Skip to main content

Advertisement

SpringerLink
Log in

Green Solvents for the Extraction of High Added-Value Compounds from Agri-food Waste

  • Published:
Food Engineering Reviews Aims and scope Submit manuscript

Abstract

Large amounts of agri-food by-products, non-edible food, and waste are produced throughout the supply chain from the initial production to the final consumption stages. The valorization of this biomass to obtain high value-added compounds has been the focus of extensive research in the last decade. For this purpose, the use of green techniques is essential to reduce the negative impact on the health and the environment. In this review, we discuss the use of green solvents for the valorization of agri-food waste and by-products, and we consider their potential to replace conventional organic solvents in order to provide more environmentally friendly and sustainable processes. The use of supercritical fluids, neoteric (ionic liquids and deep eutectic solvents), bio-based, and supramolecular solvents is critically dicussed. Parameters affecting extraction efficiency are detailed for each type of solvent along with advantages and limitations for application at the industrial scale.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Abdelmoez W, Nage SA, Bastawess A et al (2014) Subcritical water technology for wheat straw hydrolysis to produce value added products. J Clean Prod 70:68–77. https://doi.org/10.1016/j.jclepro.2014.02.011

    Article  CAS  Google Scholar 

  2. Alañón ME, Alarcón M, Marchante L et al (2017) Extraction of natural flavorings with antioxidant capacity from cooperage by-products by green extraction procedure with subcritical fluids. Ind Crop Prod 103:222–232. https://doi.org/10.1016/j.indcrop.2017.03.050

    Article  CAS  Google Scholar 

  3. Albarelli JQ, Santos DT, Ensinas AV et al (2018) Comparison of extraction techniques for product diversification in a supercritical water gasification-based sugarcane-wet microalgae biorefinery: thermoeconomic and environmental analysis. J Clean Prod 201:697–705. https://doi.org/10.1016/j.jclepro.2018.08.137

    Article  CAS  Google Scholar 

  4. Alonso DA, Baeza A, Chinchilla R et al (2016) Deep eutectic solvents: the organic reaction medium of the century. Eur J Org Chem 2016:612–632. https://doi.org/10.1002/ejoc.201501197

    Article  CAS  Google Scholar 

  5. Alvarez VH, Cahyadi J, Xu D et al (2014) Optimization of phytochemicals production from potato peel using subcritical water: experimental and dynamic modeling. J Supercrit Fluids 90:8–17. https://doi.org/10.1016/j.supflu.2014.02.013

    Article  CAS  Google Scholar 

  6. Alvarez MV, Cabred S, Ramirez CL, Fanovich MA (2019) Valorization of an agroindustrial soybean residue by supercritical fluid extraction of phytochemical compounds. J Supercrit Fluids 143:90–96. https://doi.org/10.1016/j.supflu.2018.07.012

    Article  CAS  Google Scholar 

  7. Apostolakis A, Grigorakis S, Makris DP (2014) Optimisation and comparative kinetics study of polyphenol extraction from olive leaves (Olea europaea) using heated water/glycerol mixtures. Sep Purif Technol 128:89–95. https://doi.org/10.1016/j.seppur.2014.03.010

    Article  CAS  Google Scholar 

  8. Araújo M, Pimentel FB, Alves RC, Oliveira MBPP (2015) Phenolic compounds from olive mill wastes: health effects, analytical approach and application as food antioxidants. Trends Food Sci Technol 45:200–211. https://doi.org/10.1016/j.tifs.2015.06.010

    Article  CAS  Google Scholar 

  9. Arun KB, Chandran J, Dhanya R et al (2015) A comparative evaluation of antioxidant and antidiabetic potential of peel from young and matured potato. Food Biosci 9:36–46. https://doi.org/10.1016/j.fbio.2014.10.003

    Article  CAS  Google Scholar 

  10. Ballesteros-Gómez A, Rubio S (2012) Environment-responsive alkanol-based supramolecular solvents: characterization and potential as restricted access property and mixed-mode extractants. Anal Chem 84:342–349. https://doi.org/10.1021/ac2026207

    Article  CAS  PubMed  Google Scholar 

  11. Ballesteros-Gómez A, Sicilia MD, Rubio S (2010) Supramolecular solvents in the extraction of organic compounds. A review. Anal Chim Acta 677:108–130. https://doi.org/10.1016/j.aca.2010.07.027

    Article  CAS  PubMed  Google Scholar 

  12. Ballesteros-Gómez A, Lunar L, Sicilia MD, Rubio S (2018) Hyphenating supramolecular solvents and liquid chromatography: tips for efficient extraction and reliable determination of organics. Chromatographia 82:1–14. https://doi.org/10.1007/s10337-018-3614-1

    Article  CAS  Google Scholar 

  13. Ben-Youssef S, Fakhfakh J, Breil C et al (2017) Green extraction procedures of lipids from Tunisian date palm seeds. Ind Crop Prod 108:520–525. https://doi.org/10.1016/j.indcrop.2017.07.010

    Article  CAS  Google Scholar 

  14. Bermejo DV, Luna P, Manic MS et al (2013) Extraction of caffeine from natural matter using a bio-renewable agrochemical solvent. Food Bioprod Process 91:303–309. https://doi.org/10.1016/j.fbp.2012.11.007

    Article  CAS  Google Scholar 

  15. Bosiljkov T, Dujmić F, Cvjetko Bubalo M et al (2017) Natural deep eutectic solvents and ultrasound-assisted extraction: green approaches for extraction of wine lees anthocyanins. Food Bioprod Process 102:195–203. https://doi.org/10.1016/j.fbp.2016.12.005

    Article  CAS  Google Scholar 

  16. Braga MEM, Santos RMS, Seabra IJ et al (2008) Fractioned SFE of antioxidants from maritime pine bark. J Supercrit Fluids 47:37–48. https://doi.org/10.1016/j.supflu.2008.05.005

    Article  CAS  Google Scholar 

  17. Byrne FP, Jin S, Paggiola G, Petchey THM, Clark JH, Farmer TJ, Hunt AJ, Robert McElroy C, Sherwood J (2016) Tools and techniques for solvent selection: green solvent selection guides. Sustain Chem Process 4:7–24. https://doi.org/10.1186/s40508-016-0051-z

    Article  CAS  Google Scholar 

  18. Caballo C, Sicilia MD, Rubio S (2017) Chapter 5 - supramolecular solvents for green chemistry. In: Pena-Pereira F, Tobiszewski M (eds) the application of green solvents in separation processes, 1st edn. Elsevier, pp 111–137

  19. Cabeza LF, de Gracia A, Fernández AI, Farid MM (2017) Supercritical CO2 as heat transfer fluid: a review. Appl Therm Eng 125:799–810. https://doi.org/10.1016/j.applthermaleng.2017.07.049

    Article  CAS  Google Scholar 

  20. Calvo-Flores FG, Monteagudo-Arrebola MJ, Dobado JA, Isac-García J (2018) Green and bio-based solvents. Top Curr Chem 376:18. https://doi.org/10.1007/s41061-018-0191-6

    Article  CAS  Google Scholar 

  21. Campone L, Celano R, Lisa Piccinelli A, Pagano I, Carabetta S, Sanzo RD, Russo M, Ibañez E, Cifuentes A, Rastrelli L (2018) Response surface methodology to optimize supercritical carbon dioxide/co-solvent extraction of brown onion skin by-product as source of nutraceutical compounds. Food Chem 269:495–502. https://doi.org/10.1016/j.foodchem.2018.07.042

    Article  CAS  PubMed  Google Scholar 

  22. Carciochi RA, D’Alessandro LG, Vauchel P, et al. (2017) Chapter 4 - valorization of agrifood by-products by extracting valuable bioactive compounds using green processes. In: Grumezescu AM, Holban AM (eds) Ingredients extraction by physicochemical methods in food. Academic Press, pp 191–228. https://doi.org/10.1016/B978-0-12-811521-3.00004-1

    Chapter  Google Scholar 

  23. Carmona-Cabello M, Garcia IL, Leiva-Candia D, Dorado MP (2018) Valorization of food waste based on its composition through the concept of biorefinery. Curr Opin Green Sustain Chem 14:67–79. https://doi.org/10.1016/j.cogsc.2018.06.011

    Article  Google Scholar 

  24. Castro-Vargas HI, Baumann W, Ferreira SRS, Parada-Alfonso F (2019) Valorization of papaya (Carica papaya L.) agroindustrial waste through the recovery of phenolic antioxidants by supercritical fluid extraction. J Food Sci Technol-Mysore 56:3055–3066. https://doi.org/10.1007/s13197-019-03795-6

    Article  CAS  Google Scholar 

  25. Chan W-C, Su M-Q (2008) Biofiltration of ethyl acetate and amyl acetate using a composite bead biofilter. Bioresour Technol 99:8016–8021. https://doi.org/10.1016/j.biortech.2008.03.045

    Article  CAS  PubMed  Google Scholar 

  26. Chanioti S, Tzia C (2018) Extraction of phenolic compounds from olive pomace by using natural deep eutectic solvents and innovative extraction techniques. Innovative Food Sci Emerg Technol 48:228–239. https://doi.org/10.1016/j.ifset.2018.07.001

    Article  CAS  Google Scholar 

  27. Chatzilazarou A, Katsoyannos E, Gortzi O, Lalas S, Paraskevopoulos Y, Dourtoglou E, Tsaknis J (2010) Removal of polyphenols from wine sludge using cloud point extraction. J Air Waste Manage Assoc 60:454–459. https://doi.org/10.3155/1047-3289.60.4.454

    Article  CAS  Google Scholar 

  28. Chemat S, Tomao V, Chemat F (2012) Limonene as green solvent for extraction of natural products. In: Mohammad A (ed) Green solvents I: properties and applications in chemistry. Springer Netherlands, Dordrecht, pp 175–186

    Chapter  Google Scholar 

  29. Clark JH, Tavener SJ (2007) Alternative solvents: shades of green. Org Process Res Dev 11:149–155. https://doi.org/10.1021/op060160g

    Article  CAS  Google Scholar 

  30. Cláudio AFM, Cognigni A, de Faria ELP, Silvestre AJD, Zirbs R, Freire MG, Bica K (2018) Valorization of olive tree leaves: extraction of oleanolic acid using aqueous solutions of surface-active ionic liquids. Sep Purif Technol 204:30–37. https://doi.org/10.1016/j.seppur.2018.04.042

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  31. Cooney MJ, Benjamin K (2016) Ionic Liquids in Lipid Extraction and Recovery. In: Xu X, Guo Z, Cheong L-Z (eds) Ionic Liquids in Lipid Processing and Analysis. AOCS Press, pp 279–316. https://doi.org/10.1016/B978-1-63067-047-4.00009-X

    Chapter  Google Scholar 

  32. Cui Q, Peng X, Yao X-H et al (2015) Deep eutectic solvent-based microwave-assisted extraction of genistin, genistein and apigenin from pigeon pea roots. Sep Purif Technol 150:63–72. https://doi.org/10.1016/j.seppur.2015.06.026

    Article  CAS  Google Scholar 

  33. Cunha SC, Fernandes JO (2018) Extraction techniques with deep eutectic solvents. TrAC Trends Anal Chem 105:225–239. https://doi.org/10.1016/j.trac.2018.05.001

    Article  CAS  Google Scholar 

  34. Cvjetko Bubalo M, Ćurko N, Tomašević M, Kovačević Ganić K, Radojčić Redovniković I (2016) Green extraction of grape skin phenolics by using deep eutectic solvents. Food Chem 200:159–166. https://doi.org/10.1016/j.foodchem.2016.01.040

    Article  CAS  PubMed  Google Scholar 

  35. Cvjetko Bubalo M, Vidović S, Radojčić Redovniković I, Jokić S (2018) New perspective in extraction of plant biologically active compounds by green solvents. Food Bioprod Process 109:52–73. https://doi.org/10.1016/j.fbp.2018.03.001

    Article  CAS  Google Scholar 

  36. da Silva RPFF, Rocha-Santos TAP, Duarte AC (2016) Supercritical fluid extraction of bioactive compounds. TrAC Trends Anal Chem 76:40–51. https://doi.org/10.1016/j.trac.2015.11.013

    Article  CAS  Google Scholar 

  37. Dai Y, van Spronsen J, Witkamp GJ, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68. https://doi.org/10.1016/j.aca.2012.12.019

    Article  CAS  PubMed  Google Scholar 

  38. Das S, Mondal A, Balasubramanian S (2017) Recent advances in modeling green solvents. Curr Opin Green Sustain Chem 5:37–43. https://doi.org/10.1016/j.cogsc.2017.03.006

    Article  Google Scholar 

  39. de Jesus SS, Ferreira GF, Fregolente LV, Maciel Filho R (2018) Laboratory extraction of microalgal lipids using sugarcane bagasse derived green solvents. Algal Res 35:292–300. https://doi.org/10.1016/j.algal.2018.09.001

    Article  Google Scholar 

  40. DeSimone JM (2002) Practical Approaches to Green Solvents. Science 297:799–803. https://doi.org/10.1126/science.1069622

    Article  CAS  PubMed  Google Scholar 

  41. Dias Ribeiro B, Weingart Barreto D, Zarur Coelho MA (2015) Use of micellar extraction and cloud point preconcentration for valorization of saponins from sisal (Agave sisalana) waste. Food Bioprod Process 94:601–609. https://doi.org/10.1016/j.fbp.2014.07.004

    Article  CAS  Google Scholar 

  42. Djas M, Henczka M (2018) Reactive extraction of carboxylic acids using organic solvents and supercritical fluids: a review. Sep Purif Technol 201:106–119. https://doi.org/10.1016/j.seppur.2018.02.010

    Article  CAS  Google Scholar 

  43. Dominguez de Maria P (2017) Ionic liquids, switchable solvents and eutectic mixtures. In: Green solvents. Elsevier, Amsterdam, p 533

    Google Scholar 

  44. El-Malah MH, Hassanein MM, Helmy Areif M, Al-Amrousi EF (2015) Utilization of Egyptian tomato waste as a potential source of natural antioxidants using solvents, microwave and ultrasound extraction methods. Am J Food Technol 10:14–25. https://doi.org/10.3923/ajft.2015.14.25

    Article  CAS  Google Scholar 

  45. Galanakis CM (2015) Food waste recovery. processing technologies and industrial techniques. Elsevier

  46. Gorbaty Y, Bondarenko GV (2017) Transition of liquid water to the supercritical state. J Mol Liq 239:5–9. https://doi.org/10.1016/j.molliq.2016.06.040

    Article  CAS  Google Scholar 

  47. Grewal J, Khare SK (2018) One-pot bioprocess for lactic acid production from lignocellulosic agro-wastes by using ionic liquid stable Lactobacillus brevis. Bioresour Technol 251:268–273. https://doi.org/10.1016/j.biortech.2017.12.056

    Article  CAS  PubMed  Google Scholar 

  48. Grigoras CG, Destandau E, Fougère L, Elfakir C (2013) Evaluation of apple pomace extracts as a source of bioactive compounds. Ind Crop Prod 49:794–804. https://doi.org/10.1016/j.indcrop.2013.06.026

    Article  CAS  Google Scholar 

  49. Gustavsson J, Cederberg C, Sonesson U et al (2011) Global food losses and food waste. Food and Agriculture Organization of the United Nations, Rome

    Google Scholar 

  50. Gutiérrez-Arnillas E, Álvarez MS, Deive FJ et al (2016) New horizons in the enzymatic production of biodiesel using neoteric solvents. Renew Energy 98:92–100. https://doi.org/10.1016/j.renene.2016.02.058

    Article  CAS  Google Scholar 

  51. Hadi NA, Ng MH, Choo YM et al (2015) Performance of choline-based deep eutectic solvents in the extraction of tocols from crude palm oil. J Am Oil Chem Soc 92:1709–1716. https://doi.org/10.1007/s11746-015-2720-6

    Article  CAS  Google Scholar 

  52. Henderson RK, Jiménez-González C, Constable DJC et al (2011) Expanding GSK’s solvent selection guide – embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem 13:854–862. https://doi.org/10.1039/C0GC00918K

    Article  CAS  Google Scholar 

  53. Herrero M, Cifuentes A, Ibañez E (2006) Sub- and supercritical fluid extraction of functional ingredients from different natural sources: plants, food-by-products, algae and microalgae: a review. Food Chem 98:136–148. https://doi.org/10.1016/j.foodchem.2005.05.058

    Article  CAS  Google Scholar 

  54. Hou Q, Li W, Ju M, Liu L, Chen Y, Yang Q, Wang J (2015) Separation of polysaccharides from rice husk and wheat bran using solvent system consisting of BMIMOAc and DMI. Carbohydr Polym 133:517–523. https://doi.org/10.1016/j.carbpol.2015.07.059

    Article  CAS  PubMed  Google Scholar 

  55. Hou X-D, Lin K-P, Li A-L et al (2018) Effect of constituents molar ratios of deep eutectic solvents on rice straw fractionation efficiency and the micro-mechanism investigation. Ind Crop Prod 120:322–329. https://doi.org/10.1016/j.indcrop.2018.04.076

    Article  CAS  Google Scholar 

  56. Hu XM, Zhang BX, Dong SJ et al (2014) Hydrolisis of soybean by-products to prepare reducing sugar in ionic liquids. Asian J Chem 26:8475–8478

    Article  Google Scholar 

  57. Huang Y, Feng F, Jiang J, Qiao Y, Wu T, Voglmeir J, Chen ZG (2017) Green and efficient extraction of rutin from tartary buckwheat hull by using natural deep eutectic solvents. Food Chem 221:1400–1405. https://doi.org/10.1016/j.foodchem.2016.11.013

    Article  CAS  PubMed  Google Scholar 

  58. Huang H, Belwal T, Jiang L et al (2019) Valorization of lotus byproduct (Receptaculum Nelumbinis) under green extraction condition. Food Bioprod Process 115:110–117. https://doi.org/10.1016/j.fbp.2019.03.006

    Article  CAS  Google Scholar 

  59. Huddleston JG, Willauer HD, Swatloski RP et al (1998) Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction. Chem Commun:1765–1766. https://doi.org/10.1039/A803999B

  60. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). Online version (2019-) created by S. J. Chalk. https://doi.org/10.1351/goldbook

  61. Jablonský M, Škulcová A, Malvis A, Šima J (2018) Extraction of value-added components from food industry based and agro-forest biowastes by deep eutectic solvents. J Biotechnol 282:46–66. https://doi.org/10.1016/j.jbiotec.2018.06.349

    Article  CAS  PubMed  Google Scholar 

  62. Kammerer DR, Kammerer J, Valet R, Carle R (2014) Recovery of polyphenols from the by-products of plant food processing and application as valuable food ingredients. Food Res Int 65:2–12. https://doi.org/10.1016/j.foodres.2014.06.012

    Article  CAS  Google Scholar 

  63. Kashtiban AE, Esmaiili M (2019) Extraction of phenolic compounds from Siah-Sardasht grape skin using subcritical water and ultrasound pretreatment. J Food Process Preserv 43:e14071. https://doi.org/10.1111/jfpp.14071

    Article  CAS  Google Scholar 

  64. Kerton F (2009) Alternative solvents for green chemistry. Royal Society of Chemistry, Cambridge

    Google Scholar 

  65. Khan AS, Man Z, Bustam MA, Nasrullah A, Ullah Z, Sarwono A, Shah FU, Muhammad N (2018) Efficient conversion of lignocellulosic biomass to levulinic acid using acidic ionic liquids. Carbohydr Polym 181:208–214. https://doi.org/10.1016/j.carbpol.2017.10.064

    Article  CAS  PubMed  Google Scholar 

  66. Kim M, Sowndhararajan K, Park SJ, Kim S (2018) Effect of inhalation of isomers, (+)-α-pinene and (+)-β-pinene on human electroencephalographic activity according to gender difference. Euro J Integr Med 17:33–39. https://doi.org/10.1016/j.eujim.2017.11.005

    Article  Google Scholar 

  67. Knez Ž, Markočič E, Leitgeb M et al (2014) Industrial applications of supercritical fluids: a review. Energy 77:235–243. https://doi.org/10.1016/j.energy.2014.07.044

    Article  CAS  Google Scholar 

  68. Kruis AJ, Levisson M, Mars AE, van der Ploeg M, Garcés Daza F, Ellena V, Kengen SWM, van der Oost J, Weusthuis RA (2017) Ethyl acetate production by the elusive alcohol acetyltransferase from yeast. Metab Eng 41:92–101. https://doi.org/10.1016/j.ymben.2017.03.004

    Article  CAS  PubMed  Google Scholar 

  69. Kumar AK, Parikh BS, Pravakar M (2016) Natural deep eutectic solvent mediated pretreatment of rice straw: bioanalytical characterization of lignin extract and enzymatic hydrolysis of pretreated biomass residue. Environ Sci Pollut Res 23:9265–9275. https://doi.org/10.1007/s11356-015-4780-4

    Article  CAS  Google Scholar 

  70. Kumar K, Yadav AN, Kumar V et al (2017) Food waste: a potential bioresource for extraction of nutraceuticals and bioactive compounds. Bioresour Bioprocess 4:18–14. https://doi.org/10.1186/s40643-017-0148-6

    Article  Google Scholar 

  71. Kumar AK, Sharma S, Shah E, Patel A (2018) Technical assessment of natural deep eutectic solvent (NADES) mediated biorefinery process: a case study. J Mol Liq 260:313–322. https://doi.org/10.1016/j.molliq.2018.03.107

    Article  CAS  Google Scholar 

  72. Lafka T-I, Lazou AE, Sinanoglou VJ, Lazos ES (2011) Phenolic and antioxidant potential of olive oil mill wastes. Food Chem 125:92–98. https://doi.org/10.1016/j.foodchem.2010.08.041

    Article  CAS  Google Scholar 

  73. Larriba M, Omar S, Navarro P et al (2016) Recovery of tyrosol from aqueous streams using hydrophobic ionic liquids: a first step towards developing sustainable processes for olive mill wastewater (OMW) management. RSC Adv 6:18751–18762. https://doi.org/10.1039/C5RA26510J

    Article  CAS  Google Scholar 

  74. Li C, Wang Q, Zhao ZK (2008) Acid in ionic liquid: an efficient system for hydrolysis of lignocellulose. Green Chem 10:177–182. https://doi.org/10.1039/B711512A

    Article  CAS  Google Scholar 

  75. Li Z, Smith KH, Stevens GW (2016) The use of environmentally sustainable bio-derived solvents in solvent extraction applications—a review. Chin J Chem Eng 24:215–220. https://doi.org/10.1016/j.cjche.2015.07.021

    Article  CAS  Google Scholar 

  76. Li WJ, Fan ZG, Wu YY, Jiang ZG, Shi RC (2019) Eco-friendly extraction and physicochemical properties of pectin from jackfruit peel waste with subcritical water. J Sci Food Agric 99:5283–5292. https://doi.org/10.1002/jsfa.9729

    Article  CAS  PubMed  Google Scholar 

  77. Liu SX, Mamidipally PK (2005) Quality comparison of rice bran oil extracted with d-limonene and hexane. Cereal Chem 82:209–215. https://doi.org/10.1094/CC-82-0209

    Article  CAS  Google Scholar 

  78. Liu W, Zhao W, Chen J, Yang M (2007) A cloud point extraction approach using Triton X-100 for the separation and preconcentration of Sudan dyes in chilli powder. Anal Chim Acta 605:41–45. https://doi.org/10.1016/j.aca.2007.10.034

    Article  CAS  PubMed  Google Scholar 

  79. Liu Y, Liu B, Nie Z (2015) Concurrent self-assembly of amphiphiles into nanoarchitectures with increasing complexity. Nano Today 10:278–300. https://doi.org/10.1016/j.nantod.2015.04.001

    Article  CAS  Google Scholar 

  80. Loow Y-L, New EK, Yang GH et al (2017) Potential use of deep eutectic solvents to facilitate lignocellulosic biomass utilization and conversion. Cellulose 24:3591–3618. https://doi.org/10.1007/s10570-017-1358-y

    Article  CAS  Google Scholar 

  81. Lycourghiotis S, Makarouni D, Kordouli E et al (2018) Activation of natural mordenite by various acids: characterization and evaluation in the transformation of limonene into p-cymene. Molec Catal 450:95–103. https://doi.org/10.1016/j.mcat.2018.03.013

    Article  CAS  Google Scholar 

  82. Martins PLG, Braga AR, de Rosso VV (2017) Can ionic liquid solvents be applied in the food industry? Trends Food Sci Technol 66:117–124. https://doi.org/10.1016/j.tifs.2017.06.002

    Article  CAS  Google Scholar 

  83. Masci A, Coccia A, Lendaro E, Mosca L, Paolicelli P, Cesa S (2016) Evaluation of different extraction methods from pomegranate whole fruit or peels and the antioxidant and antiproliferative activity of the polyphenolic fraction. Food Chem 202:59–69. https://doi.org/10.1016/j.foodchem.2016.01.106

    Article  CAS  PubMed  Google Scholar 

  84. Matsuda H, Hirota Y, Kurihara K et al (2013) Liquid–liquid equilibria containing fluorous solvents as environmentally benign solvent. Fluid Phase Equilib 357:71–75. https://doi.org/10.1016/j.fluid.2012.12.037

    Article  CAS  Google Scholar 

  85. Matthäus B (2002) Antioxidant activity of extracts obtained from residues of different oilseeds. J Agric Food Chem 50:3444–3452. https://doi.org/10.1021/jf011440s

    Article  CAS  PubMed  Google Scholar 

  86. Mohammadzadeh M, Honarvar M, Zarei AR, Mashhadi Akbar Boojar M, Bakhoda H (2018) A new approach for separation and recovery of betaine from beet molasses based on cloud point extraction technique. J Food Sci Technol 55:1215–1223. https://doi.org/10.1007/s13197-017-2999-4

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  87. Mouratoglou E, Malliou V, Makris DP (2016) Novel glycerol-based natural eutectic mixtures and their efficiency in the ultrasound-assisted extraction of antioxidant polyphenols from agri-food waste biomass. Waste Biomass Valor 7:1377–1387. https://doi.org/10.1007/s12649-016-9539-8

    Article  CAS  Google Scholar 

  88. Mourtzinos I, Anastasopoulou E, Petrou A, Grigorakis S, Makris D, Biliaderis CG (2016) Optimization of a green extraction method for the recovery of polyphenols from olive leaf using cyclodextrins and glycerin as co-solvents. J Food Sci Technol 53:3939–3947. https://doi.org/10.1007/s13197-016-2381-y

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  89. Munir MT, Kheirkhah H, Baroutian S et al (2018) Subcritical water extraction of bioactive compounds from waste onion skin. J Clean Prod 183:487–494. https://doi.org/10.1016/j.jclepro.2018.02.166

    Article  CAS  Google Scholar 

  90. Naidu DS, Hlangothi SP, John MJ (2018) Bio-based products from xylan: a review. Carbohydr Polym 179:28–41. https://doi.org/10.1016/j.carbpol.2017.09.064

    Article  CAS  PubMed  Google Scholar 

  91. Ndongou Moutombi FJ, Selka A, Fabiano-Tixier A-S et al (2018) Highly selective solvent-free hydrogenation of pinenes to added-value cis-pinane. Comptes Rendus Chimie. https://doi.org/10.1016/j.crci.2018.09.002

    Article  CAS  Google Scholar 

  92. Nyam KL, Tan CP, Karim R et al (2010a) Extraction of tocopherol-enriched oils from Kalahari melon and roselle seeds by supercritical fluid extraction (SFE-CO2). Food Chem 119:1278–1283. https://doi.org/10.1016/j.foodchem.2009.08.007

    Article  CAS  Google Scholar 

  93. Nyam KL, Tan CP, Lai OM et al (2010b) Optimization of supercritical fluid extraction of phytosterol from roselle seeds with a central composite design model. Food Bioprod Process 88:239–246. https://doi.org/10.1016/j.fbp.2009.11.002

    Article  CAS  Google Scholar 

  94. Oliveira ELG, Silvestre AJD, Silva CM (2011) Review of kinetic models for supercritical fluid extraction. Chem Eng Res Des 89:1104–1117. https://doi.org/10.1016/j.cherd.2010.10.025

    Article  CAS  Google Scholar 

  95. Oliveira DA, Mezzomo N, Gomes C, Ferreira SRS (2017) Encapsulation of passion fruit seed oil by means of supercritical antisolvent process. J Supercrit Fluids 129:96–105. https://doi.org/10.1016/j.supflu.2017.02.011

    Article  CAS  Google Scholar 

  96. Pagano I, Piccinelli AL, Celano R et al (2018a) Pressurized hot water extraction of bioactive compounds from artichoke by-products. Electrophoresis 39:1899–1907. https://doi.org/10.1002/elps.201800063

    Article  CAS  Google Scholar 

  97. Pagano I, Sánchez-Camargo ADP, Mendiola JA et al (2018b) Selective extraction of high-value phenolic compounds from distillation wastewater of basil (Ocimum basilicum L.) by pressurized liquid extraction. Electrophoresis. 39:1884–1891. https://doi.org/10.1002/elps.201700442

    Article  CAS  Google Scholar 

  98. Pal CBT, Jadeja GC (2019) Microwave-assisted deep eutectic solvent extraction of phenolic antioxidants from onion (Allium cepa L.) peel: a Box-Behnken design approach for optimization. J Food Sci Technol-Mysore 56:4211–4223. https://doi.org/10.1007/s13197-019-03891-7

    Article  CAS  Google Scholar 

  99. Pandiyan K, Singh A, Singh S et al (2019) Technological interventions for utilization of crop residues and weedy biomass for second generation bio-ethanol production. Renew Energy 132:723–741. https://doi.org/10.1016/j.renene.2018.08.049

    Article  Google Scholar 

  100. Panic M, Gunjevic V, Cravotto G et al (2019) Enabling technologies for the extraction of grape-pomace anthocyanins using natural deep eutectic solvents in up-to-half-litre batches extraction of grape-pomace anthocyanins using NADES. Food Chem 300:125185. https://doi.org/10.1016/j.foodchem.2019.125185

    Article  CAS  PubMed  Google Scholar 

  101. Passos H, Freire MG, Coutinho JAP (2014) Ionic liquid solutions as extractive solvents for value-added compounds from biomass. Green Chem 16:4786–4815. https://doi.org/10.1039/C4GC00236A

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  102. Pena-Pereira F, Tobiszewski M (2017) The application of green solvents in separation processes|ScienceDirect. Elsevier, Amsterdam, Netherlands

    Google Scholar 

  103. Pérez C, Ruiz del Castillo ML, Gil C, Blanch GP, Flores G (2015) Supercritical fluid extraction of grape seeds: extract chemical composition, antioxidant activity and inhibition of nitrite production in LPS-stimulated Raw 264.7 cells. Food Funct 6:2607–2613. https://doi.org/10.1039/c5fo00325c

    Article  PubMed  Google Scholar 

  104. Pighin E, Díez VK, Di Cosimo JI (2017) Kinetic study of the ethyl lactate synthesis from triose sugars on Sn/Al2O3 catalysts. Catal Today 289:29–37. https://doi.org/10.1016/j.cattod.2016.10.002

    Article  CAS  Google Scholar 

  105. Pitchaiah KC, Sujatha K, Deepitha J et al (2018) Recovery of uranium and plutonium from pyrochemical salt matrix using supercritical fluid extraction. J Supercrit Fluids. https://doi.org/10.1016/j.supflu.2018.10.015

    Article  CAS  Google Scholar 

  106. Plaza M, Turner C (2015) Pressurized hot water extraction of bioactives. TrAC Trends Anal Chem 71:39–54. https://doi.org/10.1016/j.trac.2015.02.022

    Article  CAS  Google Scholar 

  107. Plaza M, Abrahamsson V, Turner C (2013) Extraction and neoformation of antioxidant compounds by pressurized hot water extraction from apple byproducts. J Agric Food Chem 61:5500–5510

    Article  CAS  PubMed  Google Scholar 

  108. Procentese A, Johnson E, Orr V, Garruto Campanile A, Wood JA, Marzocchella A, Rehmann L (2015) Deep eutectic solvent pretreatment and subsequent saccharification of corncob. Bioresour Technol 192:31–36. https://doi.org/10.1016/j.biortech.2015.05.053

    Article  CAS  PubMed  Google Scholar 

  109. Radošević K, Ćurko N, Gaurina Srček V et al (2016) Natural deep eutectic solvents as beneficial extractants for enhancement of plant extracts bioactivity. LWT-Food Sci Technol 73:45–51. https://doi.org/10.1016/j.lwt.2016.05.037

    Article  CAS  Google Scholar 

  110. Rezaei F, Yamini Y, Asiabi H et al (2016) Supercritical fluid extraction followed by nanostructured supramolecular solvent extraction for extraction of levonorgestrel and megestrol from whole blood samples. J Supercrit Fluids 107:392–399. https://doi.org/10.1016/j.supflu.2015.10.005

    Article  CAS  Google Scholar 

  111. Roselló-Soto E, Barba FJ, Parniakov O, Galanakis CM, Lebovka N, Grimi N, Vorobiev E (2015) High voltage electrical discharges, pulsed electric field, and ultrasound assisted extraction of protein and phenolic compounds from olive kernel. Food Bioprocess Technol 8:885–894. https://doi.org/10.1007/s11947-014-1456-x

    Article  CAS  Google Scholar 

  112. Ruesgas-Ramón M, Figueroa-Espinoza MC, Durand E (2017) Application of deep eutectic solvents (DES) for phenolic compounds extraction: overview, challenges, and opportunities. J Agric Food Chem 65:3591–3601. https://doi.org/10.1021/acs.jafc.7b01054

    Article  CAS  PubMed  Google Scholar 

  113. Saha K, Dasgupta J, Chakraborty S, Antunes FAF, Sikder J, Curcio S, Santos JC, Arafat HA, Silva SS (2017) Optimization of lignin recovery from sugarcane bagasse using ionic liquid aided pretreatment. Cellulose 24:3191–3207. https://doi.org/10.1007/s10570-017-1330-x

    Article  CAS  Google Scholar 

  114. Santaella MA, Orjuela A, Narváez PC (2015) Comparison of different reactive distillation schemes for ethyl acetate production using sustainability indicators. Chem Eng Process Process Intensif 96:1–13. https://doi.org/10.1016/j.cep.2015.07.027

    Article  CAS  Google Scholar 

  115. Santalad A, Srijaranai S, Burakham R, Glennon JD, Deming RL (2009) Cloud-point extraction and reversed-phase high-performance liquid chromatography for the determination of carbamate insecticide residues in fruits. Anal Bioanal Chem 394:1307–1317. https://doi.org/10.1007/s00216-009-2663-6

    Article  CAS  PubMed  Google Scholar 

  116. Santos DNE, de Souza LL, Ferreira NJ, de Oliveira AL (2015) Study of supercritical extraction from Brazilian cherry seeds (Eugenia uniflora L.) with bioactive compounds. Food Bioprod Process 94:365–374. https://doi.org/10.1016/j.fbp.2014.04.005

    Article  CAS  Google Scholar 

  117. Santos-Zea L, Gutiérrez-Uribe JA, Benedito J (2019) Effect of ultrasound intensification on the supercritical fluid extraction of phytochemicals from Agave salmiana bagasse. J Supercrit Fluids 144:98–107. https://doi.org/10.1016/j.supflu.2018.10.013

    Article  CAS  Google Scholar 

  118. Sarkar D, Choudhury P, Dinda S, Das PK (2018) Vesicle formation by cholesterol based hydrazone tethered amphiphiles: stimuli responsive dissipation of self-assembly. J Colloid Interface Sci 530:67–77. https://doi.org/10.1016/j.jcis.2018.06.064

    Article  CAS  PubMed  Google Scholar 

  119. Satlewal A, Agrawal R, Bhagia S et al (2018) Natural deep eutectic solvents for lignocellulosic biomass pretreatment: recent developments, challenges and novel opportunities. Biotechnol Adv. https://doi.org/10.1016/j.biotechadv.2018.08.009

    Article  CAS  PubMed  Google Scholar 

  120. Shankar M, Chhotaray PK, Agrawal A et al (2017) Protic ionic liquid-assisted cell disruption and lipid extraction from fresh water Chlorella and Chlorococcum microalgae. Algal Res 25:228–236. https://doi.org/10.1016/j.algal.2017.05.009

    Article  Google Scholar 

  121. Sharif KM, Rahman MM, Azmir J et al (2014) Experimental design of supercritical fluid extraction – a review. J Food Eng 124:105–116. https://doi.org/10.1016/j.jfoodeng.2013.10.003

    Article  CAS  Google Scholar 

  122. Silva YPA, Ferreira TAPC, Celli GB, Brooks MS (2019) Optimization of lycopene extraction from tomato processing waste using an eco-friendly ethyl lactate–ethyl acetate solvent: a green valorization approach. Waste Biomass Valor 10:2851–2861. https://doi.org/10.1007/s12649-018-0317-7

    Article  CAS  Google Scholar 

  123. Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082. https://doi.org/10.1021/cr300162p

    Article  CAS  PubMed  Google Scholar 

  124. Sookwong P, Suttiarporn P, Boontakham P, Seekhow P, Wangtueai S, Mahatheeranont S (2016) Simultaneous quantification of vitamin E, γ-oryzanols and xanthophylls from rice bran essences extracted by supercritical CO2. Food Chem 211:140–147. https://doi.org/10.1016/j.foodchem.2016.05.001

    Article  CAS  PubMed  Google Scholar 

  125. Strati IF, Oreopoulou V (2011) Effect of extraction parameters on the carotenoid recovery from tomato waste. Int J Food Sci Technol 46:23–29. https://doi.org/10.1111/j.1365-2621.2010.02496.x

    Article  CAS  Google Scholar 

  126. Strati IF, Oreopoulou V (2014) Recovery of carotenoids from tomato processing by-products – a review. Food Res Int 65:311–321. https://doi.org/10.1016/j.foodres.2014.09.032

    Article  CAS  Google Scholar 

  127. Strati IF, Oreopoulou V (2016) Recovery and isomerization of carotenoids from tomato processing by-products. Waste Biomass Valor 7:843–850. https://doi.org/10.1007/s12649-016-9535-z

    Article  CAS  Google Scholar 

  128. Tan Z-J, Li F-F, Xing J-M (2012) Cloud point extraction of aloe anthraquinones based on non-ionic surfactant aqueous two-phase system. Nat Prod Res 26:1423–1432. https://doi.org/10.1080/14786419.2011.601415

    Article  CAS  PubMed  Google Scholar 

  129. Teixeira A, Baenas N, Dominguez-Perles R et al (2014) Natural bioactive compounds from winery by-products as health promoters: a review. Int J Mol Sci. https://doi.org/10.3390/ijms150915638

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  130. Tomé LIN, Baião V, da Silva W, Brett CMA (2018) Deep eutectic solvents for the production and application of new materials. Appl Mater Today 10:30–50. https://doi.org/10.1016/j.apmt.2017.11.005

    Article  Google Scholar 

  131. Torres-Valenzuela LS, Ballesteros-Gómez A, Sanin A et al (2019) Valorization of spent coffee grounds by supramolecular solvent extraction. Sep Purif Technol 228:115759. https://doi.org/10.1016/j.seppur.2019.115759

    Article  CAS  Google Scholar 

  132. Ueno H, Tanaka M, Machmudah S et al (2008) Supercritical carbon dioxide extraction of valuable compounds from Citrus junos seed. Food Bioprocess Technol 1:357–363. https://doi.org/10.1007/s11947-007-0015-0

    Article  Google Scholar 

  133. Ventura SPM, e Silva FA, Quental MV et al (2017) Ionic-liquid-mediated extraction and separation processes for bioactive compounds: past, present, and future trends. Chem Rev 117:6984–7052. https://doi.org/10.1021/acs.chemrev.6b00550

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  134. Vian M, Breil C, Vernes L et al (2017) Green solvents for sample preparation in analytical chemistry. Curr Opin Green Sustain Chem 5:44–48. https://doi.org/10.1016/j.cogsc.2017.03.010

    Article  Google Scholar 

  135. Villanueva-Bermejo D, Reglero G, Fornari T (2017) Recent advances in the processing of green tea biomolecules using ethyl lactate. A review. Trends Food Sci Technol 62:1–12. https://doi.org/10.1016/j.tifs.2016.12.009

    Article  CAS  Google Scholar 

  136. Virot M, Tomao V, Ginies C, Chemat F (2008) Total lipid extraction of food using D-limonene as an alternative to n-hexane. Chroma 68:311–313. https://doi.org/10.1365/s10337-008-0696-1

    Article  CAS  Google Scholar 

  137. Vovers J, Smith KH, Stevens GW (2017) Chapter 4 - bio-based molecular solvents. In: Pena-Pereira F, Tobiszewski M (eds) The application of green solvents in separation processes, 1st edn. Elsevier, pp 91–110

  138. Wang Y, Gu W (2018) Study on supercritical fluid extraction of solanesol from industrial tobacco waste. J Supercrit Fluids 138:228–237. https://doi.org/10.1016/j.supflu.2018.05.001

    Article  CAS  Google Scholar 

  139. Watanabe H, Tanaka H (1978) A non-ionic surfactant as a new solvent for liquid–liquid extraction of zinc(II) with 1-(2-pyridylazo)-2-naphthol. Talanta 25:585–589. https://doi.org/10.1016/0039-9140(78)80151-9

    Article  CAS  PubMed  Google Scholar 

  140. Wei Z, Qi X, Li T et al (2015) Application of natural deep eutectic solvents for extraction and determination of phenolics in Cajanus cajan leaves by ultra performance liquid chromatography. Sep Purif Technol 149:237–244. https://doi.org/10.1016/j.seppur.2015.05.015

    Article  CAS  Google Scholar 

  141. Xhaxhiu K, Wenclawiak B (2015) Comparison of supercritical CO2 and ultrasonic extraction of orange peel essential oil from Albanian Moro cultivars. J Essential Oil Bearing Plants 18:289–299. https://doi.org/10.1080/0972060X.2015.1010603

    Article  CAS  Google Scholar 

  142. Yang X, Cheng K, Jia G (2019) The molecular dynamics simulation of hydrogen bonding in supercritical water. Phys A: Stat Mech Appl 516:365–375. https://doi.org/10.1016/j.physa.2018.10.022

    Article  CAS  Google Scholar 

  143. Yao G, Wang L, Chen X et al (2019) Measurement and correlation of vapor–liquid equilibrium data for binary and ternary systems composed of (−)-β-caryophyllene, p-cymene and 3-carene at 101.33 kPa. J Chem Thermodyn 128:215–224. https://doi.org/10.1016/j.jct.2018.08.015

    Article  CAS  Google Scholar 

  144. Yara-Varón E, Selka A, Fabiano-Tixier AS, Balcells M, Canela-Garayoa R, Bily A, Touaibia M, Chemat F (2016) Solvent from forestry biomass. Pinane a stable terpene derived from pine tree byproducts to substitute n-hexane for the extraction of bioactive compounds. Green Chemistry 18 (24):6596–6608

    Article  Google Scholar 

  145. Yoo DE, Jeong KM, Han SY, Kim EM, Jin Y, Lee J (2018) Deep eutectic solvent-based valorization of spent coffee grounds. Food Chem 255:357–364. https://doi.org/10.1016/j.foodchem.2018.02.096

    Article  CAS  PubMed  Google Scholar 

  146. Yoon TJ, Lee Y-W (2018) Current theoretical opinions and perspectives on the fundamental description of supercritical fluids. J Supercrit Fluids 134:21–27. https://doi.org/10.1016/j.supflu.2017.11.022

    Article  CAS  Google Scholar 

  147. Yu J, Dandekar DV, Toledo RT, Singh RK, Patil BS (2006) Supercritical fluid extraction of limonoid glucosides from grapefruit molasses. J Agric Food Chem 54:6041–6045. https://doi.org/10.1021/jf060382d

    Article  CAS  PubMed  Google Scholar 

  148. Zahari SMSNS, Amin ATM, Halim NM et al (2018) Deconstruction of Malaysian agro-wastes with inexpensive and bifunctional triethylammonium hydrogen sulfate ionic liquid. AIP Conference Proceedings 1972:030024. https://doi.org/10.1063/1.5041245

    Article  CAS  Google Scholar 

  149. Zainal-Abidin MH, Hayyan M, Hayyan A, Jayakumar NS (2017) New horizons in the extraction of bioactive compounds using deep eutectic solvents: a review. Anal Chim Acta 979:1–23. https://doi.org/10.1016/j.aca.2017.05.012

    Article  CAS  PubMed  Google Scholar 

  150. Zhang Q, Vigier KDO, Royer S, Jérôme F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108–7146. https://doi.org/10.1039/C2CS35178A

    Article  CAS  PubMed  Google Scholar 

  151. Zhang C-W, Xia S-Q, Ma P-S (2016) Facile pretreatment of lignocellulosic biomass using deep eutectic solvents. Bioresour Technol 219:1–5. https://doi.org/10.1016/j.biortech.2016.07.026

    Article  CAS  PubMed  Google Scholar 

  152. Zhou P, Wang X, Liu P et al (2018) Enhanced phenolic compounds extraction from Morus alba L. leaves by deep eutectic solvents combined with ultrasonic-assisted extraction. Ind Crop Prod 120:147–154. https://doi.org/10.1016/j.indcrop.2018.04.071

    Article  CAS  Google Scholar 

Download references

Funding

Authors gratefully acknowledge financial support from Spanish MINECO (Project CTQ2017-83823-R). A. Ballesteros-Gómez acknowledges the funding from Spanish Ministry of Science, Innovation and Universities for a Ramón y Cajal contract (RYC-2015-18482). L.S. Torres-Valenzuela thanks AUIP for her doctoral fellowship.

GAE, gallic acid equivalents (total polyphenolic content); QE, quercetin equivalent (total flavonoids contents)

GAE, gallic acid equivalents

Optimal amphiphile in bold; 5-CGA, 5-chlorogenic acid; 5-CGAE, 5-chlorogenic acid equivalents; TPC, total phenolic compounds

Author information

Authors and Affiliations

  1. Faculty of Engineering, Universidad La Gran Colombia, Armenia, 630004, Colombia

    Laura Sofía Torres-Valenzuela

  2. Department of Analytical Chemistry, Institute of Fine Chemistry and Nanochemistry, Universidad de Córdoba, 14071, Cordoba, Spain

    Laura Sofía Torres-Valenzuela, Ana Ballesteros-Gómez & Soledad Rubio

Authors
  1. Laura Sofía Torres-Valenzuela
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ana Ballesteros-Gómez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Soledad Rubio
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ana Ballesteros-Gómez.

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

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Torres-Valenzuela, L.S., Ballesteros-Gómez, A. & Rubio, S. Green Solvents for the Extraction of High Added-Value Compounds from Agri-food Waste. Food Eng Rev 12, 83–100 (2020). https://doi.org/10.1007/s12393-019-09206-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12393-019-09206-y

Keywords

Search

Navigation