Catalytic Properties of Fast Pyrolysis Char Loaded with Cu-Zn on Alkali Lignin Pyrolysis for Monophenols†

doi:10.7503/cjcu20150681

Abstract

Abstract:

The fast pyrolysis char(FPC), which was a kind of mesoporous and macroporous carbon materials, was loaded with different molar ratios of Cu and Zn using the co-impregnation method to prepare the catalysts of Cu_xZn_y/FPC. The catalysts were characterized by X-ray diffraction(XRD), field-emission scanning electron microscope(FE-SEM) and energy dispersive X-ray spectroscopy(EDX). The catalytic properties on generating monophenols from alkali lignin pyrolysis were determined by thermogravimetric analyzer(TG) and pyrolysis-gas chromatography/mass spectrometry(Py-GC/MS). The results showed that the active components of CuO and ZnO were homogeneously embedded into the mesoporous and macroporous structure of FPC without the occurrence of aggregation or copper zinc alloy. With the metal loading increased, the diffraction peak intensity of CuO and ZnO was enhanced and average crystal sizes of CuO and ZnO became larger gradually. TG analysis showed that the catalysts significantly improved the reaction efficiency by reducing the activation energy while inhibited the formation of char residues. The monophenols obtained from the catalytic pyrolysis of alkali lignin were simplified from 23 kinds to 10 kinds. The catalyst of Cu_0.67Zn_0.33/FPC had the highest selectivity of monophenols up to 52.99%, and the selectivity increased by 49.7% compared with the catalyst of Cu/FPC.

Key words: Catalytic pyrolysis, Alkali lignin, Fast pyrolysis char, Monophenols, CuO, ZnO

CLC Number:

O643.3

TrendMD:

WANG Wenliang, GENG Jing, LI Lufei, CHANG Jianmin. Catalytic Properties of Fast Pyrolysis Char Loaded with Cu-Zn on Alkali Lignin Pyrolysis for Monophenols^†[J]. Chem. J. Chinese Universities, 2016, 37(4): 736.

Figures/Tables 11

Table 1 Basic analyses of alkali lignin and FPC

Sample	Ultimate analysis^a(mass fraction, %)					Proximate analysis^c(mass fraction, %)			BET surface area^d/ (m²·g^-1)
Sample	C	H		O^b	N	S	A	V	FC^b
Alkali lignin	62.40	6.14	29.43	0.26	1.77	6.21	66.43	27.36	$e$
FPC			$e$			9.04	19.39	71.57	307.56±12.33

Table 1 Basic analyses of alkali lignin and FPC

Sample	Ultimate analysis^a(mass fraction, %)					Proximate analysis^c(mass fraction, %)			BET surface area^d/ (m²·g^-1)
Sample	C	H		O^b	N	S	A	V	FC^b
Alkali lignin	62.40	6.14	29.43	0.26	1.77	6.21	66.43	27.36	$e$
FPC			$e$			9.04	19.39	71.57	307.56±12.33

Fig.1 XRD patterns of catalysts^a. Cu/FPC; b. Cu0.67Zn0.33/FPC; c. Cu0.50Zn0.50/FPC; d. Cu0.33Zn0.67/FPC; e. Zn/FPC.

Table 2 Average crystal sizes of CuO and ZnO in catalysts

Catalyst	D(CuO)/nm	D(ZnO)/nm	Catalyst	D(CuO)/nm	D(ZnO)/nm
Cu/FPC	27.9		Cu_0.33Zn_0.67/FPC	18.8	38.3
Cu_0.67Zn_0.33/FPC	26.0	32.1	Zn/FPC		43.0
Cu_0.50Zn_0.50/FPC	25.8	33.3

Fig.2 FE-SEM images of different catalysts^(A) Cu/FPC; (B) Cu0.67Zn0.33/FPC; (C) Cu0.50Zn0.50/FPC; (D) Cu0.33Zn0.67/FPC; (E) Zn/FPC.

Fig.3 EDX pattern of the representative Cu0.67Zn0.33/FPC catalyst

Fig.4 TG(A) and DTG(B) curves of alkali lignin pyrolysis with catalysts

Table 3 Kinetic parameters of catalytic pyrolysis of alkali lignin*

Sample	T_s/℃	T_max/℃	w(%)	E/(kJ·mol^-1)	A/min^-1	R²
Lignin	268—463	326	53.7	35.4	86.7	0.977
	670—779			161.3	8.5×10⁸	0.958
Cu	267—463	343	48.4	29.2	19.8	0.988
	669—765			134.4	2.7×10⁷	0.964
Cu_0.67Zn_0.33	267—463	349	49.4	29.9	21.5	0.985
	670—765			135.0	2.3×10⁷	0.952
Cu_0.50Zn_0.50	268—463	345	47.5	27.9	14.5	0.984
	669—764			111.7	8.8×10⁵	0.927
Cu_0.33Zn_0.67	268—462	350	48.4	29.5	19.7	0.985
	670—765			113.7	1.2×10⁶	0.940
Zn	268—462	344	47.3	29.4	19.2	0.983
	670—765			104.0	3.2×10⁵	0.943

Fig.5 Total ion chromatograms of pyrolysis vapors of alkali lignin with catalysts^(A) Zn/FPC; (B) Cu0.33Zn0.67/FPC; (C) Cu0.50Zn0.50/FPC; (D) Cu0.67Zn0.33/FPC; (E) Cu/FPC; (F) Lignin.

Table 4 Main components of pyrolysis vapors of alkali lignin with catalysts

No.	Compound		Relative content(area)(%)
No.	Compound		Lignin		Cu		Cu_0.67Zn_0.33		Cu_0.5Zn_0.5		Cu_0.33Zn_0.67		Zn
	Phenols		7.32		4.93		4.46		3.79		1.97		1.15
1	Phenol		1.53		4.30		3.89		3.16		1.97		1.15
2	o-Cresol		0.62		0.63		0.57		0.63
3	p-Cresol		0.69
4	3-Ethoxyphenol		1.88
5	4-Methylcatechol		1.77
6	4-Hydroxybenzaldehyde		0.58
7	5-tert-Butylpyrogallol		0.25
	Guaiacols		39.61		28.08		44.88		41.80		41.36		42.07
8	Guaiacol		13.74		17.82		25.26		21.98		24.77		25.84
9	Isocreosol		0.96		1.15		1.09		1.11		1.12		1.12
10	Creosol		2.83		3.06		3.32		3.21		3.03		3.25
11	3-Methoxycatechol		0.55
12	4-Ethylguaiacol		1.70		1.56		3.10		2.71		1.97		2.49
13	4-Acetyl-3-methylphenol		2.51
14	4-Vinylguaiacol				1.30		1.82		2.58		1.85		1.86
15	2-Methoxyquinol		0.45
16	Vanillin		9.29		2.74		8.67		8.66		8.62		7.51
17	(E)-Isoeugenol		1.29
18	Acetovanillone		2.77		0.45		1.62		1.55
19	Guaiacylacetone		1.04
20	Homovanillic acid		2.48
	Syringols		4.93		2.39		3.65		3.80		3.14		3.48
21	Syringol		4.10		2.39		3.65		3.80		3.14		3.48
22	Syringaldehyde		0.39
23	Syringone		0.44
	Alcohols		10.63		17.09		19.02		16.80		18.85		21.33
24	Methanol		8.75		17.09		18.53		16.54		18.85		21.33
25	Dimethylhexanol						0.49		0.26
26	1-Dodecanol		0.52
27	Pentadecanol		0.44
28	Nonadecanol		0.92
	Ethers		6.17		6.86		8.54		7.76		8.38		6.89
29	Methylvanillin		2.61		1.51		3.36		3.38		4.47		2.72
30	4-Vinylveratrole		0.45
31	Anisole				0.35
32	Veratrole		1.92		3.51		3.05		2.92		2.97		3.35
33	Homoveratrole		0.58		0.98		0.90		0.83		0.94		0.82
34	Triglycol monomethyl ether						1.23		0.63
35	1,2,3-Trimethoxybenzene		0.25		0.32
36	1,2,4-Trimethoxybenzene		0.36		0.19
No.	Compound	Relative content(area)(%)
No.	Compound	Lignin		Cu		Cu_0.67Zn_0.33		Cu_0.5Zn_0.5		Cu_0.33Zn_0.67		Zn
	Ketones	1.77		0.59		2.54		2.29		2.28		2.30
37	Acetone	0.80				1.78		1.31		1.43		1.52
38	Acetoveratrone	0.97
39	2,4-Dimethoxyacetophenone			0.59		0.76		0.98		0.85		0.78
	Esters	0.36		1.90		1.50		3.60		1.96		1.24
40	Allyl acetate			1.48
41	Butyrolactone	0.36
42	Aceteugenol			0.42		0.78		0.98				0.78
43	Diisobutyl phthalate					0.72		0.57		0.71		0.46
44	Dibutyl phthalate							0.39
45	Isopropyl Palmitate							0.57
46	Mono(2-ethylhexyl) phthalate							1.09		1.25
	Hydrocarbons	0.25		1.64		2.15		2.79		4.33		1.37
47	o-Cymene	0.25		0.42				0.28
48	2,4-Dimethyl styrene			0.29
49	1-Ethylidene-1H-indene			0.42				0.68
50	α-Cedrene			0.51		2.15		1.83		4.33		1.37
	Carboxylic acids	5.96		1.28		2.54		3.36		1.37
51	Acetic acid	0.40		1.28		0.72		0.87
52	Myristic acid	0.75						0.50
53	Pentadecylic acid	0.66
54	Petroselic acid	1.07
55	Palmitic acid	2.57
56	Tridecylic acid					1.82		1.99		1.37
57	Oleic Acid	0.51
	Sulfur compounds	23.00		35.24		10.72		14.01		16.36		20.17
58	Methanethiol	8.28
59	Dimethyl sulfide	12.76		24.31		6.79		8.68		10.13		11.68
60	2,3-Dithiabutane	1.96		9.57		3.25		5.33		6.23		8.49
61	2,4-Dithiapentane			1.36		0.68

Table 4 Main components of pyrolysis vapors of alkali lignin with catalysts

No.	Compound		Relative content(area)(%)
No.	Compound		Lignin		Cu		Cu_0.67Zn_0.33		Cu_0.5Zn_0.5		Cu_0.33Zn_0.67		Zn
	Phenols		7.32		4.93		4.46		3.79		1.97		1.15
1	Phenol		1.53		4.30		3.89		3.16		1.97		1.15
2	o-Cresol		0.62		0.63		0.57		0.63
3	p-Cresol		0.69
4	3-Ethoxyphenol		1.88
5	4-Methylcatechol		1.77
6	4-Hydroxybenzaldehyde		0.58
7	5-tert-Butylpyrogallol		0.25
	Guaiacols		39.61		28.08		44.88		41.80		41.36		42.07
8	Guaiacol		13.74		17.82		25.26		21.98		24.77		25.84
9	Isocreosol		0.96		1.15		1.09		1.11		1.12		1.12
10	Creosol		2.83		3.06		3.32		3.21		3.03		3.25
11	3-Methoxycatechol		0.55
12	4-Ethylguaiacol		1.70		1.56		3.10		2.71		1.97		2.49
13	4-Acetyl-3-methylphenol		2.51
14	4-Vinylguaiacol				1.30		1.82		2.58		1.85		1.86
15	2-Methoxyquinol		0.45
16	Vanillin		9.29		2.74		8.67		8.66		8.62		7.51
17	(E)-Isoeugenol		1.29
18	Acetovanillone		2.77		0.45		1.62		1.55
19	Guaiacylacetone		1.04
20	Homovanillic acid		2.48
	Syringols		4.93		2.39		3.65		3.80		3.14		3.48
21	Syringol		4.10		2.39		3.65		3.80		3.14		3.48
22	Syringaldehyde		0.39
23	Syringone		0.44
	Alcohols		10.63		17.09		19.02		16.80		18.85		21.33
24	Methanol		8.75		17.09		18.53		16.54		18.85		21.33
25	Dimethylhexanol						0.49		0.26
26	1-Dodecanol		0.52
27	Pentadecanol		0.44
28	Nonadecanol		0.92
	Ethers		6.17		6.86		8.54		7.76		8.38		6.89
29	Methylvanillin		2.61		1.51		3.36		3.38		4.47		2.72
30	4-Vinylveratrole		0.45
31	Anisole				0.35
32	Veratrole		1.92		3.51		3.05		2.92		2.97		3.35
33	Homoveratrole		0.58		0.98		0.90		0.83		0.94		0.82
34	Triglycol monomethyl ether						1.23		0.63
35	1,2,3-Trimethoxybenzene		0.25		0.32
36	1,2,4-Trimethoxybenzene		0.36		0.19
No.	Compound	Relative content(area)(%)
No.	Compound	Lignin		Cu		Cu_0.67Zn_0.33		Cu_0.5Zn_0.5		Cu_0.33Zn_0.67		Zn
	Ketones	1.77		0.59		2.54		2.29		2.28		2.30
37	Acetone	0.80				1.78		1.31		1.43		1.52
38	Acetoveratrone	0.97
39	2,4-Dimethoxyacetophenone			0.59		0.76		0.98		0.85		0.78
	Esters	0.36		1.90		1.50		3.60		1.96		1.24
40	Allyl acetate			1.48
41	Butyrolactone	0.36
42	Aceteugenol			0.42		0.78		0.98				0.78
43	Diisobutyl phthalate					0.72		0.57		0.71		0.46
44	Dibutyl phthalate							0.39
45	Isopropyl Palmitate							0.57
46	Mono(2-ethylhexyl) phthalate							1.09		1.25
	Hydrocarbons	0.25		1.64		2.15		2.79		4.33		1.37
47	o-Cymene	0.25		0.42				0.28
48	2,4-Dimethyl styrene			0.29
49	1-Ethylidene-1H-indene			0.42				0.68
50	α-Cedrene			0.51		2.15		1.83		4.33		1.37
	Carboxylic acids	5.96		1.28		2.54		3.36		1.37
51	Acetic acid	0.40		1.28		0.72		0.87
52	Myristic acid	0.75						0.50
53	Pentadecylic acid	0.66
54	Petroselic acid	1.07
55	Palmitic acid	2.57
56	Tridecylic acid					1.82		1.99		1.37
57	Oleic Acid	0.51
	Sulfur compounds	23.00		35.24		10.72		14.01		16.36		20.17
58	Methanethiol	8.28
59	Dimethyl sulfide	12.76		24.31		6.79		8.68		10.13		11.68
60	2,3-Dithiabutane	1.96		9.57		3.25		5.33		6.23		8.49
61	2,4-Dithiapentane			1.36		0.68

Fig.6 Component distribution of pyrolysis vapors of alkali lignin with catalysts^a. Lignin; b. Cu; c. Cu0.67Zn0.33; d. Cu0.50Zn0.50; e. Cu0.33Zn0.67; f. Zn.

Fig.7 Possible decomposition pathways of alkali lignin for monophenols with catalysts

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[6]	WANG Yongpeng,XU Zibo,LIU Mengzhu,ZHANG Haibo,JIANG Zhenhua. Non-enzymatic Glucose Sensor Based on the Electrospun Porous Foamy Copper Oxides Micro-nanofibers^† [J]. Chem. J. Chinese Universities, 2019, 40(6): 1310.
[7]	HUANG Rui,YAO Zhilong,SUN Peiyong,ZHANG Shenghong. Effect of Structure and Properties of CuO-WO₃-ZrO₂ on Hydrogenation Catalytic of Benzaldehyde^† [J]. Chem. J. Chinese Universities, 2019, 40(5): 1005.
[8]	Long TIAN,Yan LONG,Shuyan SONG,Cheng WANG. Synthesis of Flower-like Structured Mn/CuO-CeO₂ and the Catalytic Performance for CO Oxide Reaction ^† [J]. Chem. J. Chinese Universities, 2019, 40(12): 2549.
[9]	YANG Xiurong,ZHANG Chi,GAO Hongxu,ZHAO Fengqi,NIU Shiyao,GUO Zhaoqi,MA Haixia. Density Functional Theory Study of NO, NO₂ Adsorbed on ZnO(10 $1 ¯$ 0) Surface ^† [J]. Chem. J. Chinese Universities, 2019, 40(10): 2121.
[10]	WANG Fuxiang,CHEN Ziyu,YANG Weiting,LIU Lijuan,REN Guojian,LIU Yanfeng,PAN Qinhe. Preparation and Adsorption Performance for U(Ⅵ) of ZnO@ZIF-8 Core@Shell Microspheres^† [J]. Chem. J. Chinese Universities, 2019, 40(1): 24.
[11]	HUANG Yuting,YING Zuping,ZHENG Jixing,ZHUANG Sigeng,LIU Lu,FENG Wei. Hierarchical Porous ZnO Nanomaterial Synthesized with Corn Straw as Biological Templates and Its Photocatalytic Performance^† [J]. Chem. J. Chinese Universities, 2018, 39(9): 2031.
[12]	HAN Zhiying, LI Youji, LIN Xiao, WANG Ziyu, LI Ziqin, WANG Hao. Preparation and Photoelectrocatalytic Performance of Fe₂O₃/ZnO Composite Electrode Loading on Conductive Glass^† [J]. Chem. J. Chinese Universities, 2018, 39(4): 771.
[13]	ZHOU Lie, WU Qingyun, XU Ying, WANG Chenguang, MA Longlong, LI Wenzhi, CHEN Peili. Depolymerization of the Alkali Lignin for Aromatic Compounds over Ni/SiO₂-Al₂O₃ Solid Acid Catalysts^† [J]. Chem. J. Chinese Universities, 2018, 39(4): 735.
[14]	XUE Jiao, WANG Runwei, ZHANG Zongtao, QIU Shilun. Preparation and Photocatalytic Performance of Novel Zn-doped C/Nb₂O₅ Nanoparticles Catalyst^† [J]. Chem. J. Chinese Universities, 2018, 39(2): 319.
[15]	ZHANG Jin, SHI Tiancai, LUO Liwen, LIU Jia, LIU Rong, LIU Le, LIANG Ming, MA Yangmin. One-pot Synthesis of β-Carboline Derivatives Catalyzed by CuO Nanoparticles^† [J]. Chem. J. Chinese Universities, 2018, 39(11): 2411.