SCI和EI收录∣中国化工学会会刊

中国化学工程学报 ›› 2022, Vol. 44 ›› Issue (4): 41-50.DOI: 10.1016/j.cjche.2021.03.048

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Insights into biobased epoxidized fatty acid isobutyl esters from biodiesel: Preparation and application as plasticizer

Xiaojiang Liang1, Fengjiao Wu1, Qinglong Xie1, Zhenyu Wu1, Jinjin Cai1, Congwen Zheng1, Junhong Fu2, Yong Nie1   

  1. 1 Biodiesel Engineering Lab of China Petroleum & Chemical Industry Federation, and Zhejiang Province Key Lab of Biofuel, Zhejiang University of Technology, Hangzhou 310014, China;
    2 Zhejiang Jiaao Enprotech Stock Co., Ltd, Tongxiang 314000, China
  • 收稿日期:2020-12-02 修回日期:2021-03-25 出版日期:2022-04-28 发布日期:2022-06-18
  • 通讯作者: Yong Nie,E-mail:ny_zjut@zjut.edu.cn
  • 基金资助:
    Financial support provided by the National High-tech Research and Development Program of China (2014AA022103) is greatly acknowledged.

Insights into biobased epoxidized fatty acid isobutyl esters from biodiesel: Preparation and application as plasticizer

Xiaojiang Liang1, Fengjiao Wu1, Qinglong Xie1, Zhenyu Wu1, Jinjin Cai1, Congwen Zheng1, Junhong Fu2, Yong Nie1   

  1. 1 Biodiesel Engineering Lab of China Petroleum & Chemical Industry Federation, and Zhejiang Province Key Lab of Biofuel, Zhejiang University of Technology, Hangzhou 310014, China;
    2 Zhejiang Jiaao Enprotech Stock Co., Ltd, Tongxiang 314000, China
  • Received:2020-12-02 Revised:2021-03-25 Online:2022-04-28 Published:2022-06-18
  • Contact: Yong Nie,E-mail:ny_zjut@zjut.edu.cn
  • Supported by:
    Financial support provided by the National High-tech Research and Development Program of China (2014AA022103) is greatly acknowledged.

摘要: Biodiesel was used to prepare epoxidized fatty acid isobutyl esters (Ep-FABEs) as a biobased plasticizer in this work. Transesterification of biodiesel with isobutanol catalyzed by tetrabutyl titanate was carried out in a gas-liquid tower reactor. The conversion achieved nearly 100% within 5 h under the reaction temperature, the mass ratio of catalyst to fatty acid methyl esters (FAMEs), and isobutanol to FAMEs total molar ratio of 180 ℃, 0.4 %(mass), and 5.4:1, respectively. In addition, kinetic model of the transesterification reaction was developed at 150–190 ℃. The calculated activation energy was 48.93 kJ·mol-1. Then, the epoxidation of obtained fatty acid isobutyl esters (FABEs) was conducted in the presence of formic acid and hydrogen peroxide. The Ep-FABEs was further analyzed for its plasticizing effectiveness to replace dioctyl phthalate (DOP) and compared with conventional epoxy plasticizer epoxidized fatty acid methyl esters (Ep-FAMEs). The results indicated that the thermal stability and mechanical properties of PVC films with Ep-FABEs plasticizer were significantly improved compared with those plasticized with DOP. In addition, the extraction resistance and migration stability of Ep-FABEs were better than those of Ep-FAMEs. Overall, the prepared Ep-FABEs via structural modification of biodiesel proved to be a promising biobased plasticizer.

关键词: Biodiesel, Transesterification, Isobutyl esters, Epoxidized isobutyl esters, Biobased plasticizer

Abstract: Biodiesel was used to prepare epoxidized fatty acid isobutyl esters (Ep-FABEs) as a biobased plasticizer in this work. Transesterification of biodiesel with isobutanol catalyzed by tetrabutyl titanate was carried out in a gas-liquid tower reactor. The conversion achieved nearly 100% within 5 h under the reaction temperature, the mass ratio of catalyst to fatty acid methyl esters (FAMEs), and isobutanol to FAMEs total molar ratio of 180 ℃, 0.4 %(mass), and 5.4:1, respectively. In addition, kinetic model of the transesterification reaction was developed at 150–190 ℃. The calculated activation energy was 48.93 kJ·mol-1. Then, the epoxidation of obtained fatty acid isobutyl esters (FABEs) was conducted in the presence of formic acid and hydrogen peroxide. The Ep-FABEs was further analyzed for its plasticizing effectiveness to replace dioctyl phthalate (DOP) and compared with conventional epoxy plasticizer epoxidized fatty acid methyl esters (Ep-FAMEs). The results indicated that the thermal stability and mechanical properties of PVC films with Ep-FABEs plasticizer were significantly improved compared with those plasticized with DOP. In addition, the extraction resistance and migration stability of Ep-FABEs were better than those of Ep-FAMEs. Overall, the prepared Ep-FABEs via structural modification of biodiesel proved to be a promising biobased plasticizer.

Key words: Biodiesel, Transesterification, Isobutyl esters, Epoxidized isobutyl esters, Biobased plasticizer