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Efficient synthesis of epoxybutane from butanediol via a two-step process
Niu, X; Wang, LG; Cao, JY; Cao, Y; He, P; Zhou, JY; Li, HQ; Niu, Xin; Wang, Liguo; Cao, Junya; Cao, Yan; He, Peng; Zhou, Junya; Li, Huiquan
2019
Source PublicationRSC ADVANCES
ISSN2046-2069
Volume9Issue:18Pages:10072
AbstractA novel approach for the synthesis of epoxybutane via decarboxylation of butenyl carbonate derived from butanediol was developed for the first time. For the carbonylation of butanediol with dimethyl carbonate, NaAlO2 has exhibited excellent catalytic activity under mild reaction conditions. The yield of butenyl carbonate reached as high as 96.2%. NaAlO2 provides suitable acid-base active sites to promote the transesterification reaction of butanediol and dimethyl carbonate. For the following step of decarboxylation of butenyl carbonate, ionic liquid 1-butyl-3-methylimidazolium bromide could effectively catalyze the decarboxylation process both in batch or continuous processes. Moreover, the catalytic mechanism for the crucial step of decarboxylation of butenyl carbonate over 1-butyl-3-methylimidazolium bromide was explored using DFT calculations. The results showed that the electrostatic and hydrogen-bond effects of 1-butyl-3-methylimidazolium bromide played a crucial role for the generation of epoxybutane. Briefly, the Br anion of the ionic liquid attacks the methylene of the ring and the H of the ionic liquid cation attacks the carbonyl oxygen, which facilitated the five-ring opening and subsequent decarboxylation to form BO. This study not only provided a new and green synthetic route for producing epoxybutane, but also contributed to the effective utilization of butanediol, which is inevitably produced as by-product in the process of coal to ethylene glycol, suggesting a promising application in the clean manufacture of epoxybutane with inexpensive cost.
KeywordRING-OPENING POLYMERIZATION GLYCEROL CARBONATE IONIC-LIQUID CYCLIC CARBONATES GREENER SYNTHESIS PROPYLENE-OXIDE CATALYST DIOXIDE CO2 CONVERSION
SubtypeArticle
DOI10.1039/c9ra01220f
WOS IDWOS:000466754600022
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/28359
Collection中国科学院过程工程研究所
Recommended Citation
GB/T 7714
Niu, X,Wang, LG,Cao, JY,et al. Efficient synthesis of epoxybutane from butanediol via a two-step process[J]. RSC ADVANCES,2019,9(18):10072, 10080.
APA Niu, X.,Wang, LG.,Cao, JY.,Cao, Y.,He, P.,...&Li, Huiquan.(2019).Efficient synthesis of epoxybutane from butanediol via a two-step process.RSC ADVANCES,9(18),10072.
MLA Niu, X,et al."Efficient synthesis of epoxybutane from butanediol via a two-step process".RSC ADVANCES 9.18(2019):10072.
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