Citation: | HUANG Xinghua, DONG Shengfei, YANG Xiaoyiet al. Energy consumption of condensation-hydrogenation process to prepare alkanes from lignocellulose biomass[J]. Journal of Beijing University of Aeronautics and Astronautics, 2022, 48(1): 121-131. doi: 10.13700/j.bh.1001-5965.2020.0506(in Chinese) |
With the increasing maturity of technology for preparing furfural, 5-hydroxymethylfurfural, levulinic acid from lignocellulose biomass, platform compounds reuse technology has become an international hot spot. By studying the characteristics of the self-condensation and cross-condensation processes of platform compounds, as well as the feasible paths for subsequent hydrogenation to prepare synthetic jet fuel alkanes, two processes for preparing jet fuel with the full component use of lignocellulose biomass derived platform compounds were designed. Through energy consumption analysis and evaluation, the main energy consumption units and main input energy consumption materials in each process route were determined. Furfural-levulinic acid cross-condensation hydrogenation process compared with furfural self-condensation hydrogenation process and 5-hydroxymethyl furfural self-condensation hydrogenation process has obvious advantages in terms of heat consumption and hydrogen consumption. In order to realize the full-component utilization of straw, furfural-levulinic acid cross-condensation hydrogenation is combined with 5-hydroxymethylfurfural self-condensation hydrogenation process, and according to the current process technology, the jet fuel yield can reach 19.6%.
[1] |
HUBER G W, CHHEDA J N, BARRETT C J, et al. Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates[J]. Science, 2005, 308(5727): 1446-1450. doi: 10.1126/science.1111166
|
[2] |
CHHEDA J N, DUMESIC J A. An overview of dehydration, aldol-condensation and hydrogenation processes for production of liquid alkanes from biomass-derived carbohydrates[J]. Catalysis Today, 2007, 123(1-4): 59-70. doi: 10.1016/j.cattod.2006.12.006
|
[3] |
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. https://pubs.rsc.org/en/content/articlelanding/2016/ee/c5ee02666k
|
[4] |
ZANG H J, WANG K, ZHANG M C, et al. Catalytic coupling of biomass-derived aldehydes into intermediates for biofuels and materials[J]. Catalysis Science & Technology, 2018, 8(7): 1777-1798. https://pubs.rsc.org/en/content/articlelanding/2018/cy/c7cy02221b
|
[5] |
LI Z, ZHANG J J, NIELSEN M M, et al. Efficient C—C bond formation between two levulinic acid molecules to produce C10 compounds with the cooperation effect of lewis and brønsted acids[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(5): 5708-5711.
|
[6] |
LI H, RIISAGER A, SARAVANAMURUGAN S, et al. Carbon-increasing catalytic strategies for upgrading biomass into energy-intensive fuels and chemicals[J]. ACS Catalysis, 2018, 8(1): 148-187. doi: 10.1021/acscatal.7b02577
|
[7] |
SUBRAHMANYAM A V, THAYUMANAVAN S, HUBER G W. C—C bond formation reactions for biomass-derived molecules[J]. ChemSusChem, 2010, 3(10): 1158-1161. doi: 10.1002/cssc.201000136
|
[8] |
FABA L, DÍAZ E, ORDÓÑEZ S. Base-catalyzed condensation of levulinic acid: A new biorefinery upgrading approach[J]. ChemCatChem, 2016, 8(8): 1490-1494. doi: 10.1002/cctc.201600064
|
[9] |
AMARASEKARA A S, WIREDU B, GRADY T L, et al. Solid acid catalyzed aldol dimerization of levulinic acid for the preparation of C10 renewable fuel and chemical feedstocks[J]. Catalysis Communications, 2019, 124: 6-11. doi: 10.1016/j.catcom.2019.02.022
|
[10] |
NILGES P, DOS SANTOS T R, HARNISCH F, et al. Electrochemistry for biofuel generation: Electrochemical conversion of levulinic acid to octane[J]. Energy & Environmental Science, 2012, 5(1): 5231-5235. https://pubs.rsc.org/en/content/articlelanding/2012/ee/c1ee02685b
|
[11] |
HUANG Y B, YANG Z, DAI J J, et al. Production of high quality fuels from lignocellulose-derived chemicals: A convenient C—C bond formation of furfural, 5-methylfurfural and aromatic aldehyde[J]. RSC Advances, 2012, 2(30): 11211-11214. doi: 10.1039/c2ra22008c
|
[12] |
HRONEC M, FULAJTAROVÁ K. Selective transformation of furfural to cyclopentanone[J]. Catalysis Communications, 2012, 24: 100-104. doi: 10.1016/j.catcom.2012.03.020
|
[13] |
YANG Y L, DU Z T, HUANG Y Z, et al. Conversion of furfural into cyclopentanone over Ni-Cu bimetallic catalysts[J]. Green Chemistry, 2013, 15(7): 1932. doi: 10.1039/c3gc37133f
|
[14] |
YANG J F, LI N, LI G Y, et al. Synthesis of renewable high-density fuels using cyclopentanone derived from lignocellulose[J]. Chemical Communications, 2014, 50(20): 2572-2574. doi: 10.1039/c3cc46588h
|
[15] |
WEGENHART B L, YANG L N, KWAN S C, et al. From furfural to fuel: Synthesis of furoins by organocatalysis and their hydrodeoxygenation by cascade catalysis[J]. ChemSusChem, 2014, 7(9): 2742-2747. doi: 10.1002/cssc.201402056
|
[16] |
WANG T J, LI K, LIU Q Y, et al. Aviation fuel synthesis by catalytic conversion of biomass hydrolysate in aqueous phase[J]. Applied Energy, 2014, 136: 775-780. doi: 10.1016/j.apenergy.2014.06.035
|
[17] |
CORMA A, DELATORRE 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
|
[18] |
YANG W, GROCHOWSKI M R, SEN A. Selective reduction of biomass by hydriodic acid and its in situ regeneration from iodine by metal/hydrogen[J]. ChemSusChem, 2012, 5(7): 1218-1222. doi: 10.1002/cssc.201100669
|
[19] |
TAN J, WANG C G, ZHANG Q, et al. One-pot condensation of furfural and levulinates: A novel method for cassava use in synthesis of biofuel precursors[J]. Energy & Fuels, 2018, 32(6): 6807-6812.
|
[20] |
LIANG G F, WANG A Q, ZHAO X C, et al. Selective aldol condensation of biomass-derived levulinic acid and furfural in aqueous-phase over MgO and ZnO[J]. Green Chemistry, 2016, 18(11): 3430-3438. doi: 10.1039/C6GC00118A
|
[21] |
AMARASEKARA A S, SINGH T B, LARKIN E, et al. NaOH catalyzed condensation reactions between levulinic acid and biomass derived furan-aldehydes in water[J]. Industrial Crops and Products, 2015, 65: 546-549. doi: 10.1016/j.indcrop.2014.10.005
|
[22] |
张琦, 李宇萍, 陈伦刚, 等. 百吨/年规模生物质水相合成航油类烃过程的物质与能量转化[J]. 天津大学学报(自然科学与工程技术版), 2017, 50(1): 13-18. https://www.cnki.com.cn/Article/CJFDTOTAL-TJDX201701003.htm
ZHANG Q, LI Y P, CHEN L G, et al. Material and energy conversion of integrated 100 t/a-scale bio-jet fuel-range hydrocarbon production system via aqueous conversion of biomass[J]. Journal of Tianjin University (Science and Technology), 2017, 50(1): 13-18(in Chinese). https://www.cnki.com.cn/Article/CJFDTOTAL-TJDX201701003.htm
|
[23] |
LI Y P, CHEN L G, ZHANG X H, et al. Process and techno-economic analysis of bio-jet fuel-range hydrocarbon production from lignocellulosic biomass via aqueous phase deconstruction and catalytic conversion[J]. Energy Procedia, 2017, 105: 675-680. doi: 10.1016/j.egypro.2017.03.374
|
[24] |
ZHAO L W, ELECHI N, QIAN R, et al. Origin of the regioselectivity in the aldol condensation between hydroxymethylfurfural and levulinic acid: A DFT investigation[J]. The Journal of Physical Chemistry A, 2017, 121(9): 1985-1992. doi: 10.1021/acs.jpca.6b11100
|
[25] |
STEVENS J G, BOURNE R A, TWIGG M V, et al. Real-time product switching using a twin catalyst system for the hydrogenation of furfural in supercritical CO2[J]. Angewandte Chemie, 2010, 49(47): 8856-8859. doi: 10.1002/anie.201005092
|
[26] |
VAN BUIJTENEN J, LANGE J P, PRICE R J. Process for preparing a hydrocarbon or mixture of hydrocarbons: US20110173877[P]. 2011-07-21.
|
[27] |
KUMALAPUTRI A J, BOTTARI G, ERNE P M, et al. Tunable and selective conversion of 5-HMF to 2, 5-furandimethanol and 2, 5-dimethylfuran over copper-doped porous metal oxides[J]. ChemSusChem, 2014, 7(8): 2266-2275.
|
[28] |
LIU H Z, JIANG T, HAN B X, et al. Selective phenol hydrogenation to cyclohexanone over a dual supported Pd-Lewis acid catalyst[J]. Science, 2009, 326(5957): 1250-1252. doi: 10.1126/science.1179713
|
[29] |
XU G Y, GUO J H, ZHANG Y, et al. Selective hydrogenation of phenol to cyclohexanone over Pd-HAP catalyst in aqueous media[J]. ChemCatChem, 2015, 7(16): 2485-2492. doi: 10.1002/cctc.201500442
|
[30] |
LIU Q Y, ZHANG C H, SHI N, et al. Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones[J]. RSC Advances, 2018, 8(25): 13686-13696. https://pubs.rsc.org/en/content/articlepdf/2018/ra/c8ra01723a
|