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Regeneration of levulinic acid from loaded-organic phase: equilibrium, kinetic studies and process economics

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Abstract

Regeneration of carboxylic acids from the loaded-organic phase is an essential step to complete the reactive extraction process. A study on the regeneration of levulinic acid from loaded-organic phase (methyl isobutyl ketone + tri-n-octylamine + acid) was carried out using various techniques including NaOH, temperature swing, diluent swing, and tri-methylamine methods. Equilibrium data obtained show that among all the methods, the recovery of acid is the highest for the tri-methylamine method when the molar ratio of tri-methylamine to levulinic acid concentrations is greater than 1. Kinetic studies performed for the tri-methylamine method showed that there are no changes in the specific rate of extraction with changes in stirrer speed rate and phase volume ratio (V aq/V org), and the overall order of reaction is 1.5. Based on the effects of stirrer speed and phase volume ratio on the specific rate of extraction, the reaction was concluded to occur in the fast regime. Also, about 80% of acid was recovered by the evaporation of tri-methylamine phase at 104–140 °C. A detailed economic evaluation for the recovery of levulinic acid using reactive extraction for a feed rate of 2 m3 h−1 shows that the payback period for recovering capital investment is 0.49 years.

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Abbreviations

\(C\) (m3):

Acid concentration

N (s−1):

Speed of agitation

h (m):

Height of the liquid in the reactor

r d (m):

Droplet radius

V d (m3):

Dispersed phase volume

S droplet (m2):

Droplet surface area

V droplet (m3):

Droplet volume

L (m):

Radius of reactor

\(R_{\text{A}}\) (kmol m−2 s−1):

Specific rate of extraction

n (–):

Number droplets formed during splitting

a (m−1):

Specific interfacial area

LAH (–):

Levulinic acid

K acid (–):

Acid dissociation constant

K TOA (–):

TOA dissociation constant

K TMA (–):

TMA dissociation constant

\(\% E\) (–):

Recovery efficiency

[TMA] (kmol m−3):

TMA concentration

ρ (kg m−3):

Density of liquid

Υ (N m−1):

Interfacial tension

Φ (–):

Dispersed phase volume ratio

Aq (–):

Aqueous

org (–):

Organic

in (–):

Initial

* (–):

Equilibrium

References

  • Keshav A, Wasewar KL (2010) Back extraction of propionic acid from loaded-organic phase. Chem Eng J 65:2751–2757. doi:10.1016/j.ces.2010.01.010

    Article  CAS  Google Scholar 

  • Baniel AM, Blumberg R, Hajdu K (1981) Recovery of acids from aqueous solutions. US Patent 4,275,234, June 23

  • Chaudhuri JB, Lyle D (1992) Emulsion liquid membrane extraction of organic acids. 1. A theoretical model for lactic acid extraction with emulsion swelling. Chem Eng Sci 47(1):41–48. doi:10.1016/0009-2509(92)80198-1

    Article  CAS  Google Scholar 

  • Doraiswamy LK, Sharma MM (1984) Heterogeneous reaction; Analysis, examples, and reactor design, vol. 2. Fluid–fluid–solid-reactions, 1st edn. Wiley, New York

  • Eyal AM, Bressler E (1993) Mini-review industrial separation of carboxylic acid and amino acids by liquid membranes: applicability, process considerations, and potential advantages. Biotechnol Bioeng 41:287–295 (ccc 0006-3592/93/030287-09)

    Article  CAS  Google Scholar 

  • Hanna GJ, Nobel RD (1985) Measurement of liquid–liquid interfacial kinetics. Chem Rev 85(6):583–598. doi:10.1021/cr00070a004

    Article  CAS  Google Scholar 

  • Hong YK, Hong WH, Hong TH (1999) Separation characteristics of lactic acid by using mixed tertiary amine extractants. Kor J Biotechnol Bioeng 14:566–571

    Google Scholar 

  • Streiwieser A Jr., Heathcock CH (1976) Introduction to organic chemistry. Macmillan, New York

    Google Scholar 

  • Kertes AS, King CJ (1986) Extraction chemistry of fermentation product carboxylic acids. Biotechnol Bioeng 28:269–282. doi:10.1002/bit.260280217

    Article  CAS  Google Scholar 

  • King CJ (1983) In: Lo TC, Baird MHI, Hanson C (eds) Handbook of solvent Extraction, Chap 18. Wiley-Interscience, New York, pp 567

  • Kuo Y, Munson CL, Rixey WG, Garcia AA, Frierman M (1987) Use of adsorbents for recovery of acetic acid from aqueous solutions I-factors governing capacity. Sep Purif Methods 16:31–64. doi:10.1080/03602548708058537

    Article  CAS  Google Scholar 

  • Mitchell JA, Reid EE (1931) The preparation of aliphatic amides. J Am Chem Soc 53:1879–1883

    Article  CAS  Google Scholar 

  • Poole LJ, King CJ (1991) Regeneration of carboxylic acid–amine extracts by back-extraction with an aqueous solution of a volatile amine. Ind Eng Chem Res 30:923–929 (0888-5885/91/2630-0923)

    Article  CAS  Google Scholar 

  • Ricker NL, Pittman EF, King CJ (1980) Solvent extraction with amines for recovery of acetic acid from diluent aqueous industrial stream. J Separ Proc Technol 1(2):23–30

    CAS  Google Scholar 

  • Shreve RN, Brink JA (1997) Chemical process industries, 4th edn. McGraw-Hill, New York

    Google Scholar 

  • Starks CM (1999) Interfacial area generation in two-phase systems and its effect on kinetics of phase transfer catalyzed reactions. Tetrahedron 55:6261–6274. doi:10.1016/S0040-4020(99)00203-3

    Article  CAS  Google Scholar 

  • Tamada JA, King CJ (1990) Extraction of carboxylic acids with amine extractants. 3. Effect of temperature, water co-extraction, and process considerations. Ind Eng Chem Res 29:1333–1338 (ISSN 0888-5885)

    Article  CAS  Google Scholar 

  • Turton R, Bailie RC, Whiting WB, Shaeiwitz JA (2009) Analysis, synthesis, and design of chemical processes, 3rd edn. Prentice Hall, USA

    Google Scholar 

  • Wardell JM, King CJ (1978) Solvent equilibria for extraction of carboxylic acids from water. J Chem Eng Data 23:144–148

    Article  CAS  Google Scholar 

  • Wasewar KL (2012) Reactive extraction: an intensifying approach for carboxylic acid separation. Int J Chem Eng Appl 3(4):249–255

    CAS  Google Scholar 

  • Wasewar KL, Heesink ABM, Versteeg GF, Pangarkar VG (2004a) Intensification of conversion of glucose to lactic acid: equilibria and kinetics for back extraction of lactic acid using trimethylamine. Chem Eng Sci 59:2315–2320

    Article  CAS  Google Scholar 

  • Wasewar KL, Yawalkar AA, Moulijn JA, Pangarkar VG (2004b) Fermentation of glucose to lactic acid coupled with reactive extraction: a review. Ind Eng Chem Res 43:5969–5982. doi:10.1021/ie049963n

    Article  CAS  Google Scholar 

  • Wennersten R (1978) Extraction of carboxylic acid from fermentation broth using solutions of tertiary amine. J Chem Eng Data 23:144–148

    Article  Google Scholar 

  • Yabannavar VM, Wang DIC (1991a) Analysis of mass transfer for immobilized cells in extractive lactic acid fermentation. Biotechnol Bioeng 37:544–550

    Article  CAS  Google Scholar 

  • Yabannavar VM, Wang DIC (1991b) Strategies for reducing solvent toxicity in extractive fermentations. Biotechnol Bioeng 37:716–722

    Article  CAS  Google Scholar 

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Correspondence to Rajarathinam Parthasarathy.

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Eda, S., Kota, B.J., Thella, P.K. et al. Regeneration of levulinic acid from loaded-organic phase: equilibrium, kinetic studies and process economics. Chem. Pap. 71, 1939–1951 (2017). https://doi.org/10.1007/s11696-017-0188-6

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  • DOI: https://doi.org/10.1007/s11696-017-0188-6

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