Citation: JIA Jian-bo, LI Feng-hai, ZENG Fan-gui, Guo Hong-yu. A DFT study on the mechanism of methyl indan formation in tetralin pyrolysis[J]. Journal of Fuel Chemistry and Technology, ;2012, 40(10): 1188-1193. shu

A DFT study on the mechanism of methyl indan formation in tetralin pyrolysis

1.
1. Henan Polytechnic University School, Jiaozuo 454000, China;

Corresponding author: ZENG Fan-gui,
Received Date: 28 March 2012
Available Online: 20 May 2012
Fund Project: 国家自然科学基金(41072116, 40772097, 40572094, 90410018) (41072116, 40772097, 40572094, 90410018) 国家自然科学青年基金(41102092,41002047) (41102092,41002047) 高等学校博士学科点专项科研基金(20091402110002) (20091402110002)

The mechanism of methyl indan formation during tetralin pyrolysis was investigated by using the density functional theory (DFT). The results showed that 1-methyl indan is the main conformation of methyl indan products from tetralin pyrolysis. As the main route of 1-methyl indan formation during tetralin pyrolysis, β tetralin radical was first formed through H abstraction by radical species from tetralin, which then endures a ring contraction reaction to form 1-methyl indan. High temperature can promote the formation of 1-methyl indan, but has little effect on the formation routes of 1-methyl indan.
- tetralin,
- methyl indan,
- pyrolysis mechanism,
- density function theory
1. [1]
  [1] 张晓静. 煤炭直接液化溶剂的研究[J]. 洁净煤技术, 2011, 17(4): 26-29. (ZHANG Xiao-jing. Study on solvents for direct coal liquefaction[J]. Clean Coal Technology, 2011, 17(4): 26-29.)
2. [2]
  [2] 王绍清, 唐跃刚, Harold H Schobert, 郭琴, 王凤娟. 富含树皮体和半丝质体媒的液化反应性和¹³C-核磁共振分析的研究[J]. 燃料化学学报. 2010, 38(2): 129-133. (WANG Shao-qing, TANG Yue-gang, SCHOBERT H H, GUO Qin, WANG Feng-juan. Liquefaction reactivity and ¹³C-NMR of coals rich in barkinite and semi-fusinite[J]. Journal of Fuel Chemistry and Technology, 2010, 38(2): 129-133.)
3. [3]
  [3] 徐蓉, 王国龙, 鲁锡兰, 李洋洋, 张德祥. 神华煤液化残渣的加氢反应动力学[J]. 化工学报, 2009, 60(11): 2749-2754. (XU Rong, WANG Guo-long, LU Xi-lan, LI Yang-yang, ZHANG De-xiang.Hydrogenation kinetics of Shenhua coal liquefaction residue [J].Journal of Chemical Industry and Engineering(China), 2009, 60(11): 2749-2754.)
4. [4]
  [4] LI X, HU S X, JIN L J, HU H Q.Role of iron-based catalyst and hydrogen transfer in direct coal liquefaction[J].Energy Fuels, 2008, 22(2): 1126-1129.
5. [5]
  [5] HOOPER J R, HENDRIK A J, BATTAERD J, EVANS D G.Thermal dissociation of tetralin between 300 and 450℃[J].Fuel, 1979, 58(2): 132-138.
6. [6]
  [6] CURRAN G.P, STRUCK R T, GORIN E.Mechanism of hydrogen-transfer process to coal and coal extract[J].Ind Eng Chem Process Des Dev, 1967, 6(2): 166-173.
7. [7]
  [7] BOUNACEUR R, SCACCHI G, MARQUAIRE P M, DOMIN F.Mechanistic modeling of the thermal cracking of tetralin[J].Ind Eng Chem Res, 2000, 39(11): 4152-4165.
8. [8]
  [8] POUTSMA M.L.Progress toward the mechanistic description and simulation of the pyrolysis of tetralin[J]Energy Fuels, 2002, 16(4): 964-996.
9. [9]
  [9] POUTSMA M L.Free-radical thermolysis and hydrogenolysis of model hydrocarbons relevant to processing of coal[J].Energy Fuels,1990, 4(2): 113-131.
10. [10]
  [10] YEN Y K, FURLANI D E, WELLER S W.Batch autoclave studies of catalytic hydrodesulfurization of coal[J].Ind Eng Chem Prod Dev, 1976, 15(1): 24-28.
11. [11]
  [11] BENJAMIN B M, HAGAMAN E W, RAAEN V F, COLLINS C J.Pyrolysis of tetralin[J].Fuel, 1979, 58(5): 386-390.
12. [12]
  [12] PENNINGER J M L.New aspects of the mechanism for the thermal hydrocracking of indane and tetralin[J].Int J Chem Kinet, 1982, 14(7): 761-780.
13. [13]
  [13] 杨晓林, 杨惠星, 韩德刚.四氢萘(C₁₀H₁₂)热解反应动力学研究[J].物理化学学报, 1985, 1(3): 249-257. (YANG Xiao-lin, YANG Hui-xing, HAN De-gang.Kinetics and mechanism of thermolysis of tetralin[J].Acta Physico-Chimica Sinica, 1985, 1(3): 249-257.)
14. [14]
  [14] 杨晓林, 应立明, 覃志伟.四氢萘热解反应机理研究[J].化学学报, 1990, 48(5): 441-446. (YANG Xiao-lin, YING Li-ming, TAN Zhi-wei.The study of mechanism for the thermolysis of tetralin[J].Acta Chimica Sinica, 1990, 48(5): 441-446.)
15. [15]
  [15] 杨晓林, 杨惠星, 韩德刚.四氢萘热解中间产物及其反应机理的进一步研究[J].物理化学学报, 1985, 1(6): 571-574. (YANG Xiao-lin, YANG Hui-xing, HAN De-gang.The study of the intermediates reactions and the reaction mechanism in the thermolysis of tetraline [J].Acta Physico-Chimica Sinica, 1985, 1(6): 571-574.)
16. [16]
  [16] 贾建波, 曾凡桂, 李美芬, 谢克昌.煤中芳核侧链模型化合物丁基蒽的初次热解[J].化工学报, 2009, 60(12): 3082-3088. (JIA Jian-bo, ZENG Fan-gui, LI Mei-fen, XIE Ke-chang.Initial pyrolysis mechanism of aliphatic group on aromatic cluster in coal structure by using butyl anthracene as model compound[J].Journal of Chemical Industry and Engineering(China), 2009, 60(12): 3082-3088.)
17. [17]
  [17] 傅献彩, 沈文霞, 姚天扬. 物理化学[M].北京: 高等教育出版社, 1993: 806-811. (FU Xian-cai, SHEN Wen-xia, YAO Tian-yang.Physical chemistry [M].Beijing: Higher Education Press, 1993: 806-811.)
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