Citation: LIU Ying, SUN Hong-juan, CONG Ying-nan, HU Rui-sheng. Study on the selectivity of isobutane/2-butene alkylation catalyzed by ionic liquid with Cu compound[J]. Journal of Fuel Chemistry and Technology, ;2014, 42(8): 1010-1016. shu

Study on the selectivity of isobutane/2-butene alkylation catalyzed by ionic liquid with Cu compound

1.
School of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China

Corresponding author: LIU Ying,
Received Date: 21 March 2014
Available Online: 10 June 2014
Fund Project: 国家自然科学基金(21266015)。 (21266015)

The Cu-containing ionic liquids (IL), like [BMIm]Cl-1.8AlCl₃-0.5CuCl and [Et₃NH]Cl-1.8AlCl₃/ CuAlCl₄, were synthesized and characterized. The selectivity of isobutene/butene alkylation of Cu-containing IL was also investigated. The results showed that the selectivity had little relation to the acidity of Cu-containing IL. The research octane number (RON) of [Et₃NH]Cl-1.8AlCl₃/CuAlCl₄ alkylate could be higher than 100, which was better than those obtained by sulfuric acid, common chloroaluminate IL, and composite IL under the identical reaction conditions. The complexation of CuAlCl₄ with 2-butene in alkylation process should be accounted for the super selectivity of trimethylpentane (TMP) of isobutane alkylation catalyzed by Cu-containing IL.
- ionic liquid,
- isobutane,
- alkylation,
- selectivity
1. [1]
  [1] SCHILDER L, MAASS S, JESS A. Effective and intrinsic kinetics of liquid-phase isobutane/2-butene alkylation catalyzed by chloroaluminate ionic liquids[J]. Ind Eng Chem Res, 2013, 52(5): 1877-1885.
2. [2]
  [2] CORMA A, MARTINEZ A. Chemistry, catalysts and processes for isoparaffin-olefin alkylation[J]. Catal Rev: Sci Eng, 1993, 35(4): 483-570.
3. [3]
  [3] XING X Q, ZHAO G Y, CUI J Z, ZHANG S J. Isobutane alkylation using acidic ionic liquid catalysts[J]. Catal Commun, 2012, 26: 68-71.
4. [4]
  [4] ZHANG Z C. Catalysis in ionic liquids[J]. Adv Catal, 2006, 49: 153-237.
5. [5]
  [5] LIU Y, HU R, XU C, SUA H. Alkylation of isobutene with 2-butene using composite ionic liquid catalysts[J]. Appl Catal A: Gen, 2008, 346(1/2): 189-193.
6. [6]
  [6] OLIVIER-BOURBIGOU H, MAGNA L, MORVAN D. Ionic liquids and catalysis: Recent progress from knowledge to applications[J]. Appl Catal A: Gen, 2010, 373(1/2): 1-56.
7. [7]
  [7] OLAH G A, BATAMACK P, DEFFIEUX D, T R K B, WANG Q, MOLN R Á, PRAKASH G K S. Acidity dependence of the trifluoromenthaneulfonic acid catalyzed isobutane-isobutylene alkylation modified with trifluoroacetic acid or water[J]. Appl Catal A: Gen, 1996, 146(1): 107-117.
8. [8]
  [8] ALBRIGHT L F. Alkylation of isobutane with C₃-C₅ olefins to produce high-quality gasolines-physicochemical sequence of events[J]. Ind Eng Chem Res, 2003, 42(19): 4283-4289.
9. [9]
  [9] THI L T B, KORTH W, JESS A. Influence of acidity of modified chloroaluminate based ionic liquid catalysts on alkylation of iso-butene with butene-2[J]. Catal Commun, 2012, 25: 118-124.
10. [10]
  [10] ZHANG J, HUANG C P, CHEN B H, REN P J, PU M. Isobutane/2-butene alkylation catalyzed by chloroaluminate ionic liquids in the presence of aromatic additives[J]. J Catal, 2007, 249(2): 261-268.
11. [11]
  [11] YANG Y L, KOU Y. Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe[J]. Chem Commun, 2004, (2): 226-227.
12. [12]
  [12] HUANG C P, LIU Z C, XU C M, CHEN B, LIU Y F. Effects of additives on the properties of chloroaluminate ionic liquids catalyst for alkylation of isobutane and butene[J]. Appl Catal A: Gen, 2004, 277(1/2): 41-43.
13. [13]
  [13] ROEBUCK A K, EVERING B L. Isobutane-olefin alkylation with inhibited aluminum chloride catalysts[J]. Ind Eng Chem Prod Res Dev, 1970, 9(1): 76-82.
14. [14]
  [14] SULLIVAN R M, LIU H, SMITH D S, HANSON J C, OSTERHOUT D, CIRAOLO M, GREY C P, MARTIN J D. Sorptive reconstruction of the CuAlCl4 Framework upon reversible ethylene binding[J]. J Am Chem Soc, 2003, 125(36): 11065-11079.
15. [15]
  [15] MARTIN J D, LEAFBLAD B R, SULLIVAN R M, BOYLE P D. SymbolaA@-and SymbolbA@-CuAlCl₄: Framework construction using corner-shared tetrahedral metal-halide building blocks[J]. Inorg Chem, 1998, 37(6): 1341-1346.
16. [16]
  [16] THI L T B, KORTH W, ASCHAUERB S, JESSB A. Alkylation of isobutane with 2-butene using ionic liquids as catalyst[J]. Green Chem, 2009, 11(12): 1961-1967.
17. [17]
  [17] WILKES J S, FRYE J S, REYNOLDS G F. Aluminum-27 and carbon-13 NMR studies of aluminum chloride-dialkylimidazolium chloride molten salts[J]. Inorg Chem, 1983, 22(26): 3870-3872.
18. [18]
  [18] GRAY J L, MACIEL G E. Aluminum-27 nuclear magnetic resonance study of the room-temperature melt aluminum trichloride butylpyridinium chloride[J]. J Am Chem Soc, 1981, 103(24): 7147-7151.
19. [19]
  [19] 刘植昌, 张睿, 刘鹰, 徐春明. 复合离子液体催化碳四烷基化反应性的研究[J]. 燃料化学学报, 2006, 34(3): 328-331. (LIU Zhi-Chang, ZHANG Rui, LIU Ying, XU Chun-Ming. Study on isobutane alkylation catalyzed by composite ionic liquid[J]. Journal of Fuel Chemistry and Technology, 2006, 34(3): 328-331.)
20. [20]
  [20] SAFARIK D J, ELDRIDGE R B. Olefin/paraffin separations by reactive absorption: A review[J]. Ind Eng Chem Res, 1998, 37(7): 2571-2581.
21. [21]
  [21] OLAH G A, MATHEW T, GOEPPERT A, TOROK B, BUCSI I, LI X Y, WANG Q, MARINEZ E R, BATAMACK P, ANISZFELD R, PRAKASH G K. Ionic liquid and solid HF equivalent amine-poly(hydrogen fluoride) complexes effecting efficient environmentally friendly isobutane-isobutylene alkylation[J]. J Am Chem Soc, 2005, 127(16): 5964-5969.
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沈阳化工大学材料科学与工程学院沈阳 110142