Benzene alkylation with long chain olefins catalyzed by ionic liquids: a review

Abstract

The introduction of ionic liquids to alkylation process gives a choice for “green production” in the petrochemical and detergent industry. A lot of papers and patents have been published using chloroaluminate ionic liquid as a novel catalyst for alkylation with high reactivity and easy separation from reactants. These included the acidity, characterization, determination and catalysis technologies in batch and continuous operation mode for different scales. According to published data and several results of pilot alkylation,including the authors’ experience,the prospect of chloroaluminate ionic liquids for commercials was also discussed. It has been pointed out that there still are many difficulties and challenges to be overcome for commercial application of the ionic liquid catalyst.

References

1. Almeida J L G, Dufaux M, Taarit Y B . Linear alkylbenzene. JAOCS, 1994, 71: 675–694. doi:10.1007/BF02541423
2. Kocal J A, Vora B V, Imai T . Production of linear alkylbenzenes. Applied Catalysis A: General, 2001, 221: 295–300. doi:10.1016/S0926‐860X(01)00808‐0
3. Wilkes J S, Levisky J A, Wilson R A, Charles L H . Dialkylimidazolium chloroaluminate melts: a new class of room-temperatureionic liquids for electrochemistry, spectroscopy, and Synthesis. Inorg Chem, 1982, 21: 1263–1264. doi:10.1021/ic00133a078
4. Boon J A, Levisky J A, Pflug J L, Wilkes J S . Friedel-Craftsreaction in ambient temperature molten salts. J Org Chem, 1986, 51: 480–483. doi:10.1021/jo00354a013
5. De Castro C, Sauvage E, Valkenburg M H, HÖlderich W F . Immobilised ionic liquids as Lewis acid catalysts for the alkylationof aromatic compounds with dodecene. JCatal, 2000, 196: 86–94. doi:10.1006/jcat.2000.3004
6. Qiao K, Deng Y . Alkylations of benzene inroom temperature ionic liquids modified with HCl. J Mole Catal, 2001, 171: 81–84. doi:10.1016/S1381‐1169(01)00107‐8
7. Sherif F G, Shyu L J . Linear alkylbenzene formationusing low temperature ionic liquid. US Patent, 5824832,1998
8. Sherif F G, Shyu L J . Alkylation reaction usingsupported ionic liquid catalyst. World Patent, 9903163,1999
9. Steichen D S, Shyu L J . In-situ formation of ionicliquid catalyst for an ionic liquid catalyzed chemical reaction. World Patent, 9850153, 1998
10. Keim W, Korth W, Wasserscheid P . Ionic liquid. World Patent, 0016902, 2000
11. Song C E, Shim W H, Roh E J, Choi J H . Scandium(III)triflate immobiled in ionic liquid: a novel and recyclable catalyticsystem for Friedel-Crafts alkylation of aromatic commpounds with alkenes. Chem Commun, 2000: 1695–1696
12. Freemantle M . Designersolvent-Ionic liquids may boost clean technology development. Chemical and Engineering News, 1998, 30(3): 32–34
13. Welton T . Roomtemperature ionic liquids solvent for synthesis and catalysis. Chem Rev 1999, 99: 2071–2083. doi:10.1021/cr980032t
14. Holbrey J D, Seddon K R . Ionic liquids. Clean Prod Process. 1999, 1: 223–236
15. Adams C J, Earle M J, Roberts G, Seddon K R . Friedel-Craftsreaction in room temperature ionic liquids. Chem Commun, 1998: 2097–2098.
16. Stark A, MacLean B L, Singer R D . 1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquidsas solvents for Friedel-Crafts acylation reactions of ferrocene. J Chem Soc, Dalton Trans, 1999: 63–64
17. Surette J K D, Green L, Singer R D . 1-Ethyl-3-methylimidazolium halogenoaluminate melts asreaction media for the Friedel-Crafts acylation of ferrocene. Chem Commun,1996: 2753–2754
18. Green L, Hemeon I, Singer R D . 1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquidsas reaction media for the acylative cleavage of ethers. Tetrahedron Letters, 2000: 1343–1346
19. Stenzel1 O, Brüll R, Wahner U M, Sanderson R D, Raubenheimer H G . Oligomerization of olefinsin a chloroaluminate ionic liquid. Journalof Molecular Catalysis A: Chemical, 2003, 192: 217–222. doi:10.1016/S1381‐1169(02)00450‐8
20. Chauvin Y, Olivier H, Wyrvalskiy C N, Simony L C, De Souzay R F . Oligomerization of n-butenes catalyzed by nickel complexes dissolvedin organochloroaluminate ionic liquids. J Catal, 1997, 165: 275–278. doi:10.1006/jcat.1997.1488
21. Gu Y, Shi F, Deng Y . SO₃H-functionalized ionic liquidas efficient, green and reusable acidic catalyst system for oligomerizationof olefins. Catalysis Communications, 2003, 4: 597–601. doi:10.1016/j.catcom.2003.09.004
22. Bernardo-Gusmão K, Queiroz L F T, De Souza R F, Leca F, Loup C, Reau R . Biphasicoligomerization of ethylene with nickel-1,2-diiminophosphorane complexesimmobilized in 1-n-butyl-3-methylimidazoliumorganochloroaluminate. J Catal, 219(2003): 59–62
23. Qiao K, Deng Y . A novel reaction in ionicliquids: selective cyclization of 1-dodecene to cyclododecane undermoderate pressure. Tetrahedron Letters, 2003, 44: 2191–2193. doi:10.1016/S0040‐4039(03)00158‐8
24. Kumar A, Pawar S S . AlCl₃-catalysed dimerization of 1,3-cyclopentadiene in the chloroaluminateroom temperature ionic liquid. J Mole CatalA: Chemical, 2004, 208: 33–37. doi:10.1016/S1381‐1169(03)00510‐7
25. Kumar A, Pawar S S . The DABCO-catalysed Baylis–Hillmanreactions in the chloroaluminate room temperature ionic liquids: ratepromoting and recyclable media. J MoleCatal A: Chemical, 2004, 211: 43–47. doi:10.1016/j.molcata.2003.10.002
26. Gu Y, Shi F, Deng Y . Esterification of aliphatic acids with olefin promotedby Brønsted acidic ionic liquids. J Mole Catal, 2004, 212: 71–75. doi:10.1016/j.molcata.2003.10.039
27. Kamal A, Chouhan G . Chemoselective thioacetalizationand transthioacetalization of carbonyl compounds catalyzed by immobilizedscandium(III) triflate in ionic liquids. Tetrahedron Letters, 2003, 44: 3337–3340. doi:10.1016/S0040‐4039(03)00580‐X
28. Wang X . Synthesisof linear alkylbenzene catalysed by ionic liquid. Advances in fine petrochemicals. 2005, 6(2): 34–37(in Chinese)
29. Xin H, Wu Q, Han M, Wang D, Jin Y . Alkylation of benzene with 1-dodecene in ionic liquids[Rmim]⁺Al₂Cl₆X^- (R = butyl, octyl anddodecyl; X = chlorine, bromine and iodine). Applied Catalysis A: General, 2005, 292(18): 354–361
30. Zhao D, Kou Y . Room temperature ionic liquid-synthesis,property and application. Chemistry ofUniversity, 2002, 17(1): 42–46 (in Chinese)
31. Yang Y, Kou Y . Determination of the Lewisacidity of ionic liquids by means of an IR spectroscopic probe. Chem Commun, 2004, 2: 226–227. doi:10.1039/b311615h
32. Piao L Y, Fu X, Yang Y L, Tao G H, Kou Y . Alkylation of diphenyl oxide with a-dodecene catalyzedby ionic liquids. Catalysis Today, 2004, 93–95: 301–305. doi:10.1016/j.cattod.2004.06.135
33. Thomazeau C, Olivier-Bourbigou H, Magna L . Determination of an acidic scale in roomtemperature ionic liquids. J Am Chem Soc, 2003, 125(18): 5264–5265. doi:10.1021/ja0297382
34. Dong B, Wu Q, Han M, Xin H . Alkylationof benzene with C16–C18 olefins catalyzed by [Bmim]Cl/AlCl₃ ionic liquid. The ChineseJournal of Process Engineering, 2007, 7(1): 59–62 (in Chinese)
35. Wu Q, Dong B, Han M, Xin H, Zuo Y, Jin Y . Studies onacidity of chloroaluminate ionic liquids and its catalytic performancefor alkylation of benzene with long-chain alkenes. Spectroscopy and Spectral Analysis, 2007, 27(13): 460–464 (in Chinese)
36. Zhu H, Cao Z, Wu R, Mu X . Synthesis oflinear alkylbenzene catalysed by chloroaluminate ionic liquid. Advances in fine petrochemicals, 2007, 8(2): 1–4 (in Chinese)
37. Dong B, Wu Q, Han M, Xin H . Alkylationof benzene with C16–C18 olefins catalyzed by [Bmim]Cl/AlCl₃ ionic liquid. The ChineseJournal of Process Engineering, 2007, 7(1): 59–62 (in Chinese)
38. Xi L, Peng P, Duan Q, Lu W . Continuousprocess of arene alkylation over ionic liquid catalyst. Petrochemical Technology, 2005, 34(8): 725–728 (in Chinese)
39. Qiao C, Li C, Zhang J, Zhang Y . Activity andstability investigation of [BMIM][AlCl₄] ionicliquid as catalyst for alkylation of benzene with 1-dodecene. Applied Catalysis A: General, 2004, 276/1–2: 61–66. doi:10.1016/j.apcata.2004.07.021
40. Qiao C, Li C, Chen B, Tian X . Recycling set-upfor alkylation of benzene with 1-dodecene catalysed by ionic liquid. Chinese Journal of Chemical Engineering and industry, 2004, 55(12): 2038–2042 (in Chinese)
41. Lemenand T, Valle D D, Zellouf Y, Peerhossaini H . Dropletsformation in turbulent mixing of two immiscible fluids in a new typeof static mixer. International Journalof Multiphase Flow, 2003, 29, 813–840. doi:10.1016/S0301‐9322(03)00032‐6
42. Fang J Z, Lee D J . Micromixing efficiency instatic mixer. Chem Eng Sci, 2001, 56: 3797–3802. doi:10.1016/S0009‐2509(01)00098‐7
43. Qiao C, Li C . Continuous reaction performancesof benzene alkylation with long chain olefins catalyzed by ionic liquid. Chemical Reaction Engineering and Technology, 2006, 22(4): 289–293 (in Chinese)
44. Zawodzinki T A, Osteryoung R A . Oxide and hydroxide speciesformed on addition of water in ambient-temperature chloroaluminatemelts: An ¹⁷O NMR study. Inorg Chem, 1990, 29, 2842–2847. doi:10.1021/ic00340a024
45. Qiao C, Li C . Recycling and activity recoveryof chloroaluminate ionic liquid as catalyst for the alkylation ofbenzene with 1-dodecene. Chinese Journalof Process Engineering, 2006, 6(2): 302–307