Korean Chemical Engineering Research

  • 제48권2호
  • /
  • Pages.164-171
  • /
  • 2010
  • /
  • 0304-128X(pISSN)
  • /
  • 2233-9558(eISSN)
한국화학공학회 (The Korean Institute of Chemical Engineers)
권호 표지

폴리카보네이트 해중합을 이용한 Bisphenol A계 Bishydroxyethyl Ether 화합물 생성 특성

Synthesis of Bishydroxyethyl Ether of Bisphenol A(BHE-BPA) Through the Depolymerization of Polycarbonate

  • Heo, Miseon (Korea Research Institute of Chemical Technology) ;
  • Kim, Beomsik (Korea Research Institute of Chemical Technology) ;
  • Park, Youin (Korea Research Institute of Chemical Technology) ;
  • Han, Myungwan (Department of Chemical Engineering, Chungnam National University)
  • 투고 : 2009.11.06
  • 심사 : 2009.12.03
  • 발행 : 2010.04.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

최근 폴리카보네이트의 수요가 증가에 따라 폴리카보네이트의 폐기물이 많이 발생하고 있다. 폐 폴리카보네이트를 재활용하여 새로운 소재 원료로 주목을 받고 있는 diol 형태의 bisphenol A계 bishydroxyethyl ether(BHE-BPA)를 얻고자 하였다. 이 물질은 폴리카보네이트계 폴리우레탄 합성에 좋은 소재로 사용될 수 있다. 본 연구에서는 에틸렌글리콜과 수산화나트륨(NaOH)을 각각 용매와 촉매로 사용하였고, 분해반응 생성물 중 하나인 에틸렌카보네이트(Ethylenecarbonate, EC)를 첨가하여 생성물의 전환율을 조사하였다. 알칼리촉매 사용에 따라 단순 글리콜리시스 반응에서 관찰되지 않았던 ether 화합물들이 합성되었으며 온도 $220^{\circ}C$, 10% 촉매/PC 몰비, EC 20 mmol 조건에서 폴리카보네이트로부터 수율 92% 이상의 BHE-BPA를 얻었고 재결정을 통하여 99% 이상의 순도를 얻는 것이 가능하였다.

Recently, the waste of Polycarbonate(PC) is increase with the increase in demand of a polycarbonate. It is concerned with producing a new material and diol monomer, bishydroxyethyl ether of bisphenol A(BHE-BPA) through depolymerization of the polycarbonate waste at recycling. BHE-BPA can be used as a good raw material for the synthesis of polycarbonate type polyurethane. PC particles were depolymerized with base-catalyst NaOH, solvent EG, and ethylene carbonate(EC) was formed during the PC depolymerziation. EC was added to promote the conversion from bispenol-A to BHE-BPA. The characteristics of depolymeraion of polycarbonate as well as conversion of bispenol-A to BHE-BPA were investigated. BHE-BPA yield of 92% was obtained at temperature $220^{\circ}C$, 10% catalyst/PC mole ratio, 20 mmol of EC. BHE-BPA purity of better than 99% was achieved by crystallization of BHE-BPA.

키워드

참고문헌

  1. Fox, D. W. and Peters, E. N., "Method for Recovering a Dihydric Phenol from a Scrap Polyester," U.S. Patent No. 4,885,407 (1989).
  2. Arai, R., Zenda, K., Kazuko, K. H., Toshitaka, Y. and Funaxuluri, T., "Reaction Kinetics of Hydrothermal Depolymerization of Poly(ethylene naphthalate), Poly(ethylene terephthalate), and Polycarbonate with Aqueous Ammonia Solution," Chem. Eng. Sci.
  3. Buysch, H. J., Schoen, N., Kuehling, S. and Verfahren, Z. S., "Polycarbonaten in Bisphenol und Diarylcarbonate," Ger. Patent No. 4,220,412(1994).
  4. Shafer, S. J. and Park, C., "Method for Recovering Bis Hydroxy Aromatic Organic Values and Bis Aryl Carbonate Values from Scrap Aromatic Polycarbonate," U.S. Patent No. 5,336,814(1994).
  5. Hu, L. C., Oku, A. and Yamada, E., "Alkali-catalyzed Methanolysis of Polycarbonate. A Study on Recycling of Bisphenol A and Dimethyl Carbonate," Polymer, 39, 3841-3845(1998). https://doi.org/10.1016/S0032-3861(97)10298-1
  6. Pinero, R., Garcia, J. and Cocero, M. J., "Chemical Recycling of Polycarbonate in a Semi-continuous Lab-plant. A Green Route with Methanol and Methanol-water Mixtures," GreenChem, 7, 380-387 (2005).
  7. Pinero, R., Garcia, J. and Cocero, M. J., "Nonstationary Model of the Semicontinuous Depolymerization of Polycarbonate," AIChE J, 52, 4186-4199(2006). https://doi.org/10.1002/aic.11025
  8. Kim, D. P., Kim, B. K., Cho, Y. M., Han, M. W. and Kim, B. S., "Kinetics of Polycarbonate Glycolysis in Ethylene Glycol," Ind. Eng. Chem. Res, 48, 685-691(2009). https://doi.org/10.1021/ie8010947
  9. Kim, D. P., Kim, B. K., Cho, Y. M., Han, M. W. and Kim, B. S., "Kinetics of Polycarbonate Methanolysis by a Consecutive Reaction Model," Ind. Eng. Chem. Res, 48, 6591-6599(2009). https://doi.org/10.1021/ie801893v
  10. Oku, A., Tanaka, S. and Hata, S., "Chemical Conversion of Polycarbonate to Bishydroxyethyl Ether of Bisphenol A. An Approach to the Chemical Recycling of Plastic Wastes as Monomers," Polymer, 41, 6749-6753(2000). https://doi.org/10.1016/S0032-3861(00)00014-8
  11. Lin, C. H., Lin, H. Y., Liao, W. Z. and Shenghong, A., "Novel Chemical Recycling of Polycarbonate(PC) Waste into Bis-hydroxyalkyl Ethers of Bisphenol A for Use as PU Raw Materials," Green. Chem, 9, 38-43(2007). https://doi.org/10.1039/b609638g
  12. Jang, B. N. and Wilkie, C. A., "A TGA/FTIR and Mass Spectral Study on the Thermal Degradation of Bisphenol A Polycarbonate," Polym. Degrad. Stab, 86, 419-430(2004). https://doi.org/10.1016/j.polymdegradstab.2004.05.009