Flowsheets for hydroxyacetone–phenol binary mixture separation: The use of special distillation methods

Objectives. To study the possibility of hydroxyacetone–phenol binary mixture (a constituent of a mixture of phenol production by the cumene method) separation in flowsheets based on the use of distillation special methods. This is the addition of separating agents to increase the relative volatility of the components of the original mixture, and the variation of pressure in the columns.

Methods. A computational simulation in Aspen Plus® was used as the research method. Mathematical modeling of the vapor–liquid equilibrium was carried out using a local compositions model Non-Random Two Liquid. The viability of the latter was confirmed by comparing experimental and calculated on phase equilibrium data, and azeotropic data. The average relative error does not exceed 3%.

Results. The dependence of the composition and boiling point of the hydroxyacetone–phenol azeotrope on pressure was determined in a computational experiment (as the pressure increases, the azeotrope is enriched with phenol). The possibility of using a complex of columns operating under different pressures to separate the mixture was shown (the shift of the azeotrope is about 9%). The change in the relative volatility of components of the original mixture in the presence of a high(diethylene glycol) and a low-boiling (acetone) separating agent was investigated. Both solvents are selective agents used in extractive and re-extractive distillation processes. Three technological separation flowsheets containing two distillation columns were proposed.

Conclusions. The study established the operation parameters of the columns (number of theoretical stages, feed stages of the original mixture and separating agent, and reflux ratio) and energy consumption (total heat supplied to the columns boiler) of three separation flowsheets ensuring the production of products of a given quality (not less than 0.99 mol fractions). The flowsheet with diethylene glycol is characterized by the lowest energy consumption. It is recommended that complexes of extractive and re-extractive distillation be further optimized. This enables the second product of cumulus production—acetone—to be involved in the technological cycle.

1. Kharlampovich G.D., Churkin Yu.V. Fenoly (Phenols). Moscow: Khimiya; 1974. 376 p. (in Russ.).

2. Kruzhalov B.D., Golovanenko B.I. Sovmestnoe poluchenie fenola i atsetona (Joint Production of Phenol and Acetone). Moscow: Goskhimizdat; 1963 p. (in Russ.).

3. Timofeev V.S., Serafimov L.A, Timoshenko A.V. Printsipy tekhnologii osnovnogo organicheskogo i neftekhimicheskogo sinteza (Principles of basic organic and petrochemical synthesis technology). Moscow: Vysshaya shkola; 2010. 408 p. (in Russ.). ISBN 978-5-06-006067-6

4. Zakoshanskii V.M. Fenol i atseton: Analiz tekhnologii, kinetiki i mekhanizma osnovnykh reaktsii (Phenol and acetone: Analysis of Technologies, Kinetics and Mechanism of the Main Reactions). St. Petersburg: Khimizdat; 2009. 608 p. (in Russ.). ISBN 978-5-93808-168-0

5. Zakoshansky V.M. The cumene process for phenol- acetone production. Pet. Chem. 2007;47(4):273-284307. https://doi.org/10.1134/S096554410704007X [Original Russian Text: Zakoshanskii V.M. The cumene process for phenol-acetone production. Neftekhimiya. 2007;47(4):301-313 (in Russ.).]

6. Weber M., Weber M., Shnurr O. Method of producing phenol: RF Pat. RU2430082C2. Publ. 09.27.2011 (in Russ.).

7. Vasil’eva I.I., Tyvina T.N., Dmitrieva I.V. Purification of phenol from hydroxyacetone and 2-methylbenzofuran by rectification. Ros. Khim. Zh. 2008;52(4):117-124 (in Russ.).

8. Zakoshanskii V.M. Problems of separation and purification of products in the industrial production of phenol. Ros. Khim. Zh. 2008;52(4):103-111 (in Russ.).

9. Vasil’eva I.I., Tyvina T.N. Dmitrieva I.V. Method for purification of phenol from hydroxyacetone: RF Pat. RU2323202C1. Publ. 04.27.2008 (in Russ.).

10. Vasil’eva I.I., Zakoshanskii V.M., Koshelev Yu.N., Chulkov V.P. Pathways of Acetol Formation in the Course of Production of Phenol and Acetone by Cleavage of Cumyl Hydroperoxide. Russ. J. Appl. Chem. 2001;74(1):111-113. https://doi.org/10.1023/A:1012712420588 [Original Russian Text: Vasil’eva I.I., Zakoshanskii V.M., Koshelev Yu.N., Chulkov V.P. Pathways of Acetol Formation in the Course of Production of Phenol and Acetone by Cleavage of Cumyl Hydroperoxide. Zhurnal prikladnoi khimii. 2001;74(1):107-110 (in Russ.).]

11. Koshelev Yu.N., Zakoshanskii V.M., Vasil’eva I.I., Malov Yu.I. Method for treatment phenol from impurities: RF Pat. RU2266275C1. Publ. 20.12.2005 (in Russ.).

12. Serafimov L.A., Frolkova A.K. Fundamental principle of concentration-field redistribution between separation regions as a basis for the design of technological systems. Theor. Found. Chem. Eng. 1997;31(2):159-166. [Original Russian Text: Serafimov L.A., Frolkova A.K. Fundamental principle of concentration-field redistribution between separation regions as a basis for the design of technological systems. Teor. osnovy khim. tekhnologii. 1997;31(2):193-201 (in Russ.).]

13. Anokhina E.A. Energy saving in extractive distillation. Fine Chem. Technol. 2013;8(5):3-19 (in Russ.).

14. Frolkova A.K. Razdelenie azeotropnykh smesei. Fiziko-khimicheskie osnovy i tekhnologicheskie priemy (Separation of Azeotropic Mixtures. Physico-Chemical Basics and Technological Methods). Moscow: VLADOS; 2010. 192 p. (in Russ.).

15. Gaganov I.S. Optimization of phenol extraction technology by extractive distillation. In: Proceedings of The 30th Mendeleev Conference of Young Scientists. Moscow. 2020. P. 51. URL: http://www.chem.msu.su/rus/events/mendeleev-2020/theses.pdf

16. Gaganov I., Frolkova A., Frolkova A. Process for the recovery of phenol from a reaction mixture obtained by cumene method. In: Proceedings of The 47th International Conference of SSCHE - online conference. Bratislava, Slovakia: 2021.

17. Gaganov I.S., Fertikova V.G., Frolkova A.V., Frolkova A.K. Purification of phenol and chloroform from impurity components by extractive rectification. Khimicheskaya tekhnologiya. 2022;23(3):138-144 (in Russ.).