Abstract
A reactive chromatography process was investigated for a transesterification reaction of propylene glycol methyl ether (DOWANOL™ PM) using a homogeneous catalyst, a sodium alkoxide. In the proposed process, fresh catalyst is supplied with desorbent, which allows independent optimization of the adsorption properties of the stationary phase. Deactivation of catalytic activity can be avoided, which had been found to be the bottleneck in our previous study for heterogeneous catalysis. To model and optimize this process, a series of batch reaction experiments, and pulse injection tests with a chromatographic column with and without reaction were carried out. From the experimental data, equilibrium and kinetic parameters were estimated using the inverse method. Using this model, a simulated moving bed reactor was designed that achieves a conversion of 95% using the homogeneous catalysis concept.
Similar content being viewed by others
References
Agrawal, G., Kawajiri, Y.: Comparison of various ternary simulated moving bed separation schemes by multi-objective optimization. J Chromatogr A. 1238, 105–113 (2012)
Agrawal, G., Oh, J., Sreedhar, B., Tie, S., Donaldson, M.E., Frank, T.C., Schultz, A.K., Bommarius, A.S., Kawajiri, Y.: Optimization of reactive simulated moving bed systems with modulation of feed concentration for production of glycol ether ester. J. Chromatogr. A. 1360, 196–208 (2014)
Co, C.E.T., Tan, M.C., Diamante, J.A.R., Yan, L.R.C., Tan, R.R., Razon, L.F.: Internal mass-transfer limitations on the transesterification of coconut oil using an anionic ion exchange resin in a packed bed reactor. Catal. Today. 174, 54–58 (2011)
da Silva, E.A.B., Pedruzzi, I., Rodrigues, A.E.: Simulated moving bed technology to improve the yield of the biotechnological production of lactobionic acid and sorbitol. Adsorption. 17, 145–158 (2011)
Demirbas, A.: Comparison of transesterification methods for production of biodiesel from vegetable oils and fats. Energy Convers. Manag. 49, 125–130 (2008)
Fourer, R., Gay, D.M., Kernighan, B.W.: A modeling language for mathematical-programming. Manag. Sci. 36, 519–554 (1990)
Geier, D., Soper, J.: US Patent US7828978 B2 (2007)
Gyani, V.C., Mahajani, S.: Reactive chromatography for the synthesis of 2-ethylhexyl acetate. Sep. Sci. Technol. 43, 2245–2268 (2008)
Hansen, P.C., O’Leary, D.P.: The use of the L-curve in the regularization of discrete ill-posed problems. SIAM J. Sci. Comput. 14, 1487–1503 (1993)
He, B., Ren, Y., Cheng, Y., Li, J.: Deactivation and in situ regeneration of anion exchange resin in the continuous transesterification for biodiesel production. Energy Fuels. 26, 3897–3902 (2012)
Indlekofer, M., Brotz, F., Bauer, A., Reuss, M.: Stereoselective bioconversions in continuously operated fixed bed reactors: Modeling and process optimization. Biotechnol. Bioeng. 52, 459–471 (1996)
Jaya, N., Selvan, B.K., Vennison, S.J.: Synthesis of biodiesel from pongamia oil using heterogeneous ion-exchange resin catalyst. Ecotoxicol. Environ. Safe. 121, 3–9 (2015)
Kawajiri, Y., Biegler, L.T.: Comparison of configurations of a four-column simulated moving bed process by multi-objective optimization. Adsorption. 14, 433–442 (2008)
Kawase, M., Inoue, Y., Araki, T., Hashimoto, K.: The simulated moving-bed reactor for production of bisphenol A. Catal. Today. 48, 199–209 (1999)
Kim, M., Salley, S.O., Ng, K.Y.S.: Transesterification of glycerides using a heterogeneous resin catalyst combined with a homogeneous catalyst. Energy Fuels. 22, 3594–3599 (2008)
Kitagawa, N., Yonemoto, T.: Japanese Patent 2016-059833A (2016)
Kloppenburg, E., Gilles, E.D.: A new concept for operating simulated moving-bed processes. Chem. Eng. Technol. 22, 813–817 (1999)
Lee, D.W., Park, Y.M., Lee, K.Y.: Heterogeneous base catalysts for transesterification in biodiesel synthesis. Catal Surv. Asia. 13, 63–77 (2009)
Lode, F., Houmard, M., Migliorini, C., Mazzotti, M., Morbidelli, M.: Continuous reactive chromatography. Chem. Eng. Sci. 56, 269–291 (2001)
Mai, P.T., Vu, T.D., Mai, K.X., Seidel-Morgenstern, A.: Analysis of heterogeneously catalyzed ester hydrolysis performed in a chromatographic reactor and in a reaction calorimeter. Ind. Eng. Chem. Res. 43, 4691–4702 (2004)
Meher, L.C., Sagar, D.V., Naik, S.N.: Technical aspects of biodiesel production by transesterification—a review. Renew. Sustain. Energy Rev. 10, 248–268 (2006)
Minceva, M., Gomes, P.S., Meshko, V., Rodrigues, A.E.: Simulated moving bed reactor for isomerization and separation of p-xylene. Chem. Eng. J. 140, 305–323 (2008)
Oh, J., Agrawal, G., Sreedhar, B., Donaldson, M.E., Schultz, A.K., Frank, T.C., Bommarius, A.S., Kawajiri, Y.: Conversion improvement for catalytic synthesis of propylene glycol methyl ether acetate by reactive chromatography: experiments and parameter estimation. Chem. Eng. J. 259, 397–409 (2015)
Oh, J., Sreedhar, B., Donaldson, M.E., Frank, T.C., Schultz, A.K., Bommarius, A.S., Kawajiri, Y.: Transesterification of propylene glycol methyl ether in chromatographic reactors using anion exchange resin as a catalyst. J Chromatogr A. 1466, 84–95 (2016)
Patel, D., Saha, B.: Esterification of acetic acid with n-hexanol in batch and continuous chromatographic reactors using a gelular ion-exchange resin as a catalyst. Ind. Eng. Chem. Res. 51, 11965–11974 (2012)
Paterson, G., Issariyakul, T., Baroi, C., Bassi, A., Dalai, A.: Ion-exchange resins as catalysts in transesterification of triolein. Catal. Today. 212, 157–163 (2013)
Rodrigues, A.E., Pereira, C.S.M., Santos, J.C.: Chromatographic reactors. Chem. Eng. Technol. 35, 1171–1183 (2012)
Schmidt-Traub, H., Schulte, M., Seidel-Morgenstern, A.: Preparative Chromatography, 2nd edn. Wiley, Weinheim (2012)
Schuchardt, U., Sercheli, R., Vargas, R.M.: Transesterification of vegetable oils: a review. J. Braz. Chem. Soc. 9, 199–210 (1998)
Shibasaki-Kitakawa, N., Honda, H., Kuribayashi, H., Toda, T., Fukumura, T., Yonemoto, T.: Biodiesel production using anionic ion-exchange resin as heterogeneous catalyst. Biores. Technol. 98, 416–421 (2007)
Shibasaki-Kitakawa, N., Tsuji, T., Kubo, M., Yonemoto, T.: Biodiesel production from waste cooking oil using anion-exchange resin as both catalyst and adsorbent. BioEnergy Res. 4, 287–293 (2011)
Ströhlein, G., Assunção, Y., Dube, N., Bardow, A., Mazzotti, M., Morbidelli, M.: Esterification of acrylic acid with methanol by reactive chromatography: Experiments and simulations. Chem. Eng. Sci. 61, 5296–5306 (2006)
Talukder, M.M.R., Beatrice, K.L.M., Song, O.P., Puah, S., Wu, J.C., Won, C.J., Chow, Y.: Improved method for efficient production of biodiesel from palm oil. Energy Fuels. 22, 141–144 (2008)
Tapur, F.N., Bhanger, M.I., Rahman, A.U., Memon, G.Z.: Application of factorial design in optimization of anion exchange resin based methylation of vegetable oil and fats. Innov. Food Sci. Emerg. 9, 608–613 (2008)
Tie, S., Sreedhar, B., Agrawal, G., Oh, J.M., Donaldson, M., Frank, T., Schultz, A., Bommarius, A., Kawajiri, Y.: Model-based design and experimental validation of simulated moving bed reactor for production of glycol ether ester. Chem. Eng. J. 301, 188–199 (2016)
Tikhonov, A.N., Leonov, A.S., Yagola, A.G.: Nonlinear Ill-Posed Problems. World Congress of Nonlinear Analysis ‘92, vol. I, pp. 505–511. Walter de Gruyter & Co., Tampa (1995)
Vu, T.D., Seidel-Morgenstern, A.: Quantifying temperature and flow rate effects on the performance of a fixed-bed chromatographic reactor. J Chromatogr A. 1218, 8097–8109 (2011)
Wachter, A., Biegler, L.T.: On the implementation of an interior-point filter line-search algorithm for large-scale nonlinear programming. Math. Program. 106, 25–57 (2006)
Yonemoto, T., Kitagawa, N., Toda, T.: Japanese Patent 2006-104316 (2006)
Yonemoto, T., Kitagawa, N., Nakagawa, Y., Nakayama, M.: Japanese Patent 2010-195938 (2010)
Acknowledgements
Financial support from The Dow Chemical Company is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Oh, J., Sreedhar, B., Donaldson, M.E. et al. Transesterification of propylene glycol methyl ether by reactive simulated moving bed chromatography using homogeneous catalyst. Adsorption 24, 309–324 (2018). https://doi.org/10.1007/s10450-018-9941-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10450-018-9941-6