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Upgrading of poly(vinyl chloride) by chemical modifications using sodium sulfide

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Abstract

The recycling of poly(vinyl chloride) (PVC) is one of the most important issues in the treatment of waste plastics. To improve PVC recycling, it is necessary to develop new recycling techniques, including new techniques for the dechlorination of chlorine-containing polymers. It has been established that wet dechlorination of PVC in NaOH/ethylene glycol solution is more effective than dry dechlorination. In this study, the wet process was used, and the chemical modification of PVC by nucleophilic substitution was considered for upgrading waste PVC. Chlorine was substituted in solution by several nucleophilic reagents, thus changing the properties of PVC. The reaction of PVC in Na2S/ethylene glycol solution at 170°C resulted in the formation of a mixture comprising 32% elimination and 26% substitution products. The scanning electron microscopy/energy dispersive X-ray spectroscopy mappings and elementary analysis of PVC indicated that this chlorine-substitution process led to cross-linking by sulfur.

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References

  1. Yoshioka T, Akama T, Uchida M, Okuwaki A (2000) Analysis of two-stage dehydrochlorination of poly(vinyl chloride) using TG-MS. Chem Lett 29:322–323

    Article  Google Scholar 

  2. Yoshioka T, Saitoh N, Okuwaki A (2005) Temperature dependence on the activation energy of dechlorination in thermal degradation of polyvinyl chloride. Chem Lett 34:70–71

    Article  CAS  Google Scholar 

  3. Bhaskar T, Sakata Y (2006) Liquefaction of PVC Mixed Plastics In: Scheirs J, Kaminsky W (eds) Feedstock recycling and pyrolysis of waste plastics. Wiley, London, 498–502

    Google Scholar 

  4. Montaudo G, Puglisi C (1991) Evolution of aromatics in the thermal degradation of poly(vinyl chloride): a mechanistic study. Polym Degrad Stab 33:229–262

    Article  CAS  Google Scholar 

  5. Mio H, Saeki S, Kano J, Saito F (2002) Estimation of mechanochemical dechlorination rate of poly(vinyl chloride). Environ Sci Technol 36:1344–1348

    Article  CAS  Google Scholar 

  6. Winkler DE (1959) Mechanism of poly(vinyl chloride) degradation and stabilization. J Polym Sci 35:3–16

    Article  CAS  Google Scholar 

  7. Behnisch J, Zimmermann H (1992) Kinetics and mechanism of the polyene formation during dehydrochlorination of poly(vinyl chloride) in the solid state. Int J Polym Mater 16:143–157

    Article  CAS  Google Scholar 

  8. Yoshinaga T, Yamaye M, Kito T, Ichiki T, Ogata M, Chen J, Fujino H, Tanimura T, Yamanobe T (2004) Alkaline dechlorination of poly(vinyl chloride) in organic solvents under mild conditions. Polym Degrad Stab 86:541–547

    Article  CAS  Google Scholar 

  9. Kise H (1982) Dehydrochlorination of poly(vinyl chloride) by aqueous sodium hydroxide solution under two-phase conditions. J Polym Sci 20:3189–3197

    CAS  Google Scholar 

  10. Guo L, Shi G, Liang Y (2001) Poly(ethylene glycol)s catalyzed homogeneous dehydrochlorination of poly(vinyl chloride) with potassium hydroxide. Polymer 42:5581–5587

    Article  CAS  Google Scholar 

  11. Shin S-M, Yoshioka T, Okuwaki A (1998) Dehydrochlorination behavior of flexible PVC pellets in NaOH solutions at elevated temperature. J Appl Polym Sci 67:2171–2177

    Article  CAS  Google Scholar 

  12. Yoshioka T, Furukawa K, Sato T, Okuwaki A (1998) Chemical recycling of flexible PVC by oxygen oxidation in NaOH solutions at elevated temperatures. J Appl Polym Sci 70:129–135

    Article  CAS  Google Scholar 

  13. Shin S-M, Yoshioka T, Okuwaki A (1998) Dehydrochlorination behavior of rigid PVC pellet in NaOH solutions at elevated temperature. Polym Degrad Stab 61:349–353

    Article  CAS  Google Scholar 

  14. Yoshioka T, Furukawa K, Okuwaki A (2000) Chemical recycling of rigid PVC by oxygen oxidation in NaOH solutions at elevated temperatures. Polym Degrad Stab 67:285–290

    Article  CAS  Google Scholar 

  15. Yoshioka T, Kameda T, Imai S, Okuwaki A (2008) Dechlorination of poly(vinyl chloride) using NaOH in ethylene glycol under atmospheric pressure. Polym Degrad Stab 93:1138–1141

    Article  CAS  Google Scholar 

  16. Sacristan J, Reinecke H, Mijangos C (2000) Surface modification of PVC films in solvent-nonsolvent mixtures. Polymer 41: 5577–5582

    Article  CAS  Google Scholar 

  17. Herrero M, Tiemblo P, Reyes-Labarta J, Mijangos C, Reinecke H (2002) PVC modification with new functional groups. Influence of hydrogen bonds on reactivity, stiffness and specific volume. Polymer 43:2631–2636

    Article  CAS  Google Scholar 

  18. James NR, Jayakrishnan A (2003) Surface thiocyanation of plasticized poly(vinyl chloride) and its effect on bacterial adhesion. Biomater 24:2205–2212

    Article  CAS  Google Scholar 

  19. Bicak N, Sherrington DC, Bulbul H (2001) Vinylamine polymer via chemical modification of PVC. Eur Polym J 37:801–805

    Article  CAS  Google Scholar 

  20. Moulay S, Zeffouni Z (2006) Application of the Conant-Finkelstein reaction to the modification of PVC: iodinated PVC. J Polym Res 13:267–275

    Article  CAS  Google Scholar 

  21. Kameda T, Ono M, Grause G, Mizoguchi T, Yoshioka T (2009) Chemical modification of poly(vinyl chloride) by nucleophilic substitution. Polym Degrad Stab 94:107–112

    Article  CAS  Google Scholar 

  22. Kameda T, Imai K, Grause G, Mizoguchi T, Yoshioka T (2009) Kinetics of the dehydrochlorination of poly(vinyl chloride) in the presence of NaOH and various diols as solvents. Polym Degrad Stab 94:1595–1597

    Article  CAS  Google Scholar 

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Correspondence to Toshiaki Yoshioka.

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Yoshihara, M., Grause, G., Kameda, T. et al. Upgrading of poly(vinyl chloride) by chemical modifications using sodium sulfide. J Mater Cycles Waste Manag 12, 264–270 (2010). https://doi.org/10.1007/s10163-010-0275-z

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  • DOI: https://doi.org/10.1007/s10163-010-0275-z

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