Synthesis of Silicalite-1 hollow sphere catalyst and its application for Beckmann rearrangement reaction

JIN Ya-mei; DONG Mei; WANG Guo-fu; WANG Hao; LI Jun-fen; FAN Wei-bin; WANG Jian-guo; QIN Zhang-feng

Volume 44 Issue 8

Aug. 2016

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Article Navigation > Journal of Fuel Chemistry and Technology > 2016 > 44(8): 1001-1009

JIN Ya-mei, DONG Mei, WANG Guo-fu, WANG Hao, LI Jun-fen, FAN Wei-bin, WANG Jian-guo, QIN Zhang-feng. Synthesis of Silicalite-1 hollow sphere catalyst and its application for Beckmann rearrangement reaction[J]. Journal of Fuel Chemistry and Technology, 2016, 44(8): 1001-1009.

Citation:

JIN Ya-mei, DONG Mei, WANG Guo-fu, WANG Hao, LI Jun-fen, FAN Wei-bin, WANG Jian-guo, QIN Zhang-feng. Synthesis of Silicalite-1 hollow sphere catalyst and its application for Beckmann rearrangement reaction[J]. Journal of Fuel Chemistry and Technology, 2016, 44(8): 1001-1009.

Citation:

JIN Ya-mei, DONG Mei, WANG Guo-fu, WANG Hao, LI Jun-fen, FAN Wei-bin, WANG Jian-guo, QIN Zhang-feng. Synthesis of Silicalite-1 hollow sphere catalyst and its application for Beckmann rearrangement reaction[J]. Journal of Fuel Chemistry and Technology, 2016, 44(8): 1001-1009.

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Synthesis of Silicalite-1 hollow sphere catalyst and its application for Beckmann rearrangement reaction

1.
State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China
2.
University of Chinese Academy of Sciences, Beijing 100049, China

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Corresponding author: mdong@sxicc.ac.cn; Tel: 0351-4046736, E-mail: fanwb@sxicc.ac.cn
Received Date: 2016-03-31
Rev Recd Date: 2016-05-10

Available Online: 2021-01-23

Publish Date: 2016-08-10

Abstract

Abstract

Silicalite-1 zeolite hollow sphere structured material was hydrothermally synthesized via the aid of carbon microspheres as hard-template. The morphology, structure, textural and physicochemical properties of the material were characterized with XRD, SEM, FT-IR, N₂ adsorption-desorption isotherm, ²⁹Si MAS NMR, TG, and XPS techniques. It was suggested that the obtained Silicalite-1 hollow spheres were highly crystallized with developed multiple channel structure and abundant surface hydroxyl groups, which endowed the material with excellent catalytic properties in Beckmann rearrangement reaction of cyclohexanone-oxime. Compared with the Silicalite-1 catalyst prepared from conventional method, the Silicalite-1 hollow sphere catalyst showed much higher activity to the conversion of cyclohexanone-oxime (99%) and selectivity of caprolactam (94%), with excellent stability at the same time. The abundant nest silanols and terminal silanols in Silicalite-1 hollow sphere were main active sites for Beckmann rearrangement reaction, and could be easily recovered from the deactivated catalysts by calcination.
- Silicalite-1,
- hollow sphere,
- carbon microspheres,
- hard-template,
- Beckmann rearrangement

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References(46)

References

[1]	LI Y, SHI J.Hollow-structured mesoporous materials:Chemical synthesis, functionalization and applications[J].Adv Mater, 2014, 26(20):3176-3205. doi: 10.1002/adma.v26.20
[2]	FUJI M, TAKAI C, RIVERA VIRTUDAZO R V.Development of new templating approach for hollow nanoparticles and their applications[J].Adv Powder Technol, 2014, 25(1):91-100. doi: 10.1016/j.apt.2013.12.002
[3]	OKAMOTO M.Synthesis of core-shell structured porous materials and applications as catalysts and precursors for hollow porous materials[J].Bull Jpn Petro Inst, 2013, 56(4):198-205. doi: 10.1627/jpi.56.198
[4]	金炜阳, 程党国, 陈丰秋, 詹晓力.分子筛膜包覆型催化剂的制备和应用[J].化学进展, 2011, 23(10):2021-2030. http://www.cnki.com.cn/Article/CJFDTOTAL-HXJZ201110005.htm JIN Wei-yang, CHENG Dang-guo, CHEN Feng-qiu, ZHAN Xiao-li.Synthesis and application of zeolite membrane encapsulated catalysts[J].Prog Chem, 2011, 23(10):2021-2030. http://www.cnki.com.cn/Article/CJFDTOTAL-HXJZ201110005.htm
[5]	WANG X D, TANG Y, WANG Y J, GAO Z, YANG W L, FU S K.Fabrication of hollow zeolite spheres[J].Chem Commun, 2000, 21:2161-2162. https://www.researchgate.net/profile/Wuli_Yang/publication/244539605_Fabrication_of_hollow_zeolite_spheres/links/0c96052ca2be9a1f38000000.pdf
[6]	LAI Z, BONILLA G, DIAZ I, NERY J G, SUJAOTI K, AMAT M A, KOKKOLI E, TERASAKI O, THOMPSON R W, TSAPATSIS M, VLACHOS D G.Microstructural optimization of a zeolite membrane for organic vapor separation[J].Science, 2003, 300(5618):456-460.
[7]	YU G, SUN B, PEI Y, XIE S, YAN S, QIAO M, FAN K, ZHANG X, ZONG B.Fe_xO_y@C spheres as an excellent catalyst for Fischer-Tropsch synthesis[J].J Am Chem Soc, 2010, 132(3):935-937. doi: 10.1021/ja906370b
[8]	KHAN E A, HU E, LAI Z.Preparation of metal oxide/zeolite core-shell nanostructures[J].Microporous Mesoporous Mater, 2009, 118(1/3):210-217.
[9]	WANG X D, ZHANG B Q, LIU X F, LIN J Y S.Synthesis of b-oriented TS-1 films on chitosan-modifiedα-Al₂O₃ substrates[J].Adv Mater, 2006, 18(24):3261-3265. doi: 10.1002/(ISSN)1521-4095
[10]	WANG X, YAN J, HUANG W.Synthesis of b-oriented TS-1 zeolite membranes with high performance in the oxyfunctionalization of n-hexane[J].Thin Solid Films, 2013, 534:40-44. doi: 10.1016/j.tsf.2013.01.075
[11]	PENG H, XU L, WU H, WANG Z, LIU Y, LI X, HE M, WU P.Synthesis and formation mechanism of TS-1@mesosilica core-shell materials templated by triblock copolymer surfactant[J].Microporous Mesoporous Mater, 2012, 153:8-17. doi: 10.1016/j.micromeso.2011.11.055
[12]	CHU N, WANG J, ZHANG Y, YANG J, LU J, YIN D.Nestlike hollow hierarchical MCM-22 microspheres:Synthesis and exceptional catalytic properties[J].Chem Mater, 2010, 22(9):2757-2763. doi: 10.1021/cm903645p
[13]	GARCÍA-MARTÍNEZ J, CAZORLA-AMORÓ S D, LINARES-SOLANO A, LIN Y S.Synthesis and characterisation of MFI-type zeolites supported on carbon materials[J].Microporous Mesoporous Mater, 2001, 42(2/3):255-268.
[14]	VALTCHEV V, MINTOVA S.Layer-by-layer preparation of zeolite coatings of nanosized crystals[J].Microporous Mesoporous Mater, 2001, 43(1):41-49. doi: 10.1016/S1387-1811(00)00345-0
[15]	CARUSO F, CARUSO R A, MOHWALD H.Nanoengineering of inorganic and hybrid hollow spheres by colloidal templating[J].Science, 1998, 282(5391):1111-1114. doi: 10.1126/science.282.5391.1111
[16]	VALTCHEV V.Silicalite-1 hollow spheres and bodies with a regular system of macrocavities[J].Chem Mater, 2002, 14(10):4371-4377. doi: 10.1021/cm020579v
[17]	VALTCHEV V.Core-shell polystyrene/zeolite a microbeads[J].Chem Mater, 2002, 14(3):956-958. doi: 10.1021/cm010927d
[18]	JI Y J, ZHANG B, XU L, WU H, PENG H, CHEN L, LIU Y, WU P.Core/shell-structured Al-MWW@B-MWW zeolites for shape-selective toluene disproportionation to para-xylene[J].J Catal, 2011, 283(2):168-177. doi: 10.1016/j.jcat.2011.08.007
[19]	LV Y, QIAN X, TU B, ZHAO D.Generalized synthesis of core-shell structured nano-zeolite@ordered mesoporous silica composites[J].Catal Today, 2013, 204:2-7. doi: 10.1016/j.cattod.2012.09.031
[20]	CHAMNANKID B, WITOON T, KONGKACHUICHAY P, CHAREONPANICH M.One-pot synthesis of core-shell silica-aluminosilicate composites:Effect of pH and chitosan addition[J].Colloids Surf A, 2011, 380(1/3):319-326.
[21]	DONG A, WANG Y, TANG Y, REN N, ZHANG Y, GAO Z.Hollow zeolite capsules:A novel approach for fabrication and guest encapsulation[J].Chem Mater, 2002, 14(8):3217-3219. doi: 10.1021/cm025577p
[22]	KIM J, PARK W, RYOO R.Surfactant-directed zeolite nanosheets:A high-performance catalyst for gas-phase beckmann rearrangement[J].ACS Catal, 2011, 1(4):337-341. doi: 10.1021/cs100160g
[23]	TAKAHASHI T, NISHI M, TAGAWA Y, KAI T.Catalyst deactivation of high-silica HZSM-5 in the Beckmann rearrangement reaction of cyclohexanone oxime[J].Microporous Mater, 1995, 3(s 4/5):467-471.
[24]	KUMAR R, CHOWDHURY B.Comprehensive study for vapor phase beckmann rearrangement reaction over zeolite systems[J].Ind Eng Chem Res, 2014, 53(43):16587-16599. doi: 10.1021/ie503170n
[25]	李倩, 严罗一, 夏定, 申永存.贝克曼重排反应研究进展[J].有机化学, 2011, 31(12):2034-2042. http://www.cnki.com.cn/Article/CJFDTOTAL-YJHU201112010.htm LI Qian, YAN Luo-yi, XIA Ding, SHEN Yong-cun.Research progress of Beckmann rearrangement[J].Chin J Org Chem, 2011, 31(12):2034-2042. http://www.cnki.com.cn/Article/CJFDTOTAL-YJHU201112010.htm
[26]	LI W C, LU A H, PALKOVITS R, SCHMIDT W, SPLIETHOFF B, SCHVTH F.Hierarchically structured monolithic silicalite-1 consisting of crystallized nanoparticles and its performance in the beckmann rearrangement of cyclohexanone oxime[J].J Am Chem Soc, 2005, 127(36):12595-12600. doi: 10.1021/ja052693v
[27]	HEITMANN G P, DAHLHOFF G, HOLDERICH W F.Catalytically active sites for the beckmann rearrangement of cyclohexanone oxime to epsilon-caprolactam[J].J Catal, 1999, 186(1):12-19. doi: 10.1006/jcat.1999.2552
[28]	YIN C, NI R, BAO X, CHEN Y.Synthesis of hierarchical porous silicalite-1 and its catalytic performance in Beckmann rearrangement[J].Microporous Mesoporous Mater, 2015, 202:133-137. doi: 10.1016/j.micromeso.2014.08.047
[29]	SONG H, XING C, LI B, SHEN W.Spherical carbon with SO3H groups as an efficient solid acid catalyst for 2, 4, 5-triphenyl-imidazole synthesis[J].Chem Select, 2016, 1(2):301-308.
[30]	BERENGUER-MURCIAÁ, GARCÍA-MARTÍNEZ J, CAZORLA-AMORÓ S D, LINARES-SOLANO Á, FUERTES A B.Silicalite-1 membranes supported on porous carbon discs[J].Microporous Mesoporous Mater, 2003, 59(2/3):147-159.
[31]	LI Q, HEDLUND J, STERTE J, CREASER D, BONS A J.Synthesis and characterization of zoned MFI films by seeded growth[J].Microporous Mesoporous Mater, 2002, 56(3):291-302. doi: 10.1016/S1387-1811(02)00503-6
[32]	KULKARNI S B S V P, KOTASTHANE A N BORADE R B, RATNASAMY P.Studies in the synthesis of ZSM-5 zeolites[J].Zeolites, 1982, 2(4):313-318. doi: 10.1016/S0144-2449(82)80077-8
[33]	SUGIMOTO M K H, TAKATSU K, KAWATA N.Correlation between the crystal size and catalytic properties of ZSM-5 zeolite[J].Zeolites, 1987, 7(6):503-507. doi: 10.1016/0144-2449(87)90087-X
[34]	OUTIRITE M, LAGRENÉE M, LEBRINI M, TRAISNEL M, JAMA C, VEZIN H, BENTISS F.Ac impedance, X-ray photoelectron spectroscopy and density functional theory studies of 3, 5-bis (n-pyridyl)-1, 2, 4-oxadiazoles as efficient corrosion inhibitors for carbon steel surface in hydrochloric acid solution[J].Electrochim Acta, 2010, 55(5):1670-1681. doi: 10.1016/j.electacta.2009.10.048
[35]	BOUMHARA K, TABYAOUI M, JAMA C, BENTISS F.Artemisia Mesatlantica essential oil as green inhibitor for carbon steel corrosion in 1M HCl solution:Electrochemical and XPS investigations[J].J Ind Eng Chem, 2015, 29:146-155. doi: 10.1016/j.jiec.2015.03.028
[36]	HUNGER M, KÄRGER J, PFEIFER H, CARO J, ZIBROWIUS B, BVLOW M, MOSTOWICZ R.Investigation of internal silanol groups as structural defects in ZSM-5-type zeolites[J].J Chem Soc Faraday Trans, 1987, 83(1):3459-3468.
[37]	KUHN J, MOTEGH M, GROSS J, KAPTEIJN F.Detemplation of[B]MFI zeolite crystals by ozonication[J].Microporous Mesoporous Mater, 2009, 120(1/2):35-38.
[38]	YAMAGISHI K, NAMBA S, YASHIMA T.Defect sites in highly siliceous HZSM-5 zeolites:A study performed by alumination and IR spectroscopy[J].J Phy Chem, 1991, 95(2):872-877. doi: 10.1021/j100155a071
[39]	BARBERA K, BONINO F, BORDIGA S, JANSSENS T V W, BEATO P.Structure-deactivation relationship for ZSM-5 catalysts governed by framework defects[J].J Catal, 2011, 280(2):196-205. doi: 10.1016/j.jcat.2011.03.016
[40]	VASCHETTO E G, CASUSCELLI S G, EIMER G A.Improvements in the Beckmann rearrangement process by using highly selective mesoporous catalysts[J].Microporous Mesoporous Mater, 2016, 221:175-181. doi: 10.1016/j.micromeso.2015.09.038
[41]	IZUMI Y, ICHIHASHI H, SHIMAZU Y, KITAMURA M, SATO H.Development and industrialization of the vapor-phase beckmann rearrangement process[J].Bull Chem Soc Jpn, 2007, 80(7):1280-1287. doi: 10.1246/bcsj.80.1280
[42]	ICHIHASHI H, SATO H.The development of new heterogeneous catalytic processes for the production of ε-caprolactam[J].Appl Catal A:Gen, 2001, 221(1/2):359-366.
[43]	SINGH P S, BANDYOPADHYAY R, HEGDE S G, RAO B S.Vapor phase Beckmann rearrangement of cyclohexanone oxime over SAPO-11 molecular sieve[J].Appl Catal A:Gen, 1996, 136:249-263. doi: 10.1016/0926-860X(95)00303-7
[44]	RÖSELER J, HEITMANN G, HÖLDERICH W F.Vapor-phase Beckmann using B-MFI zeolites[J].Appl Catal A:Gen, 1996, 144:319-333. doi: 10.1016/0926-860X(96)00127-5
[45]	KO A N, HUNG C C, CHEN C W, OUYANG K H.Mesoporous molecular sieve Al-MCM-41 as a novel catalyst for vapor-phase Beckmann rearrangement of cyclohexanone oxime[J].Catal Lett, 2001, 71(3/4):219-224. doi: 10.1023/A:1009038701442
[46]	KELEMEN S R, M.AFEWORKI A, GORBATY M L, COHEN A D.Characterization of organically bound oxygen forms in lignites, peats, and pyrolyzed peats by X-ray photoelectron spectroscopy (XPS) and solid-state 13C NMR methods[J].Energy Fuels, 2002, 16(6):1450-1462. doi: 10.1021/ef020050k