Skip to main content
Erschienen in: Adsorption 4/2019

11.03.2019

Experimental evaluation of simulated moving bed reactor for transesterification reaction synthesis of glycol ether ester

verfasst von: Shan Tie, Balamurali Sreedhar, Megan Donaldson, Timothy Frank, Alfred K. Schultz, Andreas S. Bommarius, Yoshiaki Kawajiri

Erschienen in: Adsorption | Ausgabe 4/2019

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

This work presents an experimental evaluation of multi-column simulated moving bed reactor (SMBR) technology for transesterification of glycol ether ester for the first time. An industrially relevant solvent, propylene glycol methyl ether acetate (DOWANOL™ PMA) was produced using a laboratory-scale SMBR unit packed with a base catalyst. The catalyst selected in this study, a Type-II anion exchange resin, was found to be resistant to deactivation through our experimental runs. To design the SMBR process, single-column experiments were first carried out to develop a mathematical model and estimate model parameters. Using this model, the optimal SMBR process was found by a multi-objective optimization technique to maximize the productivity while achieving high conversions. The optimal operating conditions found in this manner were implemented in the lab-scale SMB unit, which achieved conversions ranging from 47.3 to 57.7%. Furthermore, using the experimental data obtained from these experimental runs, the prediction of the model was improved via Tikhonov regularization, which was successfully validated in an additional run at an even higher conversion of 74.6%.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
Zurück zum Zitat 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)CrossRefPubMed 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)CrossRefPubMed
Zurück zum Zitat Bentley, J., Sloan, C., Kawajiri, Y.: Simultaneous modeling and optimization of nonlinear simulated moving bed chromatography by the prediction–correction method. J. Chromatogr. A 1280, 51–63 (2013)CrossRefPubMed Bentley, J., Sloan, C., Kawajiri, Y.: Simultaneous modeling and optimization of nonlinear simulated moving bed chromatography by the prediction–correction method. J. Chromatogr. A 1280, 51–63 (2013)CrossRefPubMed
Zurück zum Zitat Darnoko, D., Cheryan, M.: Kinetics of palm oil transesterification in a batch reactor. J. Am. Oil Chem. Soc. 77, 1263–1267 (2000)CrossRef Darnoko, D., Cheryan, M.: Kinetics of palm oil transesterification in a batch reactor. J. Am. Oil Chem. Soc. 77, 1263–1267 (2000)CrossRef
Zurück zum Zitat Fourer, R., Gay, D.M., Kernighan, W.: MPL. A Modeling Language for Mathematical Programming. Brooks/Cole Publishing Company, CA (2002) Fourer, R., Gay, D.M., Kernighan, W.: MPL. A Modeling Language for Mathematical Programming. Brooks/Cole Publishing Company, CA (2002)
Zurück zum Zitat Frank, T.C., Donaldson, M.E.: International Patent Application WO2014179706 (2016) Frank, T.C., Donaldson, M.E.: International Patent Application WO2014179706 (2016)
Zurück zum Zitat Fukuda, H., Kondo, A., Noda, H.: Biodiesel fuel production by transesterification of oils. J. Biosci. Bioeng. 92, 405–416 (2001)CrossRefPubMed Fukuda, H., Kondo, A., Noda, H.: Biodiesel fuel production by transesterification of oils. J. Biosci. Bioeng. 92, 405–416 (2001)CrossRefPubMed
Zurück zum Zitat Geier, D., Soper, J.G.: United States Patent US 7828978B2, (2010) Geier, D., Soper, J.G.: United States Patent US 7828978B2, (2010)
Zurück zum Zitat 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
Zurück zum Zitat 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
Zurück zum Zitat Hsieh, C.-T., Lee, M.-J., Lin, H.: Multiphase equilibria for mixtures containing acetic acid, water, propylene glycol monomethyl ether, and propylene glycol methyl ether acetate. Ind. Eng. Chem. Res. 45, 2123–2130 (2006)CrossRef Hsieh, C.-T., Lee, M.-J., Lin, H.: Multiphase equilibria for mixtures containing acetic acid, water, propylene glycol monomethyl ether, and propylene glycol methyl ether acetate. Ind. Eng. Chem. Res. 45, 2123–2130 (2006)CrossRef
Zurück zum Zitat Johnson, S.H., Wright, H.N.: United States Patent US 3700726A (1972) Johnson, S.H., Wright, H.N.: United States Patent US 3700726A (1972)
Zurück zum Zitat Kametaka, N., Marumo, K., Tokuda, K., Sekiguchi, K.: United States Patent US 4260813A (1981) Kametaka, N., Marumo, K., Tokuda, K., Sekiguchi, K.: United States Patent US 4260813A (1981)
Zurück zum Zitat Karayannidis, G.P., Achilias, D.S., Sideridou, I.D., Bikiaris, D.N.: Alkyd resins derived from glycolized waste poly(ethylene terephthalate). Eur. Polym. J. 41, 201–210 (2005)CrossRef Karayannidis, G.P., Achilias, D.S., Sideridou, I.D., Bikiaris, D.N.: Alkyd resins derived from glycolized waste poly(ethylene terephthalate). Eur. Polym. J. 41, 201–210 (2005)CrossRef
Zurück zum Zitat Kawajiri, Y., Biegler, L.T.: Nonlinear programming superstructure for optimal dynamic operations of simulated moving bed processes. Ind. Eng. Chem. Res. 45, 8503–8513 (2006)CrossRef Kawajiri, Y., Biegler, L.T.: Nonlinear programming superstructure for optimal dynamic operations of simulated moving bed processes. Ind. Eng. Chem. Res. 45, 8503–8513 (2006)CrossRef
Zurück zum Zitat Kawase, M., Suzuki, T.B., Inoue, K., Yoshimoto, K., Hashimoto, K.: Increased esterification conversion by application of the simulated moving bed reactor. Chem. Eng. Sci. 51, 2971–2976 (1996)CrossRef Kawase, M., Suzuki, T.B., Inoue, K., Yoshimoto, K., Hashimoto, K.: Increased esterification conversion by application of the simulated moving bed reactor. Chem. Eng. Sci. 51, 2971–2976 (1996)CrossRef
Zurück zum Zitat Martello, M.T., Burns, A., Hillmyer, M.: Bulk ring-opening transesterification polymerization of the renewable δ-decalactone using an organocatalyst. ACS Macro Lett 1, 131–135 (2012)CrossRef Martello, M.T., Burns, A., Hillmyer, M.: Bulk ring-opening transesterification polymerization of the renewable δ-decalactone using an organocatalyst. ACS Macro Lett 1, 131–135 (2012)CrossRef
Zurück zum Zitat Mazzotti, M., Neri, B., Gelosa, D., Morbidelli, M.: Dynamics of a chromatographic reactor: esterification catalyzed by acidic resins. Ind. Eng. Chem. Res. 36, 3163–3172 (1997)CrossRef Mazzotti, M., Neri, B., Gelosa, D., Morbidelli, M.: Dynamics of a chromatographic reactor: esterification catalyzed by acidic resins. Ind. Eng. Chem. Res. 36, 3163–3172 (1997)CrossRef
Zurück zum Zitat Meher, L.C., Sagar, V., Naik, D.: S.N.: Technical aspects of biodiesel production by transesterification—a review. Renew. Sust. Energ. Rev. 10, 248–268 (2006)CrossRef Meher, L.C., Sagar, V., Naik, D.: S.N.: Technical aspects of biodiesel production by transesterification—a review. Renew. Sust. Energ. Rev. 10, 248–268 (2006)CrossRef
Zurück zum Zitat Noshadi, I., Amin, N.A.S., Parnas, R.S.: Continuous production of biodiesel from waste cooking oil in a reactive distillation column catalyzed by solid heteropolyacid: optimization using response surface methodology (RSM). Fuel 94, 156–164 (2012)CrossRef Noshadi, I., Amin, N.A.S., Parnas, R.S.: Continuous production of biodiesel from waste cooking oil in a reactive distillation column catalyzed by solid heteropolyacid: optimization using response surface methodology (RSM). Fuel 94, 156–164 (2012)CrossRef
Zurück zum Zitat Oh, J.: Development of reactive chromatography system for equilibrium-limited reactions. Ph.D. Thesis, School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA, USA (2016) Oh, J.: Development of reactive chromatography system for equilibrium-limited reactions. Ph.D. Thesis, School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA, USA (2016)
Zurück zum Zitat 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
Zurück zum Zitat 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)CrossRefPubMed 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)CrossRefPubMed
Zurück zum Zitat Pöpken, T., Steinigeweg, S., Gmehling, J.: Synthesis and hydrolysis of methyl acetate by reactive distillation using structured catalytic packings: experiments and simulation. Ind. Eng. Chem. Res. 40, 1566–1574 (2001)CrossRef Pöpken, T., Steinigeweg, S., Gmehling, J.: Synthesis and hydrolysis of methyl acetate by reactive distillation using structured catalytic packings: experiments and simulation. Ind. Eng. Chem. Res. 40, 1566–1574 (2001)CrossRef
Zurück zum Zitat Ren, Y., He, B., Yan, F., Wang, H., Cheng, Y., Lin, L., Feng, Y., Li, J.: Continuous biodiesel production in a fixed bed reactor packed with anion-exchange resin as heterogeneous catalyst. Bioresour. Technol. 113, 19–22 (2012)CrossRefPubMed Ren, Y., He, B., Yan, F., Wang, H., Cheng, Y., Lin, L., Feng, Y., Li, J.: Continuous biodiesel production in a fixed bed reactor packed with anion-exchange resin as heterogeneous catalyst. Bioresour. Technol. 113, 19–22 (2012)CrossRefPubMed
Zurück zum Zitat Sainio, T., Kaspereit, M., Kienle, A., Seidel-Morgenstern, A.: Thermal effects in reactive liquid chromatography. Chem. Eng. Sci. 62, 5674–5681 (2007)CrossRef Sainio, T., Kaspereit, M., Kienle, A., Seidel-Morgenstern, A.: Thermal effects in reactive liquid chromatography. Chem. Eng. Sci. 62, 5674–5681 (2007)CrossRef
Zurück zum Zitat Seidel-Morgenstern, A., Keßler, L.C., Kaspereit, M.: New Developments in simulated moving bed chromatography. Chem. Eng. Technol. 31, 826–837 (2008)CrossRef Seidel-Morgenstern, A., Keßler, L.C., Kaspereit, M.: New Developments in simulated moving bed chromatography. Chem. Eng. Technol. 31, 826–837 (2008)CrossRef
Zurück zum Zitat Shibasaki-Kitakawa, N., Honda, H., Kuribayashi, H., Toda, T., Fukumura, T., Yonemoto, T.: Biodiesel production using anionic ion-exchange resin as heterogeneous catalyst. Bioresour. Technol. 98, 416–421 (2007)CrossRefPubMed Shibasaki-Kitakawa, N., Honda, H., Kuribayashi, H., Toda, T., Fukumura, T., Yonemoto, T.: Biodiesel production using anionic ion-exchange resin as heterogeneous catalyst. Bioresour. Technol. 98, 416–421 (2007)CrossRefPubMed
Zurück zum Zitat Shuit, S.H., Lee, K.T., Kamaruddin, A.H., Yusup, S.: Reactive extraction and in situ esterification of Jatropha curcas L. seeds for the production of biodiesel. Fuel 89, 527–530 (2010)CrossRef Shuit, S.H., Lee, K.T., Kamaruddin, A.H., Yusup, S.: Reactive extraction and in situ esterification of Jatropha curcas L. seeds for the production of biodiesel. Fuel 89, 527–530 (2010)CrossRef
Zurück zum Zitat Steinigeweg, S., Gmehling, J.: Transesterification processes by combination of reactive distillation and pervaporation. Chem. Eng. Process. 43, 447–456 (2004)CrossRef Steinigeweg, S., Gmehling, J.: Transesterification processes by combination of reactive distillation and pervaporation. Chem. Eng. Process. 43, 447–456 (2004)CrossRef
Zurück zum Zitat Tie, S., Sreedhar, B., Agrawal, G., Oh, J., Donaldson, M.E., Frank, T.C., Schultz, A.K., Bommarius, A.S., 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., Donaldson, M.E., Frank, T.C., Schultz, A.K., Bommarius, A.S., 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
Zurück zum Zitat Tie, S., Sreedhar, B., Donaldson, M., Frank, T., Schultz, A., Bommarius, A., Kawajiri, Y.: Process integration for simulated moving bed reactor for production of glycol ether acetate. Chemical engineering processing—process intensification (in press) Tie, S., Sreedhar, B., Donaldson, M., Frank, T., Schultz, A., Bommarius, A., Kawajiri, Y.: Process integration for simulated moving bed reactor for production of glycol ether acetate. Chemical engineering processing—process intensification (in press)
Zurück zum Zitat Tikhonov, A., Goncharsky, A., Stepanov, V., Yagola, A.: Numerical Methods for the Solution of Ill-Posed Problems. Kluwer Academic Publishers, Boston (1995)CrossRef Tikhonov, A., Goncharsky, A., Stepanov, V., Yagola, A.: Numerical Methods for the Solution of Ill-Posed Problems. Kluwer Academic Publishers, Boston (1995)CrossRef
Zurück zum Zitat Wächter, 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 Wächter, 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
Zurück zum Zitat Zakaria, R., Harvey, A.P.: Direct production of biodiesel from rapeseed by reactive extraction/in situ transesterification. Fuel Process. Technol. 102, 53–60 (2012)CrossRef Zakaria, R., Harvey, A.P.: Direct production of biodiesel from rapeseed by reactive extraction/in situ transesterification. Fuel Process. Technol. 102, 53–60 (2012)CrossRef
Metadaten
Titel
Experimental evaluation of simulated moving bed reactor for transesterification reaction synthesis of glycol ether ester
verfasst von
Shan Tie
Balamurali Sreedhar
Megan Donaldson
Timothy Frank
Alfred K. Schultz
Andreas S. Bommarius
Yoshiaki Kawajiri
Publikationsdatum
11.03.2019
Verlag
Springer US
Erschienen in
Adsorption / Ausgabe 4/2019
Print ISSN: 0929-5607
Elektronische ISSN: 1572-8757
DOI
https://doi.org/10.1007/s10450-019-00048-y

Weitere Artikel der Ausgabe 4/2019

Adsorption 4/2019 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.