Hydrolysis of woody biomass by biomass-derived reusable heterogeneous catalyst
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1 Electronic Supplementry Mteril (ESI) for Chemicl Science. This journl is The Royl Society of Chemistry 2015 Hydrolysis of woody biomss by biomss-derived reusble heterogeneous ctlyst Hirokzu Kobyshi, b Hiroyuki Kiki, b Abhijit Shrotri, Kot Techikwr b nd Atsushi Fukuok* b Institute for Ctlysis, Hokkido University, Kit 21 Nishi 10, Kit-ku, Spporo, Hokkido , Jpn. b Grdute School of Chemicl Sciences nd Engineering, Hokkido University, Kit 13 Nishi 8, Kit-ku, Spporo, Hokkido , Jpn. Tble of contents Experimentl detils S2 Preprtion of typicl conventionl crbon ctlyst S3 Comprison of E-Crbon with soluble cids S3 Tble S1 Weight percent of elements in Euclyptus sh in EDX nlysis S4 Tble S2 Effect of preprtion temperture of E-Crbon on the formtion mount of ctlyst (recovery), nd ctlytic ctivity of the prepred ctlysts in the hydrolysis of bll-milled cellulose S4 Tble S3 Detiled results of hydrolysis of Euclyptus t 488 K shown in Tble 1 S4 Tble S4 Hydrolysis of Euclyptus t lower temperture of 473 K S5 Fig. S1 Photogrphs of Euclyptus nd E-Crbon S5 Fig. S2 FT-IR spectr of crbons nd Euclyptus S5 Fig. S3 XP spectr of E-Crbon nd N 2 -treted Euclyptus S6 Fig. S4 Wter dsorption isotherm for E-Crbon t 298 K S6 Fig. S5 N 2 dsorption isotherms for E-Crbon nd recycled E-Crbon S6 Fig. S6 Rmn spectrum of E-Crbon S7 Fig. S7 XRD ptterns of E-Crbon nd recycled E-Crbon S7 References S7 S1
2 Experimentl detils Euclyptus. Euclyptus powder (20 g, m) ws boiled in 500 ml wter for 0.5 h in n eggplnt flsk (2 L) to remove soluble ingredients. The resulting powder ws filtered through filter pper (type 5A, 7 m), trnsferred to n eggplnt flsk (100 ml), dried by rotry evportor (12 kp) t 333 K, nd further dried using rotry pump (1 P) t 333 K with trp (77 K). Composition of the wshed Euclyptus ws determined by NREL/TP , S1 NREL/TP S2 nd EDX (Shimdzu, EDX-720) on dry bsis. We determined the mount of xyln in hemicellulose, nd other types of sugrs were omitted. In this nlysis, detected glucose ws fully scribed to cellulose, since hrdwood hemicellulose contins lmost no glucose. S3 Air oxidtion of Euclyptus, rection residue, nd cellulose. Dried Euclyptus or cellulose powder of 4.00 g ws spred with thickness of 3 mm on Pyrex dish (ø130) to uniformly prepre ctlyst nd void hot spots. The smple ws clcined under ir t tmospheric pressure in n electric furnce (Denken-Highdentl, KDF S90) with the following progrm: 298 to 573 K by 5 K min -1 nd 573 K for 1 h. In the cse of rection residue, the residue of 1.63 g (recovered in lrge-scle experiment, see below) ws clcined under the sme conditions. Temperture inside the smple ws monitored by thermocouple (Chino; ø0.5) equipped with qurtz tube (c. ø1). Chrcteristion. Prepred ctlysts were nlysed by IR (JASCO, FT/IR 660Plus; deuterted L-lnine triglycine sulphte detector, trnsmission mode, KBr disk), 13 C CP/MAS NMR (Bruker, MSL-300; 75 MHz, MAS 8 khz), XPS (JEOL, JPC-9010MC), N 2 dsorption (BEL Jpn, Belsorp Mini; 77 K), wter dsorption (BEL Jpn, Belsorp Mx; 298 K), Rmn spectroscopy (Renishw, invi Reflex, 532 nm), nd X-ry diffrction (Rigku, Ultim IV). Acidity of 0.1 M NCl solution (I = 0.1) of E-Crbon (50 mg / 40 ml) ws mesured by glss electrode, which indicted ph 3.6. Therefore, the cidifiction of queous phse ws limited even t the high ionic strength. Pretretment (mix-milling). Euclyptus (5.0 g) nd ctlyst (0.77 g) were milled together in n Al 2 O 3 pot (250 ml) with Al 2 O 3 blls (99.9%, ø15, 210 g) by Fritsch P-6 plnetry bll mill. Milling conditions were 500 rpm for 2 h with 10 min intervl fter every 10 min of milling. Hydrolysis rection. The hydrolysis of Euclyptus ws performed in hstelloy C-22 high-pressure rector (OM Lb-Tech, MMJ-100) equipped with n gittor operting t 600 rpm nd thermocouple. Mix-milled smple (374 mg) nd 40 ml of 120 ppm HCl q. were dded into the rector. The temperture of the rection S2
3 mixture ws elevted from 298 K to 488 K in c. 17 min nd then quickly lowered to 298 K. After finishing the rection, the rection solution ws seprted by centrifugtion nd decnttion. The liquid phse ws ple yellow due to dissolution of smll frction of lignin nd ctlysts; however, this colouring ws common in the hydrolysis of lignocellulose. In ddition, we hve confirmed tht the dissolved prt of the ctlyst ws inctive towrds hydrolysis of lignocellulose. The remining solid ws wshed twice with 40 ml of wter, trnsferred to n eggplnt flsk (100 ml), dried by rotry evportor (12 kp) t 333 K, nd further dried using rotry pump (1 P) t 333 K with trp (77 K). For the trnsformtion of solid residue to fresh ctlyst, we performed lrge-scle experiment using 4.00 g of the mix-milled smple to ccumulte the residue. A portion of the produced ctlyst ws used for the second-cycle rection. Products were nlysed by high-performnce liquid chromtogrphy (Shimdzu; refrctive index nd ultrviolet detectors) with SUGAR SH1011 (Shodex; ø8 300 mm; eluent: wter 0.5 ml min 1 ; 323 K) nd Rezex RPM-Monoscchride Pb++ (Phenomenex; ø mm; eluent: wter 0.6 ml min 1 ; 343 K) columns. Preprtion of typicl conventionl crbon ctlyst Production of 1 kg of n lkli-ctivted crbon (K26) requires 3.75 kg of KOH, since the weight rtio of KOH to crbon is 3 nd the yield of ctivted crbon is 80%. S4 After the lkli-ctivtion, KOH is neutrlised with 3.28 kg of H 2 SO 4, giving 5.83 kg of K 2 SO 4. As the solubility of K 2 SO 4 in wter t 293 K is g g-wter 1, wshing out it needs t lest 52.5 kg of wter. More wter nd HCl re necessry to completely remove slts from lkli-ctivted crbon. S4 Comprison of E-Crbon with soluble cids Sulphuric cid nd orgnic cids hve low ctivity t the ph (>3) given by wekly cidic crbons. S4,S5 It is known tht the high-yielding production of glucose from lignocellulose requires more thn 50 mm sulphuric cid, S6 which is significntly lrger thn the concentrtion of ctlyst in our study (the concentrtion of crboxylic cid on E-Crbon corresponds to only 2.6 mm in the solution). Therefore, E-crbon is more ctive thn sulphuric cid t such low cid concentrtion. S3
4 Tbles Tble S1 Weight percent of elements in Euclyptus sh in EDX nlysis CO SiO 2 MgO Al 2 O 3 SO 3 P 2 O 5 Fe 2 O 3 K 2 O 54% 13% 9.3% 8.6% 7.3% 3.2% 1.8% 0.7% Contents of elements were determined s oxides (wt%). Tble S2 Effect of preprtion temperture of E-Crbon on the formtion mount of ctlyst (recovery), nd ctlytic ctivity of the prepred ctlysts in the hydrolysis of bll-milled cellulose Entry Preprtion temp. /K Recovery /wt% Product yield in the hydrolysis rection /% Glucose Fructose Mnnose Oligomers LG b 5-HMF c Furfurl S d S e S n.d. f S n.d. f Bll-milled cellulose 324 mg, ctlyst 50 mg, wter 40 ml, 503 K. b Levoglucosn. c 5-Hydroxymethylfurfurl. d The prepred mteril ws not used for the hydrolysis of cellulose s the smple ws lmost lignocellulosic mteril. e Recovery bsed on crbon content ws 49%. f Not determined due to overlp of peks. Tble S3 Detiled results of hydrolysis of Euclyptus t 488 K shown in Tble 1 Entry Solvent Ctlyst Product yield /% (wt% bsed on whole Euclyptus) Glucose Xylose Sugr isomers Oligomers LG b 5-HMF c Furfurl 1 Wter No ctlyst 3 d (2) 30 e (3) (1) (7) (<1) (<1) (<1) 2 Wter E-Crbon 31 d (17) 83 e (9) (3) (21) (<1) (<1) (1) % HCl No ctlyst 32 d (17) 26 e (3) (5) (1) (<1) (3) (3) % HCl E-Crbon (1st cycle) % HCl E-Crbon (2nd cycle) % HCl N 2 -treted Euclyptus 78 d (40) 94 e (10) (2) (1) (2) (2) (2) 82 d (42) 86 e (10) (3) (<1) (2) (3) (3) 28 d (14) 26 e (3) (4) (4) (<1) (2) (2) % HCl Air-oxidised cellulose 77 d (40) 91 e (10) (5) (2) (2) (1) (<1) Accurcy is not very high due to overlp of peks. b Levoglucosn. c 5-Hydroxymethylfurfurl. d Bsed on crbon of cellulose. e Bsed on crbon of xyln. S4
5 Tble S4 Hydrolysis of Euclyptus t lower temperture of 473 K Entry Solvent Ctlyst Product yield /% (wt% bsed on whole Euclyptus) S % HCl E-Crbon (1st cycle) Glucose Xylose Sugr isomers Oligomers LG b 5-HMF c Furfurl 35 d (18) 91 e (10) (4) (6) (<1) (<1) (<1) S % HCl E-Crbon (2nd cycle) 54 d (28) >95 e (11) (3) (8) (1) (<1) (<1) Accurcy is not very high due to overlp of peks. b Levoglucosn. c 5-Hydroxymethylfurfurl. d Bsed on crbon of cellulose. e Bsed on crbon of xyln. Figures Fig. S1 Photogrphs of Euclyptus (left) nd E-Crbon (right). Fig. S2 FT-IR spectr of E-Crbon (red solid line), N 2 -treted Euclyptus (green dotted line), Euclyptus (blue dshed line) nd ir-oxidised cellulose (violet solid line). Trnsmission mode, KBr pellet. Absorbnce vlues hve been normlised by concentrtion of smple for the quntittive comprison, but Abs. of rw dt before the normlistion is similr (t most 20% difference). S5
6 Fig. S3 XP spectr of () E-Crbon nd (b) N 2 -treted Euclyptus. Pek positions of the curve fittings (blck lines) were fixed t ev for C C nd C=C, t ev for C C, t for C=O nd t ev for CO 2 R. S7 Fig. S4 Wter dsorption isotherm for E-Crbon t 298 K. Fig. S5 N 2 dsorption isotherms for E-Crbon nd recycled E-Crbon. The dsorption mounts were very low, nd therefore the BET surfces res were not clculted ccurtely (< 2 m 2 g 1 ). S6
7 Fig. S6 Rmn spectrum of E-Crbon. Fig. S7 XRD ptterns of E-Crbon nd recycled E-Crbon. The brod pek t 23 is chrcteristic of morphous crbon. Shrp peks for the recycled ctlyst re ssigned to -Al 2 O 3 (derived from mix-milling instruments). References S1 A. Sluiter, B. Hmes, R. Ruiz, C. Scrlt, J. Sluiter, D. Templeton nd D. Crocker, NREL/TP , S2 A. Sluiter, B. Hmes, R. Ruiz, C. Scrlt, J. Sluiter nd D. Templeton, NREL/TP , S3 P. Mäki-Arvel, T. Slmi, B. Holmbom, S. Willför nd D. Y. Murzin, Chem. Rev., 2011, 111, S4 H. Kobyshi, M. Ybushit, T. Komnoy, K. Hr, I. Fujit nd A. Fukuok, ACS Ctl., 2013, 3, S5 H. Kobyshi, M. Ybushit, J. Hsegw nd A. Fukuok, J. Phys. Chem. C, 2015, 119, S6 J. S. Luterbcher, D. M. Alonso nd J. A. Dumesic, Green Chem., 2014, 16, S7 H. P. Boehm, Crbon, 2002, 40, S7
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