Research progress of chemical catalysis for biomass-based furfural to nitrogen-containing compounds

CHEN Jiayue; LI Keming; HUANG Yaobing; LU Qiang

doi:10.19906/j.cnki.JFCT.2024007

Article Contents

Article Navigation > Journal of Fuel Chemistry and Technology > 2024 > Uncorrected proof

CHEN Jiayue, LI Keming, HUANG Yaobing, LU Qiang. Research progress of chemical catalysis for biomass-based furfural to nitrogen-containing compounds[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2024007

Citation:

CHEN Jiayue, LI Keming, HUANG Yaobing, LU Qiang. Research progress of chemical catalysis for biomass-based furfural to nitrogen-containing compounds[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2024007

Citation:

PDF( 881 KB)

Research progress of chemical catalysis for biomass-based furfural to nitrogen-containing compounds

doi: 10.19906/j.cnki.JFCT.2024007

National Engineering Research Center of New Energy Power Generation, School of New Energy, North China Electric Power University, Beijing 102206, China

Funds: The project was supported by National Natural Science Foundation of China (52276189, 51821004).

Received Date: 2024-01-18
Accepted Date: 2024-03-06
Rev Recd Date: 2024-03-03

Available Online: 2024-04-02

Abstract

Abstract

The utilization of biomass holds a great promise to partially replace the non-renewable fossil resources for the production of chemicals and materials for daily use, which could effectively mitigate the challenges associated with global resource scarcity. Furfural, a prominent biomass-derived platform compound derived from the dehydration of xylose in hemicellulose, which is widely used as the key intermediate or solvent in the petrochemicals, coating, pesticides, medicine, synthetic rubber, etc. At the same time, furfural can be converted into a series of high value-added chemicals and fuel, such as alcohols, acids, esters, nitriles, amines, and others due to its active C=O bonds and furan rings. Typical chemical reactions, such as reduction, oxidation, etherification, ammonia oxidation, reduction amination, ring rearrangements and others, are frequently used for the above conversions. Among various chemicals obtained from furfural conversions, nitrogen-containing compounds have attracted considerable attention, owing to the wide applications of such type molecules in the synthesis of drug molecules, bioplastics, and other functional materials. Therefore, using furfural as a raw material to synthesize bio-based nitrogenous compounds represents a cutting-edge research direction. In the presence of nitrogen sources, furfural can be transformed into diverse nitrogen-containing compounds through different reactions, such as reduction amination, ammonia oxidation, oxidative coupling, etc. Varied nitrogen sources (e.g. NH₃, N₂H₄·H₂O, NH₄HCO₂, CH₃COONH₄, (NH₄)₂CO₃ and others), catalysts, reaction atmospheres, and temperatures can result in distinct target products during furfural conversions. Currently, domestic and foreign research groups have made significant progress on furfural conversions to different nitrogen-containing compounds. Therefore, this review aims to briefly outline the recent achievements in the synthesis of high-value nitrogen-containing compounds from furfural through catalytic conversions over different catalysts. The main content includes: (1) synthesizing amines by reduction aminations, e.g. primary, secondary, and tertiary amines; (2) nitriles production by ammonia oxidation; (3) producing amides by amidation; (4) preparing heterocyclic compounds, such as benzoheterocyclic, thiazole, pyrrole, indole, piperidine and pyridine via oxidative cyclization, decarbonylation-amination, reduction amination, hydrogenation, ring rearrangements. The influences of synthesis methods, catalyst types, reaction pathways, mechanisms, as well as the nitrogen sources, on product distributions were discussed in detail. Considering the pathways and products potentially affected by different nitrogen sources and reaction conditions, future breakthroughs in the synthesis of nitrogen-containing compounds from furfural can be anticipated from the following aspects: (1) By systematically considering the reaction processes and mechanisms, the construction of composite catalysts and precise adjustment of reaction conditions to integrate multiple reaction steps into one is a trend in this research area to attain more efficient and green conversion processes; (2) Combined experimental with theoretical investigations to comprehensively reveal the reaction pathways during the reaction of different nitrogen sources with furfural; (3) Exploration of new chemical conversion routes and catalysts for the production of more novel nitrogen-containing compounds, to further broaden the application areas of furfural based chemicals. In brief, this review provides a systematical review on the production of furfural based nitrogen-containing chemicals, which would benefit the communities working in biomass utilization areas, and also contribute to the establishment of knowledge of the furfural chemical family.
- furfural,
- chemical catalysis,
- nitrogen sources,
- nitrogen-containing chemicals

FullText(HTML)

References(37)

References

[1]	李缔, 李攀, 王贤华, 等. 基于Fe负载的HZSM-5催化热解制备生物油实验研究[J]. 燃料化学学报,2016,44(5):540−547. LI Di, LI Pan, WANG Xianhua, et al. Experimental study on bio-oil from catalytic pyrolysis on Fe modified HZSM-5[J]. J Fuel Chem Technol,2016,44(5):540−547.
[2]	魏珺楠, 唐兴, 孙勇, 等. 新型生物质基平台分子γ-戊内酯的应用[J]. 化学进展,2016,28(11):1672−1681. WEI Junnan, TANG Xing, SUN Yong, et al. Applications of novel biomass-derived platform molecule γ-valerolactone[J]. Chem Ind Eng Prog,2016,28(11):1672−1681.
[3]	海雪清, 谭静静, 何静, 等. CuCo双金属催化剂催化糠醛加氢制备1, 5-戊二醇的研究[J]. 燃料化学学报,2023,51(7):959−969. doi: 10.1016/S1872-5813(23)60334-2 HAI Xueqing, TAN Jinging, HE Jing, et al. Hydrogenation of furfural to 1, 5-pentanediol over CuCo bimetallic catalysts[J]. J Fuel Chem Technol,2023,51(7):959−969. doi: 10.1016/S1872-5813(23)60334-2
[4]	李微, 贡红辉, 史显磊. 催化转移氢化制生物质基2, 5-呋喃二甲醇研究进展[J]. 燃料化学学报,2023,52(x):1−21. LI Wei, GONG Honghui, SHI Xianlei. Recent advances in preparing biomass-based 2, 5-bis(hydroxymethyl)furan by catalytic transfer hydrogenation[J]. J Fuel Chem Technol,2023,52(x):1−21.
[5]	林鹿, 何北海, 孙润仓, 等. 木质生物质转化高附加值化学品[J]. 化学进展,2007,19(7/8):1206−1216. LIN Lu, HE Beihai, SUN Runcang, et al. High-value chemicals from lignocellulosic biomass[J]. Chem Ind Eng Prog,2007,19(7/8):1206−1216.
[6]	韩冬, 孙来芝, 陈雷, 等. 生物质与塑料共催化热解制备芳烃化合物研究进展[J]. 燃料化学学报,2023,52(x):1−15. HAN Dong, SUN Laizhi1, CHEN Lei, et al. Review on the progress in the production of aromatic hydrocarbons by Co-catalytic pyrolysis of biomass and plastics[J]. J Fuel Chem Technol,2023,52(x):1−15.
[7]	张军, 李丹妮, 袁浩然, 等. 生物质基糠醛和5-羟甲基糠醛加氢转化研究进展[J]. 燃料化学学报,2021,49(12):1752−1767. doi: 10.1016/S1872-5813(21)60135-4 ZHANG Jun, LI Danni, YUAN Haoran, et al. Advances on the catalytic hydrogenation of biomass-derived furfural and 5- hydroxymethylfurfural[J]. J Fuel Chem Technol,2021,49(12):1752−1767. doi: 10.1016/S1872-5813(21)60135-4
[8]	LI K M, ZHANG Q, XU Z M, et al. Tunable mono- and di-methylation of amines with methanol over bimetallic CuCo nanoparticle catalysts. Green Chem, 2022, 24(15): 5965-5977.
[9]	CHEN J Y, HUANG Y B, HU B, et al. A bio-based click reaction leading to the dihydropyridazinone platform for nitrogen-containing scaffolds. Green Chem, 2023, 25(7): 2672-2680.
[10]	LI H, GUO H X, Fang Z, et al. Cycloamination strategies for renewable N-heterocycles[J]. Green Chem,2020,22(3):582−611. doi: 10.1039/C9GC03655E
[11]	HULSEY M J, YANG H Y, YAN N. Sustainable routes for the synthesis of renewable heteroatom-containing chemicals[J]. ACS Sustain Chem Eng,2018,6(5):5694−5707. doi: 10.1021/acssuschemeng.8b00612
[12]	代金杭, 蔡雅洁. 由甲壳素生物质合成含氮化学品研究进展[J]. 化学研究与应用,2020,32(7):1111−1116. doi: 10.3969/j.issn.1004-1656.2020.07.002 DAI Jinhang, CAI Yajie. Research progressof nitrogen-containing chemicals production employing chitin biomass as substrate[J]. Chemical research and application,2020,32(7):1111−1116. doi: 10.3969/j.issn.1004-1656.2020.07.002
[13]	苏文韬, 李昌志. 木质素制备含氮杂环芳香化合物研究进展[J]. 湖南师范大学自然科学学报,2023,46(4):1−13. SU Wentao, LI Changzhi. Progress on the production of nitrogen-containing heterocyclic aromatic compounds from lignin[J]. Journal of Natural Science of Hunan Normal University,2023,46(4):1−13.
[14]	ZHANG X, XU S Q, LI Q F, et al. Recent advances in the conversion of furfural into bio-chemicals through chemo- and bio-catalysis[J]. RSC Adv,2021,11(43):27042−27058. doi: 10.1039/D1RA04633K
[15]	谭静静, 苏以豪, 高宽, 等. 糠醛及其衍生物选择性加氢制备戊二醇的研究进展[J]. 燃料化学学报,2021,49(6):780−790. doi: 10.1016/S1872-5813(21)60036-1 TAN Jingjing, SU Yihao, GAO Kuan, et al. Recent advances in the selective hydrogenation of furfural and its derivatives to pentanediol[J]. J Fuel Chem Technol,2021,49(6):780−790. doi: 10.1016/S1872-5813(21)60036-1
[16]	QI H F, YANG J, LIU F, et al. Highly selective and robust single-atom catalyst Ru₁/NC for reductive amination of aldehydes/ketones[J]. Nat Commun,2021,12(1):3295. doi: 10.1038/s41467-021-23429-w
[17]	GAO Z X, CAI L Y, MA H R, et al. Dual scale hydrogen transfer bridge construction for biomass tandem reductive amination[J]. ACS Catal,2023,13(19):12835−12847. doi: 10.1021/acscatal.3c03486
[18]	CHATTERJEE M, ISHIZAKA T, KAWANAMI H. Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: an environmentally friendly approach[J]. Green Chem,2016,18(2):487−496. doi: 10.1039/C5GC01352F
[19]	SONG W J, WAN Y J, LI Y F, et al. Electronic Ni–N interaction enhanced reductive amination on an N-doped porous carbon supported Ni catalyst[J]. Catal Sci Technol,2022,12(23):7208−7218. doi: 10.1039/D2CY01551J
[20]	ZOU H T, CHEN J Z. Efficient and selective approach to biomass-based amine by reductive amination of furfural using Ru catalyst[J]. Appl Catal B:Environ,2022,309:121262. doi: 10.1016/j.apcatb.2022.121262
[21]	JIANG S, RAMDANI W, MULLER E, et al. Direct catalytic conversion of furfural to furan-derived amines in the presence of Ru-based catalyst[J]. ChemSusChem,2020,13(7):1699−1704. doi: 10.1002/cssc.202000003
[22]	JIANG S, MA C R, MULLER E, et al. Selective synthesis of THF-derived amines from biomass-derived carbonyl compounds[J]. ACS Catal,2019,9(10):8893−8902. doi: 10.1021/acscatal.9b03413
[23]	LIN C C, ZHOU J M, ZHENG Z F, et al. An efficient approach to biomass-based tertiary amines by direct and consecutive reductive amination of furfural[J]. J Catal,2022,410:164−179. doi: 10.1016/j.jcat.2022.04.016
[24]	DAS A K, NANDY S, BHAR S. Cu(OAc)₂ catalysed aerobic oxidation of aldehydes to nitriles under ligand-free conditions[J]. RSC Adv,2022,12(8):4605−4614. doi: 10.1039/D1RA07701E
[25]	CHEN H, SUN S J, XI H Y, et al. Catalytic oxidative conversion of aldehydes into nitriles using NH₃·H₂O/FeCl₂/NaI/Na₂S₂O₈: A practical approach to febuxostat[J]. Tetrahedron Lett,2019,60(21):1434−1436. doi: 10.1016/j.tetlet.2019.04.043
[26]	HUA M L, SONG J L, HUANG X, et al. Highly efficient oxidative cyanation of aldehydes to nitriles over Se, S, N- tri-doped hierarchically porous carbon nanosheets[J]. Angew Chem Int Ed Engl,2021,60(39):21479−21485. doi: 10.1002/anie.202107996
[27]	PAN L M, FU W Q, ZHANG L, et al. Highly dispersed Co species in N-doped carbon enhanced the aldehydes ammoxidation reaction activity[J]. Mol Catal,2022,518:112087. doi: 10.1016/j.mcat.2021.112087
[28]	YANG S W, CHEN J Z. Kinetic analysis of consecutive/parallel transformation of furfural to biomass-based primary amide by using a “concentration–time” integral[J]. ACS Catal,2022,13(1):113−131.
[29]	KIDWAI M, BANSAL V, SAXENA A, et al. Cu-nanoparticles: efficient catalysts for the oxidative cyclization of Schiffs’ bases[J]. Tetrahedron Lett,2006,47(46):8049−8053. doi: 10.1016/j.tetlet.2006.09.066
[30]	ZHOU Y K, LIU W, LIU Y C, et al. Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant[J]. Mol Catal,2020,492:111013. doi: 10.1016/j.mcat.2020.111013
[31]	CHARI M A, SHOBHA D, SASAKI T. Room temperature synthesis of benzimidazole derivatives using reusable cobalt hydroxide (II) and cobalt oxide (II) as efficient solid catalysts[J]. Tetrahedron Lett,2011,52(43):5575−5580. doi: 10.1016/j.tetlet.2011.08.047
[32]	LIN C C, WAN W H, WEI X T, et al. H₂ activation with Co nanoparticles encapsulated in N-doped carbon nanotubes for green synthesis of benzimidazoles[J]. ChemSusChem,2021,14(2):709−720. doi: 10.1002/cssc.202002344
[33]	TANAKA S, ASHIDA K, TATSUTA G, et al. Preparation of fluorescent materials from biomass-derived furfural and natural amino acid cysteine through cross-coupling reactions for extended π-conjugation[J]. Synlett,2015,26(11):1496−1500. doi: 10.1055/s-0034-1380460
[34]	SONG S, YUEN V F K, DI L, et al. Integrating biomass into the organonitrogen chemical supply chain: production of pyrrole and D-proline from furfural[J]. Angew Chem Int Ed Engl,2020,59(45):19846−19850. doi: 10.1002/anie.202006315
[35]	YAO Q, Xu L J, Han Z, et al. Production of indoles via thermo-catalytic conversion and ammonization of bio-derived furfural[J]. Chem Eng J,2015,280:74−81. doi: 10.1016/j.cej.2015.05.094
[36]	QI H F, LI Y R, ZHOU Z T, et al. Synthesis of piperidines and pyridine from furfural over a surface single-atom alloy Ru₁Co_NP catalyst[J]. Nat Commun,2023,14(1):6329. doi: 10.1038/s41467-023-42043-6
[37]	MULLER C, DIEHL V, LICHTENTHALER F W. Building blocks from sugars: Part. 23. : Hydrophilic 3-pyridinols from fructose and isomaltulose[J]. Tetrahedron,1998,54(36):10703−10712. doi: 10.1016/S0040-4020(98)00634-6