γ-戊内酯/水复合溶剂体系中金属硫酸盐催化半纤维素定向转化制备糠醛

doi:10.3969/j.issn.0253-2417.2020.01.003

Abstract

Abstract:

Furfural was prepared from hemicelluloses and lignocellulosic biomass in the presence of the γ-valerolactone/water solvent system with low cost sulfate as catalyst. The yield of furfural could be obtained as high as 50.2%, accompanying with 95.5% of hemicellulose conversion. Furthermore, furfural also could be prepared from real lignocellulosic biomass corncob and bamboo meal in the above catalytic system with the yield of 39.5% and 29.7%, respectively. In this case, corncob and bamboo meal conversion could be 86.5% and 80.50%.

Key words: larch sawdust, SiO₂@C composites, in situ doping, structural control, dye adsorption, lignocellulosic biomass, hemicellulose, γ-valerolactone, sulfate, furfural

CLC Number:

TQ35
TQ35

Chao LIU,Linshan WEI,Xiaoyan YIN,Min WEI,Jianchun JIANG,Kui WANG. Directional Conversion of Hemicellulose into Furfural via Sulfate Catalysts in the Gamma-valerolactone/Water Compound Solvent[J]. Chemistry and Industry of Forest Products, 2020, 40(1): 17-24.

Figures/Tables 8

Fig.1

Table 1

Table 2

Fig.2

Fig.3

Fig.4

Fig.5

Fig.6

References 29

1	卢怡, 郑志锋, 黄元波, 等. 半纤维素选择性催化制备糠醛及其衍生物的研究进展[J]. 林产化学与工业, 2018, 38 (3): 5- 20.
	LU Y , ZHENG Z F , HUANG Y B , et al. Research advances in preparation of furfural and its derivatives by selective catalytic conversion of hemicellulose[J]. Chemistry and Industry of Forest Products, 2018, 38 (3): 5- 20.
2	刘菲, 郑明远, 王爱琴, 等. 酸催化制备糠醛研究进展[J]. 化工进展, 2017, 36 (1): 156- 165.
	LIU F , ZHENG M Y , WANG A Q , et al. Research progresses in furfural production by acid catalysts[J]. Chemical Industry and Engineering Progress, 2017, 36 (1): 156- 165.
3	周圆圆, 李芹, 李瑞阳, 等. 温控可变相态离子液体催化转化玉米芯制备糠醛[J]. 安徽科技学院学报, 2017, 31 (6): 86- 90.
	ZHOU Y Y , LI Q , LI R Y , et al. Catalytic conversion of corncob for the furfural with temperature-sensitive phase-variable ionic liquid[J]. Journal of Anhui Science and Technology University, 2017, 31 (6): 86- 90.
4	谈金, 王晨光, 陈伦刚, 等. 纤维素类碳水化合物转化为糠醛的研究进展[J]. 新能源进展, 2018, 6 (1): 1- 7. doi: 10.3969/j.issn.2095-560X.2018.01.001
	TAN J , WANG C G , CHEN L G , et al. Progress on conversion of cellulosic carbohydrates into furfural[J]. Advances in New and Renewable Energy, 2018, 6 (1): 1- 7. doi: 10.3969/j.issn.2095-560X.2018.01.001
5	MARISCAL R , MAIRELES-TORRES P , OJEDA M , et al. Furfural:A renewable and versatile platform molecule for the synthesis of chemicals and fuels[J]. Energy Environmental Science, 2016, 9 (4): 1144- 1189. doi: 10.1039/C5EE02666K
6	XU W , ZHANG S , LU J , et al. Furfural production from corncobs using thiourea as additive[J]. Environmental Progress Sustainable Energy, 2017, 36, 690- 695. doi: 10.1002/ep.12489
7	YANG W , LI P , BO D , et al. Optimization of furfural production from D-xylose with formic acid as catalyst in a reactive extraction system[J]. Bioresource Technology, 2013, 133, 361- 369. doi: 10.1016/j.biortech.2013.01.127
8	XIOURAS C , RADACSI N , STURM G , et al. Furfuralsynthesis from D-xylose in the presence of sodium chloride:Microwave versus conventional heating[J]. ChemSusChem, 2016, 9 (16): 2159- 2166. doi: 10.1002/cssc.201600446
9	LI H , REN J , ZHONG L , et al. Production of furfural from xylose, water-insoluble hemicelluloses and water-soluble fraction of corncob via a tin-loaded montmorillonite solid acid catalyst[J]. Bioresource Technology, 2015, 176, 242- 248. doi: 10.1016/j.biortech.2014.11.044
10	BHAUMIK P , KANE T , DHEPE P L . Silica and zirconia supported tungsten, molybdenum and gallium oxide catalysts for the synthesis of furfural[J]. Catalysis Science Technology, 2014, 4 (9): 2904- 2907. doi: 10.1039/C4CY00530A
11	ZHANG Z , ZHAO Z K . Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid[J]. Bioresource Technology, 2010, 101 (3): 1111- 1114. doi: 10.1016/j.biortech.2009.09.010
12	PELETEIRO S , SANTOS V , PARAJÓ J C . Furfural production in biphasic media using an acidic ionic liquid as a catalyst[J]. Carbohydrate Polymers, 2016, 53, 421- 428.
13	FEGYVERNEKI D , ORHA L , LANG G , et al. Gamma-valerolactone-based solvents[J]. Tetrahedron London, 2010, 66 (5): 1078- 1081. doi: 10.1016/j.tet.2009.11.013
14	秦玉洁, 王锐, 张军华. γ-戊内酯/水体系下稀酸预处理对玉米秸秆酶解特性的影响[J]. 林业工程学报, 2019, 4 (1): 108- 114.
	QIN Y J , WANG R , ZHANG J H . Structure and enzymatic hydrolysis of corn stover with dilute acid pretreatment in γ-valerolactone/water system[J]. Journal of Forestry Engineering, 2019, 4 (1): 108- 114.
15	QI L , HORVÁTH I . Catalytic conversion of fructose to γ-valerolactone in γ-valerolactone[J]. ACS Catalysis, 2012, 2 (11): 2247- 2249. doi: 10.1021/cs300428f
16	FEI C , THOMAS J S , DANIEL J M , et al. Dehydration of cellulose to levoglucosenone using polar aprotic solvents[J]. Energy Environmental Science, 2015, 8 (6): 1808- 1815. doi: 10.1039/C5EE00353A
17	WANG K , YE J , ZHOU M , et al. Selective conversion of cellulose to levulinic acid and furfural in sulfolane/water solvent[J]. Cellulose, 2017, 24 (3): 1383- 1394. doi: 10.1007/s10570-016-1184-7
18	HUANG Y B , YANG T , LIN Y T , et al. Facile and high-yield synthesis of methyl levulinate from cellulose[J]. Green Chemistry, 2018, 20 (6): 1323- 1334. doi: 10.1039/C7GC02883K
19	PARK G , JEON W , BAN C , et al. Direct catalytic conversion of brown seaweed-derived alginic acid to furfural using 12-tungstophosphoric acid catalyst in tetrahydrofuran/water co-solvent[J]. Energy Conversion and Management, 2016, 118, 135- 141. doi: 10.1016/j.enconman.2016.03.091
20	YANG T , CAI B , CHANG X , et al. Highly efficient and recyclable metal salt catalyst for the production of biodiesel:Toward greener process[J]. Chemistryselect, 2017, 2 (13): 3775- 3782. doi: 10.1002/slct.201700334
21	YANG T , ZHOU Y H , ZHU S Z , et al. Insight into aluminium sulfate catalyzed xylan conversion to furfural in γ-valerolactone/water biphasic solvent under microwave condition[J]. ChemSusChem, 2017, 10 (20): 4066- 4079. doi: 10.1002/cssc.201701290
22	CHOUDHARY V , SANDLER S I , VLACHOS D G . Conversion of xylose to furfural using lewis and Brønstedacid catalysts in aqueous media[J]. ACS Catalysis, 2012, 2 (9): 2022- 2028. doi: 10.1021/cs300265d
23	ZHANG L , YU H , WANG P , et al. Production of furfural from xylose, xylan and corncob in gamma-valerolactone using FeCl₃·6H₂O as catalyst[J]. Bioresource Technology, 2014, 151, 355- 360. doi: 10.1016/j.biortech.2013.10.099
24	GVRBVZ , ELIF I , GALLO J M R , et al. Conversion of hemicellulose into furfural using solid acid catalysts in γ-valerolactone[J]. Angewandte Chemie International Edition, 2013, 52 (4): 1270- 1274. doi: 10.1002/anie.201207334
25	TANG J , GUO X , ZHU L , et al. Mechanistic study of glucose-to-fructose isomerization in water catalyzed by[Al (OH)₂(aq)]⁺[J]. ACS Catalysis, 2015, 5 (9): 5097- 5103. doi: 10.1021/acscatal.5b01237
26	HUI L , DU Y , TANG C , et al. Lignin-derived interconnected hierarchical porous carbon monolith with large areal/volumetric capacitances for supercapacitor[J]. Carbon, 2016, 100, 151- 157. doi: 10.1016/j.carbon.2015.12.075
27	FANG Y , LV Y , CHE R , et al. Two-dimensional mesoporous carbon nanosheets and their derived graphene nanosheets:Synthesis and efficient lithium ion storage[J]. Journal of the American Chemical Society, 2013, 135 (4): 1524- 1530. doi: 10.1021/ja310849c
28	WANG X , LI X , LIU D , et al. Green synthesis of Pt/CeO₂/graphene hybrid nanomaterials with remarkably enhanced electrocatalytic properties[J]. Chemical Communications, 2012, 48 (23): 2885- 2887. doi: 10.1039/c2cc17409j
29	WEINGARTEN R , CONNER W C , HUBER G W . Production of levulinic acid from cellulose by hydrothermal decomposition combined with aqueous phase dehydration with a solid acid catalyst[J]. Energy Environmental Science, 2012, 5 (6): 7559- 7574. doi: 10.1039/c2ee21593d

原料 substrate	糠醛得率/% yield of furfural	5-羟甲基糠醛得率/% yield of 5-hydroxymethylfurfural	液化率/% liquefied conversion
玉米芯corncob	39.5	28.9	86.5
木聚糖xylan	50.2	6.7	95.5
木糖xylose	63.2	19.5	96.0
竹粉bamboo meal	29.7	31.5	80.5

催化剂 catalyst	糠醛得率/% yield of furfural	液化率/% liquefied conversion
Al₂(SO₄)₃	50.2	95.5
MgSO₄	8.8	73.0
CaSO₄	16.2	82.5
KAl(SO₄)₂	46.8	92.5
Na₂SO₄	6.4	75.0
CuSO₄	43.8	86.0
Fe₂(SO₄)₃	39.4	83.5
FeSO₄	10.8	86.5
K₂SO₄	5.1	80.0

[1]	ZHANG Yujie, KONG Fangong, GUO Liuzhu, LIU Xiaoke, ZHAO Xin. Preparation and Adsorption Behavior Study of Larch-based SiO₂@C Composites for Dyes [J]. Chemistry and Industry of Forest Products, 2020, 40(1): 120-128.
[2]	Ying GUAN,Jun RAO,Yule WU,Ran YANG,Hui GAO. Preparation and Characterization of Carboxymethyl Hemicelluloses/Chitosan/Graphene Oxide Composite Film [J]. Chemistry and Industry of Forest Products, 2019, 39(6): 13-20.
[3]	Yanju LU,Zhendong ZHAO,Jing WANG,Shichao XU,Liangwu BI,Yuxiang CHEN. Synthesis and Biological Activity of Isopimaric Furfural Acylhydrazone Derivatives [J]. Chemistry and Industry of Forest Products, 2019, 39(3): 43-48.
[4]	Si LU,Qiong WANG,Xun LI,Wei QI,Zhongming WANG,Zhenhong YUAN. Progress on Preparation and Application of 5-Hydroxymethylfurfural [J]. Chemistry and Industry of Forest Products, 2019, 39(1): 13-22.
[5]	YANG Yan, REN Hao, ZHAI Huamin. Evaluation Method of Solubility of Wheat Straw in LiCl/DMSO Solvent [J]. Chemistry and Industry of Forest Products, 2018, 38(4): 9-12.
[6]	ZHANG Kaiqiang, TANG Gongwen, YAN Zhishan, MA Linrong, HUANG Xin. Effects of Liquid Crystalline Epoxy Resin on the Properties of Bio-based Cardanol-furfural Resin [J]. Chemistry and Industry of Forest Products, 2018, 38(4): 41-46.
[7]	LI Miao, LIU Qiumei, CAI Qinjie, ZHANG Suping. Levulinic Acid Synthesis from Furfural Residue with Synergistic Effect of Catalyst and NaCl [J]. Chemistry and Industry of Forest Products, 2018, 38(4): 69-73.
[8]	LU Yi, ZHENG Zhifeng, HUANG Yuanbo, LI Wenbin. Research Advances in Preparation of Furfural and Its Derivatives by Selective Catalytic Conversion of Hemicellulose [J]. Chemistry and Industry of Forest Products, 2018, 38(3): 1-16.
[9]	YE Jiewang, JIANG Jianchun, MA Zhongqing, ZHANG Weigang, LU Fengzhu. Directional Liquefaction of Bamboo Catalyzed by Cu Doped Porous Metal Oxide [J]. Chemistry and Industry of Forest Products, 2018, 38(3): 48-54.
[10]	ZHANG Qilin, WANG Chao, ZHANG Xueming, YANG Guihua, XU Feng. Improving Conversion of Glucose Dehydration to 5-Hydroxymethylfurfural Catalyzed by Solid Acid in γ-Valerolactone/Water with NaCl as Promoter [J]. Chemistry and Industry of Forest Products, 2018, 38(1): 53-58.
[11]	LI Jiaoyang, HUANG Jizhen, LIU Yuxin, SUN Bing, LIANG Xing, ZHANG Bao. Effect of Laccase Pretreatment on Extract of Bagasse Hemicellulose [J]. Chemistry and Industry of Forest Products, 2018, 38(1): 121-126.
[12]	ZHOU Shuai, MIAO Qingxian, HUANG Liulian, CHEN Lihui. Research Progress in Hemicellulose-based Functional Materials [J]. Chemistry and Industry of Forest Products, 2017, 37(6): 10-18.
[13]	ZHANG Ying, JIA Wenda, FU Yao. Recent Advances in Heterogeneous-catalysis Transformation of 5-Hydroxymethyfurfural to 2,5-Dimethylfuran [J]. Chemistry and Industry of Forest Products, 2017, 37(4): 1-12.
[14]	ZHANG Ying, LI Chuang, FU Yao. Recent Progress in Hydrogenation of Levulinic Acid and Its Esters to γ-Valerolactone [J]. Chemistry and Industry of Forest Products, 2017, 37(3): 10-20.
[15]	QI Xue-zhen, XIE Min-hui, LIN Shao-jie, ZHANG Hai-yan, LIU Xue-jun, LU Mei-zhen, JI Jian-bing. Production of Bio-aviation Fuel Intermediates by Aldol Condensation of Furfural and Methyl Isobutyl Ketone over K⁺/CaO [J]. Chemistry and Industry of Forest Products, 2016, 36(6): 35-40.

Directional Conversion of Hemicellulose into Furfural via Sulfate Catalysts in the Gamma-valerolactone/Water Compound Solvent

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 8

References 29

Related Articles 15

Recommended Articles

Metrics

Comments