Замещенные цеолиты ZSM‑22: Сравнение физико-химических и каталитических свойств (обзор)

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Рұқсат ақылы немесе тек жазылушылар үшін

Аннотация

In this review, a comparative analysis of the literature on the synthesis, physicochemical, and catalytic properties of substituted ZSM-22 zeolites is presented. The physicochemical characteristics of Ce, Fe, Ga, B, and V substituted ZSM-22 samples are compared with those of the parent analog based on X-ray phase analysis, transmission electron microscopy, scanning electron microscopy, low-temperature nitrogen adsorption-desorption, FTIR spectroscopy of adsorbed pyridine, UV spectroscopy, X-ray photoelectron spectroscopy, temperature-programmed desorption of ammonia, and others. The possibility of using substituted ZSM-22 zeolites in the reactions of hydroisomerization of long-chain hydrocarbons, isomerization of butenes, methanol conversion to olefins, decomposition of nitrous oxide, disproportionation of ethylbenzene, and hydroxylation of arenes to phenols is demonstrated.

Авторлар туралы

V. Ostroumova

Institute of Petrochemical Synthesis named after A. V. Topchieva of RAS

Хат алмасуға жауапты Автор.
Email: ostroumova@ips.ac.ru
Moscow, 119991 Russia

Әдебиет тізімі

  1. Sai Prasad P.S., Bae J.W., Kang S.-H., Lee Y.-J., Jun K.-W. Single-step synthesis of DME from syngas on Cu-ZnO-Al2O3/zeolite bifunctional catalysts: the superiority of ferrierite over the other zeolites // Fuel Process. Technol. 2008. V. 89. № 12. P. 1281–1286. http://dx.doi.org/10.1016/j.fuproc.2008.07.014
  2. https://europe.iza-structure.org/IZA-SC/framework. php? ID=239
  3. Del Campo P., Olsbye U., Lillerud K.P., Svelle S., Beato P. Impact of post-synthetic treatments on unidirectional H-ZSM-22 zeolite catalyst: towards improved clean MTG catalytic process // Catal. Today. 2018. V. 299. P. 135–145. https://doi.org/10.1016/j.cattod.2017.05.011
  4. Gao S.-B., Zhao Z., Lu X.-F., Chi K.-B., Duan A.J., Liu Y.-F., Meng X.-B., Tan M.-W., Yu H.-Y., Shen Y.-G., Li M.-C. Hydrocracking diversity in n-dodecane isomerization on Pt/ZSM-22 and Pt/ZSM-23 catalysts and their catalytic performance for hydrodewaxing of lube base oil // Pet. Sci. 2020. V. 17. P. 1752–1763. https://doi.org/10.1007/s12182-020-00500-7
  5. Redekop E.A., Lazzarinia A., Bordigaa S., Olsbey U. A temporal analysis of products (TAP) study of C2-C4 alkene reactions with a well-defined pool of methylating species on ZSM-22 zeolite // J. Catal. 2020. V. 385. P. 300–312. https://doi.org/10.1016/j.jcat.2020.03.020
  6. Liu Z., Chu Y., Tang X., Huang L., Li G., Yi X., Zheng A. Diffusion dependence of the dual-cycle mechanism for MTO reaction inside ZSM-12 and ZSM-22 // J. Phys. Chem. C. 2017. V. 121. № 41. P. 22872–22882. https://doi.org/10.1021/acs.jpcc.7b07374
  7. Valyocsik E.W. Synthesis of zeolite ZSM-22. 1984. US Patent No 4902406. https://patentimages.storage.googleapis.com/b5/79/a5/6c83073872b042/US4902406.pdf
  8. Verdujin J.P., Martens L.R.M. ZSM-22 zeolite. US Patent No 5783168. https://patentimages.storage.googleapis.com/a9/e3/ff/dfe25bc56bcbc62b/US5783168.pdf
  9. de Sousa L.V., Ribeiro T.R.S., da Silva B.J.B., Quintela P.H.L., Alencar S.L., de Pacheco Filha J.G.A., de Silva A.O.S. Different approaches to the synthesis of ZSM-22 zeolite with application in n-heptane cracking // Res. Soc. Develop. 2022. V. 11. № 3. P. 1–17. http://dx.doi.org/10.33448/rsd-v11i3.26070
  10. Nishiyama N., Ueyama K., Matsukata M. Synthesis of defect-free zeolite-alumina composite membranes by a vapor-phase transport method // Micropor. Mater. 1996. V. 7. № 6. P. 299–308. https://doi.org/10.1016/S0927-6513(96)00053-3
  11. Sato S., Yu-u Y., Yahiro H., Mizuno N., Iwamoto M. Cu-ZSM-5 zeolite as highly active catalyst for removal of nitrogen monoxide from emission of diesel engines // Appl. Catal. 1991. V. 70. № 1. P. L1–L5. https://doi.org/10.1016/S0166-9834(00)84146-9
  12. Noreña-Franco L., Hernandez-Perez I., Aguilar-Pliego J., Maubert-Franco A. Selective hydroxylation of phenol employing Cu–MCM-41 catalysts // Catal. Today. 2002. V. 75. № 1–4. P. 189–195. https://doi.org/10.1016/S0920-5861(02)00067-6
  13. Weitkamp J. Isomerization of long-chain n-alkanes on a Pt/CaY zeolite catalyst // Ind. Eng. Chem. Prod. Res. Dev. 1982. V. 21. № 4. P. 550–558. https://doi.org/10.1021/i300008a008
  14. Mériaudeau P., Tuan V.A., Nghiem V.T., Lai S.Y., Hung L.N., Naccache C. SAPO-11, SAPO-31, and SAPO-41 molecular sieves: synthesis, characterization, and catalytic properties in n-octane hydroisomerization // J. Catal. 1982. V. 169. № 1. P. 55–66. https://doi.org/10.1006/jcat.1997.1647
  15. Parmar S., Pant K.K., John M., Kumar K., Pal S.M., Newalkar B.L. Hydroisomerization of n-hexadecane over Pt/ZSM-22 framework: Effect of divalent cation exchange // J. Mol. Catal. A: Chem. 2015. V. 404–405. P. 47–56. https://doi.org/10.1016/j.molcata.2015.04.012
  16. Wu X., Qiu M., Chen X., Yu G., Yu X., Yang Ch., Sun J., Liu Z., Sun Y. Enhanced n-dodecane hydroisomerization performance by tailoring acid sites on bifunctional Pt/ZSM-22 via alkaline treatment // New J. Chem. 2018. V. 42. P. 111–117. https://doi.org/10.1039/C7NJ03417B
  17. Liu S.Y., Zhang L., Zhang L., Zhang H.K., Ren J., Function of well-established mesoporous layers of recrystallized ZSM-22 zeolites in the catalytic performance of n-alkane isomerization // New J. Chem. 2020. V. 44. P. 4744–4754. https://doi.org/10.1039/C9NJ06273D
  18. Liu S.Y., Ren J., Zhang H.K., Lv E.J., Yang Y., Li Y.W. Synthesis, characterization and isomerization performance of micro/mesoporous materials based on H-ZSM-22 zeolite // J. Catal. 2016. V. 335. P. 11–23. https://doi.org/10.1016/j.jcat.2015.12.009
  19. Chi K., Zhao Zh., Tian Zh., Hu Sh., Yan L., Li T., Wang B., Meng X., Gao Sh., Tan M., Liu Y. Hydroisomerization performance of platinum supported on ZSM-22/ZSM-23 intergrowth zeolite catalyst // Pet. Sci. 2013. V. 10. P. 242–250. https://doi.org/10.1007/s12182-013-0273-6
  20. Burton A.W., Zones S.I., Rea T., Chan I.Y. Preparation and characterization of SSZ-54: A family of MTT/TON intergrowth materials // Micropor. Mesopor. Mater. 2010. V. 132. № 1–2. P. 54–59. https://doi.org/10.1016/j.micromeso.2009.10.023
  21. Munusamy K., Das R.K., Ghosh S., Kishore Kumar S.A., Pai S., Newalkar B.L. Synthesis, characterization and hydroisomerization activity of ZSM-22/23 intergrowth zeolite // Micropor. Mesopor. Mater. 2018. V. 266. P. 141–148. https://doi.org/10.1016/j.micromeso.2018.02.044
  22. Wang Q., Sim L.B., Xie J., Ye S., Fu J., Wang J., Zhang N., Zheng J., Chen B. Promotion effect of cerium in ZSM-22 zeolite on the hydroisomerization of n-hexadecane // Micropor. Mesopor. Mater. 2023. V. 360. ID 112720. https://doi.org/10.1016/j.micromeso.2023.112720
  23. Liu S.Y., Ren J., Zhu S., Zhang H.K., Lv E.J., Xu J., Li Y.W. Synthesis and characterization of the Fe-substituted ZSM-22 zeolite catalyst with high n-dodecane isomerization performance // J. Catal. 2015. V. 330. P. 485–496. https://doi.org/10.1016/j.jcat.2015.07.027
  24. Liu S.Y., He Y.R., Zhang H.K., Chen Z.Q., Lv E.J., Ren J., Yun Y.F., Wen X.D., Li Y.W. Design and synthesis of Ga-doped ZSM-22 zeolites as highly selective and stable catalysts for n-dodecane isomerization // Catal. Sci. Technol. 2019. V. 9. P. 2812–2827. https://doi.org/10.1039/C9CY00414A
  25. Singh A.P., Reddy K.R. Synthesis, characterization, and catalytic activity of gallosilicate analogs of zeolite ZSM-22 // Zeolites. 1994. V. 14. № 4. P. 290–294. https://doi.org/10.1016/0144-2449(94)90098-1
  26. Verboekend D., Thomas K., Milina M., Mitchell S., Pérez-Ramirez., Gilson J.-P. Towards more efficient monodimensional zeolite catalysts: n-alkane hydro-isomerization on hierarchical ZSM-22 // Catal. Sci. Technol. 2011. V. 1. P. 1331–1335. https://doi.org/10.1039/C1CY00240F
  27. Dooley K.M., Chang C., Price G.L. Effects of pretreatments on state of gallium and aromatization activity of gallium/ZSM-5 catalysts // Appl. Catal. A: Gen. 1992. V. 84. № 1. P. 17–30. https://doi.org/10.1016/0926-860X(92)80336-B
  28. Masih D., Kobayashi T., Baba T. Hydrothermal synthesis of pure ZSM-22 under mild conditions // Chem. Commun. 2007. № 31. P. 3303–3305. https://doi.org/10.1039/B704787H
  29. Chandwadkar A.J., Bhat R.N., Ratnasamy P. Synthesis of iron-silicate analogs of zeolite mordenite // Zeolites. 1991. V. 11. № 1. P. 42–47. https://doi.org/10.1016/0144-2449(91)80354-3
  30. Luo Y., Wang Z., Jin S., Zhang B., Sun H., Yuan X., Yang W. Synthesis and crystal growth mechanism of ZSM-22 zeolite nanosheets // CrystEngCom, 2016. V. 18. № 30. P. 5611–5615. https://doi.org/10.1039/C6CE00773B
  31. Kumar N., Lindfors L.E., Byggningsbacka R. Synthesis and characterization of H-ZSM-22, Zn-H-ZSM-22 and Ga-H-ZSM-22 zeolite catalysts and their catalytic activity in the aromatization of n-butane // Appl. Catal. A: Gen. 1996. V. 139. № 1–2. P. 189–199. https://doi.org/10.1016/0926-860X(95)00327-4
  32. Zhou H., Zhu W., Shi L., Liu H., Liu S.P., Xu S.T., Ni Y., Liu Y., Li L., Liu Z. Promotion effect of Fe in mordenite zeolite on carbonylation of dimethyl ether to methyl acetate // Catal. Sci. Technol. 2015. V. 5. P. 1961–1968. https://doi.org/10.1039/C4CY01580K
  33. Li Y., Huang S.Y., Cheng Z.Z., Cai K., Li L.D., Milan E., Lv J., Wang Y., Sun Q., Ma X.B. Promoting the activity of Ce-incorporated MOR in dimethyl ether carbonylation through tailoring the distribution of Brønsted acids // Appl. Catal. B: Environ. 2019. V. 56. ID 117777. https://doi.org/10.1016/j.apcatb.2019.117777
  34. Calis G., Frenken P., de Boer F., Swolfs A., Hefni M.A. Synthesis and spectroscopic studies of Fe3+ substituted ZSM-5 zeolite // Zeolites. 1987. V. 7. № 4. P. 319–326. https://doi.org/10.1016/0144-2449(87)90034-0
  35. Loeffler E., Peuker C., JerSchkewitz. The influence of dealumination on the infrared spectra of H-ZSM-5 // Catal. Today. 1988. V. 3. № 5. P. 415–420. https://doi.org/10.1016/0920-5861(88)87023-8
  36. Lanh H.D., Tuan V.A., Kosslick H., Parlitz B., Fricke R., Vólter J. n-Hexane aromatization on synthetic gallosilicates with MFI structure // Appl. Catal. A: Gen. 1993. V. 103. № 2. P. 205–222. https://doi.org/10.1016/0926-860X(93)85052-Q
  37. Wu Y.J., Wang J., Liu P., Zhang W., Gu J., Wang X.J. Framework-substituted lanthanide MCM-22 zeolite: synthesis and characterization // J. Am. Chem. Soc. 2010. V. 132. № 51. P. 17989–17991. https://doi.org/10.1021/ja107633j
  38. Anandan C., Bera P. XPS studies on the interaction of CeO2 with silicon in magnetron sputtered CeO2 thin films on Si and Si3N4 substrates // Appl. Surf. Sci. 2013. V. 283. P. 297–303. https://doi.org/10.1016/j.apsusc.2013.06.104
  39. Inui T., Nagata H., Takeguchi T., Iwamoto S., Matsuda H., Inoue M. Environments of iron in Fe-silicates synthesized by the rapid crystallization method // J. Catal. 1993. V. 139. № 2. P. 482–489. https://doi.org/10.1006/jcat.1993.1042
  40. Hensen E.J.M., Zhu Q., Janssen R.A.J., Magusin P.C.M.M., Kooyman P.J., van Santen R.A. Selective oxidation of benzene to phenol with nitrous oxide over MFI zeolites: 1. On the role of iron and aluminum // J. Catal. 2005. V. 233. № 1. P. 123–135. https://doi.org/10.1016/j.jcat.2005.04.009
  41. Bordiga S., Buzzoni R., Geobaldo F., Lamberti C., Giamello E., Zecchina A., Leofanti G., Petrini G., Tozzola G., Vlaic G. Structure and reactivity of framework and extraframework iron in Fe-silicalite as investigated by spectroscopic and physicochemical methods // J. Catal. 1996. V. 158. № 2. P. 486–501. https://doi.org/10.1006/jcat.1996.0048
  42. Fejes P., Nagy J.B., Halász J., Oszkó A. Heat-treatment of isomorphously substituted ZSM-5 zeolites and its structural consequences: An X-ray diffraction,29Si MAS-NMR, XPS and FT-IR spectroscopy study // Appl. Catal. A: Gen. 1998. V. 175. № 1–2. P. 89–104. https://doi.org/10.1016/S0926–860X(98)00212-9
  43. Zhang H., Chu L., Xiao Q., Zhu L., Yang Ch., Meng X., Xiao F.-S. One-pot synthesis of Fe-Beta zeolite by an organotemplate-free and seed-directed route // J. Mater. Chem. A. 2013. V. 1. P. 3254–3257. https://doi.org/10.1039/C3TA01238G
  44. Yang W.C., Li C.F., Wang H.Y., Li X.Y., Zhang W.I., Li H.L. Cobalt doped ceria for abundant storage of surface-active oxygen and efficient elemental mercury oxidation in coal combustion flue gas // Appl. Catal. B: Environ. 2018. V. 239. P. 233–244. https://doi.org/10.1016/j.apcatb.2018.08.014
  45. Qing M., Yang Y., Wu B., Xu J., Zhang C., Gao P., Li Y. Modification of Fe–SiO2 interaction with zirconia for iron-based Fischer–Tropsch catalysts // J. Catal. 2011. V. 279. № 1. P. 111–122. https://doi.org/10.1016/j.jcat.2011.01.005
  46. Seyma H., Wang D., Soma M. X-ray photoelectron microscopic imaging of the chemical bonding state of Si in a rock sample // Surf. Interface Anal. 2004. V. 36. № 7. P. 609–612. https://doi.org/10.1002/sia.1784
  47. Kumar R., Ratnasamy P. Isomorphous substitution of iron in the framework of zeolite ZSM-23 // J. Catal. 1990. V. 121. № 1. P. 89–98. https://doi.org/10.1016/0021-9517(90)90219-A
  48. Gawande M.B., Deshpande S.S., Sonavane S.U., Jayaram R.V. A novel sol–gel synthesized catalyst for Friedel–Crafts benzoylation reaction under solvent-free conditions // J. Mol. Catal. A: Chem. 2005. V. 241. № 1–2. P. 151–155. https://doi.org/10.1016/j.molcata.2005.06.069
  49. Zhang F., Du N., Li H., Liang X., Hou W. Sorption of Cr(VI) on Mg-Al-Fe layered double hydroxides synthesized by a mechanochemical method // RSC Adv. 2014. V. 4. P. 46823–46830. https://doi.org/10.1039/C4RA07553F
  50. Diaz Y., Melo L., Mediavilla M., Albornoz A., Brito J.L. Characterization of bifunctional Pt/H[Ga]ZSM5 and Pt/H[Al]ZSM5 catalysts: II. Evidences of a Pt–Ga interaction // J. Mol. Catal. A: Chem. 2005. V. 227. № 1–2. P. 7–15. https://doi.org/10.1016/j.molcata.2004.09.050
  51. Price G.L., Kanazirev V. Ga2O3/HZSM-5 propane aromatization catalysts: Formation of active centers via solid-state reaction // J. Catal. 1990. V. 126. P. 267–278. https://doi.org/10.1016/0021-9517(90)90065-R
  52. Li M., Zhou Y., Oduro I.N., Fang Y. Comparative study on the catalytic conversion of methanol and propanal over Ga/ZSM-5 // Fuel. 2016. V. 168. P. 68–75. https://doi.org/10.1016/j.fuel.2015.11.076
  53. Kim M.Y., Lee K., Choi M. Cooperative effects of secondary mesoporosity and acid site location in Pt/SAPO-11 on n-dodecane hydroisomerization selectivity // J. Catal. 2014. V. 319. P. 232–238. https://doi.org/10.1016/j.jcat.2014.09.001
  54. Yang X., Ma H., Xu Z., Xu Y., Tian Z., Lin L. Hydroisomerization of n-dodecane over Pt/MeAPO-11 (Me = Mg, Mn, Co or Zn) catalysts // Catal. Commun. 2007. V. 8. № 8. P. 1232–1238. https://doi.org/10.1016/j.catcom.2006.11.005
  55. Segawa K., Hiroyasu T. Highly selective methylamine synthesis over modified mordenite catalysts // J. Catal. 1991. V. 131. № 2. P. 482–490. https://doi.org/10.1016/0021-9517(91)90280-H
  56. Yuan S.P., Wang J.G., Li Y.W., Peng S.Y. Theoretical studies on the properties of acid site in isomorphously substituted ZSM-5 // J. Mol. Catal. A: Chem. 2002. V. 178. № 1–2. P. 267–274. https://doi.org/10.1016/S1381-1169(01)00335-1
  57. Chatterjee A., Iwasaki T., Ebina T., Miyamoto A. Theoretical studies on the properties of acid site in isomorphously substituted ZSM-5 // Micropor. Mesopor. Mater. 1998. V. 21. № 4–6. P. 421–428. https://doi.org/10.1016/S1387-1811(98)00051-1
  58. Matsuura H., Katada N., Niwa M. Additional acid site on HZSM-5 treated with basic and acidic solutions as detected by temperature-programmed desorption of ammonia // Micropor. Mesopor. Mater. 2003. V. 66. № 1–2. P. 283–296. https://doi.org/10.1016/j.micromeso.2003.09.020
  59. Challoner R., Harris R.K., Barri S.A.I., Taylor M.J. An investigation of Brönsted acidity in gallosilicate-MFI (Ga-ZSM-5) // Zeolites. 1995. V. 11. № 8. P. 827–831. https://doi.org/10.1016/S0144-2449(05)80063-6
  60. Inui T., Matsuba K., Tanaka Y. Comprehensive description of the acidic property of effective metallosilicate catalysts by computer simulation // Catal. Today. 1995. V. 23. № 4. P. 317–323. https://doi.org/10.1016/0920-5861(94)00144-Q
  61. Guo L., Bao X., Fan Y., Shi G., Liu H., Bai D. Impact of cationic surfactant chain length during SAPO-11 molecular sieve synthesis on structure, acidity, and n-octane isomerization to di-methyl hexanes // J. Catal. 2012. V. 294. P. 161–170. https://doi.org/10.1016/j.jcat.2012.07.016
  62. Zeng S., Blanchard J., Breysse M., Shi Y., Shu X., Nie H., Li D. Post-synthesis alumination of SBA-15 in aqueous solution: A versatile tool for the preparation of acidic Al-SBA-15 supports // Micropor. Mesopor. Mater. 2005. V. 85. № 3. P. 297–304. https://doi.org/10.1016/j.micromeso.2005.06.031
  63. Camblor M.A., Pe rez-Pariente J., Forne V. Synthesis and characterization of gallosilicates and galloaluminosilicates isomorphous to zeolite Beta // Zeolites. 1992. V. 12. № 3. P. 280–286. https://doi.org/10.1016/S0144-2449(05)80296-9
  64. Strodel P., Neyman K.M., Knözinger H., Rösch N. Acidic properties of [Al], [Ga] and [Fe] isomorphously substituted zeolites. Density functional model cluster study of the complexes with a probe CO molecule // Chem. Phys. Lett. 1995. V. 240. № 5–6. P. 547–552. https://doi.org/10.1016/0009-2614(95)00583-P
  65. Knaeble W., Carr R.T., Iglesia E. Mechanistic interpretation of the effects of acid strength on alkane isomerization turnover rates and selectivity // J. Catal. 2014. V. 319. P. 283–296. https://doi.org/10.1016/j.jcat.2014.09.005
  66. Chen Y., Li C., Chen X., Liu Y., Tsang C.-W., Liang C. Synthesis and characterization of iron-substituted ZSM-23 zeolite catalysts with highly selective hydroisomerization of n-hexadecane // Ind. Eng. Chem. Res. 2018. V. 57. № 41. P. 13721–13730. https://doi.org/10.1021/acs.iecr.8b03806
  67. Noh G., Shi Z., Zones S.I., Iglesia E. Isomerization and β-scission reactions of alkanes on bifunctional metal-acid catalysts: consequences of confinement and diffusional constraints on reactivity and selectivity // J. Catal. 2018. V. 368. P. 389–410. https://doi.org/10.1016/j.jcat.2018.03.033
  68. Wang G., Liu Q., Su W., Li X., Jiang Z., Fang X., Han C., Li C. Hydroisomerization activity and selectivity of n-dodecane over modified Pt/ZSM-22 catalysts // Appl. Catal. A: Gen. 2008. V. 335. № 1. P. 20–27. https://doi.org/10.1016/j.apcata.2007.11.002
  69. Jamil A.K., Muraza O., Miyake K., Ahmed M.H.M., Yamani Z.H., Hirota Y., Nishiyama N. Stable production of gasoline-ranged hydrocarbons from dimethyl ether over iron-modified ZSM-22 zeolite // Energу Fuels. 2018. V. 32. № 11. P. 11796–11801. https://doi.org/10.1021/acs.energyfuels.8b03008
  70. Jamil A.K., Muraza O., Yoshioka M., Al-Amer A., Yamani Z.H., Yokoi T. Selective production of propylene from methanol conversion over nanosized ZSM-22 zeolites // Ind. Eng. Chem. Res. 2014. V. 53. № 50. P. 19498–19505. https://doi.org/10.1021/ie5038006
  71. Jamil A.K., Nishitoba T., Ahmed M.H.M., Yamani Z.H., Yokoi T., Muraza O. Stable boron-modified ZSM-22 zeolite catalyst for selective production of propylene from methanol // Energy Fuels. 2019. V. 33. № 12. P. 12679–12684. https://doi.org/10.1021/acs.energyfuels.9b03009
  72. Wang S., Li S., Zhang L., Qin Z., Dong M., Li J., Wang J., Fan W. Insight into the effect of incorporation of boron into ZSM-11 on its catalytic performance for conversion of methanol to olefins // Catal. Sci. Technol. 2017. V. 7. № 20. P. 4766–4779. https://doi.org/10.1039/C7CY01428G
  73. Zhu Q., Kondo J.N., Yokoi T., Setoyama T., Yamaguchi M., Takewaki T., Domen K., Tatsum T. The influence of acidities of boron- and aluminium-containing MFI zeolites on co-reaction of methanol and ethene // Phys. Chem. Chem. Phys. 2011. V. 13. № 32. P. 14598–14605. https://doi.org/10.1039/C1CP20338J
  74. Chen J., Liang T., Li J., Wang S., Qin Z., Wang P., Huang L., Fan W., Wang J. Regulation of framework aluminum siting and acid distribution in H-MCM-22 by boron incorporation and its effect on the catalytic performance in methanol to hydrocarbons // ACS Catal. 2016. V. 6. № 4. P. 2299–2313. https://doi.org/10.1021/acscatal.5b02862
  75. Jamil A.K., Muraza O., Ahmed M.H., Zainalabdeen A., Muramoto K., Nakasaka Y., Yamani Z.H., Yoshikawa T., Masuda T. Hydrothermally stable acid-modified ZSM-22 zeolite for selective propylene production via steam-assisted catalytic cracking of n-hexane // Micropor. Mesopor. Mater. 2018. V. 260. P. 30–39. https://doi.org/10.1016/j.micromeso.2017.10.016
  76. Ma M., Huang X., Zhan E., Zhou Y., Xue H., Shen W. Synthesis of mordenite nanosheets with shortened channel lengths and enhanced catalytic activity // J. Mater. Chem. A. 2017. V. 5. № 19. P. 8887–8891. https://doi.org/10.1039/C7TA02477K
  77. Hu Z., Zhang H., Wang L., Zhang H., Zhang Y., Xu H., Shen W., Tang Y. Highly stable boron-modified hierarchical nanocrystalline ZSM-5 zeolite for the methanol to propylene reaction // Catal. Sci. Technol. 2014. V. 4. № 9. P. 2891–2895. https://doi.org/10.1039/C4CY00376D
  78. Asensi M.A., Corma A., Martinez A., Derewinski M., Krysciak J., Tamhankar S.S. Isomorphous substitution in ZSM-22 zeolite. The role of zeolite acidity and crystal size during the skeletal isomerization of n-butene // Appl. Catal. A: Gen. 1998. V. 174. № 1–2. P. 163–175. https://doi.org/10.1016/S0926-860X(98)00166-5
  79. Kasture M., Krysciak J., Matachowski L., Machej T., Derewifiski M. Nitrous oxide decomposition over iron exchanged [AI]- and [Fe]-ZSM-22 // Stud. Surf. Sci. Catal. 1999. V. 125. P. 579–586. https://doi.org/10.1016/S0167-2991(99)80262-6
  80. Kapteijn F., Rodriguez-Mirasol J., Moulijn J.A. Heterogeneous catalytic decomposition of nitrous oxide // Appl. Catal. B: Environ. 1996. V. 9. № 1–4. P. 25–64. https://doi.org/10.1016/0926-3373(96)90072-7
  81. Kumar R., Patnasamy P. Isomerization and formation of xylenes over ZSM-22 and ZSM-23 zeolites // J. Catal. 1989. V. 116. № 2. P. 440–448. https://doi.org/10.1016/0021-9517(89)90110-3
  82. Kokotailo G.T., Schlenker J.L., Dwyer F.G., Valyocsik E.W. The framework topology of ZSM-22: a high silica zeolite // Zeolites 1985. V. 5. № 6. P. 349–351. https://doi.org/10.1016/0144-2449(85)90122-8
  83. Kustov L.M., Kazansky V.B., Raatnasamy P. Spectroscopic investigation of iron ions in a novel ferrisilicate pentasil zeolite // Zeolites. 1987. V. 7. № 1. P. 79–83. https://doi.org/10.1016/0144-2449(87)90125-4
  84. Szostak R., Thomas T.L. Reassessment of zeolite and molecular sieve framework infrared vibrations // J. Catal. 1986. V. 101. № 2. P. 549–552. https://doi.org/10.1016/0021-9517(86)90286-1
  85. Montes A., Perot G., Guisnet M. Cracking of n-hexane on Na, H-mordenite: Coke poisoning // React. Kinet. Catal. Lett. 1985. V. 29. P. 79–84. https://doi.org/10.1007/BF02067952
  86. Chu C.T.W., Chang C.D. Isomorphous substitution in zeolite frameworks. 1. Acidity of surface hydroxyls in [B]-, [Fe]-, [Ga]-, and [Al]-ZSM-5 // J. Phys. Chem. 1985. V. 89. № 9. P. 1569–1571. https://doi.org/10.1021/j100255a005
  87. Yuan C., Liang Y., Hernandez T., Berriochoa A., Houl K.N., Siegel D. Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism // Nature. 2013. V. 499. P. 192–196. https://doi.org/10.1038/nature12284
  88. Qian W., Yan D., Chen Y., Wang T., Xiong F., Wei W., Lu Y., Sun W.-Y., Li J.J., Zhao J. A redox-neutral catechol synthesis // Nat. Commun. 2017. V. 8. ID 14227. https://doi.org/10.1038/ncomms14227
  89. Niwa S., Muthusamy E., Nair J., Raj A., Itoh N., Shoji H., Namba T., Mizukami F. A one-step conversion of benzene to phenol with a palladium membrane // Science. 2002. V. 295. № 5552. P. 105–107. https://doi.org/10.1126/science.1066527
  90. Shoji O., Yanagisawa S., Stanfield J.K., Suzuki K., Cong Z., Sugimoto H., Shiro Y., Watanabe Y. Direct hydroxylation of benzene to phenol by cytochrome P450BM3 triggered by amino acid derivatives // Angew. Chem. Int. Ed. 2017. V. 56. № 35. P. 10324–10329. https://doi.org/10.1002/anie.201703461
  91. Zheng Y.-W., Chen B., Ye P., Feng K., Wang W., Meng Q.-Y., Wu L.-Z., Tung C.-H. Photocatalytic hydrogen-evolution cross-couplings: benzene C–H amination and hydroxylation // J. Am. Chem. Soc. 2016. V. 138. № 32. P. 10080–10083. https://doi.org/10.1021/jacs.6b05498
  92. Meng L., Zhu X., Hensen E.J.M. Stable Fe/ZSM-5 nanosheet zeolite catalysts for the oxidation of benzene to phenol // ACS Catal. 2017. V. 7. № 4. P. 2709–2719. https://doi.org/10.1021/acscatal.6b03512
  93. Borah P., Ma X., Nguyen K.T., Zhao Y. A Vanadyl complex grafted to periodic mesoporous organosilica: a green catalyst for selective hydroxylation of benzene to phenol // Angew. Chem. Int. Ed. 2012. V. 51. № 31. P. 7756–7761. https://doi.org/10.1002/anie.201203275
  94. Xiong F., Lu L., Sun T.-Y., Wu Q., Yan D., Chen Y., Zhang X., Wei W., Lu Y., Sun W.-Y., Li J.J., Zhao J. A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis // Nat. Commun. 2017. V. 8. ID15912. https://doi.org/10.1038/ncomms15912
  95. Deng D., Chen X., Yu L., Wu X., Liu Q., Liu Y., Yang H., Tian H., Hu Y., Du P., Si R., Wang J., Cui X., Li H., Xiao J., Xu T., Deng J., Yang F., Duchesne P.N., Zhang P., Zhou J., Sun L., Li J., Pan X., Bao X. A single iron site confined in a graphene matrix for the catalytic oxidation of benzene at room temperature // Sci. Adv. 2015. V. 1. № 11. Art. ID e1500462. https://doi.org/10.1126/sciadv.1500462
  96. Kuhl N., Hopkinson M.N., Wencel-Delord J., Glorius F. Beyond directing groups: transition-metal-catalyzed C–H activation of simple arenes // Angew. Chem. Int. Ed. 2012. V. 51. № 41. P. 10236–10254. https://doi.org/10.1002/anie.201203269
  97. Yi H., Zhang G., Wang H., Huang Z., Wang J., Singh A.K., Lei A. Recent advances in radical C–H activation/radical cross-coupling // Chem. Res. 2017. V. 117. № 13. P. 9016–9085. https://doi.org/10.1021/acs.chemrev.6b00620
  98. Yamada M., Karlin K.D., Fukuzumi S. One-step selective hydroxylation of benzene to phenol with hydrogen peroxide catalyzed by copper complexes incorporated into mesoporous silica–alumina // Chem. Sci. 2016. V. 7. P. 2856–2863. https://doi.org/10.1039/C5SC04312C
  99. Tian K., Liu W.-J., Zhang S., Jiang H. One-pot synthesis of a carbon supported bimetallic Cu–Ag NPs catalyst for robust catalytic hydroxylation of benzene to phenol by fast pyrolysis of biomass waste // Green Chem. 2016. V. 18. P. 5643–5650. https://doi.org/10.1039/C6GC01231K
  100. Wang S.-S., Yang G.-Y. Recent advances in polyoxometalate-catalyzed reactions // Chem. Res. 2015. V. 15. № 11. P. 4893–4962. https://doi.org/10.1021/cr500390v
  101. Khatri P.K., Singh B., Jain S.L., Sain B., Sinha A.K. Cyclotriphosphazene grafted silica: a novel support for immobilizing the oxo-vanadium Schiff base moieties for hydroxylation of benzene // Chem. Commun. 2011. V. 47. P. 1610–1612. https://doi.org/10.1039/C0CC01941K
  102. Tanev P.T., Chibwe M., Pinnavaia T. Titanium-containing mesoporous molecular sieves for catalytic oxidation of aromatic compounds // Nature. 1994. V. 368. P. 321–323. https://doi.org/10.1038/368321a0
  103. Vedernikov A.N. Direct functionalization of M–C (M = PtII, PdII) bonds using environmentally benign oxidants, O2 and H2O2 // Acc. Chem. Res. 2012. V. 45. № 6. P. 803–813. https://doi.org/10.1021/ar200191k
  104. Wen G., Wu Sh., Li B., Dai C., Su D.S. Active sites and mechanisms for direct oxidation of benzene to phenol over carbon catalysts // Angew. Chem. Int. Ed. 2015. V. 54. № 13. P. 4105–4109. https://doi.org/10.1002/anie.201410093
  105. Morimoto Y., Bunno S., Fujieda N., Sugimoto H., Itoh S. Direct hydroxylation of benzene to phenol using hydrogen peroxide catalyzed by nickel complexes supported by pyridylalkylamine ligands // J. Am. Chem. Soc. 2015. V. 137. № 18. P. 5867–5870. https://doi.org/10.1021/jacs.5b01814
  106. Hartman M., Machoke A.G., Schwieger W. Catalytic test reactions for the evaluation of hierarchical zeolites // Chem. Soc. Rev. 2016. V. 45. P. 3313–3330. https://doi.org/10.1039/C5CS00935A
  107. Kamata K., Yamaura T., Mizuno N. Chemo- and regioselective direct hydroxylation of arenes with hydrogen peroxide catalyzed by a divanadium-substituted phosphotungstate // Angew. Chem. Int. Ed. 2012. V. 51. № 29. P. 7275–7278. https://doi.org/10.1002/anie.201201605
  108. Leng Y., Wang J., Zhu D., Shen L., Zhao P., Zhang M. Heteropolyanion-based ionic hybrid solid: A green bulk-type catalyst for hydroxylation of benzene with hydrogen peroxide // Chem. Eng. J. 2011. V. 173. № 2. P. 620–626. https://doi.org/10.1016/j.cej.2011.08.013
  109. Li C., Zheng P., Li J., Zhang H., Cui Y., Shao Q., Ji X., Zhang J., Zhao P., Xu Y. The dual roles of oxodiperoxovanadate both as a nucleophile and an oxidant in the green oxidation of benzyl alcohols or benzyl halides to aldehydes and ketones // Angew. Chem. Int. Ed. 2003. V. 42. № 41. P. 5063–5066. https://doi.org/10.1002/anie.200351902
  110. Mimoun H., Saussine L., Daire E., Postel M., Fischer J., Weiss R. Vanadium(V) peroxy complexes. New versatile biomimetic reagents for epoxidation of olefins and hydroxylation of alkanes and aromatic hydrocarbons // J. Am. Chem. Soc. 1983. V. 105. № 10. P. 3101–3110. https://doi.org/10.1021/ja00348a025
  111. Zhou Y., Ma Z., Tang J. Yan N., Du Y., Xi S. Wang K., Zhang W., Wen H., Wang J. Immediate hydroxylation of arenes to phenols via V-containing all-silica ZSM-22 zeolite triggered non-radical mechanism // Nat. Commun. 2018. V. 9. ID 2931. https://doi.org/10.1038/s41467-018-05351-w
  112. Zhang W., Xie J., Hou W., Liu Y., Zhou Y., Wang J. One-pot template-free synthesis of Cu–MOR zeolite toward efficient catalyst support for aerobic oxidation of 5-hydroxymethylfurfural under ambient pressure // ACS Appl. Mater. Interfaces. 2016. V. 8. № 36. P. 23122–23132. https://doi.org/10.1021/acsami.6b07675
  113. Shi J., Wang Y., Wang W., Tang Y., Xie Z. Recent advances of pore system construction in zeolite-catalyzed chemical industry processes // Chem. Soc. Rev. 2015. V. 44. P. 8877–8903. https://doi.org/10.1039/C5CS00626K
  114. Sun Q., He H., Gao W.-Y., Aguila B., Woitas L., Dai Z., Li J., Chen Y.-S., Xiao F.-S., Ma S. Imparting amphiphobicity on single-crystalline porous materials // Nat. Commun. 2016. V. 7. ID 13300. https://doi.org/10.1038/ncomms13300
  115. Wang L., Wang G., Zhang J., Bian C., Meng X., Xiao F.-S. Controllable cyanation of carbon-hydrogen bonds by zeolite crystals over manganese oxide catalyst // Nat. Commun. 2017. V. 8. ID 15240. https://doi.org/10.1038/ncomms15240
  116. (а) (б)

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
Жүктеу

© Russian Academy of Sciences, 2025