Abstract
The reaction of acrylic acid and 2-ethyl-1 hexanol was explored in this work with the intent of process intensification. In order to assess the effect of important parameters on the course of reaction, this work initially conducted batch reactor experiments. Reaction conditions in the batch reactor for a specific conversion (~ 30 %) were obtained. A kinetic model was then obtained through regression to arrive at a rate expression that is later used in process development. Experiments were performed in the reactive distillation (RD) environment in batch mode, which showed substantial increase in conversion (~ 80 %) indicating the applicability of RD. Further, this work performed simulation in the RD environment to assess process intensification. Simulations show that it is possible to obtain complete conversion of the acid.
References
Ahlbrecht, A., H. Brown, and S. Samuel, 1957. Fluorocarbon Acrylate and Methacrylate Esters and Polymers. US Patent, 2803615.Suche in Google Scholar
Ahmad, M., M. Kamaruzzaman, and S. Chin. 2014. “New Method for Acrylic Acid Recovery from Industrial Waste Water via Esterification With2-Ethyl Hexanol.” Proceedings Safety and Environment Protection 96(6): 522–531. Doi: doi:10.1016/j.psep.2014.05.004.Suche in Google Scholar
Altıokka, M., and E. Odes. 2009. “Reaction Kinetics of the Catalytic Esterification of Acrylic Acid with Propylene Glycol.” Appied Catalysis A: General 362: 115–120. Doi: doi:10.1016/j.apcata.2009.04.028.Suche in Google Scholar
Aragon, J., J. Vegas, and L. Jodra. 1993. “Catalytic Behavior of Macroporous Resins in Catalytic Processes with Water Production. Activation and Inhibition Effects in the Kinetics of the Self-Condensation of Cyclohexanone.” Industrial Engineering Chemical Researcher 32: 2555–2562. Doi: 10.1021/ie00023a019Suche in Google Scholar
Aragon, J., J. Vegas, and L. Jodra. 1994. “Self-Condensation of Cyclohexanone Catalyzed by Amberlyst-15. Study of Diffusional Resistances and Deactivation of the Catalyst.” Industrial Engineering Chemical Researcher 33: 592–599. DOI: 10.1021/ie00027a016.Suche in Google Scholar
Balak, J., and M. Polievka. 1983. “Kinetic Esterification of Methacrylic Acid with a Mixture of Methanol and Water in the Presence of Sulfuric Acid.” Chemical Zvesti 37(1): 71–81.Suche in Google Scholar
Balakrishnan, T., and V. Rajendran. 1997. “Polymer-Supported Reagents. II. Kinetics of Esterification of Acrylic Acid with n-Butanol Using Polymer Supported Titanium Tetrachloride as Catalyst.” Journal Polymer Science Particle A: Polymer Chemical 35 (4): 727–733. DOI: 10.1002/(SICI)1099-0518(199703)35:4<727::AID-POLA17>3.0.CO;2-P.Suche in Google Scholar
Bessalem, J., M. Fauconet, and L. Stephane, 2003. Process for the Manufacture of 2 Ethyl Hexyl Acrylate. US patent, 6603036.Suche in Google Scholar
Charelishvili, B., A. Berlin, G. Lyubimova, and M. Gusev. 1978. “Esterification in Solution. The Reaction of Methacrylic Acid with Glycols.” Reactions Kinetics Catal Letters 9: 245–249. Doi: 10.1007/BF02070494Suche in Google Scholar
Chen, X., Z. Xu, and T. Okuhara. 1990. “Liquid Phase Esterification of Acrylic Acid with 1-Butanol Catalyzed by Solid Acid Catalysts.” Appied Catalysis A: General 180: 261–269. Doi: 10.1016/S0926-860X(98)00337-8Suche in Google Scholar
Chien, I., K. Chen, and L. Kuo. 2007. “Overall Control Strategy of a Coupled Reactor/Columns Process for the Production of Ethyl Acrylate.” Journal Proceedings Control 18: 215–231. Doi: 10.1016/j.jprocont.2007.02.006Suche in Google Scholar
Chin, S., M. Ahmad, M. Kamaruzaman, and C. Cheng. 2015. “Kinetic Studies of the Esterification of Pure and Dilute Acrylic Acid with 2-Ethyl Hexanol Catalysed by Amberlyst 15.” Chemical Engineering Sciences 129: 116–125. Doi: 10.1016/j.ces.2015.02.006.Suche in Google Scholar
Dupont, P., J. Vedrine, E. Paumard, G. Hecquet, and F. Lefebvre. 1995. “Hetero-Poly-Acids Supported on Activated Carbon as Catalysts for the Esterification of Acrylic Acid by Butanol.” Appied Catalysis A: General 129(2): 217–227. Doi: 10.1016/0926-860X(95)00099-2Suche in Google Scholar
Essayem, N., V. Martin, A. Riondel, and J Vedrine. 2007. “Esterification of Acrylic Acid with But-1-Ene over Sulfated Fe- and Mn-Promoted Zirconia.” Appied Catalysis A: General 326: 74–81. Doi: 10.1016/j.apcata.2007.03.038Suche in Google Scholar
Fisher, G., and A. MacLean, 1959. Esterification of Acrylic Acid with Methanol. US Patent, 2916512.Suche in Google Scholar
Fogler, H. 1999. “Elements of Chemical Reaction Engineering Third Ed.” Prentice Hall 758–760.Suche in Google Scholar
Guttmann, A. and R. Grasselli. 1983. “Esterification of Methacrylic Acid with Methyl Tertiary Butyl Ether - a Process for the Manufacture of Methyl Methacrylate.” Appications CAT 8(14): 57–70. Doi: 10.1016/0166-9834(83)80053-0.Suche in Google Scholar
Hagiopol, C., 2004. Styrene-Acrylate Copolymer Composition Suitable for Surface Size. US Patent, 6734232.Suche in Google Scholar
Hao, X., A. Yoshida, and J. Nishikido. 2004. “Hf(N(SO2C8F17)2)4 as a Highly Active and Recyclable Lewis Acid Catalyst for Direct Esterification of Methacrylic Acid with Methanol in a Fluorous Biphase System.” Green Chemical 6(11): 566–569. Doi: 10.1039/B409692DSuche in Google Scholar
Hiwale, R., N. Bhate, Y. S. Mahajan, and S. Mahajani. 2004. “Industrial Applications of Reactive Distillation: Recent Trends, Int.” Journal Chemical Reactions Engineering 2(R1): 1–55. Doi: 10.2202/1542-6580.1109Suche in Google Scholar
Iizuka, T., S. Fujie, T. Ushikubo, Z. Chen, and K. Tanabe. 1986. “Esterification of Acrylic Acid with Methanol over Niobic Acid Catalyst.” Appications CAT 28: 1–5. Doi: 10.1016/S0166-9834(00)82488-4.Suche in Google Scholar
Komon, T., P. Niewiadomskia, P. Oracz, and M. Jamroz. 2013. “Esterification of Acrylic Acid with 2-Ethylhexan-1-Ol: Thermodynamic and Kinetic Study.” Appied Catalysis A: General 451: 127–136. Doi: 10.1016/j.apcata.2012.11.018Suche in Google Scholar
Mahajan, Y. S., R. Kamath, P. Kumbhar, and S. Mahajani. 2008. “Self-Condensation of Cyclohexanone over Ion Exchange Resin Catalysts: Kinetics and Selectivity Aspects.” Industrial Engineering Chemical Researcher 47: 25–33. Doi: 10.1021/ie061275bSuche in Google Scholar
Moraru, M. D., and C. S. Bildea. 2017. “Process for n-Butyl Acrylate Production Using Reactive Distillation: Design, Control and Economic Evaluation.” Chemical Engineering Researcher Design 125: 130–145.10.1016/j.cherd.2017.06.038.Suche in Google Scholar
Neeb, P., A. Kolloff, S. Koch, and G. Moortgat. 1998. “Rate Constants for the Reactions of Methylvinyl Ketone, Methacrolein, Methacrylic Acid, and Acrylic Acid with Ozone.” International Journal Chemical Kinetics 30(10): 769–776. Doi: 10.1002/(SICI)1097-4601(1998)30:10<769::aid-kin9>3.0.CO;2-TSuche in Google Scholar
Niesbach, A., J. Daniels, B. Lutze, and A. Górak. 2013. “The Inhibition of Acrylic Acid and Acrylate Ester Polymerization in a Heterogeneously Catalyzed Pilot-Scale Reactive Distillation Column Chem.” Engineering Sciences 88: 95–107. Doi: 10.1016/j.ces.2012.10.029Suche in Google Scholar
Niesbach, A., R. Ron Fuhrmeister, T. Keller, P. Lutze, and A. Górak. 2012. “Esterification of Acrylic Acid and n-Butanol in a Pilot-Scale Reactive Distillation Column: Experimental Investigation, Model Validation and Process Analysis.” Industrial Engineering Chemical Researcher 51: 16444–16456. Doi: 10.1021/ie301934wSuche in Google Scholar
Notay, J., S. Dahiwale, and S. Bhagade. 2003. “Selective Esterification of Tri-Ethylene Glycol with Methacrylic Acid Using Methane Sulphonic Acid.” Industrial Journal Chemical Technical 10: 324–325. ISSN: 0971-457X.Suche in Google Scholar
Nowak, P. 1996. “Kinetics of the Liquid Phase Esterification of Acrylic Acid with N-Octanol and 2-Ethylhexanol Catalyzed by Sulfuric Acid.” Reactions Kinetics Catal Letters 66: 375–380. Doi: 10.1007/BF02475815Suche in Google Scholar
Pal, K., A. Banthia, and D. Majumdar. 2005. “Esterification of Carboxy - Methyl Cellulose with Acrylic Acid for Targeted Drug Delivery System. Trends Biomater.” Artificial Organs 19(1): 12–14.Suche in Google Scholar
Park, D., S. Haam, S. AhnI, T. Lee, H. Kim, and W. Kim. 2003. “Enzymatic Esterification of β-methyl - Glucoside with Acrylic/Methacrylic Acid in Organic Solvents.” Journal Biotechnic 107: 151–160. Doi: 10.1016/j.jbiotec.2003.09.004Suche in Google Scholar
Pascoe, R., and Ohio Marysville, 1988. Continuous Esterification of Methacrylic Acid and Product Recovery. US patent, 4733004.Suche in Google Scholar
Saha, B., and M. Sharma. 1996. “Esterification of Formic Acid, Acrylic Acid and Methacrylic Acid with Cyclohexene in Batch and Distillation Column Reactors: Ion-Exchange Resins as Catalysts.” Reactions Function Pol 28: 263–278. Doi: 10.1016/1381-5148(95)00092-5Suche in Google Scholar
Saha, B., and M. Sharma. 1997. “Reaction of Di - Cyclo - Pentadiene with Formic Acid and Chloro - Acetic Acid with and without Cation-Exchange Resins as Catalysts.” Reactions Function Pol 34: 161–173. Doi: 10.1016/S1381-5148(97)00082-5Suche in Google Scholar
Sert, E., and F. Atalay. 2012. “Esterification of Acrylic Acid with Different Alcohols Catalyzed by Zirconia Supported Tungsto - Phosphoric Acid.” Industrial Engineering Chemical Researcher 51: 6666–6671. Doi: 10.1021/ie202609fSuche in Google Scholar
Sert, E., A. Buluklu, S. Karakus, and F. Atalay. 2013. “Kinetic Study of Catalytic Esterification of Acrylic Acid with Butanol Catalyzed by Different Ion Exchange Resins.” Chemical Engineering Proceedings 73: 23–28. Doi: 10.1021/ie202609f.Suche in Google Scholar
Shinde, V., G. Patil, A. Katariya, and Y. Mahajan. 2015. “Production of Tetrahydrofuran by Dehydration of 1, 4-Butanediol Using Amberlyst-15: Batch Kinetics and Batch Reactive Distillation.” Chemical Engineering Proceedings 95: 241–248. Doi: 10.1016/j.cep.2015.06.016Suche in Google Scholar
Strohlein, G., Y. Assuncao, N. Dube, A. Bardow, M. Mazzotti, and M. Morbidelli. 2006. “Esterification of Acrylic Acid with Methanol by Reactive Chromatography: Experiments and Simulations.” Chemical Engineering Sciences 61: 5296–5306. Doi: doi:10.1016/j.ces.2006.04.004.Suche in Google Scholar
Sun, H., R. Hua, and Y. Yin. 2006. “ZrOCl2·8H2O: An Efficient, Cheap and Reusable Catalyst for the Esterification of Acrylic Acid and Other Carboxylic Acids with Equimolar Amounts of Alcohols.” Molecules 11(4): 263–271. Doi: 10.3390/11040263Suche in Google Scholar PubMed PubMed Central
Talnikar, V., O. Deorukhkar, A. Katariya, and Y. Mahajan. 2017. “Value Added Esterification for the Recovery of Trifluoroacetic Acid: Batch Kinetics and Reactive Distillation Studies.” Chemical Engg Commission 204: 356–364. Doi: 10.1080/00986445.2016.1271795Suche in Google Scholar
Talnikar, V., and Y. Mahajan. 2014. “Recovery of Acids from Dilute Streams: A Review of Process Technologies.” Kor Journal Chemical Engineering 31(10): 1720–1731. Doi: 10.1007/s11814-014-0202-4Suche in Google Scholar
Talwalkar, S., P. Kumbhar, and S. Mahajani. 2006. “Hydration of Di - Cyclopentadiene in the Presence of Cation Exchange Resin.” Industrial Engineering Chemical Researcher 45(24): 8024–8028. Doi: 10.1021/ie060470nSuche in Google Scholar
Taylor, R., and R. Krishna. 2000. “Modeling Reactive Distillation, Chem.” Engineering Sciences 55: 5183–5229. Doi: 10.1016/S0009-2509(00)00120-2Suche in Google Scholar
Web ref 1: “Amberlyst® 15 Hydrogen Form Wet”, accessed on 15 Dec 2017, https://www.lenntech.com/Data-sheets/Amberlyst-15wet-L.pdfSuche in Google Scholar
Web ref 2: Ion Exchange India Limited, “Material Safety Data Sheet”, 2004, accessed on 20 May 2017, http://www.ionresins.com/msds/190%20msds02.pdfSuche in Google Scholar
Web ref 3: Thermax Ion Exchange Resin, “Summarized Data Sheet” 2016, accessed on 20 May 2017, http://www.thermaxglobal.com/thermax-chemicals/pdf/Thermax_ION-Exchange-Resins_SDS-Brochure.pdfSuche in Google Scholar
Web ref 4: Sulzer, “Structured Packings”, 2017, accessed on 20 May 2017, http://www.sulzer.com/en/Products-and-Services/Separation-Technology/Structured-PackingsSuche in Google Scholar
Web ref 5: Hyflux, “Knitted Mesh Structured Column Packing”, 2016, accessed on 20 May 2017, http://www.evergreenindia.comSuche in Google Scholar
Yadav, G., and M. Thathagar. 2002. “Esterification of Maleic Acid with Ethanol over Cation-Exchange Resin Catalysts.” Reactions Function Pol 52: 99–110. Doi: 10.1016/S1381-5148(02)00086-XSuche in Google Scholar
Yang, J., S. Cho, J. Park, and K. Lee. 2007. “Esterification of Acrylic Acid with 1, 4‑Butanediol in a Batch Distillation Column Reactor over Amberlyst 15 Catalyst.” Canada Journal Chemical Engineering 85: 883–888. DOI: 10.1002/cjce.5450850609.Suche in Google Scholar
Zhyznevskiy, V., V. Gumenetskiy, O. Shyshchak, and Y. Fedevych. 2011. “The Use of Isobutyl Alcohol for Methacrylate Synthesis. Chem.” Chemical Technical 5(3): 277–284.Suche in Google Scholar
© 2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Synthesis and Modification of Zeolite ZSM-5 Catalyst with Solutions of Calcium Carbonate (CaCO3) and Sodium Carbonate (Na2CO3) for Methanol to Gasoline Conversion
- Hydrogen Generation in an Annular Micro-Reactor: An Experimental Investigation and Reaction Modelling by Shrinking Core Model (SCM)
- Fluidization in Supercritical Water: Heat Transfer between Particle and Supercritical Water
- Optimization of Process Parameters for Reactive Separation of Gallic Acid
- Intensification of the Production of 2-Ethyl-Hexyl Acrylate: Batch Kinetics and Reactive Distillation
- Hydrogen Generation in Water Splitting Reaction Using Aluminum: Effect of NaOH Concentration and Reaction Modelling Using SCM
- NOx process inhibition and energy efficiency improvement in new swirl modification device for steel slag based on coal combustion
- Study of Pyrolysis Behavior of Shenhua Coal Pretreated by Ionic Liquid 1-Ethyl-3-Methylimidazolium Acetate
- Catalytic Gasification – A Critical Analysis of Carbon Dioxide Methanation on a Ru/Al2O3 Catalyst
- A Green Process for Synthesis of Geraniol Esters by Immobilized Lipase from Candida Antarctica B Fraction in Non-Aqueous Reaction Media: Optimization and Kinetic Modeling
Artikel in diesem Heft
- Synthesis and Modification of Zeolite ZSM-5 Catalyst with Solutions of Calcium Carbonate (CaCO3) and Sodium Carbonate (Na2CO3) for Methanol to Gasoline Conversion
- Hydrogen Generation in an Annular Micro-Reactor: An Experimental Investigation and Reaction Modelling by Shrinking Core Model (SCM)
- Fluidization in Supercritical Water: Heat Transfer between Particle and Supercritical Water
- Optimization of Process Parameters for Reactive Separation of Gallic Acid
- Intensification of the Production of 2-Ethyl-Hexyl Acrylate: Batch Kinetics and Reactive Distillation
- Hydrogen Generation in Water Splitting Reaction Using Aluminum: Effect of NaOH Concentration and Reaction Modelling Using SCM
- NOx process inhibition and energy efficiency improvement in new swirl modification device for steel slag based on coal combustion
- Study of Pyrolysis Behavior of Shenhua Coal Pretreated by Ionic Liquid 1-Ethyl-3-Methylimidazolium Acetate
- Catalytic Gasification – A Critical Analysis of Carbon Dioxide Methanation on a Ru/Al2O3 Catalyst
- A Green Process for Synthesis of Geraniol Esters by Immobilized Lipase from Candida Antarctica B Fraction in Non-Aqueous Reaction Media: Optimization and Kinetic Modeling