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APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES

Yıl 2019, Cilt: 1 Sayı: 2, 52 - 56, 25.12.2019

Öz




Deep eutectic solvents (DES), known as environmentally friendly,
recyclable, non-poisonous, low volatile, non-flammable and harmless are first
found by Abbott et al. in 2003. In the last decade, scientists are working with
DES in different areas. Mainly, they focus on isolation of cellulose and
lignin. Regard to extractives, to the best of our knowledge DES was not studied
before. In this study, it was aimed to determine the extractive composition of
Scotch pine with deep eutectic solvents.




Pinus sylvestris L. was used as wood material.  As deep eutectic solvent (DES) Choline
chloride (Merck 5.00117), ethylene glycol (Merck 1.00949) and urea (Merck
1.08487) were used with molar ratio of choline chloride; ethylene glycol (1:2
m/m), and choline chloride: urea (1:2 m/m). Sequential soxhelet extraction was
performed first with n-hexane and then acetone-water with 5 g wood sample for 6
hours. With DES two extractions were performed in an ultrasonic (UB) and
hot-water bath (HWB) at 60°C for 30 min. 0.05 g wood samples were used for
these extractions. Identification and quantification were done with GC-MS and
FID-GC.




Similar results were obtained with DES and organic solvents. Fatty acids,
resin acids and stilbenes are the main chemical groups. Oleic acid (1.4-9%),
linoleic acid (1.6-8%) and levopimaric acid (0.6-17.7%) are dominant compounds,
found in all extracts. Also, monomethyl pinosylvin (51.5%) was found in
acetone: water mixture. DES can be an alternative to organic solvents in wood
extraction.




Destekleyen Kurum

Bartın University

Proje Numarası

2018-FEN-A-006

Teşekkür

This study is a part of a project 2018-FEN-A-006 supported by Bartin University

Kaynakça

  • 1.Abbott, A.P., Boothyby, D., Capper, G., Davies, D.L., Rasheed, R.K. (2004). Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126, 9142-9147.
  • 2.Bosiljkova, T., Dujmic, Filip, Bubalo, M.C., Hribar, J., Vidrihb, R., Brnci, M., Zlatic, E., Redovnikovic, I.R., Jokic, S. (2017). Natural deep eutectic solvents and ultrasound-assisted extraction: Green approaches for extraction of wine lees anthocyanins. Food and Bioproducts Processing. 102, 195–203.
  • 3. Fang, W., Hemming, J., Reunanen, M., Eklund, P., Pineiro, E,C., Poljansek, I., Oven, P., Willför, S. (2015). Evaluation of selective extraction methods for recovery of polyphenols from pine. Holzforschung. 67(8).
  • 4. Gu, T.N., Zhang, M.L., Tan, T., Chen, J., Li, Z., Zhang, Q.H., Qui, H.D. (2014). Deep eutectic solvents as novel extraction media for phenolic compounds from model oil. Chemical Communications. 50(79), 11749-11752.
  • 5. Hayyan, A., Mjalli, F.S., AlNashef, I.M., Al-Wahaibi, T., Al-Wahaibi, Y.M., Hashim, M.A. (2012). Fruit sugar-based deep eutectic solvents and their physical properties. Thermochim. Acta. 541, 70-75
  • 6. Hayyan, M., Hashim, M.A., Hayyan, A., Al-Saadi, M.A., AlNashef, I.M., Mirghani, M.E.S., Saheed, O. (2013). Are Deep Eutectic Solvents benign or toxic? Chemosphere. 90, 2193-2195.
  • 7. Hou, Y., Li, Z., Ren, S., Wu, W.(2015). Separation of toluene from toluene/alkane mixtures with phosphonium salt based deep eutectic solvents. Fuel Process. Technol. 135, 99–104
  • 8. Jhong, H.-R., Wong, D.S.-H., Wan, C.-C., Wang, Y.-Y., Wei, T.-C. (2009). A novel deep eutectic solvent-based ionic liquid used as electrolyte for dye-sensitized solar cells. Electrochem. Commun. 11, 209-211.
  • 9. Li, X. and Row K.H. (2016). Development of deep eutectic solvents applied in extraction and separation, J. Sep. Sci. 39, 3505–3520.
  • 10. Liu, Y., Chen, W., Xia, Q., Guo, B., Wang, Q., Liu, S., Liu, Y., Li, J., Yu, H. (2017). Efficient Cleavage of Lignin-Carbohydrate Complexes and Ultrafast Extraction of Lignin Oligomers from Wood Biomass by Microwave-Assisted Treatment with Deep Eutectic Solvent. CHEMSUSCHEM. 10(8), 1692-1700.Lynam, J.G., Kumar, N., Wong, M.J. (2017). Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density. Bioresource Technology. 238, 684-689.
  • 11. Nie, J., Yu, G., Song, Z., Wang, X., Li, Z., She, Y., Lee, M. (2017). Microwave-assisted deep eutectic solvent extraction coupled with headspace solid-phasemicroextraction followed by GC-MS for the analysis of volatile compounds from tobacco. Anal. Methods. 9, 856–863
  • 12. Procentese, A., Jhonson, E., Orr, V., Campanile, A.G., Wood, J.A., Marzocchella, A., Rehmann, L. (2015). Deep eutectic solvent pretreatment and subsequent saccharification of corncob. Bioresource Technology. 192, 31-36.
  • 13. Savluchinske-Feio, S., Curto, M.J.M, Gigante, B., Roseiro, j.C. (2006) Antimicrobial activity of resin acid derivatives, Applied Microbial Biotechnology, 72, 430-436.
  • 14. Shishov, A., Bulatov, A., Locatelli, M., Carradori, S., Andruch, V. (2017). Application of deep eutectic solvents in analytical chemistry. A review. Microchemical Journal. 135, 33-38.
  • 15. Singh, B.S., Lobo, H.R., Shankarling, G.S., 2012. Choline chloride based eutectic solvents: magical catalytic system for carbon-carbon bond formation in the rapid synthesis of β-hydroxy functionalized derivatives. Catal. Commun. 24, 70-74.
  • 16. Soares, B., Tavares, D. J., Amaral, J. L., Silvestre, A. J., Freire, C. S., Coutinho, J. A., (2017). Enhanced solubility of lignin monomeric model compounds and technical lignins in aqueous solutions of deep eutectic solvents. ACS Sustainable Chemistry & Engineering. 5(5), 4056-4065.
  • 17. Vainio-Kaila, T., Kyyhkynen, A., Rautkari, L., Siitonen, A. (2015). Antibacterial Effects of Extracts of Pinus sylvestris and Picea abies against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Streptococcus pneumonia. BioResources. 10(4), 7763-7771
  • 18. Van Osch, D.J.G.P., Kollau, L.J.B.M., Van den Bruinhorst, A., Asikainen, S., Rocha, M.A.A., Kroon, M.C. (2016). Ionic liquids and deep eutectic solvents for lignocellulosic biomass fractionation. Physical Chemistry Chemical Physics. 19(4), 2636-2665.
  • 19. Venäläinen M, Harju A, Saranpää P, Kainulainen P, Tiitta M, Velling P., 2004. The concentration of phenolics in brown-rot decay resistant and susceptible Scots pine heartwood. Wood Sci Technol. 38, 109–118.Yildirim, H. and Holmbom B. (1978). Investigations on the wood extractives of pine species from Turkey.Abo Akademi, 37(4).
  • 20. Wu, S.-H., Caparanga, A.R., Leron, R.B., Li, M.-H. (2012). Vapor pressure of aqueous chlorine chloride-based deep eutectic solvents (ethaline, glycerine, maline and reline) at 30-70 °C. Thermochim. Acta. 544, 1-5.
  • 21. Xu, G.C., Ding, J.C., Han, R.Z., Dong, J.J., Ni, Y. (2016). Enhancing cellulose accessibility of corn stover by deep eutectic solvent pretreatment for butanol fermentation. Bioresource Technology. 203, 364-369.
  • 22. Yildirim, H. and Holmbom B. (1978). Investigations on the wood extractives of pine species from Turkey.Abo Akademi, 37(4).
Yıl 2019, Cilt: 1 Sayı: 2, 52 - 56, 25.12.2019

Öz

Proje Numarası

2018-FEN-A-006

Kaynakça

  • 1.Abbott, A.P., Boothyby, D., Capper, G., Davies, D.L., Rasheed, R.K. (2004). Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126, 9142-9147.
  • 2.Bosiljkova, T., Dujmic, Filip, Bubalo, M.C., Hribar, J., Vidrihb, R., Brnci, M., Zlatic, E., Redovnikovic, I.R., Jokic, S. (2017). Natural deep eutectic solvents and ultrasound-assisted extraction: Green approaches for extraction of wine lees anthocyanins. Food and Bioproducts Processing. 102, 195–203.
  • 3. Fang, W., Hemming, J., Reunanen, M., Eklund, P., Pineiro, E,C., Poljansek, I., Oven, P., Willför, S. (2015). Evaluation of selective extraction methods for recovery of polyphenols from pine. Holzforschung. 67(8).
  • 4. Gu, T.N., Zhang, M.L., Tan, T., Chen, J., Li, Z., Zhang, Q.H., Qui, H.D. (2014). Deep eutectic solvents as novel extraction media for phenolic compounds from model oil. Chemical Communications. 50(79), 11749-11752.
  • 5. Hayyan, A., Mjalli, F.S., AlNashef, I.M., Al-Wahaibi, T., Al-Wahaibi, Y.M., Hashim, M.A. (2012). Fruit sugar-based deep eutectic solvents and their physical properties. Thermochim. Acta. 541, 70-75
  • 6. Hayyan, M., Hashim, M.A., Hayyan, A., Al-Saadi, M.A., AlNashef, I.M., Mirghani, M.E.S., Saheed, O. (2013). Are Deep Eutectic Solvents benign or toxic? Chemosphere. 90, 2193-2195.
  • 7. Hou, Y., Li, Z., Ren, S., Wu, W.(2015). Separation of toluene from toluene/alkane mixtures with phosphonium salt based deep eutectic solvents. Fuel Process. Technol. 135, 99–104
  • 8. Jhong, H.-R., Wong, D.S.-H., Wan, C.-C., Wang, Y.-Y., Wei, T.-C. (2009). A novel deep eutectic solvent-based ionic liquid used as electrolyte for dye-sensitized solar cells. Electrochem. Commun. 11, 209-211.
  • 9. Li, X. and Row K.H. (2016). Development of deep eutectic solvents applied in extraction and separation, J. Sep. Sci. 39, 3505–3520.
  • 10. Liu, Y., Chen, W., Xia, Q., Guo, B., Wang, Q., Liu, S., Liu, Y., Li, J., Yu, H. (2017). Efficient Cleavage of Lignin-Carbohydrate Complexes and Ultrafast Extraction of Lignin Oligomers from Wood Biomass by Microwave-Assisted Treatment with Deep Eutectic Solvent. CHEMSUSCHEM. 10(8), 1692-1700.Lynam, J.G., Kumar, N., Wong, M.J. (2017). Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density. Bioresource Technology. 238, 684-689.
  • 11. Nie, J., Yu, G., Song, Z., Wang, X., Li, Z., She, Y., Lee, M. (2017). Microwave-assisted deep eutectic solvent extraction coupled with headspace solid-phasemicroextraction followed by GC-MS for the analysis of volatile compounds from tobacco. Anal. Methods. 9, 856–863
  • 12. Procentese, A., Jhonson, E., Orr, V., Campanile, A.G., Wood, J.A., Marzocchella, A., Rehmann, L. (2015). Deep eutectic solvent pretreatment and subsequent saccharification of corncob. Bioresource Technology. 192, 31-36.
  • 13. Savluchinske-Feio, S., Curto, M.J.M, Gigante, B., Roseiro, j.C. (2006) Antimicrobial activity of resin acid derivatives, Applied Microbial Biotechnology, 72, 430-436.
  • 14. Shishov, A., Bulatov, A., Locatelli, M., Carradori, S., Andruch, V. (2017). Application of deep eutectic solvents in analytical chemistry. A review. Microchemical Journal. 135, 33-38.
  • 15. Singh, B.S., Lobo, H.R., Shankarling, G.S., 2012. Choline chloride based eutectic solvents: magical catalytic system for carbon-carbon bond formation in the rapid synthesis of β-hydroxy functionalized derivatives. Catal. Commun. 24, 70-74.
  • 16. Soares, B., Tavares, D. J., Amaral, J. L., Silvestre, A. J., Freire, C. S., Coutinho, J. A., (2017). Enhanced solubility of lignin monomeric model compounds and technical lignins in aqueous solutions of deep eutectic solvents. ACS Sustainable Chemistry & Engineering. 5(5), 4056-4065.
  • 17. Vainio-Kaila, T., Kyyhkynen, A., Rautkari, L., Siitonen, A. (2015). Antibacterial Effects of Extracts of Pinus sylvestris and Picea abies against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Streptococcus pneumonia. BioResources. 10(4), 7763-7771
  • 18. Van Osch, D.J.G.P., Kollau, L.J.B.M., Van den Bruinhorst, A., Asikainen, S., Rocha, M.A.A., Kroon, M.C. (2016). Ionic liquids and deep eutectic solvents for lignocellulosic biomass fractionation. Physical Chemistry Chemical Physics. 19(4), 2636-2665.
  • 19. Venäläinen M, Harju A, Saranpää P, Kainulainen P, Tiitta M, Velling P., 2004. The concentration of phenolics in brown-rot decay resistant and susceptible Scots pine heartwood. Wood Sci Technol. 38, 109–118.Yildirim, H. and Holmbom B. (1978). Investigations on the wood extractives of pine species from Turkey.Abo Akademi, 37(4).
  • 20. Wu, S.-H., Caparanga, A.R., Leron, R.B., Li, M.-H. (2012). Vapor pressure of aqueous chlorine chloride-based deep eutectic solvents (ethaline, glycerine, maline and reline) at 30-70 °C. Thermochim. Acta. 544, 1-5.
  • 21. Xu, G.C., Ding, J.C., Han, R.Z., Dong, J.J., Ni, Y. (2016). Enhancing cellulose accessibility of corn stover by deep eutectic solvent pretreatment for butanol fermentation. Bioresource Technology. 203, 364-369.
  • 22. Yildirim, H. and Holmbom B. (1978). Investigations on the wood extractives of pine species from Turkey.Abo Akademi, 37(4).
Toplam 22 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Articles
Yazarlar

Ayben Kılıç-pekgözlü 0000-0002-3640-6198

Esra Ceylan 0000-0002-5336-4698

Proje Numarası 2018-FEN-A-006
Yayımlanma Tarihi 25 Aralık 2019
Kabul Tarihi 27 Kasım 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 1 Sayı: 2

Kaynak Göster

APA Kılıç-pekgözlü, A., & Ceylan, E. (2019). APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES. Wood Industry and Engineering, 1(2), 52-56.
AMA Kılıç-pekgözlü A, Ceylan E. APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES. WI&E. Aralık 2019;1(2):52-56.
Chicago Kılıç-pekgözlü, Ayben, ve Esra Ceylan. “APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES”. Wood Industry and Engineering 1, sy. 2 (Aralık 2019): 52-56.
EndNote Kılıç-pekgözlü A, Ceylan E (01 Aralık 2019) APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES. Wood Industry and Engineering 1 2 52–56.
IEEE A. Kılıç-pekgözlü ve E. Ceylan, “APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES”, WI&E, c. 1, sy. 2, ss. 52–56, 2019.
ISNAD Kılıç-pekgözlü, Ayben - Ceylan, Esra. “APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES”. Wood Industry and Engineering 1/2 (Aralık 2019), 52-56.
JAMA Kılıç-pekgözlü A, Ceylan E. APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES. WI&E. 2019;1:52–56.
MLA Kılıç-pekgözlü, Ayben ve Esra Ceylan. “APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES”. Wood Industry and Engineering, c. 1, sy. 2, 2019, ss. 52-56.
Vancouver Kılıç-pekgözlü A, Ceylan E. APPLICATION OF DES (DEEP EUTECTIC SOLVENTS) TO WOOD EXTRACTIVES. WI&E. 2019;1(2):52-6.

Wood Industry and Engineering Journal
 Correspondence: Karadeniz Technical University, Faculty of Forestry, Department of Forest Industry Engineering, Kanuni Campus, 61080, Trabzon / TURKEY
Contact E-mail: engin_gezer@yahoo.com (Editor - Assoc. Prof. Dr. Engin Derya GEZER),   iaydin@ktu.edu.tr  (Co-Editor - Prof. Dr. Ismail AYDIN)
Phone: +90 (462) 377 1532,  Fax: +90 (462) 325 7499