355-38-4

Usage

Uses

Used in Fluorochemical Production:
PERFLUOROHEXANOYL FLUORIDE 98 is used as an intermediate for the production of various fluorochemicals due to its high fluorination and chemical stability.
Used in Specialty Polymer Manufacturing:
It serves as a key component in the manufacturing of specialty polymers, which are known for their unique properties and applications in different industries.
Used in Surfactant Production:
PERFLUOROHEXANOYL FLUORIDE 98 is used as a raw material in the production of surfactants, which are essential in various industrial processes for their wetting, emulsifying, and dispersing properties.
Used in Pharmaceutical Industry:
It is utilized in the pharmaceutical industry as a starting material for the synthesis of various pharmaceutical compounds, taking advantage of its unique chemical properties.
Used in Agrochemical Production:
PERFLUOROHEXANOYL FLUORIDE 98 is used in the production of agrochemicals, contributing to the development of effective and stable pesticides and other agricultural chemicals.
Used in Electronics Industry:
It is employed in the production of fluoropolymer additives and coatings for applications in the electronics industry, where its resistance to solvents, acids, and bases is highly beneficial.
Used in Aerospace and Automotive Industries:
PERFLUOROHEXANOYL FLUORIDE 98 is used in the aerospace and automotive industries for the production of high-performance coatings and materials that can withstand extreme conditions.
However, it is crucial to handle PERFLUOROHEXANOYL FLUORIDE 98 with care, as it is flammable and may cause skin and eye irritation.

InChI:InChI=1/C6F12O/c7-1(19)2(8,9)3(10,11)4(12,13)5(14,15)6(16,17)18

Synthetic route

2,2,3,3,4,4,5,5,6,6,6-Undecafluoro-hexanoic acid 1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-icosafluoro-1-trifluoromethyl-decyl ester (210972-72-8) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
at 182 - 224℃;	73%

7-oxabicyclo(2.2.1)heptane (279-49-2) → perfluoropentane (678-26-2) + perfluorohexanoyl fluoride (355-38-4) + perfluoro(2-ethyltetrahydrofuran) (356-48-9)

Conditions	Yield
With fluorine at -120 - 20℃; for 336h; Yields of byproduct given;	A n/a B n/a C 26.2%
With fluorine at -120 - 20℃; for 336h; Yield given;	A n/a B n/a C 26.2%

dihexyl ether (112-58-3) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With hydrogen fluoride anodische Fluorierung;

hexanoic acid (142-62-1) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With hydrogen fluoride anodische Fluorierung;

perfluoro-2-octene (65500-50-7) → trifluoroacetyl fluoride (354-34-7) + perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With ozone; trifluoroacetic acid at -18 - 0℃; Yield given. Yields of byproduct given;

Perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine (143813-73-4, 145733-85-3) → perfluorohexanoyl fluoride (355-38-4) + C6F13N

Conditions	Yield
With cesium fluoride at 100 - 110℃; for 12h; Yield given. Yields of byproduct given;

perfluoro-1-pentoxy-2-azaoct-1-ene → perfluorohexanoyl fluoride (355-38-4) + C6F13N

Conditions	Yield
With cesium fluoride at 100℃; for 12h; Yield given. Yields of byproduct given;

(E)-perfluorooct-2-ene (31143-13-2) + trifluoroacetic acid (76-05-1) → perfluorohexanoyl fluoride (355-38-4) + trifluoroacetyl peroxide (359-48-8)

Conditions	Yield
With oxygen; ozone at 0℃; Rate constant; var. reaction conditions; also in the presence of SbF5 and HClO4;

cyclohexanol (108-93-0) → perfluoropentane (678-26-2) + perfluorohexanoyl fluoride (355-38-4) + perfluorocyclohexane (355-68-0)

Conditions	Yield
With fluorine -120 deg C to r.t.; Yields of byproduct given;	A 1.2 g B n/a C n/a
With fluorine -120 deg C to r.t.; Yield given;	A 1.2 g B n/a C n/a

trans-3,5-difluoro-5-perfluoropentyl-3-trifluoromethyl-1,2,4-trioxolane + cis-3,5-difluoro-5-perfluoropentyl-3-trifluoromethyl-1,2,4-trioxolane → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Ring cleavage; Heating;

perfluoro-2-octene (65500-50-7) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: O3; O2 / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 2 h / 15 - 20 °C 2: Heating View Scheme

Perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine (143813-73-4, 145733-85-3) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 150 - 170 °C 2: CsF / 12 h / 100 °C View Scheme

n-perfluorohexyl iodide (355-43-1) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With phosphorus pentachloride; sulfuric acid at 20 - 70℃; for 17.5h;	58.7 %Chromat.

mercury(II) fluoride + perfluorohexanoyl cyanide dimer → perfluorohexanoyl fluoride (355-38-4)

perfluorohexanoyl cyanide dimer + silver fluoride → perfluorohexanoyl fluoride (355-38-4)

hexanoyl fluoride (372-80-5) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Electrochemical reaction;

perfluorohexanoyl fluoride (355-38-4) + p-phenylbenzyl bromide (2567-29-5) → C19H11F13O

Conditions	Yield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 12h; Temperature; Reagent/catalyst; Inert atmosphere;	78%

perfluorohexanoyl fluoride (355-38-4) + allyl bromide (106-95-6) → C9H5F13O

Conditions	Yield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;	75%

perfluorohexanoyl fluoride (355-38-4) + ethyl iodide (75-03-6) → C8H5F13O

Conditions	Yield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;	30%

methanol (67-56-1) + perfluorohexanoyl fluoride (355-38-4) → perfluorohexanoic acid methyl ester (424-18-0)

perfluorohexanoyl fluoride (355-38-4) → undecafluoro-hexanoic acid amide (335-54-6)

Conditions	Yield
With ammonia

Hexafluoropropene oxide (428-59-1) + perfluorohexanoyl fluoride (355-38-4) → F(CF2)6OCF(CF3)COF (13140-31-3)

Conditions	Yield
With Tetraethylene glycol dimethyl ether; cesium fluoride at 0 - 20℃; under 0 Torr;	79.6 %Chromat.

Upstream product

• 112-58-3 dihexyl ether 
• 142-62-1 hexanoic acid 
• 279-49-2 7-oxabicyclo(2.2.1)heptane 
• 65500-50-7 perfluoro-2-octene 
• 143813-73-4 Perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine 
• 31143-13-2 (E)-perfluorooct-2-ene 
• 76-05-1 trifluoroacetic acid 
• 108-93-0 cyclohexanol 
• 210972-72-8 2,2,3,3,4,4,5,5,6,6,6-Undecafluoro-hexanoic acid 1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-icosafluoro-1-trifluoromethyl-decyl ester 
• 355-43-1 n-perfluorohexyl iodide 
• 7783-39-3 mercury(II) fluoride 
• 11113-87-4 silver fluoride 
• 372-80-5 hexanoyl fluoride 

Downstream Products

• 424-18-0 perfluorohexanoic acid methyl ester 
• 335-54-6 Perfluorhexanamid 

Relevant academic research and scientific papers

Homogeneous catalytic hydrogenation of perfluoro methyl esters

The first example of perfluoroalkyl methyl ester RfC(O)OMe (Rf = C3F7, C5F11) reduction by homogeneous catalytic hydrogenation with the ruthenium catalyst Ru-MACHO is herein reported. The hydrogenation process leads to the corresponding perfluorinated alcohols thus replacing sodium borohydride that has so far represented the state of art in perfluoro ester reduction.

FLUORINE-CONTAINING ETHER COMPOUND

A novel fluorinated ether compound useful as an inert medium is provided. The compound is represented by the following formula (1) such as the compound represented by the following formula (1a) or the compound represented by the following formula (1b): ????????RF1OCFRF2CFRF2ORF1?????(1) ????????F (CF2)4OCF(CF3)CF(CF3)O(CF2)4F?????(1a) ????????F(CF2)6OCF(CF3)CF(CF3)O(CF2)6F?????(1b) wherein the symbols have the following meanings: RF1 is a C4-7 linear perfluoroalkyl group; andRF2 is a fluorine atom or a trifluoromethyl group.

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.

Some Novel Reactions of Perfluoro-2,3-dialkyloxaziridines

Perfluoro-2,3-dialkyloxaziridines rearrange at 120-160 deg C into RfN=CF-OR'f quantitatively.Reaction with SbF5 at elevated temperature leads to the formation of the isomeric alkoxy imines RfON=CFR'f.Reaction with CsF in the absence of a solvent results in formation of a mixture of the corresponding acyl fluoride R'fC(O)F and N-fluoro imine R'fCF=NF.In contrast, reaction between perfluoro-2-butyl-3-propyloxaziridine and CsF in MeCN produces C4F9ON=CFC3F7.Interaction of this oxaziridine with polyfluoro ketones and COF2 in the presence of CsF in polar solvents leads to the formation of alkoxy imines R''fON=CFC3F7.

Synthesis of Functional Perfluorinated Resins, Branched Perfluorinated Ethers and Perfluoroalkanoyl Fluorides

Functional-group-containing perfluorinated resins have been prepared by carefully controlled direct fluorination of poly-(3-methyloxetane-3-methanol).Branched perfluorinated ethers such as bis(perfluoroneopentyl) ether and perfluoro-(2,2-dimethylbutyl methyl ether) have also been synthesized by direct fluorination of alkanols.The by-products, perfluoroalkanoyl fluorides, are useful intermediates.

Synthesis of Unusual Perfluorocarbon Ethers and Amines Containing Bulky Fluorocarbon Groups: New Biomedical Materials

The reactions of elemental fluorine with structually crowded hydrocarbon ethers and amines have been studied.The perfluorinated products are currently of interest in biomedical or electronic industrial applications.The syntheses by direct fluorination of perfluoro(tert-butyl methyl ether), perfluoro(tert-butyl isobutyl ether), perfluoro(1,2-di-tert-butoxyethane), perfluoro(cyclohexyl neopentyl ether), perfluoro(2,2,5,5-tetramethyltetrahydrofuran), perfluoro(2,5-dimethyltetrahydrofuran), bis(perfluoroisopropyl) ether, perfluoro(2-ethyltetrahydrofuran), and perfluoro(1,2,2,6,6-pentamethylpiperidine) are reported.The skeletally rearranged byproducts perfluoro(isobutyl methyl ether), perfluoro(2,2,5-trimethyltetrahydrofuran), perfluoro(2,2,5-trimethyltetrahydropyran), 3-hydropentadecafluoro-2,2,5,5-tetramethyltetrahydrofuran, perfluoro(isopropyl propylether), and perfluoro(ethyl isopropyl ether) were also characterized.The 19F and 13C (19F decoupled) NMR assignments of these perfluorinated chemicals are discussed.