ZSM-5 zeolite single crystals with b-axis-aligned mesoporous channels as an efficient catalyst for conversion of bulky organic molecules
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1 Supporting informtion ZSM-5 zeolite single rystls with -xis-ligne mesoporous hnnels s n effiient tlyst for onversion of ulky orgni moleules Fujin Liu,,e Tom Willhmmr, Ling Wng, Longfeng Zhu, Qi Sun, Xingju Meng, Wiler Crrillo- Crer, Xioong Zou,*, n Feng-Shou Xio*, Key L of Applie Chemistry of Zhejing Provine, Zhejing University, Hngzhou , Chin Berzelii Centre, EXSELLENT on Porous Mterils n Deprtment of Mterils n Environmentl Chemistry, Stokholm University, Stokholm SE , Sween College of Chemistry, Jilin University, Chnghun , Chin Mx-Plnk-Institut für Chemishe Physik fester Stoffe, Dresen, DE-01187, Germny e Institute of Applie Chemistry, Shoxing University, Shoxing , Chin S1
2 Synthesis of Smples All regents were of nlytil gre n use s purhse without further purifition. Copolymer polystyrene-o-4-polyvinylpyriine (moleulr weight out , PSt-o-P4VP), methyl ioie, n tetrpropyl mmonium hyroxie (TPAOH, 19.5 wt %), were purhse from Sigm-Alrih Compny, Lt. (USA). DMF, petroleum ether, tetrethyl orthosilite (TEOS), NAlO 2, NOH, enzlehye, penterythritol, 2-hyroxyetophenone, 1-pentnol, n oene were purhse from Tinjin Gungfu Chemil Co (Chin). Ctioni polyillylimethylmmonium hlorie (PDADMAC, 10 wt %, moleulr weight out ) ws purhse from Yinhu Chemil Co. (Chin). Quternry mmonition of PSt-o-P4VP opolymer (C-PSt-o-P4VP) ws trete y CH 3 I t room temperture in DMF solvent uner rk onition. As typil run, 2.0 g of PSt-o-P4VP ws issolve into 40 ml of DMF, followe y ition of 1.2 ml of methy-ioie. After stirring for 20 h t room temperture, 300 ml of petroleum ether ws e, giving soli of quternry mmonite PSt-o- P4VP, followe y filtering, wshing with petroleum ether, n rying t 100 C. ZSM-5 with -xis-ligne mesopores (ZSM-5-OM) ws synthesize in the presene of oth TAPOH n C-PSt-o-P4VP templtes. As typil run, 0.08 g of NAlO 2, 13 ml of TPAOH, n 7.0 ml of TEOS were mixe, followe y ition of 20 ml of wter. After stirring t room temperture for 6 h n ging t 100 C for 2 h, ler zeolite preursor ws otine. In the menwhile, 2 g of C-PSt-o-P4VP ws issolve into 5 ml of wter, followe y ition of 3 ml of TPAOH, giving C-PSt-o-P4VP solution. After mixing the ler zeolite preursor with the C-PSt-o-P4VP solution, the mixture ws stirre for 24 h t room temperture, then trnsferre into n utolve for rystlliztion t 180 C for 3-4 ys. The prouts were ollete y filtrtion, rie in ir n line t 550 C to remove the templte. For omprison, onventionl ZSM-5 ws synthesize uner the sme onition ut without using the C-PSt-o-P4VP templte. Disorere mesoporous ZSM-5 ws synthesize using the tioni opolymer PDADMAC. 9 Chrteriztion XRD ptterns were otine on Rigku D/MAX 2550 iffrtometer with Cu Kα rition. Nitrogen sorption n esorption isotherms were mesure t -196 C using Miromeritis ASAP 2010M system. The smples were egsse for 10 h t 150 C efore the mesurements. The pore-size istriution for mesopores ws lulte using Brrett-Joyner-Hlen (BJH) moel. SEM ws performe on Hithi S-5200 eletron mirosope. TEM ws performe on JEOL JEM 2100F eletron mirosope t 200 kv. Thin ross setions of the ZSM-5-OM for TEM stuies were prepre using fouse ion-em (FIB) on n FEI Qunt 200 3D ul em evie (FEI ompny, Einhoven, NL) equippe with n Omniproe miro-mnipultor. Thermogrvimetri nlysis (TG) n ifferentil S2
3 therml nlysis (DTA) were performe with Perkin-Elmer TGA7 n DTA-1700 pprtus, respetively. 1 H n 13 C NMR were reore on Bruker Avne 500 spetrometer using 5 mm QNP proe equippe with z-grient oil. FT-IR spetr were reore y using Bruker 66V FT-IR spetrometer. Ctlyti tests All smples use in tlyti tests were H-form. As typil run, the smple ws ion-exhnge with 1M NH 4 NO 3 t 80 C, followe y lintion t 500 C for 3 h. This proeure ws repete twie. Ctlyti retions inlue protetion of enzlehye with penterythritol (PBP), onenstion of enzlehye with hyroxyetophenone (CBH), n onenstion of enzlehye with 1-pentnol (CBP). In these retions, the prouts were nlyze y gs hromtogrphy Shimzu 14C with flme ioniztion etetor (FID), n oene ws use s n internl stnr. The olumn ws OV-1 (30 m); the initil temperture ws 100 C, the heting rte ws 10 C/min, n the finl temperture ws 220 C, the temperture of FID etetor ws 280 C. In these retions, the stirring rte ws higher thn 800 rpm, n tlyst grnules were less thn 400 mesh. Protetion of enzlehye with penterythritol (PBP) ws performe y mixing 0.04 g of the tlyst with 20 mmol of enzlehye, 10 mmol of penterythritol, n 8 mmol of toluene solvent in threeneke roun flsk equippe with onenser n mgneti stirrer. After retion t 120 C for 4.5 h, the prouts were nlyze y GC. The prout ws ietl with the seletivity of nerly 100 %. 3 This prout ws seprte n onfirme y 1 H NMR tehnique. Conenstion of enzlehye with 2-hyroxyetophenone (CBH) ws performe y mixing 0.10 g of tlyst with 14 mmol of enzlehye n 7 mmol of 2-hyroxyetophenone in three-neke roun flsk equippe with onenser n mgneti stirrer. After retion t 150 C for 18 h, the prouts were nlyze y GC. In this retion, the prouts were flvnone n hlone with seletivities of nerly 100%. 3 The prouts were seprte n onfirme y 1 H NMR tehnique. Conenstion of enzlehye with 1-pentnol (CBP) ws performe y mixing 0.20 g of tlyst with 25 mmol of enzlehye n 17.2 g (200 mmol) of 1-pentnol in three-neke roun flsk equippe with onenser n mgneti stirrer. After retion t 80 C for 16 h, the prout ws nlyze y GC. 18 The prout ws 1-phenylhexn-1-ol with the seletivity of nerly 100%. This prout ws seprte n onfirme y 1 H NMR tehnique. S3
4 Contents Fig. S1 1 H NMR spetrum of C-PSt-o-P4VP. Fig. S2 13 C NMR spetrum of C-PSt-o-P4VP. Fig. S3 FT-IR spetr of () PSt-o-P4VP n () C-PSt-o-P4VP. Fig. S4 () 13 C NMR spetrum of queous C-PSt-o-P4VP n 13 C MAS NMR spetr of the soli smples hyrothermlly synthesize t () 12 h n () 24 h using C-PSt-o-P4VP s templte for generting mesoporosity in the synthesis of ZSM-5-OM. Fig. S5 XRD ptterns of the soli smples hyrothermlly synthesize t () 12 h n () 24 h using C- PSt-o-P4VP s templte for generting mesoporosity in the synthesis of ZSM-5-OM. Fig. S6 () XRD pttern n () N 2 sorption isotherm of ZSM-5-OM synthesize in the presene of C- PSt-o-P4VP templte. Insert: BJH pore size istriution. Fig. S7 SEM imges of ZSM-5-OM. Fig. S8 Preprtion of thin ross setions for TEM y fouse Ion Bem (FIB). Fig. S9 HRTEM imges tken from rystls ut with FIB viewe long () [010], () [100], n () [001] iretions. Fig. S10 (A) TG n (B) DTA urves of () onventionl ZSM-5 n () ZSM-5-OM smples. Fig. S11 A sheme showing the morphology, surfes n iretions of the miroporous hnnels in ZSM-5-OM rystls. Fig. S12 XRD ptterns of (A) onventionl ZSM-5 n (B) ZSM-5-OM () efore n () fter 100% stem tretment t 800 C for 5 h. Fig. S13 N 2 isotherm of ZSM-5-OM trete in 100% steming t 800 C for 5 h. Insert: BJH pore size istriution. S4
5 * m n o * ' ' N ' N CH 3 I ' ' ' Chemil shift (ppm) Fig. S1 1 H NMR spetrum of C-PSt-o-P4VP. The pperne of the strong ns t 8.6 n 2.7 ppm inites suessful quternry mmonition of PSt-o-P4VP opolymer. S5
6 * m n o * ' ' N ' N CH 3 I ' ' Chemil shift (ppm) Fig. S2 13 C NMR spetrum of C-PSt-o-P4VP. The pperne of the strong ns t 48.2 n ppm inites suessful quternry mmonition of PSt-o-P4VP opolymer. S6
7 Trnsmittne (% ) m m Wvenumer (m -1 ) Fig. S3 FT-IR spetr of () PSt-o-P4VP n () C-PSt-o-P4VP. The pperne of the strong n t 1639 n sene of the strong n t 1415 m -1 inite suessful quternry mmonition of PSt-o- P4VP opolymer. S7
8 * e f * m n o e ' ' C-PSt-o-P4VP e f e N ' N I CH 3 ' Signl of TPA +, ', e f ' Chemil shift (ppm) Fig. S4 () 13 C NMR spetrum of queous C-PSt-o-P4VP n 13 C MAS NMR spetr of the soli smples hyrothermlly synthesize t () 12 h n () 24 h using C-PSt-o-P4VP s templte for generting mesoporosity in the synthesis of ZSM-5-OM. Compre with those of queous C-PSt-o- P4VP solution, the peks ssoite with C-PSt-o-P4VP speies in the soli smples re reltively wek ue to the low onentrtion of C-PSt-o-P4VP speies n MAS mesurements. Clerly, the soli smples hyrothermlly synthesize for h still exhiit peks ttriute to C-PSt-o-P4VP, suggesting tht the C-PSt-o-P4VP speies re essentilly intt uring the rystlliztion of ZSM-5-OM. S8
9 Intensity (.u.) Thet (egree) Fig. S5 XRD ptterns of the soli smples hyrothermlly synthesize t () 12 h n () 24 h using C- PSt-o-P4VP s templte for generting mesoporosity in the synthesis of ZSM-5-OM. S9
10 Volume sorption (m 3 /g) Thet (egree) Pore size (nm) V/logD (m 3 /g) Reltive pressure (p/p 0 ) Fig. S6 () XRD pttern n () N 2 sorption isotherm of ZSM-5-OM synthesize in the presene of C- PSt-o-P4VP templte. Insert: BJH pore size istriution. S10
11 Fig. S7 SEM imges of ZSM-5-OM. The smple hs uniform rystls with rough surfes. S11
12 Preprtion of TEM lmellr smples (trenh) with the FIB metho The prtiles of ZSM-5-OM were isperse on flt surfe (glss) with ethnol. While still eing emee in little ethnol, they were tthe t the top of thin opper hlf-ring y iret ontt n gliing the hlf-ring on the glss surfe. After rying, few prtiles oriente long the min rystllogrphi xes (,, ) were hosen, whih were then overe with thin Pt lyers (ion potentil 30 kv, urrent 0.1 na) for protetion efore FIB milling (or utting) using ul-em evie (FIB- SIM/SEM Qunt 200 3D; FEI ompny). The finl TEM trnsprent trenh uts were prepre y ion milling (V = 30 kv) using n ion urrent from 1.00 to 0.03 na, erese with eresing thiknesses. Copper hlf-ring (on FIB holer) with tthe prtiles on the thin top surfe Fig. S8 Preprtion of thin ross setions for TEM y Fouse Ion Bem (FIB). () Top view of ZSM- 5-OM rystl efore FIB utting with the esire slie mrke in green. The intene viewing iretion in the TEM is mrke y n rrow. () The slie fter the FIB ut. This rystl is ut perpeniulr to the - xis. () The morphology of ZSM-5-OM rystl efore utting with the three perpeniulr iretions for the uts mrke y re, green n lue, respetively. The finl thin slies for TEM re pproximtely 70 nm thik. S12
13 Fig. S9 HRTEM imges tken from rystls ut with FIB viewe long () [010], () [100], n () [001] iretions. The mesopores re mrke with re line. S13
14 100 A TG /% Temperture ( C) DTA /(uv/mg) B Temperture ( C) Fig. S10 (A) TG n (B) DTA urves of () onventionl ZSM-5 n () ZSM-5-OM smples. S14
15 ( 010 ) Fig. S11 A sheme showing the morphology, surfes n the iretion of miropores hnnels in ZSM-5 rystls. S15
16 A Intensity (.u.) Thet (egree) B Intensity (.u.) Thet (egree) Fig. S12 XRD ptterns of (A) onventionl ZSM-5 n (B) ZSM-5-OM () efore n () fter 100% stem tretment t 800 C for 5 h. S16
17 Volume sorption (m 3 /g) Pore imeter (nm) V/logD (m 3 /g) Reltive pressure (p/p 0 ) Fig. S13 N 2 isotherm of ZSM-5-OM trete in 100% steming t 800 C for 5 h. Insert: BJH pore size istriution. S17
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