Optimization on the Production of Furfural from Corncob in Cheap Ionic Liquid System

doi:10.19894/j.issn.1000-0518.210083

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (02): 272-282.DOI: 10.19894/j.issn.1000-0518.210083

• Full Papers • Previous Articles Next Articles

Optimization on the Production of Furfural from Corncob in Cheap Ionic Liquid System

Ou-Wen HE¹^,²(), Chang-Fu SUN³, Hong-Bing YU¹()

^1.College of Environmental Science and Engineering, Nankai University, Tianjin 300350, China
^2.Department of Civil Engineering, Queen′s University, Kingston, Ontario K7L 3N6, Canada
^3.Shenzhen Federation of Energy Conservation Experts, Shenzhen 518029, China

Received:2021-03-01 Accepted:2021-06-22 Published:2022-02-10 Online:2022-02-09
Contact: Ou-Wen HE,Hong-Bing YU
Supported by:
National Natural Science Foundation of China(BE210751);Research on the Index System of Cleaner Production Performance Evaluation of Liquor Brewing Industrial Based on LCA(CP-2018-YB10)

1. .pdf(165KB)

Abstract

Abstract:

A cheap green ionic liquid triethylammonium hydrogen sulfate [TEA] [HSO₄] was applied as solvent to prepare furfural by microwave heating assisted hydrolysis and dehydration of corncob. The reaction conditions of furfural formation are optimized by the response surface method (RSM), and the total pentose in corncob is effectively converted to obtain 82.2% of furfural. 2-Butanol is used as the extractant to recover furfural. After 4repeatedextractionexperiments, 99.7% of furfural is effectively recovered from [TEA] [HSO₄]. In the recovery experiment of [TEA] [HSO₄], 58.3% and 63.2% of [TEA] [HSO₄] are recycled after the first [TEA] [HSO₄] repeated experiment and the second [TEA] [HSO₄] repeated experiment, respectively. The results of the first and second recycling experiments in [TEA] [HSO₄] show that the yield of 5-hydroxymethylfulfural (HMF) does not decrease significantly, while the yield of furfural decreases from 82.2% to 52.2% and 41.3%, respectively. This experiment provides a new idea for the efficient production of furfural in corncob by catalytic conversion in cheap and green ionic liquid system.

Key words: Corncob, Furfural, Hydroxymethylfulfural, Ionic liquid, Response surface method

CLC Number:

O622.4

Ou-Wen HE, Chang-Fu SUN, Hong-Bing YU. Optimization on the Production of Furfural from Corncob in Cheap Ionic Liquid System[J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 272-282.

Figures/Tables 11

References 37

[1]	罗影龄, 薛智权, 易炜林, 等. 离子液体预处理生物质提高糖化产率[J]. 应用化学, 2014, 31(1):54-60.
	LUO Y L, XUE Z Q, YI W L, et al. Pretreatment of biomass with ionic liquid to improve saccharification yield[J]. Chinese J Appl Chem, 2014, 31(1):54-60.
[2]	ZHANG T, LI W, AN S, et al. Efficient transformation of corn stover to furfural usingp-hydroxybenzenesulfonic acid-formaldehyde resin solid acid [J]. Bioresour Technol, 2018, 264:261-267.
[3]	吴倩倩, 常璇, 马玉龙. 不同酸解聚麦秸产物分析及其动力学[J]. 应用化学, 2015, 32(7):794-800.
	WU Q Q, CHANG X, MA Y L. Depolymerization products and kinetics of wheat straw using different acids[J]. Chinese J Appl Chem, 2015, 32(7):794-800.
[4]	欧阳洪生, 肖竹钱, 蒋成君, 等. 生物质基平台化合物糠醛的研究进展[J]. 应用化工, 2014, 43(10):1903-1907.
	OUYANG H S, XIAO Z Q, JIANG C J. Sources of pollution in furfural production and pollution prevention[J]. Appl Cheml Ind, 2014, 43(10):1903-1907.
[5]	汪文睿, 项东. Al₂(SO₄)₃催化玉米芯直接液化制备糠醛研究[J]. 应用化工, 2019, 48(7):1531-1534.
	WANG W R, XIANG D. Furfural production from direct liquefaction of corncob under catalytic of Al₂(SO₄)₃ [J]. Appl Cheml Ind, 2019, 48(7):1531-1534.
[6]	高月淑, 许敬亮, 袁振宏, 等. 木质纤维原料同步糖化发酵制取生物乙醇研究进展[J]. 生物质化学工程, 2016, 50(3):65-70.
	GAO Y S, XU J L, YUAN Z H, et al. Research progress in bioethanol production through simultaneous saccharification and fermentation with lignocellulose[J]. Biomass Chem Eng, 2016, 50(3):65-70.
[7]	ZHANG L X, GUO X Y, YU K, et al. Furfural production from biomass-derived carbohydrates and lignocellulosic residues via heterogeneous acid catalysts[J]. Ind Crop Prod, 2017, 98:68-75.
[8]	CALCIO G, EMANUELA G C, MAElA M, et al. From waste biomass to chemicals and energy:via microwave-assisted processes[J]. Green Chem, 2019, 21:1202-1235.
[9]	DAI X M. Metal chlorides in ionic liquids to convert saccharide dehydration to 5-hydroxymethyl-furaldehyde[D]. Tianjin University, 2008.
[10]	LEI H, GENG Z, HAO W, et al. Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes[J]. RSC Adv, 2012, 2:11184-11206.
[11]	MARISCAL R, MAIRELES T P, OJED A, et al. Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels[J]. Energy Environ Sci, 2016, 9:1144-1189.
[12]	KOJLI K, PRAJAPATI R, SHARMA B K. Bio-based chemicals from renewable biomass for integrated biorefineries[J]. Energies, 2019, 12(2):233-273.
[13]	王洪莉. 糠醛生产污染来源与污染防治[J]. 环境保护与循环经济, 2013, 33(6):45-46.
	WANG H L. Sources of pollution in furfural production and pollution prevention[J]. Environ Prot Circular Economy, 2013, 33(6):45-46.
[14]	王福余, 刘艳丽, 王崇, 等. 果糖在酸性离子液体中脱水制备5-羟甲基糠醛[J]. 应用化学, 2014, 31(4):424-430.
	WANG F Y, LIU Y L, WANG C, et al. Dehydration of fructose in presence of acidic ionic liquids to prepare 5-hydroxymethylfurfural[J]. Chinese J Appl Chem, 2014, 31(4):424-430.
[15]	XING R, Qi W, HUBER G W. Production of furfural and carboxylic acids from waste aqueous hemicellulose solutions from the pulp and paper and cellulosic ethanol industries[J]. Energy Environ Sci, 2014, 4:2193-2205.
[16]	CAI C M, ZHANG T, KUMAR R, et al. Integrated furfural production as a renewable fuel and chemical platform from lignocellulosic biomass[J]. J Chem Technol Biotechnol, 2014, 89(1):2-10.
[17]	PELETEIRO S, RIVAS S, ALONSO J L, et al. Furfural production using ionic liquids: a review[J]. Bioresour Technol, 2016, 202:181-191.
[18]	LEE C B T L, WU T Y. A review on solvent systems for furfural production from lignocellulosic biomass[J]. Renew Sustainable Energy Rev, 2021, 137:110172.
[19]	PELETEIRO S, SANTOS V, GARROTE G, et al. Furfural production from Eucalyptus wood using an acidic ionic liquid[J]. Carbohydr Polym, 2016, 146:20-25.
[20]	LI C, ZHAO Z. Efficient acid-catalyzed hydrolysis of cellulose in ionic liquid[J]. Adv Synth Catal, 2007, 349(11/12):1847-1850.
[21]	MARINA C, KRISTINA R, RADOJI R. A brief overview of the potential environmental hazards of ionic liquids[J]. Ecotoxicol Environ Saf, 2014, 99:1-12.
[22]	KHASHAYAR G. A review of ionic liquids, their limits and applications[J]. Green Sustainable Chem, 2014, 4:44-53.
[23]	AGNIESZKA B T, FLORENCE J V G, PAUL S F, et al. An economically viable ionic liquid for the fractionation of lignocellulosic biomass[J]. Green Chem, 2017, 19:3078-3102.
[24]	FLORENCE G, FRANCISCO M, SOMNATH S, et al. Rapid pretreatment of Miscanthus using the low-cost ionic liquid triethylammonium hydrogen sulfate at elevated temperatures[J]. Green Chem, 2018, 20:3486-3498.
[25]	BAAQEL H, DIAZ I, TULUS V, et al. Role of life-cycle externalities in the valuation of protic ionic liquids-a case study in biomass pretreatment solvents[J]. Green Chem, 2020, 22:3132-3140.
[26]	BRAND A, GRASVIK J, HALLET J. P, et al. Deconstruction of lignocellulosic biomass with ionic liquids[J]. Green Chem, 2013, 15:550-583.
[27]	CHAMBON C L, FITRIYANTI V, VERD?A P, et al. Fractionation by sequential antisolvent precipitation of grass, softwood, and hardwood lignins isolated using low-cost ionic liquids and water[J]. ACS Sustainable Chem Eng, 2020, 8:3751-3761.
[28]	BRANDA, RAY M J, TO T Q, et al. Ionic liquid pretreatment of lignocellulosic biomass with ionic liquid-water mixtures[J]. Green Chem, 2011, 13:2489-2499.
[29]	ZAHARI S M S N S, AMIN A T M, HALIM N M, et al. Deconstruction of Malaysian agro-wastes with inexpensive and bifunctional triethylammonium hydrogen sulfate ionic liquid[C]. Proceedings of the AIP Conference Proceedings; 2018.
[30]	SHIKH Z S M S N, HAZEEQ A L K. Triethylammonium hydrogen sulfate ionic liquid as a low-cost solvent: a short review of synthesis, analysis and applications[C]. AIP Conference Proceedings, 2018.
[31]	SLUITER A. Determination of structural carbohydrates and lignin in biomass[J]. Biomass Anal Technol Team Lab Anal Proced, 2004.
[32]	刘苏, 李宁, 戴晓莉, 等. 响应面法优化葡萄糖脱水制备5-羟甲基糠醛[J]. 淮阴师范学院学报(自然科学版), 2019, 18(2):130-137.
	LIU S, LI N, DAI X L, et al. Optimization of glucose dehydration into 5-hydroxymethylfulfural by response surface methodology[J]. J Huaiyin Teachers College (Nat Sci Ed), 2019, 18(2):130-137.
[33]	EMANUELA C G, GIANCARLO C, MAELA M, et al. From waste biomass to chemicals and energy via microwave-assisted processes[J]. Green Chem, 2019, 21:1202-1235.
[34]	LI X, LIU Q, LUO C, et al. Kinetics of furfural production from corn cob in γ-valerolactone using diluted sulfuric acid as catalyst[J]. ACS Sustainable Chem Eng, 2017, 5:8587-8593.
[35]	ROQUE L R, MORGADO G P, NASCIMENTO V M, et al. Liquid-liquid extraction: a promising alternative for inhibitors removing of pentoses fermentation[J]. Fuel, 2019, 242:775-787.
[36]	ZHANG Y, GUO X, XU J, et al. Liquid-liquid equilibrium for ternary systems, water+5-hydroxymethylfurfural+(1-butanol, isobutanol, methyl isobutyl ketone), at 313.15, 323.15, and 333.15 K[J]. J Chem Eng Data, 2018, 63:2775-2782.
[37]	ANASTAS P, NICOLAS E. Green chemistry: principles and practice[J]. Chem Soc Rev, 2010, 39(1):301-312.

编号	生料	催化剂质量分数	反应时间	HMF收率Y₁	糠醛收率Y₂
Entry	Substrate	w（catalyst）／%	Reaction time／min	HMF yield Y₁／%	／% Furfural yield Y₂
1	木糖醇 ^b	0	30	1.7±0.4	16.8±1.7
1	Xylitol	0	30	1.7±0.4	16.8±1.7
2	木糖醇 ^b	0	120	2.5±0.9	14.6±2.2
2	Xylitol	0	120	2.5±0.9	14.6±2.2
3	木糖醇 ^a	0	5	2.9±0.5	20.3±1.2
3	Xylitol	0	5	2.9±0.5	20.3±1.2
4	玉米芯 ^a	0	5	5.8±0.4	3.1±0.1
4	Corncob	0	5	5.8±0.4	3.1±0.1
5	玉米芯 ^a	3.3盐酸	5	5.8±1.0	14.9±2.7
5	Corncob	HCl	5	5.8±1.0	14.9±2.7
6	玉米芯 ^a	3.3乙酸	5	4.3±0.1	4.9±2.7
6	Corncob	Acetic acid	5	4.3±0.1	4.9±2.7
7	木糖醇 ^a	3.3%盐酸	5	2.9±0.2	20.4±1.2
7	Xylitol	HCl	5	2.9±0.2	20.4±1.2
8	木糖醇 ^a	3.3乙酸	5	0.1±0.1	1.5±1.2
8	Xylitol	Acetic acid	5	0.1±0.1	1.5±1.2

编号	生料	催化剂质量分数	反应时间	HMF收率Y₁	糠醛收率Y₂
Entry	Substrate	w（catalyst）／%	Reaction time／min	HMF yield Y₁／%	／% Furfural yield Y₂
1	木糖醇 ^b	0	30	1.7±0.4	16.8±1.7
1	Xylitol	0	30	1.7±0.4	16.8±1.7
2	木糖醇 ^b	0	120	2.5±0.9	14.6±2.2
2	Xylitol	0	120	2.5±0.9	14.6±2.2
3	木糖醇 ^a	0	5	2.9±0.5	20.3±1.2
3	Xylitol	0	5	2.9±0.5	20.3±1.2
4	玉米芯 ^a	0	5	5.8±0.4	3.1±0.1
4	Corncob	0	5	5.8±0.4	3.1±0.1
5	玉米芯 ^a	3.3盐酸	5	5.8±1.0	14.9±2.7
5	Corncob	HCl	5	5.8±1.0	14.9±2.7
6	玉米芯 ^a	3.3乙酸	5	4.3±0.1	4.9±2.7
6	Corncob	Acetic acid	5	4.3±0.1	4.9±2.7
7	木糖醇 ^a	3.3%盐酸	5	2.9±0.2	20.4±1.2
7	Xylitol	HCl	5	2.9±0.2	20.4±1.2
8	木糖醇 ^a	3.3乙酸	5	0.1±0.1	1.5±1.2
8	Xylitol	Acetic acid	5	0.1±0.1	1.5±1.2

自变量	自变量范围水平
Factor	Range
Factor	－1	+1
X₁（反应温度Reaction temperature／℃）	80	120
X₂（反应时间Reaction time／min）	0	20
X₃（盐酸量V（HCl）／μL）	34	85
X₄（加热功率Heating power／W）	50	300
X₅（［TEA］［HSO₄］质量分数Mass fraction of［TEA］［HSO₄］）	80	90

自变量	自变量范围水平
Factor	Range
Factor	－1	+1
X₁（反应温度Reaction temperature／℃）	80	120
X₂（反应时间Reaction time／min）	0	20
X₃（盐酸量V（HCl）／μL）	34	85
X₄（加热功率Heating power／W）	50	300
X₅（［TEA］［HSO₄］质量分数Mass fraction of［TEA］［HSO₄］）	80	90

差异源	平方和	自由度	均方	F值	P值	?
Source	Sum of squares	Degree of freedom（df）	Mean square	F-value	P-value	?
Model	1312.95	20	65.65	2.44	0.018 2	Significant
X₁	138.01	1	138.01	5.12	0.032 6	?
X₂	129.29	1	129.29	4.80	0.038 0	?
X₃	310.82	1	310.82	11.53	0.002 3	?
X₄	1.17	1	1.17	0.04	0.836 8	?
X₅　X₁X₂	86.4012.01	11	86.4012.01	3.210.45	0.085 50.510 6	?
X₁X₃	49.01	1	49.01	1.82	0.189 6	?
X₁X₄	6.84	1	6.84	0.25	0.618 7	?
X₁X₅	16.82	1	16.82	0.62	0.436 9	?
X₂X₃	13.78	1	13.78	0.51	0.481 2	?
X₂X₄	1.36	1	1.36	0.05	0.824 0	?
X₂X₅	77.50	1	77.50	2.88	0.102 3	?
X₃X₄	0.28	1	0.28	0.01	0.919 4	?
X₃X₅	7.41	1	7.41	0.28	0.604 6	?
X₄X₅	10.81	1	10.81	0.40	0.532 2	?
	121.54	1	121.54	4.51	0.043 8	?
	132.15	1	132.15	4.90	0.036 1	?
	14.56	1	14.56	0.54	0.469 2	?
	221.62	1	221.62	8.22	0.008 3	?
	0.34	1	0.34	0.01	0.911 7	?
Residual	673.71	25	26.95	?	?	?
Lack of Fit	661.08	22	30.05	7.14	0.0651	Not significant
Pure Error	12.63	3	4.21	?	?	?
Cor Total	1 986.66	45	?	?	?	?

Optimization on the Production of Furfural from Corncob in Cheap Ionic Liquid System

RichHTML

PDF

Supplement

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 37

Related Articles 15

Recommended Articles

Metrics

Comments

?	?	?	自变量Factor		?	因变量Response
编号	温度／	时间	盐酸量	功率	［TEA］［HSO₄］质量分数	HMF产率Y₃	糠醛产率Y₄
Entry	Temperature／℃	Time／min	V（HCl）／μL	Power／W	w（［TEA］［HSO₄］）／%	HMF yield	Furfural yield
Entry	Temperature／℃	Time／min	V（HCl）／μL	Power／W	w（［TEA］［HSO₄］）／%	Y₃／%	Y₄／%
1	120	20	34	300	90	5.4	50.8
2	100	10	60	175	85	2.3	46.7
3	120	0	85	300	80	3.1	50.8
4	80	0	85	50	90	3.6	38.4
5	120	0	85	50	80	9.2	60.7
6	120	0	34	300	80	13.1	57.5
7	80	0	85	50	80	0.0	39.1
8	80	20	85	50	90	4.4	43.0
9	100	10	60	300	85	15.1	62.8
10	80	0	34	50	90	17.2	55.2
11	80	0	34	300	80	9.7	30.1
12	80	0	34	50	80	1.5	3.0
13	120	20	34	300	80	14.1	69.2
14	100	20	60	175	85	7.9	61.1
15	80	20	34	300	80	1.8	18.2
16	100	10	34	175	85	21.0	62.1
17	120	20	85	50	90	0.0	47.1
18	120	0	85	50	90	4.4	30.8
19	120	0	34	300	90	15.9	60.5
20	80	20	34	300	90	8.2	44.8
21	120	10	60	175	85	5.9	54.9
22	120	0	85	300	90	11.0	60.7
23	120	20	85	300	90	0.0	32.2
24	80	0	85	300	90	8.7	37.0
25	100	10	0.07	175	90	16.9	52.3
26	80	20	85	50	80	0.0	21.8
27	120	0	34	50	90	26.4	69.9
28	120	20	85	300	80	2.3	48.3
29	100	10	60	175	80	4.9	14.7
30	80	10	60	175	85	2.6	37.9
31	80	0	34	300	90	5.4	25.5
32	100	0	60	175	85	0.0	23.4
33	80	0	85	300	80	2.3	13.8
34	80	20	34	50	80	3.1	30.3
35	80	20	85	300	90	3.6	47.4
36	100	10	60	175	85	6.4	65.3
37	100	10	60	175	85	6.3	65.1
38	100	10	60	175	85	6.4	66.2
39	120	20	34	50	90	9.0	63.0
40	80	20	85	300	80	0.0	27.4
41	120	0	34	50	80	7.7	50.1
42	80	20	34	50	90	0.0	32.4
43	120	20	85	50	80	5.4	51.7
44	100	10	60	50	85	26.4	40.2
45	120	20	34	50	80	7.7	63.7
46	100	10	85	175	85	6.4	57.7

编号 Entry	反应温度 Temperature／℃	反应时间 Reactiontime／min	盐酸量 V（HCl）／μL	功率 Power／W	［TEA］［HSO₄］质量分数 w（［TEA］［HSO₄］）／%	P-HMF收率 P-HMF yield Y₃／%	P-糠醛收率 P-furfural yield Y₄／%	E-HMF收率 E-HMF yield Y₁／%	E-糠醛收率 E-furfural yield Y₂／%
1	110	7	34	50	87	25.9	74.8	24.5±0.8	81.9±1.1
2	110	8	34	300	87	24.4	74.4	24.1±0.2	82.2±4.3

[1]	Yu-Wen YANG, Jing-Yao QI, Lin LI, Guo-Ning CHU, Sai WANG, Yu ZHANG, Shuang ZHANG. Selective Oxidation of 5-Hydroxymethylfurfural to 2，5-Furandicarboxylic Acid over Ru Supported on Magnetic NiFe₂O₄ [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 879-887.
[2]	Hui-Hui LI, Kai-Sheng YAO, Ya-Nan ZHAO, Li-Na FAN, Yu-Lin TIAN, Wei-Wei LU. Ionic Liquid-Modulated Synthesis of Pt-Pd Bimetallic Nanomaterials and Their Catalytic Performance for Ammonia Borane Hydrolysis to Generate Hydrogen [J]. Chinese Journal of Applied Chemistry, 2023, 40(4): 597-609.
[3]	Qi-Hang CHEN, Fei-Jian XU, Feng WANG, Shuang-Chan FU, Ying-Hao YU. Research Progress of Deep Eutectic Solvent and Its Application Prospects as Antistatic Agents [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 341-359.
[4]	Shuang WU, De-Yang ZHAO, Sheng-Han WU, Li-Gang WEI, Na LIU, Qing-Da AN. Insights into the Dissolution of Lignin Model Phenolic Monomer in 1‑Butyl‑3‑methylimidazolium Methanesulfonate Aqueous Solutions Using Two‑Dimensional Correlation Infrared Spectroscopy [J]. Chinese Journal of Applied Chemistry, 2022, 39(10): 1600-1609.
[5]	NIU Zhan-Ning, TANG Hao-Qing, ZHENG Chao, TIAN Tian, ZHENG Li-Yun. Study on [RESA]Br@-COOH@Fe₃O₄ with Density Functional Theory [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 825-835.
[6]	ZHOU Chao, SHENG Cheng-Ju, WEN Lin-Lin. Preparation of Imidazolium Salt-based Poly(ionic liquids) Antibacterial Agent and Its Application in Hydrogel Dressing [J]. Chinese Journal of Applied Chemistry, 2021, 38(1): 51-59.
[7]	LIU Ning, WANG Danfeng, WU Suyun, LIU Shuilin, FU Lin, LIU Yuejin. Catalytic Synthesis of Bisphenol F over Short-Channeled Mesoporous Molecular Sieve Zr-Ce-SBA-15 Supported Acidic Ionic Liquids [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 1038-1047.
[8]	GUO Hui, YIN Yuanyuan, ZHANG Xueying, ZHUANG Yuwei, JIAN Cao, ZHANG Guobao. Synthesis of N-Cyanoethyl-N-hydroxyethylaniline Catalyzed by Acdic Ionic Liquid [J]. Chinese Journal of Applied Chemistry, 2020, 37(5): 512-517.
[9]	MA Hao, ZHAO Xue, LI Kunlan, SHAO Guolin, AN Qingda, YANG Liyu, WEI Ligang. Evaluation of Silane Imidazolium Bis(trifluoromethane)sulfonimide Ionic Liquid Stationary Phase for Gas Chromatography [J]. Chinese Journal of Applied Chemistry, 2020, 37(4): 447-454.
[10]	ZHANG Shuang, ZHANG Long. Dehydration of Fructose into 5-Hydroxymethylfurfural Catalyzed by Ethylene Tar Char Sulfonic Acid [J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 314-321.
[11]	YU Changmu, ZHANG Rong, LU Xiaoluan, YANG Min, PENG Qianrong. Preparation of Imm-Fe³⁺-IL with Peroxidase Activity and Its Colorimetric Determination of H₂O₂ and Glucose [J]. Chinese Journal of Applied Chemistry, 2020, 37(10): 1211-1220.
[12]	GAO Bo, YANG Hongwei, TIAN Shaopeng, ZHAO Yuzhen, TIAN Tian. Solubility Properties of 1-Alkyl-4-amino-1,2,4-triazolium Energetic Ionic Liquids [J]. Chinese Journal of Applied Chemistry, 2019, 36(9): 1044-1052.
[13]	SONG Feiyue, XUE Yongbo, GAO Xin, BAI Ling, LI Jing, DENG Yun, XIE Lijuan, RUAN Wenquan. Palladium(Ⅱ) Extraction Using Different Ionic Liquid-Based Aqueous Biphasic Systems [J]. Chinese Journal of Applied Chemistry, 2019, 36(3): 335-340.
[14]	GUO Yijiang, CHEN Qingde, SHEN Xinghai. Syntheses and Properties of Novel Boron-Containing Ionic Liquids 1-Alkyl-3-methylimidazolium Benzyoltrifluoroborates [J]. Chinese Journal of Applied Chemistry, 2019, 36(10): 1186-1193.
[15]	ZHU Yun, HONG Liang, JIN Baokang. Construction and Characterization of a High Temperature Infrared Spectroelectrochemical Thin-Layer Cell [J]. Chinese Journal of Applied Chemistry, 2019, 36(1): 107-113.

差异源	平方和	自由度	均方	F值	P值	?
Source	Sum of squares	df	Mean square	F-value	P-value	?
Model	8 280.92	20	414.05	2.33	0.023 6	Significant
X₁	4 171.40	1	4 171.40	23.43	＜0.000 1	?
X₂	61.96	1	61.96	0.35	0.560 5	?
X₃	180.78	1	180.78	1.02	0.323 3	?
X₄	0.34	1	0.34	0.00	0.965 5	?
X₅	581.42	1	581.42	3.27	0.082 8	?
X₁X₂	45.60	1	45.60	0.26	0.617 2	?
X₁X₃	534.65	1	534.65	3.00	0.095 4	?
X₁X₄	4.50	1	4.50	0.03	0.875 0	?
X₁X₅	979.03	1	979.03	5.50	0.027 3	?
X₂X₃	34.03	1	34.03	0.19	0.665 7	?
X₂X₄	0.36	1	0.36	0.00	0.964 4	?
X₂X₅	57.24	1	57.24	0.32	0.575 7	?
X₃X₄	0.50	1	0.50	0.00	0.958 2	?
X₃X₅	101.53	1	101.53	0.57	0.457 2	?
X₄X₅	7.80	1	7.80	0.04	0.835 9	?
	13.32	1	13.32	0.07	0.786 7	?
	103.35	1	103.35	0.58	0.453 2	?
	308.04	1	308.04	1.73	0.200 3	?
	19.01	1	19.01	0.11	0.746 6	?
	571.54	1	571.54	3.21	0.085 3	?
Residual	4 450.69	25	178.03	?	?	?
Lack of Fit	4 183.08	22	190.14	2.13	0.293 2	Not significant
Pure Error	267.61	3	89.20	?	?	?
Cor Total	12731.60	45	?	?	?	?

差异源	平方和	自由度	均方	F值	P值	?
Source	Sum of squares	df	Mean square	F-value	P-value	?
Model	8 280.92	20	414.05	2.33	0.023 6	Significant
X₁	4 171.40	1	4 171.40	23.43	＜0.000 1	?
X₂	61.96	1	61.96	0.35	0.560 5	?
X₃	180.78	1	180.78	1.02	0.323 3	?
X₄	0.34	1	0.34	0.00	0.965 5	?
X₅	581.42	1	581.42	3.27	0.082 8	?
X₁X₂	45.60	1	45.60	0.26	0.617 2	?
X₁X₃	534.65	1	534.65	3.00	0.095 4	?
X₁X₄	4.50	1	4.50	0.03	0.875 0	?
X₁X₅	979.03	1	979.03	5.50	0.027 3	?
X₂X₃	34.03	1	34.03	0.19	0.665 7	?
X₂X₄	0.36	1	0.36	0.00	0.964 4	?
X₂X₅	57.24	1	57.24	0.32	0.575 7	?
X₃X₄	0.50	1	0.50	0.00	0.958 2	?
X₃X₅	101.53	1	101.53	0.57	0.457 2	?
X₄X₅	7.80	1	7.80	0.04	0.835 9	?
	13.32	1	13.32	0.07	0.786 7	?
	103.35	1	103.35	0.58	0.453 2	?
	308.04	1	308.04	1.73	0.200 3	?
	19.01	1	19.01	0.11	0.746 6	?
	571.54	1	571.54	3.21	0.085 3	?
Residual	4 450.69	25	178.03	?	?	?
Lack of Fit	4 183.08	22	190.14	2.13	0.293 2	Not significant
Pure Error	267.61	3	89.20	?	?	?
Cor Total	12731.60	45	?	?	?	?