Highly product-selective and scalable rare-earth metal-catalyzed Meinwald rearrangement of epoxy oleochemicals under solvent-free conditions

Rafik Rajjak Shaikh; Rais Ahmad Khan; Ali Alsalme

Journal of Industrial and Engineering Chemistry, Vol.64, 446-452, August, 2018

DOI10.1016/j.jiec.2018.03.041 Export Citation

Highly product-selective and scalable rare-earth metal-catalyzed Meinwald rearrangement of epoxy oleochemicals under solvent-free conditions

Rafik Rajjak Shaikh^†, Rais Ahmad Khan^{1, †}, and Ali Alsalme^{1, †}

School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), 555 Moo 1, Payupnai, Wangchan, Rayong, 21210, Thailand
¹Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

E-mail:, ,

Using a rare-earth metal-based catalytic system, methyl oleate has been transformed into corresponding keto-derivatives via a Meinwald rearrangement of epoxidized methyl oleate (EMO). YCl3 efficiently carried out ring-opening of EMO under solvent-free conditions within a short reaction time. Only 3 wt% of YCl3 is enough to deliver selectively keto-products in excellent yields without requiring any column purifications. Also, this catalytic approach is very effective with a representative set of biobased unsaturated fatty acid methyl esters (FAME). Overall, this effective synthesis of keto derivatives promises novel materials with high biobased content and is very useful for industries of today and the future.

Keywords:Epoxides;Oleochemicals;Rare-earth metal catalysis;Solvent-free;Green chemistry

[References]

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Sheldon RA, Green Chem., 19, 18 (2017)
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[1] Warner JC, Cannon AS, Dye KM, Environ. Impact Assess., 24, 775 (2004)

[2] Anastas P, Eghbali N, Chem. Soc. Rev., 39, 301 (2010)

[3] Shibasaki M, J. Synth. Org. Chem. Jpn., 70, 1073 (2012)

[4] Sheldon RA, Green Chem., 19, 18 (2017)

[5] Jimenez-Gonzalez C, Constable DJC, Ponder CS, Chem. Soc. Rev., 41, 1485 (2012)

[6] Mardhiah HH, Ong HC, Masjuki HH, Lim S, Lee HV, Renew. Sust. Energ. Rev., 67, 1225 (2017)

[7] Miandad R, Barakat MA, Rehan M, Aburiazaiza AS, Ismail IMI, Nizami AS, Waste Manage., 69, 66 (2017)

[8] Kabir G, Din ATM, Hameed BH, Bioresour. Technol., 249, 42 (2018)

[9] Okoye PU, Abdullah AZ, Hameed BH, Fuel, 209, 538 (2017)

[10] Wan Z, Lim JK, Hameed BH, Energy, 141, 1989 (2017)

[11] Natongchai W, Khan RA, Alsalme A, Shaikh RR, Catalysts, 7, 340 (2017)

[12] Xi L, Shaikh RR, Roosevelt P, Du X, Yu H, Novack D, Meguellati K, Mediterr. J. Chem., 6, 49 (2017)

[13] Shaikh IR, Shaikh RA, Shaikh AA, War JA, Hangirgekar SP, Shaikh AL, Shaikh PR, Shaikh RR, J. Catal., 2015, 1 (2015)

[14] Bouhrara M, Ranga C, Fihri A, Shaikh RR, Sarawade P, Emwas AH, Hedhili MN, Polshettiwar V, ACS Sustain. Chem. Eng., 1, 1192 (2013)

[15] Palmieri A, Petrini M, Shaikh RR, Org. Biomol. Chem., 8, 1259 (2010)

[16] Petrini M, Shaikh RR, Synthesis, 2009, 3143 (2009)

[17] Petrini M, Shaikh RR, Tetrahedron Lett., 49, 5645 (2008)

[18] Palmieri A, Petrini M, Shaikh RR, Synlett, 2008, 1845 (2008)

[19] Shaikh RR, Mazzanti A, Petrini M, Bartoli G, Melchiorre P, Angew. Chem.-Int. Edit., 47, 8707 (2008)

[20] Ballini R, Palmieri A, Petrini M, Shaikh RR, Adv. Synth. Catal., 350, 129 (2008)

[21] Corma A, Iborra S, Velty A, Chem. Rev., 107(6), 2411 (2007)

[22] Vasquez MC, Silva EE, Castillo EF, Biomass Bioenergy, 105, 197 (2017)

[23] Cherubini F, Energy Conv. Manag., 51(7), 1412 (2010)

[24] Ghatak HR, Renew. Sust. Energ. Rev., 15, 4042 (2011)

[25] Horvath IT, Chim. Oggi, 32, 76 (2014)

[26] Horvath IT, Csefalvay E, Mika LT, Debreczeni M, ACS Sustain. Chem. Eng., 5, 2734 (2017)

[27] Patel AD, Meesters K, den Uil H, de Jong E, Worrell E, Patel MK, ChemSusChem, 6, 1724 (2013)

[28] Sheldon RA, Catal. Today, 167(1), 3 (2011)

[29] Sheldon RA, J. Mol. Catal. A-Chem., 422, 3 (2016)

[30] Shamanaev I, Deliy I, Gerasimov E, Pakharukova V, Kodenev E, Aleksandrov P, Bukhtiyarova G, Catalysts, 7, 329 (2017)

[31] Ye R, Hayes D, Burton R, Liu A, Harte F, Wang Y, Catalysts, 6, 78 (2016)

[32] Konkol M, Wrobel W, Bicki R, Gołe˛biowski A, Catalysts, 6, 55 (2016)

[33] Atadashi IM, Aroua MK, Abdul Aziz AR, Sulaiman NMN, J. Ind. Eng. Chem., 19(1), 14 (2013)

[34] Ghotli RA, Aziz ARA, Atadashi IM, Hasan DB, Kong PS, Aroua MK, J. Ind. Eng. Chem., 21, 1039 (2015)

[35] Erhan SZ, Bagby MO, J. Am. Oil Chem. Soc., 71, 1223 (1994)

[36] Liu ZS, Erhan S, J. Polym. Environ., 18, 243 (2010)

[37] Liu ZS, Erhan SZ, J. Am. Oil Chem. Soc., 87, 437 (2010)

[38] Higgins NWB, Stults JF, Stabilized Vegetable Oils and Methods of Making Same, Bunge Oils, Inc., St. Louis, MO, United States, 2008.

[39] McNutt J, He Q, J. Ind. Eng. Chem., 36, 1 (2016)

[40] Boyer A, Cloutet E, Tassaing T, Gadenne B, Alfos C, Cramail H, Green Chem., 12, 2205 (210)

[41] Doll KM, Erhan SZ, J. Agric. Food Chem., 53, 9608 (2005)

[42] Pages X, Alfos C, Ocl Ol. Corps Gras Lipides, 8, 122 (2001)

[43] Fraile JM, Garcia JI, Herrerias CI, Pires E, Synthesis, 49, 1444 (2017)

[44] Doll KM, Bantchev GB, Murray RE, ACS Sustain. Chem. Eng., 1, 39 (2012)

[45] Morandi B, Wickens ZK, Grubbs RH, Angew. Chem.-Int. Edit., 52, 2944 (2013)

[46] Morandi B, Grubbs RH, Wickens ZK, Process for the Synthesis of Ketones from Internal Alkenes, California Institute of Technology, USA, pp.29 2014.

[47] Winkler M, Meier MAR, Green Chem., 16, 1784 (2014)

[48] Hermans I, Janssen K, Moens B, Philippaerts A, Van Berlo B, Peeters J, Jacobs PA, Sels BF, Adv. Synth. Catal., 349, 1604 (2007)

[49] Rios LA, Llano BA, Hoelderich WF, Appl. Catal. A: Gen., 445-446, 346 (2012)

[50] Piazza GJ, Nunez A, Foglia TA, J. Am. Oil Chem. Soc., 80, 901 (2003)

[51] Jung JH, Yoo ES, Dang TH, Kang HJ, Carboxylic Acid Derivatives for Treating Inflammation, Seoul National University, R & DB Foundation, S. Korea, pp.19 2009.

[52] Dang HT, Lee HJ, Yoo ES, Shinde PS, Lee YM, Hong J, Kim DK, Jung JH, J. Nat. Prod., 71, 232 (2008)

[53] Higgins NW, Stults JF, Stabilized Vegetable Oils, Bunge Oils, Inc., USA, 2008 pp. 15pp., Cont.-in-part of U.S. Ser. No. 839,853.

[54] Stoll G, Grundt E, Henkel K.-G.a.A, Germany, pp.6 1991.

[55] Rane SS, Chadha MS, Mamdapur VR, Chemosphere, 27, 1419 (1993)

[56] Guidotti M, Psaro R, Ravasio N, Sgobba M, Carniato F, Bisio C, Gatti G, Marchese L, Green Chem., 11, 1173 (2009)