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
• Article Data: 5

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

Perfluorotripropylamine is a reagent used in the surface modification of droplet polymeric microfluidic devices. This is used to improve the stable and continueous generation of aqueous droplets.

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.

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.

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.