Volume 50 Issue 4
Apr.  2022
Turn off MathJax
Article Contents
YANG Wei-qiang, MAO Kai-ming, MO Wen-long, MA Feng-yun, WEI Xian-yong, FAN Xin, REN Tie-zhen. Mechanism analysis of methanol alcoholysis of Naomaohu lignite extraction residue based on model compound reaction path[J]. Journal of Fuel Chemistry and Technology, 2022, 50(4): 396-407. doi: 10.1016/S1872-5813(21)60178-0
Citation: YANG Wei-qiang, MAO Kai-ming, MO Wen-long, MA Feng-yun, WEI Xian-yong, FAN Xin, REN Tie-zhen. Mechanism analysis of methanol alcoholysis of Naomaohu lignite extraction residue based on model compound reaction path[J]. Journal of Fuel Chemistry and Technology, 2022, 50(4): 396-407. doi: 10.1016/S1872-5813(21)60178-0

Mechanism analysis of methanol alcoholysis of Naomaohu lignite extraction residue based on model compound reaction path

doi: 10.1016/S1872-5813(21)60178-0
Funds:  The project was supported by Tianchi Project for Introducing Highlevel Talents to Xinjiang Uyghur Autonomous Region (China), Key Laboratory of Coal Processing and Efficient Utilization from Ministry of Education and Open Project of Key Laboratory of Xinjiang Uygur Autonomous Region (2018D04008)
  • Received Date: 2021-10-09
  • Accepted Date: 2021-11-02
  • Rev Recd Date: 2021-11-01
  • Available Online: 2022-01-10
  • Publish Date: 2022-04-26
  • Ultrasonic assisted extraction residue (ER) from Naomaohu lignite (NL) was taken as the research object. ER was subjected to methanolysis at 300 ℃, and the effect of KOH was investigated. Composition of the two alcoholysis products, MP (without KOH) and MPKOH (with KOH) was analyzed by chromatograph/mass spectrometer (GC-MS). Benzyl benzoate (BB) and phenyl acetate (PA) were selected as model compounds (MER) for ER, and the alcoholysis products (BBP, BBPKOH, PAP and PAPKOH) were obtained. Results showed that the yield of MPKOH was 93.39%, while that of MP was only 5.25%, indicating that the addition of KOH greatly improved the yield of alcoholysis product. MP consisted of phenols, esters and alkanes with the relative contents of 17.92%, 34.83% and 5.98%, respectively, while the contents of the above three compounds in MPKOH were 34.8%, 10.17% and 8.71% respectively, indicating that transesterification or ester reduction reaction occurred in the alcoholysis process with the addition of KOH accompanied by alkylation reaction. Analysis of alcoholysis products of model compounds showed that methyl benzoate and benzyl alcohol were predominant in BBP, while methyl benzoate disappeared in BBPKOH, and the relative content of benzyl alcohol accounted for 91.85%; phenols were only detected in PAP, and the relative content of phenol was 87.97%. Whereas, the content of methyl substituted anisole and phenol accounted for the largest share in PAPKOH with the contents of 85.64%. Alcoholysis process of the two model compounds showed that, without KOH, transesterification or ester reduction reaction was occurred in the alcoholysis process. And the addition of KOH not only accelerated the above reaction, but also strengthened the alkylation reaction between the subsequent products and methanol.
  • loading
  • [1]
    WU J H, LIU J Z, ZHANG X, WANG Z H, ZHOU J H, CEN K F. Chemical and structural changes in Ximeng lignite and its carbon migration during hydrothermal dewatering[J]. Fuel,2015,148:139−144. doi: 10.1016/j.fuel.2015.01.102
    [2]
    LI Z K, WEI X Y, YAN H L, ZONG Z M. Insight into the structural features of Zhaotong lignite using multiple techniques[J]. Fuel,2015,153:176−182. doi: 10.1016/j.fuel.2015.02.117
    [3]
    CONG X S, ZONG Z M, ZHOU Y, LI M, WANG W L, LI F G, ZHOU J, FAN X, ZHAO Y P, WEI X Y. Isolation and identification of 3-ethyl-8-methyl-2, 3-dihydro-1 H-cyclopenta [a] chrysene from Shengli lignite[J]. Energy Fuels,2014,28(10):6694−6697. doi: 10.1021/ef402403y
    [4]
    LU H Y, Wei X Y, YU R, PENG Y L, QI X Z, QIE L M, WEI Q, LV J, ZHONG Z M, ZHAO W, ZHAO Y P, NI Z H, WU L. Sequential thermal dissolution of Huolinguole lignite in methanol and ethanol[J]. Energy Fuels,2011,25(6):2741−2745. doi: 10.1021/ef101734f
    [5]
    YU X Y, WEI X Y, LI Z K, ZANG D D, ZONG Z M. Two-step depolymerization of Zhaotong lignite in ethanol[J]. Fuel,2017,196(15):391−397.
    [6]
    LIU F J, WEI X Y, ZHU Y, GUI J, WANG Y G, FAN X, ZHAO Y P, ZONG Z M, ZHAO W. Investigation on structural features of Shengli lignite through oxidation under mild conditions[J]. Fuel,2013,109:316−324. doi: 10.1016/j.fuel.2013.01.020
    [7]
    ROSS D S, BLESSING J E. Alcohols as H-donor media in coal conversion. 2. Base-promoted H-donation to coal by methyl alcohol[J]. Fuel,1979,58(6):438−442. doi: 10.1016/0016-2361(79)90085-1
    [8]
    LI S, ZONG Z M, LI Z K, WANG S K, YANG Z, XU M L, SHI C, WEI X Y, WANG Y G. Sequential thermal dissolution and alkanolyses of extraction residue from Xinghe lignite[J]. Fuel Process Technol,2017,167:425−430. doi: 10.1016/j.fuproc.2017.07.025
    [9]
    LI Z K, ZONG Z M, YANG Z S, YAN H L, FAN X, WEI X Y. Sequential thermal dissolution of Geting bituminous coal in low-boiling point solvents[J]. Energy Sources, Part A: Recovery, Utilization, and Environmental Effects,2014,36(23):2579−2586. doi: 10.1080/15567036.2013.869639
    [10]
    PAN C X, WEI X Y, SHUI H F, WANG Z C, GAO J, WEI C, GAO X Z, ZONG Z M. Investigation on the macromolecular network structure of Xianfeng lignite by a new two-step depolymerization[J]. Fuel,2013,109:49−53. doi: 10.1016/j.fuel.2012.11.059
    [11]
    LEI Z P, LIU M X, SHUI H F, WANG Z C, WEI X Y. Study on the liquefaction of Shengli lignite with NaOH/methanol[J]. Fuel Process Technol,2010,91(7):783−788. doi: 10.1016/j.fuproc.2010.02.014
    [12]
    LIU F J, WEI X Y, LI W T, GUI J, LI P, WANG Y G, XIE R L, ZONG Z M. Methanolysis of extraction residue from Xianfeng lignite with NaOH and product characterizations with different spectrometries[J]. Fuel Process Technol,2015,136:8−16. doi: 10.1016/j.fuproc.2014.07.012
    [13]
    LI S, ZONG Z M, WANG S K, XU M L, WEI X Y, LIU F J. Compositional features of the extracts from the methanolysis of Xilingol No. 6 lignite[J]. Fuel,2019,246:516−520. doi: 10.1016/j.fuel.2018.11.133
    [14]
    毛凯敏, 莫文龙, 马凤云, 马亚亚, 王越, 魏贤勇, 樊星. 淖毛湖褐煤分级萃取可溶有机质的组成结构特征及萃余残渣的热转化性能[J]. 燃料化学学报,2021,49(10):1389−1401. doi: 10.1016/S1872-5813(21)60117-2

    (MAO Kai-min, MO Wen-long, MA Feng-yun, MA Ya-ya, WANG Yue, WEI Xian-yong, FAN Xing. Composition and structure characteristics of soluble organic matter from Naomaohu lignite by sequential extraction and thermal conversion performance of the corresponding residue[J]. J Fuel Chem Technol,2021,49(10):1389−1401. doi: 10.1016/S1872-5813(21)60117-2
    [15]
    XU M L, WEI X Y, YU X Y, LIU F J, WU Q C, LI S, WANG S K, LIU G H, LIU Z Q, GUO X H, ZHANG Y Y, ZONG Z M. Insight into molecular compositions of soluble species from sequential thermal dissolution of Liuhuanggou bituminous coal and its extraction residue[J]. Fuel,2019,253:762−771. doi: 10.1016/j.fuel.2019.05.045
    [16]
    GAO Y, WEI X Y, LI Y J, BAI J J, KANG Y H, LIU G H, MA X R, LI X, LU C Y, BAI H C, ZONG Z M. Investigation on the composition of soluble portions from the extraction residue of Hanglaiwan subbituminous coal by thermal dissolution and alkanolyses[J]. Fuel,2021,306:121747. doi: 10.1016/j.fuel.2021.121747
    [17]
    夏同成, 魏贤勇, 刘卫兵, 卿宇, 路瑶, 宗志敏, 许斌, 王世杰, 李春启. 锡林浩特褐煤的超临界甲醇解研究[J]. 武汉科技大学学报,2009,32(6):627−630.

    XIA Tong-cheng, WEI Xian-yong, LIU Wei-bing, QinYu, LU Yao, Zong Zhi-ming, XU Bing, WANG Shi-jie, LI Chong-qi. Supercritical methanolysis of Xilinhaote lignite[J]. J Wuhan Univ Sci Technol,2009,32(6):627−630.
    [18]
    KANG Y H, WEI X Y, ZHAN X Q, LI Y J, LIU G H, MA X R, LI X, BAI H C, LI Z N, YAN H J, ZONG Z M. Deep catalytic hydroconversion of straw-derived bio-oil to alkanes over mesoporous zeolite Y supported nickel nanoparticles[J]. Renewable Energy,2021,173:876−885. doi: 10.1016/j.renene.2021.04.003
    [19]
    李白雪, 薛锋, 王建, 丁恩勇. 聚碳酸酯在乙二醇中的可控醇解[J]. 塑料工业,2015,43(3):127−131. doi: 10.3969/j.issn.1005-5770.2015.03.022

    LI Bai-xue, XUE Feng, WANG Jian, Ding En-yong. Controllable glycolysis of polycarbonate in ethylene glycol[J]. China Plastics Ind,2015,43(3):127−131. doi: 10.3969/j.issn.1005-5770.2015.03.022
    [20]
    YIN J N, LIN X C, WANG C H, DAI J Z, WANG Y G, XU Z G. Identification of the transformation features of heteroatomic compounds in a low rank coal by combining thermal extraction and various analytical approaches[J]. Fuel,2020,270:117480. doi: 10.1016/j.fuel.2020.117480
    [21]
    SHUI H F, MA X Q, YANG L, SHUI T, PAN C X, WANG Z C, LEI Z P, REN S B, KANG S G, CHARLES XU C B. Thermolysis of biomass-related model compounds and its promotion on the thermal dissolution of coal[J]. J Energy Ins,2017,90(3):418−423. doi: 10.1016/j.joei.2016.04.001
    [22]
    WANG T M, ZONG Z M, LIU F J, LUI C, LV J H, JING L, ZANG D D, QU M, GUI J, LIU X X, WEI X Y, WEI Z H, LI Y. Investigation on compositional and structural features of Xianfeng lignite through sequential thermal dissolution[J]. Fuel Process Technol,2015,138:125−132. doi: 10.1016/j.fuproc.2015.04.029
    [23]
    MONDRAGON F, ITOH H, OUCHI K. Solubility increase of coal by alkylation with various alcohols[J]. Fuel,1982,61(11):1131−1134. doi: 10.1016/0016-2361(82)90198-3
    [24]
    GAO H S, ZONG Z M, TENG D G, LI J H, WEI X Y, GUO Q J, ZHAO T S, BAI H C, KANG Y H. Catalytic o-methylation of phenols and its application in converting crude phenols in a low-temperature coal tar to mesitol and durenol[J]. Fuel,2021,288:119681. doi: 10.1016/j.fuel.2020.119681
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Article Metrics

    Article views (414) PDF downloads(50) Cited by()
    Proportional views
    Related

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return