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14-07-2021 | Original Article

Separation of butyric acid from aqueous media using menthol-based hydrophobic deep eutectic solvent and modeling by response surface methodology

Author: Melisa Lalikoglu

Published in: Biomass Conversion and Biorefinery | Issue 4/2022

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Abstract

In the last decade, research on deep eutectic solvents used in many fields with different roles in chemistry has attracted great interest. Literature reviewing shows that one of these solvents’ most common usage areas is extraction applications as green extraction media, especially to recover biomass conversion products. In this work, hydrophobic deep eutectic solvents (HDES) with different hydrogen bond donors (HBD) and hydrogen bond acceptor (HBA) were mixed and used as a solvent to separate butyric acid from aqueous solutions. Menthol (M)-based HDESs were prepared using three long-chain carboxylic acids (nonanoic acid (NA), decanoic acid (DA), and dodecanoic acid (DDA)) and trioctylphosphine oxide (TOPO) in different molar ratios of binary combinations. Density and refractive index values of HDES were determined. To assess the obtained results, extraction efficiency (E%) and distribution coefficient (D) values were calculated. It was observed that HDES containing menthol and TOPO were extracted more than 90% of butyric acid from the water phase. The transition of butyric acid from the aqueous to the organic phase was demonstrated by FTIR analysis. The Box-Behnken method based on response surface methodology (RSM) was used to explore the impacts of the experimental conditions on reactive extraction yield and to obtain a model equation for the separation of butyric acid from its aqueous solution using M:TOPO hydrophobic deep eutectic solvent.

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Jiang L, Fu H, Yang HK et al (2018) Butyric acid: applications and recent advances in its bioproduction. Biotechnol Adv 36:2101–2117. https://doi.org/10.1016/j.biotechadv.2018.09.005CrossRef

Çağlar A, Tomar O, Ekiz T (2017) Butyric acid: structure, properties and effects on health. Kocatepe Vet J Kocatepe Vet J 10:213–225. https://doi.org/10.5578/kvj.59688CrossRef

Mascal M (2012) Chemicals from biobutanol: technologies and markets. Biofuels, Bioprod Biorefining 6:483–493. https://doi.org/10.1002/bbb.1328CrossRef

Zigová J, Šturdík E (2000) Advances in biotechnological production of butyric acid. J Ind Microbiol Biotechnol 24:153–160. https://doi.org/10.1038/sj.jim.2900795CrossRef

Xiao Z, Cheng C, Bao T et al (2018) Production of butyric acid from acid hydrolysate of corn husk in fermentation by Clostridium tyrobutyricum: Kinetics and process economic analysis. Biotechnol Biofuels 11:164. https://doi.org/10.1186/s13068-018-1165-1CrossRef

Atasoy M, Cetecioglu Z (2020) Butyric acid dominant volatile fatty acids production: bio-augmentation of mixed culture fermentation by Clostridium butyricum. J Environ Chem Eng 8:104496. https://doi.org/10.1016/j.jece.2020.104496CrossRef

Dwidar M, Park JY, Mitchell RJ, Sang BI (2012) The future of butyric acid in industry. Sci World J 2012:9 pages. https://doi.org/10.1100/2012/471417

Luo H, Yang R, Zhao Y et al (2018) Recent advances and strategies in process and strain engineering for the production of butyric acid by microbial fermentation. Bioresour Technol 253:343–354CrossRef

Câmara-Salim I, González-García S, Feijoo G, Moreira MT (2021) Screening the environmental sustainability of microbial production of butyric acid produced from lignocellulosic waste streams. Ind Crops Prod 162:113280. https://doi.org/10.1016/j.indcrop.2021.113280CrossRef

10.

Luo L, Li L, Wang H, Chen Y (2016) Tie-line data for aqueous mixtures of butyric acid with diisopropyl ether at various temperatures. J Chem Eng Data 61:760–765. https://doi.org/10.1021/acs.jced.5b00527CrossRef

11.

Ghanadzadeh H, Ghanadzadeh A, Asgharzadeh S, Moghadam M (2012) Measurement and correlation of phase equilibrium data of the mixtures consisting of butyric acid, water, cyclohexanone at different temperatures. J Chem Thermodyn 47:288–294. https://doi.org/10.1016/j.jct.2011.11.001CrossRef

12.

Chen Y, Wang Y, Zhou S et al (2017) Liquid phase equilibrium of the ternary systems, water + propionic or butyric acid + mesityl oxide, at (298.2 and 323.2) K. J Chem Thermodyn 111:72–79. https://doi.org/10.1016/j.jct.2017.03.018CrossRef

13.

Gündogdu T, Çehreli S (2012) Ternary liquid-liquid phase equilibria of (water-carboxylic acid-1-undecanol) systems at 298.15K. Fluid Phase Equilib 331:26–32. https://doi.org/10.1016/j.fluid.2012.06.020CrossRef

14.

Bilgin M, Arisoy Ç, Kirbaşlar ŞI (2009) Extraction equilibria of propionic and butyric acids with tri-n-octylphosphine oxide/diluent systems. J Chem Eng Data 54:3008–3013. https://doi.org/10.1021/je900063pCrossRef

15.

Mkhize NT, Msagati TAM, Mamba BB, Momba M (2014) Determination of volatile fatty acids in wastewater by solvent extraction and gas chromatography. Phys Chem Earth 67–69:86–92. https://doi.org/10.1016/j.pce.2013.10.008CrossRef

16.

Bayazit K, Uslu H, Gök A et al (2016) Investigation of ternary phase diagrams of (water + butyric acid + phenyl acetate) at different temperatures. J Chem Eng Data 61:1313–1320. https://doi.org/10.1021/acs.jced.5b00950CrossRef

17.

Yu C, Wu S, Zhao Y et al (2017) Liquid-liquid equilibrium data of water + butyric acid + butanal or n-butanol ternary systems at 293.15, 308.15, and 323.15 K. J Chem Eng Data 62:2244–2252. https://doi.org/10.1021/acs.jced.6b00941CrossRef

18.

Kirbaşlar ŞI (2006) Liquid - liquid equilibria of the water + butyric acid + decanol ternary system. Brazilian J Chem Eng 23:365–374. https://doi.org/10.1590/S0104-66322006000300010CrossRef

19.

Gök A, Kirbaşlar ŞI, Uslu H, Gilani HG (2011) Liquid-liquid equilibria of (water+butyric acid+diethyl succinate or diethyl glutarate or diethyl adipate) ternary systems. Fluid Phase Equilib 303:71–75. https://doi.org/10.1016/j.fluid.2011.01.012CrossRef

20.

Luo L, Liu D, Li L, Chen Y (2015) Phase equilibria of (water+propionic acid or butyric acid+2-methoxy-2-methylpropane) ternary systems at 298.2K and 323.2K. Fluid Phase Equilib 403:30–35. https://doi.org/10.1016/j.fluid.2015.06.003CrossRef

21.

Bilgin M (2006) Phase equilibria of liquid (water + butyric acid + oleyl alcohol) ternary system. J Chem Thermodyn 38:1634–1639. https://doi.org/10.1016/j.jct.2006.03.017CrossRef

22.

Inyang V, Lokhat D (2021) Butyric acid reactive extraction using trioctylamine in 1-decanol: response surface methodology parametric optimization technique. Arab J Sci Eng. https://doi.org/10.1007/s13369-020-05255-2CrossRef

23.

Senol A, Lalikoglu M, Bilgin M (2015) Modeling extraction equilibria of butyric acid distributed between water and tri-n-butyl amine/diluent or tri-n-butyl phosphate/diluent system: extension of the LSER approach. Fluid Phase Equilib 385https://doi.org/10.1016/j.fluid.2014.10.043

24.

Lalikoglu M, Bilgin M (2014) Ternary phase diagrams for aqueous mixtures of butyric acid with several solvents: experimental and correlated data. Fluid Phase Equilib 371:50–56. https://doi.org/10.1016/j.fluid.2014.03.008CrossRef

25.

Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2083. https://doi.org/10.1021/cr980032tCrossRef

26.

Singh SK, Savoy AW (2020) Ionic liquids synthesis and applications: An overview. J Mol Liq 297:112038CrossRef

27.

Han X, Armstrong DW (2007) Ionic liquids in separations. Acc Chem Res 40:1079–1086. https://doi.org/10.1021/ar700044yCrossRef

28.

Marták J, Schlosser Š (2017) Density, viscosity, and structure of equilibrium solvent phases in butyric acid extraction by phosphonium ionic liquid. J Chem Eng Data 62:3025–3035. https://doi.org/10.1021/acs.jced.7b00039CrossRef

29.

Marták J, Schlosser Š (2016) New mechanism and model of butyric acid extraction by phosphonium ionic liquid. J Chem Eng Data 61:2979–2996. https://doi.org/10.1021/acs.jced.5b01082CrossRef

30.

Marták J, Liptaj T, Schlosser Š (2019) Extraction of butyric acid by phosphonium decanoate ionic liquid. J Chem Eng Data 64:2973–2984. https://doi.org/10.1021/acs.jced.9b00057CrossRef

31.

Romero A, Santos A, Tojo J, Rodríguez A (2008) Toxicity and biodegradability of imidazolium ionic liquids. J Hazard Mater 151:268–273. https://doi.org/10.1016/j.jhazmat.2007.10.079CrossRef

32.

Anastas PT, Warner JC (1998) Green Chemistry: Theory and Practice. Green Chem Theory Pract Oxford Univ Press, New York

33.

Abbott AP, Capper G, Davies DL, et al (2003) Novel solvent properties of choline chloride/urea mixtures. Chem Commun 70–71. https://doi.org/10.1039/b210714g

34.

Abbott AP, Boothby D, Capper G et al (2004) Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J Am Chem Soc 126:9142–9147. https://doi.org/10.1021/ja048266jCrossRef

35.

Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082CrossRef

36.

Kollau LJBM, Vis M, Van Den Bruinhorst A et al (2018) Quantification of the liquid window of deep eutectic solvents. Chem Commun 54:13351–13354. https://doi.org/10.1039/c8cc05815fCrossRef

37.

Martins MAR, Pinho SP, Coutinho JAP (2019) Insights into the nature of eutectic and deep eutectic mixtures. J Solution Chem 48:962–982. https://doi.org/10.1007/s10953-018-0793-1CrossRef

38.

Schaeffer N, Abranches DO, Silva LP et al (2021) Non-ideality in thymol + menthol type V deep eutectic solvents. ACS Sustain Chem Eng 9:2203–2211. https://doi.org/10.1021/acssuschemeng.0c07874CrossRef

39.

Abranches DO, Martins MAR, Silva LP et al (2019) Phenolic hydrogen bond donors in the formation of non-ionic deep eutectic solvents: the quest for type v des. Chem Commun 55:10253–10256. https://doi.org/10.1039/c9cc04846dCrossRef

40.

Van Osch DJGP, Zubeir LF, Van Den Bruinhorst A et al (2015) Hydrophobic deep eutectic solvents as water-immiscible extractants. Green Chem 17:4518–4521. https://doi.org/10.1039/c5gc01451dCrossRef

41.

Ribeiro BD, Florindo C, Iff LC et al (2015) Menthol-based eutectic mixtures: hydrophobic low viscosity solvents. ACS Sustain Chem Eng 3:2469–2477. https://doi.org/10.1021/acssuschemeng.5b00532CrossRef

42.

Van Osch DJGP, Dietz CHJT, Warrag SEE, Kroon MC (2020) The curious case of hydrophobic deep eutectic solvents: a story on the discovery, design, and applications. ACS Sustain Chem Eng 8:10591–10612. https://doi.org/10.1021/acssuschemeng.0c00559CrossRef

43.

Florindo C, Branco LC, Marrucho IM (2017) Development of hydrophobic deep eutectic solvents for extraction of pesticides from aqueous environments. Fluid Phase Equilib 448:135–142. https://doi.org/10.1016/j.fluid.2017.04.002CrossRef

44.

Riveiro E, González B, Domínguez Á (2020) Extraction of adipic, levulinic and succinic acids from water using TOPO-based deep eutectic solvents. Sep Purif Technol 241:116692. https://doi.org/10.1016/j.seppur.2020.116692CrossRef

45.

Tang W, Dai Y, Row KH (2018) Evaluation of fatty acid/alcohol-based hydrophobic deep eutectic solvents as media for extracting antibiotics from environmental water. Anal Bioanal Chem 410:7325–7336. https://doi.org/10.1007/s00216-018-1346-6CrossRef

46.

Rodríguez-Llorente D, Bengoa A, Pascual-Muñoz G et al (2019) Sustainable recovery of volatile fatty acids from aqueous solutions using terpenoids and eutectic solvents. ACS Sustain Chem Eng 7:16786–16794. https://doi.org/10.1021/acssuschemeng.9b04290CrossRef

47.

van den Bruinhorst A, Raes S, Maesara SA et al (2019) Hydrophobic eutectic mixtures as volatile fatty acid extractants. Sep Purif Technol 216:147–157. https://doi.org/10.1016/j.seppur.2018.12.087CrossRef

48.

Verma R, Naik PK, Diaz I, Banerjee T (2021) Separation of low molecular weight alcohols from water with deep eutectic solvents: liquid-liquid equilibria and process simulations. Fluid Phase Equilib 533:112949. https://doi.org/10.1016/j.fluid.2021.112949CrossRef

49.

Van Osch DJGP, Parmentier D, Dietz CHJT et al (2016) Removal of alkali and transition metal ions from water with hydrophobic deep eutectic solvents. Chem Commun 52:11987–11990. https://doi.org/10.1039/c6cc06105bCrossRef

50.

Schaeffer N, Martins MAR, Neves CMSS et al (2018) Sustainable hydrophobic terpene-based eutectic solvents for the extraction and separation of metals. Chem Commun 54:8104–8107. https://doi.org/10.1039/c8cc04152kCrossRef

51.

Gilmore M, McCourt ÉN, Connolly F et al (2018) Hydrophobic deep eutectic solvents incorporating trioctylphosphine oxide: advanced liquid extractants. ACS Sustain Chem Eng 6:17323–17332. https://doi.org/10.1021/acssuschemeng.8b04843CrossRef

52.

Van Osch DJGP, Dietz CHJT, Van Spronsen J et al (2019) A search for natural hydrophobic deep eutectic solvents based on natural components. ACS Sustain Chem Eng 7:2933–2942. https://doi.org/10.1021/acssuschemeng.8b03520CrossRef

53.

Dietz CHJT, Erve A, Kroon MC et al (2019) Thermodynamic properties of hydrophobic deep eutectic solvents and solubility of water and HMF in them: Measurements and PC-SAFT modeling. Fluid Phase Equilib 489:75–82. https://doi.org/10.1016/j.fluid.2019.02.010CrossRef

54.

Rocha MAA, Raeissi S, Hage P et al (2017) Recovery of volatile fatty acids from water using medium-chain fatty acids and a cosolvent. Chem Eng Sci 165:74–80. https://doi.org/10.1016/j.ces.2017.02.014CrossRef

55.

Alkaya E, Kaptan S, Ozkan L et al (2009) Recovery of acids from anaerobic acidification broth by liquid-liquid extraction. Chemosphere 77:1137–1142. https://doi.org/10.1016/j.chemosphere.2009.08.027CrossRef

56.

Aşçı YS, Lalikoglu M (2021) Development of new hydrophobic deep eutectic solvents based on trioctylphosphine oxide for reactive extraction of carboxylic acids. Ind Eng Chem Res 60:1356–1365. https://doi.org/10.1021/acs.iecr.0c04551CrossRef

57.

Florindo C, Branco LC, Marrucho IM (2019) Quest for green-solvent design: from hydrophilic to hydrophobic (deep) eutectic solvents. Chemsuschem 12:1549–1559. https://doi.org/10.1002/cssc.201900147CrossRef

58.

Aşçi YS, Inci I (2010) Extraction equilibria of succinic acid from aqueous solutions by Amberlite LA-2 in various diluents. J Chem Eng Data 55:847–851. https://doi.org/10.1021/je9004917CrossRef

59.

Tuyun AF, Uslu H (2012) Extraction of D -(−)-quinic acid using an amine extractant in different diluents. J Chem Eng Data 57:190–194. https://doi.org/10.1021/je2009939CrossRef

60.

Chemarin F, Moussa M, Allais F et al (2017) Mechanistic modeling and equilibrium prediction of the reactive extraction of organic acids with amines: a comparative study of two complexation-solvation models using 3-hydroxypropionic acid. Sep Purif Technol 189:475–487. https://doi.org/10.1016/j.seppur.2017.07.083CrossRef

61.

Gök A (2020) Enhanced adsorption of nicotinic acid by different types of Mg/Al layered double hydroxides: synthesis, equilibrium, kinetics, and thermodynamics. J Dispers Sci Technol 41:779–786. https://doi.org/10.1080/01932691.2020.1729795CrossRef

62.

Ferreira SLC, Bruns RE, Ferreira HS et al (2007) Box-Behnken design: An alternative for the optimization of analytical methods. Anal Chim Acta 597:179–186. https://doi.org/10.1016/j.aca.2007.07.011CrossRef

63.

Box GEP, Behnken DW (1960) Some new three level designs for the study of quantitative variables. Technometrics 2. https://doi.org/10.1080/00401706.1960.10489912

64.

Doldolova K, Bener M, Lalikoğlu M, et al (2021) Optimization and modeling of microwave-assisted extraction of curcumin and antioxidant compounds from turmeric by using natural deep eutectic solvents. Food Chem 353https://doi.org/10.1016/j.foodchem.2021.129337

65.

Evlik T, Aşçı YS, Baylan N, et al (2020) Reactive separation of malic acid from aqueous solutions and modeling by artificial neural network (ANN) and response surface methodology (RSM). J Dispers Sci Technol 1–10https://doi.org/10.1080/01932691.2020.1838920

66.

Alhadid A, Mokrushina L, Minceva M (2020) Formation of glassy phases and polymorphism in deep eutectic solvents. J Mol Liq 314https://doi.org/10.1016/j.molliq.2020.113667

67.

Lemaoui T, Darwish AS, Attoui A et al (2020) Predicting the density and viscosity of hydrophobic eutectic solvents: towards the development of sustainable solvents. Green Chem 22:8511–8530. https://doi.org/10.1039/d0gc03077eCrossRef

68.

Byrne EL, O’donnell R, Gilmore M, et al (2020) Hydrophobic functional liquids based on trioctylphosphine oxide (TOPO) and carboxylic acids. Phys Chem Chem Phys 22:24744–24763. https://doi.org/10.1039/d0cp02605kCrossRef

69.

Socrates G (2004) Infrared and Raman characteristic group frequencies. Tables and charts, 3rd edn. Wiley, Chicester

70.

Baylan N, Çehreli S (2018) Ionic liquids as bulk liquid membranes on levulinic acid removal: a design study. J Mol Liq 266:299–308. https://doi.org/10.1016/j.molliq.2018.06.075CrossRef

71.

Gök A (2019) Experimental design of reactive extraction of levulinic acid using green solvents. J Nat Appl Sci 23:878–884. https://doi.org/10.19113/sdufenbed.524747CrossRef

Title: Separation of butyric acid from aqueous media using menthol-based hydrophobic deep eutectic solvent and modeling by response surface methodology
Author: Melisa Lalikoglu
Publication date: 14-07-2021
Publisher: Springer Berlin Heidelberg
Published in: Biomass Conversion and Biorefinery / Issue 4/2022
Print ISSN: 2190-6815
Electronic ISSN: 2190-6823
DOI: https://doi.org/10.1007/s13399-021-01711-7

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