335-66-0

Usage

Uses

Used in Chemical Industry:
PFOA is used as a processing aid in the manufacturing of fluoropolymers, such as Teflon, due to its ability to improve the polymerization process and the quality of the final product.
Used in Consumer Products:
PFOA has been utilized in various consumer products, including non-stick cookware, stain-resistant fabrics, and water-repellent coatings, owing to its unique properties that enhance performance and durability.
However, due to the growing awareness of the environmental and health risks associated with PFOA, many countries and organizations have implemented measures to limit or ban its use in consumer products and industrial processes. This has led to the development of alternative substances and methods to replace PFOA in various applications while minimizing the potential adverse effects on human health and the environment.

InChI:InChI=1/C8F16O/c9-1(25)2(10,11)3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)24

Upstream product

• 592-94-9 octanoic acid fluoride 
• 335-95-5 sodium perfluorooctanoate 
• 111-64-8 n-octanoic acid chloride 
• 124778-16-1 4-(perfluoro-n-butyl)-n-butanoyl chloride 
• 64018-25-3 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanoyl chloride 
• 559-14-8 perfluorooct-1-ene 
• 307-35-7 perfluorooctyl sulfofluorure 
• 33496-48-9 pentadecafluorooctanoic anhydride 
• 335-67-1 Perfluorooctanoic acid 

Downstream Products

• 335-57-9 perfluoroheptane 
• 137521-66-5 1-Phenyl-2-[4-(1,1,2,2-tetrafluoro-2-heptadecafluorooctyloxy-ethyl)-phenyl]-ethane-1,2-dione 
• 134948-34-8 Sodium perfluorooctanoxyacetate 
• 134918-66-4 Potassium perfluorooctanoxyacetate 
• 307-62-0 perfluorotetradecane 
• 109384-71-6 1,2,3,4,5-Pentafluoro-6-pentadecafluoronon-1-ynyl-benzene 
• 2501-01-1 Perfluoro-5,6-dimethyl-4,7-dioxadecane 

Relevant academic research and scientific papers

PROCESS IMPROVEMENTS IN THE ELECTROCHEMICAL FLUORINATION OF OCTANOYL CHLORIDE

The electrochemical fluorination of octanoyl chloride to produce perfluorooctanoyl fluoride in anhydrous hydrogen fluoride was investigated.The study was carried out in a microprocessor-aided modified Simons reactor system using a Cu/CuF2 reference electrode.The formation of polymeric tar at the anode surface was limited by the addition of a mercaptan compound and by constant current density operation.Continuous operation was achieved through frequent additions of a solution of hydrogen fluoride and reactant.Conversion of reactant to perfluorinated products was improved to 80 percent with good selectivity.Experimetnal results of this investigation are presented and discussed.

EINSTUFIGE HERSTELLUNG HALOGENIERTER CARBONSAUREFLUORIDE AUS DEN FREIEN SAUREN

The reaction of per- or polyhalogenated carboxylic acids with trifluoromethyl or difluorochloromethyl substituted aromatics takes place in the presence of Lewis-acid-catalysts and forms the corresponding acid fluorides in good to very good yields.

A full-fluorine octanoyl fluorine preparation method (by machine translation)

The invention relates to a preparation method of the whole fluorine octanoyl fluorine, fluorine gas diluted by inert gas under low temperature conditions with the caprylyl chloride reaction to prepare the full fluorine octanoyl fluorine. The method of the invention through the inert gas dilution, reduce the reaction temperature, by adding the agitation or filler such as fluorine gas with the technical means caprylyl chloride reaction is more moderate, uniform, easy to control, and greatly improves the yield of the whole fluorine octanoyl fluorine, and prevents the use of the metal anode of the electrolytic cell, substantially eliminates the generation of solid waste material. Fluorine gas with the caprylyl chloride direct reaction can have to avoid the waste of energy, and improve the yield of the fluorine octanoyl fluorine, reduce long chain carbon atom chain reaction produces by-products such as low fluorine carbon, ensure the quality of the product fluorine octanoyl fluorine, perfluorooctanoic acid production enterprises for a significant meaning. (by machine translation)

PROCESSES FOR PRODUCTION OF FLUORINE-CONTAINING COMPOUNDS

This process for producing fluorine-containing compounds includes liquid-phase fluorination by introducing a raw material compound and fluorine gas into a solvent to replace hydrogen atoms in the raw material compound with fluorine atoms. More specifically, the process for producing fluorine-containing compounds includes (1) promoting fluorination by dissolving the raw material compound in anhydrous hydrofluoric acid and introducing into a liquid-phase fluorination solvent, or (2) promoting fluorination by dissolving the raw material compound in a perfluoro compound having a plurality of polar groups in a molecule thereof and introducing into a liquid-phase fluorination solvent. According to these processes, a fluorination reaction can be carried out at high yield and without containing hardly any isomers while using a hydrocarbon compound as is for the raw material.

A Lewis acid catalytic process for preparing fluorocarboxylic acid halides

Selected Group III and Group V Lewis acids were found to catalyze the isomerization and rearrangement of halosulfonyldifluoromethyl group (Rf-CF2SO2X, where X is either chlorine or fluorine) to form fluorocarboxylic acid halides (RfCOX). Fluorodesulfoxylation of the halosulfonyldifluoromethyl group yielded SOF2 as one of the two sulfur-containing oxides. Product analysis would suggest that both Lewis acid catalyzed and halogen exchange reactions are occurring and are dependent upon the starting halosulfonyldifluoromethyl material and Lewis acid.

1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent

The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.

Ozonides of perfluorooct-1-ene and perfluorooct-2-ene

Ozonides of higher perfluoroalkenes were prepared for the first time by ozonation of perfluorooct-1-and -2-enes in Freon-113. The structures of the resulting compounds were confirmed by 13C NMR spectroscopy and GLC-mass spectrometry.

Yield improvement in the electrochemical production of pefluorooctanoic acid

The possibility of obtaining real yield improvements in the industrial electrochemical production of perfluorooctanoic acid is discussed on the basis of recent experimental data obtained using perfluorohexyl acetyl chloride in place of octanoyl chloride as a starting material.In particular, the effect of the non-formation of cyclic byproducts on the yield of perfluoro-octanoic acid has been examined, as well as considering previous results obtained starting from a different partially fluorinated precursor, 4-perfluorobutyl butanoyl chloride.The yield of perfluoro-octanoic acid from perfluorohexyl acetyl chloride was less than expected, because of an accompanying increase in perfluoro-n-heptane formation.

AMINE(POLYFLUOROALKOXYACYL)IMIDE SURFACTANTS

Twenty-one examples (10a-d, 11a-l and 12a-e) of a new class of surfactants, the amine(polyfluoroalkoxyacyl)imides, were prepared by the reaction of esters containing polyfluoroalkoxy groups with tertiary alkylaminimides and hydroxyalkylaminimides.Included are five examples of difunctional aminacylimides that contain the hydrophilic portion of the molecule in the middle.These new surfactants are among the most potent known in their ability to form aqueous solutions with very low surface tensions and can be used to prepare stable emulsions of perfluorodecalin in water.Two new esters (ethyl perfluorooctyloxyacetate, 7, and ethyl 1H,1H-perfluorooctyloxyacetate, 9) used as intermediates to the surfactants were prepared by the alkylation of perfluoro- and 1H,1H-perfluorooctanol salts with ethyl bromoacetate.Other esters used in the preparation of the surfactants were derived from oligomers of hexafluoropropene oxide.

ELECTROCHEMICAL FLUORINATION OF 4-(PERFLUORO-n-BUTYL)-n-BUTANOYL CHLORIDE

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.