Technical progress in the oxidation of 1, 2, 4-trimethylbenzene to 2, 3, 5-trimethylbenzoquinone

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Abstract 2, 3, 5-trimethylbenzoquinone (TMBQ) is a key intermediate for the synthesis of vitamin E. Using 1, 2, 4-trimethylbenzene (TMB) as a raw material to prepare TMBQ through one-step oxidation has high atomic economy and less three wastes. It is the next-generation key technology with the most application potential, which might significantly reduce production costs of vitamin E. For this technical route, the research progress in the synthesis of TMBQ from TMB by one-step catalytic oxidation in recent years was systematically reviewed. The effects of different catalytic systems on the selective oxidation of TMB were analyzed and summarized, the industrial application of direct oxidation technology of TMB to TMBQ was also prospected.

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	LI Bin
	LI Peiyu
	JIANG Shuang
	ZHANG Tianyong

Keywords： 1, 2, 4-trimethylbenzene； 2, 3, 5-trimethylbenzoquinone； catalysis； oxidation； hydrogen peroxide

Received 2021-02-05;

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LI Bin, LI Peiyu, JIANG Shuang, ZHANG Tianyong.Technical progress in the oxidation of 1, 2, 4-trimethylbenzene to 2, 3, 5-trimethylbenzoquinone[J] Chemcial Industry and Engineering, 2022,V39(1): 40-50

[1] TIETZE L F, SOMMER K M, ZINNGREBE J, et al. Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E[J]. Angewandte Chemie International Edition, 2005, 44(2): 257-259
[2] NETSCHER T, MALAISÉ G, BONRATH W, et al. A new route to vitamin E key-intermediates by olefin cross-metathesis[J]. Catalysis Today, 2007, 121(1/2): 71-75
[3] HERNÁNDEZ-TORRES G, URBANO A, CARREÑO M C, et al. Stereocontrolled generation of the (2R) chroman core of vitamin E: Total synthesis of (2R, 4'RS, 8'RS)-α-tocopherol[J]. Organic Letters, 2009, 11(21): 4930-4933
[4] WANG Yiyong, ZHANG Chengliang, XU Xinde. Research progress of purification technology of natural vitamin E[J]. China Food Additives, 2014(2): 203-207(in Chinese) 王义永, 章城亮, 许新德. 天然维生素E提纯技术进展[J]. 中国食品添加剂, 2014(2): 203-207
[5] ZHOU Jian, TANG Hongbo. Determination of vitamin E in soybean residue with GC-MS by using internal standard method[J]. Applied Chemical Industry, 2010, 39(12): 1934-1935(in Chinese) 周健, 汤洪波. GC-MS内标法测定大豆渣油中维生素E的含量[J]. 应用化工, 2010, 39(12): 1934-1935
[6] WU Ying, CHEN Hong. A GC analysis of different components in synthesizing 2, 3, 5-trimethyl hydroquinone[J]. Huaxue Shijie (Chemical World), 2002, 43(9): 466-468(in Chinese) 吴缨, 陈红. 三甲氢醌合成中各组分的气相色谱分析[J]. 化学世界, 2002, 43(9): 466-468
[7] YAMAGUCHI S, SHINODA H, INOUE M, et al. ChemInform abstract: Mechanistic studies on the oxidation of naphthalenes and methylbenzenes to quinones with H₂O₂ in the presence of Pd(Ⅱ) catalysts[J]. ChemInform, 1986, 34(11): 4467-4473
[8] SUN H J, HARMS K, SUNDERMEYER J. Aerobic oxidation of 2, 3, 6-trimethylphenol to trimethyl-1, 4-benzoquinone with copper(Ⅱ) chloride as catalyst in ionic liquid and structure of the active species[J]. Journal of the American Chemical Society, 2004, 126(31): 9550-9551
[9] SUN H, LI X, SUNDERMEYER J. Aerobic oxidation of phenol to quinone with copper chloride as catalyst in ionic liquid[J]. Journal of Molecular Catalysis A: Chemical, 2005, 240(1/2): 119-122
[10] LIU Dongming, LI Xun, ZANG Hengchang. Research advance in the synthesis of vitamin E nucleus[J]. University Chemistry, 2015, 30(3): 26-33(in Chinese) 柳东明, 李荀, 臧恒昌. 维生素E母核合成研究进展[J]. 大学化学, 2015, 30(3): 26-33
[11] ZHOU J, HUA Z, CUI X, et al. Hierarchical mesoporous TS-1 zeolite: A highly active and extraordinarily stable catalyst for the selective oxidation of 2, 3, 6-trimethylphenol[J]. Chemical Communications, 2010, 46(27): 4994-4996
[12] SHIMIZU M, WATANABE Y, ORITA H, et al. Synthesis of alkyl substitutedp-benzoquinones from the corresponding phenols using molecular oxygen catalyzed by copper(Ⅱ) chloride-amine hydrochloride systems[J]. Bulletin of the Chemical Society of Japan, 1992, 65(6): 1522-1526
[13] WANG C, GUAN W, XIE P, et al. Effects of ionic liquids on the oxidation of 2, 3, 6-trimethylphenol to trimethyl-1, 4-benzoquinone under atmospheric oxygen[J]. Catalysis Communications, 2009, 10(5): 725-727
[14] ZHANG W, HU L, ZHANG H, et al. Stable non-covalent Co(salphen)-based polymeric catalyst for highly efficient and selective oxidation of 2, 3, 6-trimethylphenol[J]. Polymers, 2020, 12(5): 1076-1086
[15] CHANG S, AN H, CHEN Y, et al. Multiunit catalysts with synergistic reactivity: Three-dimensional polyoxometalate-based coordination polymers for highly efficient synthesis of functionalized p-benzoquinones[J]. ACS Applied Materials & Interfaces, 2019, 11(41): 37908-37919
[16] ZHANG Tianyong, WANG Mengying, LI Bin, et al. Research progress on the catalytic oxidation of 2, 3, 6-trimethylphenol to 2, 3, 5-trimethybenzoquinone[J]. Chemical Industry and Engineering Progress, 2016, 35(2): 513-518(in Chinese) 张天永, 王梦颖, 李彬, 等. 三甲基苯酚催化合成三甲基苯醌研究进展[J]. 化工进展, 2016, 35(2): 513-518
[17] SONG Binbin, LIU Haitao. Market and technological advance on comprehensive utilization of C₉ heavy aromatics[J]. Chemical Industry, 2016, 34(3): 36-39(in Chinese) 宋彬彬, 刘海涛. 重整C₉芳烃制取偏三甲苯、均三甲苯的技术与产品市场[J]. 化学工业, 2016, 34(3): 36-39
[18] LI Jiansheng, ZHANG Shuyun. New process for the electrolytic synthesis of 2, 3, 5-trimethylbenzoquinone[J]. Chemical Engineer, 1994, 8(2): 22-23(in Chinese) 李建生, 张淑云. 2, 3, 5-三甲基苯醌电解合成新工艺[J]. 化学工程师, 1994, 8(2): 22-23
[19] BAI Yuansheng, LI Zicheng, WANG Lixin, et al. Research progress on the synthesis of 2, 3, 5-trimethylhydroquinone[J]. Chinese Journal of Synthetic Chemistry, 2014, 22(3): 423-428(in Chinese) 白元盛, 李子成, 王立新, 等. 2, 3, 5-三甲基氢醌的合成研究进展[J]. 合成化学, 2014, 22(3): 423-428
[20] YANG Junjuan, LI Xiying, LIU Yong, et al. Research progress for manufacturing 2, 3, 5-trimethylhydroquinone[J]. Chemical Research, 2011, 22(4): 94-99(in Chinese) 杨俊娟, 李西营, 刘勇, 等. 2, 3, 5-三甲基氢醌制备工艺研究进展[J]. 化学研究, 2011, 22(4): 94-99
[21] ZHANG Pengpeng, MENG Sihan, ZHAO Yu, et al. Homogenous hydroxylation of benzene to phenol under iron acetate micelles catalysis[J]. Shandong Chemical Industry, 2020, 49(3): 3-6(in Chinese) 张鹏鹏, 孟思寒, 赵宇, 等. 铁盐胶束均相催化苯羟基化制备苯酚的反应[J]. 山东化工, 2020, 49(3): 3-6
[22] ZHANG T, NIE X, YU W, et al. Single atomic Cu-N₂ catalytic sites for highly active and selective hydroxylation of benzene to phenol[J]. iScience, 2019, 22: 97-108
[23] ZHAO Q, ZHANG L, ZHAO M, et al. Vanadium oxyacetylacetonate grated on metal organic framework as catalyst for the direct hydroxylation of benzene to phenol[J]. ChemistrySelect, 2020, 5(22): 6818-6822
[24] KURIKAWA Y, TOGO M, MURATA M, et al. Mechanistic insights into visible light-induced direct hydroxylation of benzene to phenol with air and water over Pt-modified WO₃ photocatalyst[J]. Catalysts, 2020, 10(5): 557-568
[25] SHAHID A, LOPEZ-OROZCO S, MARTHALA V R, et al. Direct oxidation of benzene to phenol over hierarchical ZSM-5 zeolites prepared by sequential post synthesis modification[J]. Microporous and Mesoporous Materials, 2017, 237: 151-159
[26] ZHAO X, ZHANG T, ZHOU Y, et al. Preparation of peracetic acid from hydrogen peroxide: Part Ⅰ: Kinetics for peracetic acid synthesis and hydrolysis[J]. Journal of Molecular Catalysis A: Chemical, 2007, 271(1/2): 246-252
[27] ZHAO X, CHENG K, HAO J, et al. Preparation of peracetic acid from hydrogen peroxide, part Ⅱ: Kinetics for spontaneous decomposition of peracetic acid in the liquid phase[J]. Journal of Molecular Catalysis A: Chemical, 2008, 284(1/2): 58-68
[28] SUN X, ZHAO X, DU W, et al. Kinetics of formic acid-autocatalyzed preparation of performic acid in aqueous phase[J]. Chinese Journal of Chemical Engineering, 2011, 19(6): 964-971
[29] DE FILIPPIS P, SCARSELLA M, VERDONE N. Peroxyformic acid formation: A kinetic study[J]. Industrial & Engineering Chemistry Research, 2009, 48(3): 1372-1375
[30] MORO-OKA Y, AKITA M. Bio-inorganic approach to hydrocarbon oxidation[J]. Catalysis Today, 1998, 41(4): 327-338
[31] ORITA H, SHIMIZU M, HAYAKAWA T, et al. Oxidation of methoxy-and/or methyl-substituted benzenes and naphthalenes to quinones and phenols by H₂O₂ in HCOOH[J]. Bulletin of the Chemical Society of Japan, 1989, 62(5): 1652-1657
[32] ASAKAWA Y, MATSUDA R, TORI M, et al. Efficient preparation of some biologically active substances from natural and nonnatural aromatic compounds by m-chloroperbenzoic acid oxidation[J]. The Journal of Organic Chemistry, 1988, 53(23): 5453-5457
[33] ZHANG X, HAO Z, YANG C, et al. Preparation of vitamin E intermediate from an inexpensive substrate by selective oxidation of pseudocumene in HCOOH-H₂O₂ system[J]. Transactions of Tianjin University, 2018, 24(3): 263-271
[34] CHEN Hong, WU Ying, XU Guomei. Synthesis of 2, 3, 5-trimethylhydroquinone by direct oxidation using hydrogen peroxide[J]. Advances in Fine Fetrochemicals, 2002, 3(4): 25-27(in Chinese) 陈红, 吴缨, 徐国梅. 过氧化氢直接氧化法合成2, 3, 5-三甲基氢醌[J]. 精细石油化工进展, 2002, 3(4): 25-27
[35] ZHANG Weidong, MA Xinqi, AN Limin. Process for green synthesis of 2, 3, 5-trimethylhydroquinone[J]. Chemical Research, 2012, 23(2): 31-34(in Chinese) 张卫东, 马新起, 安利敏. 2, 3, 5-三甲基氢醌的绿色合成工艺研究[J]. 化学研究, 2012, 23(2): 31-34
[36] ZHANG Tianyong, LIU Xiaosi, LI Bin, et al. Effect of coupling agent modification on the catalytic performance of γ-Al₂O₃ for pseudocumene oxidation[J]. Chemistry, 2017, 80(6): 573-578(in Chinese) 张天永, 刘晓思, 李彬, 等. 偶联剂改性对γ-Al₂O₃催化氧化偏三甲苯性能的影响[J]. 化学通报, 2017, 80(6): 573-578
[37] BOHLE A, SCHUBERT A, SUN Y, et al. A new metal-free access to vitamin K3[J]. Advanced Synthesis & Catalysis, 2006, 348(9): 1011-1015
[38] YANG Chaoqun. Preparation of 2, 3, 5-trimethylquinone from one-step oxidation of 1, 2, 4-trimethylbenzene[D]. Tianjin: Tianjin University, 2017 (in Chinese) 杨超群. 偏三甲苯一步氧化制备2, 3, 5-三甲基苯醌的研究[D]. 天津: 天津大学, 2017
[39] GÓMEZ L, GARCIA-BOSCH I, COMPANY A, et al. Stereospecific C-H oxidation with H₂O₂ catalyzed by a chemically robust site-isolated iron catalyst[J]. Angewandte Chemie (International Ed in English), 2009, 48(31): 5720-5723
[40] CHEN M, WHITE M C. Combined effects on selectivity in Fe-catalyzed methylene oxidation[J]. Science, 2010, 327(5965): 566-571
[41] HENSEN E J M, ZHU Q, JANSSEN R A J, et al. Selective oxidation of benzene to phenol with nitrous oxide over MFI zeolites: 1. On the role of iron and aluminum[J]. Journal of Catalysis, 2005, 233(1): 123-135
[42] CHOI J S, KIM T H, CHOO K Y, et al. Direct synthesis of phenol from benzene on iron-impregnated activated carbon catalysts[J]. Applied Catalysis A: General, 2005, 290(1/2): 1-8
[43] ANILKUMAR G, BITTERLICH B, GELALCHA F G, et al. An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide[J]. Chemical Communications (Cambridge, England), 2007, (3): 289-291
[44] BITTERLICH B, ANILKUMAR G, GELALCHA F G, et al. Development of a general and efficient iron-catalyzed epoxidation with hydrogen peroxide as oxidant[J]. Chemistry-an Asian Journal, 2007, 2(4): 521-529
[45] SCHRÖDER K, TONG X F, BITTERLICH B, et al. Novel biomimetic iron-catalysts for environmentally benign epoxidations of olefins[J]. Tetrahedron Letters, 2007, 48(36): 6339-6342
[46] GELALCHA F, BITTERLICH B, ANILKUMAR G, et al. Iron-catalyzed asymmetric epoxidation of aromatic alkenes using hydrogen peroxide[J]. Angewandte Chemie International Edition, 2007, 46(38): 7293-7296
[47] BITTERLICH B, SCHRÖDER K, TSE M K, et al. An improved iron-catalyzed epoxidation of aromatic and aliphatic olefins with hydrogen peroxide as oxidant[J]. European Journal of Organic Chemistry, 2008, 2008(29): 4867-4870
[48] LIU Chunyan, LIU Lin, QIAN Jianhua. A novel synthesis method of 2, 3, 5-trimethylhydroquinone[J]. Liaoning Chemical Industry, 2006, 35(5): 249-250, 290 (in Chinese) 刘春艳, 刘琳, 钱建华. 2, 3, 5-三甲基氢醌合成新方法[J]. 辽宁化工, 2006, 35(5): 249-250, 290
[49] MÖLLER K, WIENHÖFER G, WESTERHAUS F, et al. Oxidation of 1, 2, 4-trimethylbenzene (TMB), 2, 3, 6-trimethylphenol (TMP) and 2-methylnaphthalene to 2, 3, 5-trimethylbenzoquinone (TMBQ) and menadione (vitamin K3)[J]. Catalysis Today, 2011, 173(1): 68-75
[50] BAO Ji, LIU Gaofu, GAO Rong, et al. Study on the synthesis of 2, 3, 5-trimethylbenzoquinone[J]. Chemical Enterprise Management, 2016, (4): 187-187 (in Chinese) 包吉, 刘高赋, 高荣, 等. 2, 3, 5-三甲基苯醌的合成研究[J]. 化工管理, 2016, (4): 187-187
[51] ZHAO Feng, YANG Beiyu, GU Jianjiang, et al. Performance of Cu-MCM-41 catalyst for catalytic oxidation of 1, 2, 4-trimethylbenzene[J]. Industrial Catalysis, 2012, 20(6): 62-66(in Chinese) 赵峰, 杨蓓玉, 顾剑江, 等. Cu-MCM-41催化剂对偏三甲苯的催化氧化性能[J]. 工业催化, 2012, 20(6): 62-66
[52] NOREÑA-FRANCO L, HERNANDEZ-PEREZ I, AGUILAR-PLIEGO J, et al. Selective hydroxylation of phenol employing Cu-MCM-41 catalysts[J]. Catalysis Today, 2002, 75(1/2/3/4): 189-195
[53] JIANG Siyang, KONG Yan, WU Cheng, et al. Catalytic performance of Cu-MCM-41 with high copper content for the direct hydroxylation of benzene to phenol[J]. Chinese Journal of Catalysis, 2006, 27(5): 421-426(in Chinese) 蒋斯扬, 孔岩, 吴丞, 等. 高Cu含量MCM-41在苯直接羟基化反应中的催化性能[J]. 催化学报, 2006, 27(5): 421-426
[54] SUN Jianmin, MENG Xiangju, WANG Runwei, et al. Preparation, characterization of Cu-MCM-41 and its catalysis for hydroxylation of aromatic compounds[J]. Chemical Research in Chinese Universities, 2000, 21(9): 1451-1454(in Chinese) 孙建敏, 孟祥举, 王润伟, 等. Cu修饰的MCM-41的合成、表征及对芳烃羟化反应催化作用的研究[J]. 高等学校化学学报, 2000, 21(9): 1451-1454
[55] XIE Lin, LIN Furong, LI Wei, et al. Functionalized ionic liquid catalytic oxidation of pseudocumene to 2, 3, 5-trimethyl-benzoquinone[J]. China Building Materials Science & Technology, 2017, 26(5): 33-35(in Chinese) 颉林, 林富荣, 李薇, 等. 功能化离子液体催化氧化偏三甲苯合成2, 3, 5-三甲基苯醌[J]. 中国建材科技, 2017, 26(5): 33-35
[56] VAN VLIET M C A, MANDELLI D, ARENDS I W C E, et al. Alumina: A cheap, active and selective catalyst for epoxidations with (aqueous) hydrogen peroxide[J]. Green Chemistry, 2001, 3(5): 243-246
[57] SEPULVEDA J, TEIXEIRA S, SCHUCHARDT U. Alumina-catalyzed epoxidation of unsaturated fatty esters with hydrogen peroxide[J]. Applied Catalysis A: General, 2007, 318: 213-217
[58] CESQUINI R, DE SE SILVA J, WOITISKI C, et al. Alumina-catalyzed epoxidation with hydrogen peroxide: Recycling experiments and activity of Sol-gel alumina[J]. Advanced Synthesis & Catalysis, 2002, 344(8): 911-914
[59] SHEN Bin, LUO Min, ZHAO Lina, et al. First-principles calculation of SO₂ and NO₂ adsorbed on γ-Al₂O₃(110) surface[J]. Journal of Atomic and Molecular Physics, 2021, 38(1): 15-21(in Chinese) 沈彬, 罗敏, 赵丽娜, 等. SO₂和NO₂在γ-Al₂O₃(110)表面吸附的第一性原理计算[J]. 原子与分子物理学报, 2021, 38(1): 15-21
[60] LI Suidang, FU Jiquan. Novel synthesis technology of trimethylbenzoquinone by catalytic oxidation of pseudocumene[J]. Petrochemical Technology & Application, 2008, 26(3): 234-236(in Chinese) 李岁党, 傅吉全. 催化氧化偏三甲苯合成三甲基苯醌[J]. 石化技术与应用, 2008, 26(3): 234-236
[61] ZHANG Tianyong, DUAN Yongjie, LI Bin, et al. Synthesis of 2, 3, 5-trimethylbenzoquinone by catalytic oxidation of pseudocumene[J]. Chemical Reagents, 2013, 35(1): 3-6(in Chinese) 张天永, 段永洁, 李彬, 等. 偏三甲苯催化氧化法制备2, 3, 5-三甲基苯醌的研究[J]. 化学试剂, 2013, 35(1): 3-6
[62] ZHANG Tianyong, WANG Mengying, LI Bin, et al. Industrial packing γ-Al₂O₃ catalyzed oxidation of 1, 2, 4-trimethylbenzene to 2, 3, 5-trimethybenzoquinone[J]. Chinese Journal of Applied Chemistry, 2016, 33(10): 1161-1167(in Chinese) 张天永, 王梦颖, 李彬, 等. 工业填料γ-Al₂O₃催化氧化偏三甲苯制2, 3, 5-三甲基苯醌[J]. 应用化学, 2016, 33(10): 1161-1167
[63] ADAM W, HERRMANN W A, LIN J, et al. Catalytic oxidation of phenols to p-quinones with the hydrogen peroxide and methyltrioxorhenium(Ⅶ) system[J]. The Journal of Organic Chemistry, 1994, 59(26): 8281-8283
[64] ADAM W, HERRMANN W A, SAHA-MÖLLER C R, et al. Oxidation of methoxybenzenes to p-benzoquinones catalyzed by methyltrioxorhenium(Ⅶ)[J]. Journal of Molecular Catalysis A: Chemical, 1995, 97(1): 15-20
[65] KVHN F E, SCHERBAUM A, HERRMANN W A. Methyltrioxorhenium and its applications in olefin oxidation, metathesis and aldehyde olefination[J]. Journal of Organometallic Chemistry, 2004, 689(24): 4149-4164
[66] KVHN F E, SANTOS A M, HERRMANN W A. Organorhenium(Ⅶ) and organomolybdenum(Ⅵ) oxides: Syntheses and application in olefin epoxidation[J]. Dalton Transactions, 2005, (15): 2483-2491
[67] ROMÃO C C, KVHN F E, HERRMANN W A. Rhenium(Ⅶ) oxo and imido complexes: Synthesis, structures, and applications[J]. Chemical Reviews, 1997, 97(8): 3197-3246
[68] HANSEN P J, ESPENSON J H. Oxidation of chloride ions by hydrogen peroxide, catalyzed by methylrhenium trioxide[J]. Inorganic Chemistry, 1995, 34(23): 5839-5844
[69] HERRMANN W A, KVHN F E. Organorhenium oxides[J]. Accounts of Chemical Research, 1997, 30(4): 169-180
[70] MÓNICA C, ALTMANN P, BONRATH W, et al. Methyltrioxorhenium-catalysed oxidation of pseudocumene in the presence of amphiphiles for the synthesis of vitamin E[J]. Catalysis Science & Technology, 2012, 2(4): 722-724
[71] JACOB J, ESPENSON J H. Selective C-H bond activation of arenes catalyzed by methylrhenium trioxide[J]. Inorganica Chimica Acta, 1998, 270(1/2): 55-59
[72] CARRIL M, ALTMANN P, DREES M, et al. Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin E synthesis: A study of solvent and ligand effects[J]. Journal of Catalysis, 2011, 283(1): 55-67
[73] XU Z, ZHOU M, DREES M, et al. Mono- and bis- methyltrioxorhenium(Ⅶ) complexes with salen ligands: Synthesis, properties, applications[J]. Inorganic Chemistry, 2009, 48(14): 6812-6822
[74] ZHOU M, YU Y, CAPAPÉ A, et al. (N-salicylidene)aniline derived Schiff base complexes of methyltrioxorhenium(Ⅶ): Ligand influence and catalytic performance[J]. Chemistry-an Asian Journal, 2009, 4(3): 411-418
[75] KUDRIK E, SOROKIN A. N-bridged diiron phthalocyanine catalyzes oxidation of benzene with H₂O₂ via benzene oxide with NIH shift evidenced by using 1, 3, 5-[D3]benzene as a probe[J]. Chemistry-A European Journal, 2008, 14(24): 7123-7126
[76] NAKAGAWA Y, MIZUNO N. Mechanism of[γ-H₂SiV₂W₁₀O₄₀](4-)-catalyzed epoxidation of alkenes with hydrogen peroxide[J]. Inorganic Chemistry, 2007, 46(5): 1727-1736
[77] KAMATA K, YONEHARA K, NAKAGAWA Y, et al. Efficient stereo- and regioselective hydroxylation of alkanes catalysed by a bulky polyoxometalate[J]. Nature Chemistry, 2010, 2(6): 478-483
[78] FLOREA M, MARIN R S, PǎLǎANU F M, et al. Mesostructured vanadia-alumina catalysts for the synthesis of vitamin K3[J]. Catalysis Today, 2015, 254: 29-35
[79] PETROV L A, LOBANOVA N P, VOLKOV V L, et al. Catalytic properties of polyvanadomolybdic acids in oxidation of 1, 2, 4-trimethylbenzene by peracetic acid[J]. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 1989, 38(9): 1806-1809
[80] ZALOMAEVA O V, EVTUSHOK V Y, MAKSIMOV G M, et al. Selective oxidation of pseudocumene and 2-methylnaphthalene with aqueous hydrogen peroxide catalyzed by γ-Keggin divanadium-substituted polyoxotungstate[J]. Journal of Organometallic Chemistry, 2015, 793: 210-216