Perfluorotributylamine (PFTBA), also referred to as FC43, is a colorless liquid with the formula N(C₄F₉)₃. The compound consists of three

butyl In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, gi ...

groups connected to an

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...

center, in which all of the hydrogen atoms have been replaced with

fluorine Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reacti ...

. The compound is produced for the electronics industry, along with other perfluoroalkylamines. The high degree of fluorination significantly reduces the basicity of the central amine due to electron-withdrawing effects.

Preparation

It is prepared by electrofluorination of

tributylamine Tributylamine (TBA) is an organic compound with the molecular formula (C4H9)3N. It is a colorless liquid with an amine-like odor. Uses Tributylamine is used as a catalyst (proton acceptor) and as a solvent in organic syntheses and polymerization ...

using

hydrogen fluoride Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock i ...

as solvent and source of fluorine: :N(C₄H₉)₃ + 27 HF → N(C₄F₉)₃ + 27 H₂

Uses

The compound has two commercial uses. It is used as an ingredient in

Fluosol A blood substitute (also called artificial blood or blood surrogate) is a substance used to mimic and fulfill some functions of biological blood. It aims to provide an alternative to blood transfusion, which is transferring blood or blood-based ...

, artificial blood. This application exploits the high solubility of oxygen and carbon dioxide in the solvent, as well as the low viscosity and toxicity. It is also a component of

Fluorinert Fluorinert is the trademarked brand name for the line of electronics coolant liquids sold commercially by 3M. As perfluorinated compounds (PFCs), all Fluorinert variants have an extremely high Global Warming Potential (GWP), so should be used wit ...

coolant liquids. CPUs of some computers are immersed in this liquid to facilitate cooling.

Niche

The compound is used as a calibrant in gas chromatography when the

analytical technique Analytical technique is a method used to determine a chemical or physical property of a chemical substance, chemical element, or mixture. There is a wide variety of techniques used for analysis, from simple weighing to advanced techniques using high ...

uses

mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is use ...

as a detector to identify and quantify chemical compounds in gases or liquids. When undergoing ionization in the mass spectrometer, the compound decomposes in a repeatable pattern to form fragments of specific masses, which can be used to tune the mass response and accuracy of the mass spectrometer. Most commonly used ions are those with approximate mass of 69, 131, 219, 414 and 502 atomic mass units.

Safety

Fluorofluids are generally of very low toxicity, so much that they have been evaluated as synthetic blood.

Environmental impact

It is a

greenhouse gas A greenhouse gas (GHG or GhG) is a gas that Absorption (electromagnetic radiation), absorbs and Emission (electromagnetic radiation), emits radiant energy within the thermal infrared range, causing the greenhouse effect. The primary greenhouse ...

with warming properties more than 7,000 times that of

carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...

over a 100-year period, and, as such, is the most potent greenhouse gas ever discovered. Its concentration in the atmosphere is approximately 0.18 parts per trillion. The compound can persist in the atmosphere for up to 500 years.

Sulfur hexafluoride Sulfur hexafluoride or sulphur hexafluoride (British spelling) is an inorganic compound with the formula SF6. It is a colorless, odorless, non- flammable, and non-toxic gas. has an octahedral geometry, consisting of six fluorine atoms attached ...

, however, has a GWP of 23,900, which would make it much more powerful. File:Perfluorotributylamine-global-warming-potential.jpg ,

Global warming potential Global warming potential (GWP) is the heat absorbed by any greenhouse gas in the atmosphere, as a multiple of the heat that would be absorbed by the same mass of carbon dioxide (). GWP is 1 for . For other gases it depends on the gas and the time ...

of greenhouse gases and PFTBA

References