Selective synthesis of triacetin from glycerol catalyzed by HZSM-5/MCM-41 micro/mesoporous molecular sieve
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摘要
HZSM-5/MCM-41 molecular sieve(H-ZM) catalysts with well-defined micro/mesoporous structures were synthesized and showed high performance for selective synthesis of triacetin via the esterification reaction of glycerol with acetic acid. The conversion of glycerol was demonstrated to be 100% and the triacetin selectivity was over 91%, which can be attributed to the synergistic effect regarding suitable acidic property, excellent diffusion efficiency and good stability derived from the combined advantages of microporous molecular sieve HZSM-5 and mesoporous molecular sieve MCM-41.
HZSM-5/MCM-41 molecular sieve(H-ZM) catalysts with well-defined micro/mesoporous structures were synthesized and showed high performance for selective synthesis of triacetin via the esterification reaction of glycerol with acetic acid. The conversion of glycerol was demonstrated to be 100% and the triacetin selectivity was over 91%, which can be attributed to the synergistic effect regarding suitable acidic property, excellent diffusion efficiency and good stability derived from the combined advantages of microporous molecular sieve HZSM-5 and mesoporous molecular sieve MCM-41.
HZSM-5/MCM-41 molecular sieve(H-ZM) catalysts with well-defined micro/mesoporous structures were synthesized and showed high performance for selective synthesis of triacetin via the esterification reaction of glycerol with acetic acid. The conversion of glycerol was demonstrated to be 100% and the triacetin selectivity was over 91%, which can be attributed to the synergistic effect regarding suitable acidic property, excellent diffusion efficiency and good stability derived from the combined advantages of microporous molecular sieve HZSM-5 and mesoporous molecular sieve MCM-41.
引文
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[9]C.Zhang,T.Wang,Y.Ding,One-step synthesis of pyruvic acid from glycerol oxidation over Pb promoted Pt/activated carbon catalysts,Chin.J.Catal.38(2017)928-937.
[10]M.T.Liu,L.X.Chen,D.N.Li,A.J.Wang,Q.L.Zhang,J.J.Feng,One-pot controlled synthesis of AuPd@Pd core-shell nanocrystals with enhanced electrocatalytic performances for formic acid oxidation and glycerol oxidation,J.Colloid Interface Sci.508(2017)551-558.
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[12]S.S.Kale,U.Armbruster,R.Eckelt,U.Bentrup,S.B.Umbarkar,M.K.Dongare,A.Martin,Understanding the role of Keggin type heteropolyacid catalysts for glycerol acetylation using toluene as an entrainer,Appl.Catal.A 527(2016)9-18.
[13]Y.Leng,J.Zhao,P.Jiang,D.Lu,POSS-derived solid acid catalysts with excellent hydrophobicity for highly efficient transformations of glycerol,Catal.Sci.Technol.6(2016)875-881.
[14]S.Bagheri,N.M.Julkapli,W.A.Yehye,Catalytic conversion of biodiesel derived raw glycerol to value added products,Renew.Sustain.Energy Rev.41(2015)113-127.
[15]L.J.Konwar,P.M?ki-Arvela,P.Begum,N.Kumar,A.J.Thakur,J.-P.Mikkola,R.C.Deka,D.Deka,Shape selectivity and acidity effects in glycerol acetylation with acetic anhydride:selective synthesis of triacetin over Y-zeolite and sulfonated mesoporous carbons,J.Catal.329(2015)237-247.
[16]H.Rastegari,H.S.Ghaziaskar,M.Yalpani,Valorization of biodiesel derived glycerol to Acetins by continuous esterification in acetic acid:focusing on high selectivity to Diacetin and Triacetin with no byproducts,Ind.Eng.Chem.Res.54(2015)3279-3284.
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[19]Y.Wang,Q.Wu,X.Meng,F.-S.Xiao,Insights into the organotemplate-free synthesis of zeolite catalysts,Engineering 3(2017)567-574.
[20]J.Liu,Z.Wang,P.Jian,R.Jian,Highly selective oxidation of styrene to benzaldehyde over a tailor-made cobalt oxide encapsulated zeolite catalyst,J.Colloid Interface Sci.517(2018)144-154.
[21]V.L.C.Gon?alves,B.P.Pinto,J.C.Silva,C.J.A.Mota,Acetylation of glycerol catalyzed by different solid acids,Catal.Today 133(2008)673-677.
[22]L.Zhou,E.Al-Zaini,A.A.Adesina,Catalytic characteristics and parameters optimization of the glycerol acetylation over solid acid catalysts,Fuel 103(2013)617-625.
[23]P.Ferreira,I.M.Fonseca,A.M.Ramos,J.Vital,J.E.Castanheiro,Esterification of glycerol with acetic acid over dodecamolybdophosphoric acid encaged in USY zeolite,Catal.Commun.10(2009)481-484.
[24]Y.He,Q.Zhang,X.Zhan,D.Cheng,F.Chen,Aluminum impregnated silica catalyst for Friedel-Crafts reaction:Influence of ordering mesostructure,Chin.J.Chem.Eng.25(2017)1533-1538.
[25]V.Chaudhary,Sweta,Synthesis and catalytic activity of SBA-15 supported catalysts for styrene oxidation,Chin.J.Chem.Eng.26(2018)1300-1306.
[26]J.Liu,S.Fang,R.Jian,F.Wu,P.Jian,Silylated Pd/Ti-MCM-41 catalyst for the selective production of propylene oxide from the oxidation of propylene with cumene hydroperoxide,Powder Technol.329(2018)19-24.
[27]A.Patel,S.Singh,A green and sustainable approach for esterification of glycerol using 12-tungstophosphoric acid anchored to different supports:Kinetics and effect of support,Fuel 118(2014)358-364.
[28]M.S.Khayoon,B.H.Hameed,Synthesis of hybrid SBA-15 functionalized with molybdophosphoric acid as efficient catalyst for glycerol esterification to fuel additives,Appl.Catal.A 433(2012)152-161.
[29]I.Kim,J.Kim,D.Lee,A comparative study on catalytic properties of solid acid catalysts for glycerol acetylation at low temperatures,Appl.Catal.B 148(2014)295-303.
[30]J.Y.Liu,J.F.Chen,Y.Zhang,Direct synthesis of Co@Al-MCM-41 catalyst from conventional Co/SiO2catalyst,RSC Adv.5(2015)62931-62935.
[31]J.Y.Liu,J.F.Chen,Y.Zhang,Cobalt-imbedded zeolite catalyst for direct syntheses of gasoline via Fischer-Tropsch synthesis,Catal.Sci.Technol.3(2013)2559-2564.
[32]N.Rahmat,A.Z.Abdullah,A.R.Mohamed,Recent progress on innovative and potential technologies for glycerol transformation into fuel additives:A critical review,Renew.Sustain.Energy Rev.14(2010)987-1000.
[33]M.J.Da Silva,N.A.Liberto,L.C.De Andrade Leles,U.A.Pereira,Fe4(Si W12O40)3-catalyzed glycerol acetylation:Synthesis of bioadditives by using highly active Lewis acid catalyst,J.Mol.Catal.A Chem.422(2016)69-83.
[34]C.de la Calle,J.M.Fraile,E.Garcia-Bordeje,E.Pires,L.Roldan,Biobased catalyst in biorefinery processes:Sulphonated hydrothermal carbon for glycerol esterification,Catal.Sci.Technol.5(2015)2897-2903.
[35]A.P,S.M.Pudi,P.Biswas,Acetylation of glycerol over sulfated alumina:Reaction parameter study and optimization using response surface methodology,Energy Fuel 30(2016)584-593.
[36]A.B.S.Neto,A.C.Oliveira,E.Rodriguez-Castellón,A.F.Campos,P.T.C.Freire,F.F.F.Sousa,J.M.Filho,J.C.S.Araujo,R.Lang,A comparative study on porous solid acid oxides as catalysts in the esterification of glycerol with acetic acid,Catal.Today(2018)https://doi.org/10.1016/j.cattod.2018.05.057.
[37]J.Sun,X.Tong,L.Yu,J.Wan,An efficient and sustainable production of triacetin from the acetylation of glycerol using magnetic solid acid catalysts under mild conditions,Catal.Today 264(2016)115-122.
[38]M.S.Khayoon,S.Triwahyono,B.H.Hameed,A.A.Jalil,Improved production of fuel oxygenates via glycerol acetylation with acetic acid,Chem.Eng.J.243(2014)473-484.
[39]M.S.Khayoon,B.H.Hameed,Acetylation of glycerol to biofuel additives over sulfated activated carbon catalyst,Bioresour.Technol.102(2011)9229-9235.
[40]J.Liu,T.Chen,P.Jian,L.Wang,X.Yan,Hollow urchin-like NiO/NiCo2O4heterostructures as highly efficient catalysts for selective oxidation of styrene,J.Colloid Interface Sci.526(2018)295-301.
[2]P.S.Kong,M.K.Aroua,W.M.A.W.Daud,H.V.Lee,P.Cognet,Y.Peres,Catalytic role of solid acid catalysts in glycerol acetylation for the production of bio-additives:Areview,RSC Adv.6(2016)68885-68905.
[3]X.Wang,P.Zhang,P.Cui,W.Cheng,S.Zhang,Glycerol carbonate synthesis from glycerol and dimethyl carbonate using guanidine ionic liquids,Chin.J.Chem.Eng.25(2017)1182-1186.
[4]M.Zhang,Y.Sun,J.Shi,W.Ning,Z.Hou,Selective glycerol oxidation using platinum nanoparticles supported on multi-walled carbon nanotubes and nitrogen-doped graphene hybrid,Chin.J.Catal.38(2017)537-544.
[5]D.Wang,Z.Wang,Q.Zhan,Y.Pu,J.-X.Wang,N.R.Foster,L.Dai,Facile and scalable preparation of fluorescent carbon dots for multifunctional applications,Engineering3(2017)402-408.
[6]F.Sabri,R.Idem,H.Ibrahim,Metal oxide-based catalysts for the autothermal reforming of glycerol,Ind.Eng.Chem.Res.57(2018)2486-2497.
[7]J.F.Chen,Green chemical engineering for a better life,Engineering 3(2017)279.
[8]Z.Wu,H.Yan,S.Ge,J.Gao,T.Dou,Y.Li,A.C.K.Yip,M.Zhang,MoO3modified Ni2P/Al2O3as an efficient catalyst for crude glycerol to propylene,Catal.Commun.92(2017)80-85.
[9]C.Zhang,T.Wang,Y.Ding,One-step synthesis of pyruvic acid from glycerol oxidation over Pb promoted Pt/activated carbon catalysts,Chin.J.Catal.38(2017)928-937.
[10]M.T.Liu,L.X.Chen,D.N.Li,A.J.Wang,Q.L.Zhang,J.J.Feng,One-pot controlled synthesis of AuPd@Pd core-shell nanocrystals with enhanced electrocatalytic performances for formic acid oxidation and glycerol oxidation,J.Colloid Interface Sci.508(2017)551-558.
[11]P.U.Okoye,A.Z.Abdullah,B.H.Hameed,Synthesis of oxygenated fuel additives via glycerol esterification with acetic acid over bio-derived carbon catalyst,Fuel 209(2017)538-544.
[12]S.S.Kale,U.Armbruster,R.Eckelt,U.Bentrup,S.B.Umbarkar,M.K.Dongare,A.Martin,Understanding the role of Keggin type heteropolyacid catalysts for glycerol acetylation using toluene as an entrainer,Appl.Catal.A 527(2016)9-18.
[13]Y.Leng,J.Zhao,P.Jiang,D.Lu,POSS-derived solid acid catalysts with excellent hydrophobicity for highly efficient transformations of glycerol,Catal.Sci.Technol.6(2016)875-881.
[14]S.Bagheri,N.M.Julkapli,W.A.Yehye,Catalytic conversion of biodiesel derived raw glycerol to value added products,Renew.Sustain.Energy Rev.41(2015)113-127.
[15]L.J.Konwar,P.M?ki-Arvela,P.Begum,N.Kumar,A.J.Thakur,J.-P.Mikkola,R.C.Deka,D.Deka,Shape selectivity and acidity effects in glycerol acetylation with acetic anhydride:selective synthesis of triacetin over Y-zeolite and sulfonated mesoporous carbons,J.Catal.329(2015)237-247.
[16]H.Rastegari,H.S.Ghaziaskar,M.Yalpani,Valorization of biodiesel derived glycerol to Acetins by continuous esterification in acetic acid:focusing on high selectivity to Diacetin and Triacetin with no byproducts,Ind.Eng.Chem.Res.54(2015)3279-3284.
[17]X.Liao,Y.Zhu,S.-G.Wang,H.Chen,Y.Li,Theoretical elucidation of acetylating glycerol with acetic acid and acetic anhydride,Appl.Catal.B 94(2010)64-70.
[18]J.Liu,D.Wang,J.-F.Chen,Y.Zhang,Cobalt nanoparticles imbedded into zeolite crystals:a tailor-made catalyst for one-step synthesis of gasoline from syngas,Int.J.Hydrog.Energy 41(2016)21965-21978.
[19]Y.Wang,Q.Wu,X.Meng,F.-S.Xiao,Insights into the organotemplate-free synthesis of zeolite catalysts,Engineering 3(2017)567-574.
[20]J.Liu,Z.Wang,P.Jian,R.Jian,Highly selective oxidation of styrene to benzaldehyde over a tailor-made cobalt oxide encapsulated zeolite catalyst,J.Colloid Interface Sci.517(2018)144-154.
[21]V.L.C.Gon?alves,B.P.Pinto,J.C.Silva,C.J.A.Mota,Acetylation of glycerol catalyzed by different solid acids,Catal.Today 133(2008)673-677.
[22]L.Zhou,E.Al-Zaini,A.A.Adesina,Catalytic characteristics and parameters optimization of the glycerol acetylation over solid acid catalysts,Fuel 103(2013)617-625.
[23]P.Ferreira,I.M.Fonseca,A.M.Ramos,J.Vital,J.E.Castanheiro,Esterification of glycerol with acetic acid over dodecamolybdophosphoric acid encaged in USY zeolite,Catal.Commun.10(2009)481-484.
[24]Y.He,Q.Zhang,X.Zhan,D.Cheng,F.Chen,Aluminum impregnated silica catalyst for Friedel-Crafts reaction:Influence of ordering mesostructure,Chin.J.Chem.Eng.25(2017)1533-1538.
[25]V.Chaudhary,Sweta,Synthesis and catalytic activity of SBA-15 supported catalysts for styrene oxidation,Chin.J.Chem.Eng.26(2018)1300-1306.
[26]J.Liu,S.Fang,R.Jian,F.Wu,P.Jian,Silylated Pd/Ti-MCM-41 catalyst for the selective production of propylene oxide from the oxidation of propylene with cumene hydroperoxide,Powder Technol.329(2018)19-24.
[27]A.Patel,S.Singh,A green and sustainable approach for esterification of glycerol using 12-tungstophosphoric acid anchored to different supports:Kinetics and effect of support,Fuel 118(2014)358-364.
[28]M.S.Khayoon,B.H.Hameed,Synthesis of hybrid SBA-15 functionalized with molybdophosphoric acid as efficient catalyst for glycerol esterification to fuel additives,Appl.Catal.A 433(2012)152-161.
[29]I.Kim,J.Kim,D.Lee,A comparative study on catalytic properties of solid acid catalysts for glycerol acetylation at low temperatures,Appl.Catal.B 148(2014)295-303.
[30]J.Y.Liu,J.F.Chen,Y.Zhang,Direct synthesis of Co@Al-MCM-41 catalyst from conventional Co/SiO2catalyst,RSC Adv.5(2015)62931-62935.
[31]J.Y.Liu,J.F.Chen,Y.Zhang,Cobalt-imbedded zeolite catalyst for direct syntheses of gasoline via Fischer-Tropsch synthesis,Catal.Sci.Technol.3(2013)2559-2564.
[32]N.Rahmat,A.Z.Abdullah,A.R.Mohamed,Recent progress on innovative and potential technologies for glycerol transformation into fuel additives:A critical review,Renew.Sustain.Energy Rev.14(2010)987-1000.
[33]M.J.Da Silva,N.A.Liberto,L.C.De Andrade Leles,U.A.Pereira,Fe4(Si W12O40)3-catalyzed glycerol acetylation:Synthesis of bioadditives by using highly active Lewis acid catalyst,J.Mol.Catal.A Chem.422(2016)69-83.
[34]C.de la Calle,J.M.Fraile,E.Garcia-Bordeje,E.Pires,L.Roldan,Biobased catalyst in biorefinery processes:Sulphonated hydrothermal carbon for glycerol esterification,Catal.Sci.Technol.5(2015)2897-2903.
[35]A.P,S.M.Pudi,P.Biswas,Acetylation of glycerol over sulfated alumina:Reaction parameter study and optimization using response surface methodology,Energy Fuel 30(2016)584-593.
[36]A.B.S.Neto,A.C.Oliveira,E.Rodriguez-Castellón,A.F.Campos,P.T.C.Freire,F.F.F.Sousa,J.M.Filho,J.C.S.Araujo,R.Lang,A comparative study on porous solid acid oxides as catalysts in the esterification of glycerol with acetic acid,Catal.Today(2018)https://doi.org/10.1016/j.cattod.2018.05.057.
[37]J.Sun,X.Tong,L.Yu,J.Wan,An efficient and sustainable production of triacetin from the acetylation of glycerol using magnetic solid acid catalysts under mild conditions,Catal.Today 264(2016)115-122.
[38]M.S.Khayoon,S.Triwahyono,B.H.Hameed,A.A.Jalil,Improved production of fuel oxygenates via glycerol acetylation with acetic acid,Chem.Eng.J.243(2014)473-484.
[39]M.S.Khayoon,B.H.Hameed,Acetylation of glycerol to biofuel additives over sulfated activated carbon catalyst,Bioresour.Technol.102(2011)9229-9235.
[40]J.Liu,T.Chen,P.Jian,L.Wang,X.Yan,Hollow urchin-like NiO/NiCo2O4heterostructures as highly efficient catalysts for selective oxidation of styrene,J.Colloid Interface Sci.526(2018)295-301.