One-pot solvent-free synthesis of fatty acid alkanoamides from natural oil triglycerides using alkali metal doped CaO nanoparticles as heterogeneous catalyst

Dinesh Kumar; Hyeon Kuk; Amjad Ali

Journal of Industrial and Engineering Chemistry, Vol.38, 43-49, June, 2016

DOI10.1016/j.jiec.2016.04.004 Export Citation

One-pot solvent-free synthesis of fatty acid alkanoamides from natural oil triglycerides using alkali metal doped CaO nanoparticles as heterogeneous catalyst

Dinesh Kumar^†, Hyeon Kuk¹, and Amjad Ali^{2, †}

Department of Bionanosystem Engineering, Chonbuk National University, Jeonju 561-756, South Korea
¹Department of BIN-Fusion Technology, Chonbuk National University, Jeonju 561-756, South Korea
²School of Chemistry and Biochemistry, Thapar University, Patiala 147004, India

E-mail:,

One-pot solvent-free amidation of natural triglycerides (pongamia and jatropha oil) was investigated using Li or Na or K doped CaO nanoparticles as heterogeneous catalyst. Complete conversion (98 ± 2%) of pongamia oil and jatropha oil to fatty diethanolamides has been obtained in 0.75 h and 1 h, respectively, using 5 wt% of Li doped CaO (2-LiH/CaO-400) and 6:1 molar ratio of diethanolamine/oil at 90 ℃. The same catalyst was active up to six catalytic recycles for amidation of both feedstocks. The rate of reaction and activation energy for the same reaction process was calculated as 0.101 min-1 and 48.3 kJ mol-1, respectively.

Keywords:Alkanoamides;Triglycerides;Nanoparticles;Heterogeneous catalyst;Reusability

[References]

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[1] Foye WO, Lemke TL, Williams DA, Foye’s Principles of Medicinal Chemistry, Lippincott Williams & Wilkins, 2008.

[2] Sutherland AG, in: Katritzky AR, Taylor RJK (Eds.), 1.01 - One or More CH Bond(s) Formed by Substitution: Reduction of C-Halogen and C-Chalcogen Bonds A2, Elsevier, Oxford, 2005, p. 1.

[3] de Almeida CG, Garbois GD, Amaral LM, Diniz CC, Hyaric ML, Biomed. Pharmacother., 64, 287 (2010)

[4] Montalbetti CAGN, Falque V, Tetrahedron, 61, 10827 (2005)

[5] Karis ND, Loughlin WA, Jenkins ID, Tetrahedron, 63, 12303 (2007)

[6] Nadimpally KC, Thalluri K, Palakurthy NB, Saha A, Mandal B, Tetrahedron Lett., 52, 2579 (2011)

[7] Bhella SS, Elango M, Ishar MPS, Tetrahedron, 65, 240 (2009)

[8] Levinson WE, Kuo TM, Knothe G, Bioresour. Technol., 99(7), 2706 (2008)

[9] Perreux L, Loupy A, Volatron F, Tetrahedron, 58, 2155 (2002)

[10] van Pelt S, Teeuwen RLM, Janssen MHA, Sheldon RA, Dunn PJ, Howard RM, Kumar R, Martinez I, Wong JW, Green Chem., 13, 1791 (2011)

[11] Biermann U, Friedt W, Lang S, Luhs W, Machmuller G, Metzger JO, Klaas MR, Schafer HJ, Schneider MP, New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry, Wiley-VCH Verlag GmbH, 2008p. 253.

[12] Kuo TM, Kim H, Hou CT, Curr. Microbiol., 43(3), 198 (2001)

[13] Maag H, J. Am. Oil Chem. Soc., 61, 259 (1984)

[14] de Zoete MC, Kock-van Dalen AC, van Rantwijk F, Sheldon RA, J. Mol. Catal. B-Enzym., 1, 109 (1996)

[15] Levinson WE, Kuo TM, Kurtzman CP, Enzyme Microb. Technol., 37(1), 126 (2005)

[16] Awasthi NP, Singh RP, Eur. J. Lipid Sci. Technol., 111, 202 (2009)

[17] Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, Leazer JJL, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY, Green Chem., 9, 411 (2007)

[18] Alipour Z, Rezaei M, Meshkani F, J. Ind. Eng. Chem., 20(5), 2858 (2014)

[19] Hu K, Wang H, Liu Y, Yang C, J. Ind. Eng. Chem., 28, 334 (2015)

[20] Ketcong A, Meechan W, Naree T, Seneevong I, Winitsorn A, Butnark S, Ngamcharussrivichai C, J. Ind. Eng. Chem., 20(4), 1665 (2014)

[21] Ngamcharussrivichai C, Meechan W, Ketcong A, Kangwansaichon K, Butnark S, J. Ind. Eng. Chem., 17(3), 587 (2011)

[22] Watkins RS, Lee AF, Wilson K, Green Chem., 6, 335 (2004)

[23] Yan S, Lu H, Liang B, Energy Fuels, 22, 646 (2007)

[24] Kumar D, Ali A, Energy Fuels, 27(7), 3758 (2013)

[25] Kumar D, Ali A, Energy Sources Part A-Recovery Util. Environ. Eff., 36(10), 1093 (2014)

[26] de Almeida CG, de Souza IF, Sousa RA, Hyaric ML, Catal. Commun., 42, 25 (2013)

[27] Degirmenbasi N, Boz N, Kalyon DM, Appl. Catal. B: Environ., 150-151, 147 (2014)

[28] Alcantara R, Amores J, Canoira L, Fidalgo E, Franco MJ, Navarro A, Biomass Bioenerg., 18, 515 (2000)

[29] Qadri SB, Skelton EF, Hsu D, Dinsmore AD, Yang J, Gray HF, Ratna BR, Phys. Rev. B, 60, 9191 (1999)

[30] Correia LM, Saboya RMA, Campelo ND, Cecilia JA, Rodriguez-Castellon E, Cavalcante CL, Vieira RS, Bioresour. Technol., 151, 207 (2014)

[31] Ngamcharussrivichai C, Nunthasanti P, Tanachai S, Bunyakiat K, Fuel Process. Technol., 91(11), 1409 (2010)

[32] Freedman B, Butterfield RO, Pryde EH, J. Am. Oil Chem. Soc., 63, 1375 (1986)

[33] Singh AK, Fernando SD, Chem. Eng. Technol., 30(12), 1716 (2007)

[34] Balbino JM, de Menezes EW, Benvenutti EV, Cataluna R, Ebeling G, Dupont J, Green Chem., 13, 3111 (2011)

[35] Sivasamy A, Cheah KY, Fornasiero P, Kemausuor F, Zinoviev S, Miertus S, ChemSusChem, 2, 278 (2009)

[36] Reddy C, Reddy V, Oshel R, Verkade JG, Energy Fuels, 20(3), 1310 (2006)

[37] Bundesmann MW, Coffey SB, Wright SW, Tetrahedron Lett., 51, 3879 (2010)

[38] Wang X, Wang X, Wang T, J. Agric. Food Chem., 60, 451 (2011)

[39] Al-Mulla EAJ, Yunus WMZW, Ibrahim NAB, Rahman MZA, J. Oleo Sci., 58, 467 (2009)

[40] Xiao P, Zhang S, Ma H, Zhang A, Lv X, Zheng L, J. Biotechnol., 168, 552 (2013)

[41] Arora R, Paul S, Gupta R, Can. J. Chem., 83, 1137 (2005)

[42] Rawlins J, Pramanik M, Mendon S, J. Am. Oil Chem. Soc., 85, 783 (2008)

[43] Kumar D, Kim SM, Ali A, New J. Chem., 39, 7097 (2015)