Electrochemical fluorination of dimethyl glutarate and its characterization

Abstract

Monofluoro dimethyl glutarate has been successfully synthesized for the first time by electrochemical fluorination. It is done in an undivided polypropylene cell with platinum electrodes. Initially at three different current densities, dimethyl glutarate is subjected to electrofluorination. Maximum yield of monofluoro product is obtained at 15 mA cm −2 . Selecting this current density, electrosynthesis is done at three different charges. Maximum yield of 71.5% of the monofluoro product is obtained with a conversion efficiency of 95.2% when the charge of 6 F/mol is passed. The synthesized product is characterized using Fourier transform infrared (FTIR), gas chromatography/mass spectrometry (GC/MS), and nuclear magnetic resonance (NMR). The product purity and composition are ascertained using GC/MS. The attachment of fluorine to methylene group is indicated using FTIR data. From NMR studies, the environment of fluorine in the neighborhood of carbon and hydrogen has been established. Results are discussed in the paper.

Voltammetric behavior of triethylamine trihydrofluoride and anisole in acetonitrile as a first approach of studies for electro-fluorination of some adducts

“…Using the maximum current as an approximation for the expected limiting current (Fig. 11(b)), and applying the Levich relation (10), a non-linear correlation of I lim = f(ω 1/2 ) is obtained within the ω examined range (Fig. 12(a)), in accordance with the previous passivation explanations.…”

“…Chemical fluorination of various molecules involves multi-step reaction process, using gaseous fluorine ("Shiemann and Halex" in the industrial scale, toluene fluorination). For reducing the risks, several electrochemical studies [1][2][3][4][5][6][7][8][9][10][11][12] were carried out, on the anodic fluorination. General conclusions of these works, expressed in terms of fluorination yield, selectivity, number and position in the final product of fluoride atoms, shown the difficulty to fluorinate alkylated groups in alpha position of a hetero-atom, and inform on the optimal conditions (electrolyte nature, solvents, electrode material and electric energy to provide), to choose.…”

“…Et 3 N•4HF and fluorohydric acid, even if very corrosive, were also used as fluorinating agents by Ilayaraja et al [9,10]; for dimethyl glutarate fluorination, monofluoro dimethyl-glutarate were obtained with a 71% yield for a 6F/mol charge.…”

Review—Electrochemical Strategies for Selective Fluorination of Organic Compounds

“…The solvent free reaction avoids the use of any organic solvents (Scheme 18). 93 The maximum yield of monofluorinated product at the methylene position is obtained at 15 mA cm −2 . This can be accounted on the basis of EC B EC N mechanism.…”

Characterization of Polyester Coatings Intended for Food Contact by Different Analytical Techniques and Migration Testing by LC-MSn

“…Dimethyl glutarate, identified in sample CM1 and CM2, is a dicarboxylic acid ester used in paints, enamel, varnish, lacquer, thinner, paint stripper, remover, polyamide, polyester, resins, and plasticizers [20].…”