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Selective cyclodimerization of epichlorohydrin to dioxane derivatives over MOFs

(2020) ARABIAN JOURNAL OF CHEMISTRY. 13(1). p.1088-1093
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Abstract
Glycerol can be converted to valuable products such as epichlorohydrin which is an important intermediate applied in various industries. For example, dioxane derivatives, which are important pharmaceuticals, can be obtained from epichlorohydrin. In the present study, ZIF-8, ZIF-67, MIL-100, and UiO-66 were applied for the direct cyclodimerization of epichlorohydrin. These MOFs were selected because they were already applied as active catalysts in ring opening of epoxides. Among them, ZIF-8 showed the highest activity and selectivity in the absence of any solvent or co-catalyst. Using ZIF-8 as a catalyst, the cyclodimer product (1,4-dioxane 2,5-bis-chloromethyl) was obtained in a yield of about 70% which was significantly superior to previous homo or heterogeneous catalysts for this reaction. Due to ZIF-8 structure and the proposed mechanism, the cyclodimerization reaction catalyzed either by the defects in the structure and/or on the surface. Furthermore, acidic-basic characteristics were also in play. The NH3 and CO2 temperature-programed desorption technique were utilized to identify the active sites and thereby reaction mechanism. Moreover, because of similar properties of ZIF-8 to zeolites, the activity of commercial ZSM-5 for the same reaction was also investigated in this work.
Keywords
MOFs, ZIF, Cyclodimerization, Oligomerization, Epichlorohydrin, Temperature program desorption (TPD), METAL-ORGANIC FRAMEWORKS, CO2, POLYMERIZATION, ZIF-8, OLIGOMERIZATION, CONVERSION

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MLA
Mousavi, Bibimaryam, et al. “Selective Cyclodimerization of Epichlorohydrin to Dioxane Derivatives over MOFs.” ARABIAN JOURNAL OF CHEMISTRY, vol. 13, no. 1, 2020, pp. 1088–93.
APA
Mousavi, B., Chaemchuen, S., Phatanasri, S., Chen, C., Zeng, C., Ganguly, R., … Verpoort, F. (2020). Selective cyclodimerization of epichlorohydrin to dioxane derivatives over MOFs. ARABIAN JOURNAL OF CHEMISTRY, 13(1), 1088–1093.
Chicago author-date
Mousavi, Bibimaryam, Somboon Chaemchuen, Suphot Phatanasri, Cheng Chen, Cheng Zeng, Rakesh Ganguly, Serge Zhuiykov, and Francis Verpoort. 2020. “Selective Cyclodimerization of Epichlorohydrin to Dioxane Derivatives over MOFs.” ARABIAN JOURNAL OF CHEMISTRY 13 (1): 1088–93.
Chicago author-date (all authors)
Mousavi, Bibimaryam, Somboon Chaemchuen, Suphot Phatanasri, Cheng Chen, Cheng Zeng, Rakesh Ganguly, Serge Zhuiykov, and Francis Verpoort. 2020. “Selective Cyclodimerization of Epichlorohydrin to Dioxane Derivatives over MOFs.” ARABIAN JOURNAL OF CHEMISTRY 13 (1): 1088–1093.
Vancouver
1.
Mousavi B, Chaemchuen S, Phatanasri S, Chen C, Zeng C, Ganguly R, et al. Selective cyclodimerization of epichlorohydrin to dioxane derivatives over MOFs. ARABIAN JOURNAL OF CHEMISTRY. 2020;13(1):1088–93.
IEEE
[1]
B. Mousavi et al., “Selective cyclodimerization of epichlorohydrin to dioxane derivatives over MOFs,” ARABIAN JOURNAL OF CHEMISTRY, vol. 13, no. 1, pp. 1088–1093, 2020.
@article{8646492,
  abstract     = {Glycerol can be converted to valuable products such as epichlorohydrin which is an important intermediate applied in various industries. For example, dioxane derivatives, which are important pharmaceuticals, can be obtained from epichlorohydrin. In the present study, ZIF-8, ZIF-67, MIL-100, and UiO-66 were applied for the direct cyclodimerization of epichlorohydrin. These MOFs were selected because they were already applied as active catalysts in ring opening of epoxides. Among them, ZIF-8 showed the highest activity and selectivity in the absence of any solvent or co-catalyst. Using ZIF-8 as a catalyst, the cyclodimer product (1,4-dioxane 2,5-bis-chloromethyl) was obtained in a yield of about 70% which was significantly superior to previous homo or heterogeneous catalysts for this reaction. Due to ZIF-8 structure and the proposed mechanism, the cyclodimerization reaction catalyzed either by the defects in the structure and/or on the surface. Furthermore, acidic-basic characteristics were also in play. The NH3 and CO2 temperature-programed desorption technique were utilized to identify the active sites and thereby reaction mechanism. Moreover, because of similar properties of ZIF-8 to zeolites, the activity of commercial ZSM-5 for the same reaction was also investigated in this work.},
  author       = {Mousavi, Bibimaryam and Chaemchuen, Somboon and Phatanasri, Suphot and Chen, Cheng and Zeng, Cheng and Ganguly, Rakesh and Zhuiykov, Serge and Verpoort, Francis},
  issn         = {1878-5352},
  journal      = {ARABIAN JOURNAL OF CHEMISTRY},
  keywords     = {MOFs,ZIF,Cyclodimerization,Oligomerization,Epichlorohydrin,Temperature program desorption (TPD),METAL-ORGANIC FRAMEWORKS,CO2,POLYMERIZATION,ZIF-8,OLIGOMERIZATION,CONVERSION},
  language     = {eng},
  number       = {1},
  pages        = {1088--1093},
  title        = {Selective cyclodimerization of epichlorohydrin to dioxane derivatives over MOFs},
  url          = {http://dx.doi.org/10.1016/j.arabjc.2017.09.011},
  volume       = {13},
  year         = {2020},
}

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