Alternative integrated distillation strategies for the purification of acetonitrile from ethanol ammoxidation

Antonio Tripodi; Dario Manzini; Matteo Compagnoni; Gianguido Ramis; Ilenia Rossetti

Journal of Industrial and Engineering Chemistry, Vol.59, 35-49, March, 2018

DOI10.1016/j.jiec.2017.10.003 Export Citation

Alternative integrated distillation strategies for the purification of acetonitrile from ethanol ammoxidation

Antonio Tripodi, Dario Manzini, Matteo Compagnoni, Gianguido Ramis¹, and Ilenia Rossetti^†

Dip. Chimica, Università degli Studi di Milano, CNR-ISTM and INSTM Unit Milano-Università, via C. Golgi 19, 20133 Milano, Italy
¹Dip. Ing. Chimica, Civile ed Ambientale, Università degli Studi di Genova and INSTM Unit Genova, P.le J.F. Kennedy 1, Genoa, Italy

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The feasibility and performance of different strategies to purify a complex mixture of H2O/CH3CN/NH3/ HCN from bioethanol ammoxidation are compared. Dichloromethane as entrainer is taken as a base case and compared with more sustainable molecules, such as ethyl acetate (EA), ethylene glycol (EG) and glycerol (G). The thermodynamic behavior of the homogeneous or heterogeneous mixtures is first discussed. Then, the separation and purification section is designed accordingly. To yield high-purity acetonitrile a low-boiling entrainer (EA) is preferable. If economic issues prevail, then EG grants a lighter sizing of the equipment and lower heat duties. Similar recoveries of acetonitrile, ranging from 90 (EG and G) to 92% (DCM and EA) were achieved when comparing the different entrainers. Higher purities are obtained with the lower-boiling additives with respect to acetonitrile, leading to purity >99.99% for DCM and EA, >99.6% for EG and >99% for G. This acetonitrile purification section is part of a full integrated plant, newly designed for the production of this commodity from renewable sources, since no commercial examples of bioethanol-to-acetonitrile plants are disclosed in the literature.

Keywords:Acetonitrile;Distillation;Azeotrope separation;Process simulation;Thermodynamic models

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[2] Mcconvey IF, Woods D, Lewis M, Gan Q, Nancarrow P, Org. Process Res. Dev., 16, 612 (2012)

[3] Lei ZG, Zhou RQ, Duan ZT, Chem. Eng. J., 85(2-3), 379 (2002)

[4] Liao B, Lei ZG, Xu Z, Zhou RQ, Duan ZT, Chem. Eng. J., 84(3), 581 (2001)

[5] Yang Q, Xing H, Su B, Yu K, Bao Z, Yang Y, et al., Chem. Eng. J., 181-182, 334 (2012)

[6] Lv W, Zhang R, Gao P, Gong C, J. Solid State Electrochem., 17, 2789 (2013)

[7] Tullo A, Chem. Eng. News, 86, 2008 (2008)

[8] Eshelman L, Delgass W, Catal. Today, 21, 229 (1994)

[9] Hummel AA, Badani MV, Hummel KE, Delgass WN, J. Catal., 139, 392 (1993)

[10] Moussa AS, Jimenez L, Ind. Eng. Chem. Res., 45(12), 4304 (2006)

[11] Hamill C, Driss H, Goguet A, Burch R, Petrov L, Daous M, Rooney D, Appl. Catal. A: Gen., 506, 261 (2015)

[12] Folco F, Ochoa JV, Cavani F, Ott L, Janssen M, Catal. Sci. Technol., 7, 200 (2017)

[13] Sun J, Wang Y, ACS Catal., 4, 1078 (2014)

[14] Luyben WL, Sep. Purif. Technol., 174, 232 (2017)

[15] Zhu ZY, Xu DF, Liu XZ, Zhang Z, Wang YL, Sep. Purif. Technol., 169, 66 (2016)

[16] Donis IR, Gerbaud V, Joulia X, Ind. Eng. Chem. Res., 40, 4935 (2016)

[17] Sazonova AY, Raeva VM, Selection AE, Int. J. Chem. Mol. Nucl. Mater. Metall. Eng., 9, 288 (2015)

[18] AAVV, Soc. Mining Metall. Explor. Inc. (2014).

[19] Mittemeijer E, Somers M(Eds.), Thermochemical Surface Engineering of Steel. pdf, Woodhead Publishing Series, ELSEVIER, 2015.

[20] Horsley H, Azeotropic Data, American Chemical Society, 1973.

[21] Shulgin I, Fischer K, Noll O, Gmehling J, Ind. Eng. Chem. Res., 40(12), 2742 (2001)

[22] Luyben WL, Distillation Design and Control Using Aspen Simulation, II, John Wiley & Sons, 2013.

[23] Wasylkiewicz SK, Kobylka LC, Castillo FJL, Chem. Eng. J., 92(1-3), 201 (2003)

[24] Wasylkiewicz SK, Kobylka LC, Castillo FJL, Chem. Eng. J., 79(3), 219 (2000)

[25] Carra Ragaini, Zanderighi, Operazioni di trasferimento di massa, Manfredi editore, Milano, 1969.

[26] AAVV, Aspen Plus User Guide, 10.2, Aspen Technology, Inc., 2000.

[27] Rodriguez-Donis I, Gerbaud V, Joulia X, Ind. Eng. Chem. Res., 40(12), 2729 (2001)

[28] Gmehling J, Schedemann A, Ind. Eng. Chem. Res., 53(45), 17794 (2014)

[29] Gmehling J, Mollman C, Ind. Eng. Chem. Res., 37(8), 3112 (1998)

[30] Dimian AC, Bildea CS, Kiss AA, Integrated Design & Simulation of Chemical Processes, II, Computer Aided Chemical Engineering, ELSEVIER, 2014.

[31] Chen CC, Mathias PM, AIChE J., 48(2), 194 (2002)

[32] Villamanan MA, Van Ness HC, J. Chem. Eng. Data, 30, 445 (1985)

[33] Zapata RB, Villa AL, de Correa CM, Fluid Phase Equilib., 275(1), 46 (2009)

[34] Kojima K, Zhang SJ, Hiaki T, Fluid Phase Equilib., 131(1-2), 145 (1997)