Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine

doi:10.1016/j.cjche.2022.09.015

Chinese Journal of Chemical Engineering ›› 2023, Vol. 56 ›› Issue (4): 225-232.DOI: 10.1016/j.cjche.2022.09.015

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Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine

Tinghao Jia^1,2,3, Yunbo Yu^1,2, Qing Liu³, Yao Yang^1,2, Ji-Jun Zou^3,4, Xiangwen Zhang^3,4, Lun Pan^3,4

1. Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China;
2. ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311200, China;
3. Key Laboratory for Green Chemical Technology of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
4. Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China

Received:2022-07-21 Revised:2022-09-06 Online:2023-06-13 Published:2023-04-28
Contact: Lun Pan,E-mail:panlun76@tju.edu.cn
Supported by:
The authors appreciate the financial support from the Postdoctoral Science Foundation of China (2021M702810), the Haihe Laboratory of Sustainable Chemical Transformations (CYZC202103), and the National Natural Science Foundation of China (21978200 and 22222808).

Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine

Tinghao Jia^1,2,3, Yunbo Yu^1,2, Qing Liu³, Yao Yang^1,2, Ji-Jun Zou^3,4, Xiangwen Zhang^3,4, Lun Pan^3,4

1. Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China;
2. ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311200, China;
3. Key Laboratory for Green Chemical Technology of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
4. Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China

通讯作者: Lun Pan,E-mail:panlun76@tju.edu.cn
基金资助:
The authors appreciate the financial support from the Postdoctoral Science Foundation of China (2021M702810), the Haihe Laboratory of Sustainable Chemical Transformations (CYZC202103), and the National Natural Science Foundation of China (21978200 and 22222808).

Abstract

Abstract: Antioxidants addition is believed as a facile and effective way to improve jet fuel thermal oxidation stability. However, amine antioxidants, as one of the most important antioxidants, have not received sufficient attention in the field of jet fuel autoxidation yet. Herein, the inhibition efficiency and mechanism of decane and exo-tetrahydrodicyclopentadiene (THDCPD) oxidation by di-4-tert-butylphenylamine (diarylamine) was experimentally and theoretically investigated. The results show that diarylamine can significantly inhibit decane oxidation but is less efficient for THDCPD oxidation, which is attributed to the higher energy barrier of retro-carbonyl-ene reaction (rate-determining step) in THDCPD than that in decane during diarylamine regeneration. However, the addition of diarylamine will cause undesirable color change after accelerated oxidation and produce slightly more deposits during high-temperature thermal oxidative stress for both decane and THDCPD. The results provide significant implications for the future design of effective antioxidant additives for high-performance jet fuel.

Key words: Jet fuel, Thermal oxidation stability, High-energy–density fuel, Diarylamine, Antioxidation mechanism

摘要： Antioxidants addition is believed as a facile and effective way to improve jet fuel thermal oxidation stability. However, amine antioxidants, as one of the most important antioxidants, have not received sufficient attention in the field of jet fuel autoxidation yet. Herein, the inhibition efficiency and mechanism of decane and exo-tetrahydrodicyclopentadiene (THDCPD) oxidation by di-4-tert-butylphenylamine (diarylamine) was experimentally and theoretically investigated. The results show that diarylamine can significantly inhibit decane oxidation but is less efficient for THDCPD oxidation, which is attributed to the higher energy barrier of retro-carbonyl-ene reaction (rate-determining step) in THDCPD than that in decane during diarylamine regeneration. However, the addition of diarylamine will cause undesirable color change after accelerated oxidation and produce slightly more deposits during high-temperature thermal oxidative stress for both decane and THDCPD. The results provide significant implications for the future design of effective antioxidant additives for high-performance jet fuel.

关键词: Jet fuel, Thermal oxidation stability, High-energy–density fuel, Diarylamine, Antioxidation mechanism

Tinghao Jia, Yunbo Yu, Qing Liu, Yao Yang, Ji-Jun Zou, Xiangwen Zhang, Lun Pan. Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine[J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 225-232.

Tinghao Jia, Yunbo Yu, Qing Liu, Yao Yang, Ji-Jun Zou, Xiangwen Zhang, Lun Pan. Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine[J]. 中国化学工程学报, 2023, 56(4): 225-232.

References

[1] L.M. Balster, E. Corporan, M.J. DeWitt, J.T. Edwards, J.S. Ervin, J.L. Graham, S.Y. Lee, S. Pal, D.K. Phelps, L.R. Rudnick, R.J. Santoro, H.H. Schobert, L.M. Shafer, R.C. Striebich, Z.J. West, G.R. Wilson, R. Woodward, S. Zabarnick, Development of an advanced, thermally stable, coal-based jet fuel, Fuel Process. Technol. 89 (4) (2008) 364–378.
[2] L.Q. Maurice, H. Lander, T. Edwards, W.E. Harrison III, Advanced aviation fuels: a look ahead via a historical perspective, Fuel 80 (5) (2001) 747–756.
[3] S.Y. Yuan, Z.Q. Liu, G.Z. Liu, High-gravity deoxygenation of jet fuels using rotating packed bed, Fuel 314 (2022) 123080.
[4] L.J. Spadaccini, H. Huang, On-line fuel deoxygenation for coke suppression, J. Eng. Gas Turbines Power 125 (3) (2003) 686–692.
[5] T.H. Jia, S. Gong, L. Pan, C. Deng, J.J. Zou, X.W. Zhang, Impact of deep hydrogenation on jet fuel oxidation and deposition, Fuel 264 (2020) 116843.
[6] E.G. Jones, L.M. Balster, Impact of additives on the autoxidation of a thermally stable aviation fuel, Energy Fuels 11 (3) (1997) 610–614.
[7] T.H. Jia, M.C. Zhao, L. Pan, C. Deng, J.J. Zou, X.W. Zhang, Effect of phenolic antioxidants on the thermal oxidation stability of high-energy-density fuel, Chem. Eng. Sci. 247 (2022) 117056.
[8] T. Jia, X. Zhang, Y. Liu, S. Gong, C. Deng, L. Pan, J.J.Zou, A comprehensive review of the thermal oxidation stability of jet fuels. Chem. Eng. Sci. 229 (2021) 116157.
[9] R. Shah, E.A. Haidasz, L. Valgimigli, D.A. Pratt, Unprecedented inhibition of hydrocarbon autoxidation by diarylamine radical-trapping antioxidants, J. Am. Chem. Soc. 137 (7) (2015) 2440–2443.
[10] I. de M Figueredo, M.A. de S Rios, C.L. Cavalcante Jr, F.M.T. Luna, Effects of amine and phenolic based antioxidants on the stability of babassu biodiesel using rancimat and differential scanning calorimetry techniques, Ind. Eng. Chem. Res. 59 (1) (2020) 18–24.
[11] H.N. Yuan, S.J. Yao, Y.R. You, G.N. Xiao, Q. You, Antioxidant activity of isothiocyanate extracts from broccoli, Chin. J. Chem. Eng. 18 (2) (2010) 312–321.
[12] D. Borsato, J.R. de Moraes Cini, H.C. da Silva, R.L. Coppo, K.G. Angilelli, I. Moreira, E.C.R. Maia, Oxidation kinetics of biodiesel from soybean mixed with synthetic antioxidants BHA, BHT and TBHQ: determination of activation energy, Fuel Process. Technol. 127 (2014) 111–116.
[13] J.F. Poon, D.A. Pratt, Recent insights on hydrogen atom transfer in the inhibition of hydrocarbon autoxidation, Acc. Chem. Res. 51 (9) (2018) 1996–2005.
[14] E.A. Haidasz, R. Shah, D.A. Pratt, The catalytic mechanism of diarylamine radical-trapping antioxidants, J. Am. Chem. Soc. 136 (47) (2014) 16643–16650.
[15] R.K. Jensen, S. Korcek, M. Zinbo, J.L. Gerlock. Regeneration of amine in catalytic inhibition of oxidation. J. Org. Chem.60 (1995) 5396-5400.
[16] T.A.B.M. Bolsman, A.P. Blok, J.H.G. Frijns, Catalytic inhibition of hydrocarbon autoxidation by secondary amines and nitroxides, Recueil Des Travaux Chimiques Des Pays Bas 97 (12) (1978) 310–312.
[17] S. Yu, Y. Wang, S. Wang, J.Zhu, S. Liu. The antioxidant activity and catalytic mechanism of Schiff base diphenylamines at elevated temperatures. Ind. Eng. Chem. Res. 59 (2019) 1031-1037.
[18] J.J. Hanthorn, R. Amorati, L. Valgimigli, D.A. Pratt, The reactivity of air-stable pyridine- and pyrimidine-containing diarylamine antioxidants, J. Org. Chem. 77 (16) (2012) 6895–6907.
[19] K.U. Ingold, D.A. Pratt, Advances in radical-trapping antioxidant chemistry in the 21st century: a kinetics and mechanisms perspective, Chem. Rev. 114 (18) (2014) 9022–9046.
[20] J.J. Hanthorn, L. Valgimigli, D.A. Pratt, Incorporation of ring nitrogens into diphenylamine antioxidants: striking a balance between reactivity and stability, J. Am. Chem. Soc. 134 (20) (2012) 8306–8309.
[21] ASTM. Standard Specification for Aviation Turbine Fuels, ASTM D1655. West Conshohocken, PA: ASTM International, 2018.
[22] N. Jiaorong, J. Tinghao, P. Lun, Z. Xiangwen, Z. JiJun, Development of High-Energy-Density Liquid Aerospace Fuel: A Perspective. Trans. Tianjin Univ. (2022) (1)1–5.
[23] X.W. Zhang, L. Pan, L. Wang, J.J. Zou, Review on synthesis and properties of high-energy-density liquid fuels: Hydrocarbons, nanofluids and energetic ionic liquids, Chem. Eng. Sci. 180 (2018) 95–125.
[24] G.Y. Li, B.L. Hou, A.Q. Wang, X.L. Xin, Y. Cong, X.D. Wang, N. Li, T. Zhang, Making JP-10 superfuel affordable with a lignocellulosic platform compound, Angewandte Chemie Int. Ed. 58 (35) (2019) 12154–12158.
[25] T. Jia, L. Pan, X. Wang, J. Xie, S. Gong, Y. Fang, H.Liu, X.W.Zhang, J.J.Zou, Mechanistic insights into the thermal oxidative deposition of C10 hydrocarbon fuels. Fuel 285 (2021) 119136.
[26] Q. Liu, L. Pan, T.H. Jia, X.W. Zhang, J.J. Zou, Alkyl-adamantane as high-density endothermic fuel: synthesis and thermal cracking performance, Fuel 324 (2022) 124688.
[27] T. Jia, Q. Liu, J.J. Zou, X. Zhang, L. Pan,The dynamics and mechanism of JP-10 thermal oxidative deposition, Fuel 321 (2022) 124093.
[28] Z. Haocui, X. Zhourong, Y. Mei, Z. Jijun, L. Guozhu, Z. Xiangwen, Highly dispersible cerium-oxide modified Ni/SBA-15 for steam reforming of bio-mass based JP10. Chin. J. Chem. Eng. (2022) (3)255–265.
[29] E. Klein, V. Lukeš, DFT B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of phenols antioxidant action, J. Phys. Chem. A 110 (2006) 12312-12320.
[30] S. Zabarnick, D.K. Phelps, Density functional theory calculations of the energetics and kinetics of jet fuel autoxidation reactions, Energy Fuels 20 (2) (2006) 488–497.
[31] J. Pfaendtner, L.J. Broadbelt, Elucidation of structure-reactivity relationships in hindered phenols via quantum chemistry and transition state theory, Chem. Eng. Sci. 62 (2007) 5232-5239.
[32] J.Y. Li, H.X. Liu, H.X. Yu, Z.Y. Wang, L.S. Wang, Thermodynamic properties for polybrominated dibenzothiophenes by density functional theory, Chin. J. Chem. Eng. 17 (6) (2009) 999–1008.
[33] C.M. Parks, E. Alborzi, S.G. Blakey, A.J.H.M. Meijer, M. Pourkashanian, Density functional theory calculations on copper-mediated peroxide decomposition reactions. Implications for jet fuel autoxidation, Energy Fuels 34 (2020) 7439-7447.
[34] E. Alborzi, C.M. Parks, P. Gadsby, A. Sheikhansari, S.G. Blakey, M. Pourkashanian, Effect of reactive sulfur removal by activated carbon on aviation fuel thermal stability, Energy Fuels 34 (2020) 6780-6790.
[35] L. Wang, J.J. Zou, X.W. Zhang, L. Wang, Isomerization of tetrahydrodicyclopentadiene using ionic liquid: green alternative for Jet Propellant-10 and adamantane, Fuel 91 (1) (2012) 164–169.
[36] A. Ben Amara, A. Nicolle, M. Alves-Fortunato, N. Jeuland, Toward predictive modeling of petroleum and biobased fuel stability: kinetics of methyl oleate/n-dodecane autoxidation, Energy Fuels 27 (10) (2013) 6125–6133.
[37] T. Jia, L. Pan, S. Gong, J. Xie, X. Wang, Y. Fang, J.J.Zou,X.W. Zhang, Mechanistic insights into the thermal deposition of highly thermal-stable jet fuel, Fuel 276 (2020) 118100.
[38] ASTM, Standard Test Method for Thermal Oxidation Stability of Aviation Turbine Fuels, ASTM D3241,West Conshohocken, PA: ASTM International,2014.
[39] S. Zabarnick, Z.J. West, A. Arts, M. Griesenbrock, P. Wrzesinski, Studies of the impact of fuel deoxygenation on the formation of autoxidative deposits. Energy Fuels 34 (2020) 13814-13821.
[40] S.P. Heneghan, S. Zabarnick, Oxidation of jet fuels and the formation of deposit, Fuel 73 (1) (1994) 35–43.
[41] S. Zabarnick, Chemical kinetic modeling of jet fuel autoxidation and antioxidant chemistry, Ind. Eng. Chem. Res. 32 (1993) 1012-1017.
[42] J.L. Hodgson, L.B. Roskop, M.S. Gordon, C.Y. Lin, M.L. Coote, Side reactions of nitroxide-mediated polymerization: N-O versus O-C cleavage of alkoxyamines, J. Phys. Chem. A 114 (38) (2010) 10458–10466.
[43] J. Zhou, Y. Xiong, X. Liu, Evaluation of the oxidation stability of biodiesel stabilized with antioxidants using the Rancimat and PDSC methods, Fuel 188 (2017) 61–68.
[44] F.M. Camargo, A. Della Bona, R.R. Moraes, C.R. Coutinho de Souza, L.F. Schneider. Influence of viscosity and amine content on C=C conversion and color stability of experimental composites, Dent. Mater. 31 (2015) e109-e115.

Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine

Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine

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