摘要
本文研究了二苯并噻吩(DBT)和二甲基亚砜(DMSO)两种含硫化合物的氧化反应。DBT及其衍生物是油品中常见的含硫化合物,通过将其氧化为极性较大的砜可以采取萃取的方式从油品中脱出,达到深度脱硫的目的,而分离得到的砜经过处理后是常用的化工中间体。本文分别采用油溶性氧化剂过氧化氢异丙苯和空气为氧化剂对DBT或DMSO进行氧化,将其分别氧化为二苯并噻吩砜和二甲基砜。
采用过氧化氢异丙苯(CHP)作为油溶性的氧化剂,在固定床反应器中进行DBT的氧化反应。对氧化反应的产物进行了核磁、质谱和红外光谱表征,证明DBT可以被CHP在固定床反应器中氧化为二苯并噻吩砜。采用M003/SiO2作为催化剂时,DBT的转化率可达82%。采用碱土金属氧化物MgO、CaO、SrO、BaO,用分步浸渍的方法对M003/SiO2催化剂进行改性,提高了催化剂的活性。结果表明,碱土金属氧化物CaO,BaO改性的催化剂催化的DBT氧化反应中,DBT的转化率有不同程度的提高,CaO的效果最好,DBT的转化率达到94%。
利用有机化合物的自氧化反应可生成相应的过氧化物的特点,分别在正辛烷、十氢萘和甲苯为溶剂的DBT溶液中通入空气,加入偶氮二异丁腈(AIBN)或过氧化苯甲酰(BPO)等容易生成自由基的物质加快有机化合物的自氧化速度,以Ti-MCM-41为催化剂,将DBT氧化为相应的砜。在十氢萘或正辛烷溶液中DBT的转化率达到100%;在甲苯溶液中DBT的转化率达到83%。这是由于不同的有机分子自氧化生成过氧化物的速度不同造成的。
本文还研究了空气氧化DMSO的反应。在异丙苯溶液中,70℃时,AIBN分解产生自由基,引发异丙苯在空气中的自氧化反应,生成过氧化氢异丙苯;生成的过氧化氢异丙苯在偏钒酸铵的催化作用下,将二甲亚砜氧化生成二甲砜。反应条件为:在20 mL异丙苯中加入3mL DMSO时,反应温度70℃,180 min,催化剂用量0.3 g,AIBN用量0.4 g,DMSO滴加,DMSO转化率可达94%。
The oxidation reaction of dibenzothiophene (DBT) and dimethyl sulfoxide(DMSO) were investigated in the paper. DBT and its derivatives are the common sulfur containing compounds in fuel, which are the most unreactive sulfur compounds during HDS and the major factor limiting deep desulfurization of HDS method. Through oxidation reaction, DBT is oxidized to the corresponding sulfone which has higher polarity than itself, so it can easily be removed by extraction from fuel and deep desulfurization was realized. Oil soluble oxidant cumene hydroperoxide (CHP) and air were used as oxidants for DBT, DMSO respectively. The oxidation products were DBT sulfone and dimethyl sulfone.
Catalytic oxidation of dibenzothiophene (DBT) in decalin was performed in a fixed bed glass reactor using an oil-soluble oxidant, cumene hydroperoxide (CHP), over MoO3/SiO2 catalyst. The conversion of DBT reached 82%. To improve the reactivity MoO3/SiO2 catalyst, alkaline earth metals, such as CaO, BaO, SrO and MgO were introduced to modify MoO3/SiO2 by a two step impregnation method. The results showed that the activity of CaO and BaO modified MoO3/SiO2 catalyst have higher activity than MoO3/SiO2 in the oxidation of DBT with CHP and the MoO3/Ca-SiO2 catalysts has best activity. The DBT conversion reached 94% at 60℃.
Based on the fact that hydrocarbon compounds can be autoxidized to corresponding hydroperoxide slowly by oxygen in air, the oxidations of DBT in decalin or n-octane toluene were respectively performed by the air/Ti-MCM-41 system in the presence of AIBN or BPO. The conversion of DBT can reach 100% when using decalin or n-octane as solvent; while the conversion of DBT can reach only 83% when using toluene as solvent at the same condition. This difference was result from the different auto oxidation speed of organic molecule.
Cumene was oxidized to corresponding hydroperoxide at 70℃in the presence of free radicals decomposed from AIBN. DMSO can be oxidized to dimethyl sulfone by the obtained hydroperoxide on ammonium metavanadate catalyst. The reaction condition were as follows: 3 mL DMSO was added to 20 mL cumene,70℃,180 min, dosage of catalyst 0.3 g, dosage of AIBN is 0.4 g, feeding mode of DMSO is dropping. The conversion of DMSO is 94%.
引文
[1]谷亨杰,吴泳,丁金昌.有机化学[M].北京:高等教育出版社,1990,446-451.
[2]Sato K, Aoki M, Hyodo M, et al. Oxidation of suloxides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions [J]. Tetra.,2001,57(13):2469-2476.
[3]Shi X, Wei J. Selective oxidation of sulfide catalyzed by peroxotungstate immobilized on ionic liquid-modified silica with aqueous hydrogen peroxide [J]. J. Mol. Catal. A,2008,280 (1-2):142-147.
[4]Jeyakumar K, Chakravarthy R D, Chand D K. Simple and efficient method for the oxidation of sulfides to sulfones using hydrogen peroxide and a Mo(VI) based catalyst [J]. Catal. Comm.,2009,10 (14): 1948-1951.
[5]Jeyakumar K, Chand D K. Selective oxidation of sulfides to sulfoxides and sulfones at room temperature using H2O2 and a Mo(VI) salt as catalyst [J]. Tetra. Lett.,2006,47(27):4573-4576.
[6]Bahrami K. Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride [J]. Tetra. Lett.,2006,47 (12):2009-2012.
[7]Kirihara M, Yamamoto J, Noguchi T, et al. Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide [J]. Tetra. Lett.,2009,50(11): 1180-1183.
[8]Alonso D A, Najera C, Varea M. Simple, economical and environmentally friendly sulfone synthesis [J]. Tetra. Lett.,2002,43(19):3459-3461.
[9]Reddy Ch V, Verkade J G. An advantageous tetrameric titanium alkoxide/ionic liquid as a recyclable catalyst system for the selective oxidation of sulfides to sulfones [J]. J. Mol. Catal. A,2007,272(1-2): 233-240.
[10]Mary Imelda Jayaseeli A, Rajagopal S. [Iron(Ⅲ)-salen] ion catalyzed H2O2 oxidation of organic sulfides and sulfoxides [J]. J. Mol. Catal. A,2009,309 (1-2):103-110.
[11]Feng X, Wang Z, Bian N, et al. Sulfide oxidation with H2O2 catalyzed by manganese complex of N,N',N"-tris(2-hydroxypropyl)-1,4,7-triazacyclononane [J]. Inorg. Chim. Acta.2007,360(15):4103-4110.
[12]Gamelas C A, Lourenco T, Costa A, et al. Selective and mild oxidation of sulfides to sulfoxides or sulfones using H2O2 and Cp'Mo(CO)3Cl as catalysts [J]. Tetra. Lett.,2008,49 (32):4708-4712.
[13]Fuerte A, Iglesias M, Sanchez F, et al. Chiral dioxomolybdenum(Ⅵ) and oxovanadium(Ⅴ) complexes anchored on modified USY-zeolite and mesoporous MCM-41 as solid selective catalysts for oxidation of sulfides to sulfoxides or sulfones [J]. J. Mol. Catal. A,2004,211(1-2):227-235.
[14]Raghavan P S, Ramaswamy V, Upadhya T T, et al. Selective catalytic oxidation of thioethers to sulfoxides over Mo-silicalite-1 (MoS-1) molecular sieves [J]. J. Mol. Catal. A,1997,122 (1) 75-80.
[15]Moreau P, Hulea V, Gomez S, et al. Oxidation of sulfoxides to sulfones by hydrogen peroxide over Ti-containing zeolites [J]. Appl. Catal. A,1997,155(2):253-263.
[16]Shaabani A, Rezayan A H. Silica sulfuric acid promoted selective oxidation of sulfides to sulfoxides or sulfones in the presence of aqueous H2O2 [J]. Catal. Comm.,2007,8(7):1112-1116.
[17]Shokrolahi A, Zali A, Pouretedal H R, et al. Carbon-based solid acid catalyzed highly efficient oxidations of organic compounds with hydrogen peroxide [J]. Catal. Comm.,2007,9(5):859-863.
[18]Xiong Z, Zhang J, Hu X. Selective oxidation of spirolactone-related sulfides to corresponding sulfoxides and sulfones by hydrogen peroxide in the presence of N-hydroxysuccinimde [J]. Appl. Catal. A, 2008,334(1-2):44-50.
[19]Kelkar M A, Gogate P R, Pandit A B. Process intensification using cavitation:Optimization of oxidation conditions for synthesis of sulfone [J]. Ultrasonics Sonochemistry,2006,13(6):523-528.
[20]Moussa N, Fraile J M, Ghorbel A, et al. Catalytic oxidation of thioanisole Ph-S-CH3 over VOx/SiO2 and VOx/Al2O3 catalysts prepared by sol-gel method [J]. J. Mol. Catal. A,2006,255(1-2):62-68.
[21]Chen M, Patkar L N, Chen H, et al. An efficient and selective method for preparing glycosyl sulfoxides by oxidizing glycosyl sulfides with OXONE or t-BuOOH on SiO2 [J]. Carbo. Res.,2003, 338(12):1327-1332.
[22]Ayala V, Corma A, Iglesias M, et al. Mesoporous MCM41-heterogenised (salen)Mn and Cu complexes as effective catalysts for oxidation of sulfides to sulfoxides Isolation of a stable supported Mn(Ⅴ)=O complex, responsible of the catalytic activity [J]. J. Mol. Catal. A,2001,221(1-2):201-208.
[23]Stanger K J, Wiench J W, Pruski M, et al. Catalytic oxidation of a thioether and dibenzothiophenes using an oxorhenium(Ⅴ) dithiolate complex tethered on silica [J]. J. Mol. Catal. A,2006,243(2):158-169.
[24]Surendra K, Krishnaveni N S, Kumar V P, et al. Selective and efficient oxidation of sulfides to sulfoxides with N-bromosuccinimide in the presence of (?)-cyclodextrin in water [J]. Tetra. Lett.,2005, 46(27):4581-4583.
[25]Selvam J J P, Suresh V, Rajesh K, et al. A novel rapid sulfoxidation of sulfides with cyclohexylidenebishydroperoxide [J]. Tetra. Lett.,2008,49(21):3463-3465.
[26]Bagherzadeh M, Latifi R, Tahsini L, et al. Catalytic oxidation of sulfides to sulfoxide using manganese(Ⅲ) complexes with bidentate O,N-donor oxazoline ligand and UHP oxidizing agent [J]. Catal. Comm.,2008,10(2):196-200.
[27]Barton D H R, Li W, Smith J A. Binuclear Manganese Complexes as Catalysts in the Selective and Efficient Oxidation of Sulfides to Sulfones [J]. Tetra. Lett.,1998,39(39):7055-7058.
[28]Mirkhani V, Tangestaninejad S, Moghadam M, et al. Efficient oxidation of sulfides with sodium periodate catalyzed by manganese(Ⅲ) Schiff base complexes [J]. J. Mol. Catal. A,2005,242(1-2): 251-255.
[29]Mirkhani V, Moghadam M, Tangestaninejad S, et al. Highly efficient oxidation of sulfides with sodium periodate catalyzed by reusable silica supported Mn(Br8TPP)Cl and Mn(TPP)Cl catalysts under various reaction conditions [J]. J. Appl. Catal. A,2009,353(1):61-67.
[30]Varma R S, Saini R K, Meshram H M. Selective Oxidation of Sulfides to Sulfoxides and Sulfones by Microwave Thermolysis on Wet Silica-Supported Sodium Periodate [J]. Tetra. Lett.,1997,38(37): 6525-6528.
[31]Bonesi S M, Carbonell E, Garcia H, et al. Photocatalytic oxidation of aliphatic and aromatic sulfides in the presence of silica adsorbed or zeolite-encapsulated 2,4,6-triphenyl(thia)pyrylium [J]. J. Appl. Catal. B, 2008,79(4):368-375.
[32]Khanna V, Maikap G C, Iqbal J. An Efficient Oxidation of Sulfides to Sulfones Using 2-Methylpropanal and Dioxygen [J]. Tetra. Lett.,1996,37(19):3367-3370.
[33]Iwahama T, Sakaguchi S, Ishii Y. Selective Oxidation of Sulfides to Sulfoxides with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide (NHPI) in the Presence of Alcohols [J]. Tetra. Lett.,1998, 39(49):9059-9062.
[34]Chellamani A, Harikengaram S. Mechanism of oxidation of aryl methyl sulfoxides with sodium hypochlorite catalyzed by (salen)MnⅢ complexes [J]. J. Mol. Catal. A,2006,247(1-2):260-267.
[35]Alcon M J, Corm A, Iglesias M, et al. Homogeneous and encapsulated within the cavities of zeolite Y chiral manganese and copper complexes with C2-multidentate ligands as catalysts for the selective oxidation of sulphides to sulfoxides or sulfones [J]. J. Mol. Catal. A,2002,178(1-2):253-266.
[36]Sudarikov D V, Rubtsova S A, Kutchin A V. VO(acac)2-catalyzed oxidation of sulfoxides to sulfones using chlorine dioxide [J]. Mendeleev Comm.,2008,18(2):225-226.
[37]Agnihotri G, Misra A K. Fast oxidation of thioglycosides to glycosyl sulfones using KMnO4/CuSO4· 5H2O under neutral reaction conditions [J]. Carbo. Res.,2006,341(2):275-280.
[38]Morais G R, Humphrey A J, Falconer R A. Application of HOF·CH3CN to the synthesis of glycosyl sulfones [J]. Tetra.,2008,64(30-31):7426-7431.
[39]Chen Y, Shen. Activation of superoxide by boron trifluoride:chemoselective and efficient oxidation of sulfides to sulfoxides via tetrafluorodiboronperoxide [J]. Tetra. Lett.,2005,46 (24):4205-4208.
[40]Karunakaran C,'Venkataramanan R. Mo(VI)-catalysis of perborate oxidation in acetic acid:Oxidation of dimethyl and dibenzyl sulfoxides [J]. Catal. Comm.,2006,7(4):236-239.
[41]GHORBANI-CHOGHAMARANI A, ZOLFIGOL M A, RASTEGAR T. Chemoselective Oxidation of Sulfides with Ammonium Nitrate and Silica Sulfuric Acid Catalyzed by KBr [J].催化学报,2009,30(4): 273-275.
[42]Ferrand Y, Daviaud R, Maux P L, et al. Catalytic asymmetric oxidation of sulfide and styrene derivatives using macroporous resins containing chiral metalloporphyrins (Fe,Ru) [J]. Tetra.,2006,17(6): 952-960.
[43]宗立远.柴油氧化脱硫技术的研究进展[J].河北工业科技,2007,24(3):185-188.
[44]侯芙生.创新炼油技术.推动21世纪我国炼油工业的发展[J].石油炼制与化工,2002,33(1):1-9.
[45]陈兰菊,郭绍辉,赵地顺.车用燃料油氧化脱硫技术进展[J].燃料化学学报,2005,33(2):247-252.
[46]梁朝林.高硫原油加工[M].北京:中国石化出版社,2001.
[47]杨永坛.气相色谱-原子发射光谱联用技术在石油馏分硫化物类型分布中的应用研究[D].北京:石油化工科学研究院,2001.
[48]Otsuki S, Nonaka T, Takashima N, et al. Oxidative desulfurization of light gas oil and vacuum gas oil by oxidation and solvent extraction [J]. Energy fuel,2000,14(6):1232-1239.
[49]Song C, Ma X. New design approaches to ultra-clean diesel fuels by deep desulfurization and deep dearomatization [J]. Appl. Catal. B,2003,41(2):207-238.
[50]Whitehurst D, Farag H, Nagamatsu T, et al. Assessment of limitations and potentials for improvement in deep desulfurization through detailed kinetic analysis of mechanistic pathways [J]. Catal. Today,1998, 45(1-4):299-305.
[51]Yin C, Zhu G, Xia D. The distribution of sulfur compounds in full-range FCC and RFCC naphthas [J]. Fuel. Proc. Tech.,2002,79(2):135-140.
[52]吕志凤,战风涛,李林等.用H2O2-有机酸氧化脱除催化裂化柴油中的硫化物[J].石油大学学报(自然科学版),2001,25(3):26-31.
[53]余国贤,陆善祥,陈辉等.活性炭及甲酸催化过氧化氢氧化噻吩脱硫研究[J].燃料化学学报,2005,33(1):74-78.
[54]Yu G, Lu S, Chen H, et al. Oxidative Desulfurization of Diesel Fuels with Hydrogen Peroxide in the Presence of Activated Carbon and Formic Acid [J]. Energy Fuels 2005,19(2):447-452.
[55]Zannikos F, Los E S. Desulfurization of pertoleum fractions by oxidation and sovent extraction [J]. Fuel. Proc. Tech.,1995,42(1):35-45.
[56]Yazu K, Makino M, Ukegawa K. Oxidative desulfurazation of diesel oil with hydrogen peroxide in the presence of acid catalyst in diesel oil/acetic acid biphasic system [J]. Chem. Lett.,2004,33(10):1306-1307.
[57]赵地顺,马四国,刘翠微等.相转移催化应用于催化裂化汽油氧化脱硫的研究[J].高等学校化学学报,2006,27(1):144-146.
[58]Te M, Fairbridge C, Ring Z. Oxidation reactivities of dibenzothiophenes in polyoxometalate/H2O2 and formic acid/H2O2 systems [J]. Appl. Catal. A,2001,219(1-2):267-280.
[59]Yazu K, Yamamoto Y, Furuya T, et al. Oxidation of Dibenzothiophenes in an Organic Biphasic System and Its Application to Oxidative Desulfurization of Light Oil [J]. Energy Fuels,2001, 15(6):1535-1536.
[60]Yazu K, Furuya T, Miki K, et al. Tungstophosphoric Acid-catalyzed Oxidative Desulfurization of Light Oil with Hydrogen Peroxide in a Light Oil/Acetic Acid Biphasic System [J]. Chem. Lett.,2003,32 (10):920-921.
[61]Li C, Jiang Z, Gao J, et al. Ultra-deep desufurization of diesel:oxidation with a recoverable catalyst assembled in Emulsion [J]. Chem. Euro. J,2004,10(9):2277-2280.
[62]Li H, He L, Lu J, et al. Deep Oxidative Desulfurization of Fuels Catalyzed by Phosphotungstic Acid in Ionic Liquids at Room Temperature [J]. Energy Fuels,2009,23(3):1354-1357.
[63]Torres-Garcia E, Canizal G, Gomez Q R, et al. Influence of surface phenomena in oxidative desulfurization with WOx/ZrO2 catalysts [J]. Appl. Phys. A,2004,79(8):2037-2040.
[64]Ramirez-Verduzco L F, Torres-Garcia E, Gomez Q R, et al. Desulfurization of diesel by oxidation/ extraction scheme:influence of the extration solvent [J]. Catalysis Today,2004,98(1-2):289-294.
[65]Zapata B, Pedraza F, Valenzuela M A, et al. Catayst screening for oxidative desulfurization using hydrogen peroxide [J]. Catalysis Today.2005.106(1-4):219-221.
[66]Caero L C, Hernandez E, Pedraza F, et al. Oxidative desulfurization of synthetic diesel using supported catalysts (Part Ⅰ) Study of the operation conditions with a vanadium oxide based catalyst [J]. Catal. Today,2005,107-108:564-569.
[67]Y.Shiraishi, T.Hirai and I.Komasawa,.Oxidative Desulfurization Process for Light Oil Using Titanium silicate Molecular Sieve Catalysts [J]. Journal of Chemical Engineering of Japan,2002,35(12):1305-1311.
[68]Hulea V, Fajula F, Bousquet J. Mild Oxidation with H2O2 over Ti-Containing Molecular Sieves-A very Efficient Method for Removing Aromatic Sulfur Compounds from Fuels [J]. J. Catal.,2001, 198(2):179-186.
[69]Shiraishi Y, Naito T, Hirai T. Vanadosilicate Molecular Sieve as a Catalyst for Oxidative Desulfurization of Light Oil [J]. Ind. Eng.Chem.Res.,2003,42(24):6034-6039.
[70]孔令艳,李钢,王祥生等.TS-1/过氧化氢催化体系中有机硫化物的选择氧化[J].催化学报,2004,25(10):775-778.
[71]Kong L Y, Li G, Wang X S, et al. Kinetics and mechanism of liquid-phase oxidation of thiophene over TS-1 using H2O2 under mild conditions [J]. Catalysis Letters,2004,92(3-4):163-167.
[72]Kong LY, Li G, Wang X S, et al. Mild oxidation of thiophene over TS-1/H2O2 [J]. Catalysis Today 2004,93-95:341-345.
[73]Kong LY, Li G, Wang X S, et al. Oxidative Desulfurization of Organic Sulfur in Gasoline over Ag/TS-1 [J]. Energy Fuels,2006,20(3):896-902.
[74]王云,李钢,王祥生等.Ti-HMS催化氧化脱除模拟燃料中的硫化物[J].催化学报,2004,26(7):567-570.
[75]Wang D H, Qian W H, Amano H, et al. Oxidative desulfurization of fuel oil Part I. Oxidation of dibenzothiophenes using tert-butyl hydroperoxide [J]. Appl. Catal. A,2003,253(1):91-99.
[76]Ishihara A, Wang D, Dumeignil F, et al. Oxidative desulfurization and denitrogenation of a light gas oil using an oxidation/adsorption continuous flow process[J]. Appl. Catal. A,2005,279(1-2):279-287.
[77]Stanger K J, Wiench J W, Pruski M, et al. Catalytic oxidation of a thioether and dibenzothiophenes using an oxorhenium(V) dithiolate complex tethered on silica [J]. J. Mol. Catal. A,2006,243(2):158-169.
[78]Stanger K J, Angelici R J. Silica-Catalyzed tert-Butyl Hydroperoxide Oxidation of Dibenzothiophene and Its 4,6-Dimethyl Derivative:A Route to Low-Sulfur Petroleum Feedstocks [J]. Energy Fuels,2006, 20(5):1757-1760.
[79]Chica A, Corma, A, Domine M E. Catalytic oxidative desulfurization (ODS) of diesel fuel on a continuous fixed-bed reactor [J]. J.Catal.2006,242(2):299-308.
[80]Les K, Stephany R. Oxidative process treats to ULSD levels [J]. Hydrocarbon Processing,2004,83(6): 27-27.
[81]Levy R E, Rappas A S, Nero V P, et al. Unipure's ASR-2 Diesel Desulfurization Process:A Novel, Cost-Effective Process for Ultra- LowSulfur Diesel [C]. NPRA, AM-01-10,2001.
[82]崔毅,刘金龙,黄新龙.柴油选择性氧化-萃取脱硫工艺的研究[J].石油炼制与化工,2002,33(4):17-20.
[83]张群正,张科良,武志远.柴油氧化脱硫工艺研究[J].西安石油大学学报(自然科学版),2004,19(5):56-58.
[84]Paybarah A, Bone R L, Corcoran W H. Selective oxidation of dibenzothiophene by perozybenzoic acid formed in situ [J]. Ind. Eng. Chem. Prod. Res. Dev.,1982,21(3):426-431.
[85]李建源,周新锐,赵德丰等.过氧化环己酮对二苯并噻吩的氧化脱硫研究[J].燃料化学学报,2006,34(2):49-51.
[86]Zhou X, Zhao C, Yang J, et al. Catalytic Oxidation of Dibenzothiophene Using Cyclohexanone Peroxide[J]. Energy Fuels,2007,21(1):7-10.
[87]Tam P S, Kittrell J R, Eldridge J W. Desulfurization of fuel oil by oxidation and extraction.1. Enhancement of extraction oil yield [J]. Ind. Eng. Chem. Res.,1990,29 (3):321-324.
[88]Tam P S, Kittrell J R, Eldridge J W. Desulfurization of fuel oil by oxidation and extraction.2. Kinetic modeling of oxidation reaction [J]. Ind. Eng. Chem. Res.,1990,29 (3):324-329.
[89]唐晓东,税蕾蕾,刘亮.直馏柴油NOx-空气催化氧化脱硫研究[J].催化学报,2004,25(10):789-792.
[90]杨金荣,侯影飞,孔瑛等.柴油臭氧氧化脱硫研究[J].石油大学学报(自然科学版),2002,26(4):84-90.
[91]Otsuki S, Nonaka T, QianW, et al. Oxidative desulfurization of middle distillate using ozone [J]. J. Jap. Petr. Inst.,1999,42(5):315-320.
[92]蒋登高,章亚东等.精细有机合成[M].北京:化学工业出版社,2001,190-214.
[93]Murata S, Murata K, Nomura M, et al. A Novel Oxidative Desulfurization System for Diesel Fuels with Molecular Oxygen in the Presence of Cobalt Catalysts and Aldehydes [J]. Energy Fuels,2004,18(1): 116-121.
[94]Ma X, Zhou A, Song C. A novel method for oxidative desulfurization of liquid hydrocarbon fuels based on catalytic oxidation using molecular oxygen coupled with selective adsorption [J]. Catal. Today, 2007,123(1-4):276-284.
[95]Lii H, Gao J, Jiang Z, et al. Oxidative desulfurization of dibenzothiophene with molecular oxygen using emulsion catalysis [J]. Chem. Commun.,2007, (2):150-152.
[96]Rao T V, Sain B, Kafola S, et al. Oxidative Desulfurization of HDS Diesel Using the Aldehyde/Molecular Oxygen Oxidation System [J]. Energy Fuels,2007,21(6):3420-3424.
[97]Sampanthar J T, Xiao H, Dou J, et al. A novel oxidative desulfurization p rocess to remove refractory sulfur compounds from diesel fuel [J]. Appl. Catal. B,2006,63(1-2):85-93.
[98]唐晓东,王豪,税蕾蕾等. 柴油催化氧化脱硫技术研究[J]. 炼油技术与工程,2004,34(6):47-49.
[99]唐晓东,刘亮,税蕾蕾等.直馏柴油催化氧化脱硫均相催化剂的制备与评价[J]. 化工学报,2005,56(4):642-645.
[100]唐晓东,崔盈贤,于志鹏等.直馏柴油的选择性催化氧化脱硫[J].石油学报(石油加工),2006,22(1):90-94.
[101]Mei H, Mei B W, Yen T F. A new method for obtaining ultra-low sulfur diesel fuel via ultrasound assisted oxidative desulfurization [J]. Fuel,2003,82(4):415-423.
[102]AVIDAN A, CULLEN M. Sulphc co-desulfurization via selective oxidation pilot plant results and commercialization plans [C]. AM 01 55,2001 NPRA Annual Meeting, March 18-20, New Orleans, Louisiana.
[103]李英,赵德智,袁秋菊.在超声条件下过氧化氢-三氟乙酸对柴油氧化脱硫性能的研究[J].炼油技术与工程,2005,35(4):36-39.
[104]Hirai T, Shiraishi Y, Ogawa K, et al. Effect of Photosensitizer and Hydrogen Peroxide on Desulfurization of Light Oil by Photochemical Reaction and Liquid-Liquid Extraction [J]. Ind. Eng. Chem. Res.,1997,36(3):530-533.
[105]Shiraishi Y, Hara H, Hirai T, et al. A Deep Desulfurization Process for Light Oil by Photosensitized Oxidation Using a Triplet Photosensitizer and Hydrogen Peroxide in an Oil/Water Two-Phase Liquid- Liquid Extraction System [J]. Ind. Eng. Chem. Res.,1999,38(4):1589-1595.
[106]Matsuzawa S, Tanaka J, Sato S, et al. Photocatalytic oxidation of dibenzothiophenes in acetonitrile using TiO2:effect of hydrogen peroxide and ultrasound irradiation [J]. J. Photochem. Photobio. A,2002, 149:183-189.
[107]Shiraishi Y, Taki Y, Hira T, et al. Visible light-induced desulfurization technique for light oils [J]. Chem. Comm.,1998,24:2601-2602.
[108]Shiraishi Y, Taki Y, Hira T, et al. Visible light-induced deep desulfurization process for light oils by photochemical electron-transfer oxidation in an organic two-phase extraction system [J]. Ind. Eng. Chem. Res.,1999,38(9):3310-3318.
[109]战风涛,吕志凤,徐永强等.柴油的光诱导氧化脱硫研究[J].炼油技术与工程,2005,35(4):40-43.
[110]司航.化工产品手册.有机化工原料[M].北京:化学工业出版社,1999.
[111]刘成旭.一种二甲基砜的制备方法:CN 1326929A[P].2001.
[112]田军.一种生产二甲基砜的方法:CN 135615A[P].2002.
[113]张勇.二甲基砜的制备方法:CN 1397548A[P].2003.
[114]Sheldon R A. Synthetic and mechanistic aspects of metal-catalysed epoxidations with hydroperoxides [J]. J. Mol. Catal.,1980,7(1):107-126.
[115]Overberger C G, Cummins R W. Mechanism of the Oxidation of p,p'-Dichlorobenzyl Sulfide by Peroxybenzoic and para Substituted Peroxybenzoic Acids [J]. J. Am. Chem. Soc.,1953,75(17):4250-4254.
[116]Banares M A, Fierro J L G. Selective oxidation of methane to formaldehyde on supported molybdate catalysts [J]. Catal. Lett.,1993,17(3-4):205-211.
[117]Radhakrishnan R, Reed C, Oyama S T. Variability in the Structure of Supported MoO3 Catalysts: Studies Using Raman and X-ray Absorption Spectroscopy with ab Initio Calculations [J]. J. Phys. Chem. B, 2001,105(36):8519-8530.
[118]Larrubia M A, Gutierrez-Alejandre A, Ramirez J, Busca G. A FT-IR study of the adsorption of indole, carbazole, benzothiophene, dibenzothiophene and 4,6-dibenzothiophene over solid adsorbents and catalysts [J]. Appl. Catal. A.,2002,224(1-2):167-178.
[119]Williams C C, Ekerdt J G, Jehng J M, Hardcastle F D, Turek A M, Wachs I E. A Raman and Ultraviolet Diffuse Reflectance Spectroscopic Investigation of Silica-Supported Molybdenum Oxide [J]. J. Phys. Chem.,1991,95(22):8781-9797.
[120]Banares M A, Spencer N D, Jones M D, Wachs I E. Effect of alkali metal cations on the structure of Mo(Ⅵ)/SiO2 catalysts and its relevance to the selective oxidation of methane and methanol [J]. J. Catal., 1994,146(1):204-210.
[121]Malka K, Tatibouet J M. A Two-Step Preparation of Silica-Supported Calcium-Molybdenum Catalysts [J]. J. Catal.,1998,175(2):204-212.
[122]O'Young. Effects of Alkali-Metal Promoters (Potassium and Cesium) on a MO/γ-Al2O3 Catalyst [J]. J. Phys. Chem.,1989,93(5):2015-2018.
[123]Spencer N D, Pereira C J, Grasselli R K. The effect of sodium on the MoO3-SiO2-catalyzed partial oxidation of methane [J]. J. Catal.,1990,126(2):546-554.
[124]Erdohelyi A, Fodor 1 K, Ne'meth R, Hancz A, Oszko A. Partial Oxidation of Methane on Silica-Supported Different Alkali Metal Molybdates [J]. J. Catal.,2001,199(2):328-377.
[125]Wu C Y, Swift H E. Selective olefin epoxidation at high hydroperoxide-to-olefin ratios [J]. J. Catal., 1976,43 (1-3):380-383.
[126]Zhang W H, Shi J L, Wang L Z, Yan D S. The post-preparation of mesoporous Zr-MCM-41 via grafting reaction [J]. Mater. Lett.,2000,46(1):35-38.
[127]Sohn J R, Decanio S J, Lunsford J H, Odennell D. Determination of framework aluminium content in dealuminated Y-type zeolites:a comparison based on unit cell size and wavenumber of i.r. bands [J]. Zeolites,1986,6(3):225-227
[128]穆光照.自由基反应[M].北京:高等教育出版社,1985,15-23.
[129]张颖,王玉刚.苯酚丙酮装置CHP浓度测定方法评价[J].石化技术,2002,9(2):77-79.
[130]Beck J C, Vartuli J C, Roth W J, et al. A New Family of Mesoporous Molecular Sieves Prepared with Liquid Crystal Templates [J]. J. Am. Chem. Soc.,1992,114(27):10834-10843.
[131]Casuscelli S G, Griselda A, Eimer a, et al. Ti-MCM-41 as catalyst for a-pinene oxidation Study of the effect of Ti content and H2O2 addition on activity and selectivity [J]. Catal. Today,2008,133-135: 678-683.
[132]Hulea V, Moreau P, Renzo F D. Thioether oxidation by hydrogen peroxide using titanium-containing zeolites as catalysts [J]. J. Mol. Catal. A,1996,111(3):325-332.
[133]郭新闻,李英武,王祥生.Ti-MCM-41的合成及表征[J].大连理工大学学报,2005,45(3):326-329.
[134]Eimer G A, Casuscelli S G, Ghione G E, et al. Synthesis, characterization and selective oxidation properties of Ti-containing mesoporous catalysts [J]. Appl. Catal.,2006,298(1):232-242.
[135]Guidotti M, Nicoletta R, Rinaldo P, et al. Epoxidation on titanium-containing silicates:do structural features really affect the catalytic performance? [J]. J. Catal.,2003,214(2):242-250.
[136]乔亏,张富民,潘多丽等.高钛Ti-MCM-41分子筛的合成、表征与催化氧化性能考察[J].无机化学学报,2008,24(5):748-754.
[137]Eimer G A, Casuscelli S G, Corina M, et al. The influence of Ti-loading on the acid behavior and on the catalytic efficiency of mesoporous Ti-MCM-41 molecular sieves [J]. Catal. Today,2008,133-135: 639-646.
[138]张勇.二甲基砜的合成及在保健食品和医药中的应用[J].广州食品工业科技,2004,20(2):136-139.