remove. Elomari et al. describe a number of potential approaches for regeneration
(Elomari and Harris 2010).
If these critical issues are addressed, ionic liquid alkylation shows great promise as
an alternative to traditional liquid acid alkylation technologies. Chevron, Shell/CUP,
and UOP are all actively developing commercial ionic liquid alkylation processes.
References
Anon, Hydrofluoric Acid Alkylation (The Phillips Petroleum Company, 1946)
S. Aschauer et al., Liquid-phase isobutane/butene alkylation using promoted Lewis-acidic
IL-catalysts. Catal. Lett. 141(10), 1405–1419 (2011)
T. Chou et al., World Patent WO 90/00534, (1990a)
T. Chou et al., World Patent WO 90/00533, (1990b)
A. Corma, A. Orchilles, Microp. Mesop. Mater. 35–36, 21 (2000)
A. de Angelis et al., Catal. Today 65, 363 (2001)
S. Elomari, T. Harris, Chevron USA, U.S. Patent 7,732,363, (2010)
S. Elomari et al., Chevron USA, U.S. Patent 7,432,409, (2008)
J. Gieseman, V. Amico, E. van Broekhoven, The Alkyclean
TM Alkylation Process: New Technology Eliminates Liquid Acids. Paper AM-06-41 at NPRA 2006 annual meeting, Salt Lake City,
19–21 Mar 2006
T. Harris et al., Chevron USA, U.S. Patent 7,531,707, (2009)
J.H.D. Hooper, Chem. Ind. 20, 683 (1986)
C.P. Huang et al., Effects of additives on the properties of chloroaluminate ionic liquids catalyst
for alkylation of isobutane and butene. Appl. Catal. A Gen. 277(1–2), 41–43 (2004)
A. Huss Jr., I.D. Johnson, U.S. Patent 5,221,777, (1993)
V.M. Ipatieff, A.V. Grosse, J. Am. Chem. Soc. 37, 1616 (1935)
E.C. Jernigan, J.E. Gwyn, E.L. Claridge, Chem. Eng. Prog. 61(11), 94 (1965)
M. Kojima, J. Kocal, U.S. Patent 5,391,527, (1995)
C. Lacroix et al., Akzo, U. S. Patent 5,731,101, (1998)
Z. Liu et al., China University of Petroleum, Beijing, “Reaction performance of isobutane alkylation
catalyzed by a composite Ionic liquid at short contact time”. AIChE J. 60(6), 2244–2253 (2014)
P. Nascimento et al., U.S. Patent 6,225,517, (2001)
G.S. Nivarthy et al., Microp. Mesop. Mater. 22, 379 (1998)
H. Olivier-Bourbigou et al., IFP, U.S. Patent 7,256,152, (2002)
H. Pines, ChemTech. 150 March (1982)
C.M. Roeseler, D.J. Shields, S.M. Black, C.D. Gosling, Improved Solid Catalyst Alkylation
Technology for Clean Fuels: The Alkylene Process. Paper at the NPRA annual meeting, San
Antonio, 17–19 Mar 2002
C.C. Sadler, U.S. Patent 8,373,014, 2013
L. Schilder et al., Effective and intrinsic kinetics of liquid-phase Isobutane/2-Butene alkylation
catalyzed by chloroaluminate Ionic liquids. Ind. Eng. Chem. Res. 52, 1877–1885 (2013)
K.R.J. Seddon, Chem. Tech. Biotech. 68, 351–356 (1997)
F.B. Sprow, Ind. Eng. Chem. Process Des. Dev. 8(2), 254 (1969)
M. Stocker et al., Catal. Lett. 28, 203 (1994)
H. Timken et al., Chevron USA, Patent 7,432,408, (2008)
P. Wasserscheid, W. Keim, Ionic liquids – new solutions for transition metal catalysis. Angew.
Chem. Int. Ed. 39, 3772–3789 (2000)
J. Weitkamp, Stud. Surf. Sci. Catal. 5, 65 (1980)
T. Welton, Room temperature Ionic liquids. Solvents for synthesis and catalysis. Chem. Rev.
99, 2071–2083 (1999)
456
D.A. Nafis et al.
(Elomari and Harris 2010).
If these critical issues are addressed, ionic liquid alkylation shows great promise as
an alternative to traditional liquid acid alkylation technologies. Chevron, Shell/CUP,
and UOP are all actively developing commercial ionic liquid alkylation processes.
References
Anon, Hydrofluoric Acid Alkylation (The Phillips Petroleum Company, 1946)
S. Aschauer et al., Liquid-phase isobutane/butene alkylation using promoted Lewis-acidic
IL-catalysts. Catal. Lett. 141(10), 1405–1419 (2011)
T. Chou et al., World Patent WO 90/00534, (1990a)
T. Chou et al., World Patent WO 90/00533, (1990b)
A. Corma, A. Orchilles, Microp. Mesop. Mater. 35–36, 21 (2000)
A. de Angelis et al., Catal. Today 65, 363 (2001)
S. Elomari, T. Harris, Chevron USA, U.S. Patent 7,732,363, (2010)
S. Elomari et al., Chevron USA, U.S. Patent 7,432,409, (2008)
J. Gieseman, V. Amico, E. van Broekhoven, The Alkyclean
TM Alkylation Process: New Technology Eliminates Liquid Acids. Paper AM-06-41 at NPRA 2006 annual meeting, Salt Lake City,
19–21 Mar 2006
T. Harris et al., Chevron USA, U.S. Patent 7,531,707, (2009)
J.H.D. Hooper, Chem. Ind. 20, 683 (1986)
C.P. Huang et al., Effects of additives on the properties of chloroaluminate ionic liquids catalyst
for alkylation of isobutane and butene. Appl. Catal. A Gen. 277(1–2), 41–43 (2004)
A. Huss Jr., I.D. Johnson, U.S. Patent 5,221,777, (1993)
V.M. Ipatieff, A.V. Grosse, J. Am. Chem. Soc. 37, 1616 (1935)
E.C. Jernigan, J.E. Gwyn, E.L. Claridge, Chem. Eng. Prog. 61(11), 94 (1965)
M. Kojima, J. Kocal, U.S. Patent 5,391,527, (1995)
C. Lacroix et al., Akzo, U. S. Patent 5,731,101, (1998)
Z. Liu et al., China University of Petroleum, Beijing, “Reaction performance of isobutane alkylation
catalyzed by a composite Ionic liquid at short contact time”. AIChE J. 60(6), 2244–2253 (2014)
P. Nascimento et al., U.S. Patent 6,225,517, (2001)
G.S. Nivarthy et al., Microp. Mesop. Mater. 22, 379 (1998)
H. Olivier-Bourbigou et al., IFP, U.S. Patent 7,256,152, (2002)
H. Pines, ChemTech. 150 March (1982)
C.M. Roeseler, D.J. Shields, S.M. Black, C.D. Gosling, Improved Solid Catalyst Alkylation
Technology for Clean Fuels: The Alkylene Process. Paper at the NPRA annual meeting, San
Antonio, 17–19 Mar 2002
C.C. Sadler, U.S. Patent 8,373,014, 2013
L. Schilder et al., Effective and intrinsic kinetics of liquid-phase Isobutane/2-Butene alkylation
catalyzed by chloroaluminate Ionic liquids. Ind. Eng. Chem. Res. 52, 1877–1885 (2013)
K.R.J. Seddon, Chem. Tech. Biotech. 68, 351–356 (1997)
F.B. Sprow, Ind. Eng. Chem. Process Des. Dev. 8(2), 254 (1969)
M. Stocker et al., Catal. Lett. 28, 203 (1994)
H. Timken et al., Chevron USA, Patent 7,432,408, (2008)
P. Wasserscheid, W. Keim, Ionic liquids – new solutions for transition metal catalysis. Angew.
Chem. Int. Ed. 39, 3772–3789 (2000)
J. Weitkamp, Stud. Surf. Sci. Catal. 5, 65 (1980)
T. Welton, Room temperature Ionic liquids. Solvents for synthesis and catalysis. Chem. Rev.
99, 2071–2083 (1999)
456
D.A. Nafis et al.