Metal- and halide-free solid-type multifunctional alkanolamines as catalysts for cycloaddition of CO2

Hyeon-Gook Kim; Hye Jeong Son; Choong-Sun Lim

Korean Journal of Chemical Engineering, Vol.36, No.2, 197-202, February, 2019

DOI10.1007/s11814-018-0194-6 Export Citation

Metal- and halide-free solid-type multifunctional alkanolamines as catalysts for cycloaddition of CO2

Hyeon-Gook Kim^†, Hye Jeong Son, and Choong-Sun Lim

Advanced Industrial Chemistry Research Center, Advanced Convergent Chemistry Division, Korea Research Institute of Chemical Technology, 45 Jongga-ro, Jung-gu, Ulsan 44412, Korea

E-mail:

Although the production of cyclic carbonates from CO2 and epoxides can be promoted by eco-friendly halogen- and metal-free organic catalysts, its homogeneity complicates the catalyst reuse. Herein, we synthesized solid multifunctional alkanolamines using simple epoxy and amine reactions, and analyzed their structures by IR and 13CNMR. Then, we employed these as catalysts for CO2 cycloaddition with propylene oxide, obtaining propylene carbonate in 98% yield after 3 h at 120 °C. Moreover, at 60 °C, the reaction was successfully repeated five times and a product yield of 50% was maintained throughout.

Keywords:Alkanolamine;Carbon Dioxide Fixation;Metal- and Halide-free;Solid Catalyst;Propylene Carbonate

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[1] Anderson TR, Hawkins E, Jones PD, Endeavour, 40, 178 (2016)

[2] Alper E, Orhan OY, Petroleum, 3, 109 (2017)

[3] North M, Pasquale R, Young C, Green Chem., 12, 1514 (2010)

[4] Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kuhn FE, Angew. Chem.-Int. Edit., 50, 8510 (2011)

[5] North M, Pasquale R, Angew. Chem.-Int. Edit., 48, 2946 (2009)

[6] Dai WL, Luo SL, Yin SF, Au CT, Appl. Catal. A: Gen., 366(1), 2 (2009)

[7] Cokoja M, Wilhelm ME, Anthofer MH, Herrmann WA, Kuhn FE, ChemSusChem, 8, 2436 (2015)

[8] Martin C, Fiorani G, Kleij AW, ACS Catal., 5, 1353 (2015)

[9] Shaikh AA, Sivaram S, Chem. Rev., 96(3), 951 (1996)

[10] Sakakura T, Kohno K, Chem. Commun., 1312 (2009).

[11] Huang SY, Liu SG, Li JP, Zhao N, Wei W, Sun YH, Fuel Chem. Technol., 35, 701 (2007)

[12] Bhanage BM, Fujita S, Ikushima Y, Arai M, Appl. Catal. A: Gen., 219(1-2), 259 (2001)

[13] Bai D, Duan S, Hai L, Jing H, ChemCatChem, 4, 1752 (2012)

[14] Zhang J, Cheng X, Zhang B, Shi J, Zheng L, Zhang J, Shao D, Tan X, Han B, Yang G, ChemCatChem, 10, 1 (2018)

[15] Song J, Zhang Z, Han B, Hu S, Li W, Xie Y, Green Chem., 10, 1337 (2008)

[16] He LN, Yasuda H, Sakakura T, Green Chem., 5, 92 (2003)

[17] Decortes A, Castilla AM, Kleij AW, Angew. Chem.-Int. Edit., 49, 9822 (2010)

[18] Zhang Y, Chan JYG, Energy Environ. Sci., 3, 408 (2010)

[19] Vieira MO, Monteiro WF, Neto BS, Ligabue R, Chaban VV, Einloft S, Catal. Lett., 148, 108 (2018)

[20] Wasserscheid P, Welton T, Ionic Liquids in Synthesis, 2nd Ed., Wiley-VCH (2008).

[21] Kim HG, Lim CS, Kim DW, Cho DH, Lee DK, Chung JS, Mol. Catal., 438, 121 (2017)

[22] Chen J, Zhong M, Tao L, Liu L, Jayakumar S, Li C, Li H, Yang Q, Green Chem., 20, 903 (2018)

[23] Wu S, Teng C, Cai S, Jiang B, Wang Y, Meng H, Tao H, Nanoscale Res. Lett., 12, 1 (2017)

[24] Wu LX, Yang HP, Guan YB, Yang MP, Wang H, Lu JX, Int. J. Electrochem. Sci., 12, 8963 (2017)

[25] Lan DH, Gong YX, Tan NY, Wu SS, Shen J, Yao KC, Yi B, Au CT, Yin SF, Carbon, 127, 245 (2018)

[26] Lan DH, Wang HT, Chen L, Au CT, Yin SF, Carbon, 100, 81 (2016)

[27] Lan DH, Chen L, Au CT, Yin SF, Carbon, 93, 22 (2015)

[28] Lan DH, Yang FM, Luo SL, Au CT, Yin SF, Carbon, 73, 351 (2014)

[29] Yang ZZ, Zhao YN, He LN, RSC Adv., 1, 545 (2011)

[30] Sun J, Cheng WG, Fan W, Wang YH, Meng ZY, Zhang SJ, Catal. Today, 148(3-4), 361 (2009)

[31] Jadhav AH, Thorat GM, Lee K, Lim AC, Kang H, Seo JG, Catal. Today, 265, 56 (2016)

[32] Sammelson RE, Kurth MJ, Chem. Rev., 101(1), 137 (2001)

[33] Chen A, Zhang Y, Chen J, Chen L, Yu Y, J. Mater. Chem. A, 3, 9807 (2015)

[34] Meng XL, Nie Y, Sun J, Cheng WG, Wang JQ, He HY, Zhang SJ, Green Chem., 16, 2771 (2014)

[35] Talapaneni SN, Buyukcakir O, Je SH, Srinivasan S, Seo Y, Polychronopoulou K, Coskun A, Chem. Mater., 27, 6818 (2015)

[36] Roeser J, Kailasam K, Thomas A, ChemSusChem, 5, 1793 (2012)

[37] Skelton R, Dubois F, Zenobi R, Anal. Chem., 72, 1707 (2000)

[38] Rangel-Vazquez NA, Sanchez-Lopez C, Felix FR, Polimeros, 24, 453 (2014)

[39] Mathers NJ, Xu Z, Geoderma, 114, 19 (2003)

[40] Ochiai B, Endo T, Prog. Polym. Sci, 30, 183 (2005)

[41] Tomalia DA, Swanson DR, Huang B, Svenson S, Reyna LA, Michael A, DeMattei CR, Heinzelmann JR, US Patent, 0298006A1 (2007).

[42] Roshan KR, Kim BM, Kathalikkattil AC, Tharun J, Won YS, Park DW, Chem. Commun., 50, 13664 (2014)