conversion of oleic acid and selectivity of methyl oleate can reach as high as 93.3% and 94.7% respectively over SGSA-6, which has the highest -SO_3 H density. Moreover, regeneration of spent catalysts by sulfuric acid solution can significantly enhance their stability and reusability.
Utilization of biomass-derived materials or chemicals plays a significant role in reducing the dependence of unsustainable resources of petroleum and coal. A series of sulfonated glucose-derived solid acids(SGSAs) were developed in this study through a one-step method. These catalysts were characterized by XRD, FT-IR, SEM,and BET to determine their physiochemical properties, and their acid content was measured by acid–base titration. The catalytic performances of SGSA catalysts were evaluated in two esterification reactions: propionic acid or oleic acid with methanol(a typical reaction to upgrade biodiesel). Conversion of oleic acid and selectivity of methyl oleate can reach as high as 93.3% and 94.7% respectively over SGSA-6, which has the highest -SO_3 H density. Moreover, regeneration of spent catalysts by sulfuric acid solution can significantly enhance their stability and reusability.
引文
[1]D.Chen,X.Zhang,A.F.Lee,Synthetic strategies to nanostructured photocatalysts for CO2reduction to solar fuels and chemicals,J.Mater.Chem.A 3(2015)14487-14516.
[2]A.M.Beale,F.Gao,I.Lezcano-Gonzalez,C.H.F.Peden,J.Szanyi,Recent advances in automotive catalysis for NOxemission control by small-pore microporous materials,Chem.Soc.Rev.44(2015)7371-7405.
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[5]Y.Shi,E.Xing,K.Wu,J.Wang,M.Yang,Y.Wu,Recent progress on upgrading of biooil to hydrocarbons over metal/zeolite bifunctional catalysts,Catal.Sci.Technol.7(2017)2385-2415.
[6]B.Liu,Z.Zhang,Catalytic conversion of biomass into chemicals and fuels over magnetic catalysts,ACS Catal.6(2016)326-338.
[7]B.Chang,Y.Guo,H.Yin,S.Zhang,B.Yang,Synthesis of sulfonated porous carbon nanospheres solid acid by a facile chemical activation route,J.Solid State Chem.221(2015)384-390.
[8]W.Y.Lou,M.H.Zong,Z.Q.Duan,Efficient production of biodiesel from high free fatty acid-containing waste oils using various carbohydrate-derived solid acid catalysts,Bioresour.Technol.99(2008)8752-8758.
[9]A.P.S.Chouhan,A.K.Sarma,Modern heterogeneous catalysts for biodiesel production:A comprehensive review,Renew.Sust.Energ.Rev.15(2011)4378-4399.
[10]Y.Liu,Y.Fang,X.Lu,Z.Wei,X.Li,Hydrogenation of nitrobenzene to p-aminophenol using Pt/C catalyst and carbon-based solid acid,Chem.Eng.J.229(2013)105-110.
[11]X.Zhang,L.J.Durndell,M.A.Isaacs,C.M.A.Parlett,A.F.Lee,K.Wilson,Platinumcatalyzed aqueous-phase hydrogenation of D-glucose to D-sorbitol,ACS Catal.6(2016)7409-7417.
[12]X.Zhang,X.Ke,Z.Zheng,H.Liu,H.Zhu,TiO2nanofibers of different crystal phases for transesterification of alcohols with dimethyl carbonate,Appl.Catal.B Environ.150(2014)330-337.
[13]H.Liu,J.Chen,L.Chen,Y.Xu,X.Guo,D.Fang,Carbon nanotube-based solid sulfonic acids as catalysts for production of fatty acid methyl ester via transesterification and esterification,ACS Sustain.Chem.Eng.4(2016)3140-3150.
[14]H.Guo,X.Qi,L.Li,R.L.Smith Jr.,Hydrolysis of cellulose over functionalized glucosederived carbon catalyst in ionic liquid,Bioresour.Technol.116(2012)355-359.
[15]M.Liu,S.Jia,Y.Gong,C.Song,X.Guo,Effective hydrolysis of cellulose into glucose over sulfonated sugar-derived carbon in an ionic liquid,Ind.Eng.Chem.Res.52(2013)8167-8173.
[16]F.Guo,Z.Fang,T.-J.Zhou,Conversion of fructose and glucose into 5-hydroxymethylfurfural with lignin-derived carbonaceous catalyst under microwave irradiation in dimethyl sulfoxide-ionic liquid mixtures,Bioresour.Technol.112(2012)313-318.
[17]X.Zhang,K.Wilson,A.F.Lee,Heterogeneously catalyzed hydrothermal processing of C-5-C-6 sugars,Chem.Rev.116(2016)12328-12368.
[18]M.Sevilla,A.B.Fuertes,The production of carbon materials by hydrothermal carbonization of cellulose,Carbon 47(2009)2281-2289.
[19]W.J.Liu,H.Jiang,H.Q.Yu,Development of biochar-based functional materials:toward a sustainable platform carbon material,Chem.Rev.115(2015)12251-12285.
[20]J.T.Yu,A.M.Dehkhoda,N.Ellis,Development of biochar-based catalyst for transesterification of canola oil,Energy Fuel 25(2011)337-344.
[21]X.Mo,E.Lotero,C.Lu,Y.Liu,J.G.Goodwin,A novel sulfonated carbon composite solid acid catalyst for biodiesel synthesis,Catal.Lett.123(2008)1-6.
[22]L.Hu,G.Zhao,X.Tang,Z.Wu,J.Xu,L.Lin,S.Liu,Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural over cellulose-derived carbonaceous catalyst in ionic liquid,Bioresour.Technol.148(2013)501-507.
[23]Z.Xu,W.Li,Z.Du,H.Wu,H.Jameel,H.M.Chang,L.Ma,Conversion of corn stalk into furfural using a novel heterogeneous strong acid catalyst in gamma-valerolactone,Bioresour.Technol.198(2015)764-771.
[24]J.Wang,W.Xu,J.Ren,X.Liu,G.Lu,Y.Wang,Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid,Green Chem.13(2011)2678-2681.
[25]B.Zhang,J.Ren,X.Liu,Y.Guo,Y.Guo,G.Lu,Y.Wang,Novel sulfonated carbonaceous materials from p-toluenesulfonic acid/glucose as a high-performance solid-acid catalyst,Catal.Commun.11(2010)629-632.
[26]T.Liu,Z.Li,W.Li,C.Shi,Y.Wang,Preparation and characterization of biomass carbon-based solid acid catalyst for the esterification of oleic acid with methanol,Bioresour.Technol.133(2013)618-621.
[27]M.Hara,T.Yoshida,A.Takagaki,T.Takata,J.N.Kondo,S.Hayashi,K.Domen,A carbon material as a strong protonic acid,Angew.Chem.Int.Ed.43(2004)2955-2958.
[28]M.Okamura,A.Takagaki,M.Toda,J.N.Kondo,K.Domen,T.Tatsumi,M.Hara,S.Hayashi,Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon,Chem.Mater.18(2006)3039-3045.
[29]H.Yan,Y.Yang,D.Tong,X.Xiang,C.Hu,Catalytic conversion of glucose to5-hydroxymethylfurfural over SO42-/ZrO2and SO42-/ZrO2-Al2O3solid acid catalysts,Catal.Commun.10(2009)1558-1563.
[30]J.Zhao,C.Zhou,C.He,Y.Dai,X.Jia,Y.Yang,Efficient dehydration of fructose to 5-hydroxymethylfurfural over sulfonated carbon sphere solid acid catalysts,Catal.Today 264(2016)123-130.
[31]Q.Shu,J.Gao,Z.Nawaz,Y.Liao,D.Wang,J.Wang,Synthesis of biodiesel from waste vegetable oil with large amounts of free fatty acids using a carbon-based solid acid catalyst,Appl.Energy 87(2010)2589-2596.
[32]H.Yu,S.Niu,C.Lu,J.Li,Y.Yang,Sulfonated coal-based solid acid catalyst synthesis and esterification intensification under ultrasound irradiation,Fuel 208(2017)101-110.
[33]L.M.Correia,N.d.S.Campelo,D.S.Novaes,C.L.Cavalcante Jr.,J.Antonio Cecilia,E.Rodriguez-Castellon,R.S.Vieira,Characterization and application of dolomite as catalytic precursor for canola and sunflower oils for biodiesel production,Chem.Eng.J.269(2015)35-43.
[34]L.H.Chin,A.Z.Abdullah,B.H.Hameed,Sugar cane bagasse as solid catalyst for synthesis of methyl esters from palm fatty acid distillate,Chem.Eng.J.183(2012)104-107.
[35]L.Roldan,E.Pires,J.M.Fraile,E.Garcia-Bordeje,Impact of sulfonated hydrothermal carbon texture and surface chemistry on its catalytic performance in esterification reaction,Catal.Today 249(2015)153-160.
[36]J.M.Fraile,E.Garcia-Bordeje,L.Roldan,Deactivation of sulfonated hydrothermal carbons in the presence of alcohols:evidences for sulfonic esters formation,J.Catal.289(2012)73-79.
[37]J.Zhang,J.Chen,Modified solid acids derived from biomass based cellulose for onestep conversion of carbohydrates into ethyl levulinate,J.Energy Chem.25(2016)747-753.
[38]K.Malins,J.Brinks,V.Kampars,I.Malina,Esterification of rapeseed oil fatty acids using a carbon-based heterogeneous acid catalyst derived from cellulose,Appl.Catal.A Gen.519(2016)99-106.
[2]A.M.Beale,F.Gao,I.Lezcano-Gonzalez,C.H.F.Peden,J.Szanyi,Recent advances in automotive catalysis for NOxemission control by small-pore microporous materials,Chem.Soc.Rev.44(2015)7371-7405.
[3]P.N.R.Vennestrom,C.M.Osmundsen,C.H.Christensen,E.Taarning,Beyond petrochemicals:The renewable chemicals industry,Angew.Chem.Int.Ed.50(2011)10502-10509.
[4]L.M.Gilbertson,J.B.Zimmerman,D.L.Plata,J.E.Hutchison,P.T.Anastas,Designing nanomaterials to maximize performance and minimize undesirable implications guided by the Principles of Green Chemistry,Chem.Soc.Rev.44(2015)5758-5777.
[5]Y.Shi,E.Xing,K.Wu,J.Wang,M.Yang,Y.Wu,Recent progress on upgrading of biooil to hydrocarbons over metal/zeolite bifunctional catalysts,Catal.Sci.Technol.7(2017)2385-2415.
[6]B.Liu,Z.Zhang,Catalytic conversion of biomass into chemicals and fuels over magnetic catalysts,ACS Catal.6(2016)326-338.
[7]B.Chang,Y.Guo,H.Yin,S.Zhang,B.Yang,Synthesis of sulfonated porous carbon nanospheres solid acid by a facile chemical activation route,J.Solid State Chem.221(2015)384-390.
[8]W.Y.Lou,M.H.Zong,Z.Q.Duan,Efficient production of biodiesel from high free fatty acid-containing waste oils using various carbohydrate-derived solid acid catalysts,Bioresour.Technol.99(2008)8752-8758.
[9]A.P.S.Chouhan,A.K.Sarma,Modern heterogeneous catalysts for biodiesel production:A comprehensive review,Renew.Sust.Energ.Rev.15(2011)4378-4399.
[10]Y.Liu,Y.Fang,X.Lu,Z.Wei,X.Li,Hydrogenation of nitrobenzene to p-aminophenol using Pt/C catalyst and carbon-based solid acid,Chem.Eng.J.229(2013)105-110.
[11]X.Zhang,L.J.Durndell,M.A.Isaacs,C.M.A.Parlett,A.F.Lee,K.Wilson,Platinumcatalyzed aqueous-phase hydrogenation of D-glucose to D-sorbitol,ACS Catal.6(2016)7409-7417.
[12]X.Zhang,X.Ke,Z.Zheng,H.Liu,H.Zhu,TiO2nanofibers of different crystal phases for transesterification of alcohols with dimethyl carbonate,Appl.Catal.B Environ.150(2014)330-337.
[13]H.Liu,J.Chen,L.Chen,Y.Xu,X.Guo,D.Fang,Carbon nanotube-based solid sulfonic acids as catalysts for production of fatty acid methyl ester via transesterification and esterification,ACS Sustain.Chem.Eng.4(2016)3140-3150.
[14]H.Guo,X.Qi,L.Li,R.L.Smith Jr.,Hydrolysis of cellulose over functionalized glucosederived carbon catalyst in ionic liquid,Bioresour.Technol.116(2012)355-359.
[15]M.Liu,S.Jia,Y.Gong,C.Song,X.Guo,Effective hydrolysis of cellulose into glucose over sulfonated sugar-derived carbon in an ionic liquid,Ind.Eng.Chem.Res.52(2013)8167-8173.
[16]F.Guo,Z.Fang,T.-J.Zhou,Conversion of fructose and glucose into 5-hydroxymethylfurfural with lignin-derived carbonaceous catalyst under microwave irradiation in dimethyl sulfoxide-ionic liquid mixtures,Bioresour.Technol.112(2012)313-318.
[17]X.Zhang,K.Wilson,A.F.Lee,Heterogeneously catalyzed hydrothermal processing of C-5-C-6 sugars,Chem.Rev.116(2016)12328-12368.
[18]M.Sevilla,A.B.Fuertes,The production of carbon materials by hydrothermal carbonization of cellulose,Carbon 47(2009)2281-2289.
[19]W.J.Liu,H.Jiang,H.Q.Yu,Development of biochar-based functional materials:toward a sustainable platform carbon material,Chem.Rev.115(2015)12251-12285.
[20]J.T.Yu,A.M.Dehkhoda,N.Ellis,Development of biochar-based catalyst for transesterification of canola oil,Energy Fuel 25(2011)337-344.
[21]X.Mo,E.Lotero,C.Lu,Y.Liu,J.G.Goodwin,A novel sulfonated carbon composite solid acid catalyst for biodiesel synthesis,Catal.Lett.123(2008)1-6.
[22]L.Hu,G.Zhao,X.Tang,Z.Wu,J.Xu,L.Lin,S.Liu,Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural over cellulose-derived carbonaceous catalyst in ionic liquid,Bioresour.Technol.148(2013)501-507.
[23]Z.Xu,W.Li,Z.Du,H.Wu,H.Jameel,H.M.Chang,L.Ma,Conversion of corn stalk into furfural using a novel heterogeneous strong acid catalyst in gamma-valerolactone,Bioresour.Technol.198(2015)764-771.
[24]J.Wang,W.Xu,J.Ren,X.Liu,G.Lu,Y.Wang,Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid,Green Chem.13(2011)2678-2681.
[25]B.Zhang,J.Ren,X.Liu,Y.Guo,Y.Guo,G.Lu,Y.Wang,Novel sulfonated carbonaceous materials from p-toluenesulfonic acid/glucose as a high-performance solid-acid catalyst,Catal.Commun.11(2010)629-632.
[26]T.Liu,Z.Li,W.Li,C.Shi,Y.Wang,Preparation and characterization of biomass carbon-based solid acid catalyst for the esterification of oleic acid with methanol,Bioresour.Technol.133(2013)618-621.
[27]M.Hara,T.Yoshida,A.Takagaki,T.Takata,J.N.Kondo,S.Hayashi,K.Domen,A carbon material as a strong protonic acid,Angew.Chem.Int.Ed.43(2004)2955-2958.
[28]M.Okamura,A.Takagaki,M.Toda,J.N.Kondo,K.Domen,T.Tatsumi,M.Hara,S.Hayashi,Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon,Chem.Mater.18(2006)3039-3045.
[29]H.Yan,Y.Yang,D.Tong,X.Xiang,C.Hu,Catalytic conversion of glucose to5-hydroxymethylfurfural over SO42-/ZrO2and SO42-/ZrO2-Al2O3solid acid catalysts,Catal.Commun.10(2009)1558-1563.
[30]J.Zhao,C.Zhou,C.He,Y.Dai,X.Jia,Y.Yang,Efficient dehydration of fructose to 5-hydroxymethylfurfural over sulfonated carbon sphere solid acid catalysts,Catal.Today 264(2016)123-130.
[31]Q.Shu,J.Gao,Z.Nawaz,Y.Liao,D.Wang,J.Wang,Synthesis of biodiesel from waste vegetable oil with large amounts of free fatty acids using a carbon-based solid acid catalyst,Appl.Energy 87(2010)2589-2596.
[32]H.Yu,S.Niu,C.Lu,J.Li,Y.Yang,Sulfonated coal-based solid acid catalyst synthesis and esterification intensification under ultrasound irradiation,Fuel 208(2017)101-110.
[33]L.M.Correia,N.d.S.Campelo,D.S.Novaes,C.L.Cavalcante Jr.,J.Antonio Cecilia,E.Rodriguez-Castellon,R.S.Vieira,Characterization and application of dolomite as catalytic precursor for canola and sunflower oils for biodiesel production,Chem.Eng.J.269(2015)35-43.
[34]L.H.Chin,A.Z.Abdullah,B.H.Hameed,Sugar cane bagasse as solid catalyst for synthesis of methyl esters from palm fatty acid distillate,Chem.Eng.J.183(2012)104-107.
[35]L.Roldan,E.Pires,J.M.Fraile,E.Garcia-Bordeje,Impact of sulfonated hydrothermal carbon texture and surface chemistry on its catalytic performance in esterification reaction,Catal.Today 249(2015)153-160.
[36]J.M.Fraile,E.Garcia-Bordeje,L.Roldan,Deactivation of sulfonated hydrothermal carbons in the presence of alcohols:evidences for sulfonic esters formation,J.Catal.289(2012)73-79.
[37]J.Zhang,J.Chen,Modified solid acids derived from biomass based cellulose for onestep conversion of carbohydrates into ethyl levulinate,J.Energy Chem.25(2016)747-753.
[38]K.Malins,J.Brinks,V.Kampars,I.Malina,Esterification of rapeseed oil fatty acids using a carbon-based heterogeneous acid catalyst derived from cellulose,Appl.Catal.A Gen.519(2016)99-106.