TY - JOUR
T1 - Investigation on the preparation of 2,2-difluoroethylamine by amination of 1-halo-2,2-difluoroethane
AU - Han, Xue
AU - Qing, Feiyao
AU - Zhang, Chengping
AU - Jia, Xiaoqing
AU - Quan, Hengdao
N1 - Publisher Copyright:
© 2020
PY - 2021/2
Y1 - 2021/2
N2 - The synthesis of 2,2-difluoroethylamine via the amination of 1-halo-2,2-difluoroethane (halogen = Cl or Br) without catalyst and solvent was studied by experiment and theoretical calculation. In order to compare the difficulty in the amination of 1-halo-2,2-difluoroethane with NH3, experimental investigations were carried through changing reaction temperature, molar ratio and reaction time. And experimental evidence demonstrated that 1-chloro-2,2-difluoroethane was more prone to amination than 1-bromo-2,2-difluoroethane under the same conditions. In addition, the reaction mechanism was investigated, and the formation complexity evaluated. Calculation of the transition states and rate constants, and analysis of the frontier molecular orbitals, indicated that the reaction rate of the amination of 1-chloro-2,2-difluoroethane was higher than that of 1-bromo-2,2-difluoroethane, which was consistent with the results of the experiment.
AB - The synthesis of 2,2-difluoroethylamine via the amination of 1-halo-2,2-difluoroethane (halogen = Cl or Br) without catalyst and solvent was studied by experiment and theoretical calculation. In order to compare the difficulty in the amination of 1-halo-2,2-difluoroethane with NH3, experimental investigations were carried through changing reaction temperature, molar ratio and reaction time. And experimental evidence demonstrated that 1-chloro-2,2-difluoroethane was more prone to amination than 1-bromo-2,2-difluoroethane under the same conditions. In addition, the reaction mechanism was investigated, and the formation complexity evaluated. Calculation of the transition states and rate constants, and analysis of the frontier molecular orbitals, indicated that the reaction rate of the amination of 1-chloro-2,2-difluoroethane was higher than that of 1-bromo-2,2-difluoroethane, which was consistent with the results of the experiment.
KW - 1-Bromo-2,2-difluoroethane
KW - 1-Chloro-2,2-difluoroethane
KW - 2-Difluoroethylamine
KW - Density functional theory
KW - Kinetic modeling
UR - http://www.scopus.com/inward/record.url?scp=85098083344&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2020.109690
DO - 10.1016/j.jfluchem.2020.109690
M3 - Article
AN - SCOPUS:85098083344
SN - 0022-1139
VL - 242
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
M1 - 109690
ER -