糠醛的生物炼制技术研究进展

doi:10.3969/j.issn.1673-5854.2021.06.007

Abstract

Abstract:

Biorefinery is an excellent strategy to deal with the energy crisis and environmental pollution in the new age. Based on biorefinery, low-value biomass resources can be converted into various value-added products. Furfural is one value-added platform chemical from biomass resources, which has important applications in energy, medicine, chemical, and other fields. The industrial production of furfural has come out for nearly one century and is relatively mature nowadays. However, there are still some issues remain to be solved in the industrial production. In order to solve these problems, efforts have been paid on exploring new technologies and progresses. In this paper, the characteristics of furfural were introduced firstly, and the present situation and problems of furfural industrial production technology are summarized, including corrosion of equipment caused by acid catalysts, difficulty in catalyst recycling, water pollution and so on. Then, the research status and problems of furfural preparation by hydrolysis and pyrolysis and the characteristic of the microwave-assisted technology were carefully reviewed. Finally, the future development direction of furfural preparation technology was prospected.

Key words: biomass, furfural, platform compound, hydrolysis, pyrolysis

CLC Number:

TQ35

Yanchun FU, Tengfei GAO, Liping ZHANG, Ruihong MENG, Yang YANG, Xiongwei LI. Advance on Bio-refining for the Production of Furfural[J]. Biomass Chemical Engineering, 2021, 55(6): 59-66.

Figures/Tables 4

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Table 1

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References 53

1	BAKTASH M M , AHSAN L , NI Y H . Production of furfural from an industrial pre-hydrolysis liquor[J]. Separation and Purification Technology, 2015, 149, 407- 412. doi: 10.1016/j.seppur.2015.06.003
2	RACHAMONTREE P , DOUZOU T , CHEENKACHORN K , et al. Furfural: A sustainable platform chemical and fuel[J]. Applied Science and Engineering Progress, 2020, 13 (1): 3- 10.
3	LUO Y P , LI Z , LI X L , et al. The production of furfural directly from hemicellulose in lignocellulosic biomass: A review[J]. Catalysis Today, 2019, 319, 14- 24. doi: 10.1016/j.cattod.2018.06.042
4	LI X D , JIA P , WANG T F . Furfural: A promising platform compound for sustainable production of C₄ and C₅ chemicals[J]. ACS Catalysis, 2016, 6 (11): 7621- 7640. doi: 10.1021/acscatal.6b01838
5	陈雄彪. 糠醛清洁生产工艺研究[J]. 资源节约与环保, 2014, (7): 26- 27.
6	RESEARCH T M. Furfural derivatives-global industry analysis, size, share, growth, trends, and forecast, 2018-2026[R]. New York: Transparency Market Research, 2018.
7	LEE C B T L, WU T Y. A review on solvent systems for furfural production from lignocellulosic biomass[J/OL]. Renewable and Sustainable Energy Reviews, 2021, 137: 110172[2020-11-20]. https://doi.org/10.1016/j.rser.2020.110172.
8	MAMMAN A S , LEE J M , KIM Y C , et al. Furfural: Hemicellulose/xylosederived biochemical[J]. Biofuels, Bioproducts and Biorefining, 2008, 2 (5): 438- 454. doi: 10.1002/bbb.95
9	董晓晨, 叶小宁, 蒋晓燕, 等. 生物质快速热解制糠醛的实验研究及理论探讨综述[J]. 生物质化学工程, 2015, 49 (5): 39- 46. doi: 10.3969/j.issn.1673-5854.2015.05.008
10	LANGE J P , HEIDE E V D , BUIJTENEN J V , et al. Furfural: A promising platform for lignocellulosic biofuels[J]. ChemSusChem, 2012, 5 (1): 150- 166. doi: 10.1002/cssc.201100648
11	WIN D T . Furfural: Gold from garbage[J]. Australian Journal of Chemistry, 2005, 8 (4): 185- 190.
12	YAN K , WU G S , LAFLEUR T , et al. Production, properties and catalytic hydrogenation of furfural to fuel additives and value-added chemicals[J]. Renewable and Sustainable Energy Reviews, 2014, 38, 663- 676. doi: 10.1016/j.rser.2014.07.003
13	VALEKAR A H , LEE M , YOON J W , et al. Catalytic transfer hydrogenation of furfural to furfuryl alcohol under mild conditions over Zr-MOFs: Exploring the role of metal node coordination and modification[J]. ACS Catalysis, 2020, 10 (6): 3720- 3732. doi: 10.1021/acscatal.9b05085
14	MENG X Y , YANG Y S , CHEN L F , et al. A control over hydrogenation selectivity of furfural via tuning exposed facet of Ni catalysts[J]. ACS Catalysis, 2019, 9 (5): 4226- 4235. doi: 10.1021/acscatal.9b00238
15	TAYLOR M J , DURNDELL L J , ISAACS M A , et al. Highly selective hydrogenation of furfural over supported Pt nanoparticles under mild conditions[J]. Applied Catalysis B: Environmental, 2016, 180, 580- 585. doi: 10.1016/j.apcatb.2015.07.006
16	HOYDONCKX H E , VAN RHIJN W M , VAN RHIJN W , et al. Furfural and derivatives[J]. Ullmann's Encyclopedia of Industrial Chemistry, 2007, 16, 285- 309.
17	徐榕徽, 王国胜. 以糠醛为原料的δ-戊内酯合成及应用研究进展[J]. 生物质化学工程, 2020, 54 (1): 60- 66. doi: 10.3969/j.issn.1673-5854.2020.01.010
18	PAPANIKOLAOU G, LANZAFAME P, PERATHONER S, et al. High performance of Au/ZTC based catalysts for the selective oxidation of bio-derivative furfural to 2-furoic acid[J/OL]. Catalysis Communications, 2021, 149: 106234[2020-11-20]. https://doi.org/10.1016/j.catcom.2020.106234.
19	ZHOU X W , LI W J , MABON R , et al. A critical review on hemicellulose pyrolysis[J]. Energy Technology, 2017, 5 (1): 52- 79. doi: 10.1002/ente.201600327
20	LIU H T , HU H R , JAHAN M S , et al. Furfural formation from the pre-hydrolysis liquor of a hardwood kraft-based dissolving pulp production process[J]. Bioresource Technology, 2013, 131, 315- 320. doi: 10.1016/j.biortech.2012.12.158
21	殷艳飞, 房桂干, 施英乔, 等. 生物质转化制糠醛及其应用[J]. 生物质化学工程, 2011, 45 (1): 53- 56. doi: 10.3969/j.issn.1673-5854.2011.01.011
22	赵芷言, 丁佳晶, 夏斐斐, 等. 生物质制备糠醛及其研究进展[J]. 广州化工, 2020, 48 (22): 1- 3, 35. doi: 10.3969/j.issn.1001-9677.2020.22.002
23	CAI C M , ZHANG T Y , KUMAR R , et al. Integrated furfural production as a renewable fuel and chemical platform from lignocellulosic biomass[J]. Journal of Chemical Technology & Biotechnology, 2014, 89 (1): 2- 10.
24	聂一凡, 候其东, 李维尊, 等. 糠醛的水解制备和应用研究进展[J]. 化工进展, 2019, 38 (5): 2164- 2178.
25	BHAUMIK P , DHEPE P L . Efficient, stable, and reusable silicoaluminophosphate for the one-pot production of furfural from hemicellulose[J]. ACS Catalysis, 2013, 3 (10): 2299- 2303. doi: 10.1021/cs400495j
26	BERBAL H G , BERNAZZANI L , GALLETTI A M R . Furfural from corn stover hemicelluloses.A mineral acid-free approach[J]. Green Chemistry, 2014, 16 (8): 3734- 3740. doi: 10.1039/C4GC00450G
27	DENG A J , REN J L , LI H L , et al. Corncob lignocellulose for the production of furfural by hydrothermal pretreatment and heterogeneous catalytic process[J]. RSC Advances, 2015, 5 (74): 60264- 60272. doi: 10.1039/C5RA10472F
28	MITTAL A , BLACK S K , VINZANT T B , et al. Production of furfural from process-relevant biomass-derived pentoses in a biphasic reaction system[J]. ACS Sustainable Chemistry & Engineering, 2017, 5 (7): 5694- 5701.
29	WANG Q , ZHUANG X S , WANG W , et al. Rapid and simultaneous production of furfural and cellulose-rich residue from sugarcane bagasse using a pressurized phosphoric acid-acetone-water system[J]. Chemical Engineering Journal, 2018, 334, 698- 706. doi: 10.1016/j.cej.2017.10.089
30	ZHANG T Y , KUMAR R , WYMAN C E . Enhanced yields of furfural and other products by simultaneous solvent extraction during thermochemical treatment of cellulosic biomass[J]. RSC Advances, 2013, 3 (25): 9809- 9819. doi: 10.1039/c3ra41857j
31	USMANI Z, SHARMA M, GUPTA P, et al. Ionic liquid based pretreatment of lignocellulosic biomass for enhanced bioconversion[J/OL]. Bioresource Technology, 2020, 304: 123003[2020-11-20]. https://doi.org/10.1016/j.biortech.2020.123003.
32	ZHANG L X , YU H B , WANG P , et al. Conversion of xylan, d-xylose and lignocellulosic biomass into furfural using AlCl₃ as catalyst in ionic liquid[J]. Bioresource Technology, 2013, 130, 110- 116. doi: 10.1016/j.biortech.2012.12.018
33	ZHANG Z H , ZHAO Z B 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
34	HUANG J , GUO X Y , XU T Y , et al. Ionic deep eutectic solvents for the extraction and separation of natural products[J]. Journal of Chromatography A, 2019, 1598, 1- 19. doi: 10.1016/j.chroma.2019.03.046
35	LEE C , WU T Y , TING C H , et al. One-pot furfural production using choline chloride-dicarboxylic acid based deep eutectic solvents under mild conditions[J]. Bioresource Technology, 2019, 278, 486- 489. doi: 10.1016/j.biortech.2018.12.034
36	ZHANG L X , YU H , YU H B , et al. Conversion of xylose and xylan into furfural in biorenewable choline chloride-oxalic acid deep eutectic solvent with the addition of metal chloride[J]. Chinese Chemical Letters, 2014, 25 (8): 1132- 1136. doi: 10.1016/j.cclet.2014.03.029
37	WANG R Q , LIANG X F , SHEN F , et al. Mechanochemical synthesis of sulfonated palygorskite solid acid catalysts for selective catalytic conversion of xylose to furfural[J]. ACS Sustainable Chemistry & Engineering, 2020, 8 (2): 1163- 1170.
38	ZHAO Y , XU H , LU K F , et al. Experimental and kinetic study of arabinose conversion to furfural in renewable butanone-water solvent mixture catalyzed by Lewis acidic ionic liquid catalyst[J]. Industrial & Engineering Chemistry Research, 2019, 58 (36): 17088- 17097.
39	CHEN X, CHE Q F, LI S J, et al. Recent developments in lignocellulosic biomass catalytic fast pyrolysis: Strategies for the optimization of bio-oil quality and yield[J/OL]. Fuel Processing Technology, 2019, 196: 106180[2020-11-20]. https: //doi.org/10.1016/j.fuproc.2019.106180.
40	BRANCA C , DI BLASI C , GALGANO A . Catalyst screening for the production of furfural from corncob pyrolysis[J]. Energy & Fuels, 2012, 26 (3): 1520- 1530.
41	张俊姣, 廖航涛, 陆强, 等. 果糖低温快速热解制备糠醛的机理研究[J]. 燃料化学学报, 2013, 41 (11): 1303- 1309.
42	HU B , LU Q , WU Y T , et al. Catalytic mechanism of sulfuric acid in cellulose pyrolysis: A combined experimental and computational investigation[J]. Journal of Analytical and Applied Pyrolysis, 2018, 134, 183- 194. doi: 10.1016/j.jaap.2018.06.007
43	LU Q , DONG C Q , ZHANG X M , et al. Selective fast pyrolysis of biomass impregnated with ZnCl₂ to produce furfural: Analytical Py-GC/MS study[J]. Journal of Analytical and Applied Pyrolysis, 2011, 90 (2): 204- 212. doi: 10.1016/j.jaap.2010.12.007
44	BRANCA C , DI BLASI C , GALGANO A . Pyrolysis of corncobs catalyzed by zinc chloride for furfural production[J]. Industrial & Engineering Chemistry Research, 2010, 49 (20): 9743- 9752.
45	CHEN X , CHEN Y Q , CHEN Z , et al. Catalytic fast pyrolysis of cellulose to produce furan compounds with SAPO type catalysts[J]. Journal of Analytical and Applied Pyrolysis, 2018, 129, 53- 60. doi: 10.1016/j.jaap.2017.12.004
46	LU Q , XIONG W M , LI W Z , et al. Catalytic pyrolysis of cellulose with sulfated metal oxides: A promising method for obtaining high yield of light furan compounds[J]. Bioresource Technology, 2009, 100 (20): 4871- 1876. doi: 10.1016/j.biortech.2009.04.068
47	CHEN X , YANG H P , CHEN Y Q , et al. Catalytic fast pyrolysis of biomass to produce furfural using heterogeneous catalysts[J]. Journal of Analytical and Applied Pyrolysis, 2017, 127, 292- 298. doi: 10.1016/j.jaap.2017.07.022
48	BAI X W, LI J, JIA C X, et al. Preparation of furfural by catalytic pyrolysis of cellulose based on nano Na/Fe-solid acid[J/OL]. Fuel, 2019, 258: 116089[2020-11-20]. https://doi.org/10.1016/j.fuel.2019.116089.
49	LU Q , WANG Z , DONG C Q , et al. Selective fast pyrolysis of biomass impregnated with ZnCl₂: Furfural production together with acetic acid and activated carbon as by-products[J]. Journal of Analytical and Applied Pyrolysis, 2011, 91 (1): 273- 279. doi: 10.1016/j.jaap.2011.03.002
50	LUAUE R , MEMEMDEZ J A , ARENILLAS A , et al. Microwave-assisted pyrolysis of biomass feedstocks: The way forward?[J]. Energy Environmental Science, 2012, 5, 5481- 5487. doi: 10.1039/C1EE02450G
51	KIM E S , LIU S , ABU-OMAR M M , et al. Selective conversion of biomass hemicellulose to furfural using maleic acid with microwave heating[J]. Energy & Fuels, 2012, 26 (2): 1298- 1304.
52	SERRANO-RUIZ J C , CAMPELO J M , FRANCAVILLA M , et al. Efficient microwave-assisted production of furfural from C5 sugars in aqueous media catalysed by brönsted acidic ionic liquids[J]. Catalysis Science & Technology, 2012, 2 (9): 1828- 1832.
53	REN S , LEI H , ZHANG Y , et al. Furfural production from microwave catalytic torrefaction of douglas fir sawdust[J]. Journal of Analytical and Applied Pyrolysis, 2019, 138, 188- 195. doi: 10.1016/j.jaap.2018.12.023

工艺名称 processes	原料 raw materials	催化剂 catalysts	温度/℃ temperature	糠醛得率/% yield of furfural	优缺点 advantages and disadvantages	文献 ref.
Quakers Oats	燕麦壳	硫酸	153	40~52	温度低，停留时间和较高较长；硫酸浓度较高	[7]
Suprayield	硬木	硫酸	230~250	50~70	反应器体积小；停留时间短；糠醛得率高和酸循环利用；投资和维护成本高昂	[8]
Westpro	玉米芯	硫酸	160~165	55	副产物量少，糠醛纯度高，生产成本低	[2]

原料 raw materials	技术要点 technical points	糠醛得率% yield of furfural/%	文献 ref.
软木半纤维素	SAPO-44固体催化剂	63	[25]
玉米秸秆	NbP固体酸	23	[26]
玉米芯	SO₄^2-/SiO₂-Al₂O₃/La³⁺固体酸	21	[27]
玉米秸秆预水解液	水-甲苯双相体系，H₂SO₄催化	76.3	[28]
玉米秸秆预水解液	水-甲基异丁基酮双相体系，H₂SO₄催化	80.1	[28]
甘蔗渣	水-丙酮双相体系，H₃PO₄催化	45.8	[29]
木聚糖	[BMIM]Cl/AlCl₃离子液体催化体系	77	[32]
棕榈叶	草酸-氯化胆碱低共熔溶剂	26.34	[35]
木糖	草酸-氯化胆碱低共熔溶剂，AlCl₃催化	39.8	[36]
木糖	PAL-SO₃H固体催化剂，γ-戊二醛内酯-水双相体系	87	[37]
阿拉伯糖	[BMIM]Cl/AlCl₃离子液体催化剂，水-丁酮双相体系	60	[32]

原料 raw materials	技术要点 technical points	转化率/% conversion rate/%	糠醛得率/% yield of furfural/%	文献 ref.
玉米芯	ZnCl₂浸渍催化热解	—	8.0	[43]
玉米芯	ZnCl₂浸渍催化热解	—	5.79	[40]
玉米芯	Fe₂(SO₄)₃浸渍催化热解	—	4.62	[40]
玉米芯	H₂SO₄浸渍催化热解	—	5.11	[40]
纤维素	ZrCu-SAPO-18原位催化	27.5	—	[45]
纤维素	TiN非原位催化	—	15.3	[47]
纤维素	CaN非原位催化	—	23.0	[47]
纤维素	Na/Fe固体酸非原位催化	64.7	—	[48]

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Advance on Bio-refining for the Production of Furfural

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