Effect of <i>cis</i>/<i>trans</i> molecular structures on pyrolysis performance and heat sink of decalin isomers

doi:10.1007/s11705-023-2375-z

Front. Chem. Sci. Eng.

2024, Vol. 18

Issue (1) : 5 https://doi.org/10.1007/s11705-023-2375-z

RESEARCH ARTICLE

Effect of cis/trans molecular structures on pyrolysis performance and heat sink of decalin isomers

Qing Liu^1,^2,⁴, Kang Xue^1,^2,^3,⁴, Tinghao Jia¹, Zhouyang Shen^1,^2,⁴, Zehao Han^1,^2,⁴, Lun Pan^1,^2,^3,⁴(

), Ji-Jun Zou^1,^2,^3,⁴, Xiangwen Zhang^1,^2,^3,⁴(

)

¹. Key Laboratory for Green Chemical Technology of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China
². Collaborative Innovative Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
³. Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China
⁴. Zhejiang Institute of Tianjin University, Ningbo 315201, China

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Abstract

Decalin is considered as an important compound of high-energy-density endothermic fuel, which is an ideal on-board coolant for thermal management of advanced aircraft. However, decalin contains two isomers with a tunable composition, and their effects on the pyrolysis performance, such as the heat sink and coking tendency have not been demonstrated. Herein, we investigated the pyrolysis of decalin isomers, i.e., cis-decalin, trans-decalin and their mixtures (denoted as mix-decalin), in order to clarify the effects of the cis-/trans-structures on the pyrolysis performance of decalin fuels. The pyrolysis results confirmed that conversion of the tested fuels (600–725 °C, 4 MPa) decreased in the order cis-decalin > mix-decalin > trans-decalin. Detailed analyses of the pyrolysis products were used to compare the product distributions from cis-decalin, mix-decalin and trans-decalin, and the yields of some typical components (such as cyclohexene, 1-methylcyclohexene, benzene and toluene) showed significant differences, which could be ascribed to deeper cracking of cis-decalin. Additionally, the heat sinks and coking tendencies of the decalins decreased in the order cis-decalin > mix-decalin > trans-decalin. This work demonstrates the relationship between the cis/trans structures and the pyrolysis performance of decalin, which provides a better understanding of the structure-activity relationships of endothermic hydrocarbon fuels.

Keywords endothermic fuel decalin pyrolysis heat sink molecular structure

Corresponding Author(s): Lun Pan,Xiangwen Zhang

Just Accepted Date: 03 November 2023 Issue Date: 27 December 2023

Cite this article:

Qing Liu,Kang Xue,Tinghao Jia, et al. Effect of cis/trans molecular structures on pyrolysis performance and heat sink of decalin isomers[J]. Front. Chem. Sci. Eng., 2024, 18(1): 5.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-023-2375-z
https://academic.hep.com.cn/fcse/EN/Y2024/V18/I1/5

Tab.1 Structures and properties of the decalin fuels

Fig.1 (a) Thermal cracking conversions and (b) total gas yields for pyrolysis of cis-, mix-, and trans-decalin.

Tab.2 Rate constants for pyrolysis of decalin fuels under different conditions

Fig.2 Arrhenius plots of the rate constants (k) versus temperature (T) for pyrolysis of the three decalins.

Fig.3 Gaseous product distributions from pyrolysis of cis-, mix-, and trans-decalin at 725 °C.

Fig.4 (a) Liquid pyrolysis products from cis-decalin, mix-decalin and trans-decalin at 725 °C, and (b) liquid pyrolysis products from cis-decalin at 600–725 °C (1, benzene; 2, cyclohexene; 3, toluene; 4, 1-methyl-cyclohexene; 5, 2-methyl-1,3-cyclohexadiene; 6, ethylbenzene; 7, 1,2-dimethyl-cyclohexene; 8, p-xylene; 9, trans-decalin; 10, cis-decalin; 11, 1,2,3,4-tetrahydronaphthalene; 12, naphthalene).

Fig.5 Yields of the indicated liquid products from decalin at 600–725 °C.

Fig.6 (a) Total heat sink values and (b) yields of H₂ and alkenes (≤ C₄) of thermal cracking of cis-, mix-, and trans-decalin.

Fig.7 Coke deposition in the cracking processes of cis-, mix- and trans-decalin at 725 °C.

Fig.8 GC × GC images of the polycyclic aromatic hydrocarbons (acenaphthene, fluorene and phenanthrene derivatives) generated in the pyrolysis of (a) cis-decalin, (b) mix-decalin and (c) trans-decalin.

Fig.9 Mass contents of the polycyclic aromatic hydrocarbons in the liquid pyrolysis products from cis-decalin, mix-decalin and trans-decalin.

Scheme1 Coke deposition pathways of decalin.

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