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Synthesis of Hyper-cross-linked Nonpolar Polystyrene Divinylbenzene Resins by Pendent Vinyl Groups and Application to the Decolorization of Cane Molasses

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Abstract

Cane molasses is a by-product of sugar industry. It is widely used in fermentation field, but pigment compounds affect its further application. In this study, nonpolar hyper-cross-linked adsorption resins (HCARs) were synthesized by pendent vinyl groups cross-linking reaction, and were applied to decolorization of molasses. The correlation between the structure and the decolorization performance of HCARs was studied, and the results showed that the Brunauer–Emmett–Teller (BET) surface area and the pore volume of the resin significantly increased to 574.4 m2·g−1 and 1.40 cm3·g−1 after the Friedel–Crafts alkylation reaction with a catalyst dosage of 2.25% at 343 K for 7 h. Furthermore, the decolorization rate of molasses by the HCAR was 74%, and recycle decolorization performance of the resin was stable. The adsorption kinetics results showed that the pseudo-second-order dynamic model could more realistically reflect the decolorization mechanism of molasses on HCARs, and liquid film diffusion is the main rate-limiting step. The results of fixed-bed experiments show that D-ST-DVB resin has a good decolorization effect and recycling ability. Therefore, it is a feasible strategy for the decolorization of molasses with nonpolar HCAR.

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Data Availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

References

  1. Amid, S., Aghbashlo, M., Tabatabaei, M., Karimi, K., Nizami, A.-S., Rehan, M., Hosseinzadeh-Bandbafha, H., Soufiyan, M. M., Peng, W., & Lam, S. S. (2021). Exergetic, exergoeconomic, and exergoenvironmental aspects of an industrial-scale molasses-based ethanol production plant. Energy Conversion and Management, 227, 113637.

    Article  CAS  Google Scholar 

  2. Chuang, T., & Lai, C. (1978) Study on treatment and utilization of molasses alcohol slop. In Proceedings of the international conference on water pollution control in developing countries. Asia Institute of Technology, pp. 513–524

  3. Xu, W., Liang, L., & Zhu, M. (2015). Determination of sugars in molasses by HPLC following solid-phase extraction. International Journal of Food Properties, 18, 547–557.

    Article  CAS  Google Scholar 

  4. Kitts, D. D., Wu, C. H., Stich, H. F., & Powrie, W. D. (1993). Effect of glucose-lysine Maillard reaction products on bacterial and mammalian cell mutagenesis. Journal of Agricultural and Food Chemistry, 41, 2353–2358.

    Article  CAS  Google Scholar 

  5. Kumar, V., Wati, L., FitzGibbon, F., Nigam, P., Banat, I., Singh, D., & Marchant, R. (1997). Bioremediation and decolorization of anaerobically digested distillery spent wash. Biotechnology Letters, 19, 311–314.

    Article  CAS  Google Scholar 

  6. Zhang, Z., Wang, W., Li, D., Xiao, J., Wu, L., Geng, X., Wu, G., Zeng, Z., & Hu, J. (2021). Decolorization of molasses alcohol wastewater by thermophilic hydrolase with practical application value. Bioresource Technology, 323, 124609.

    Article  CAS  PubMed  Google Scholar 

  7. Migo, V. P., Matsumura, M., Del Rosario, E. J., & Kataoka, H. (1993). Decolorization of molasses wastewater using an inorganic flocculant. Journal of Fermentation and Bioengineering, 75, 438–442.

    Article  CAS  Google Scholar 

  8. Sirianuntapiboon, S., Zohsalam, P., & Ohmomo, S. (2004). Decolorization of molasses wastewater by Citeromyces sp. WR-43-6. Process biochemistry, 39, 917–924.

    Article  CAS  Google Scholar 

  9. Agarwal, R., Lata, S., Gupta, M., & Singh, P. (2010). Removal of melanoidin present in distillery effluent as a major colorant: A review. Journal of Environmental Biology, 31, 521–528.

    CAS  PubMed  Google Scholar 

  10. Qiang, X., Luo, J., Guo, S., Cao, W., Hang, X., Liu, J., & Wan, Y. (2019). A novel process for molasses utilization by membrane filtration and resin adsorption. Journal of Cleaner Production, 207, 432–443.

    Article  CAS  Google Scholar 

  11. Luo, J., Guo, S., Qiang, X., Hang, X., Chen, X., & Wan, Y. (2019). Sustainable utilization of cane molasses by an integrated separation process: Interplay between adsorption and nanofiltration. Separation and Purification Technology, 219, 16–24.

    Article  CAS  Google Scholar 

  12. Hatano, K.-I., Kikuchi, S., Nakamura, Y., Sakamoto, H., Takigami, M., & Kojima, Y. (2009). Novel strategy using an adsorbent-column chromatography for effective ethanol production from sugarcane or sugar beet molasses. Bioresource technology, 100, 4697–4703.

    Article  CAS  PubMed  Google Scholar 

  13. Wang, B.-S., Li, B.-S., Zeng, Q.-X., & Liu, H.-X. (2008). Antioxidant and free radical scavenging activities of pigments extracted from molasses alcohol wastewater. Food chemistry, 107, 1198–1204.

    Article  CAS  Google Scholar 

  14. Zeng, X., & Huang, J. (2020). Anisole-modified hyper-cross-linked resins for efficient adsorption of aniline from aqueous solution. Journal of Colloid and Interface Science, 569, 177–183.

    Article  CAS  PubMed  Google Scholar 

  15. Wang, X., Li, H., & Huang, J. (2017). Adsorption of p-chlorophenol on three amino-modified hyper-cross-linked resins. Journal of colloid and interface science, 505, 585–592.

    Article  CAS  PubMed  Google Scholar 

  16. Zhang, T., & Huang, J. (2017). Tunable synthesis of the polar modified hyper-cross-linked resins and application to the adsorption. Journal of colloid and interface science, 505, 383–391.

    Article  CAS  PubMed  Google Scholar 

  17. Streat, M. (1989). Ion exchange for industry. Hydrometallurgy, 22, 281–282.

  18. Ling, X., Li, H., Zha, H., He, C., & Huang, J. (2016). Polar-modified post-cross-linked polystyrene and its adsorption towards salicylic acid from aqueous solution. Chemical Engineering Journal, 286, 400–407.

    Article  CAS  Google Scholar 

  19. Zheng, J., Hu, L., He, X., Liu, Y., Zheng, X., Tao, S., & Lin, X. (2020). Evaluation of pore structure of polarity-controllable post-cross-linked adsorption resins on the adsorption performance of 5-hydroxymethylfurfural in both single-and ternary-component systems. Industrial & Engineering Chemistry Research, 59, 17575–17586.

    Article  CAS  Google Scholar 

  20. Lin, X., Huang, Q., Qi, G., Xiong, L., Huang, C., Chen, X., Li, H., & Chen, X. (2017). Adsorption behavior of levulinic acid onto microporous hyper-cross-linked polymers in aqueous solution: Equilibrium, thermodynamic, kinetic simulation and fixed-bed column studies. Chemosphere, 171, 231–239.

    Article  CAS  PubMed  Google Scholar 

  21. Ahn, J.-H., Jang, J.-E., Oh, C.-G., Ihm, S.-K., Cortez, J., & Sherrington, D. C. (2006). Rapid generation and control of microporosity, bimodal pore size distribution, and surface area in Davankov-type hyper-cross-linked resins. Macromolecules, 39, 627–632.

    Article  CAS  Google Scholar 

  22. Wang, X., Fu, Z., Yu, N., & Huang, J. (2016). A novel polar-modified post-cross-linked resin: Effect of the porogens on the structure and adsorption performance. Journal of Colloid and Interface Science, 466, 322–329.

    Article  CAS  PubMed  Google Scholar 

  23. Zhou, F., Huang, J., & Man, R. (2018). N-vinylimidazole-modified post-cross-linked resin with pendent vinyl groups and their adsorption of phenol from aqueous solution. Journal of Chemical & Engineering Data, 63, 3584–3591.

    Article  CAS  Google Scholar 

  24. Zeng, X., Yu, T., Wang, P., Yuan, R., Wen, Q., Fan, Y., Wang, C., & Shi, R. (2010). Preparation and characterization of polar polymeric adsorbents with high surface area for the removal of phenol from water. Journal of Hazardous Materials, 177, 773–780.

    Article  CAS  PubMed  Google Scholar 

  25. Sing, K. (2001). The use of nitrogen adsorption for the characterisation of porous materials. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 187, 3–9.

    Article  Google Scholar 

  26. Huang, J., Wang, X., & Deng, X. (2009). Synthesis, characterization, and adsorption properties of phenolic hydroxyl group modified hyper-cross-linked polymeric adsorbent. Journal of Colloid and Interface Science, 337, 19–23.

    Article  CAS  PubMed  Google Scholar 

  27. Zhou, C., Yan, J., & Cao, Z. (2002). Postcrosslinking of macroporous styrene–divinylbenzene copolymers via pendant vinyl groups: Effect of the starting copolymers on the pore structure of the postcrosslinked products. Journal of Applied Polymer Science, 83, 1668–1677.

    Article  CAS  Google Scholar 

  28. Walker, G., & Weatherley, L. (2001). Adsorption of dyes from aqueous solution—The effect of adsorbent pore size distribution and dye aggregation. Chemical Engineering Journal, 83, 201–206.

    Article  CAS  Google Scholar 

  29. Peng, X., Yang, P., Dai, K., Chen, Y., Chen, X., Zhuang, W., Ying, H., & Wu, J. (2020). Synthesis, adsorption and molecular simulation study of methylamine-modified hyper-cross-linked resins for efficient removal of citric acid from aqueous solution. Scientific Reports, 10, 1–13.

    Google Scholar 

  30. Mıynat, M. E., & Argun, H. (2020). Prevention of substrate and product inhibitions by using a dilution strategy during dark fermentative hydrogen production from molasses. International Journal of Hydrogen Energy, 45, 34695–34706.

    Article  Google Scholar 

  31. Xu, W., Yao, S., Ji, X., Zhang, H., Chen, X., & Chen, X. (2022). Effective recovery of Au from low-concentration solutions by a self-synthesized mesoporous resin modified by dimethylamine. Industrial & Engineering Chemistry Research, 61, 2894–2903.

    Article  CAS  Google Scholar 

  32. Zhou, Y., Liu, X., Xiang, Y., Wang, P., Zhang, J., Zhang, F., Wei, J., Luo, L., Lei, M., & Tang, L. (2017). Modification of biochar derived from sawdust and its application in removal of tetracycline and copper from aqueous solution: Adsorption mechanism and modelling. Bioresource Technology, 245, 266–273.

    Article  CAS  PubMed  Google Scholar 

  33. Danish, M., Ansari, K. B., Danish, M., Khatoon, A., Rao, R. A. K., Zaidi, S., & Aftab, R. A. (2022). A comprehensive investigation of external mass transfer and intraparticle diffusion for batch and continuous adsorption of heavy metals using pore volume and surface diffusion model. Separation and Purification Technology, 292, 120996.

    Article  CAS  Google Scholar 

  34. Wei, L., Wang, S., Zhang, F., Fan, Y., Liao, Y., Liao, B., Wang, W., Tu, J., Xiao, J., & Wu, G. (2022). Efficient degradation of molasses wastewater from sugar mill by lipase via addition reaction. LWT, 161, 113366.

    Article  CAS  Google Scholar 

  35. Rane, M. D., Rathi, P. & Tambe, R. R. (2018) Microbial decolorization and bioremediation of melanoidin containing molasses spent wash. World Journal of Pharmaceutical Research, 7, 222–230.

  36. Wilk, M., Krzywonos, M., Seruga, P., & Walaszczyk, E. (2019). Effect of pH and temperature on vinasse decolorization by lactic acid bacteria in batch processes. Water Environment Research, 91, 573–580.

    Article  CAS  PubMed  Google Scholar 

  37. Mudoga, H., Yucel, H., & Kincal, N. (2008). Decolorization of sugar syrups using commercial and sugar beet pulp based activated carbons. Bioresource technology, 99, 3528–3533.

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

The authors acknowledge the Project of National Natural Science Foundation of China (51876207, 52006229), the Project of Zhongke Bengbu Technology Transfer Center (ZKBB202009), the Henan province-CAS scientific and technical payoffs transformation project (2021114), and the Guangdong Provincial Key Laboratory of New and Renewable Energy Research and Development (E1390104).

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Authors and Affiliations

  1. Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, No. 2 Nengyuan Road, Tianhe District, Guangzhou, 510640, People’s Republic of China

    Xuran Ji, Zhijie Shen, Wenping Xu, Shimiao Yao, Lian Xiong, Hairong Zhang, Xuefang Chen & Xinde Chen

  2. University of Chinese Academy of Sciences, No. 19 Yuquan Road, Beijing, 100049, People’s Republic of China

    Xuran Ji & Xuefang Chen

  3. School of Energy Science and Engineering, University of Science and Technology of China, Hefei, China

    Zhijie Shen

  4. Guangdong Zhongke Tianyuan New Energy S&T Co. Ltd., No. 4 Nengyuan Road, Tianhe District, Guangzhou, 510640, People’s Republic of China

    Hongcai Zhou

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  1. Xuran Ji
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Contributions

All authors contributed to the study conception and design. Material preparation was performed by Wenping Xu, Xuefang Chen, Hongcai Zhou, and Shimiao Yao; data collection and analysis were performed by Zhijie Shen, Hairong Zhang, Xiong Lian, and Xinde Chen. The first draft of the manuscript was written by Xuran Ji and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Xuefang Chen or Xinde Chen.

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Ji, X., Shen, Z., Xu, W. et al. Synthesis of Hyper-cross-linked Nonpolar Polystyrene Divinylbenzene Resins by Pendent Vinyl Groups and Application to the Decolorization of Cane Molasses. Appl Biochem Biotechnol 195, 3406–3424 (2023). https://doi.org/10.1007/s12010-022-04308-6

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