Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Production of 2-phenylethyl acetate via reactive distillation

  • 11 Accesses

Abstract

An alternative approach to 2-phenylethyl acetate production, reactive distillation process for 2-phenylethyl acetate production from 2-phenylethanol in the presence of an inert component, n-pentane, via esterification by acetic acid is presented. The main objectives of this work were shifting of the chemical equilibrium in favour of the desired product and achieving the required product purity. In the first step, graphical mapping methods were employed to evaluate reactive distillation applicability for 2-phenylethanol esterification. To describe the system phase equilibria, thermodynamic model NRTL-HOC was used. Process feasibility was evaluated using a boiling point analysis and residue curves maps, and the process operating window was estimated. Results show that the reactive distillation concept can be used for 2-phenylethyl acetate production as suitable product compositions without serious process limitations were predicted. Total equilibrium model (phase and chemical equilibria) was used for reactive distillation column calculations performed by the Aspen Plus software. Reactive distillation column parameters were calculated and optimised according to the design criteria. Finally, optimised reactive distillation column parameters were used for temperature and concentration profile evaluation. These results form a promising base for further steps in the design of 2-phenylethyl acetate production via reactive distillation.

This is a preview of subscription content, log in to check access.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17

Abbreviations

D :

Distillate

f :

Feed-stage position

F :

Feed

K a :

Chemical equilibrium constant

:

Mass flow (kg h1)

Δṅ :

Reactant consumption (kmol h1)

N :

Number of theoretical stages including reboiler and condenser

N R :

Number of reactive stages

P :

Total pressure (kPa)

\(\dot{Q}_{{\text{C}}}\) :

Condenser duty (kW)

\(\dot{Q}_{{\text{W}}}\) :

Reboiler duty (kW)

R :

Reflux ratio

t :

Temperature (°C)

t b :

Boiling temperature at atmospheric pressure (°C)

w :

Mass fraction

W :

Distillation bottom product

x :

Mole fraction in the liquid phase

X :

Conversion

y :

Mole fraction in the vapour phase

AA:

Acetic acid

b :

Boiling

C :

Condenser

C5 :

n-Pentane

F:

Feed

H2O:

Water

PE:

2-Phenylethanol

PEA:

2-Phenylethyl acetate

W :

Reboiler

AA:

Acetic acid

C5 :

n-Pentane

EQ-KIN:

Equilibrium stage model with reaction kinetics

HOC:

Hayden–O'Connell equation of state

LL:

Liquid–liquid

MBSE:

Bioreactor-membrane based solvent extraction

NEQ:

Non-equilibrium stage model with effective diffusion coefficients

NEQ-MS:

Non-equilibrium stage model applying Maxwell–Stephan equations

NRTL:

Non-random two liquids

PE:

2-Phenylethanol

PEA:

2-Phenylethyl acetate

RD:

Reactive distillation

RK:

Redlich–Kwong equation of state

TEQ:

Total equilibrium stage model

VL:

Vapour–liquid

VLE:

Vapour–liquid-phase equilibria

VLL:

Vapour–liquid–liquid

References

  1. Akkaravathasinp S, Narataruksa P, Prapainainar C (2015) The effect of feed location of a semi-batch reactive distillation via esterification reaction of acetic acid and methanol: simulation study, energy procedia. Elsevier, Amsterdam. https://doi.org/10.1016/j.egypro.2015.11.566

  2. ASPEN Technology (2000) Aspen Plus®: Aspen Plus user guide, version 10.2. Aspen Technology Inc., Cambridge

  3. Białecka-Florjańczyk E, Krzyczkowska J, Stolarzewicz I, Kapturowska A (2012) Synthesis of 2-phenylethyl acetate in the presence of Yarrowia lipolytica KKP 379 biomass. J Mol Catal B Enzym 74(3–4):241–245. https://doi.org/10.1016/j.molcatb.2011.10.010

  4. Calvar N, González B, Dominguez A (2007) Esterification of acetic acid with ethanol: reaction kinetics and operation in a packed bed reactive distillation column. Chem Eng Process 46(12):1317–1323. https://doi.org/10.1016/j.cep.2006.10.007

  5. Feyzi V, Beheshti M (2017) Chemical engineering and processing: process intensification exergy analysis and optimization of reactive distillation column in acetic acid production process. Chem Eng Process 120:161–172. https://doi.org/10.1016/j.cep.2017.06.016

  6. Gao X, Zhao Y, Li H, Li XG (2018) Review of basic and application investigation of reactive distillation technology for process intensification. CIESC J 69(1):218–238

  7. Green DW, Perry RH (2008) Perry's chemical engineers' handbook, thermodynamics, 8th edn. McGrawHill, New York

  8. Hanika JH, Kolena JH, Smejkal Q (1999) Butylacetate via reactive distillation—modelling and experiment. Chem Eng Sci 54:5205–5209. https://doi.org/10.1016/s0009-2509(99)00241-9

  9. Hanika JH, Smejkal Q, Kolena JH (2001) 2-Methylpropylacetate synthesis via catalytic distillation. Catal Today 66(2–4):219–223. https://doi.org/10.1016/S0920-5861(00)00652-0

  10. Herington EFG (1947) A thermodynamic test for the internal consistency of experimental data on volatility ratios. Nature 160:610–611. https://www.nature.com/articles/160610b0

  11. Herington EFG (1951) Tests for the consistency of experimental isobaric vapour–liquid equilibrium data. J Inst Pet 37:457–470

  12. Hertel MO, Scheuren H, Sommer KJ (2007) Solubilities of hexanal, benzaldehyde, 2-furfural, 2-phenylethanol, phenylethanal, and c-nonalactone in water at temperatures between 50 and 100 °C. J Chem Eng Data 52:2143–2145. https://doi.org/10.1021/je700122y

  13. Kiss AA (2013) Advanced distillation technologies: designcontrol and applications. Wiley, New York

  14. Kotora M, Švandová Z, Markoš J (2009) A three-phase nonequilibrium model for catalytic distillation. Chem Pap 63:197–204. https://doi.org/10.2478/s11696-009-0004-z

  15. Krishna R (2002) Reactive separation: more ways how to skin a cat. Chem Eng Sci 57:1491–1504. https://doi.org/10.1016/S0009-2509(02)00020-9

  16. Lee H, Hsiao T (2017) Design and simulation of reactive distillation processes, epigenetic biomarkers and diagnostics. Elsevier Inc, New York. https://doi.org/10.1016/B978-0-12-803782-9.00014-5

  17. Li C, Duan C, Fang J, Li H (2019) Process intensification and energy saving of reactive distillation for production of ester compounds. Chin J Chem Eng 27:1307–1323. https://doi.org/10.1016/j.cjche.2018.10.007

  18. Marek J (1955) Liquid-vapor equilibriums in systems containing an associating substance: III the system water + acetic acid + acetic anhydride and the corresponding binary systems at 400 mm mercury. Chemické Listy 49:1756–1766

  19. Martínez-Avila O, Sánchez-Xavier A, Font X, Barrena R (2018) Bioprocesses for 2-phenylethanol and 2-phenylethyl acetate production: current state and perspectives. Appl Microbiol Biotechnol 102(33):9991–10004. https://doi.org/10.1007/s00253-018-9384-8

  20. Miháľ M, Vereš R, Markoš J (2012) Investigation of 2-phenylethanol production in fed-batch hybrid reactor: membrane extraction and microfiltration. Sep Purif Technol 95:126–135. https://doi.org/10.1016/j.seppur.2012.04.030

  21. Miháľ M, Červeňanský I, Markoš J (2016) Production of phenylacetic acid from l-phenylalanine in dual reactor membrane hybrid system. Chem Eng Process 110:114–122. https://doi.org/10.1016/j.cep.2016.10.008

  22. Mokraoui S, Coquelet C, Valtz A, Hegel PE, Richon D (2007) New solubility data of hydrocarbons in water and modeling concerning vapor–liquid–liquid binary systems. Ind Eng Chem Res 46:9257–9262. https://doi.org/10.1021/ie070858y

  23. Muthia R, Reijneveld A, van der Ham A, ten Kate A, Bargeman G, Kersten S, Kiss AA (2018) Novel method for mapping the applicability of reactive distillation, chemical engineering and processing—process intensification. Elsevier 128:263–275. https://doi.org/10.1016/j.cep.2018.04.001

  24. Niesbach A, Kuhlmann H, Keller T, Lutze P, Górak A (2013) Optimisation of industrial-scale n-butyl acrylate production using reactive distillation. Chem Eng Sci 100:360–372. https://doi.org/10.1016/j.ces.2013.01.035

  25. Reid RC, Prausnitz JM, Poling BE (1988) The properties of gases and liquids, 4th edn. McGrow-Hill Book Company, New York (International Edition)

  26. Renon H, Prausnitz JM (1968) Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J 14(1):135–144. https://doi.org/10.1002/aic.690140124

  27. Schembecker G, Tlatlik S (2003) Process synthesis for reactive separations. Chem Eng Process Process Intesification 42:179–189. https://doi.org/10.1016/S0255-2701(02)00087-9

  28. Schlosser Š, Kertéz R, Marták J (2005) Recovery and separation of organic acids by membrane-based solvent extraction and pertraction. An overview with a case study in recovery of MPCA. Rev Sep Purif Technol 41:237–266. https://doi.org/10.1016/j.seppur.2004.07.019

  29. Sherwin MB, Brownstein AM, Peress J (1979) Preparation of 2-phenylethanol and 2-phenylethyl acetate, EU Patent no. EP0004732B1, European Patent Office.

  30. Singh D, Gupta RK, Kumar V (2015) Simulation of a plant scale reactive distillation column for esterification of acetic acid. Comput Chem Eng 73:70–81. https://doi.org/10.1016/j.compchemeng.2014.11.007

  31. Smejkal Q, Kolena JH, Hanika J (2009) Ethyl acetate synthesis by coupling of fixed-bed reactor and reactive distillation column—process integration aspects. Chem Eng J 154(1–3):236–240. https://doi.org/10.1016/j.cej.2009.04.022

  32. Stephenson RM, Stuart JJ (1986) Mutual binary solubilities: water–alcohols and water–esters. Chem Eng Data 31:56. https://doi.org/10.1021/je00043a019

  33. Subawalla H, Fair JR (1999) Design guidelines for solid-catalyzed reactive distillation systems. Ind Eng Chem Res 38(10):3696–3709. https://doi.org/10.1021/ie990008l

  34. Sundmacher K, Kienle A (2002) Reactive distillation, status a future directions. Wiley-VCHVerlag GmbH & Co. KGaA, Weinheim

  35. Tavan Y, Behbahani RM, Hosseini SH (2013) A novel intensified reactive distillation process to produce pure ethyl acetate in one column—part I: parametric study. Chem Eng Process 73:81–86. https://doi.org/10.1016/j.cep.2013.05.015

  36. Taylor R, Krishna R (2000) Modelling reactive distillation. Chem Eng Sci 55:5183–5229. https://doi.org/10.1016/S0009-2509(00)00120-2

  37. Vargai P, Červeňanský I, Miháľ M, Markoš J (2018) Design of hybrid systems with in-situ product removal from fermentation broth: case study for 2-phenylethanol production. Chem Eng Process Process Intensification 134:58–71. https://doi.org/10.1016/j.cep.2018.10.011

  38. Wierschem M, Górak A (2018) Reactive distillation, reference module in chemistry, molecular sciences and chemical engineering. Elsevier Inc, New York. https://doi.org/10.1016/B978-0-12-409547-2.14066-1

  39. Xueliang J, Lei Z, Hongxia C, Hong J, Shuangzhi L, Zhaozhong S, Yan J (2013) Phenylethyl acetate synthesis method, CN103553914A, China

Download references

Acknowledgements

This work was supported by the Slovak Scientific Agency, Grant no. VEGA 1/0659/18; the Slovak Research and Development Agency under contract No. APVV-16-0111 and by the Slovak Research and Development Agency under contract No. APVV-18-0134.

Author information

Correspondence to Jozef Markoš.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Šulgan, B., Labovská, Z. & Markoš, J. Production of 2-phenylethyl acetate via reactive distillation. Chem. Pap. (2020). https://doi.org/10.1007/s11696-020-01082-9

Download citation

Keywords

  • Reactive distillation
  • Proper model selection
  • Reaction equilibrium approach
  • VLL equilibria
  • Aspen Plus simulation
  • 2-Phenylethyl acetate