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Overview

2,2,2-Trifluoroethanol (TFE)

Trifluoroethanol, CF3CH2OH, was first prepared in 1933. This colorless liquid with an ethanol-like odor has a number of unique properties. The three fluorines give the alcohol a high ionization constant and very strong hydrogen bonding capability, which make it a very unusual solvent. The fluorines also make the molecule very stable at high temperatures. These properties have put trifluoroethanol (TFE) to use in some special applications in addition to its use in pharmaceutical and agricultural chemical syntheses.

In 1960, Halocarbon Life Sciences was the world’s first commercial producer of TFE. Today, with our state-of-the-art plant in North Augusta, South Carolina, we continue in the forefront supplying this important and interesting compound.

Key Features

• High ionization constant
• Very strong hydrogen bonding capability
• Stable at high temperatures
• Dissolves nylons at room temperature

Suitable for

• Common metals, including carbon steel

Resistant to

• Common metals, including carbon steel
Molecular Weight 100.04
Boiling Point 73.5°C
Melting Point -45°C
Flash Point Open Cup 105°F
Flash Point Closed Cup 86°F
Fire Point None
Density (25°C) 1.382 g/cc
Refractive Index 1.2907 n20/d
Critical Temperature 227°C
Critical Pressure 715 psia
Heat of Vaporization 149 Btu/lb
Heat of Combustion -211.9 kcal/mol
Vapor Pressure vs Temperature (mm Hg & K) log P = -1910/T + 8.39
Thermal Conductivity (104°F) 0.071 Btu/hr ft
Viscosity (100°F) 0.90 centistrokes
Ionization Constant (Ka) 4.3 x 10-13
Dipole Moment (25°C) 2.03 D
Dielectric Constant (25°C) 26.14

Toxicity
TFE is toxic in rats when ingested orally (acute oral LD50: 240 mg/Kg). It causes severe eye damage similar to isopropyl alcohol and toluene. Special precautions must be taken when handling TFE. Subchronic inhalation exposure (150 ppm TFE for 6 hours per day, 5 days per week for 4 weeks) of male rats caused testicular depression leading to infertility lasting for at least 5 weeks after exposure. Similar exposure to 10 ppm had no effect and exposure to 50 ppm had a transient effect. While the significance of these observations for human safety is unknown, it is recommended that the concentration of TFE vapor in the atmosphere be kept below 5 ppm. A Material Safety Data Sheet providing safety and toxicity information for TFE will be furnished upon request. The information given here is intended for general reference only.

Flammability
TFE has flash points of 86°F (Pensky Martin Closed Cup) and 105 °F (Cleveland Open Cup). It is classified as a flammable liquid according to U.S. DOT regulations. However, it will not sustain its own flame because of its low heat of combustion and therefore has no fire point.

Materials of Construction
TFE does not present any special corrosion problems with common metals and can be handled in carbon steel.

Packaging
TFE is available from Halocarbon in one-gallon cans, 55-pound carboys and 600-pound drums. Larger containers can be available upon request.

Applications

Pharmaceutical Uses
TFE is the major raw material for three inhalation anesthetics: isoflurane, CF3CClHOCF2H; desflurane, CF3CFHOCF2H; and fluroxene, CF3CH2OCH=CH2. While fluroxene is no longer used, it was the first low flammability anesthetic used to replace ether. Both isoflurane and desflurane are currently in wide use.

Solvent for Nylon
The solubility of nylons in TFE is used to join matching surfaces of solid nylon parts. If both surfaces are wetted with TFE and then fitted together, a permanent joint will be made. This technique is used commercially to manufacture pollution control valves for automobiles. TFE’s nylon solubility is also used to make nonfraying ends for nylon rope and solutions for quality control of nylon production. Nylon solutions in TFE can be used as vehicles for adhesives, pigments, metal powders or dyes. These mixtures yield nylon-toughened adhesives or deposit tough surface coatings.

Other Uses
The trifluoroethoxy group in place of the ethoxy group in a dye produces a different color. TFE is also useful as a solvent to increase the quantum yields of fluorescing dyes in lasers. TFE-water mixtures are solvents for both salts and organic molecules. These materials can be brought together in solutions to probe the mechanisms of reactions. TFE’s combination of low nucleophilicity, basicity and higher ionizing power than alcohols like methanol and ethanol makes it especially useful for such studies. The low specific conductance of TFE compared to solvents such as formic and acetic acids allows ionic reactions to be monitored by conductometric measurements. It is also useful as a solvent for acid-sensitive substrates. The products made from TFE have many, and frequently unpredictable.

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