Hexafluoropropylene
[CAS# 116-15-4]

Identification

• Classification: Organic raw materials >> Organic fluorine compound
• Name: Hexafluoropropylene
• Synonyms: Perfluoropropene; 1,1,2,3,3,3-Hexafluoro-1-propene
• Molecular Formula: C₃F₆
• Molecular Weight: 150.02
• CAS Registry Number: 116-15-4
• EC Number: 204-127-4
• SMILES: C(=C(F)F)(C(F)(F)F)F

Properties

• Density: 1.4±0.1 g/cm³
• Melting point: -153 °C (Expl.)
• Index of refraction: 1.254, Calc.^*
• Boiling point: -29.4 °C (760 mmHg), Calc.^*, -28 °C (Expl.)
• Flash point: -40.3±10.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H280-H332-H335-H351-H371-H373-H412
• Safety Statements: P203-P260-P261-P264-P270-P271-P273-P280-P304+P340-P308+P316-P317-P318-P319-P403+P233-P405-P410+P403-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Gases under pressure (liquid)	Press. Gas (Liq.)		H280
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - single exposure	STOT SE	2	H371
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Gases under pressure (compressed)	Press. Gas (Comp.)		H280

• Transport Information: UN 1858

Discovery and Applications

Hexafluoropropylene is a versatile fluorinated organic compound with the chemical formula C3HF6. This trifluoromethylated alkene is widely recognized for its role as a precursor in the synthesis of various fluoropolymers and specialty chemicals. Its unique properties, including high thermal and chemical stability, make it an indispensable substance in multiple industrial applications.

The discovery and development of hexafluoropropylene were driven by the need for advanced materials resistant to extreme environmental conditions. Early investigations into fluorinated hydrocarbons revealed that hexafluoropropylene exhibits remarkable inertness and low surface energy, leading to its use in the production of high-performance fluoropolymers such as polyvinylidene fluoride (PVDF) and fluoroelastomers. These materials are critical in applications where durability and resistance to harsh chemicals are required, including aerospace, automotive, and chemical processing industries.

Hexafluoropropylene is typically synthesized via the pyrolysis of chlorodifluoromethane or related halogenated compounds. Advanced industrial methods have been developed to ensure high yields and minimal by-products. The introduction of catalytic processes has further optimized production efficiency, aligning with sustainability goals by reducing energy consumption and waste.

The compound is most prominently used in copolymerization reactions to produce fluorinated polymers. For example, hexafluoropropylene copolymerizes with tetrafluoroethylene to form fluorinated ethylene propylene (FEP), a material with excellent electrical insulation and non-stick properties. FEP is extensively used in the manufacturing of wires, cables, and non-stick coatings. Additionally, hexafluoropropylene oxide, derived from the compound, serves as an intermediate in producing perfluoropolyethers, which are used as lubricants and greases in demanding environments.

In recent years, research has expanded into exploring new applications for hexafluoropropylene and its derivatives, including their use in energy storage and advanced coatings. The compound’s ability to impart unique properties, such as low refractive indices and excellent dielectric performance, has made it a focus of study in emerging technologies.

References

2011. Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology, classification, and origins. Integrated Environmental Assessment and Management.
DOI: 10.1002/ieam.258

2005. Palladium(0)-Catalyzed Hydroalkoxylation of Hexafluoropropene: Synthesis of Hydrofluoroethers under Neutral Conditions. Angewandte Chemie (International ed. in English).
DOI: 10.1002/anie.200462200

2002. Conversion of hexafluoropropene into 1,1,1-trifluoropropane by rhodium-mediated C[bond]F activation. Angewandte Chemie (International ed. in English).
DOI: 10.1002/1521-3773(20020802)41:15<2745::aid-anie2745>3.0.co;2-c