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Separation of water – formic acid – acetic acid mixtures in the presence of sulfolane

https://doi.org/10.32362/2410-6593-2019-14-4-24-32

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Abstract

In this paper, extractive distillation flowsheets for water–formic acid–acetic acid mixtures were designed. Flowsheets not involving preliminary dehydration were considered, and the relative volatilities of the components in the presence of sulfolane were analyzed. The result of extractive distillation depends on the amount of sulfolane. The structure of the flowsheet is determined by the results of the basic ternary mixture extractive distillation. In three-column flowsheets (schemes I, II), water is isolated in the distillate of the extractive distillation column. In the second column, distillation of the formic acid–acetic acid–sulfolane mixture is carried out, yielding formic acid (90 wt %) and acetic acid (80 wt %). The recycled flow is returned to the first column. Dilution of the formic acid–acetic acid–sulfolane mixture with sulfolane (second column of flowsheet II) allows for acids of higher quality (main substance content equal to or more than 98.5 wt %) to be obtained. Flowsheet III includes four columns and two recycling stages. First, the water–formic acid mixture is isolated in the distillate of the extractive distillation column. Then, water and formic acid are separated in a two-column complex by extractive distillation, also with sulfolane. We were carrying out calculations for column working pressure 101.32 and 13.33 kPa. To prevent thermal decomposition of sulfolane, working pressure for regeneration columns was always 13.33 kPa. The extractive distillation column of the basic three-component mixture is the main factor contributing to the total energy consumption for separation (in all schemes).

About the Authors

V. M. Raeva
MIREA – Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation

Cand. of Sci. (Engineering), Associate Professor of the Chair of Chemistry and Technology of Basic Organic Synthesis

86, Vernadskogo pr., Moscow, 119571, Russia

Scopus Author ID 6602836975

ResearcherID C-8812-2014



O. V. Gromova
MIREA – Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation

Master, Chair of Chemistry and Technology of Basic Organic Synthesis

86, Vernadskogo pr., Moscow, 119571, Russia



References

1. Gayle A.A., Somov V.Ye., Varshavskiy O.M., Semenov L.V. Sulfolan: Properties and use as a selective solvent. Saint-Petersburg: Khimizdat Publ., 1998. 144 p. (in Russ.).

2. Painer D., Lux S., Grafschafter A., Toth A., Siebenhofen M. Isolation of carboxylic acids from biobased feedstock. Chem. Ing. Tech. 2017;89(1-2):161-171. https://doi.org/10.1002/cite.201600090

3. Kushner T.M., Tatsiyevskaya G.I., Serafimov L.A., Lʼvov S.V. Isolation of lower carboxylic acids from the fraction of straight-run gasoline oxide. Khimicheskaya promyshlennostʼ= Chemical Industry. 1969;1:20-23 (in Russ.).

4. Patil K.D., Kulkarni B.D. Review of recovery methods for acetic acid from industrial waste streams by reactive distillation. J. Water Pollut. Purif. Res. 2014;1(2):13-18. https://www.researchgate.net/publication/263327618

5. Frolov G.M., Shaburov M.A. Acetic acid production. Moscow: Lesnaya promyshlennostʼ Publ., 1978. 240 p. (inRuss.).

6. Berg L. Dehydration of acetic acid by extractive distillation; pat. 5,167,774 US; filed 02/06/1992; publ. 12/01/1992.

7. Saha B., Chopade S., Mahajan S. Recovery of dilute acetic acid through esterification in a reactive distillation column. Catal. Today. 2000;60(1):147-157. http://dx.doi.org/10.1016/S0920-5861(00)00326-6

8. Muurinen E.I., Solo J.K. Solvent recovery in peroxyacid pulping. In: Proceed. of the First European Congress on Chemical Engineering. Florence, Italy. May 4-7, 1997; 1:543-552.

9. Raeva V.M. Features of the behavior of azeotropic mixtures and their separation with varying pressure: thesis ... Cand. of Sci. (Engineering). Moscow, 1998. 168 p. (in Russ.).

10. Painer D., Lux S., Siebenhofen M. Recovery of formic acid and acetic acid from waste water using reactive distillation. Separation Science and Technology. 2015;50(18):2930-2936. https://doi.org/10.1080/01496395.2015.1085407

11. Raeva V.M., Frolkova A.K. Separation of azeotropic mixtures using pressure-based complexes. Russian Journal of General Chemistry. 1998;XLII(6):76- 88 (in Russ.).

12. Painer D., Lux S., Grafschafter A., Toth A., Siebenhofen M. Isolation of carboxylic acids from biobased feedstock. Chem. Ing. Tech. 2017;89(1-2):161-171. https://doi.org/10.1002/cite.201600090

13. Berg L. Separation of formic acid from acetic acid by extractive distillation: pat. 4,692,219 US; filed 12/03/1986; publ. 09/08/1987.

14. Patil K.D., Kulkarni B.D. Review of recovery methods for acetic acid from industrial waste streams by reactive distillation. J. Water Pollut. Purif. Res. 2014;1(2):13-18. https://www.researchgate.net/publication/263327618

15. Bates R.G., Pawlak Z. Solvent effects on acid-base behavior: Five uncharged acids in water-sulfolane solvents. J. Solution Chem. 1976;5(3):213-222. https://doi.org/10.1007/BF00654338

16. Berg L. Separation of formic acid from acetic acid by extractive distillation with acetyl salicylic acid: pat. 4,909,907 US; filed 01/17/1989; publ. 03/20/1990.

17. Saha B., Chopade S., Mahajan S. Recovery of dilute acetic acid through esterification in a reactive distillation column. Catal. Today. 2000;60(1):147-157. http://dx.doi.org/10.1016/S0920-5861(00)00326-6

18. Cohen L.R. Method for separating carboxylic acids from mixtures with non-acids: pat. 4,576,683 US; filed 06/06/1984; publ. 03/18/1986.

19. Painer D., Lux S., Siebenhofen M. Recovery of formic acid and acetic acid from waste water using reactive distillation. Separation Science and Technology. 2015;50(18):2930-2936. https://doi.org/10.1080/01496395.2015.1085407

20. Muuriner E. A review and distillation study related to peroxyacid pulping. Organosolv pulping. Oulu, Finland: Publ. House Oulu Yliopisto, 2000. 314 p. http://herkules.oulu.fi/isbn9514256611/isbn9514256611.pdf)

21. Berg L. Separation of formic acid from acetic acid by extractive distillation: pat. 4,692,219 US; filed 12/03/1986; publ. 09/08/1987.

22. Sprakel L.M.J., Schuur B. Solvent developments for liquid-liquid extraction of carboxylic acids in perspective. Separation and Purification Technology. 2019; 211:935-957. https://doi.org/10.1016/j.seppur.2018.10.023

23. Berg L. Separation of formic acid from acetic acid by extractive distillation with acetyl salicylic acid: pat. 4,909,907 US; filed 01/17/1989; publ. 03/20/1990.

24. Behroozi M., Vahedpour M., Shardi Manaheji M. Separation of formic acid from aqueous solutions by liquid extraction technique at different temperatures. Phys. Chem. Res. 2019;7(1):201-215. https://dx.doi.org/10.22036/pcr.2019.154646.1557

25. Cohen L.R. Method for separating carboxylic acids from mixtures with non-acids: pat. 4,576,683 US; filed 06/06/1984; publ. 03/18/1986.

26. Berg L., Yeh An-I. Dehydration of formic acid by extractive distillation: pat. 4,642,166 US; filed 02/10/1986; publ. 02/10/1987.

27. Muuriner E. A review and distillation study related to peroxyacid pulping. Organosolv pulping. Oulu, Finland: Publ. House Oulu Yliopisto, 2000. 314 p. http://herkules.oulu.fi/isbn9514256611/isbn9514256611.pdf)

28. Berg L., Kraig M., Szabados R. J. Dehydration of formic acid by extractive distillation: pat. 5,173,156 US; filed 12/09/1991; publ. 12/22/1992.

29. Sprakel L.M.J., Schuur B. Solvent developments for liquid-liquid extraction of carboxylic acids in perspective. Separation and Purification Technology. 2019; 211:935-957. https://doi.org/10.1016/j.seppur.2018.10.023

30. Berg L. Dehydration of formic acid by extractive distillation: pat. 4,786,370 US; filed 01/04/1988; publ. 11/22/1988.

31. Behroozi M., Vahedpour M., Shardi Manaheji M. Separation of formic acid from aqueous solutions by liquid extraction technique at different temperatures. Phys. Chem. Res. 2019;7(1):201-215. https://dx.doi.org/10.22036/pcr.2019.154646.1557

32. Berg L. Dehydration of formic acid by extractive distillation with dicarboxylic acids; pat. 4,877,490 US; filed 01/23/1989; publ. 10/31/1989.

33. Berg L., Yeh An-I. Dehydration of formic acid by extractive distillation: pat. 4,642,166 US; filed 02/10/1986; publ. 02/10/1987.

34. Berg L., Yeh An-I. Dehydratation of impure formic acid by extractive distillation; pat. 4,735,690 US; filed 04/28/1986; publ. 04/05/1988.

35. Berg L., Kraig M., Szabados R. J. Dehydration of formic acid by extractive distillation: pat. 5,173,156 US; filed 12/09/1991; publ. 12/22/1992.

36. Buelow H., Hohenschutz H., Schmidt J.E., Sachsze W. Purification of formic acid by extractive distillation; pat. 4,076,594 US; filed 10/04/1976; publ. 02/28/1978.

37. Berg L. Dehydration of formic acid by extractive distillation: pat. 4,786,370 US; filed 01/04/1988; publ. 11/22/1988.

38. Prajapati Chintan, Bhatt R.P. Separation of azeotropic mixture of formic acid − water by using Li-Br as a salt by extractive distillation. IJARIIE. 2016;2(3):607-612 (available from http://www.ijariie.com).

39. Berg L. Dehydration of formic acid by extractive distillation with dicarboxylic acids; pat. 4,877,490 US; filed 01/23/1989; publ. 10/31/1989.

40. Berg L. Separation of formic acid from acetic acid by extractive distillation: pat. 54,692,219. US; filed 03/12/1986; publ. 08/09/1987.

41. Berg L., Yeh An-I. Dehydratation of impure formic acid by extractive distillation; pat. 4,735,690 US; filed 04/28/1986; publ. 04/05/1988.

42. Berg L. Separation of formic acid from acetic acid by extractive distillation; pat. 5,227,029 US; filed 01/29/1993; publ. 07/13/1993.

43. Buelow H., Hohenschutz H., Schmidt J.E., Sachsze W. Purification of formic acid by extractive distillation; pat. 4,076,594 US; filed 10/04/1976; publ. 02/28/1978.

44. Berg L. Separation of formic acid from acetic acid by extract separation of formic acid from acetic acid by extractive distillation; pat. 4,909,907 US; filed 01/17/1989; publ. 03/20/1990.

45. Prajapati Chintan, Bhatt R.P. Separation of azeotropic mixture of formic acid − water by using Li-Br as a salt by extractive distillation. IJARIIE. 2016;2(3):607-612 (available from http://www.ijariie.com).

46. Kirk-Othmer Encyclopedia of Chemical Technology. V. 8. Online ISBN: 9780471238966 Copyright © 1999-2014 by John Wiley and Sons, Inc.

47. Berg L. Separation of formic acid from acetic acid by extractive distillation: pat. 54,692,219. US; filed 03/12/1986; publ. 08/09/1987.

48. Gayle A.A., Somov V.Ye., Varshavskiy O.M., Semenov L.V. Sulfolan: Properties and use as a selective solvent. Saint-Petersburg: Khimizdat Publ., 1998. 144 p. (in Russ.).

49. Berg L. Separation of formic acid from acetic acid by extractive distillation; pat. 5,227,029 US; filed 01/29/1993; publ. 07/13/1993.

50. Berg L. Dehydration of acetic acid by extractive distillation; pat. 5,167,774 US; filed 02/06/1992; publ. 12/01/1992.

51. Berg L. Separation of formic acid from acetic acid by extract separation of formic acid from acetic acid by extractive distillation; pat. 4,909,907 US; filed 01/17/1989; publ. 03/20/1990.

52. Raeva V.M. Features of the behavior of azeotropic mixtures and their separation with varying pressure: thesis ... Cand. of Sci. (Engineering). Moscow, 1998. 168 p. (in Russ.).

53. Kirk-Othmer Encyclopedia of Chemical Technology. V. 8. Online ISBN: 9780471238966 Copyright © 1999-2014 by John Wiley and Sons, Inc.

54. Raeva V.M., Frolkova A.K. Separation of azeotropic mixtures using pressure-based complexes. Russian Journal of General Chemistry. 1998;XLII(6):76- 88 (in Russ.).

55. Gayle A.A., Somov V.Ye., Varshavskiy O.M., Semenov L.V. Sulfolan: Properties and use as a selective solvent. Saint-Petersburg: Khimizdat Publ., 1998. 144 p. (in Russ.).

56. Bates R.G., Pawlak Z. Solvent effects on acid-base behavior: Five uncharged acids in water-sulfolane solvents. J. Solution Chem. 1976;5(3):213-222. https://doi.org/10.1007/BF00654338

57. Berg L. Dehydration of acetic acid by extractive distillation; pat. 5,167,774 US; filed 02/06/1992; publ. 12/01/1992.

58. Raeva V.M. Features of the behavior of azeotropic mixtures and their separation with varying pressure: thesis ... Cand. of Sci. (Engineering). Moscow, 1998. 168 p. (in Russ.).

59. Raeva V.M., Frolkova A.K. Separation of azeotropic mixtures using pressure-based complexes. Russian Journal of General Chemistry. 1998;XLII(6):76- 88 (in Russ.).

60. Bates R.G., Pawlak Z. Solvent effects on acid-base behavior: Five uncharged acids in water-sulfolane solvents. J. Solution Chem. 1976;5(3):213-222. https://doi.org/10.1007/BF00654338


Supplementary files

1. Fig. 1. The diagram of the vapor−liquid equilibrium (VLE) for the water (W)−formic acid (FA)−acetic acid (AA) system. Black line – 13.33 kPa; grey line – 101.32 kPa
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Raeva V.M., Gromova O.V. Separation of water – formic acid – acetic acid mixtures in the presence of sulfolane. Fine Chemical Technologies. 2019;14(4):24-32. https://doi.org/10.32362/2410-6593-2019-14-4-24-32

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