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Clean Synthesis of Epoxidized Tung Oil Derivatives via Phase Transfer Catalyst and Thiol–ene Reaction: A Detailed Study

Jia, Puyou, Ma, Yufeng, Xia, Haoyu, Zheng, Minrui, Feng, Guodong, Hu, Lihong, Zhang, Meng, Zhou, Yonghong
ACS sustainable chemistry & engineering 2018 v.6 no.11 pp. 13983-13994
catalysts, catalytic activity, epoxides, films (materials), human health, phthalates, plasticizers, pollution, pollution control, poly(vinyl chloride), raw materials, solvents, thermal stability, toxicity, tung oil
Introducing renewable tung oil into the environment-friendly plasticizer production via clean and efficient strategies to substitute toxic dioctyl phthalate (DOP) holds potential application value to reduce pollution and improve human health. Here we reported two strategies for production of epoxy plasticizers via phase transfer catalyst and thiol–ene reaction using tung oil as starting material. Phase transfer catalyst (C₁₇H₃₀ClN)₃O₄₀PW₁₂·xH₂O was synthesized and used in acid-free catalytic process. The optimum epoxidation reaction and thiol–ene reaction parameters were investigated. Epoxy value of the obtained epoxy tung oil methyl ester (ETM) and tung-oil-based epoxy plasticizer (TEP) reached 4.9% and 5.2%. Poly(vinyl chloride) (PVC) films plasticized with ETM and TEP showed better thermal stability and solvent resistance than DOP. Plasticizing efficiency of ETM and TEP reached 104.1% and 101.5%, respectively. In conclusion, epoxy plasticizers were produced in sustainable and environmentally friendly strategies using tung oil as raw material and can completely replace toxic DOP used in flexible PVC films.