428-59-1

Basic information

• Product Name: Hexafluoropropylene oxide
• Synonyms: hexafluoropropyleneoxide(hfpo);NA 1956;Perfluoro(methyloxirane);Perfluoropropylene oxide;perfluoropropyleneoxide;Propane, 1,2-epoxy-1,1,2,3,3,3-hexafluoro-;Propylene oxide hexafluoride;propyleneoxidehexafluoride
• CAS NO: 428-59-1
• Molecular Formula: C₃F₆O
• Molecular Weight: 166.02
• EINECS: 207-050-4
• Product Categories: Fluoromonomer;Organic Fluorides
• Mol File: 428-59-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: -129°C
• Boiling Point: −42 °C(lit.)
• Appearance: colorless odorless gas
• Density: 1.67 g/cm³
• Vapor Pressure: 680.85kPa at 25℃
• Water Solubility: 16.3μg/L at 22.7℃
• CAS DataBase Reference: Hexafluoropropylene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Hexafluoropropylene oxide(428-59-1)
• EPA Substance Registry System: Hexafluoropropylene oxide(428-59-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-44
• Safety Statements: 7-26-37/39-38
• RIDADR: UN 1956 2.2
• WGK Germany: 3
• HazardClass: 2.2
• Hazardous Substances Data: 428-59-1(Hazardous Substances Data)

Usage

Uses

Hexafluoropropylene oxide is an important intermediate of organic fluorine material.HFPO is mainly used in the manufacture of high-quality fluorinated compounds.It is the main component of perfluor-vinyl ether(PPVE,PSVE,PFVE,PMVE) and the monomer of fluorinated surfactants and fluorinated ether oil.

General Description

Hexafluoropropylene oxide is a colorless odorless gas. Hexafluoropropylene oxide is shipped as a liquefied gas under its vapor pressure. Contact with the liquid can cause frostbite. Its vapors are heavier than air. Hexafluoropropylene oxide can cause asphyxiation by the displacement of air. Exposure of the container to prolonged heat or fire may cause Hexafluoropropylene oxide to rupture violently and rocket.

Reactivity Profile

Hexafluoropropylene oxide is a chlorinated epoxide. Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Health Hazard

Vapors may cause dizziness or asphyxiation without warning. Vapors from liquefied gas are initially heavier than air and spread along ground. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating, corrosive and/or toxic gases.

Fire Hazard

Some may burn but none ignite readily. Containers may explode when heated. Ruptured cylinders may rocket.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/6C3H6O.6FH/c6*1-3-2-4-3;;;;;;/h6*3H,2H2,1H3;6*1H/p-6

Synthetic route

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1)

Conditions	Yield
With 1-pyrrolidone In 1,1,2-Trichloro-1,2,2-trifluoroethane; N,N-dimethyl-formamide at 20℃; for 6h; Reagent/catalyst; Temperature; Solvent; Sealed tube;	95.6%
With sodium hypochlorite; sodium hydroxide In water; acetonitrile at -5 - 10℃; under 3750.38 Torr; Product distribution / selectivity;	69%
With borax; sodium perchlorate; sodium hydroxide In water; toluene at 0℃; pH=9.7 - 10.5; Reagent/catalyst; pH-value;	37.7%

perfluoropropylene (116-15-4) → polytetrafluoroethylene (116-14-3) + Hexafluoropropene oxide (428-59-1) + trifluoroacetyl fluoride (354-34-7) + 1,1,2,2,3,3-Hexafluoro-cyclopropane (931-91-9)

Conditions	Yield
With oxygen In tetrachloromethane at 155℃; for 3h;	A n/a B 62% C n/a D n/a

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + trifluoroacetyl fluoride (354-34-7)

Conditions	Yield
With oxygen In various solvent(s) at 140℃;	A 61.5% B 7%

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + freon-218 (76-19-7) + C3F12OSe + C3F16O2Se2

Conditions	Yield
With xenon bis-pentafluoroseleniumoxide at 65℃; for 84h;	A 36% B n/a C 51% D 11%

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + bis(pentafluoropropionyl)peroxide (356-45-6)

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide In methanol at -37℃; for 0.333333h;	A 35 g B 3%

epichlorohydrin (106-89-8) → Hexafluoropropene oxide (428-59-1)

Conditions	Yield
Elektrolyse in fluessigem Fluorwasserstoff;

perfluoropropylene (116-15-4) + difluorodioxirane (96740-99-7) → Hexafluoropropene oxide (428-59-1) + Carbonyl fluoride (353-50-4)

Conditions	Yield
In trichlorofluoromethane at 22℃; for 4h; other reaction partners: CF2CFCl, CF2CFH; reaction without solvent;	A 95 % Spectr. B n/a

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + Carbonyl fluoride (353-50-4)

Conditions	Yield
With difluorodioxirane In trichlorofluoromethane at 22℃; for 4h; Title compound not separated from byproducts;	A 95 % Spectr. B n/a

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + Carbonyl fluoride (353-50-4) + trifluoroacetyl fluoride (354-34-7)

Conditions	Yield
With oxygen at -60.15℃; under 750.06 Torr; Product distribution; Activation energy; Further Variations:; Temperatures; Pressures; Oxidation;

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + bis(pentafluoropropionyl)peroxide (356-45-6) + trifluoroacetic acid (76-05-1) + HF; CO2;

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide In methanol; water at -37℃; Product distribution; Mechanism; molar ratio of H2O2:HFP and of KOH:HFP;;

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + Carbonyl fluoride (353-50-4) + trifluoroacetyl fluoride (354-34-7) + perfluoropolyetherpolyperoxide

Conditions	Yield
With oxygen at 29.9℃; under 11025.9 Torr; Mechanism; Irradiation; stainless steel reactor; hexafluoropropene consumption rate, perfluoropolyetherpolyperoxide and carbonyl fluoride formation rate; different concentrations of hexafluoropropene and O2 pressures;

perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1) + 1,2-Dinitro-hexafluorpropan (507-58-4) + nitropentafluoroacetone (3888-00-4)

Conditions	Yield
With Nitrogen dioxide at 139.95 - 159.65℃; Kinetics;

polyoxyethylenelaurylether + perfluoropropylene (116-15-4) → Hexafluoropropene oxide (428-59-1)

perfluoro(propyl vinyl ether) (1623-05-8) → Hexafluoropropene oxide (428-59-1) + 3-azido-2-heptafluoropropoxytrifluoropropionic acid hydrate

Conditions	Yield
With carbon dioxide; sulfuric acid In water; dimethyl sulfoxide

Hexafluoropropene oxide (428-59-1) → α,α-dihydroxyperfluoropropionic acid (10321-14-9)

Conditions	Yield
With water In tetrahydrofuran at 20℃; for 6h;	100%
With water; silica gel In diethyl ether
With water In 1,4-dioxane

Hexafluoropropene oxide (428-59-1) + 2,2-dimethyl-propanol-1 (75-84-3) → neopentyl 2-neopentoxy-2,3,3,3-tetrafluoropropionate

Conditions	Yield
at 85℃; for 10h;	100%

Hexafluoropropene oxide (428-59-1) → 2,2,3,3,3-pentafluoropropionamide (354-76-7)

Conditions	Yield
With methylamine at 150℃; under 750.075 Torr; for 10h; Gas phase;	99.2%

Hexafluoropropene oxide (428-59-1) + 2-Isopropylimino-2-phenylethane (109106-15-2) → 5-isopropylamino-1,1,1,2,2-pentafluoro-5-phenylpent-4-en-3-one

Conditions	Yield
In diethyl ether at -60℃; for 9h;	99%

Hexafluoropropene oxide (428-59-1) + perfluoropelargonoyl fluoride (558-95-2) → FCF2OCFCF3COCF3CF2CF2CF2(CF2)4

Conditions	Yield
With bis[di(2-hydroxyethyl)amino]methane In acetonitrile at 25℃;	99%

Hexafluoropropene oxide (428-59-1) + diethyl sulfate (64-67-5) + perfluorobutyryl fluoride (335-42-2) → 1-{1-[(1-{[1-(ethoxydifluoromethyl)-1,2,2,2-tetrafluoroethoxy]difluoro-methyl}-1,2,2,2-tetrafluoroethoxy)difluoromethyl]-1,2,2,2-tetrafluoroethoxy}-1,1,2,2,3,3,3-heptafluoro-propane

Conditions	Yield
Stage #1: Hexafluoropropene oxide; perfluorobutyryl fluoride With potassium fluoride In diethylene glycol dimethyl ether for 24h; Stage #2: diethyl sulfate With potassium fluoride at 52℃; for 48h; Stage #3: With potassium hydroxide In diethylene glycol dimethyl ether; water at 65℃; for 5h;	98.8%

Hexafluoropropene oxide (428-59-1) + perfluoro(3-oxapentanoyl) fluoride (13071-64-2) → 2,3,3,3-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-pentafluoroethyloxy-ethoxy)-propionyl fluoride (39187-45-6)

Conditions	Yield
With bis(diethylamino)methane In diethylene glycol dimethyl ether at -15 - -10℃;	98%
With cesium fluoride In diethylene glycol dimethyl ether

Hexafluoropropene oxide (428-59-1) + trifluoroacetyl fluoride (354-34-7) → 2,3,3,3-tetrafluoro-2-(pentafluoroethoxy)propionic acid fluoride (1682-78-6)

Conditions	Yield
With bis(dimethylamino)methane In acetonitrile at -20℃;	98%

Hexafluoropropene oxide (428-59-1) + perfluoropropanoyl fluoride (422-61-7) → perfluoro(2-propoxypropionyl) fluoride (2062-98-8, 125037-08-3)

Conditions	Yield
With bis(diethylamino)methane In acetonitrile at -15℃;	98%
With potassium fluoride In diethylene glycol dimethyl ether

Hexafluoropropene oxide (428-59-1) + Perfluoro pentanoyl fluoride (375-62-2) → Perfluor-2-n-pentoxypropionylfluorid (13140-30-2)

Conditions	Yield
With dimorpholinomethane In diethylene glycol dimethyl ether at 15℃;	98%

Hexafluoropropene oxide (428-59-1) + phenol (108-95-2) → 4,4'-(hexafluoroisopropylidene)diphenol (1478-61-1)

Conditions	Yield
With TiClF3; SbF4Cl; hydrogen fluoride for 12h; Reagent/catalyst; Autoclave;	97.3%
With hydrogen fluoride; antimonypentachloride; titanium tetrachloride at 55℃; for 12h; Reagent/catalyst; Autoclave;	97.5%

Hexafluoropropene oxide (428-59-1) → Hexafluoroacetone (684-16-2)

Conditions	Yield
In water at 50℃; for 3h; Temperature; Reagent/catalyst; Large scale;	97%
With aluminum chlorofluoride at 25℃; for 1h;	96%
With aluminum chlorofluoride at 25℃; for 1h;	95%
With antimony pentafluoride at 60℃; Temperature; Inert atmosphere;	165.37 g

Hexafluoropropene oxide (428-59-1) + 4,1-polyisoprene-b-poly(ethylethylene) diblock copolymer, 1.4 percent hydrogenated isoprene units, PDI 1.08 (SEC), polyisoprene block 7.1 kg/mol, poly(ethylethylene) block 4.4 kg/mol; monomer(s): isoprene; sec-butyllithium; 1,3-butadiene → difluorocarbene-modified 4,1-polyisoprene-b-poly(ethylethylene), PDI 1.09 (SEC), polyisoprene block 7.1 kg/mol, poly(ethylethylene) block 4.4 kg/mol; monomer(s): isoprene; sec-butyllithium; 1,3-butadiene; perfluoropropylene oxide

Conditions	Yield
In cyclohexane at 180℃; for 4h;	97%

Hexafluoropropene oxide (428-59-1) + 2,2,3,3,4,4,5,5-octafluoro-pentanoyl fluoride (813-03-6) → FCF2OCFCF3COCF3CF2CF2CFH

Conditions	Yield
With dipiperidinomethane In acetonitrile at 15℃;	97%

Hexafluoropropene oxide (428-59-1) + Carbonyl fluoride (353-50-4) → 2,3,3,3-tetrafluoro-2-(trifluoromethoxy)propionic acid fluoride (2927-83-5)

Conditions	Yield
With dipiperidinomethane In acetonitrile at -20℃;	97%
Stage #1: Carbonyl fluoride With potassium fluoride; 18-crown-6 ether In diethylene glycol dimethyl ether at -5 - 0℃; under 11251.1 Torr; for 2h; Inert atmosphere; Autoclave; Large scale; Stage #2: Hexafluoropropene oxide In diethylene glycol dimethyl ether at -5 - 0℃; for 8h; Reagent/catalyst; Temperature; Pressure; Solvent; Large scale;	4 kg

Hexafluoropropene oxide (428-59-1) + difluorobromoacetyl fluoride (38126-07-7) → 2-(2-Bromo-1,1,2,2-tetrafluoro-ethoxy)-2,3,3,3-tetrafluoro-propionyl fluoride

Conditions	Yield
With dipiperidinomethane In acetonitrile at -15℃;	97%

Hexafluoropropene oxide (428-59-1) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 6,7-dimethyl-3-(trifluoromethyl)-2(1H)-quinoxalinone (143309-78-8)

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; dichloromethane for 12h; Ambient temperature;	96%

polytetrafluoroethylene (116-14-3) + Hexafluoropropene oxide (428-59-1) → 2,2-bis(trifluoromethyl)-3,3,4,4-tetrafluorooxetane (718-61-6)

Conditions	Yield
With aluminum chlorofluoride at 60℃; for 48h;	96%

methanol (67-56-1) + Hexafluoropropene oxide (428-59-1) → 2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7)

Conditions	Yield
With sodium carbonate at 20℃;	95%
Heating;	73%
Inert atmosphere;	27%

Hexafluoropropene oxide (428-59-1) + Difluoro-[1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-pentafluoroethyloxy-ethoxy)-ethoxy]-acetyl fluoride (13071-66-4) → C11F22O5

Conditions	Yield
With potassium fluoride; Tetraethylene glycol dimethyl ether at 25 - 31℃; for 0.666667h; Autoclave;	94.2%

Hexafluoropropene oxide (428-59-1) + ethanol (64-17-5) → 2-fluoro-2-ethoxy-trifluoropropionic acid ethyl ester (10186-66-0)

Conditions	Yield
With sodium hydroxide at 20℃; Reagent/catalyst;	93%
a) 1 h, b) 100 deg C, 3 h;	55%

Hexafluoropropene oxide (428-59-1) + o-xylene (95-47-6) → 4,4'-(perfluoropropane-2,2-diyl)bis(1,2-dimethylbenzene) (65294-20-4)

Conditions	Yield
With TiClF3; hydrogen fluoride for 11h; Autoclave; Large scale;	92.4%
With aluminum (III) chloride; hydrogen fluoride at 130℃; for 16h; Inert atmosphere;	107.67 g

Hexafluoropropene oxide (428-59-1) + ethanolamine (141-43-5) → N-pentafluoropropionyl-2-aminoethanol (6104-06-9)

Conditions	Yield
In acetonitrile for 0.5h; Ambient temperature;	92%

Hexafluoropropene oxide (428-59-1) + 1,1,2-trifluoro-4-bromobut-1-ene (10493-44-4) → 2-bromo-1-(1,2,2,3,3-pentafluorocyclopropyl)ethane

Conditions	Yield
at 190℃; for 12h;	92%
at 190℃; for 6h;	92%

Hexafluoropropene oxide (428-59-1) + perfluoro(5-oxa-6-heptenyl) cyanide (54675-68-2) → perfluoro(8-cyano-2,5-dimethyl-3,6-dioxanonanoyl) fluoride (54716-83-5)

Conditions	Yield
In further solvent(s)	91.3%

Hexafluoropropene oxide (428-59-1) → 1,1,2,2,3,3-Hexafluoro-cyclopropane (931-91-9)

Conditions	Yield
	91%

Hexafluoropropene oxide (428-59-1) + (5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))V=O → (5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))V(O(C(CF3)2)2O)

Conditions	Yield
In dichloromethane absence of air and moisture; stirring in (CF3)CFCOCF2-atmosphere for 1 h(pptn.); ether addn., stirring for 2 h, collection (filtration), washing (ether);elem. anal.;	91%

Hexafluoropropene oxide (428-59-1) + 1,2-diamino-benzene (95-54-5) → 3-(trifluoromethyl)quinoxalin-2-ol (58457-64-0)

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether at -78 - 20℃; for 16h;	91%

Hexafluoropropene oxide (428-59-1) + toluene (108-88-3) → 1,1,1,3,3,3-hexafluoro-2,2-di(p-tolyl)propane (1095-77-8)

Conditions	Yield
With SbF4Cl; hydrogen fluoride for 12h; Autoclave; Large scale;	90.6%

Upstream product

• 116-15-4 perfluoropropylene 
• 96740-99-7 difluorodioxirane 
• 1623-05-8 perfluoro(propyl vinyl ether) 
• 106-89-8 epichlorohydrin 

Downstream Products

• 2145-82-6 2-(pentafluoropropionyl)cyclohexanone 
• 1799-50-4 4,4,5,5,5-pentafluoro-1-phenyl-pentane-1,3-dione 
• 353-50-4 Carbonyl fluoride 
• 116-14-3 polytetrafluoroethylene 
• 354-34-7 trifluoroacetyl fluoride 
• 931-91-9 1,1,2,2,3,3-Hexafluoro-cyclopropane 
• 4089-57-0 5-fluorosulfonylpentafluoro-2-trifluormethyl-3-oxapentanoyl fluoride 
• 4089-58-1 8-fluorosulfonyl-2,5-bis(trifluoromethyl)octafluoro-3,6-dioxaoctanoyl fluoride 
• 4628-44-8 11-fluorosulfonyl-2,5,8-tris(trifluoromethyl)undecafluoro-3,6,9-trioxaundecanoyl fluoride 
• 16090-14-5 perfluoro(4-methyl-3,6-dioxaoct-7-ene)sulfonyl fluoride 
• 26954-17-6 2,4,4,5,5-pentafluoro-2-trifluoromethyl-3-oxathiolane-1,1-dioxide 
• 1645-83-6 1,3,3,3-tetrafluoro-propene 
• 22304-57-0 2,3,3,3-tetrafluoro-2-(pentafluorophenoxy)propionyl fluoride 
• 25711-77-7 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(pentafluorophenoxy)propoxy]propionyl fluoride 

Relevant articles and documents

Preparation method of hexafluoropropylene oxide (by machine translation)

The application belongs to, the technical field of inorganic chemistry, and particularly relates to a preparation method of. hexafluoropropylene oxide, and the preparation method of hexafluoropropene oxide comprises the, following steps of: reacting a nitrogen oxide, compound, with hexafluoropropylene as a,raw material to obtain hexafluoropropylene oxide as a raw material. (by machine translation)

Method for synthesis of hexafluoropropylene oxide by use of two-liquid-phase buffer solution method under atmospheric pressure

The present invention discloses a method for synthesis of hexafluoropropylene oxide by use of a two-liquid-phase buffer solution method under atmospheric pressure, and belongs to the technical field of fluorine chemical industry, and the method is as follows: under atmospheric pressure, sodium hypochlorite is used as an oxidant, a buffer system is used for assisting reaction, C12-C18 alkyl trimethyl ammonium bromide is used as a catalyst, and the two-liquid-phase method is used for synthesis of hexafluoropropylene oxide, the specific steps of the two-liquid-phase method are as follows: under atmospheric pressure, the buffer system is dissolved in an aqueous sodium hypochlorite solution, and then the C12-C18 alkyl trimethyl ammonium bromide and toluene are added into the aqueous sodium hypochlorite solution to form a mixture. The method is mild in reaction conditions, safe and reliable in production, low in power consumption, simple in process, low in production cost, better in environmental protection property, and high in economic efficiency.

A process for the preparation of hexafluoropropylene oxide

The invention discloses a preparation method for hexafluoropropylene oxide. Hexafluoropropylene is used for preparing hexafluoropropylene oxide through a molecular oxygen liquid-phase oxidation method. A hexafluoropropylene solvent used in the molecular oxygen liquid-phase oxidation method is mixture of perfluoropolyethers and fluorocarbon, and a metallic oxide catalyst is added in a reaction process of the molecular oxygen liquid-phase oxidation method. The preparation method has the advantages that the metallic oxide catalyst is added so that temperature required by a reaction is reduced, solubility of hexafluoropropylene in the solvent is greatly increased, and reaction selectivity is improved.