Paper Titles

Hydrotalcites as Catalysts and Catalysts Precursors for the Synthesis of Biodiesel
p.1

Additives for Solid Polymer Electrolytes: The Layered Nanoparticles
p.27

Adsorption of Acid Dyes on Hydrotalcite-Like Anionic Clays
p.57

Pillared Clay as an Effective Catalyst for Low Temperature VOCs Decomposition
p.71

Recent Development in Clay Based Functional Coating for Corrosion Protection
p.93

The Layered Silicate, Montmorillonite (MMT) as a Drug Delivery Carrier
p.111

Drug Delivery Using Nanosized Layered Double Hydroxide, an Anionic Clay
p.133

Progress in One-Pot Synthesis of Methyl Isobutyl Ketone Using Multifunctional Layered Based Catalysts
p.169

Layered Clay Rubber Composites
p.197

HomeKey Engineering MaterialsKey Engineering Materials Vol. 571Progress in One-Pot Synthesis of Methyl Isobutyl...

Progress in One-Pot Synthesis of Methyl Isobutyl Ketone Using Multifunctional Layered Based Catalysts

Article Preview

Abstract:

Methyl isobutyl ketone (MIBK) is one of the most widely produced and used aliphatic ketones worldwide. The one-step MIBK process with no intermediate separation steps using multifunctional catalysts is an important development towards greener organic synthesis and generates tremendous interest among the researcher across the globe. The single step process is facile and more economically viable and has provided opportunity to develop new and improved catalyst systems capable of operating under mild conditions. A widely variety of catalytic systems have been used in one-step process during last three to four decades. The progress in one-pot synthesis of MIBK using different multifunctional catalysts with special reference to layered based catalysts was critically reviewed in this article.

You might also be interested in these eBooks

Layered Clay Materials for Functional Applications

Info:

Periodical:

Key Engineering Materials (Volume 571)

Pages:

169-196

DOI:

https://doi.org/10.4028/www.scientific.net/KEM.571.169

Citation:

Cite this paper

Online since:

July 2013

Authors:

Nigamananda Das

Keywords:

Catalyst, Green Synthesis, Hydrotalcite, Methyl Isobutyl Ketone

Export:

RIS, BibTeX

Price:

Permissions:

Request Permissions

[1] K. Weissermel, H.-J. Arpe, Industrial Organic Chemistry, 4th ed., Wiley-VCH, Weinheim, 2003, p.282.

[2] Ullmann's Encyclopedia of Industrial Chemistry, 6th ed., in CD ROM, 2002.

[3] Y. Onoue, Y. Mizutani, S. Akiyama, Y. Izumi, Y. Watanabe, CHEMTEC (1977) 36.

[4] J. Braithwaite, in "Kirk-Othmer Encyclopedia of Chemical Technology" (J. I. Kroschwitz and M. Howe-Grant, Eds.), Wiley, New York, 4th ed., Vol. 14, 1995, p.989.

[5] W. Reith, M. Dettmer, H. Widdecke, B. Fleischer, Stud. Surf. Sci. Catal. 59 (1991) 487; ibid, in: M. Guisnet, et al. (Eds.), Heterogeneous Catalysis and Fine Chemicals II, Elsevier, Amsterdam, 1991.

DOI: 10.1016/s0167-2991(08)61157-x

[6] S. Wilde, D. Sommer, Petroleum Technol. Q. (Spring) (1998) 127.

[7] (a) J. Hoffman, Chemical Market Reporter, 3 February 2003; http://www.sasol.com/ Posted 19th December 2005. (b) Chemical Insight & Forecasting: IHS Chemical, February 2012.

[8] J. I. Di Cosimo, G. Torres and C. R. Apestegu´ıa, One-Step MIBK Synthesis: A New Process from 2-Propanol, J. Catal. 208 (2002) 114–123.

DOI: 10.1006/jcat.2002.3551

[9] G. J. Kelly, F. King, Waste Elimination in Condensation Reactions of Industrial Importance, Green Chem. 4 (2002) 392.

DOI: 10.1039/b201982p

[10] M.J. Climent, A. Corma, S. Iborra, Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals, Chem. Rev., 111 (2011) 1072–1133.

DOI: 10.1021/cr1002084

[11] P.M. Lange, F. Martinola, S. Oecki, Use of bifunctional catalysts for MTBE, TAME and MIBK, Hydrocarb. Process. Des. (1995) 51–52.

[12] (a) T. J. Pinnavaia, "Nonporous layered materials," Advances in Chemistry, vol. 245, 1995, p.283–300. (b) G. Centi, S. Perathoner, Catalysis by layered materials: A review, Micropor. Mesopor. Mater. 107 (2008) 3.

[13] (a) F. Cavani, F. Trifirò, A. Vaccari, Hydrotalcite type anionic clay: Preparation, properties and applications, Catal. Today, 11 (1991) 173. (b) V. Rives, (Ed.), Layered Double Hydroxides. Present and Future, Nova Science Publisher, Inc., New York (2001). (c) F. Basile, A. Vaccari, In: Rives, V. (Ed.), Layered Double Hydroxides: Present and Future, Nova Science Publishers, Inc., New York, (2001) 285. (d) E. Wypych, K.G. Satyanarayana, (Eds.), Clay Surfaces Fundamentals and Applications, Elsevier, Amsterdam, (2004). (e) F. Li, X. Duan, In: D.M.P. Mingos, (Ed.), Layered Doubled Hydroxides. Structure and Bonding. Springer-Verlag, Berlin, (2006) 193. (f) C. del Hoyo, Layered double hydroxides and human health: An overview, Appl. Clay Sci. 36 (2007) 103. (g) F. Zhang, X. Xiang, F. Li, X. Duan, Layered Double Hydroxides as Catalytic Materials: Recent Development, Catal. Surv. Asia, 12 (2008) 253. (h) Z.P. Xu, J. Zhang, M.O. Adebajo, H. Zhang, C. Zhou, Catalytic applications of layered double hydroxides and derivatives, Appl. Clay Sci. 53 (2011) 139.

[14] (a) T.H. Bennur, A. Ramani, R. Bal, B.M. Chanda, S. Sivasanker, Palladium(II) containing hydrotalcite as an efficient heterogeneous catalyst for Heck reactions, Catal. Commun. 3 (2002) 493–496. (b) B.M. Choudary, S. Madhi, N.S. Chowdari, L.M. Kantam, B. Sreedhar,, Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-and Stille-type coupling reactions of chloroarenes. J. Am. Chem. Soc. 124 (2002) 14127–14136. (c) Y.Z. Chen, C.M. Hwang, C.W. Liaw, One-step synthesis of methyl isobutyl ketone from acetone with calcined Mg/Al hydrotalcite-supported palladium or nickel catalysts. Appl. Catal. A Gen. 169 (1998) 207–214.

DOI: 10.1021/ja026975w

[15] Deutsche Texaco, US Patent 3,405,178 (1968), Wollner, J., and Moers, K. K.) and US Patent 3,574,763 (1971)

[16] Veba-Chemie, DE Patent 1,643,044 (1972)

[17] K. Schmitt, J. Distedorf, W. Flakus, Process for Preparing Methyl Isobutyl Ketone and Catalyst, US Patent 3,953,517; (1976).

[18] Distillers, Co., Br. Patent 1,015,003 (1965).

[19] D. Muthusamy, I. Fisher in "Methyl Isobutyl Ketone", Kirk-Othmer Encyclopedia of Chemical Technology, J. Wiley & Sons, Inc. (2001).

DOI: 10.1002/0471238961.1305200813212008.a01

[20] (a) S. Wilde, D. Sommer, Production of high purity MIBK, Petrochemicals, Spring (1998) 127–131. (b) H.F. Rase, Handbook of Commercial Catalysts Heterogeneous Catalysts; CRC press: Boca Raton, FL, 2000.

[21] Y. Too, T. Nakayama, JP62258335 (1987).

[22] T. Maki, T. Yokoyama, Y. Sumino, JP63068538 (1988).

[23] T. Maki, T. Yokoyama, Y. Sumino, JP63096146 (1988).

[24] T. Ushikubo, Y. Kakuno, H. Tsujiura, EP458216 (1991).

[25] T. Maki, T. Yokoyama, Y. Sumino JP63096147 (1988).

[26] T. Maki, T. Yokoyama, Y. Sumino, JP63068539 (1988).

[27] H. Chin, K. Shu, Y. Chin, N. Cho, B. Hayashi, S. So, JP02069430 (1990).

[28] Y. Too, T. Nakayama, K. Shioda, JP03093743 (1991).

[29] T. Ushikubo, Y. Kakuno, H. Tsujiura, EP458216 (1991).

[30] L. Chu, Z. Yao, CN1069674 (1993).

[31] P. Chen, S. Chu, K. Wu, W. Lin, US Patent 5684207 (1997).

[32] Y. Higashio, K. Hamada, EP87-308156 (1987).

[33] D. Bombos, G. Bozga, M. Bombos, A. Stefan, I. Stanciu, Chem. Papers 54 (2000) 171–176.

[34] S. Yang, Y. Wu, One step synthesis of methyl isobutyl ketone over palladium supported on AlPO4-11 and SAPO-1, Appl. Catal. A: Gen. 192 (2000) 211–220.

DOI: 10.1016/s0926-860x(99)00408-1

[35] Y. Higashio, T. Nakayama, One-step synthesis of methyl isobutyl ketone catalyzed by palladium supported on niobic acid, Catal. Today 28 (1996) L27- L31.

DOI: 10.1016/0920-5861(95)00219-7

[36] Y.Z. Chen, B.J. Liaw, H.R. Tan, K.L. Shen, One-step synthesis of methyl isobutyl ketone from acetone and hydrogen over Pd/(Nb2O5/SiO2) catalysts. Appl. Catal. A: Gen. 205 (2001) 61–69.

DOI: 10.1016/s0926-860x(00)00545-7

[37] W. Nicol, E.L. du Toit, One-step methyl isobutyl ketone synthesis from acetone and hydrogen using Amberlyst® CH28, Chem. Engg. Proc., 43 (2004) 1539–1545.

DOI: 10.1016/j.cep.2004.02.008

[38] S. Talwalkar, S. Mahajani, Synthesis of methyl isobutyl ketone from acetone over metal-doped ion exchange resin catalyst, Appl. Catal. A: Gen. 302 (2006) 140–148.

DOI: 10.1016/j.apcata.2006.01.004

[39] E.F. Kozhevnikova, I.V. Kozhevnikov, One-step synthesis of methyl isobutyl ketone from acetone catalysed by Pd supported on ZnII–CrIII mixed oxide, J. Catal. 238 (2006) 286–292.

DOI: 10.1016/j.jcat.2005.11.028

[40] F. Al-Wadaani, E.F. Kozhevnikova, I.V. Kozhevnikov, Pd supported on ZnII–CrIII mixed oxide as a catalyst for one-step synthesis of methyl isobutyl ketone, J. Catal. 257 (2008) 199–205.

DOI: 10.1016/j.jcat.2008.04.025

[41] R.D. Hetterley, E.F. Kozhevnikova, I.V. Kozhevnikov, Multifunctional catalysis by Pd-polyoxometalate: one-step conversion of acetone to methyl isobutyl ketone, Chem. Comm. 2006, 782-784.

DOI: 10.1039/b515325e

[42] P. Wang, S. Bai, J. Zhao, P. Su, Q. Yang, C. Li, Synthesis of Methyl Isobutyl Ketone from Acetone, Chem Sus Chem 2012, 5, 2390 – 2396

DOI: 10.1002/cssc.201200383

[43] Y. Pan, B. Yuan, Y. Li, D. He, Multifunctional catalysis by Pd@MIL-101: one-step synthesis of methyl isobutyl ketone over palladium nanoparticles deposited on a metal–organic framework, Chem. Commun., 2010, 46, 2280–2282.

DOI: 10.1039/b922061e

[44] A.A. Nikolopoulos, B.W.-L. Jang , J.J. Spivey, Acetone condensation and selective hydrogenation to MIBK on Pd and Pt hydrotalcite-derived Mg–Al mixed oxide catalysts, Appl. Catal. A: Gen. 296 (2005) 128–136

DOI: 10.1016/j.apcata.2005.08.022

[45] F. Winter, A. Jos van Dillen, K.P. de Jong, Single-stage liquid-phase synthesis of methyl isobutyl ketone under mild conditions. J. Mol. Catal. A: Chem. 219 (2004) 273–281.

DOI: 10.1016/j.molcata.2004.04.040

[46] F. Winter, V. Koot, A. J. van Dillen, J.W. Geus, K.P. de Jong, Hydrotalcites supported on carbon nanofibers as solid base catalysts for the synthesis of MIBK. J. Catal. 236 (2005) 91–100.

DOI: 10.1016/j.jcat.2005.09.020

[47] F. Winter, M. Wolters, A.J. van Dillen, K.P. de Jong, A hydrotalcite-based catalyst system for the single-stage liquid-phase synthesis of MIBK. Appl. Catal. A: Gen. 307 (2006) 231–238

DOI: 10.1016/j.apcata.2006.03.052

[48] D. Tichit, B. Coq, S. Cerneaux, R. Durand, Condensation of aldehydes for environmental friendly synthesis of 2-methyl-3-phenyl propanal by heterogeneous catalysis, Catal. Today 75 (2002) 197.

DOI: 10.1016/s0920-5861(02)00069-x

[49] L.M. Gandia and M. Montes, Appl. Catal. A, 101 (1993) L1.

[50] S. Narayanan, R. Unnikrishnan, Appl. Catal. A: Gen. 145 (1996) 231–236

[51] K.-H. Lin, A.-N. Ko, Na promotion of Pd/MgO catalysts for low-pressure one-step synthesis of MIBK from acetone + H2, Appl. Catal. A: Gen. 147 (1996) L259-L265

DOI: 10.1016/s0926-860x(96)00294-3

[52] J.J. Gamman, S.D. Jackson, F.A. Wigzell, Synthesis of Methyl Isobutyl Ketone over Pd/MgO/SiO2, Ind. Eng. Chem. Res. 49 (2010) 8439–8443.

DOI: 10.1021/ie100770e

[53] V. Chika´n, A. Molna´r, K. Bala´zsik, One-Step Synthesis of Methyl Isobutyl Ketone from Acetone and Hydrogen over Cu-on-MgO Catalysts, J. Catal. 184 (1999) 134–143.

DOI: 10.1006/jcat.1999.2437

[54] M. Varga, A´. Molna´r, G. Mulas, M. Mohai I. Berto´ti, G. Cocco, Cu–MgO Samples Prepared by Mechanochemistry for Catalytic Application, J. Catal. 206 (2002) 71–81.

DOI: 10.1006/jcat.2001.3476

[55] P.Y. Chen, S.J. Chu, C.C. Chen, N.S. Chang, W.C. Lin and T. K. Chuang, US Pat. 5059724 (1991).

[56] L. Melo, A. Llanos, M. Mediavilla, D. Moronta, J. Mol. Catal. A: Chem. 177 (2002) 281–287.

[57] L. Mattos, F. Noronha, J. Monteiro, J. Catal. 209 (2002) 166–176.

[58] R. Morales, L. Melo, J. Brito, A. Llanos, D. Moronta, L. Albornoz, E. Rodriguez, J. Mol. Catal. A: Chem. 203 (2003) 277–286.

[59] M. Mediavilla, L. Melo, Y. Dı´az, J.L. Brito, A. Albornoz, R. Solano, Influence of the acid sites density in the acetone transformation over bifunctional Pt/H[Ga]ZSM5 catalysts, Micropor. Mesopor. Mater. 102 (2007) 86–94.

DOI: 10.1016/j.micromeso.2006.12.017

[60] Y. Liu, K. Sun, X. Xu, X. Wang, HZSM-5 supported silica–zirconia and its application in one-step synthesis of methyl isobutyl ketone, Catal. Commun. 11 (2010) 322–325

DOI: 10.1016/j.catcom.2009.10.022

[61] P.P. Yang, J.F. Yu, Z.L. Wang, M.P. Xu, Q.S. Liu, X.W. Yang, T.H. Wu, Preparation, characterization of MCM-56 and catalytic activity in one-step synthesis of MIBK from acetone. Catal. Commun. 6 (2005) 107–111.

DOI: 10.1016/j.catcom.2004.11.008

[62] P.P. Yang, J.F. Yu, N. Xu, J. Wang, T. Wu, Influence of synthesis method on the properties and catalytic performance of MCM-49 zeolites, Catal. Commun. 8 (2007) 997–1002

DOI: 10.1016/j.catcom.2006.10.016

[63] P.P. Yang, Y. Shang, J. Yu , J. Wang, M. Zhang, T. Wu, One-step synthesis of methyl isobutyl ketone from acetone over Pd/MCM-22 zeolites, J. Mol.Catal. A: Chem. 272 (2007) 75–83

DOI: 10.1016/j.molcata.2007.03.037

[64] L.V. Mattos, F.B. Noronha, J.L.F. Monteiro, Bifunctional Metal/Base Catalysts (Pt/X) for the Direct Synthesis of MIBK from Acetone, J. Catal. 209 (2002) 166–176.

DOI: 10.1006/jcat.2002.3625

[65] A.C.C. Rodrigues, J.L.F. Monteiro, Direct synthesis of MIBK from acetone over Pd/NaX catalysts, Appl. Catal. A: Gen. 362 (2009) 185–192.

DOI: 10.1016/j.apcata.2009.04.041

[66] N. Cheikhi, M. Kacimi, M. Rouimi, M. Ziyad, L.F. Liotta, G. Pantaleo, G. Deganello, Direct synthesis of methyl isobutyl ketone in gas-phase reaction over palladium-loaded hydroxyapatite, J. Catal. 232 (2005) 257–267.

DOI: 10.1016/j.jcat.2005.03.016

[67] P.V.R. Rao, V.P. Kumar, G.S. Rao, K.V.R. Chary, Vapor phase selective hydrogenation of acetone to methyl isobutyl ketone (MIBK) over Ni/CeO2 catalysts, Catal. Sci. Technol., 2 (2012) 1665–1673.

DOI: 10.1039/c2cy20021j

[68] Y.Z. Chen, C.M. Hwang, C.W. Liaw, One-step synthesis of methyl isobutyl ketone from acetone with calcined Mg/Al hydrotalcite-supported palladium or nickel catalysts. Appl. Catal. A: Gen. 169 (1998) 207 -214

DOI: 10.1016/s0926-860x(98)00019-2

[69] R. Unnikrishnan, S. Narayanan, Metal containing layered double hydroxides as efficient catalyst precursors for the selective conversion of acetone, J. Mol. Catal. A: Chem. 144 (1999)173–179.

DOI: 10.1016/s1381-1169(98)00355-0

[70] N.N. Das, D. Tichit, R. Durand, P. Graffin, Bernard Coq, Influence of the metal function in the "one-pot" synthesis of 4-methyl-2-pentanone (methyl isobutyl ketone) from acetone over palladium supported on Mg(Al)O mixed oxides catalysts, Catal. Lett. 71 (2001) 181-185.

DOI: 10.1016/s1381-1169(03)00179-1

[71] F. Basile, L. Basini, G. Fornasari, M. Gazzano, F. Trifiro, A. Vaccari, J. Chem. Soc., Chem. Commun. (1996) 2435.

DOI: 10.1039/cc9960002435

[72] N.N. Das, S.C. Srivastava, Catalytic characterization of bi-functional catalysts derived from Pd–Mg–Al layered double hydroxides, Bull. Mater. Sci. 25 (2002) 283-289.

DOI: 10.1007/bf02704120

[73] M. Mart´ınez-Ortiz, D. Tichit, P. Gonzalez, B. Coq, The "one-pot" synthesis of 4-methyl-2-pentanone (methyl isobutyl ketone) from acetone over PdCu catalysts prepared from layered double hydroxides, J. Mol. Catal. A: Chem. 201 (2003) 199–210.

DOI: 10.1016/s1381-1169(03)00179-1

[74] V. Ponec, G.C. Bond, Catalysis by Metals and Alloys, Elsevier, Amsterdam, (1995)

[75] Palomares AE, Prato JG, Maquez F, Corma A (2003) Appl Catal. B 41:3

[76] N.N. Das, R. Das, Synthesis, characterization and activation of quaternary layered double hydroxides for the one-pot synthesis of methyl isobutyl ketone, Reac Kinet. Mech. Cat. 99 (2010) 397–408.

DOI: 10.1007/s11144-009-0141-y

[77] A.C.C. Rodrigues, J.L.F. Monteiro, C.A. Henriques, Ni-containing mixed oxides as catalysts for the one-step synthesis of methyl-isobutyl-ketone (MIBK) from acetone, C. R. Chimie 12 (2009) 1296–1304

DOI: 10.1016/j.crci.2009.06.005

[78] R.D. Hetterley, R. Mackey, J.T.A. Jones, Y.Z. Khimyak, A.M. Fogg and I.V. Kozhevnikov, One-step conversion of acetone to methyl isobutyl ketone over Pd – mixed oxide catalysts prepared from novel layered double hydroxides, J. Catal. 258 (2008) 250-255.

DOI: 10.1016/j.jcat.2008.06.017

[79] J. I. Di Cosimo,1 G. Torres, and C. R. Apestegu´ıa, One-Step MIBK Synthesis: A New Process from 2-Propanol, J. Catal., 208 (2002) 114–123.

DOI: 10.1006/jcat.2002.3551

[80] G. Torres, C.R. Apesteguı´a, J.I. Di Cosimo, One-step methyl isobutyl ketone (MIBK) synthesis from 2-propanol: Catalyst and reaction condition optimization, Appl. Catal. A: Gen. 317 (2007) 161–170.

DOI: 10.1016/j.apcata.2006.10.010