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Homogeneous acetylation of hemicelluloses from soy sauce residue in imidazolium-based ionic liquid

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Abstract

The acetylation of hemicelluloses isolated from deoiled soy sauce residue by a novel process was achieved in a complete homogeneous imidazolium-based ionic liquid system with acetic anhydride for the first time. The key parameters of acetylation reaction were studied, which included the acetic anhydride/hydroxyl functionality in hemicellulose ratio, reaction time and temperature. The degree of substitution (DS) of acetylated hemicelluloses ranged between 0.67 and 1.68 as a function of experiment conditions. Under the optimal reaction conditions (14:1 molar ratio of acetic anhydride to hydroxyl functionality, 20 min reaction time and 100 °C reaction temperature) developed by orthogonal method, over 90 % hydroxyl groups in hemicelluloses were acetylated. The structural features of the acetylated hemicelluloses were characterized by means of SEM, FT-IR, TG and 13CNMR. The thermal stability of the acetylated hemicelluloses increased upon chemical modification. At the end of acetylation of hemicelluloses, the ionic liquid could be effectively recovered and reused for at least four times with similar DS values. This study presents a promising approach and green process to make use of soy sauce residue and other similar waste materials.

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References

  1. Li B, Wu ZQ, Dong LY, Li L (2012) Purification of soybean isoflavones from soy sauce residue by ultrafiltration. Adv Mater Res 581–582:1184–1188

    Google Scholar 

  2. Asada C, Kondo Y, Sasaki C, Nakamura Y (2010) Bioconversion of soy sauce residue treated with steam explosion into ethanol by Meicelase and Mucor indicus. J Food Tech 8:187–190

    Article  Google Scholar 

  3. Murasawa N, Koseki H, Iwata Y (2013) Causes of accidents by soy sauce squeezing residue and fish meal. J Mater Cycles Waste Manag 15:42–48

    Article  Google Scholar 

  4. Yang YY (2012) Study of comprehensive development and utilization of soy sauce residue. Master Dissertation, Sichuan University

  5. Fang JM, Sun RC, Tomkinson J, Fowler P (2000) Acetylation of wheat straw hemicelluloses B in a new non-aqueous swelling system. Carbohydr Polym 41:379–387

    Article  Google Scholar 

  6. Xu F, Sun RC, Sun XF (2004) Analysis and characterization of acetylated sugarcane bagasse hemicelluloses. Int J Polym Anal Ch 9:229–244

    Article  Google Scholar 

  7. Fang JM, Sun RC, Fowler P (1999) Esterification of wheat straw hemicelluloses in the N, N-dimethylformamide/lithium chloride homogeneous system. J Appl Polym Sci 74:2301–2311

    Article  Google Scholar 

  8. Girio FM, Fonseca C, Carvalheiro F (2010) Hemicelluloses for fuel ethanol: a review. Bioresour Technol 101:4775–4800

    Article  Google Scholar 

  9. Quan JY, Wang PQ (1997) Preparation of carboxymethyl modified hemicelluloses and its application potential. Chem Ind For Prod 17(4):25–31

    Google Scholar 

  10. Ebringerová Z, Hromádková A (2000) Structure and properties of water-soluble p-carboxybenzyl polysaccharide derivatives. J Appl Polym Sci 78:1181–1199

    Article  Google Scholar 

  11. Sun RC, Sun XF (2002) Fractional and structural characterization of hemicelluloses isolated by alkali and alkali peroxide from barley straw. Carbohydr Polym 49:415–423

    Article  Google Scholar 

  12. Peng YY, Wu SB (2010) The structural and thermal characteristics of wheat straw hemicellulose. J Anal Appl Pyrol 88:134–139

    Article  Google Scholar 

  13. Sun JX, Sun XF, Sun RC (2004) Fractional extraction and structural characterization of sugarcane bagasse hemicelluloses. Carbohyd Polym 56:195–204

    Article  Google Scholar 

  14. Fang JM, Sun RC, Salisbury D (1999) Comparative study of hemicelluloses from wheat straw by alkali and hydrogen peroxide extractions. Polym Degrad Stab 66:423–432

    Article  Google Scholar 

  15. Ayoub A, Venditti RA, Pawlak JJ (2013) Development of an acetylation reaction of switchgrass hemicellulose in ionic liquid without catalyst. Ind Crop Prod 44:306–314

    Article  Google Scholar 

  16. Moens L, Khan N (2002) Application of room-temperature ionic liquids to the chemical processing of biomass-derived feed-stocks. NATO Sci Ser II Math Phys Chem 92:157–171

    Google Scholar 

  17. Köhler S, Liebert T, Heinze T (2008) Interactions of ionic liquids with polysaccharides. VI. Pure cellulose nanoparticles from trimethylsilyl cellulose synthesized in ionic liquids. J Polym Sci Poly Chem 46(12):4070–4080

    Article  Google Scholar 

  18. Swatloski RP, Spear SK (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975

    Article  Google Scholar 

  19. Ren JL, Sun RC, Liu CF (2007) Acetylation of wheat straw hemicelluloses in ionic liquid using iodine as a catalyst. Carbohydr Polym 70:406–414

    Article  Google Scholar 

  20. Studzinska S, Buszewski B (2010) Study of retention mechanism of imidazolium-based ionic liquids in HPLC. J Sep Sci 33:1264–1273

    Google Scholar 

  21. Hu RF, Lin L, Liu TJ (2008) Reducing sugar content in hemicellulose hydrolysate by DNS method: a revisit. J Biobased Mater Bioenergy 2(2):156–161

    Article  Google Scholar 

  22. Xiong SM, Zuo XF, Zhu YY (2005) Determination of cellulose, hemicellulose and lignin in rice hull. Cereal Feed Ind 8:40–41

    Google Scholar 

  23. Lepeniotis S (1997) Synthesis of starch acetate: statistical designed experiments to optimize the reaction conditions. Chemom Intell Lab 36(2):229–243

    Article  Google Scholar 

  24. Chen HZ, Liu LY (2007) Unpolluted fractionation of wheat straw by steam explosion and ethanol extraction. Bioresour Technol 98:666–676

    Article  Google Scholar 

  25. Pandey KK (1998) A study of chemical structure of soft and hardwood and wood polymers by FTIR spectroscopy. J Appl Polym Sci 71:1969–1975

    Article  Google Scholar 

  26. Grondahl M, Teleman A, Gatenholm P (2003) Effect of acetylation on the material properties of glucuronoxylan from aspen wood. Carbohydr Polym 52:359–366

    Article  Google Scholar 

  27. Zhang H, Wu J, Zhang J, He J (2005) 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 38(20):8272–8277

    Article  Google Scholar 

Download references

Acknowledgments

This research was supported by National Scientific Foundation of China (No. 81373284, 81102344).

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Correspondence to Shun Yao.

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Chen, P., Song, H., Wang, Y. et al. Homogeneous acetylation of hemicelluloses from soy sauce residue in imidazolium-based ionic liquid. J Mater Cycles Waste Manag 17, 574–582 (2015). https://doi.org/10.1007/s10163-014-0287-1

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  • DOI: https://doi.org/10.1007/s10163-014-0287-1

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