Volume 51 Issue 3
Mar.  2023
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ZHANG Fu-can, LIU Ping, ZHANG Kan, JI Ke-ming, ZHANG Jian-li, ZHAO Liang, SONG Qing-wen. Selective synthesis of dimethyl carbonate via the coupling reaction of CO2 and alcohols by the synergistic catalysis of silver sulfadiazine and superbase[J]. Journal of Fuel Chemistry and Technology, 2023, 51(3): 304-313. doi: 10.1016/S1872-5813(22)60053-7
Citation: ZHANG Fu-can, LIU Ping, ZHANG Kan, JI Ke-ming, ZHANG Jian-li, ZHAO Liang, SONG Qing-wen. Selective synthesis of dimethyl carbonate via the coupling reaction of CO2 and alcohols by the synergistic catalysis of silver sulfadiazine and superbase[J]. Journal of Fuel Chemistry and Technology, 2023, 51(3): 304-313. doi: 10.1016/S1872-5813(22)60053-7

Selective synthesis of dimethyl carbonate via the coupling reaction of CO2 and alcohols by the synergistic catalysis of silver sulfadiazine and superbase

doi: 10.1016/S1872-5813(22)60053-7
Funds:  The project was supported by the Natural Science Foundation of Shanxi (20210302123002, 202103021223460), Technical research and development project from Lu'an Chemical Industry Group Co., Ltd. and the Foundation of State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering (2022-K20).
  • Received Date: 2022-05-19
  • Accepted Date: 2022-07-13
  • Rev Recd Date: 2022-07-07
  • Available Online: 2022-07-28
  • Publish Date: 2023-03-15
  • The three-component coupling of methanol, CO2 and propargyl alcohol to manufacture dimethyl carbonate (DMC) provides a new, thermodynamic favorable and green chemical synthesis route. In this work, to overcome the problems of low DMC yield and slow conversion rate of intermediates, the synergistic catalytic strategy of silver sulfadiazine and superbase is developed to improve the reaction efficiency. The effect of various parameters i.e. catalyst and cocatalyst types, catalyst loading, solvent, temperature, proportion of raw materials, pressure and time on the coupling reactions is investigated in detail. Under the optimal conditions, the selectivity of DMC is 89.5% with the yield of 55.6%. And the effect of alkyne derivative α-monosubstituted propargyl alcohol on the efficiency and selectivity of DMC are also studied. The mechanism study shows that propargyl alcohols with different structures apparently affect the reaction process, and the synergistic catalysis of silver sulfadiazine/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is the reason for the high yield and selectivity of DMC.
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  • [1]
    SONG Q W, ZHOU Z H, HE L N. Efficient, selective and sustainable catalysis of carbon dioxide[J]. Green Chem,2017,19(16):3707−3728. doi: 10.1039/C7GC00199A
    [2]
    LU M, ZHANG M, LIU J, CHEN Y, LIAO J P, YANG M Y, CAI Y P, LI S L, LAN Y Q. Covalent organic framework based functional materials: important catalysts for efficient CO2 utilization[J]. Angew Chem Int Ed,2022,61(15):e202200003.
    [3]
    HE X, QIU L Q, WANG W J, CHEN K H, HE L N. Photocarboxylation with CO2: an appealing and sustainable strategy for CO2 fixation[J]. Green Chem,2020,22(21):7301−7320. doi: 10.1039/D0GC02743J
    [4]
    AOMCHAD V, CRISTOFOL A, DELLA F, LIMBURG B, DELIA V, KLEIJ A W. Recent progress in the catalytic transformation of carbon dioxide into biosourced organic carbonates[J]. Green Chem,2021,23(3):1077−1113. doi: 10.1039/D0GC03824E
    [5]
    BURKART M D, HAZARI N, TWAY C L, ZEITLER E L. Opportunities and challenges for catalysis in carbon dioxide utilization[J]. ACS Catal,2019,9(9):7937−7956. doi: 10.1021/acscatal.9b02113
    [6]
    TAN H Z, WANG Z Q, XU Z N, SUN J, XU Y P, CHEN Q S, CHEN Y, GUO G C. Review on the synthesis of dimethyl carbonate[J]. Catal Today,2018,316:2−12. doi: 10.1016/j.cattod.2018.02.021
    [7]
    KUMAR P, SRIVASTAVA V C, STANGAR U L, MUSIC B, MISHRA I M, MENG Y. Recent progress in dimethyl carbonate synthesis using different feedstock and techniques in the presence of heterogeneous catalysts[J]. Catal Rev,2019,63(3):363−421.
    [8]
    TAMBOLI A H, CHAUGULE A A, KIM H. Catalytic developments in the direct dimethyl carbonate synthesis from carbon dioxide and methanol[J]. Chem Eng J,2017,323:530−544. doi: 10.1016/j.cej.2017.04.112
    [9]
    BALLIVET D, JERPHAGNON T, LIGABUE R, PLASSERAUD L, POINSOT D. The role of distannoxanes in the synthesis of dimethyl carbonate from carbon dioxide[J]. Appl Catal A: Gen,2003,255(1):93−99. doi: 10.1016/S0926-860X(03)00647-1
    [10]
    HONDA M, TAMURA M, NAKAGAWA Y, SONEHARA S, SUZUKI K, FUJIMOTO K, TOMISHIGE K. Ceria-catalyzed conversion of carbon dioxide into dimethyl carbonate with 2-cyanopyridine[J]. ChemSusChem,2013,6(8):1341−1346. doi: 10.1002/cssc.201300229
    [11]
    HE H, QI C, HU X, GUAN Y, JIANG H. Efficient synthesis of tertiary α-hydroxy ketones through CO2-promoted region-selective hydration of propargylic alcohols[J]. Green Chem,2014,16(8):3729−3733. doi: 10.1039/C4GC00522H
    [12]
    ZHAO Y, YANG Z, YU B, ZHANG H, XU H, HAO L, HAN B, LIU Z. Task-specific ionic liquid and CO2-cocatalysed efficient hydration of propargylic alcohols to α-hydroxy ketones[J]. Chem Sci,2015,6(4):2297−2301. doi: 10.1039/C5SC00040H
    [13]
    ZHOU Z H, SONG Q W, HE L N. Silver(I)-promoted cascade reaction of propargylic alcohols, carbon dioxide, and vicinal diols: thermodynamically favorable route to cyclic carbonates[J]. ACS Omega,2017,2(1):337−345. doi: 10.1021/acsomega.6b00407
    [14]
    ZHOU H, ZHANG H, MU S, ZHANG W Z, REN W M, LU X B. Highly regio and stereoselective synthesis of cyclic carbonates from biomass-derived polyols via organocatalytic cascade reaction[J]. Green Chem,2019,21(23):6335−6341. doi: 10.1039/C9GC03013A
    [15]
    HU J, MA J, LU L, QIAN Q, ZHANG Z, XIE C, HAN B. Synthesis of asymmetrical organic carbonates using CO2 as a feedstock in AgCl/ionic liquid system at ambient conditions[J]. ChemSusChem,2017,10(6):1292−1297. doi: 10.1002/cssc.201601773
    [16]
    张乾霞, 刘平, 张侃, 韩丽华, 宋清文. 多组分串联策略固定CO2制碳酸二甲酯和α-羟基酮[J]. 科学通报,2020,65(31):3429−3437. doi: 10.1360/TB-2020-0351

    ZHANG Qian-xia, LIU Ping, ZHANG Kan, HAN Li-hua, SONG Qing-wen. Multicomponent cascade strategy of CO2 fixation for synthesis of dimethyl carbonate and α-hydroxy ketone[J]. Chin Sci Bull,2020,65(31):3429−3437. doi: 10.1360/TB-2020-0351
    [17]
    SONG Q W, CHEN W Q, MA R, YU A, LI Q Y, CHANG Y, HE L N. Bifunctional silver(I) complex-catalyzed CO2 conversion at ambient conditions: synthesis of α-methylene cyclic carbonates and derivatives[J]. ChemSusChem,2015,8(5):821−827. doi: 10.1002/cssc.201402921
    [18]
    YUAN Y, XIE Y, ZENG C, SONG D, CHAEMCHUEN S, CHEN C, VERPOORT F. A simple and robust AgI/KOAc catalytic system for the carboxylative assembly of propargyl alcohols and carbon dioxide at atmospheric pressure[J]. Catal Sci Technol,2017,7(14):2935−2939. doi: 10.1039/C7CY00696A
    [19]
    LI J Y, HAN L H, XU Q C, SONG Q W, LIU P, ZHANG K. Cascade strategy for atmospheric pressure CO2 fixation to cyclic carbonates via silver sulfadiazine and Et4NBr synergistic catalysis[J]. ACS Sustainable Chem Eng,2019,7(3):3378−3388. doi: 10.1021/acssuschemeng.8b05579
    [20]
    CERVANTES R A, SAXL T, STEIN P M, RUDOLPH M, ROMINGER F, ASIRI A M, HASHMI A S. Expanded ring NHC silver carboxylate complexes as efficient and reusable catalysts for the carboxylative cyclization of unsubstituted propargylic derivatives[J]. ChemSusChem,2021,14(11):2367−2374. doi: 10.1002/cssc.202002822
    [21]
    MCCORMACK A C, OFERRALL R A, ODONOGHU A C, RAO S N. Protonated benzofuran, anthracene, naphthalene, benzene, ethene, and ethyne:   measurements and estimates of pKa and pKR[J]. J Am Chem Soc,2002,124(29):8575−8583. doi: 10.1021/ja012613x
    [22]
    CA N D, GABRIELE B, RUFFOLO G, VELTRI L, ZANETTA T, COSTA M. Effective Guanidine-catalyzed synthesis of carbonate and carbamate derivatives from propargyl alcohols in supercritical carbon dioxide[J]. Adv Synth Catal,2011,353(1):133−146. doi: 10.1002/adsc.201000607
    [23]
    ZHOU Z H, SONG Q W, XIE J N, MA R, HE L N. Silver(I)-catalyzed three-component reaction of propargylic alcohols, carbon dioxide and monohydric alcohols: Thermodynamically feasible access to β-oxopropyl carbonates[J]. Chem-Asian J,2016,11(14):2065−2071.
    [24]
    SEKINE K, YAMADA T. Silver-catalyzed carboxylation[J]. Chem Soc Rev,2016,45(16):4524−4532. doi: 10.1039/C5CS00895F
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