Heptafluoropropyl trifluorovinyl ether
[CAS# 1623-05-8]

Identification

• Classification: Organic raw materials >> Organic fluorine compound
• Name: Heptafluoropropyl trifluorovinyl ether
• Synonyms: 1,1,1,2,2,3,3-Heptafluoro-3-[(trifluorovinyl)oxy]propane
• Molecular Formula: C₅F₁₀O
• Molecular Weight: 266.04
• CAS Registry Number: 1623-05-8
• EC Number: 216-600-2
• SMILES: C(=C(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Melting point: -70 ºC (Expl.)
• Boiling point: 51.5±40.0 ºC 760 mmHg (Calc.)^*, 35 - 36 ºC (Expl.)
• Flash point: -10.2±23.2 ºC (Calc.)^*
• Index of refraction: 1.272 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H319
• Precautionary Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Flammable liquids	Flam. Liq.	1	H224
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Heptafluoropropyl trifluorovinyl ether is a fluorinated vinyl ether compound with the molecular formula C₅F₁₀O. Structurally, it consists of a trifluorovinyl group (–CF=CF₂) attached to an oxygen atom, which in turn is bonded to a heptafluoropropyl group (–CF₂CF₂CF₃). This compound belongs to the class of perfluorinated vinyl ethers and is known for its utility in advanced fluoropolymer synthesis due to its unique combination of chemical reactivity and stability.

The discovery and application of fluorinated vinyl ethers date back to developments in the mid-20th century when the demand for chemically resistant and thermally stable materials increased in industrial and aerospace sectors. Heptafluoropropyl trifluorovinyl ether emerged as one of the monomers suitable for copolymerization with tetrafluoroethylene (TFE) or other fluorinated olefins. The compound can be synthesized through etherification reactions that couple heptafluoropropanol or its derivatives with precursors containing the trifluorovinyl moiety. These reactions must be conducted under controlled conditions due to the high reactivity of the vinyl group and the sensitivity of fluorinated ethers to heat and light.

The trifluorovinyl group allows heptafluoropropyl trifluorovinyl ether to participate in radical polymerization processes, especially under the influence of initiators like peroxides or radiation. In copolymerization with TFE, it acts as a comonomer that imparts flexibility and improves the processability of the resulting fluoropolymer while retaining high chemical and thermal resistance. The resulting copolymers are used in a variety of high-performance applications, such as linings for pipes and tanks in corrosive chemical environments, components in semiconductor manufacturing equipment, and coatings for wire and cable insulation.

One notable application of this monomer is in the preparation of melt-processable perfluoropolymers. These materials maintain the favorable properties of polytetrafluoroethylene (PTFE)—including nonstick behavior, high dielectric strength, and chemical inertness—while being processable through conventional thermoplastic methods. Incorporation of heptafluoropropyl trifluorovinyl ether introduces branching or side chains that lower the crystallinity and melting point of the polymer, facilitating extrusion and molding.

In addition to industrial coatings and linings, fluoropolymers derived from this monomer are also used in gaskets, seals, and films for aerospace and automotive applications. The high density of fluorine atoms in the molecule results in low surface energy, making it highly repellent to oils, solvents, and water. This attribute also contributes to anti-fouling and easy-clean surface properties in commercial products.

Analytically, the identity and purity of heptafluoropropyl trifluorovinyl ether can be confirmed through ¹⁹F nuclear magnetic resonance (NMR) spectroscopy, which reveals distinct chemical shifts for the fluorine atoms in both the trifluorovinyl and heptafluoropropyl segments. Infrared (IR) spectroscopy shows characteristic absorption bands corresponding to C–F stretching and C=C double bonds. Gas chromatography coupled with mass spectrometry (GC-MS) is also used to monitor its purity and to detect any decomposition products.

From a safety perspective, the compound should be handled with care due to the presence of a reactive vinyl group and the potential formation of peroxides upon prolonged exposure to air and light. Appropriate storage in dark, cool, and inert conditions is recommended. Fluorinated vinyl ethers may release toxic decomposition products, including hydrogen fluoride (HF), when subjected to high temperatures or combustion, so proper ventilation and protective equipment are essential during processing.

In summary, heptafluoropropyl trifluorovinyl ether is a valuable fluorinated monomer used to produce high-performance fluoropolymers with improved thermal processability and chemical resistance. Its reactivity, combined with the advantageous properties of its perfluorinated groups, has made it an important building block in the field of specialty polymers for chemical processing, electronics, and advanced engineering materials.

References

2024. Wichtige Polymere durch Kettenwachstumspolymerisation. Polymere: Synthese, Eigenschaften und Anwendungen.
DOI: 10.1007/978-3-662-64601-4_14

2017. Fluorinated Candle Soot as the Lubricant Additive of Perfluoropolyether. Tribology Letters, 65(1).
DOI: 10.1007/s11249-017-0812-1

2016. Thermodynamic characteristics of the thermal polymerization of perfluoropropylvinyl ether at high pressures. Russian Journal of Physical Chemistry B, 10(4).
DOI: 10.1134/s1990793116040151