Add time:09/26/2019         Source:infona.pl

The radical telomerisation of trifluoroethylene (TrFE) with dimethyl phosphite (DMP) was investigated to synthesize fluorinated monoadducts bearing a phosphonate end-group such as HTrFEP(O)(OCH₃)₂. Among various radical initiators, di-tert-butyl peroxide (DTBP) was the most efficient one at 80–140°C. This telomerisation protocol successfully yielded mainly the monoadduct of TrFE and DMP. A structural study of the TrFE-DMP monoadduct was carried out using ¹H, ¹³C, ¹⁹F and ³¹P NMR spectroscopies and showed that a mixture of dimethyl-1,2,2-trifluoroethylphosphonate and dimethyl-1,1,2-trifluoroethylphosphonate was obtained. The best experimental conditions to reach high yields of monoadduct were achieved at T=140°C, using initial molar ratios R₀=[DMP]₀/[TrFE]₀ and C₀=[DTBP]₀/[TrFE]₀ of 3 and 0.05, respectively, and a reaction time of 15h. Higher telomeric adducts were also detected by MALDI-TOF mass spectrometry.

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