Hexafluoropropylene oxide
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Basic information
- CAS
428-59-1- Standard SMILES
FC(F)(F)C1(F)OC1(F)F- InChIKey
PGFXOWRDDHCDTE-UHFFFAOYSA-N- Molecular formula
- C3F6O
- Average molar mass
- 166.02 g/mol
- Monoisotopic mass
- 165.98533359
Overview
Hexafluoropropylene oxide is a colorless odorless gas. It is shipped as a liquefied gas under its vapor pressure. Contact with the liquid can cause frostbite. Its vapors are heavier than air. It can cause asphyxiation by the displacement of air. Exposure of the container to prolonged heat or fire may cause it to rupture violently and rocket.
Names & identifiers
- Preferred name
- Hexafluoropropylene oxide
- IUPAC
- 2,2,3-trifluoro-3-(trifluoromethyl)oxirane
- English name
- Hexafluoropropylene oxide
- Molecular formula
- C3F6O
- Molecular weight
- 166.02
Names & synonyms
Hexafluoropropylene oxide428-59-1Hexafluoropropene oxide2,2,3-Trifluoro-3-(trifluoromethyl)oxiraneHfpoTRIFLUORO(TRIFLUOROMETHYL)OXIRANEPerfluoropropylene oxideHexafluoro-1,2-epoxypropaneHexafluoropropene epoxideHexafluoroepoxypropaneHexafluoropropylene epoxidePropylene oxide hexafluoride
Show more names
1,1,2,3,3,3-Hexafluoro-1,2-epoxypropaneC3F6ONA 1956(S) TRIMETHYLOXIRANE
Oxirane, trifluoro(trifluoromethyl)-JPY12AP87NPropane, 1,2-epoxy-1,1,2,3,3,3-hexafluoro-RefChem:146014ACETONE, HEXAFLUOROHFPO hexafluoropropylene oxide207-050-4Poly(perfluoropropyleneoxide)
Database identifiers
- CAS
428-59-1- PubChem CID
- 9883
- DTXSID
DTXSID6029177- UNII
- JPY12AP87N
- EC Number
- 207-050-4
- Nikkaji
- J27.198E
Properties
Computed structural propertiesFilling in
- XLogP
- 2.1
- Topological polar surface area
- 12.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 161
Experimental & physicochemical properties
PFAS
PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds
PFAS -> Other/unspecified
PFAS -> OECD Category
PFAS
PFAS -> Intentionally added food contact chemicals
PolymersPlastics & Rubber -> Other Monomers
Boiling Point-18 °F at 760 mmHg (NTP, 1992)
Decomposition
AT TEMP BETWEEN 500-800 °C, CARBONYL FLUORIDE (COF2) IS DOMINANT PYROLYSIS PRODUCT. THIS GAS IS VERY SUSCEPTIBLE TO HYDROLYSIS, READILY YIELDING HYDROFLUORIC ACID & CARBON DIOXIDE. ABOVE 800 °C, THE PYROLYSIS PRODUCTS CONSIST OF INORGANIC FLUORIDE, A LITTLE TETRAFLUOROMETHANE & CARBON DIOXIDE. /POLYFLUORINES/
Melting Point-200 °F (NTP, 1992)
Physical Description
Hexafluoropropylene oxide is a colorless odorless gas. It is shipped as a liquefied gas under its vapor pressure. Contact with the liquid can cause frostbite. Its vapors are heavier than air. It can cause asphyxiation by the displacement of air. Exposure of the container to prolonged heat or fire may cause it to rupture violently and rocket.
Gas Vapor; CBI; Liquid
Colorless odorless gas; Shipped liquefied under its vapor pressure; [CAMEO]
Physicochemical properties
- Melting point
- -129 °C · -129°C
- Boiling point
- 42 °C · −42 °C(lit.)
- Density
- 1.67 · 1.67±0.1 g/cm3(Predicted)
- vapor pressure
- 680.85 kPa · 680.85kPa at 25℃
- Water Solubility
- 16.3 μg/L · 16.3μg/L at 22.7℃
- Henry's Law Constant
- 9.3 · 9.3×10-6 mol/(m3Pa) at 25℃, Clever et al. (2005)
- InChI
- InChI=1S/C3F6O/c4-1(2(5,6)7)3(8,9)10-1
- InChIKey
- PGFXOWRDDHCDTE-UHFFFAOYSA-N
- SMILES
- O1C(F)(C(F)(F)F)C1(F)F
- LogP
- 1.72 at · 1.72 at 25℃
- CAS DataBase Reference
- 428 · 428-59-1(CAS DataBase Reference)
- FDA UNII
- 12 AP87N · JPY12AP87N
- NIST Chemistry Reference
- Oxirane, trifluoro(trifluoromethyl)-(428-59-1)
- EPA Substance Registry System
- 2 · Oxirane, 2,2,3-trifluoro-3-(trifluoromethyl)- (428-59-1)
- Symbol(GHS)
- 5 · GHS05,GHS02
- Signal word
- Danger
- Hazard statements
- 314 · H314-H225-H290
- Precautionary statements
- 501 · P501-P240-P210-P233-P234-P243-P241-P242-P264-P280-P370+P378-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-44
- Safety Statements
- 7 · 7-26-37/39-38
- RIDADR
- 1956 · UN 1956 2.2
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 2.2 · 2.2
- Hazardous Substances Data
- 428 · 428-59-1(Hazardous Substances Data)
- REACH Registrations
- Active
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 24.2% (16 of 66) of reports.
Danger
H280 (74.2%): Contains gas under pressure; may explode if heated [Warning Gases under pressure]
P260, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P410+P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Oxirane, 2,2,3-trifluoro-3-(trifluoromethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxirane, 2,2,3-trifluoro-3-(trifluoromethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
S - indicates a substance that is identified in a final Significant New Use Rule.
REACH registered substance: Trifluoro(trifluoromethyl)oxirane (EC: 207-050-4)
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelNon-Flammable Gas
Fire HazardsExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Health HazardsExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Hazards Summary
May polymerize; Containers may explode from prolonged heat; Evaporating liquid can cause frostbite; In confined space spill, may displace air and act as simple asphyxiant; [CAMEO] May explode if heated under confinement; An irritant; In confined space spill, may displace air and act as simple asphyxiant; [MSDSonline]
Reactive GroupEpoxides
Reactivity AlertsPolymerizable
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.
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Hazard Classes and Categories
Press. Gas (Comp.) (74.2%)
Gases under pressure - Low pressure liquefied gas
Shipping Name/ Number DOT/UN/NA/IMONA 1956; Hexafluoropropylene oxide
Safety & protection
Fire FightingExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill ResponseExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Preventive Measures
VENTILATION CONTROL: ...WHERE...RESINS ARE LIKELY TO UNDERGO PYROLYSIS & DECOMP DURING PROCESSING, PROVISION SHOULD BE MADE FOR ADEQUATE LOCAL EXHAUST & GENERAL VENTILATION TO KEEP CONCN OF DECOMP PRODUCTS AS LOW AS POSSIBLE. /POLYFLUORINES/
Isolation and EvacuationExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Toxicology
Adverse EffectsOther Poison - Simple Asphyxiant
Human Toxicity Excerpts
A UNIQUE EFFECT FROM PYROLYSIS PRODUCTS OF PTFE /POLYTETRAFLUOROETHYLENE/ RESINS...BEEN OBSERVED IN MAN... THIS IS AN INFLUENZA-LIKE SYNDROME RESEMBLING METAL FUME FEVER & HAS BEEN TERMED "POLYMER FUME FEVER". IT IS SELF-LIMITING, LASTS...24-48 HR & REQUIRES ONLY SYMPTOMATIC TREATMENT. /POLYFLUORINES/
Non-Human Toxicity Excerpts
IN ACUTE STUDIES WITH MICE & RATS IT CAUSED CHANGES IN LIVER & KIDNEY. IN SPLEEN IT CAUSED VASCULAR PERMEABILITY & DEGENERATIVE DYSTROPHIC CHANGES & INFLAMMATION. EXTENT & NATURE OF TOXICITY DEPENDS UPON TYPE OF METABOLITES THAT ARE PRODUCED.
Probable Routes of Human Exposure
A UNIQUE EFFECT FROM PYROLYSIS PRODUCTS OF PTFE /POLYTETRAFLUOROETHYLENE/ RESINS...BEEN OBSERVED IN MAN... THIS IS AN INFLUENZA-LIKE SYNDROME RESEMBLING METAL FUME FEVER & HAS BEEN TERMED "POLYMER FUME FEVER". IT IS SELF-LIMITING, LASTS...24-48 HR & REQUIRES ONLY SYMPTOMATIC TREATMENT. /POLYFLUORINES/
Safety data
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1956 2.2
- risk_code
- 36/37/38-44
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS02
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 7-26-37/39-38
- hazard_class
- 2.2
- Hazard statements
- H314-H225-H290
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Precautionary statements
- P501-P240-P210-P233-P234-P243-P241-P242-P264-P280-P370+P378-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405
- Hazardous Substances Data
- 428-59-1(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as monomer for heat-resistant hexafluoropropylene oxide polymers; [HSDB]
MONOMER FOR HEXAFLUOROPROPYLENE OXIDE POLYMERS THAT ARE HEAT RESISTANT TO 410 °C
U.S. Production2023: 2,500,000 - <4,000,000 lb
Industry UsesIntermediate
Methods of ManufacturingOXIDATION OF HEXAFLUOROPROPYLENE WITH ALKALINE HYDROGEN PEROXIDE...ABOUT -30 °C.
Use ClassificationPFAS (per- and polyfluoroalkyl substances) -> OECD Category
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Oxirane, 2,2,3-trifluoro-3-(trifluoromethyl)-: ACTIVE
"FREON E" /IS/ TRADEMARK FOR SERIES OF HYDROGEN END-CAPPED TETRAFLUOROETHYLENE EPOXIDE POLYMERS HAVING A DP /DEGREE OF POLYMERIZATION/ UP TO 10. BOILING RANGE 39-490 °C. HIGH DIELECTRIC CONSTANT. USED AS COOLANTS IN ELECTRONIC DEVICES. /FREON E/
"KRYTOX" /IS/ TRADEMARK FOR A SERIES OF HEXAFLUOROPROPYLENE EPOXIDE POLYMERS OF MEDIUM MOLECULAR WT, USED AS LUBRICATING OILS & GREASES. FOR USE IN HIGH TEMP OR CORROSIVE CONDITIONS; GOOD CHEM INERTNESS, EVEN WITH BOILING SULFURIC ACID; LOW SOLUBILITY IN MOST SOLVENTS; GOOD LUBRICITY UNDER LOAD... /KRYTOX/
Applications
UsesHexafluoropropylene 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 DescriptionHexafluoropropylene 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
20 records
Compound notes
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