폴리카보네이트 해중합을 이용한 Bisphenol A계 Bishydroxyethyl Ether 화합물 생성 특성

허미선; 김범식; 박유인; 한명완; Miseon Heo; Beomsik Kim; Youin Park; Myungwan Han

Korean Chemical Engineering Research, Vol.48, No.2, 164-171, April, 2010

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폴리카보네이트 해중합을 이용한 Bisphenol A계 Bishydroxyethyl Ether 화합물 생성 특성

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

허미선^{1, 2}, 김범식 ^{1, †}, 박유인 ¹, 한명완 ^{2, †}

¹한국화학연구원, 대전광역시 유성구 장동 100번지
²충남대학교 화학공학과, 대전광역시 유성구 궁동 220번지

Miseon Heo^{1, 2}, Beomsik Kim^{1, †}, Youin Park¹, and Myungwan Han^{2, †}

¹Korea Research Institute of Chemical Technology, 100 Jang-dong, Yuseong-gu, Daejeon 305-600, Korea
²Department of Chemical Engineering, Chungnam National University, 220 Gung-dong, Yuseong-gu, Daejeon 305-764, Korea

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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 ℃, 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 ℃, 10% catalyst/PC mole ratio, 20 mmol of EC. BHE-BPA purity of better than 99% was achieved by crystallization of BHE-BPA.

Keywords:PC(Polycarbonate);BHE-BPA(bishydroxyethyl ether of bisphenol A);EC(Ethylenecarbonate)

[References]

Fox DW, Peters EN, U.S. Patent No. 4,885,407 (1989)
Arai R, Zenda K, Kazuko KH, Toshitaka Y, Funaxuluri T, Chem. Eng. Sci.
Buysch HJ, Schoen N, Kuehling S, Verfahren ZS, “Polycarbonaten in Bisphenol und Diarylcarbonate,” Ger. Patent No. 4,220,412 (1994)
Shafer SJ, Park C, U.S. Patent No. 5,336,814 (1994)
Hu LC, Oku A, Yamada E, Polymer, 39(16), 3841 (1998)
Pinero R, Garcia J, Cocero MJ, GreenChem, 7, 380 (2005)
Pinero-Hernanz R, Garcia-Serna J, Cocero MJ, AIChE J., 52(12), 4186 (2006)
Kim D, Kim BK, Cho YM, Han M, Kim BS, Ind. Eng. Chem. Res., 48(2), 685 (2009)
Kim D, Kim BK, Cho Y, Han M, Kim BS, Ind. Eng. Chem. Res., 48(14), 6591 (2009)
Oku A, Tanaka S, Hata S, Polymer, 41(18), 6749 (2000)
Lin CH, Lin HY, Liao WZ, Shenghong A, Green. Chem, 9, 38 (2007)
Jang BN, Wilkie CA, Polym. Degrad. Stab, 86, 419 (2004)

[Related Articles]

[1] Fox DW, Peters EN, U.S. Patent No. 4,885,407 (1989)

[2] Arai R, Zenda K, Kazuko KH, Toshitaka Y, Funaxuluri T, Chem. Eng. Sci.

[3] Buysch HJ, Schoen N, Kuehling S, Verfahren ZS, “Polycarbonaten in Bisphenol und Diarylcarbonate,” Ger. Patent No. 4,220,412 (1994)

[4] Shafer SJ, Park C, U.S. Patent No. 5,336,814 (1994)

[5] Hu LC, Oku A, Yamada E, Polymer, 39(16), 3841 (1998)

[6] Pinero R, Garcia J, Cocero MJ, GreenChem, 7, 380 (2005)

[7] Pinero-Hernanz R, Garcia-Serna J, Cocero MJ, AIChE J., 52(12), 4186 (2006)

[8] Kim D, Kim BK, Cho YM, Han M, Kim BS, Ind. Eng. Chem. Res., 48(2), 685 (2009)

[9] Kim D, Kim BK, Cho Y, Han M, Kim BS, Ind. Eng. Chem. Res., 48(14), 6591 (2009)

[10] Oku A, Tanaka S, Hata S, Polymer, 41(18), 6749 (2000)

[11] Lin CH, Lin HY, Liao WZ, Shenghong A, Green. Chem, 9, 38 (2007)

[12] Jang BN, Wilkie CA, Polym. Degrad. Stab, 86, 419 (2004)