Korean Chemical Engineering Research

The Korean Institute of Chemical Engineers (한국화학공학회)
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A Study on Extraction and Adsorption of Three Phenolic Ketones

페놀케톤 3종의 추출 및 흡착에 관한 연구

  • Sang Cheol, Lee (Department of Chemical Engineering, Kunsan National University)
  • Received : 2022.09.06
  • Accepted : 2022.10.17
  • Published : 2023.02.01
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Abstract

The extraction and adsorption characteristics for three phenolic ketones with high physicochemical similarity among phenolic compounds, which are alcohol fermentation inhibitors in lignocellulosic biomass hydrolysates, were investigated. The most suitable basic extractant for selectively separating acetosyringone from three phenol ketones by reactive extraction was found to be trioctylphosphine oxide. In addition, it was found that adsorption using XAD16, a polymer neutral resin adsorbent, or physical extraction using hexane, was a suitable separation method for separation of 4'-hydroxyacetophenone (HAP) and acetovanillone (AVO). A five-step fractionation process including extraction and adsorption mentioned above has been first proposed to separate and concentrate the three phenol ketones present at equal mass percentages. When physical extraction with n-hexane and re-extraction with an aqueous NaOH solution were used as the steps 4 and 5 in the fractionation process respectively, it was possible to obtain almost 70% or more of the purity of three phenolic ketones.

목질계 바이오매스 가수분해액에 존재하는 알코올 발효 저해물질인 페놀화합물 중 물리화학적 유사성이 높은 페놀케톤 3종에 대한 추출 및 흡착 특성을 조사하였다. 반응추출을 이용하여 페놀케톤 3종으로 부터 acetosyringone을 선택적으로 분리하는 데 가장 적합한 염기성 추출제가 trioctylphosphine oxide라는 것이 밝혀졌다. 또한, 고분자 중성수지 흡착제인 XAD16을 이용한 흡착 또는 hexane을 이용한 물리추출이 4'-hydroxyacetophenone (HAP)과 acetovanillone (AVO)의 분리에 적합한 분리 방법임을 알 수 있었다. 동등한 질량백분율로 존재하는 페놀케톤 3종을 분리 및 농축하기 위하여 위에서 언급한 추출 및 흡착을 포함한 5단계 분별화 공정이 처음으로 제안되었다. 분별화 공정의 단계 4와 5로서 hexane에 의한 물리추출 및 NaOH 용액에 의한 역추출이 각각 사용되었을 때, 페놀케톤 3종의 순도를 거의 70% 이상 얻는 것이 가능하였다.

Keywords

Acknowledgement

이 논문은 2020년도 군산대학교 연구교수경비의 지원에 의하여 연구되었음. 이 논문은 정부(과학기술정보통신부)의 재원으로 한국연구재단의 지원을 받아 수행된 연구임(No. 2019R1A2C1011556).

References

  1. Sousa, L. C. S., Chundawat, S. P. S., Balan V. and Dale, B. E., "Cradle-to-grave Assessment of Existing Lignocellulose Pretreatment Technologies," Current Opinion in Biotechnology, 20, 339-347(2009). https://doi.org/10.1016/j.copbio.2009.05.003
  2. Lee, S. C. and Kim, E. H., "Affinity Characteristics of Neutral and Anion Exchange Polymer Resin Adsorbents for Main Components in a Siumulated Biomass Hydrolysate," J. Ind. Eng. Chem., 91, 223-230(2020). https://doi.org/10.1016/j.jiec.2020.08.003
  3. Mota, I. F., Pinto, P. R., Loureiro, J. M. and Rodrigues, A. E., "Purification of Syringaldehyde and Vanillin from An Oxidized Industrial Kraft Liquor by Chromatographic Processes," Sep. Purif. Technol., 234, 116083(2020).
  4. Li, Y., Qi, B., Luo, J., Khan, R. and Wan, Y., "Separation and Concentration of Hydroxycinnamic Acids in Alkaline Hydrolyzate from Rice Straw by Nanofiltration," Sep. Purif. Technol., 149, 315(2015).
  5. Domingos, J. M. B., Teixeira, A. R. S., Dupoiron, S., Allaisa, F. and Lameloise, M., "Simultaneous Recovery of Ferulic Acid and Sugars from Wheat Bran Enzymatic Hydrolysate by Diananofiltration," Sep. Purif. Technol., 242, 116755(2020).
  6. Lee, S. C. and Park, S., "Removal of Furan and Phenolic Compounds from Simulated Biomass Hydrolysates by Batch Adsorption and Continuous Fixed-bed Column Adsorption Methods," Bioresource Technol., 216, 661-668(2016). https://doi.org/10.1016/j.biortech.2016.06.007
  7. Lee, S. C., "Removal and Recovery of Acetic Acid and Two Furans During Sugar Purification of Simulated Phenols-free Bio-mass Hydrolysates," Bioresource Technol., 245, 116-122(2017). https://doi.org/10.1016/j.biortech.2017.08.206
  8. Lee, S. C., "Separation of Acetic Acid from Simulated Biomass Hydrolysates Containing Furans by Emulsion Liquid Membranes with An Organophosphorous Extractant," Korean Chem. Eng. Res., 56(5), 693-462(2018).
  9. Gomes, E. D. and Rodrigues, A. E., "Fractionation of Acids, Ketones and Aldehydes from Alkaline Lignin Oxidation Solution with SP700 Resin," Sep. Purif. Technol., 198, 256-264(2018). https://doi.org/10.1016/j.seppur.2017.11.050
  10. Maman, O., Marseille, F., Guillet, B., Disnar, J. and Morin, P., "Separation of Phenolic Aldehydes, Ketones and Acids from Lignin Degradation by Capillary Zone Electrophoresis," J. Chromatography A, 755, 89-97(1996). https://doi.org/10.1016/S0021-9673(96)00583-3
  11. Al-Mudhaf, H. F., Hegazi, M. F. and Abu-Shadi, A. I., "Partition Data of Acetic Acid Between Aqueous NaCl Solutions and Trioctylphosphine Oxide in Cyclohexane Diluent," Sep. Purif. Technol., 27, 41-50(2002). https://doi.org/10.1016/S1383-5866(01)00192-7
  12. Lee, S. C., "Application of Emulsion Liquid Membrane to Removal of Fermentation Inhibitors from Simulated Hemicellulosic Hydrolysates," Korean Chem. Eng. Res., 53(4), 457-462(2015) https://doi.org/10.9713/kcer.2015.53.4.457