Alkylation of naphthalene with n-butene catalyzed by liquid coordination complexes and its lubricating properties

doi:10.1016/j.cjche.2021.01.014

Abstract

Abstract: With the development of coal chemical industry, large amounts of naphthalene and n-butene are produced, and converting them into high value-added products through alkylation has gained particular importance and interest. In this work, liquid coordination complexes (LCCs) were used as acid catalysts for the first time in the naphthalene alkylation reaction under mild conditions to obtain multi-butylnaphthalenes with high yield. Various reaction conditions were thoroughly investigated. The LCC consisting of urea and AlCl₃ showed excellent catalytic performance under optimal reaction conditions, giving 100% conversion of naphthalene and 99.66% selectivity towards multi-butylnaphthalenes. Combining the catalyst properties and catalytic results, a plausible reaction mechanism was proposed. The lubricating properties of the synthesized products were investigated for their potential application as lubricating base oils. The synthesized multi-butylnaphthalenes showed comparable physicochemical properties and tribological performances as the commercial cycloalkyl base oil.

Key words: Naphthalene, n-Butene, Alkylation reaction, Liquid coordination complexes, Synthesis, Lubricating base oils

摘要： With the development of coal chemical industry, large amounts of naphthalene and n-butene are produced, and converting them into high value-added products through alkylation has gained particular importance and interest. In this work, liquid coordination complexes (LCCs) were used as acid catalysts for the first time in the naphthalene alkylation reaction under mild conditions to obtain multi-butylnaphthalenes with high yield. Various reaction conditions were thoroughly investigated. The LCC consisting of urea and AlCl₃ showed excellent catalytic performance under optimal reaction conditions, giving 100% conversion of naphthalene and 99.66% selectivity towards multi-butylnaphthalenes. Combining the catalyst properties and catalytic results, a plausible reaction mechanism was proposed. The lubricating properties of the synthesized products were investigated for their potential application as lubricating base oils. The synthesized multi-butylnaphthalenes showed comparable physicochemical properties and tribological performances as the commercial cycloalkyl base oil.

关键词: Naphthalene, n-Butene, Alkylation reaction, Liquid coordination complexes, Synthesis, Lubricating base oils

Chen Chen, Qiong Tang, Hong Xu, Lei Liu, Mingxing Tang, Xuekuan Li, Jinxiang Dong. Alkylation of naphthalene with n-butene catalyzed by liquid coordination complexes and its lubricating properties[J]. Chinese Journal of Chemical Engineering, 2021, 39(11): 306-313.

References

[1] H.T. Guo, W.H. Qiao, J. Yang, H.M. Li, Z.S. Li, Synthesis of hexylnaphthalene, characterization of the products and the reaction mechanism, Petroleum Sci. Technol. 22(5-6) (2004) 709-718.
[2] H.T. Guo, Y. Liang, W.H. Qiao, G.R. Wang, Z.S. Li, A study on alkylation of naphthalene with long chain olefins over zeolite catalyst, Stud. Surf. Sci. Catal. 142(2002) 999-1006.
[3] M.D. Kadgaonkar, S.C. Laha, R.K. Pandey, P. Kumar, S.P. Mirajkar, R. Kumar, Cerium-containing MCM-41 materials as selective acylation and alkylation catalysts, Catal. Today 97(4) (2004) 225-231.
[4] I.I. Ivanova, A.S. Kuznetsov, E.E. Knyazeva, F. Fajula, F. Thibault-Starzyk, C. Fernandez, J.P. Gilson, Design of hierarchically structured catalysts by mordenites recrystallization:Application in naphthalene alkylation, Catal. Today 168(1) (2011) 133-139.
[5] L. Li, X.R. Zhao, C. Chen, H. Xu, L. Liu, J.X. Dong, Highly selective synthesis of polyalkylated naphthalenes catalyzed by ionic liquids and their tribological properties as lubricant base oil, ChemistrySelect 4(18) (2019) 5284-5290.
[6] J.L.G. de Almeida, M. Dufaux, Y.B. Taarit, C. Naccache, Linear alkylbenzene, J. Am. Oil Chem. Soc. 71(7) (1994) 675-694.
[7] A.M. Buchbinder, Regeneration of an acidic catalyst by alkylation of aromatic compounds, US Pat. 20150273460(2015).
[8] E.T. Hessell, R.A. Abramshe, Alkylated naphthalenes as high-performance synthetic fluids, J. Synth. Lubr. 20(2) (2003) 109-122.
[9] M.J. Hourani, T. Hessell, R.A. Abramshe, J. Liang, Alkylated naphthalenes as high-performance synthetic lubricating fluids, Tribol. Trans. 50(1) (2007) 82- 87.
[10] G.F. Mekhtieva, S.M. Musaev, Alkyl naphthalenes as lubricant and coolant process materials, Chem. Technol. Fuels Oils 41(4) (2005) 296-299.
[11] P.S. Belov, E.N. Grigor'Eva, E.M. Nikonorov, N.K. Volobuev, L.N. Sosulina, Alkylnaphthalenes as components of high-temperature lubricants, Chem. Technol. Fuels Oils 20(4) (1984) 208-210.
[12] J.M. Hogg, L.C. Brown, K. Matuszek, P. Latos, A. Chrobok, M. Swadz ′ ba-Kwas ′ny, Liquid coordination complexes of Lewis acidic metal chlorides:Lewis acidity and insights into speciation, Dalton Trans. 46(35) (2017) 11561-11574.
[13] A.P. Abbott, J.C. Barron, K.S. Ryder, D. Wilson, Eutectic-based ionic liquids with metal-containing anions and cations, Chemistry 13(22) (2007) 6495-6501.
[14] H.M. Abood, A.P. Abbott, A.D. Ballantyne, K.S. Ryder, Do all ionic liquids need organic cations? Characterisation of[AlCl₂·nAmide]+ AlCl₄(-) and comparison with imidazolium based systems, Chem. Commun. (Camb.) 47(12) (2011) 3523-3525.
[15] A.P. Abbott, R.C. Harris, Y.T. Hsieh, K.S. Ryder, I.W. Sun, Aluminium electrodeposition under ambient conditions, Phys. Chem. Chem. Phys. 16(28) (2014) 14675-14681.
[16] A.G. Suárez, AlCl₃-DMA reagent in the regioselective solvent free FriedelCrafts acylation reaction of benzodioxin derivatives, Tetrahedron Lett. 40(18) (1999) 3523-3526.
[17] S. Yous, J.H. Poupaert, I. Lesieur, P. Depreux, D. Lesieur, ChemInform abstract:AlCl₃-DMF reagent in the Friedel-Crafts reaction. Application to the acylation reaction of 2(3H)-benzothiazolones, ChemInform 25(33) (1994). https://doi. org/10.1002/chin.199433102.
[18] L. Messaoud, Y. Wassila, S. Khemissi, A. Yasmina, C. Hanane, Synthesis of some novel benzoxazolinonylcarboxamides as potential anti-inflammatory agents, J. Chem. Res. 38(6) (2014) 331-333.
[19] J.M. Hogg, F. Coleman, A. Ferrer-Ugalde, M.P. Atkins, M. Swadźba-Kwaśny, Liquid coordination complexes:A new class of Lewis acids as safer alternatives to BF₃ in synthesis of polyalphaolefins, Green Chem. 17(3) (2015) 1831-1841.
[20] J.H. Shen, F.M. Wang, T.L. Wang, H.C. Li, G. Wang, X.B. Zhang, Sulfination of acetanilide using liquid coordination complexes as dual catalyst and solvent, Mol. Catal. 462(2019) 56-60.
[21] P.C. Hu, J.W. Zheng, W. Jiang, L.J. Zhong, S.F. Zhou, Isomerization of n-pentane catalyzed by amide-AlCl₃-based ionic liquid analogs with various additives, Chin. J. Chem. Eng. 28(1) (2020) 152-157.
[22] K. Matuszek, A. Chrobok, J.M. Hogg, F. Coleman, M. Swadźba-Kwaśny, FriedelCrafts alkylation catalysed by GaCl₃-based liquid coordination complexes, Green Chem. 17(8) (2015) 4255-4262.
[23] P.C. Hu, Y.D. Wang, X.H. Meng, R. Zhang, H.Y. Liu, C.M. Xu, Z.C. Liu, Isobutane alkylation with 2-butene catalyzed by amide-AlCl₃-based ionic liquid analogues, Fuel 189(2017) 203-209.
[24] Y.L. Yang, Y. Kou, Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe, Chem. Commun. Camb. 2(2004) 226-227.
[25] F. Coleman, G. Srinivasan, M. Swadźba-Kwaśny, Liquid coordination complexes formed by the heterolytic cleavage of metal halides, Angew. Chem. Int. Ed. Engl. 52(48) (2013) 12582-12586.
[26] R. Kore, P. Berton, S.P. Kelley, P. Aduri, S.S. Katti, R.D. Rogers, Group IIIA halometallate ionic liquids:Speciation and applications in catalysis, ACS Catal. 7(10) (2017) 7014-7028.
[27] P.C. Hu, R. Zhang, X.H. Meng, H.Y. Liu, C.M. Xu, Z.C. Liu, Structural and spectroscopic characterizations of amide-AlCl₃-based ionic liquid analogues, Inorg. Chem. 55(5) (2016) 2374-2380.
[28] M. Malik, K.L. Ng. B, G. Azimi, Physicochemical characterization of AlCl₃-urea ionic liquid analogs:Speciation, conductivity, and electrochemical stability, Electrochim. Acta. 354(2020) 136708.
[29] G.P. Qi, F. Jiang, X.W. Sun, S.Q. Zhao, Alkylation mechanism of benzene with 1- dodecene catalyzed by Et₃NHCl-AlCl₃, Ence China Chem. 53(2010) 1102-1107.