335-35-3Relevant academic research and scientific papers
ELECTROCHEMICAL FLUORINATION OF 4-(PERFLUORO-n-BUTYL)-n-BUTANOYL CHLORIDE
Napoli, M.,Conte, L.,Gambaretto, G. P.,Carlini, F. M.
, p. 213 - 224 (2007/10/02)
Electrochemical fluorination of 4-(perfluoro-n-butyl)-n-butanoyl chloride produces perfluorooctanoyl fluoride in higher yields than those obtained from n-octanoyl chloride, which is the usual starting material.In particular, one of the by-products of the industrial process, the cyclic perfluoroether perfluoro-2-propyl-tetrahydropyran, is not formed.Also the other by-products, except fluorocarbon perfluoro-n-heptane, are produced in lower amounts.These results are discussed and a mechanism is suggested.
ANALYSIS OF THE PRODUCTS FROM THE ELECTROCHEMICAL FLUORINATION OF OCTANOYL CHLORIDE
Prokop, H.W.,Zhou, H-J,Xu, S-Q,Wu, C-H,Liu, C. C.
, p. 277 - 290 (2007/10/02)
The perfluorinated products from the electrochemical fluorination of octanoyl chloride were analyzed using several techniques.Cappillary gas chromatography was used for quantitative analysis of the desired product, perfluorooctanoyl fluoride, and for perfluorinated cyclic ether by-products.Isopropyl ether was an effective solvent, and ethylbenzene served as an internal standard.Acidimetric titration was used to qualify the amount of acid derivative products present in the sample.Since the products have limited solubility in water, alternative solvents were developed.Taking advantage of the facile hydrolysis of the acyl fluoride product, the perfluorinated acid was isolated.Details of the application of these chemical techniques to perfluorinated products and the corresponding results will be discussed.
ELECTROCHEMICAL FLUORINATION USING POROUS NICKEL AND FOAM NICKEL ANODES
Drakesmith, F. G.,Hughes, D. A.
, p. 103 - 134 (2007/10/02)
This work set out to examine the reasons behind some of the problems associated with ECF, namely, lack of reproducibility, low chemical yields, poor selectivity and low current densities, with a view to ameliorating these shortcomings and making the process more attractive to the chemical industry.The approach was to study the chemistry under controlled conditions of potential, reactant concentration, temperature, etc., and to analyse the results in terms of product structure, distribution and yield.Two distinct stages in the process were identified, i) the conditioning of the electrode, and, ii) the fluorination of the organic substrate.These stages are described in detail in relation to two model systems investigated, the fluorination of propene using porous and foam nickel anodes, and the fluorination of the octanoyl chloride using nickel foam anodes.The scales of experiments ranged from 100 ml to 100 l cell capacities.General conclusions are derived and recommendations made for the more efficient operation of the process.
FREE RADICAL CHEMISTRY, PART 5. A NEW APPROACH TO THE SYNTHESIS OF PERFLUORINATED ETHERS
Chambers, Richard D.,Grievson, Brian,Drakesmith, Frederick G.,Powell, Richard L.
, p. 323 - 340 (2007/10/02)
Fluorinations of the free-radical adducts of fluorinated alkenes, to ethers, over cobalt trifluoride are described and perfluorinated ethers are obtained at temperatures in excess of 400 deg C.The effect of structure on the formation of perfluoroethers is outlined.
FLUORINATION OF 2-ALKYL-SUBSTITUTED OXIRANES. THE SYNTHESIS AND PURIFICATION OF PERFLUORO(2-ALKYL-SUBSTITUTED OXANE)S
Abe, Takashi,Hayashi, Eiji,Baba, Hajime,Kodaira, Kazuo,Nagase, Shunji
, p. 353 - 380 (2007/10/02)
Five kinds of 2-alkyl-substituted oxanes like 2-ethyloxane, 2-n-propyloxane, 2-iso-propyloxane, 2-n-butyloxane and 2-n-amyloxane were fluorinated electrochemically to give the corresponding perfluoro(2-alkyloxane)s.The perfluoro(2-alkyloxane)s were obtained in good yields from these starting materials together with isomeric perfluoro(2-alkyloxolane)s, perfluoro(2-alkyl-5-methyloxolane)s and perfluoro(dialkyl ether)s.The purification of the perfluoro(2-alkyloxane)s which contained small amounts of isomeric perfluoro(2-alkyloxolane)s was succesfully achieved by recovering the former unreacted after treating these mixtures with anhydrous aluminum chloride at 150-160 deg C during ca. 48 hrs in order to convert the latter into the easy-separable perfluoro-(2,5,5-trichloro-2-alkyloxolane)s.Small quantities of new perfluoro(5,5-dichloroalkanoyl chloride)s were also among the chlorination products.The spectroscopic data as well as the physical properties of these new fluorination products, and perfluoro(2,5,5-trichloro-2-alkyloxolane)s and perfluoro(5,5-dichloroalkanoyl chloride)s are presented.
