Synthesis of bio-based cyclic carbonate from vegetable oil methyl ester by CO2 fixation with acid-base pair MOFs

被引:17
作者
Cai, Tingting [1 ]
Liu, Jianxing [1 ]
Cao, Hui [1 ]
Cui, Caixia [2 ]
机构
[1] Beijing Univ Chem Technol, Coll Biol Sci & Technol, Beijing Key Lab Bioproc, Natl Energy R&D Ctr Biorefinery, Beijing 100029, Peoples R China
[2] Xinxiang Med Univ, Sch Life Sci & Technol, Synthet Biol Engn Lab Henan Prov, Xinxiang 453003, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
Vegetable oil methyl ester; CO2; fixation; Cyclic carbonates; MOFs; Epoxidation; METAL-ORGANIC FRAMEWORKS; FATTY-ACIDS; EPOXIDATION; LIPASE; VALORIZATION; TEMPERATURE; PERFORMANCE; ADSORPTION; CONVERSION; CATALYSIS;
D O I
10.1016/j.indcrop.2020.112155
中图分类号
S2 [农业工程];
学科分类号
0828 ;
摘要
Bio-based five-membered cyclic carbonates were synthesized from renewable O-acetyl methyl ricinoleate that from crops and CO2 via two steps and the products after each reaction step were characterized by fourier transform infrared spectroscopy. For the acid-catalyzed process, O-acetyl methyl ricinoleate epoxidation of unsaturated double bonds was accomplished using lipase as a sustainable replacement. The effect of different experimental conditions, including the solvent, initiator types, initiator ratios, enzyme amount, reaction temperature, and reaction time, on epoxide conversion was analyzed. O-acetyl methyl ricinoleate conversion reached 95 % under the optimized reaction conditions and the resulting epoxide was subsequently reacted with CO2 using the acid-base pair UiO-66-NH2 to produce cyclic carbonate. CO2 adsorption and fixation occurred simultaneously due to the use of bifunctional UiO-66-NH2 and epoxide conversion reached 94.4 % with CO2 using UiO-66-NH2. The substrates applicability was tested after each step and it was found that more than 92 % of the fatty acid methyl esters were converted into their corresponding epoxides and more than 90 % epoxide conversion occurred, with the exception of epoxy methyl linolenate (85.4 %) due to the presence of multiple double bonds in methyl linolenate. These results demonstrate this reaction scheme can be efficiently adopted for vegetable oil methyl esters.
引用
收藏
页数:8
相关论文
共 40 条
  • [1] Selective Epoxidation of Fatty Acids and Fatty Acid Methyl Esters by Fungal Peroxygenases
    Aranda, Carmen
    Olmedo, Andres
    Kiebist, Jan
    Scheibner, Katrin
    del Rio, Jose C.
    Martinez, Angel T.
    Gutierrez, Ana
    [J]. CHEMCATCHEM, 2018, 10 (18) : 3964 - 3968
  • [2] Catalysis for the Valorization of Exhaust Carbon: from CO2 to Chemicals, Materials, and Fuels. Technological Use of CO2
    Aresta, Michele
    Dibenedetto, Angela
    Angelini, Antonella
    [J]. CHEMICAL REVIEWS, 2014, 114 (03) : 1709 - 1742
  • [3] Formation of Methyl Acrylate from CO2 and Ethylene via Methylation of Nickelalactones
    Bruckmeier, Christian
    Lehenmeier, Maximilian W.
    Reichardt, Robert
    Vagin, Sergei
    Rieger, Bernhard
    [J]. ORGANOMETALLICS, 2010, 29 (10) : 2199 - 2202
  • [4] Organocatalyzed Synthesis of Oleochemical Carbonates from CO2 and Renewables
    Buettner, Hendrik
    Steinbauer, Johannes
    Wulf, Christoph
    Dindaroglu, Mehmet
    Schmalz, Hans-Guenther
    Werner, Thomas
    [J]. CHEMSUSCHEM, 2017, 10 (06) : 1076 - 1079
  • [5] Iron-Based Binary Catalytic System for the Valorization of CO2 into Biobased Cyclic Carbonates
    Buettner, Hendrik
    Grimmer, Christoph
    Steinbauer, Johannes
    Werner, Thomas
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (09): : 4805 - 4814
  • [6] Cr(salophen) Complex Catalyzed Cyclic Carbonate Synthesis at Ambient Temperature And Pressure
    Castro-Osma, Jose A.
    Lamb, Katie J.
    North, Michael
    [J]. ACS CATALYSIS, 2016, 6 (08): : 5012 - 5025
  • [7] Iron(II) Bis-CNN Pincer Complex-Catalyzed Cyclic Carbonate Synthesis at Room Temperature
    Chen, Fei
    Liu, Ning
    Dai, Bin
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (10): : 9065 - 9075
  • [8] Synthesis of biosafe isosorbide dicaprylate ester plasticizer by lipase in a solvent-free system and its sub-chronic toxicity in mice
    Cui, Caixia
    Zhen, Yueju
    Qu, Junge
    Chen, Biqiang
    Tan, Tianwei
    [J]. RSC ADVANCES, 2016, 6 (15): : 11959 - 11966
  • [9] Improving performance of Yarrowia lipolytica lipase lip2-catalyzed kinetic resolution of (R, S)-1-phenylethanol by solvent engineering
    Cui, Caixia
    Xie, Rong
    Tao, Yifeng
    Zeng, Qingqian
    Chen, Biqiang
    [J]. BIOCATALYSIS AND BIOTRANSFORMATION, 2015, 33 (01) : 38 - 43
  • [10] Catalytic synthesis of cyclic carbonates from epoxides and carbon dioxide by magnetic UiO-66 under mild conditions
    Delavari, Mahbube
    Zadehahmadi, Farnaz
    Tangestaninejad, Shahram
    Moghadam, Majid
    Mirkhani, Valiollah
    Mohammadpoor-Baltork, Iraj
    Kardanpour, Reihaneh
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (07)