Hexafluoropropylene

HCID 8302CAS 116-15-4

Basic information

Standard SMILES
FC(F)=C(F)C(F)(F)F
InChIKey
HCDGVLDPFQMKDK-UHFFFAOYSA-N
Molecular formula
C3F6
Average molar mass
150.02 g/mol
Monoisotopic mass
149.99041932

Overview

Hexafluoropropylene is an odorless, colorless gas. It is noncombustible. It can asphyxiate by the displacement of air. Exposure of the container to prolonged heat or fire can cause it to rupture violently and rocket.

Names & identifiers

Preferred name
Hexafluoropropylene
IUPAC
1,1,2,3,3,3-hexafluoroprop-1-ene
English name
Hexafluoropropylene
Molecular formula
C3F6
Molecular weight
150.02

Names & synonyms

HexafluoropropeneHexafluoropropylene116-15-4PerfluoropropenePerfluoropropylenePropene, hexafluoro-Perfluoro-1-propenePropylene, hexafluoro-Hexfluoropropylene1,1,2,3,3,3-HEXAFLUORO-1-PROPENE1-Propene, 1,1,2,3,3,3-hexafluoro-propylene hexafluoride
Show more names
CF3CF=CF2HexafluorpropenPerfluoroprop-1-eneHexafluofoproenehexafluoro-propen
TRW23XOS20DTXSID2026949RefChem:146013DTXCID206949204-127-41,1,2,3,3,3-hexafluoroprop-1-eneC3F6MFCD00000447

Database identifiers

CAS
116-15-4
PubChem CID
8302
DTXSID
DTXSID2026949
ChEMBL
CHEMBL4644489
UNII
TRW23XOS20
EC Number
204-127-4
Nikkaji
J35.205E

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
0
Heavy atoms
9

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Halogenated Aliphatics, Unsaturated

Reactive agents - 1st degree

PFAS · 5 items

PFAS -> Other/unspecified

PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

PFAS -> Other/unspecified

PFAS -> Other/unspecified

PFAS -> Intentionally added food contact chemicals

SpringerMaterials PropertiesSchoenflies notation
OdorOdorless gas
Density · 2 items

1.583 AT -40 °C/4 °C

1.583 @ -40°C

Color/FormColorless gas

Physicochemical properties

Melting point
153 °C · −153 °C(lit.)
Boiling point
28 °C · −28 °C(lit.)
Density
1 · 1,583 g/cm3
vapor pressure
587.952 kPa · 587.952kPa at 25℃
refractive index
1.4 · 1.4000
form
gas

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P304+P340, P317, P319, P403+P233, P405, and P501 (click each P-code to see the statement)

Warning

H280 (89.5%): Contains gas under pressure; may explode if heated [Warning Gases under pressure]

P203, P260, P261, P264, P270, P271, P273, P280, P304+P340, P308+P316, P317, P318, P319, P403+P233, P405, P410+P403, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Chemical: 1-Propene, 1,1,2,3,3,3-hexafluoro-

1-Propene, 1,1,2,3,3,3-hexafluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propene, 1,1,2,3,3,3-hexafluoro- 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)

Status: Active Update: 03-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15192

Hexafluoropropene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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.)

Other Safety InformationIMAP assessments - 1-Propene, 1,1,2,3,3,3-hexafluoro-: Human health tier I assessment
DOT LabelNon-Flammable Gas
Fire Hazards · 3 items

Excerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:

· Some may burn but none ignite readily.

· Some may burn but none ignite readily.

Health Hazards · 3 items

Excerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:

· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas.

· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas.

Hazards SummaryProduces acute tubular necrosis in experimental animals exposed to high concentrations; [HSDB] A respiratory tract irritant; The kidney is the target organ; [ACGIH]

Safety & protection

Fire FightingExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Accidental Release Measures · 4 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch or walk through spilled material.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch or walk through spilled material.

First Aid · 3 items

Excerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:

General First Aid:

General First Aid:

Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Nonfire Spill ResponseExcerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:
Isolation and Evacuation · 3 items

Excerpt from ERG Guide 126 [Gases - Compressed or Liquefied (Including Refrigerant Gases)]:

Immediate precautionary measure

Immediate precautionary measure

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that hexafluoropropene is expected to have moderate mobility in soil(SRC). Volatilization of hexafluoropropene is expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.34 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Hexafluoropropene is expected to rapidly volatilize from dry soil surfaces based on a vapor pressure of 4.9X10+3 mm Hg(SRC), determined from a fragment constant method(4). Highly chlorinated/fluorinated compounds are not expected to biodegrade rapidly(5).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that hexafluoropropene is expected to adsorb to suspended solids and sediment in water(SRC). Hexafluoropropene is expected to volatilize rapidly from water surfaces(3,SRC) based on an estimated Henry's Law constant of 5.34 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 4 and 116 hours, respectively(3,SRC). According to a classification scheme(5), an estimated BCF value of 24(3,SRC), from an estimated log Kow of 2.12(6,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Highly chlorinated/fluorinated compounds are not expected to biodegrade rapidly(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexafluoropropene, which has a vapor pressure of 4.9X10+3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexafluoropropene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC); the half-lives for these reactions in air are estimated to be about 21(3,SRC) and 95(4,SRC) days, respectively.

Adverse EffectsOther Poison - Simple Asphyxiant
Effluent ConcentrationsHexafluoropropene was identified, not quantified, in the stack emissions of a hazardous waste incinerator(1).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for hexafluoropropene can be estimated to be about 470(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that hexafluoropropene is expected to have moderate mobility in soil(SRC).

TSCA Test Submissions · 1 item

The ability of hexafluoropropene (HFP) to cause aberrations in Chinese hamster ovary (CHO) cells in vitro was evaluated in the presence and absence of rat liver S9 metabolic activation. Based on preliminary toxicity tests, nonactivated cultures were treated with 0, 0.01, 0.02, 0.10, 0.17, 0.29, 0.37, 0.43 or 0.59% HFP and activated cultures were treated with 0, 0.09, 0.17, 0.33, 0.46, 0.55, 0.67, 0.85, 1.40% HFP. Significant increases were observed in numbers of aberrations/cell, percent abnormal cells, and percent cells with >1 aberration relative to controls in nonactivated and activated cultures at the highest four dose levels (0.29% and 0.55% and above, respectively). Positive dose-related trends were observed for all three measurements in both nonactivated and activated cultures.

Artificial Pollution SourcesHexafluoropropene's production and use in the manufacture of copolymers and hexafluoropropylene oxide(1), may result in its release to the environment through various waste streams(SRC).

Regulatory information

TSCA RequirementsManufacturers and processors of hexafluoropropene are required to conduct health effects testing under TSCA section 4.

Safety data

F
4.5
PPE
Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
1
tsca
TSCA listed
rtecs
UD0350000
ridadr
UN 1858 (HEXAFLUOROPROPYLENE (REFRIGERANT GAS R 1216))

Chemistry & industry

Uses & manufacturing

Uses · 5 items

About 90% is used as a monomer in closed systems to produce fluoropolymers, fluoroelastomers, and fluorolubricants; About 10% is used to produce replacement chlorofluorocarbons; [ACGIH]

MONOMER FOR FLUORINATED ETHYLENE-PROPYLENE COPOLYMERS

COMONOMER FOR VINYLIDENE FLUORIDE ELASTOMERS

CHEM INT FOR PERFLUOROALKYL POLYETHER FLUIDS

Production of copolymers and hexafluoropropylene oxide.

U.S. Production · 3 items

2023: 10,000,000 - <25,000,000 lb

(1977) AT LEAST 4.54X10+8 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Consumption PatternsREFRIGERANTS, 39%; FOAM BLOWING AGENTS, 17%; SOLVENTS, 14%; FLUOROPOLYMERS, 14%; STERILANT GAS, 2%; AEROSOL PROPELLANTS, 2%; FOOD FREEZANT, 1%; OTHER, 8%; EXPORTS, 3% (1985) /FLUOROCARBONS/
Consumer UsesMonomers
Industry UsesIntermediate
Methods of Manufacturing · 2 items

BY-PRODUCT IN THE PRODUCTION OF TETRAFLUOROETHYLENE BY REACTION OF HYDROGEN FLUORIDE WITH CHLOROFORM IN THE PRESENCE OF ANTIMONY TRIFLUORIDE CATALYST, FOLLOWED BY PYROLYSIS; PYROLYSIS OF POLYTETRAFLUOROETHYLENE; FLUORINATION OF 1,2,3-TRICHLOROPROPANE, THEN DEHALOGENATION

Produced by temperature controlled pyrolysis of chlorodifluoromethane. Also obtained from tetrafluoroethylene by heating at normal or reduced pressure in the presence of an inert gas or water vapor.

Applications · 2 items

UsesHexafluoropropene is used in the synthesis of polyvinylidene fluoride-co-hexafluoropropylene, a polymer which is currently being used in various fields of the nano and electronic sector ranging from membranes to nanoparticles.

General DescriptionHexafluoropropylene is an odorless, colorless gas. Hexafluoropropylene is noncombustible. Hexafluoropropylene can asphyxiate by the displacement of air. Exposure of the container to prolonged heat or fire can cause Hexafluoropropylene to rupture violently and rocket.

Preparation methods · 1 item

PreparationHexafluoropropylene can be produced by pyrolysis of tetrafluoroethylene (TFE):3 CF2=CF2 → 2 CF3CF=CFThis reaction is carried out in a closed continuous reactor at 600 to 900°C. The yield can be improved at low partial pressure, achieved either by operating under reduced total pressure (down to 0.1 bar) or by injecting an inert diluent such as steam or CO2.Significant quantities of by-products, including the highly toxic perfluoroisobutylene (PFIB), are formed during the pyrolysis of TFE. Such by-products are either incinerated directly or are collected and transported for incineration at a remote facility.Hexafluoropropylene can also be prepared from chlorodifluoromethane, or produced from various chlorofluorocarbons.

Related reactions

126 records

Linked notes

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