Depolymerization of Poly(2,6-dimethyl-1,4-phenylene oxide) in Green Solvents: Water and Ionic Liquid
Sepa Nanayakkara A , Antonio F. Patti A and Kei Saito A BA School of Chemistry and Centre for Green Chemistry, Monash University, Clayton, Vic. 3800, Australia.
B Corresponding author. Email: Kei.Saito@monash.edu
Australian Journal of Chemistry 66(1) 60-66 https://doi.org/10.1071/CH12191
Submitted: 11 April 2012 Accepted: 24 August 2012 Published: 4 October 2012
Abstract
The depolymerization of poly(2,6-dimethyl-1,4-phenyleneoxide) (PPO) was accomplished by employing 4-tert-butyl-2,6-dimethylphenol (TBDMP) and 2,6-dimethylphenol (DMP) under oxidative conditions in green solvents: water and ionic liquid. PPO depolymerized to oligomeric products in a faster process within 5 min with TBDMP and within 1 min with DMP in water. In addition to water, an ionic liquid mixture containing the 1-ethyl-3-methylimidazolium cation [C2mim] and a mixture of alkylbenzenesulfonate with xylene sulfonate anion [ABS] was used for the depolymerization of PPO. Depolymerization was successfully achieved in [C2mim][ABS] with TBDMP in a slower process within 3 h.
References
[1] P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, 1998, pp. 94–119 (Oxford University Press: London).[2] C. C. Price, Acc. Chem. Res. 1974, 7, 294.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXlsFalt7g%3D&md5=8c826d3b5705fd5ccfa49c23fa575567CAS |
[3] A. S. Hay, J. Polym. Sci., Polym. Phys. Ed. 1962, 58, 581.
| 1:CAS:528:DyaF38XktlShuro%3D&md5=5eabe4b63c51d7874b49920addaf97d1CAS |
[4] A. S. Hay, J. Polym. Sci. Pol. Chem. 1998, 36, 505.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXptVOrug%3D%3D&md5=24da1a6934b29795e94ed97ee9bef8aaCAS |
[5] A. S. Hay, H. S. Blanchard, G. F. Endres, J. W. Eustance, J. Am. Chem. Soc. 1959, 81, 6335.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3cXptFCksA%3D%3D&md5=5b3662059df065a22f802a0f6c0b72e0CAS |
[6] C. C. Price, N. S. Chu, J. Polym. Sci., Polym. Phys. Ed. 1962, 61, 135.
| 1:CAS:528:DyaF38Xks12qsb0%3D&md5=be1ed3a558d56bc7e536ec41781426ffCAS |
[7] H. Komoto, K. Ohmura, Makromol. Chem. 1973, 166, 57.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXktF2hsLY%3D&md5=73898ce0a64c2a08a4707c7bf5d2322fCAS |
[8] K. Saito, T. Tago, T. Masuyama, H. Nishide, Angew. Chem. Int. Ed. 2004, 43, 730.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhsVKqsLg%3D&md5=1675d4876a93bdba057282b06d3418a5CAS |
[9] E. Tsuchida, M. Kaneko, H. Nishide, Makromol. Chem. 1972, 151, 235.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38XhtFelurg%3D&md5=79b5b9c72ff0971f1fdff972a219bff8CAS |
[10] E. Tsuchida, M. Kaneko, H. Nishide, Makromol. Chem. 1972, 151, 221.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38XhtFelurs%3D&md5=bdb23ac88f7ece37d1fd84a0ceccf414CAS |
[11] K. Saito, N. Kuwashiro, H. Nishide, Polymer 2006, 47, 6581.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XoslGhsLw%3D&md5=43e4004b0c09dbf280f6c3260f559f0eCAS |
[12] M. Ionescu, A. B. Mihis, Macromol. Symp. 1997, 122, 249.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXmvVanur8%3D&md5=a9052e4c24f95358b681fd8e6810190fCAS |
[13] G. D. Cooper, Ann. N. Y. Acad. Sci. 1969, 159, 278.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXksFSmsbg%3D&md5=3ef700290b628ad4319e9d0f0c30547fCAS |
[14] G. D. Cooper, J. G. Bennett, J. Org. Chem. 1972, 37, 441.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38Xht1Oms74%3D&md5=32a0c99bb683f5be352b627f4d938522CAS |
[15] H. A. M. van Aert, M. H. P. van Genderen, G. J. M. L. van Steenpaal, L. Nelissen, E. W. Meijer, J. Liska, Macromolecules 1997, 30, 6056.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXmtVems70%3D&md5=4a4bd70d912f9b30e19f4cf106655fd9CAS |
[16] H. A. M. van Aert, M. E. M. Burkard, J. F. G. A. Jansen, M. H. P. van Gendersen, E. W. Meijer, H. Oevering, G. H. W. Buning, Macromolecules 1995, 28, 7967.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXos1yitrk%3D&md5=a75f7d96f0bf44a9a12fe5ecf727bc09CAS |
[17] K. Saito, T. Masuyama, K. Oyaizu, H. Nishide, Chem. – Eur. J. 2003, 9, 4240.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnsVSqsb8%3D&md5=13c5c4b89b49c0c10f014921d52ea6c5CAS |
[18] V. Percec, T. D. Shaffer, J. Polym. Sci. Pol. Lett. 1986, 24, 439.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XmtV2nu7k%3D&md5=16115ba0422b1de3a47edbce98c406c6CAS |
[19] V. Percec, J. H. Wang, Polym. Bull. 1990, 24, 71.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXksl2itbg%3D&md5=a78eb02838fc18f1e3b3ccf2579d2ef3CAS |
[20] J. H. Wang, V. Percec, Polym. Bull. 1991, 25, 33.
| 1:CAS:528:DyaK3MXhvVKitLc%3D&md5=af1ec6fec5af0064a495229a2cc15dceCAS |
[21] G. G. Haynes, A. H. Turner, W. A. Waters, J. Chem. Soc. 1956, 2823.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG2sXitFKntA%3D%3D&md5=d871f9f2e106230eb092d4cd8852c3d7CAS |
[22] G. D. Staffin, C. C. Price, J. Am. Chem. Soc. 1960, 82, 3632.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXlvFejsg%3D%3D&md5=9a71722b00f84c255fe84c32079d6c88CAS |
[23] I. Kilpeläinen, H. Xie, A. King, M. Granstrom, S. Heikkinen, D. S. Argyropoulos, J. Agric. Food Chem. 2007, 55, 9142.
| Crossref | GoogleScholarGoogle Scholar |
[24] S. S. Y. Tan, D. R. MacFarlane, J. Upfal, L. A. Edye, W. O. S. Doherty, A. F. Patti, J. M. Pringle, J. L. Scott, Green Chem. 2009, 11, 339.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXivVOltb8%3D&md5=b38806d1003f9b6f1c826d6c6eb11c5cCAS |
[25] Y. Pu, N. Jiang, A. J. Ragauskas, J. Wood Chem. Technol. 2007, 27, 23.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXkvFCltLw%3D&md5=6e040faff7f5093285a65bb1e661c9e3CAS |
[26] U. Svanholm, V. D. Parker, J. Chem. Soc., Perkin Trans. 1 1973, 1, 562.
| Crossref | GoogleScholarGoogle Scholar |
[27] G. A. Olah, Friedel-Crafts and Related Reactions 1963 (Wiley-Interscience: New York, NY).
[28] H. U. Moritz, Chem. Eng. Technol. 1989, 12, 71.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXlsFCgu7s%3D&md5=852029deb67d962b316d9bcc8b1b73feCAS |