Biomass Chemical Engineering ›› 2021, Vol. 55 ›› Issue (4): 43-58.doi: 10.3969/j.issn.1673-5854.2021.04.007
• Review Comment • Previous Articles Next Articles
Hongbo SHEN, Xinglong LI, Yao FU()
Received:
2020-07-13
Online:
2021-07-30
Published:
2021-07-10
Contact:
Yao FU
E-mail:fuyao@ustc.edu.cn
CLC Number:
Hongbo SHEN, Xinglong LI, Yao FU. Recent Advances in Synthesis of Alkoxymethylfuran Ether from Biomass Resources[J]. Biomass Chemical Engineering, 2021, 55(4): 43-58.
Table 1
Etherification of HMF with ethanol under various acid catalysts"
序号 No. | 催化剂 catalyst | 温度/℃ temperature | 反应时间/h reaction time | 转化率/% conversion | EMF收率/% yield of EMF | EL收率/% yield of EL | 文献 ref. |
1 | HY沸石HY zeolite | 70 | 24 | — | 8.5 | — | [ |
2 | Al-MCM-41(Si/Al=75) | 140 | 5 | 61 | — | — | [ |
3 | Al-MCM-41(Si/Al=50) | 140 | 5 | 100 | 68 | 10 | [ |
4 | Al-MCM-41(Si/Al=25) | 140 | 5 | 100 | 37 | 47 | [ |
5 | SBA-15 | 140 | 5 | 75 | — | — | [ |
6 | ZrO2-SBA-15 | 140 | 5 | 100 | 76 | 23 | [ |
7 | Al-TUD-1 | 140 | 4 | 88 | 81 | — | [ |
8 | Amberlyst-15 | 75 | 24 | — | 55 | 8 | [ |
9 | Amberlite IR 120 | 75 | 24 | — | 33 | 7 | [ |
10 | Dowex50WX8 | 75 | 24 | — | 45 | 9 | [ |
11 | Dowex DR2030 | 75 | 24 | — | 57 | 8 | [ |
12 | 硅硫酸silica sulfuric acid | 75 | 24 | — | 36 | 7 | [ |
13 | HPW-K-10 | 100 | 10 | — | 91.5 | — | [ |
14 | H4SiW12O40 | 90 | 2 | 81.3 | 86.5 | 4.6 | [ |
15 | 20%H4SiW12O40/MCM-41 | 90 | 2 | 84.8 | 82.7 | 4.3 | [ |
16 | 40%H4SiW12O40/MCM-41 | 90 | 2 | 80.1 | 85.8 | 4.6 | [ |
17 | 40%H4SiW12O40/MCM-41 | 90 | 4 | 92 | 84.1 | 5.8 | [ |
18 | 60%H4SiW12O40/MCM-41 | 90 | 2 | 78.9 | 83.2 | 4.4 | [ |
19 | [MIMBS]3PW12O40 | 100 | 10 | — | 91.5 | — | [ |
20 | 硫酸化纤维素cellulose sulfates | 100 | 10 | — | 84.4 | — | [ |
21 | SiO2-SO3H | 100 | 12 | — | 83.3 | — | [ |
22 | Fe3O4@SiO2-SO3H | 100 | 10 | — | 89.3 | — | [ |
23 | Fe3O4@C-SO3H | 100 | 12 | — | 88.4 | — | [ |
24 | [BmimSO3H]3PW12O40 | 70 | 24 | 98.7 | 90.7 | — | [ |
25 | AlCl3 | 100 | 5 | — | 92.9 | — | [ |
Table 2
Etherification of fructose to EMF"
序号 No. | 催化剂 catalyst | 溶剂体系 solvent system | 反应条件 reaction condition | EMF收率/% yield of EMF | 文献 ref. |
1 | H2SO4 | EtOH | 82.5 ℃,6 h | 60 | [ |
2 | HCl | EtOH | 120 ℃,2 h | 40 | [ |
3 | MCM-41-HPW | EtOH | 100 ℃,12 h | 42.9 | [ |
4 | HPW-K-10 | EtOH | 100 ℃,24 h | 61.5 | [ |
5 | 硫酸化纤维素cellulose sulfates | EtOH | 100 ℃,12 h | 72.5 | [ |
6 | Glu-TsOH-Ti | EtOH | 100 ℃,30 h | 66 | [ |
7 | SiO2-SO3H | EtOH | 100 ℃,12 h | 63.1 | [ |
8 | Fe3O4@SiO2-SO3H | EtOH | 100 ℃,10 h | 72.5 | [ |
9 | BF3·(Et)2O/AlCl3·6H2O | EtOH | 110 ℃,3 h | 55 | [ |
10 | AlCl3 | EtOH | 100 ℃,11 h | 71.2 | [ |
11 | CrCl3 | EtOH | 100 ℃,12 h | 33 | [ |
12 | CuSO4 | EtOH | 110 ℃,10 h | 45.2 | [ |
13 | Fe2(SO4)3 | EtOH | 120 ℃,10 h | 47.7 | [ |
Table 3
The effects of different solid acid catalysts on the distribution for the alcoholysis of fructose to EMF[29]"
序号 No. | 树脂型催化剂 resin catalyst | EMF收率/% yield of EMF | EL收率/% yield of EL | EMFDA收率/% yield of EMFDA | HMF收率/% yield of HMF |
1 | Amberlyst-15 | 71 | 16 | 10 | — |
2 | Amberlite IR120 | 32 | 9 | 5 | 16 |
3 | Dowex50WX8 | 56 | 14 | 7 | — |
4 | Dowex DR2030 | 68 | 16 | 6 | — |
5 | 硅硫酸silica sulfuric acid | 69 | 17 | 9 | — |
Table 4
Effect of solvent system on the conversion of fructose to EMF[60]"
序号 No. | 溶剂组成solvent systems | 果糖转化率/% conversion of fructose | HMF收率/% yield of HMF | EMF收率/% yield of EMF | EL收率/% yield of EL |
V(H2O): V(DMSO): V(EtOH) | |||||
1 | 0:3:7 | 99 | 6 | 64 | 18 |
2 | 0.5:2.5:7 | 98 | 23 | 39 | 22 |
3 | 1:2:7 | 96 | 34 | 22 | 24 |
4 | 2:1:7 | 93 | 37 | 9 | 28 |
5 | 3:0:7 | 88 | 22 | 5 | 37 |
Table 5
Conversion of different biomass substrates to MMF"
序号 No. | 底物 substrate | 溶剂体系 solvent systems | 催化剂 catalyst | 反应条件 reaction condition | MMF收率/% yield of MMF | ML收率/% yield of ML | 文献 ref. |
1 | 纤维素cellulose | 甲醇methanol | H2SO4 | 183 ℃,12 min | 2.7 | 37.8 | [ |
2 | 纤维素cellulose | 甲醇methanol | CF3SO3H | 193 ℃,10 min | 1.5 | 22.3 | [ |
3 | 纤维素cellulose | 甲醇methanol | TsOH | 210 ℃,30 min | 0.5 | 34.8 | [ |
4 | 纤维素cellulose | 甲醇methanol | SO2 | 210 ℃,75 min | 0.6 | 18.2 | [ |
5 | 纤维素cellulose | V(CH3OH): V(H2O)=7:3 | H2SO4 | 189 ℃,8 min | 1.1 | 18.1 | [ |
6 | 纤维素cellulose | V(CH3OH): V(CCl4)=1:1 | H2SO4 | 194 ℃,5 min | TR | 45.5 | [ |
7 | 纤维素cellulose | V(CH3OH): V(PhMe)=1:1 | H2SO4 | 195 ℃,7 min | 1.8 | 39.8 | [ |
8 | 纤维素cellulose | V(CH3OH): V(CYH)=1:1 | H2SO4 | 208 ℃,3 min | 0.4 | 37.1 | [ |
9 | 果糖fructose | 甲醇methanol | H2SO4 | 180 ℃,30 s | 38.7 | — | [ |
10 | 果糖fructose | 甲醇methanol | HCl | 80 ℃,8 h | 3 | — | [ |
11 | 果糖fructose | V(CH3OH): V(THF)=1:1 | Amberlyst-15 | 120 ℃,180 min | 47 | 14.4 | [ |
12 | 果糖fructose | V(CH3OH): V(Hex)=1:4.8 | [MSPIM]Cl | 100 ℃,20 min | 57 | 9 | [ |
13 | 果糖fructose | 超临界甲醇supercritical methanol | H2SO4 | 240 ℃,30 s | 79 | — | [ |
14 | 5-羟甲基糠醛 5 -(hydroxymethyl)urfural | 甲醇methanol | Al-NbP-pH2 | 180 ℃,360 min | 79.5 | 11.2 | [ |
1 | OMIDVARBORNA H , KUMAR A , KIM D S . Recent studies on soot modeling for diesel combustion[J]. Renewable & Sustainable Energy Reviews, 2015, 48, 635- 647. |
2 |
CORMA A , TORRE O , RENZ M , et al. Production of high-quality diesel from biomass waste products[J]. Angewandte Chemie International Edition, 2011, 50 (10): 2375- 2378.
doi: 10.1002/anie.201007508 |
3 |
HUBER G W , IBORRA S , CORMA A . Synthesis of transportation fuels from biomass: Chemistry, catalysts, and engineering[J]. Chemical Reviews, 2006, 106 (9): 4044- 409.
doi: 10.1021/cr068360d |
4 | WERPY T , PETERSEN G , ADEN A , et al. Top Value Added Chemicals from Biomass.Volume I: Results of Screening for Potential Candidates from Sugars and Synthesis Gas[M]. Washington DC: Department of Energy, 2004. |
5 |
蒋剑春. 生物质能源应用研究现状与发展前景[J]. 林产化学与工业, 2002, 22 (2): 75- 80.
doi: 10.3321/j.issn:0253-2417.2002.02.018 |
6 |
吕微, 蒋剑春, 刘石彩, 等. 生物质炭成型燃料的制备及性能研究进展[J]. 生物质化学工程, 2010, 44 (5): 48- 52.
doi: 10.3969/j.issn.1673-5854.2010.05.011 |
7 |
SHYLESH S , GOKHALE A A , HO C R , et al. Novel strategies for the production of fuels, lubricants, and chemicals from biomass[J]. Accounts of Chemical Research, 2017, 50 (10): 2589- 2597.
doi: 10.1021/acs.accounts.7b00354 |
8 |
王英雄, 侯相林, 朱玉雷. 糖类衍生物催化制备含氧液体燃料和精细化学品[J]. 生物产业技术, 2017, (3): 48- 55.
doi: 10.3969/j.issn.1674-0319.2017.03.007 |
9 |
SCHIFTER I , GONZÁLEZ U , GONZÁLEZ-MACÍAS C . Effects of ethanol, ethyl-tert-butyl ether and dimethyl-carbonate blends with gasoline on SI engine[J]. Fuel, 2016, 183, 253- 261.
doi: 10.1016/j.fuel.2016.06.051 |
10 |
SOTO R , FITE C , RAMIREZ E , et al. Equilibrium conversion, selectivity and yield optimization of the simultaneous liquid-phase etherification of isobutene and isoamylenes with ethanol over Amberlyst-35[J]. Fuel Processing Technology, 2016, 142, 201- 211.
doi: 10.1016/j.fuproc.2015.09.032 |
11 | NEL R J J , KLERK A D . Dehydration of C5-C12 linear 1-alcohols over η-alumina to fuel ethers[J]. Industrial & Engineering Chemistry Research, 2009, 48 (11): 5230- 5238. |
12 |
BRINGUE R , RAMIREZ E , IBORRA M , et al. Influence of acid ion-exchange resins morphology in a swollen state on the synthesis of ethyl octyl ether from ethanol and 1-octanol[J]. Journal of Catalysis, 2013, 304, 7- 21.
doi: 10.1016/j.jcat.2013.03.006 |
13 |
JADHAV D , GRIPPO A M , SHYLESH S , et al. Production of biomass-based automotive lubricants by reductive etherification[J]. ChemSusChem, 2017, 10, 2527- 2533.
doi: 10.1002/cssc.201700427 |
14 | WANG S , ZHANG Z , LIU B , et al. Silica coated magnetic Fe3O4 nanoparticles supported phosphotungstic acid: A novel environmentally friendly catalyst for the synthesis of 5-ethoxymethylfurfural from 5-hydroxymethylfurfural and fructose[J]. Catalysis Science & Technology, 2013, 3 (8): 2104- 2112. |
15 |
张秋云, 蔡杰, 张玉涛, 等. 基于生物质转化制备5-乙氧基甲基糠醛研究进展[J]. 精细石油化工, 2015, 32 (1): 42- 47.
doi: 10.3969/j.issn.1003-9384.2015.01.011 |
16 | MASCAL M , NIKITIN E B . Direct, high-yield conversion of cellulose into biofuel[J]. Angewandte Chemie International Edition, 2010, 47, 7924- 7926. |
17 |
LANGE J P , HEIDE E , BUIJTENEN J , et al. Furfural: A promising platform for lignocellulosic biofuels[J]. ChemSusChem, 2012, 5 (1): 150- 166.
doi: 10.1002/cssc.201100648 |
18 | CAMARA J S , ALVES M A , MARQUES J C . Changes in volatile composition of Madeira wines during their oxidative ageing[J]. Analytica Chimica Acta, 2006, 563 (1/2): 188- 197. |
19 | FITZPATRICK S W . The biofine technology: A "bio-refinery" concept based on thermochemical conversion of cellulosic biomass[J]. ACS Symposium Series, 2006, 921, 271- 287. |
20 |
RAS E J , MCKAY B , ROTHENBERG G . Understanding catalytic biomass conversion through data mining[J]. Topics in Catalysis, 2010, 53, 1202- 1208.
doi: 10.1007/s11244-010-9563-z |
21 | 陈涛, 彭林才. 新型生物燃料5-乙氧基甲基糠醛的合成进展[J]. 化学通报, 2018, 81 (1): 45- 51. |
22 | 徐桂转, 陈炳霖, 张少浩, 等. 生物质转化制备5-乙氧基甲基糠醛液体燃料研究进展[J]. 化工进展, 2019, 38 (3): 119- 128. |
23 |
施翔星, 宋洪川, 黄瑛, 等. 大型石化公司发展加氢生物燃料的现状及对策[J]. 生物质化学工程, 2019, 53 (4): 59- 66.
doi: 10.3969/j.issn.1673-5854.2019.04.009 |
24 |
CHEN B L , YAN G H , CHEN G F , et al. Recent progress in the development of advanced biofuel 5-ethoxymethylfurfural[J]. BMC Energy, 2020, 2 (1): 1- 13.
doi: 10.1186/s42500-020-0011-8 |
25 |
朱仕林, 李静丹, 姜小祥, 等. 5-羟甲基糠醛与乙酰丙酸制备生物基化学品的研究进展[J]. 生物质化学工程, 2016, 50 (4): 53- 59.
doi: 10.3969/j.issn.1673-5854.2016.04.010 |
26 |
LANZAFAME P , TEMI D M , PERATHONER S , et al. Etherification of 5-hydroxymethyl-2-furfural(HMF) with ethanol to biodiesel components using mesoporous solid acidic catalysts[J]. Catalysis Today, 2011, 175 (1): 435- 441.
doi: 10.1016/j.cattod.2011.05.008 |
27 |
LANZAFAME P , BARBERA K , PERATHONER S , et al. The role of acid sites induced by defects in the etherification of HMF on Silicalite-1 catalysts[J]. Journal of Catalysis, 2015, 330, 558- 568.
doi: 10.1016/j.jcat.2015.07.028 |
28 |
NEVES P , ANTUNES M M , RUSSO P A , et al. Production of biomass-derived furanic ethers and levulinate esters using heterogeneous acid catalysts[J]. Green Chemistry, 2013, 15, 3367- 3376.
doi: 10.1039/c3gc41908h |
29 |
BALAKRISHNAN M , SACIA E R , BELL A T . Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2, 5-bis(alkoxymethyl)furans as potential bio-diesel candidates[J]. Green Chemistry, 2012, 14 (6): 1626- 1634.
doi: 10.1039/c2gc35102a |
30 |
LIU A Q , LIU B , WANG Y M , et al. Efficient one-pot synthesis of 5-ethoxymethylfurfural from fructose catalyzed by heteropolyacid supported on K-10 clay[J]. Fuel, 2014, 117, 68- 73.
doi: 10.1016/j.fuel.2013.09.072 |
31 |
CHE P H , LU F , ZHANG J J , et al. Catalytic selective etherification of hydroxyl groups in 5-hydroxymethylfurfural over H4SiW12O40/MCM-41 nanospheres for liquid fuel production[J]. Bioresource Technology, 2012, 119, 433- 436.
doi: 10.1016/j.biortech.2012.06.001 |
32 | LIU B , ZHANG Z H , DENG K J . Efficient One-pot synthesis of 5-(ethoxymethyl)furfural from fructose catalyzed by a novel solid catalyst[J]. Industrial & Engineering Chemistry Research, 2012, 51 (47): 15331- 15336. |
33 |
LIU B , ZHANG Z H , HUANG K C . Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the synthesis of 5-hydroxymethylfurfural and 5-ethoxymethylfurfural from fructose[J]. Cellulose, 2013, 20 (4): 2081- 2089.
doi: 10.1007/s10570-013-9944-0 |
34 |
LIU B , ZHANG Z H . One-pot conversion of carbohydrates into 5-ethoxymethylfurfural and ethyl D-glucopyranoside in ethanol catalyzed by a silica supported sulfonic acid catalyst[J]. RSC Advances, 2013, 3 (30): 12313- 12319.
doi: 10.1039/c3ra41043a |
35 |
YUAN Z L , ZHANG Z H , ZHENG J D , et al. Efficient synthesis of promising liquid fuels 5-ethoxymethylfurfural from carbohydrates[J]. Fuel, 2015, 150, 236- 242.
doi: 10.1016/j.fuel.2015.02.020 |
36 |
LIU B , ZHANG Z H , HUANG K C , et al. Efficient conversion of carbohydrates into 5-ethoxymethylfurfural in ethanol catalyzed by AlCl3[J]. Fuel, 2013, 113, 625- 631.
doi: 10.1016/j.fuel.2013.06.015 |
37 |
LANZAFAME P , PAPANIKOLAOU G , BARBERA K , et al. Etherification of HMF to biodiesel additives: The role of NH4+ confinement in Beta zeolites[J]. Journal of Energy Chemistry, 2019, 36, 114- 121.
doi: 10.1016/j.jechem.2019.07.009 |
38 |
CLIMENT M J , CORMA A , IBORRA S , et al. Mesoporous materials as catalysts for the production of chemicals: Synthesis of alkyl glucosides on MCM-41[J]. Journal of Catalysis, 1999, 183 (1): 76- 82.
doi: 10.1006/jcat.1998.2382 |
39 | LANZAFAME P , PAPANIKOLAOU G , PERATHONER S , et al. Direct versus acetalization routes in the reaction network of catalytic HMF etherification[J]. Catalysis Science & Technology, 2018, 8 (5): 1304- 1313. |
40 |
DOUSTKHAH E , LIN J , ROSTAMNIA S , et al. Development of sulfonic-acid-functionalized mesoporous materials: Synthesis and catalytic applications[J]. Chemistry-A European Journal, 2019, 25 (7): 1614- 1635.
doi: 10.1002/chem.201802183 |
41 |
WANG H L , DENG T S , WANG Y X , et al. Graphene oxide as a facile acid catalyst for the one-pot conversion of carbohydrates into 5-ethoxymethylfurfural[J]. Green Chemistry, 2013, 15 (9): 2379- 2383.
doi: 10.1039/c3gc41109e |
42 |
ANTUNES M M , RUSSO P A , WIPER P V , et al. Sulfonated graphene oxide as effective catalyst for conversion of 5-(hydroxymethyl)-2-furfural into biofuels[J]. ChemSusChem, 2014, 7 (3): 804- 812.
doi: 10.1002/cssc.201301149 |
43 |
ALAM M I , DE S , DUTTA S , et al. Solid-acid and ionic-liquid catalyzed one-pot transformation of biorenewable substrates into a platform chemical and a promising biofuel[J]. RSC Advances, 2012, 2 (17): 6890- 6896.
doi: 10.1039/c2ra20574b |
44 |
MASCAL M . 5-(Chloromethyl) furfural is the new HMF: Functionally equivalent but more practical in terms of its production from biomass[J]. ChemSusChem, 2015, 8 (20): 3391- 3395.
doi: 10.1002/cssc.201500940 |
45 | CHUNDURY D , SZMANT H H . Preparation of polymeric building blocks from 5-hydroxymethyl and 5-chloromethylfurfuraldehyde[J]. Industrial & Engineering Chemistry Product Research and Development, 1981, 20 (1): 158- 163. |
46 |
MASCAL M , DUTTA S . Synthesis of the natural herbicide δ-aminolevulinic acid from cellulose-derived 5-(chloromethyl) furfural[J]. Green Chemistry, 2011, 13 (1): 40- 41.
doi: 10.1039/C0GC00548G |
47 |
MASCAL M , NIKITIN E B . Comment on processes for the direct conversion of cellulose or cellulosic biomass into levulinate esters[J]. ChemSusChem, 2010, 3 (12): 1349- 1351.
doi: 10.1002/cssc.201000326 |
48 | MASCAL M , NIKITIN E B . High-yield conversion of plant biomass into the key value-added feedstocks 5-(hydroxymethyl)furfural, levulinic acid, and levulinic esters via 5-(chloromethyl)furfural[J]. Green Chemistry, 2010, 10, 370- 373. |
49 | MASCAL M , NIKITIN E B . Co-processing of carbohydrates and lipids in oil crops to produce a hybrid biodiesel[J]. Energy & Fuels, 2010, 24 (3): 2170- 2171. |
50 |
MASCAL M , NIKITIN E B . Dramatic advancements in the saccharide to 5-(chloromethyl)furfural conversion reaction[J]. ChemSusChem, 2009, 2 (9): 859- 861.
doi: 10.1002/cssc.200900136 |
51 | MASCAL M , NIKITIN E B . Towards the efficient, total glycan utilization of biomass[J]. ChemSusChem, 2009, 2 (6): 423- 426. |
52 |
BREDIHHIN A , MAEORG U , VARES L . Evaluation of carbohydrates and lignocellulosic biomass from different wood species as raw material for the synthesis of 5-bromomethyfurfural[J]. Carbohydrate Research, 2013, 375, 63- 67.
doi: 10.1016/j.carres.2013.04.002 |
53 |
VIIL I , BREDIHHIN A , MAEORG U , et al. Preparation of potential biofuel 5-ethoxymethylfurfural and other 5-alkoxymethylfurfurals in the presence of oil shale ash[J]. RSC Advances, 2014, 4 (11): 5689- 5693.
doi: 10.1039/c3ra46570e |
54 |
宋姣, 杨波. 生物质颗粒燃料燃烧特性及其污染物排放情况综述[J]. 生物质化学工程, 2016, 50 (4): 60- 64.
doi: 10.3969/j.issn.1673-5854.2016.04.011 |
55 |
CAO Q , LIANG W Y , GUAN J , et al. Catalytic synthesis of 2, 5-bis-methoxymethylfuran: A promising cetane number improver for diesel[J]. Applied Catalysis A: General, 2014, 481, 49- 53.
doi: 10.1016/j.apcata.2014.05.003 |
56 | TARABANKO V E , SMIRNOVA M A , CHERNYAK M Y . Investigation of acid-catalytic conversion of carbohydrates in the presence of aliphatic alcohols at mild temperatures[J]. Chemistry for Sustainable Development, 2005, 13, 551- 558. |
57 |
LAI L K , ZHANG Y G . The production of 5-hydroxymethylfurfural from fructose in isopropyl alcohol: A green and efficient system[J]. ChemSusChem, 2011, 4 (12): 1745- 1748.
doi: 10.1002/cssc.201100489 |
58 | LIU A Q , ZHANG Z H , FANG Z F , et al. Synthesis of 5-ethoxymethylfurfural from 5-hydroxymethylfurfural and fructose in ethanol catalyzed by MCM-41 supported phosphotungstic acid[J]. Journal of Industrial & Engineering Chemistry, 2014, 20 (4): 1977- 1984. |
59 |
GUPTA D , SAHA B . Dual acidic titania carbocatalyst for cascade reaction of sugar to etherified fuel additives[J]. Catalysis Communications, 2018, 110, 46- 50.
doi: 10.1016/j.catcom.2018.02.026 |
60 |
WANG H L , DENG T S , WANG Y X , et al. Efficient catalytic system for the conversion of fructose into 5-ethoxymethylfurfural[J]. Bioresource Technology, 2013, 136, 394- 400.
doi: 10.1016/j.biortech.2013.02.110 |
61 |
JIA X Q , MA J P , CHE P H , et al. Direct conversion of fructose-based carbohydrates to 5-ethoxymethylfurfural catalyzed by AlCl3·6H2O/BF3·(Et)2O in ethanol[J]. Journal of Energy Chemistry, 2013, 22 (1): 93- 97.
doi: 10.1016/S2095-4956(13)60012-1 |
62 |
YANG Y , HU C W , ABU-OMAR M M . Conversion of glucose into furans in the presence of AlCl3 in an ethanol-water solvent system[J]. Bioresource Technology, 2012, 116, 302- 306.
doi: 10.1016/j.biortech.2012.03.081 |
63 | LIU J T , TANG Y , FU X . Efficient conversion of carbohydratesto ethoxymethylfurfural and levulinic acid ethyl ester under the catalysis of recyclable DMSO/Brønsted acids[J]. Starch-Starke, 2015, 67 (9/10): 765- 771. |
64 | LEW C M , RAJABBEIGI N , TSAPATSIS M . One-pot synthesis of 5-(ethoxymethyl)furfural from glucose using Sn-BEA and Amberlyst catalysts[J]. Industrial & Engineering Chemistry Research, 2012, 51 (14): 5364- 5366. |
65 |
LI H , SARAVANAMURUGAN S , YANG S , et al. Direct transformation of carbohydrates to the biofuel 5-ethoxymethylfurfural by solid acid catalysts[J]. Green Chemistry, 2016, 18, 726- 734.
doi: 10.1039/C5GC01043H |
66 |
高子翔, 张胜南, 易维明. 纤维素典型热解产物生成机理研究进展[J]. 生物质化学工程, 2019, 53 (5): 57- 66.
doi: 10.3969/j.issn.1673-5854.2019.05.010 |
67 |
GARVES K . Acid catalyzed degradation of cellulose in alcohols[J]. Journal of Wood Chemistry and Technology, 1988, 8 (1): 121- 134.
doi: 10.1080/02773818808070674 |
68 |
ZHU H , CAO Q , LI C H , et al. Acidic resin-catalysed conversion of fructose into furan derivatives in low boiling point solvents[J]. Carbohydrate Research, 2011, 346 (13): 2016- 2018.
doi: 10.1016/j.carres.2011.05.026 |
69 |
KRAUS G A , GUNEY T . A direct synthesis of 5-alkoxymethylfurfural ethers from fructose via sulfonic acid-functionalized ionic liquids[J]. Green Chemistry, 2012, 14, 1593- 1596.
doi: 10.1039/c2gc35175g |
70 |
BICKER M , KAISER D , OTT L , et al. Dehydration of D-fructose to hydroxymethylfurfural in sub- and supercritical fluids[J]. Journal of supercritical fluids, 2005, 36 (2): 118- 126.
doi: 10.1016/j.supflu.2005.04.004 |
71 |
DING D Q , XI J X , WANG J J , et al. Production of methyl levulinate from cellulose: Selectivity and mechanism study[J]. Green Chemistry, 2015, 17 (7): 4037- 4044.
doi: 10.1039/C5GC00440C |
72 |
SARIN R , KUMAR R , SRIVASTAV B , et al. Biodiesel surrogates: Achieving performance demands[J]. Bioresource Technology, 2009, 100 (12): 3022- 3028.
doi: 10.1016/j.biortech.2009.01.032 |
73 | GUPTA M , KUMAR N . Scope and opportunities of using glycerol as an energy source[J]. Renewable & Sustainable Energy Reviews, 2012, 16 (7): 4551- 4556. |
74 |
SHINDE S , RODE C V . Cascade reductive etherification of bioderived aldehydes over Zr-based catalysts[J]. ChemSusChem, 2017, 10 (20): 4090- 4101.
doi: 10.1002/cssc.201701275 |
75 | LUO J , YU J Y , GORTE R J , et al. The effect of oxide acidity on HMF etherification[J]. Catalysis Science & Technology, 2014, 4 (9): 3074- 3081. |
76 | YANG F F , ZHANG S G , ZHANG Z C , et al. A biodiesel additive: Etherification of 5-hydroxymethylfurfural with isobutene to tert-butoxymethylfurfural[J]. Catalysis Science & Technology, 2015, 5, 4602- 4612. |
77 | SALMINEN E , KUMAR N , VIRTANEN P , et al. Etherification of 5-hydroxymethylfurfural to a biodiesel component over ionic liquid modified zeolites[J]. Topics in Catalysis, 2013, 56 (9/10): 765- 769. |
78 |
ARIAS K S , CLIMENT M J , CORMA A , et al. Biomass-derived chemicals: Synthesis of biodegradable surfactant ether molecules from hydroxymethylfurfural[J]. ChemSusChem, 2014, 7 (1): 210- 220.
doi: 10.1002/cssc.201300531 |
79 | RAS E J , MAISULS S , HAESAKKERS P , et al. Selective hydrogenation of 5-ethoxymethylfurfural over alumina-supported heterogeneous catalysts[J]. Advanced Synthesis & Catalysis, 2009, 351 (18): 3175- 3185. |
80 |
HU H L , HU D X , JIN H T , et al. Efficient production of furanic diether in a continuous fixed bed reactor[J]. ChemCatChem, 2019, 11 (8): 2179- 2186.
doi: 10.1002/cctc.201900054 |
81 | JONG E D , VIJLBRIEF T , HIJKOOP R , et al. Promising results with YXY Diesel components in an ESC test cycle using a PACCAR Diesel engine[J]. Biomass & Bioenergy, 2012, 36, 151- 159. |
82 |
REN Y , HUANG Z , MIAO H , et al. Combustion and emissions of a DI diesel engine fuelled with diesel-oxygenate blends[J]. Fuel, 2008, 87 (12): 2691- 2697.
doi: 10.1016/j.fuel.2008.02.017 |
83 |
FANG W T , HU H L , DONG P , et al. Improvement of furanic diether selectivity by adjusting Brønsted and Lewis acidity[J]. Applied Catalysis A: General, 2018, 565, 146- 151.
doi: 10.1016/j.apcata.2018.07.013 |
84 |
LI X L , ZHANG K , CHEN S Y , et al. A cobalt catalyst for reductive etherification of 5-hydroxymethyl-furfural to 2, 5-bis(methoxymethyl)furan under mild conditions[J]. Green Chemistry, 2018, 20, 1095- 1105.
doi: 10.1039/C7GC03072J |
85 |
杨延军, 李兴龙, 傅尧, 等. Cu-Co催化剂选择性加氢醚化HMF制备2, 5-二(甲氧基甲基)呋喃[J]. 中国科学技术大学学报, 2019, 49 (6): 445- 451.
doi: 10.3969/j.issn.0253-2778.2019.06.003 |
86 | MUSOLINO M , GINES-MOLINA M J , MORENO-TOST R , et al. Purolite-catalyzed etherification of 2, 5-bis (hydroxymethyl) furan: A systematic study[J]. ACS Sustainable Chemistry & Engineering, 2019, 7 (12): 10221- 10226. |
87 |
HAN J , KIM Y H , JUNG B Y , et al. Highly selective catalytic hydrogenation and etherification of 5-hydroxymethyl-2-furaldehyde to 2, 5-bis (alkoxymethyl) furans for potential biodiesel production[J]. Synlett, 2017, 28 (17): 2299- 2302.
doi: 10.1055/s-0036-1589076 |
88 |
JAE J , MAHMOUD E , LOBO R F , et al. Cascade of liquid-phase catalytic transfer hydrogenation and etherification of 5-hydroxymethylfurfural to potential biodiesel components over Lewis acid zeolites[J]. ChemCatChem, 2014, 6 (2): 508- 513.
doi: 10.1002/cctc.201300978 |
89 |
WEI J N , WANG T , LIU H , et al. Assembly of Zr-based coordination polymer over USY zeolite as a highly efficient and robust acid catalyst for one-pot transformation of fructose into 2, 5-bis (isopropoxymethyl) furan[J]. Journal of Catalysis, 2020, 389, 87- 98.
doi: 10.1016/j.jcat.2020.05.020 |
90 | MOREAU C , BELGACEM M N , GANDINI A . Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers[J]. Topics in Catalysis, 2004, 27 (1/2/3/4): 11- 30. |
91 | CLIMENT M J , CORMA A , IBORRA S . Converting carbohydrates to bulk chemicals and fine chemicals over heterogeneous catalysts[J]. ChemInform, 2011, 13 (3): 520- 540. |
92 | HU L , LIN L , WU Z , et al. Recent advances in catalytic transformation of biomass-derived 5-hydroxymethylfurfural into the innovative fuels and chemicals[J]. Renewable & Sustainable Energy Reviews, 2017, 74, 230- 257. |
93 |
MLIKI K , TRABELSI M . Chemicals from biomass: Efficient and facile synthesis of 5, 5'(oxy-bis(methylene))bis-2-furfural from 5-hydroxymethylfurfural[J]. Industrial Crops and Products, 2015, 78, 91- 94.
doi: 10.1016/j.indcrop.2015.10.026 |
94 |
WANG H L , WANG Y X , DENG T S , et al. Carbocatalyst in biorefinery: Selective etherification of 5-hydroxymethylfurfural to 5, 5'(oxy-bis(methylene)bis-2-furfural over graphene oxide[J]. Catalysis Communications, 2015, 59, 127- 130.
doi: 10.1016/j.catcom.2014.10.009 |
95 |
SHINDE S , RODE C . Selective self-etherification of 5-(hydroxymethyl)furfural over Sn-Mont catalyst[J]. Catalysis Communications, 2017, 88, 77- 80.
doi: 10.1016/j.catcom.2016.09.034 |
96 |
STANEV N , BORDADO J C M , AFONSO C A M , et al. Solvent-free catalytic self-etherification of 5-hydroxymethyl furfural[J]. ChemCatChem, 2018, 10 (23): 5406- 5409.
doi: 10.1002/cctc.201801560 |
[1] | Ling XIE, Xuejun ZHANG, Chun JI, Yangjie HE, Han TAO. Current Situation in Extraction and Large-scale Production of Eucommia ulmoides Gum and Its Development Issues [J]. Biomass Chemical Engineering, 2021, 55(4): 34-42. |
[2] | Zhichao LIU, Yanyan WANG, Fangdong ZHENG, Di WAN. Fast Pyrolysis Experiments of Corn Stalk by Py-GC/MS [J]. Biomass Chemical Engineering, 2021, 55(4): 29-33. |
[3] | Qilin ZHU, Ming CAO, Xuebin ZHANG, Kai TAO, Yongchun KE, Lei MENG. Physicochemical and Infrared Spectroscopic Properties of Gramineae Plants Biochar at Different Pyrolysis Temperatures [J]. Biomass Chemical Engineering, 2021, 55(4): 21-28. |
[4] | Hongye ZHAO, Yi WU, Zhengjiang DU, Quansheng LIU, Huacong ZHOU. Preparation and Hydrogenation Performance of Cobalt-orange Peel Carbon Hydrogen Transfer Catalyst [J]. Biomass Chemical Engineering, 2021, 55(4): 14-20. |
[5] | Xinchun JIANG, Jingshen OU, Fan LI, Hongcai ZHOU, Yi TONG, Xinshu ZHUANG. Low-energy Consumption Technology for Industrial Production of Corn Fuel Ethanol [J]. Biomass Chemical Engineering, 2021, 55(4): 7-13. |
[6] | Donghua JI, Hongyan LI, Zhendong LEI, Gaojian MIAO, Ming ZHAO, Zhihe WANG. Pyrolysis Characteristics and Pyrolysis Products of Sunflower Stem [J]. Biomass Chemical Engineering, 2021, 55(4): 1-6. |
[7] | XU Ruting, WANG Ao, SUN Kang. Research Progress in Absorption Regeneration of Waste Lubricant [J]. Biomass Chemical Engineering, 2021, 55(4): 59-65. |
[8] | WANG Xiaolu, YAO Xuefeng, CHEN Yuxin, ZHOU Huacong, LIU Quansheng. Research Progress on Zirconium/Hafnium Based Hydrogen Transfer Catalyst [J]. Biomass Chemical Engineering, 2021, 55(4): 66-76. |
[9] | HE Dongyang, LIANG Guowei, LI Xinyang, WU Shuangyi, NIU Miaomiao. Research Review on Cracking and Removal of Tar Catalyzed by Biomass Coke [J]. Biomass Chemical Engineering, 2021, 55(4): 77-84. |
[10] | Jing YANG, Jianchun JIANG, Ning ZHANG, Hao XU, Jingcong XIE, Jian ZHAO. Research Progress on Lignin Degradation by Microorganism [J]. Biomass Chemical Engineering, 2021, 55(3): 62-70. |
[11] | Ruifan LI, Yubao CHEN, Yongyan ZHAO, Shiyun ZHUANG, Wenjie ZHANG. Response Surface Optimization of Preparation of Aviation Kerosene from Jatropha Oil Catalyzed by Pd-Al2O3-BEA [J]. Biomass Chemical Engineering, 2021, 55(3): 55-61. |
[12] | Shaohua LIANG, Taiyan ZHANG, Yongling YAO, Chengbin LU, Bin XU, Miaomiao NIU. Simulation Study of Biomass Two-stage Enriched Air Gasification-Gas Turbine Combustion for Power Generation [J]. Biomass Chemical Engineering, 2021, 55(3): 47-54. |
[13] | Changling ZHU, Peng LEI, Fenglun ZHANG, Huanshi ZHANG. Debranching Modification of Pullulanase of Gleditsia sinensis Polysaccharide [J]. Biomass Chemical Engineering, 2021, 55(3): 42-46. |
[14] | Jingtao DAI, Ying YANG, Lina WANG. Effect of CaCl2on Physicochemical Properties of Cotton Straw Carbon [J]. Biomass Chemical Engineering, 2021, 55(3): 35-41. |
[15] | Song KU, Xuesong TAN, Rundong LI, Xinshu ZHUANG, Zhenhong YUAN. Preparation of Furfural and Levulinic Acid from Hybrid Pennisetum Hydrolysis in Biphasic Hydrated Molten Salt System [J]. Biomass Chemical Engineering, 2021, 55(3): 29-34. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||