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Published in: Adsorption 3/2018

01-03-2018

Transesterification of propylene glycol methyl ether by reactive simulated moving bed chromatography using homogeneous catalyst

Authors: Jungmin Oh, Balamurali Sreedhar, Megan E. Donaldson, Timothy C. Frank, Alfred K. Schultz, Andreas S. Bommarius, Yoshiaki Kawajiri

Published in: Adsorption | Issue 3/2018

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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.

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Literature
go back to reference Agrawal, G., Kawajiri, Y.: Comparison of various ternary simulated moving bed separation schemes by multi-objective optimization. J Chromatogr A. 1238, 105–113 (2012)CrossRef Agrawal, G., Kawajiri, Y.: Comparison of various ternary simulated moving bed separation schemes by multi-objective optimization. J Chromatogr A. 1238, 105–113 (2012)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference Demirbas, A.: Comparison of transesterification methods for production of biodiesel from vegetable oils and fats. Energy Convers. Manag. 49, 125–130 (2008)CrossRef Demirbas, A.: Comparison of transesterification methods for production of biodiesel from vegetable oils and fats. Energy Convers. Manag. 49, 125–130 (2008)CrossRef
go back to reference Fourer, R., Gay, D.M., Kernighan, B.W.: A modeling language for mathematical-programming. Manag. Sci. 36, 519–554 (1990)CrossRef Fourer, R., Gay, D.M., Kernighan, B.W.: A modeling language for mathematical-programming. Manag. Sci. 36, 519–554 (1990)CrossRef
go back to reference Geier, D., Soper, J.: US Patent US7828978 B2 (2007) Geier, D., Soper, J.: US Patent US7828978 B2 (2007)
go back to reference Gyani, V.C., Mahajani, S.: Reactive chromatography for the synthesis of 2-ethylhexyl acetate. Sep. Sci. Technol. 43, 2245–2268 (2008)CrossRef Gyani, V.C., Mahajani, S.: Reactive chromatography for the synthesis of 2-ethylhexyl acetate. Sep. Sci. Technol. 43, 2245–2268 (2008)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference Kawase, M., Inoue, Y., Araki, T., Hashimoto, K.: The simulated moving-bed reactor for production of bisphenol A. Catal. Today. 48, 199–209 (1999)CrossRef Kawase, M., Inoue, Y., Araki, T., Hashimoto, K.: The simulated moving-bed reactor for production of bisphenol A. Catal. Today. 48, 199–209 (1999)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference Kitagawa, N., Yonemoto, T.: Japanese Patent 2016-059833A (2016) Kitagawa, N., Yonemoto, T.: Japanese Patent 2016-059833A (2016)
go back to reference Kloppenburg, E., Gilles, E.D.: A new concept for operating simulated moving-bed processes. Chem. Eng. Technol. 22, 813–817 (1999)CrossRef Kloppenburg, E., Gilles, E.D.: A new concept for operating simulated moving-bed processes. Chem. Eng. Technol. 22, 813–817 (1999)CrossRef
go back to reference Lee, D.W., Park, Y.M., Lee, K.Y.: Heterogeneous base catalysts for transesterification in biodiesel synthesis. Catal Surv. Asia. 13, 63–77 (2009)CrossRef Lee, D.W., Park, Y.M., Lee, K.Y.: Heterogeneous base catalysts for transesterification in biodiesel synthesis. Catal Surv. Asia. 13, 63–77 (2009)CrossRef
go back to reference Lode, F., Houmard, M., Migliorini, C., Mazzotti, M., Morbidelli, M.: Continuous reactive chromatography. Chem. Eng. Sci. 56, 269–291 (2001)CrossRef Lode, F., Houmard, M., Migliorini, C., Mazzotti, M., Morbidelli, M.: Continuous reactive chromatography. Chem. Eng. Sci. 56, 269–291 (2001)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference Rodrigues, A.E., Pereira, C.S.M., Santos, J.C.: Chromatographic reactors. Chem. Eng. Technol. 35, 1171–1183 (2012)CrossRef Rodrigues, A.E., Pereira, C.S.M., Santos, J.C.: Chromatographic reactors. Chem. Eng. Technol. 35, 1171–1183 (2012)CrossRef
go back to reference Schmidt-Traub, H., Schulte, M., Seidel-Morgenstern, A.: Preparative Chromatography, 2nd edn. Wiley, Weinheim (2012)CrossRef Schmidt-Traub, H., Schulte, M., Seidel-Morgenstern, A.: Preparative Chromatography, 2nd edn. Wiley, Weinheim (2012)CrossRef
go back to reference Schuchardt, U., Sercheli, R., Vargas, R.M.: Transesterification of vegetable oils: a review. J. Braz. Chem. Soc. 9, 199–210 (1998)CrossRef Schuchardt, U., Sercheli, R., Vargas, R.M.: Transesterification of vegetable oils: a review. J. Braz. Chem. Soc. 9, 199–210 (1998)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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) 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)
go back to reference 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)CrossRef 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)CrossRef
go back to reference 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)CrossRef 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)CrossRef
go back to reference Yonemoto, T., Kitagawa, N., Toda, T.: Japanese Patent 2006-104316 (2006) Yonemoto, T., Kitagawa, N., Toda, T.: Japanese Patent 2006-104316 (2006)
go back to reference Yonemoto, T., Kitagawa, N., Nakagawa, Y., Nakayama, M.: Japanese Patent 2010-195938 (2010) Yonemoto, T., Kitagawa, N., Nakagawa, Y., Nakayama, M.: Japanese Patent 2010-195938 (2010)
Metadata
Title
Transesterification of propylene glycol methyl ether by reactive simulated moving bed chromatography using homogeneous catalyst
Authors
Jungmin Oh
Balamurali Sreedhar
Megan E. Donaldson
Timothy C. Frank
Alfred K. Schultz
Andreas S. Bommarius
Yoshiaki Kawajiri
Publication date
01-03-2018
Publisher
Springer US
Published in
Adsorption / Issue 3/2018
Print ISSN: 0929-5607
Electronic ISSN: 1572-8757
DOI
https://doi.org/10.1007/s10450-018-9941-6

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