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Synthesis of Fluorinated Dialkyl Carbonates from Carbon Dioxide as a Carbonyl Source
Author(s) -
Sugiyama Masafumi,
Akiyama Midori,
Nishiyama Kohei,
Okazoe Takashi,
Nozaki Kyoko
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202000090
Subject(s) - phosgene , carbonate , chemistry , carbon dioxide , nucleophile , diethyl carbonate , transesterification , yield (engineering) , organic chemistry , stoichiometry , diphenyl carbonate , dimethyl carbonate , inorganic chemistry , catalysis , materials science , ethylene carbonate , electrode , electrolyte , metallurgy
Fluorinated dialkyl carbonates (DACs), which serve as environmentally benign phosgene substitutes, were produced successfully from carbon dioxide either directly or indirectly. Nucleophilic addition of 2,2,2‐trifluoroethanol to carbon dioxide and subsequent reaction with 2,2,2‐trifluoroethyltriflate ( 3 a ) afforded bis(2,2,2‐trifluoroethyl) carbonate ( 1 ) in up to 79 % yield. Additionally, carbonate 1 was obtained through the stoichiometric reaction of 3 a and cesium carbonate. Although bis(1,1,1,3,3,3‐hexafluoro‐2‐propyl) carbonate ( 4 ) was difficult to obtain by either of the above two methods, it could be synthesized through the transesterification of carbonate 1 .