382-28-5Relevant articles and documents
ELECTROCHEMICAL PRODUCTION OF PARTIALLY FLUORINATED ORGANIC COMPOUNDS: N-METHYLMORPHOLINE FLUORINATION
Gambaretto, G. P.,Napoli, M.,Fraccaro, C.,Conte, L.
, p. 427 - 436 (1982)
The usual electrochemical fluorination of organic compounds in anhydrous HF produces completely fluorinated materials.In order to obtain partially fluorinated compounds, electrofluorination has been conducted under various conditions, including the use of solvents.None of the solvents lead to satisfactory results.Experiments have also been carried out with high concentrations of N-methylmorpholine in anhydrous HF and they have provided information about the selectivity and the mechanism of the reaction.Various partially fluorinated derivatives of N-methylmorpholine have been identified, and some of them separated from the reaction mixture.
Electrochemical fluorination: State of the art and future tendences
Conte, Lino,Gambaretto, Gian Paolo
, p. 139 - 144 (2004)
A brief survey of the ECF process for the preparation of perfluorinated organo-compounds is given. The yield of perfluorinated products depends on the experimental conditions and on the nature of the starting material. Some useful rules are reported in order to optimise the ECF process. An improved operational technique allowed to obtain high yield of perfluorodimorpholinepropane (PFDMP) by simultaneous fluorination of dimorpholinepropane and N -methylmorpholine.
Electrochemical fluorination of di- and tri-(2-hydroxyethyl)-substituted alkylamines
Abe, Takashi,Soloshonok, Irina,Baba, Hajime,Sekiya, Akira
, p. 51 - 57 (2007/10/03)
Several 2-(hydroxyethyl)-substituted alkylamines like 1,4-bis(2-hydroxyethyl)piperazine, N,N-bis(2-hydroxyethyl)methylamine, N,N-bis(2-hydroxyethyl)ethylamine, and N,N,N-tris(2-hydroxyethyl)amine as well as their derivatives (HCl salts, a borate and trimethylsilylethers) were subjected to electrochemical fluorination. From 1,4-bis(2-hydroxyethyl)piperazine, F-[1,4-bis(fluorocarbonylmethyl)piperazine] was obtained in low yield. In the fluorination of N,N-bis(2-hydroxyethyl)alkylamines and N,N,N-tris(2-hydroxyethyl)amine, cyclization occurred extensively, affording large quantities of F-morpholine derivatives. However, F-N,N-bis(fluorocarbonylmethyl)methylamine was obtained from the former in low, isolated yield.
The electrochemical fluorination of N-containing carboxylic acids (Part 4). Fluorination of methyl 3-dialkylamino-isobutyrates and methyl 3-dialkylamino-n-butyrates
Abe, Takashi,Fukaya, Haruhiko,Hayashi, Eiji,Hayakawa, Yoshio,Nishida, Masakazu,Baba, Hajime
, p. 193 - 202 (2007/10/02)
Several methyl esters of 3-dialkylamino-substituted n- and isobutyric acids have been subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides.Dimethyl, diethyl, pyrrolidino, morpholino, piperidino and N-methylpiperazino groups were investigated as dialkylamino substituents.The structure/yield relationship was evaluated both in terms of the structure of the acid and the kind of amino group, respectively.Better yields of perfluoroacid fluorides were obtained from methyl esters having isobutyric acid skeletons than those having n-butyric acid groups, and from the acids containing cyclic amino groups than those containing acyclic ones.
