338-83-0

Basic information

• Product Name: Perfluorotripropylamine
• Synonyms: tris-heptafluoropropyl-amine;Perfluoro-tri-n-propylamine;Perfluorotripropylamine 90%;Perfluorotripropylamine90%;FC-3283;FTPA;Perfluoropropylamine;Tri(heptafluoropropyl)amine
• CAS NO: 338-83-0
• Molecular Formula: C₉F₂₁N
• Molecular Weight: 521.07
• EINECS: 206-420-2
• Mol File: 338-83-0.mol

Chemical Properties

• Melting Point: -52 °C
• Boiling Point: 125-135°C
• Flash Point: 32.4 °C
• Appearance: /
• Density: 1.82
• Vapor Pressure: 9.91mmHg at 25°C
• Refractive Index: 1.279
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: -27.02±0.50(Predicted)
• CAS DataBase Reference: Perfluorotripropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Perfluorotripropylamine(338-83-0)
• EPA Substance Registry System: Perfluorotripropylamine(338-83-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• TSCA: T
• Hazardous Substances Data: 338-83-0(Hazardous Substances Data)

Usage

Uses

Used in Microfluidics:
Perfluorotripropylamine is used as a reagent for surface modification in droplet polymeric microfluidic devices. Its application is crucial for improving the stable and continuous generation of aqueous droplets, which is essential for the efficient functioning of microfluidic systems.
Used in Surface Coating Industry:
Perfluorotripropylamine is used as a surface-active agent in the development of coatings with enhanced properties. Its low surface tension and chemical resistance contribute to the formation of uniform and durable coatings, which are particularly useful in applications requiring non-stick, anti-fouling, or easy-to-clean surfaces.
Used in Chemical Synthesis:
Perfluorotripropylamine serves as an intermediate or reactant in the synthesis of various perfluorinated compounds. Its unique structure and reactivity make it a valuable building block for the development of specialty chemicals, pharmaceuticals, and materials with tailored properties.
Used in Electronics Industry:
Perfluorotripropylamine is utilized as a component in the fabrication of electronic devices, particularly in the development of high-performance lubricants and thermal interface materials. Its thermal stability and resistance to degradation contribute to the reliable operation and longevity of electronic components.
Used in Environmental Remediation:
Perfluorotripropylamine is employed in the treatment of contaminated water and soil, where its chemical properties enable the efficient removal of pollutants and the decontamination of affected environments. Its resistance to degradation and low toxicity make it a suitable candidate for environmental applications.

Purification Methods

Purify it as for perfluorodimethyl-cyclopropane (see p 220). [Haszeldine J Chem Soc 102 1951, for azeotropes see Simons & Linevsky J Am Chem Soc 74 4750 1972.] IRRITANT.

Synthetic route

tri-n-propylamine (102-69-2) → Perfluorotripropylamine (338-83-0)

Conditions	Yield
With fluorine; sodium fluoride In 1,1,2-Trichloro-1,2,2-trifluoroethane at 10℃; for 5h;	72.5%
With hydrogen fluoride at -4 - 19℃; Product distribution; Electrochemical fluorination. Var. temp., voltage, init conc. of amine, stirring effect investigated.;
With cobalt (III) fluoride at 300℃;

tri-n-propylamine (102-69-2) → Perfluorotripropylamine (338-83-0) + N-(F-propyl)-2-(F-ethyl)-F-pyrrolidine (97147-06-3)

Conditions	Yield
With hydrogen fluoride at 3 - 6℃; for 52h; electrochemical fluorination;	A 20.1% B 2.1%

perfluoropropylene (116-15-4) + di-n-propylamine (142-84-7) → Perfluorotripropylamine (338-83-0) + N-(F-propyl)-2-(F-ethyl)-F-pyrrolidine (97147-06-3)

Conditions	Yield
With hydrogen fluoride 1.) ether, room temperature, overnight, 2.) electrochemical fluorination, 3-6 deg C, 52 h; Yield given. Multistep reaction. Yields of byproduct given;

heptafluoropropyl-bis-(1,2,2,3,3,3-hexafluoro-propyl)-amine → carbon tetrafluoride (75-73-0) + freon-218 (76-19-7) + Hexafluoroethane (76-16-4) + Perfluorotripropylamine (338-83-0)

Conditions	Yield
With fluorine at 280 - 390℃; for 0.1h; Fluorination; Title compound not separated from byproducts;
With fluorine at 100 - 170℃; for 17h; Product distribution; Further Variations:; Temperatures; time; Fluorination;

tri-n-propylamine (102-69-2) + nitrogen + cobalt (III)-fluoride → Perfluorotripropylamine (338-83-0)

Conditions	Yield
at 300℃;

tri-n-propylamine (102-69-2) → freon-218 (76-19-7) + Perfluorotripropylamine (338-83-0) + F-(N-F-Fluoro,N,N-di-n-propylamine) (1554-24-1) + 2,3,3,4,4,5-hexafluoro-1,2-bis-pentafluoroethyl-5-trifluoromethyl-pyrrolidine

Conditions	Yield
With hydrogen fluoride Product distribution; Further Variations:; current density; Electrochemical reaction;

Triallylamine (102-70-5) + toluene (108-88-3) → perfluoro-(N-propyl-3,4-dimethylpyrrolidine) (413579-52-9) + Perfluorotripropylamine (338-83-0) + perfluoro-(N-propyl-3-methylpiperidine) (96009-90-4) + perfluoro-(1,2-dimethylcyclopentane) + perfluoro-(1,1-dimethylcyclopentane) + perfluoro-(ethylcyclopentane)

Conditions	Yield
With hydrogen fluoride Electrochemical reaction; Further byproducts. Title compound not separated from byproducts.;

tri-n-propylamine (102-69-2) + hydrogen fluoride (7664-39-3) → Perfluorotripropylamine (338-83-0)

Conditions	Yield
In hydrogen fluoride HF (liquid); Electrochem. Process; electrofluorination, 4-8 V, 200 A/m2, Ni anode, Fe cathode;

tri-n-propylamine (102-69-2) + cobalt(III) fluoride (10026-18-3) → Perfluorotripropylamine (338-83-0)

Perfluorotripropylamine (338-83-0) → difluoromethylene-heptafluoropropyl-amine (378-00-7)

Conditions	Yield
pyrolysis at 660-670°C in graphite tube;	82%
pyrolysis at 660-670°C;	73%
pyrolysis at 660-670°C in presence of AlF3;	>99

Perfluorotripropylamine (338-83-0) → 2,2,3,3,3-pentafluoro-N-(perfluoropropyl)propanimidoyl fluoride (356-64-9)

Conditions	Yield
With antimony pentafluoride at 70 - 110℃; for 3h;	63%
passing through a graphite tube filled with AlF3-Al2O3, at 500-550°C;
With β-Al2O3/AlF3 at 550℃;

Perfluorotripropylamine (338-83-0) → perfluoro(2-aza-2-pentene) (680-23-9)

Conditions	Yield
at 650℃;	15.6 g

Perfluorotripropylamine (338-83-0) + o-carborane → 3,3,3-trifluoro-2,2-difluoropropylamide of perfluorobutanoic acid + 8,9,10,12-tetrafluoro-o-carborane

Conditions	Yield
With water; antimony pentafluoride 1.) 70 deg C, 10 h; Yield given. Multistep reaction;

Upstream product

• 102-69-2 tri-n-propylamine 
• 116-15-4 perfluoropropylene 
• 142-84-7 di-n-propylamine 
• 102-70-5 Triallylamine 
• 108-88-3 toluene 
• 7664-39-3 hydrogen fluoride 
• 10026-18-3 cobalt(III) fluoride 

Relevant articles and documents

CORRELATION BETWEEN YIELD AND OPERATING CONDITIONS IN THE ELECTROCHEMICAL FLUORINATION OF TRIPROPYLAMINE

Electrochemical fluorination of tripropylamine in anhydrous hydrogen fluoride was studied in order to verify the correlation between the operating conditions and the yield of the corresponding perfluoroamine.The parameters tested were: temperature, voltage, initial concentration of amine in the bath, constant concentration of amine in the bath and stirring effect.Experimental data show that temperature is the parameter exerting the most remarkable influence over perfluoroamine yield and by-products formation.

Electrochemical fluorination of toluene and benzotrifluoride in the presence of triallylamine

Electrochemical fluorination of benzotrifluoride in the presence of triallylamine as depolarizer was studied. The possibility of preparing perfluoromethylcyclohexane and its isomers with high current efficiency and substance yield in combination with perfluorinated tertiary amines was examined.

An efficient high-yield synthesis for perfluorinated tertiary alkyl amines

We wish to report a high-yield synthesis of perfluorinated tertiary amines from their hydrocarbon analogues by direct fluorination. Yields up to 70%, with high purities, have been obtained from certain tertiary amines. This technique will likely develop into a new general method for producing perfluorinated amines.

Cleavage path way and the product distribution pattern during the electrochemical perfluorination of tripropylamine

The electrochemical fluorination (ECF) of tripropylamine (TPA) was carried out in anhydrous hydrogen fluoride medium using a Simons type cell. Under optimum conditions, yield of perfluorinated product was about 51% and the selectivity of perfluorotripropy

Technology for the preparation of perfluoro-organic compounds

Fluorination by elemental fluorine of fluorine-containing alkenes, alkanes, ethers and tertiary amines was investigated, aimed at obtaining the perfluorinated analogs. The factors affecting yield of the target compounds were studied. Elements of technology were elucidated.