H_2WO_4/GO的制备及其超声-氧化脱除模拟油中的硫化物
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摘要
以钨酸和氧化石墨烯为原料,利用浸渍法将钨酸负载到氧化石墨烯上制得H_2WO_4/GO。采用XRD、FT-IR、SEM、BET表征确定H_2WO_4/GO的形态及其结构。以H_2WO_4/GO作为催化剂,H_2O_2作为氧化剂,乙腈作为萃取剂超声氧化脱除模拟油中的二苯并噻吩(DBT)。实验表明,在模拟油为5 mL,钨酸的负载量为30%(质量分数),催化剂为0.02 g,乙腈为1 mL,H_2O_2/S (mol ratio)为8,反应温度为50℃,超声功率为150 W的最佳反应条件下,二苯并噻吩(DBT)、4,6-二甲基二苯并噻吩(4,6-DMDBT)、苯并噻吩(BT)的脱除率分别达到96.6%、81.2%、72.8%。同时,考察了催化剂的循环使用性能,并对超声氧化脱硫机理进行了研究。
H_2WO_4/GO was prepared by dipping method using tungstic acid and graphene oxide as rawmaterials. The morphology and structure of H_2WO_4/GO were characterized by XRD,FT-IR,SEMand BET.The ultrasonic-oxidation desulfurization of model oil containing DBT was carried out with H_2WO_4/GO as catalyst,H_2O_2 as oxidant agent and acetonitrile as extractant. Under the optimum conditions with 5 mL of model oil,30% of tungstic acid loading( mass ratio),0.02 g of catalyst,1 mL of acetonitrile,H_2O_2/S mol ratio of 8,ultrasonic power of 150 W and at 50 ℃,the removal rate of DBT,4,6-DMDBT and BT can reach 96. 6%,81.2%,72.8%,respectively. Besides,the recycling use of catalyst and the mechanism of ultrasonic-oxidation desulfurization were investigated.
H_2WO_4/GO was prepared by dipping method using tungstic acid and graphene oxide as rawmaterials. The morphology and structure of H_2WO_4/GO were characterized by XRD,FT-IR,SEMand BET.The ultrasonic-oxidation desulfurization of model oil containing DBT was carried out with H_2WO_4/GO as catalyst,H_2O_2 as oxidant agent and acetonitrile as extractant. Under the optimum conditions with 5 mL of model oil,30% of tungstic acid loading( mass ratio),0.02 g of catalyst,1 mL of acetonitrile,H_2O_2/S mol ratio of 8,ultrasonic power of 150 W and at 50 ℃,the removal rate of DBT,4,6-DMDBT and BT can reach 96. 6%,81.2%,72.8%,respectively. Besides,the recycling use of catalyst and the mechanism of ultrasonic-oxidation desulfurization were investigated.
引文
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[16] ZHAO Q,BAI C,ZHANG W,LI Y,ZHANG G,ZHANG F,FAN X. Catalytic epoxidation of olefins with graphene oxide supported copper(Salen)complex[J]. Ind Eng Chem Res,2014,53(11):4232-4238.
[17] XU J,XU M,WU J,WU H,ZHANG W H,LI Y X. Graphene oxide immobilized with ionic liquids:Facile preparation and efficient catalysis for solvent-free cycloaddition of CO2to propylene carbonate[J]. RSC Adv,2015,5(88):72361-72368.
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[20] LI S,MOMINOU N,WANG Z,LIU L,WANG L. Ultra-deep desulfurization of gasoline with CuW/TiO2-GO through photocatalytic oxidation[J]. Energy Fuels,2016,30(2):962-967.
[21] ABDI G,ASHOKKUMAR M,ALIZADEH A. Ultrasound-assisted oxidative-adsorptive desulfurization using highly acidic graphene oxide as a catalyst-adsorbent[J]. Fuel,2017,210:639-645.
[22] LIU L,ZHANG Y,TAN W. Ultrasound-assisted oxidation of dibenzothiophene with phosphotungstic acid supported on activated carbon[J].Ultrason Sonochem,2014,21(3):970-974.
[23] FU L,XIA T,ZHENG Y,YANG J,WANG A,WANG Z. Preparation of WO3-reduced graphene oxide nanocomposites w ith enhanced photocatalytic property[J]. Ceram Int,2015,41(4):5903-5908.
[24] ZHAO R,LI X,SU J,GAO X. Preparation of WO3/g-C3N4composites and their application in oxidative desulfurization[J]. Appl Surf Sci,2017,392:810-816.
[25] LU Y,YIN H,WU H,LIU H,JIANG T,WADA Y. Structural effect of tungsten oxides on selective oxidation of cyclopentene to glutaraldehyde[J]. Catal Commun,2006,7(11):832-838.
[26]杨勇辉,孙红娟,彭同江.石墨烯的氧化还原法制备及结构表征[J].无机化学学报,2010,26(11):2083-2090.(YANG Yong-hui,SUN Hong-juan,PENG Tong-jiang. Synthesis and structural characterization of graphene by oxidation reduction[J]. Chin J Inorg Chem,2010,26(11):2083-2090.)
[27] ABDELRAHMAN A A,BETIHA MA,RABIE A M,AHMED H S,ELSHAHAT MF. Removal of refractory organosulfur compounds using an efficient and recyclable{Mo132}nanoball supported graphene oxide[J]. J Mol Liq,2018,252:121-132.
[28] HUANG H,YUE Z,LI G,WANG X,HUANG J,DU Y,YANG P. Ultraviolet-assisted preparation of mesoporous WO3/reduced graphene oxide composites:Superior interfacial contacts and enhanced photocatalysis[J]. J Mater Chem A,2013,1(47):15110-15116.
[29] TANG L,LUO G,KANG L,ZHU M,DAI B. A novel[Bmim]PW/HMS catalyst with high catalytic performance for the oxidative desulfurization process[J]. Korean J Chem Eng,2013,30(2):314-320.
[30] MNDEZ F J,LLANOS A,ECHEVERRA M,JUREGUI R,VILLASANA Y,DAZ Y,BRITO J L. Mesoporous catalysts based on Keggin-type heteropolyacids supported on MCM-41 and their application in thiophene hydrodesulfurization[J]. Fuel,2013,110:249-258.
[31] DAI B,WU P,ZHU W,CHAO Y,SUN J,XIONG J,LI H. Heterogenization of homogenous oxidative desulfurization reaction on graphene-like boron nitride w ith a peroxomolybdate ionic liquid[J]. RSC Adv,2016,6(1):140-147.
[32] ZHANG W,XU K,ZHANG Q,LIU D,WU S,VERPOORT F,SONG X M. Oxidative desulfurization of dibenzothiophene catalyzed by ionic liquid[BMIm]HSO4[J]. Ind Eng Chem Res,2010,49(22):11760-11763.
[33]毛春峰,赵荣祥,李秀萍.硝酸铋作为催化剂氧化脱除模拟油中的二苯并噻吩[J].石油学报(石油加工),2017,33(1):56-63.(MAO Chun-feng,ZHAO Rong-xiang,LI Xiu-ping. Bismuth nitrate as a catalyst for oxidative desulfurization of dibenzothiophene in model oil[J]. Acta Pet Sin:(Pet Process Sect),2017,33(1):56-63.)
[34] WANG G J,ZHANG J K,LIU Y. Catalytic oxidative desulfurization of benzothiophene with hydrogen peroxide over Fe/AC in a biphasic model diesel-acetonitrile system[J]. Korean J Chem Eng,2013,30(8):1559-1565.
[35] DUARTE F A,MELLO P A,BIZZI C A,NUNES MA,MOREIRA E M,ALENCAR MS,FLORESM. Sulfur removal from hydrotreated petroleum fractions using ultrasound-assisted oxidative desulfurization process[J]. Fuel,2011,90(6):2158-2164.
[36] JA'FARI M,EBRAHIMI S L,KHOSRAVI-NIKOU MR. Ultrasound-assisted oxidative desulfurization and denitrogenation of liquid hydrocarbon fuels:A critical review[J]. Ultrason Sonochem,2018,40:955-968.
[37] AKBARI A,OMIDKHAH M,DARIAN J T. Investigation of process variables and intensification effects of ultrasound applied in oxidative desulfurization of model diesel over MoO3/Al2O3catalyst[J]. Ultrason Sonochem,2014,21(2):692-705.
[38] LH,LI P,DENG C,REN W,WANG S,LIU P,ZHANG H. Deep catalytic oxidative desulfurization(ODS)of dibenzothiophene(DBT)with oxalate-based deep eutectic solvents(DESs)[J]. Chem Commun,2015,51(53):10703-10706.
[39] ZHU Y,ZHU M,KANG L,YU F,DAI B. Phosphotungstic acid supported on mesoporous graphitic carbon nitride as catalyst for oxidative desulfurization of fuel[J]. Ind Eng Chem Res,2015,54(7):2040-2047.
[40] CEDEO-CAERO L,GOMEZ-BERNAL H,FRAUSTRO-CUEVAS A, GUERRA-GOMEZ H D, CUEVAS-GARCIA R. Oxidative desulfurization of synthetic diesel using supported catalysts:Part III. Support effect on vanadium-based catalysts[J]. Catal Today,2008,133:244-254.
[41] ZHOU Q,FU S,ZOU M,HE Y,WU Y,WU T. Deep oxidative desulfurization of model oil catalyzed by magnetic MoO3/Fe3O4[J]. RSC Adv,2015,5(85):69388-69393.
[42] YU G,ZHAO J,SONG D,ASUMANA C,ZHANG X,CHEN X. Deep oxidative desulfurization of diesel fuels by acidic ionic liquids[J].Ind Eng Chem Res,2011,50(20):11690-11697.
[43] AKBARI A,OMIDKHAH M,DARIAN J T. Facilitated and selective oxidation of thiophenic sulfur compounds using MoOx/Al2O3-H2O2system under ultrasonic irradiation[J]. Ultrason Sonochem,2015,23:231-237.
[2] LI C,LI D,ZOU S,LI Z,YIN J,WANG A,CUI Y,YAO Z,ZHAO Q. Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents[J]. Green Chem,2013,15(10):2793-2799.
[3] CHAMACK M,MAHJOUB A R,AGHAYAN H. Cesium salts of tungsten-substituted molybdophosphoric acid immobilized onto platelet mesoporous silica:Efficient catalysts for oxidative desulfurization of dibenzothiophene[J]. Chem Eng J,2014,255:686-694.
[4] LI F,LIU Y,SUN Z,ZHAO Y,LIU R,CHEN L,ZHAO D. Photocatalytic oxidative desulfurization of dibenzothiophene under simulated sunlight irradiation w ith mixed-phase Fe2O3prepared by solution combustion[J]. Catal Sci Technol,2012,2(7):1455-1462.
[5] GAO S,LI J,CHEN X,ABDELTAWAB A A,YAKOUT S M,YU G. A combination desulfurization method for diesel fuel:Oxidation by ionic liquid w ith extraction by solvent[J]. Fuel,2018,224:545-551.
[6]丁润东,祖适,周传行,王焕,莫周胜,秦玉才,孙兆林,宋丽娟. CuNaY分子筛的有效吸附位与其脱硫性能的关联性研究[J].燃料化学学报,2018,46(4):451-458.(DING Run-dong,ZU Shi,ZHOU Chuan-hang,WANG Huan,MO Zhou-sheng,QIN Yu-cai,SUN Zhao-lin,SONG Li-juan. Insight into the correlation betw een the effective adsorption sites and adsorption desulfurization performance of CuNaY zeolite[J]. J Fuel Chem Technol,2018,46(4):451-458.)
[7] YANG Y,LV G,LI J,ZHOU C H,WANG H,MO Z S,QIN Y C,SONG L J. Synthesis of ceria nanorods as adsorbent for the adsorption desulfurization of gasoline fuel[J]. J Alloys Compd,2018,747:189-196.
[8] ZHANG Y,LI G,KONG L,LU H. Deep oxidative desulfurization catalyzed by Ti-based metal-organic frameworks[J]. Fuel,2018,219:103-110.
[9] GAO Y,GAO R,ZHANG G,ZHENG Y,ZHAO J. Oxidative desulfurization of model fuel in the presence of molecular oxygen over polyoxometalate based catalysts supported on carbon nanotubes[J]. Fuel,2018,224:261-270.
[10] JA'FARI M,EBRAHIMI S L,KHOSRAVI-NIKOU MR. Ultrasound-assisted oxidative desulfurization and denitrogenation of liquid hydrocarbon fuels:A critical review[J]. Ultrason Sonochem,2018,40:955-968.
[11] HUANG D,WANG Y J,CUI Y C,LUO G S. Direct synthesis of mesoporous TiO2and its catalytic performance in DBT oxidative desulfurization[J]. Microporous Mesoporous Mater,2008,116(1):378-385.
[12] CAMPOS-MARTIN J M,CAPEL-SANCHEZ MC,PEREZ-PRESAS P,FIERRO J L G. Oxidative processes of desulfurization of liquid fuels[J]. J Chem Technol Biotechnol,2010,85(7):879-890.
[13]刘淑芝,孙兰兰,张晓丽,王宝辉,崔宝臣.柴油氧化脱硫技术研究进展[J].化工进展,2007,26(2):212-215.(LIU Zhi-lan,SUN Lan-lan,ZHANG Xiao-li,WANG Bao-hui,CUI Bao-chen. Progress on desulfurization of diesel fuel[J]. Chem Ind Eng Prog,2007,26(2):212-215.)
[14] BETIHA MA,RABIE A M,AHMED H S,ABDELRAHMAN A A,EL-SHAHAT MF. Oxidative desulfurization using graphene and its composites for fuel containing thiophene and its derivatives:An update review[J]. Egypt J Pet,2018,27(4):715-730.
[15] GAO Y,TANG P,ZHOU H,ZHANG W,YANG H,YAN N,MA D. Graphene oxide catalyzed ch bond activation:The importance of oxygen functional groups for biaryl construction[J]. Angew Chem Int Ed,2016,55(9):3124-3128.
[16] ZHAO Q,BAI C,ZHANG W,LI Y,ZHANG G,ZHANG F,FAN X. Catalytic epoxidation of olefins with graphene oxide supported copper(Salen)complex[J]. Ind Eng Chem Res,2014,53(11):4232-4238.
[17] XU J,XU M,WU J,WU H,ZHANG W H,LI Y X. Graphene oxide immobilized with ionic liquids:Facile preparation and efficient catalysis for solvent-free cycloaddition of CO2to propylene carbonate[J]. RSC Adv,2015,5(88):72361-72368.
[18] DIZAJI A K,MORTAHEB H R,MOKHTARANI B. Complete oxidative desulfurization using graphene oxide-based phosphomolybdic acid catalyst:Process optimization by tw o phase mass balance approach[J]. Chem Eng J,2018,335:362-372.
[19]丁邦琴,朱蓓蓓,李侠.氧化石墨烯固载硅钨酸催化氧化脱硫性能的研究[J].化学试剂,2018,40(5):429-436.(DING Bang-qin,ZHU Bei-bei,LI Xia. Catalytic performance of silicotungstic acid supported on grapene oxide for oxidative desulfurization[J]. Chem Reagents,2018,40(5):429-436.)
[20] LI S,MOMINOU N,WANG Z,LIU L,WANG L. Ultra-deep desulfurization of gasoline with CuW/TiO2-GO through photocatalytic oxidation[J]. Energy Fuels,2016,30(2):962-967.
[21] ABDI G,ASHOKKUMAR M,ALIZADEH A. Ultrasound-assisted oxidative-adsorptive desulfurization using highly acidic graphene oxide as a catalyst-adsorbent[J]. Fuel,2017,210:639-645.
[22] LIU L,ZHANG Y,TAN W. Ultrasound-assisted oxidation of dibenzothiophene with phosphotungstic acid supported on activated carbon[J].Ultrason Sonochem,2014,21(3):970-974.
[23] FU L,XIA T,ZHENG Y,YANG J,WANG A,WANG Z. Preparation of WO3-reduced graphene oxide nanocomposites w ith enhanced photocatalytic property[J]. Ceram Int,2015,41(4):5903-5908.
[24] ZHAO R,LI X,SU J,GAO X. Preparation of WO3/g-C3N4composites and their application in oxidative desulfurization[J]. Appl Surf Sci,2017,392:810-816.
[25] LU Y,YIN H,WU H,LIU H,JIANG T,WADA Y. Structural effect of tungsten oxides on selective oxidation of cyclopentene to glutaraldehyde[J]. Catal Commun,2006,7(11):832-838.
[26]杨勇辉,孙红娟,彭同江.石墨烯的氧化还原法制备及结构表征[J].无机化学学报,2010,26(11):2083-2090.(YANG Yong-hui,SUN Hong-juan,PENG Tong-jiang. Synthesis and structural characterization of graphene by oxidation reduction[J]. Chin J Inorg Chem,2010,26(11):2083-2090.)
[27] ABDELRAHMAN A A,BETIHA MA,RABIE A M,AHMED H S,ELSHAHAT MF. Removal of refractory organosulfur compounds using an efficient and recyclable{Mo132}nanoball supported graphene oxide[J]. J Mol Liq,2018,252:121-132.
[28] HUANG H,YUE Z,LI G,WANG X,HUANG J,DU Y,YANG P. Ultraviolet-assisted preparation of mesoporous WO3/reduced graphene oxide composites:Superior interfacial contacts and enhanced photocatalysis[J]. J Mater Chem A,2013,1(47):15110-15116.
[29] TANG L,LUO G,KANG L,ZHU M,DAI B. A novel[Bmim]PW/HMS catalyst with high catalytic performance for the oxidative desulfurization process[J]. Korean J Chem Eng,2013,30(2):314-320.
[30] MNDEZ F J,LLANOS A,ECHEVERRA M,JUREGUI R,VILLASANA Y,DAZ Y,BRITO J L. Mesoporous catalysts based on Keggin-type heteropolyacids supported on MCM-41 and their application in thiophene hydrodesulfurization[J]. Fuel,2013,110:249-258.
[31] DAI B,WU P,ZHU W,CHAO Y,SUN J,XIONG J,LI H. Heterogenization of homogenous oxidative desulfurization reaction on graphene-like boron nitride w ith a peroxomolybdate ionic liquid[J]. RSC Adv,2016,6(1):140-147.
[32] ZHANG W,XU K,ZHANG Q,LIU D,WU S,VERPOORT F,SONG X M. Oxidative desulfurization of dibenzothiophene catalyzed by ionic liquid[BMIm]HSO4[J]. Ind Eng Chem Res,2010,49(22):11760-11763.
[33]毛春峰,赵荣祥,李秀萍.硝酸铋作为催化剂氧化脱除模拟油中的二苯并噻吩[J].石油学报(石油加工),2017,33(1):56-63.(MAO Chun-feng,ZHAO Rong-xiang,LI Xiu-ping. Bismuth nitrate as a catalyst for oxidative desulfurization of dibenzothiophene in model oil[J]. Acta Pet Sin:(Pet Process Sect),2017,33(1):56-63.)
[34] WANG G J,ZHANG J K,LIU Y. Catalytic oxidative desulfurization of benzothiophene with hydrogen peroxide over Fe/AC in a biphasic model diesel-acetonitrile system[J]. Korean J Chem Eng,2013,30(8):1559-1565.
[35] DUARTE F A,MELLO P A,BIZZI C A,NUNES MA,MOREIRA E M,ALENCAR MS,FLORESM. Sulfur removal from hydrotreated petroleum fractions using ultrasound-assisted oxidative desulfurization process[J]. Fuel,2011,90(6):2158-2164.
[36] JA'FARI M,EBRAHIMI S L,KHOSRAVI-NIKOU MR. Ultrasound-assisted oxidative desulfurization and denitrogenation of liquid hydrocarbon fuels:A critical review[J]. Ultrason Sonochem,2018,40:955-968.
[37] AKBARI A,OMIDKHAH M,DARIAN J T. Investigation of process variables and intensification effects of ultrasound applied in oxidative desulfurization of model diesel over MoO3/Al2O3catalyst[J]. Ultrason Sonochem,2014,21(2):692-705.
[38] LH,LI P,DENG C,REN W,WANG S,LIU P,ZHANG H. Deep catalytic oxidative desulfurization(ODS)of dibenzothiophene(DBT)with oxalate-based deep eutectic solvents(DESs)[J]. Chem Commun,2015,51(53):10703-10706.
[39] ZHU Y,ZHU M,KANG L,YU F,DAI B. Phosphotungstic acid supported on mesoporous graphitic carbon nitride as catalyst for oxidative desulfurization of fuel[J]. Ind Eng Chem Res,2015,54(7):2040-2047.
[40] CEDEO-CAERO L,GOMEZ-BERNAL H,FRAUSTRO-CUEVAS A, GUERRA-GOMEZ H D, CUEVAS-GARCIA R. Oxidative desulfurization of synthetic diesel using supported catalysts:Part III. Support effect on vanadium-based catalysts[J]. Catal Today,2008,133:244-254.
[41] ZHOU Q,FU S,ZOU M,HE Y,WU Y,WU T. Deep oxidative desulfurization of model oil catalyzed by magnetic MoO3/Fe3O4[J]. RSC Adv,2015,5(85):69388-69393.
[42] YU G,ZHAO J,SONG D,ASUMANA C,ZHANG X,CHEN X. Deep oxidative desulfurization of diesel fuels by acidic ionic liquids[J].Ind Eng Chem Res,2011,50(20):11690-11697.
[43] AKBARI A,OMIDKHAH M,DARIAN J T. Facilitated and selective oxidation of thiophenic sulfur compounds using MoOx/Al2O3-H2O2system under ultrasonic irradiation[J]. Ultrason Sonochem,2015,23:231-237.
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