Technological advances in the production of high value oxygen-containing chemicals from coal via dimethyl oxalate

ZHANG Hong-xu; LIU Guo-guo; YU Jia-feng; SUN Jian

doi:10.19906/j.cnki.JFCT.2023044

Volume 51 Issue 11

Nov. 2023

Turn off MathJax

Article Contents

Article Navigation > Journal of Fuel Chemistry and Technology > 2023 > 51(11): 1576-1592

ZHANG Hong-xu, LIU Guo-guo, YU Jia-feng, SUN Jian. Technological advances in the production of high value oxygen-containing chemicals from coal via dimethyl oxalate[J]. Journal of Fuel Chemistry and Technology, 2023, 51(11): 1576-1592. doi: 10.19906/j.cnki.JFCT.2023044

Citation:

ZHANG Hong-xu, LIU Guo-guo, YU Jia-feng, SUN Jian. Technological advances in the production of high value oxygen-containing chemicals from coal via dimethyl oxalate[J]. Journal of Fuel Chemistry and Technology, 2023, 51(11): 1576-1592. doi: 10.19906/j.cnki.JFCT.2023044

Citation:

PDF( 28763 KB)

Technological advances in the production of high value oxygen-containing chemicals from coal via dimethyl oxalate

doi: 10.19906/j.cnki.JFCT.2023044

ZHANG Hong-xu^{1, 2
,},
LIU Guo-guo^1
,,
YU Jia-feng^{2
,
,},
SUN Jian^{2
,
,}

1.
Shenyang University of Chemical Technology, Shenyang 110142, China
2.
Dalian Institute of Chemical Physics, Dalian 116023, China

Funds: The project was supported by the Natural Science Foundation of China (2022JJ12GX037)

Received Date: 2023-04-10
Accepted Date: 2023-05-16
Rev Recd Date: 2023-05-04

Available Online: 2023-05-24

Publish Date: 2023-11-13

Abstract

Abstract

Chinese energy structure is rich in coal and less in oil, and the development of efficient and clean utilization of coal resources is a key development direction in China. Coal can be used to synthesize dimethyl oxalate (DMO) after carbonylation by synthesis gas, and DMO can further be hydrogenated to obtain oxygen-containing chemicals with high added value, such as methyl glycolate (MG), ethylene glycol (EG), ethanol (EO), etc. Among them, MG can prepare degradable materials polyglycolic acid (PGA), EG can synthesize polyethylene glycol (PEG), and EO can synthesize ethyl acetate (EAC), which have wide application prospects. This paper focuses on DMO hydrogenation reactions, analyzes the research status of catalysts used in each hydrogenation process, focuses on the regulation of catalyst composition, catalytic mechanism and new catalyst preparation technology, analyzes the problems and challenges in the development of DMO hydrogenation catalysts, and points out the application bottlenecks and future development trends of hydrogenation products and downstream products.
- coal,
- dimethyl oxalate,
- selective hydrogenation,
- oxygen-containing chemicals,
- copper-based catalysts

FullText(HTML)

References(92)

References

[1]	WANG G, XU Y, REN H. Intelligent and ecological coal mining as well as clean utilization technology in China: Review and prospects[J]. Int J Min Sci Technol,2019,29(2):161−169. doi: 10.1016/j.ijmst.2018.06.005
[2]	WAGNER N J, COERTZEN M, MATJIE R H, VAN DYK J C, SUÁREZ-RUIZ I, CRELLING J C. Applied Coal Petrology[M]. America: Academic Press, 2008: 119−144.
[3]	XU J, YANG Y, LI Y-W. Recent development in converting coal to clean fuels in China[J]. Fuel,2015,152:122−130. doi: 10.1016/j.fuel.2014.11.059
[4]	BELL D A, TOWLER B F, FAN M. Coal Gasification And Its Applications[M]. English: William Andrew, 2010: 101–111.
[5]	TREMEL A, HASELSTEINER T, KUNZE C, SPLIETHOFF H. Experimental investigation of high temperature and high pressure coal gasification[J]. Appl Energy,2012,92:279−285. doi: 10.1016/j.apenergy.2011.11.009
[6]	ZHAO Y, ZHANG Y, WANG Y, ZHANG J, XU Y, WANG S, MA X. Structure evolution of mesoporous silica supported copper catalyst for dimethyl oxalate hydrogenation[J]. Appl Catal A: Gen,2017,539:59−69. doi: 10.1016/j.apcata.2017.04.001
[7]	CHEN Z, DUN Q, SHI Y, LAI D, ZHOU Y, GAO S, XU G. High quality syngas production from catalytic coal gasification using disposable Ca(OH)₂ catalyst[J]. Chem Eng J,2017,316:842−849. doi: 10.1016/j.cej.2017.02.025
[8]	LU T, MAO Y, WANG H, LIU L, LI K. Effect of pre-treatment on catalytic coal gasification characteristics of sub-bituminous coal[J]. J Energy Inst,2021,96:173−180. doi: 10.1016/j.joei.2021.03.013
[9]	HASANOĞLU A, FAKI E, SEÇER A, TÜRKER ÜZDEN Ş. Co-solvent effects on hydrothermal co-gasification of coal/biomass mixtures for hydrogen production[J]. Fuel, 2023, 331: part 1.
[10]	HONG Y C, LEE S J, SHIN D H, KIM Y J, LEE B J, CHO S Y, CHANG H S. Syngas production from gasification of brown coal in a microwave torch plasma[J]. Energy,2012,47(1):36−40. doi: 10.1016/j.energy.2012.05.008
[11]	MIDILLI A, KUCUK H, TOPAL M E, AKBULUT U, DINCER I. A comprehensive review on hydrogen production from coal gasification: Challenges and opportunities[J]. Int J Hydrogen Energy,2021,46(50):25385−25412. doi: 10.1016/j.ijhydene.2021.05.088
[12]	JIANG X Z, SU Y H, LEE B J, CHIEN S H. A study on the synthesis of diethyl oxalate over Pd/α-Al₂O₃ catalysts[J]. Appl Catal A: Gen,2001,211(1):47−51. doi: 10.1016/S0926-860X(00)00837-1
[13]	YANG L, PAN Z, WANG D, WANG S, WANG X, MA H, LIU H, WANG C, QU W, TIAN Z. Highly effective Pd/MgO/γ-Al₂O₃ catalysts for CO oxidative coupling to dimethyl oxalate: The effect of MgO coating on γ-Al₂O₃[J]. ACS Appl Mater Interfaces,2021,13(24):28064−28071. doi: 10.1021/acsami.1c04051
[14]	WANG Z Q, SUN J, XU Z N, GUO G C. CO direct esterification to dimethyl oxalate and dimethyl carbonate: the key functional motifs for catalytic selectivity[J]. Nanoscale,2020,12(39):20131−20140. doi: 10.1039/D0NR03008B
[15]	WANG C, HAN L, CHEN P, ZHAO G, LIU Y, LU Y. High-performance, low Pd-loading microfibrous-structured Al-fiber@ns-AlOOH@Pd catalyst for CO coupling to dimethyl oxalate[J]. J Catal,2016,337:145−156. doi: 10.1016/j.jcat.2016.02.008
[16]	MA X, CHI H, YUE H, ZHAO Y, XU Y, LV J, WANG S, GONG J. Hydrogenation of dimethyl oxalate to ethylene glycol over mesoporous Cu-MCM-41 catalysts[J]. AlChE J,2013,59(7):2530−2539. doi: 10.1002/aic.13998
[17]	YIN A, GUO X, DAI W-L, LI H, FAN K. Highly active and selective copper-containing HMS catalyst in the hydrogenation of dimethyl oxalate to ethylene glycol[J]. Appl Catal A: Gen,2008,349(1):91−99.
[18]	KONG X, WU Y, DING L, WANG R, CHEN J. Effect of Cu loading on the structural evolution and catalytic activity of Cu-Mg/ZnO catalysts for dimethyl oxalate hydrogenation[J]. New J Chem,2020,44(11):4486−4493. doi: 10.1039/C9NJ06085E
[19]	ROHMAN F S, SULAIMAN M S, MURAT M N, AZIZ N. Performance evaluation of adaptive based model predictive control for ethylene glycol production from dimethyl oxide hydrogenation [J]. Int J Chem React Eng, 2022, 21: 859–878.
[20]	CUI Y, WANG B, WEN C, CHEN X, DAI W-L. Investigation of activated-carbon-supported copper catalysts with unique catalytic performance in the hydrogenation of dimethyl oxalate to methyl glycolate[J]. ChemCatChem,2016,8(3):527−531. doi: 10.1002/cctc.201501055
[21]	FAN H, TAN J, ZHU Y, ZHENG H, LI Y. Efficient hydrogenation of dimethyl oxalate to methyl glycolate over highly active immobilized-ruthenium catalyst[J]. J Mol Catal A: Chem,2016,425:68−75. doi: 10.1016/j.molcata.2016.09.033
[22]	CHEN H, TAN J, CUI J, YANG X, ZHENG H, ZHU Y, LI Y. Promoting effect of boron oxide on Ag/SiO₂ catalyst for the hydrogenation of dimethyl oxalate to methyl glycolate[J]. Mol Catal,2017,433:346−353. doi: 10.1016/j.mcat.2017.02.039
[23]	YIN A, GUO X, DAI W, FAN K. High activity and selectivity of Ag/SiO₂ catalyst for hydrogenation of dimethyl oxalate[J]. Chem Commun,2010,46(24):4348−4350. doi: 10.1039/c0cc00581a
[24]	ZHENG J, LIN H, WANG Y-N, ZHENG X, DUAN X, YUAN Y. Efficient low-temperature selective hydrogenation of esters on bimetallic Au-Ag/SBA-15 catalyst[J]. J Catal,2013,297:110−118. doi: 10.1016/j.jcat.2012.09.023
[25]	OUYANG M, WANG Y, ZHANG J, ZHAO Y, WANG S, MA X. Three dimensional Ag/KCC-1 catalyst with a hierarchical fibrous framework for the hydrogenation of dimethyl oxalate[J]. RSC Adv,2016,6(16):12788−12791. doi: 10.1039/C5RA26602E
[26]	OUYANG M, WANG J, PENG B, ZHAO Y, WANG S, MA X. Effect of Ti on Ag catalyst supported on spherical fibrous silica for partial hydrogenation of dimethyl oxalate[J]. Appl Surf Sci,2019,466:592−600. doi: 10.1016/j.apsusc.2018.10.065
[27]	ZHENG J, DUAN X, LIN H, GU Z, FANG H, LI J, YUAN Y. Silver nanoparticles confined in carbon nanotubes: on the understanding of the confinement effect and promotional catalysis for the selective hydrogenation of dimethyl oxalate[J]. Nanoscale,2016,8(11):5959−5967. doi: 10.1039/C5NR08651E
[28]	HU M, YAN Y, DUAN X, YE L, ZHOU J, LIN H, YUAN Y. Effective anchoring of silver nanoparticles onto N-doped carbon with enhanced catalytic performance for the hydrogenation of dimethyl oxalate to methyl glycolate[J]. Catal Commun,2017,100:148−152. doi: 10.1016/j.catcom.2017.06.025
[29]	ZHOU J, DUAN X, YE L, ZHENG J, LI M M-J, TSANG S C E, YUAN Y. Enhanced chemoselective hydrogenation of dimethyl oxalate to methyl glycolate over bimetallic Ag-Ni/SBA-15 catalysts[J]. Appl Catal A: Gen,2015,505:344−353. doi: 10.1016/j.apcata.2015.08.022
[30]	ZHENG J, LIN H, ZHENG X, DUAN X, YUAN Y. Highly efficient mesostructured Ag/SBA-15 catalysts for the chemoselective synthesis of methyl glycolate by dimethyl oxalate hydrogenation[J]. Catal Commun,2013,40:129−133. doi: 10.1016/j.catcom.2013.06.022
[31]	ZHENG X, LIN H, ZHENG J, DUAN X, YUAN Y. Lanthanum oxide-modified Cu/SiO₂ as a high-performance catalyst for chemoselective hydrogenation of dimethyl oxalate to ethylene glycol[J]. ACS Catal,2013,3(12):2738−2749. doi: 10.1021/cs400574v
[32]	SUN J, YU J, MA Q, MENG F, WEI X, SUN Y, TSUBAKI N. Freezing copper as a noble metal-like catalyst for preliminary hydrogenation[J]. Sci Adv,2018,4(12):eaau3275. doi: 10.1126/sciadv.aau3275
[33]	WANG Y-N, DUAN X, ZHENG J, LIN H, YUAN Y, ARIGA H, TAKAKUSAGI S, ASAKURA K. Remarkable enhancement of Cu catalyst activity in hydrogenation of dimethyl oxalate to ethylene glycol using gold[J]. Catal Sci Technol,2012,2(8):1637−1639. doi: 10.1039/c2cy20154b
[34]	WANG D, ZHANG C, ZHU M, YU F, DAI B. Highly active and stable ZrO₂-SiO₂-supported Cu-catalysts for the hydrogenation of dimethyl oxalate to methyl glycolate[J]. ChemistrySelect,2017,2(17):4823−4829. doi: 10.1002/slct.201700895
[35]	KONG X, MA C, ZHANG J, SUN J, CHEN J, LIU K. Effect of leaching temperature on structure and performance of Raney Cu catalysts for hydrogenation of dimethyl oxalate[J]. Appl Catal A: Gen,2016,509:153−160. doi: 10.1016/j.apcata.2015.10.029
[36]	WEN C, CUI Y, CHEN X, ZONG B, DAI W-L. Reaction temperature controlled selective hydrogenation of dimethyl oxalate to methyl glycolate and ethylene glycol over copper-hydroxyapatite catalysts[J]. Appl Catal B: Environ,2015,162:483−493. doi: 10.1016/j.apcatb.2014.07.023
[37]	ABBAS M, ZHANG J, CHEN Z, CHEN J. Sonochemical synthesis of Zn-promoted porous MgO-supported lamellar Cu catalysts for selective hydrogenation of dimethyl oxalate to ethanol and their long-term stability[J]. New J Chem,2018,42(21):17553−17562. doi: 10.1039/C8NJ03766C
[38]	ABBAS M, CHEN Z, CHEN J. Shape- and size-controlled synthesis of Cu nanoparticles wrapped on RGO nanosheet catalyst and their outstanding stability and catalytic performance in the hydrogenation reaction of dimethyl oxalate[J]. J Mater Chem A,2018,6(39):19133−19142. doi: 10.1039/C8TA07371F
[39]	YAO D, WANG Y, LI Y, LI A, ZHEN Z, LV J, SUN F, YANG R, LUO J, JIANG Z, WANG Y, MA X. Scalable synthesis of Cu clusters for remarkable selectivity control of intermediates in consecutive hydrogenation[J]. Nat Commun,2023,14(1):1123. doi: 10.1038/s41467-023-36640-8
[40]	NORSKOV J K, BLIGAARD T, ROSSMEISL J, CHRISTENSEN C H. Towards the computational design of solid catalysts[J]. Nat Chem,2009,1(1):37−46. doi: 10.1038/nchem.121
[41]	YIN A, WEN C, GUO X, DAI W-L, FAN K. Influence of Ni species on the structural evolution of Cu/SiO₂ catalyst for the chemoselective hydrogenation of dimethyl oxalate[J]. J Catal,2011,280(1):77−88. doi: 10.1016/j.jcat.2011.03.006
[42]	HUANG H, WANG B, WANG Y, ZHAO Y, WANG S, MA X. Partial hydrogenation of dimethyl oxalate on Cu/SiO₂ catalyst modified by sodium silicate[J]. Catal Today,2020,358:68−73. doi: 10.1016/j.cattod.2019.08.048
[43]	CHEN H, TAN J, ZHU Y, LI Y. An effective and stable Ni₂P/TiO₂ catalyst for the hydrogenation of dimethyl oxalate to methyl glycolate[J]. Catal Commun,2016,73:46−49. doi: 10.1016/j.catcom.2015.10.010
[44]	ZHUANG Z, LI Y, CHEN F, CHEN X, LI Z, WANG S, WANG X, ZHU H, TAN Y, DING Y. Synthesis of methyl glycolate by hydrogenation of dimethyl oxalate with a P modified Co/SiO₂ catalyst[J]. Chem Commun,2022,58(12):1958−1961. doi: 10.1039/D1CC07003G
[45]	YAN W-Q, ZHANG J-B, XIAO L, ZHU Y-A, CAO Y-Q, ZHOU J-H, SUI Z-J, LI W, ZHOU X-G. Toward rational catalyst design for partial hydrogenation of dimethyl oxalate to methyl glycolate: A descriptor-based microkinetic analysis[J]. Catal Sci Technol,2019,9(20):5763−5773. doi: 10.1039/C9CY01198F
[46]	HAYDEN B E. Particle size and support effects in electrocatalysis[J]. Acc Chem Res,2013,46(8):1858−1866. doi: 10.1021/ar400001n
[47]	ZHOU M, BAO S, BARD A J. Probing size and substrate effects on the hydrogen evolution reaction by single isolated Pt atoms, atomic clusters, and nanoparticles[J]. J Am Chem Soc,2019,141(18):7327−7332. doi: 10.1021/jacs.8b13366
[48]	DONG G, LUO Z, CAO Y, ZHENG S, ZHOU J, LI W, ZHOU X. Understanding size-dependent hydrogenation of dimethyl oxalate to methyl glycolate over Ag catalysts[J]. J Catal,2021,401:252−261. doi: 10.1016/j.jcat.2021.07.028
[49]	WANG X, CHEN M, CHEN X, LIN R, ZHU H, HUANG C, YANG W, TAN Y, WANG S, DU Z, DING Y. Constructing copper-zinc interface for selective hydrogenation of dimethyl oxalate[J]. J Catal,2020,383:254−263. doi: 10.1016/j.jcat.2020.01.018
[50]	GIORGIANNI G, MEBRAHTU C, PERATHONER S, CENTI G, ABATE S. Hydrogenation of dimethyl oxalate to ethylene glycol on Cu/SiO₂ catalysts prepared by a deposition-decomposition method: Optimization of the operating conditions and pre-reduction procedure[J]. Catal Today,2022,390-391:343−353. doi: 10.1016/j.cattod.2021.08.032
[51]	SHI J, HE Y, MA K, TANG S, LIU C, YUE H, LIANG B. Cu active sites confined in MgAl layered double hydroxide for hydrogenation of dimethyl oxalate to ethanol[J]. Catal Today,2021,365:318−326. doi: 10.1016/j.cattod.2020.04.042
[52]	YIN S, ZHU L, WANG X, LIU Y, WANG S. The influence mechanism of solvent on the hydrogenation of dimethyl oxalate[J]. Chin J Chem Eng,2019,27(2):386−390. doi: 10.1016/j.cjche.2018.04.029
[53]	YIN A, WEN C, DAI W-L, FAN K. Ag/MCM-41 as a highly efficient mesostructured catalyst for the chemoselective synthesis of methyl glycolate and ethylene glycol[J]. Appl Catal B: Environ,2011,108-109:90−99. doi: 10.1016/j.apcatb.2011.08.013
[54]	DONG G, CAO Y, ZHENG S, ZHOU J, LI W, ZAERA F, ZHOU X. Catalyst consisting of Ag nanoparticles anchored on amine-derivatized mesoporous silica nanospheres for the selective hydrogenation of dimethyl oxalate to methyl glycolate[J]. J Catal,2020,391:155−162. doi: 10.1016/j.jcat.2020.08.018
[55]	GÖKTÜRK E, ERDAL H. Poliglikolik Asit’ in (PGA) Biyomedikal Uygulamaları[J]. SAÜ Fen Bilimleri Enstitüsü Dergisi, 2017, 1: 1
[56]	SINGH V, TIWARI M. Structure-processing-property relationship of poly(glycolic acid) for drug delivery systems 1: Synthesis and catalysis[J]. Int J Polym Sci,2010,2010:652719.
[57]	WEI L, MA S, HAO M, MA L, LIN X. Modifying anti-compression property and water-soluble ability of polyglycolic acid via melt blending with polyvinyl alcohol[J]. Polymers (Basel), 2022, 14: 16.
[58]	GAUTIER E, FUERTES P, CASSAGNAU P, PASCAULT J-P, FLEURY E. Synthesis and rheology of biodegradable poly(glycolic acid) prepared by melt ring-opening polymerization of glycolide[J]. J Polym Sci, Part A: Polym Chem,2009,47(5):1440−1449. doi: 10.1002/pola.23253
[59]	BUDAK K, SOGUT O, AYDEMIR SEZER U. A review on synthesis and biomedical applications of polyglycolic acid[J]. J Polym Res,2020,27(8):208. doi: 10.1007/s10965-020-02187-1
[60]	JEM K J, TAN B. The development and challenges of poly (lactic acid) and poly (glycolic acid)[J]. Adv Ind Eng Polym Res,2020,3(2):60−70.
[61]	CELIK F E, LAWRENCE H, BELL A T. Synthesis of precursors to ethylene glycol from formaldehyde and methyl formate catalyzed by heteropoly acids[J]. J Mol Catal A: Chem,2008,288(1):87−96.
[62]	YU X, VEST T A, GLEASON-BOURE N, KARAKALOS S G, TATE G L, BURKHOLDER M, MONNIER J R, WILLIAMS C T. Enhanced hydrogenation of dimethyl oxalate to ethylene glycol over indium promoted Cu/SiO₂[J]. J Catal,2019,380:289−296. doi: 10.1016/j.jcat.2019.10.001
[63]	LI Y, YAN S, QIAN L, YANG W, XIE Z, CHEN Q, YUE B, HE H. Effect of tin on Nb₂O₅/α-Al₂O₃ catalyst for ethylene oxide hydration[J]. J Catal,2006,241(1):173−179. doi: 10.1016/j.jcat.2006.04.030
[64]	KONG X, CHEN Z, WU Y, WANG R, CHEN J, DING L. Synthesis of Cu-Mg/ZnO catalysts and catalysis in dimethyl oxalate hydrogenation to ethylene glycol: enhanced catalytic behavior in the presence of a Mg^{2 +} dopant[J]. RSC Adv,2017,7(78):49548−49561. doi: 10.1039/C7RA09435C
[65]	ZHAO Y, ZHANG H, XU Y, WANG S, XU Y, WANG S, MA X. Interface tuning of Cu⁺/Cu⁰ by zirconia for dimethyl oxalate hydrogenation to ethylene glycol over Cu/SiO₂ catalyst[J]. J Energy Chem,2020,49:248−256. doi: 10.1016/j.jechem.2020.02.038
[66]	HE Z, LIN H, HE P, YUAN Y. Effect of boric oxide doping on the stability and activity of a Cu-SiO₂ catalyst for vapor-phase hydrogenation of dimethyl oxalate to ethylene glycol[J]. J Catal,2011,277(1):54−63. doi: 10.1016/j.jcat.2010.10.010
[67]	ZHENG J, HUANG L, CUI C-H, CHEN Z-C, LIU X-F, DUAN X, CAO X-Y, YANG T-Z, ZHU H, SHI K, DU P, YING S-W, ZHU C-F, YAO Y-G, GUO G-C, YUAN Y, XIE S-Y, ZHENG L-S. Ambient-pressure synthesis of ethylene glycol catalyzed by C₆₀-buffered Cu/SiO₂[J]. Science,2022,376(6590):288−292. doi: 10.1126/science.abm9257
[68]	DING J, LIU H, WANG M, TIAN H, WU J, YU G, WANG Y. Enhanced ethylene glycol selectivity of CuO-La₂O₃/ZrO₂ catalyst: The role of calcination temperatures[J]. ACS Omega,2020,5(43):28212−28223. doi: 10.1021/acsomega.0c03982
[69]	ZHU J, ZHAO G, MENG C, CHEN P, SHI X-R, LU Y. Superb Ni-foam-structured nano-intermetallic InNi₃C_0.5 catalyst for hydrogenation of dimethyl oxalate to ethylene glycol[J]. Chem Eng J,2021,426:130857. doi: 10.1016/j.cej.2021.130857
[70]	CUI G, MENG X, ZHANG X, WANG W, XU S, YE Y, TANG K, WANG W, ZHU J, WEI M, EVANS D G, DUAN X. Low-temperature hydrogenation of dimethyl oxalate to ethylene glycol via ternary synergistic catalysis of Cu and acid-base sites[J]. Appl Catal B: Environ,2019,248:394−404. doi: 10.1016/j.apcatb.2019.02.042
[71]	WANG M, YAO D, LI A, YANG Y, LV J, HUANG S, WANG Y, MA X. Enhanced selectivity and stability of Cu/SiO₂ catalysts for dimethyl oxalate hydrogenation to ethylene glycol by using silane coupling agents for surface modification[J]. Ind Eng Chem Res,2020,59(20):9414−9422. doi: 10.1021/acs.iecr.0c00789
[72]	YUE H, ZHAO Y, MA X, GONG J. Ethylene glycol: Properties, synthesis, and applications[J]. Chem Soc Rev,2012,41(11):4218−4244. doi: 10.1039/c2cs15359a
[73]	YU B-Y, CHIEN I L. Design and optimization of dimethyl oxalate (DMO) hydrogenation process to produce ethylene glycol (EG)[J]. Chem Eng Res Des,2017,121:173−190. doi: 10.1016/j.cherd.2017.03.012
[74]	ZALIPSKY S, HARRIS J M. Introduction to Chemistry and Biological Applications of Poly(ethylene glycol)[M]. Poly(ethylene glycol), 1997, 680: 1–13.
[75]	ZHANG B, ZHANG Y, ZHANG N, LIU J, CONG L, LIU J, SUN L, MAUGER A, JULIEN C M, XIE H, PAN X. Synthesis and interface stability of polystyrene-poly(ethylene glycol)-polystyrene triblock copolymer as solid-state electrolyte for lithium-metal batteries[J]. J Power Sources,2019,428:93−104. doi: 10.1016/j.jpowsour.2019.04.033
[76]	GEDDES C C, NIEVES I U, INGRAM L O. Advances in ethanol production[J]. Curr Opin Biotechnol,2011,22(3):312−319. doi: 10.1016/j.copbio.2011.04.012
[77]	CHEN C-C, LIN L, YE R-P, SUN M-L, YANG J-X, LI F, YAO Y-G. Mannitol as a novel dopant for Cu/SiO₂: A low-cost, environmental and highly stable catalyst for dimethyl oxalate hydrogenation without hydrogen prereduction[J]. J Catal,2020,389:421−431. doi: 10.1016/j.jcat.2020.06.008
[78]	SUN Y, MA Q, GE Q, SUN J. Tunable synthesis of ethanol or methyl acetate via dimethyl oxalate hydrogenation on confined iron catalysts[J]. ACS Catal,2021,11(8):4908−4919. doi: 10.1021/acscatal.1c00339
[79]	AI P, TAN M, ISHIKURO Y, HOSOI Y, YANG G, YONEYAMA Y, TSUBAKI N. Design of an autoreduced copper in carbon nanotube catalyst to realize the precisely selective hydrogenation of dimethyl oxalate[J]. ChemCatChem,2017,9(6):1067−1075. doi: 10.1002/cctc.201601503
[80]	DING J, WANG M, LIU H, GUO X, YU G, WANG Y. Effect of Cu content on Ce-doping CuO/ZrO₂ catalysts for low-temperature hydrogenation of dimethyl oxalate to ethanol[J]. Asia-Pac J Chem Eng, 2021, 16: 5.
[81]	ZHU Y, KONG X, LI X, DING G, ZHU Y, LI Y-W. Cu nanoparticles inlaid mesoporous Al₂O₃ As a high-performance bifunctional catalyst for ethanol synthesis via dimethyl oxalate hydrogenation[J]. ACS Catal,2014,4(10):3612−3620. doi: 10.1021/cs5009283
[82]	ZHAO S, YUE H, ZHAO Y, WANG B, GENG Y, LV J, WANG S, GONG J, MA X. Chemoselective synthesis of ethanol via hydrogenation of dimethyl oxalate on Cu/SiO₂: Enhanced stability with boron dopant[J]. J Catal,2013,297:142−150. doi: 10.1016/j.jcat.2012.10.004
[83]	ROOM R, BABOR T, REHM J. Alcohol and public health[J]. Lancet,2005,365(9458):519−530. doi: 10.1016/S0140-6736(05)17870-2
[84]	YUE H, MA X, GONG J. An alternative synthetic approach for efficient catalytic conversion of syngas to ethanol[J]. Acc Chem Res,2014,47(5):1483−1492. doi: 10.1021/ar4002697
[85]	INUI K, KURABAYASHI T, SATO S. Direct synthesis of ethyl acetate from ethanol carried out under pressure[J]. J Catal,2002,212(2):207−215. doi: 10.1006/jcat.2002.3769
[86]	GASPAR A B, ESTEVES A M L, MENDES F M T, BARBOSA F G, APPEL L G. Chemicals from ethanol—The ethyl acetate one-pot synthesis[J]. Appl Catal A: Gen,2009,363(1):109−114.
[87]	LIU W-B, ZHANG X, DAI L-X, YOU S-L. Asymmetric N-allylation of indoles through the iridium-catalyzed allylic alkylation/oxidation of indolines[J]. Angew,2012,51(21):5183−5187. doi: 10.1002/anie.201200649
[88]	WANG A, HE P, YUNG M, ZENG H, QIAN H, SONG H. Catalytic co-aromatization of ethanol and methane[J]. Appl Catal B: Environ,2016,198:480−492. doi: 10.1016/j.apcatb.2016.06.013
[89]	LI S, WANG Y, ZHANG J, WANG S, XU Y, ZHAO Y, MA X J I, RESEARCH E C. Kinetics study of hydrogenation of dimethyl oxalate over Cu/SiO₂ catalyst[J]. Ind Eng Chem,2015,54(4):1243−1250.
[90]	ZHANG L, HAN L, ZHAO G, CHAI R, ZHANG Q, LIU Y, LU Y. Structured Pd-Au/Cu-fiber catalyst for gas-phase hydrogenolysis of dimethyl oxalate to ethylene glycol[J]. Chem Commun (Camb),2015,51(52):10547−10550. doi: 10.1039/C5CC03009A
[91]	MARTíN A J, MITCHELL S, MONDELLI C, JAYDEV S, PÉREZ-RAMÍREZ J. Unifying views on catalyst deactivation[J]. Nat Catal,2022,5(10):854−866. doi: 10.1038/s41929-022-00842-y
[92]	ZHAO Y, KONG L, XU Y, HUANG H, YAO Y, ZHANG J, WANG S, MA X. Deactivation mechanism of Cu/SiO₂ catalysts in the synthesis of ethylene glycol via methyl glycolate hydrogenation[J]. Ind Eng Chem Res,2020,59(27):12381−12388. doi: 10.1021/acs.iecr.0c01619