What is THF (Tetrahydrofuran)? - Structure, Uses & Hazards

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

In this lesson we will be discussing an important organic compound called tetrahydrofuran, which is primarily utilized as an organic solvent. We will talk about some of it uses and hazards as well.

Good Compounds with a Bad Rap

When most people hear the term 'organic solvent' they might immediately associate words like 'toxic', 'bad for the environment', 'causes cancer', 'dangerous', etc. Although it's true that organic solvents can be all those things, what's important to realize is that without them, a lot of the things we depend on for our daily lives simply wouldn't be possible.

An organic solvent is a carbon and hydrogen-based (organic) substance that can serve to form a solution of some sort (solvent).

The list of organic solvents is quite extensive, but today let's focus on a specific solvent called tetrahydrofuran or THF for short. THF is a solvent that contains carbon, hydrogen, and one oxygen atom.

Although it certainly has its drawbacks and limitations, what we will see is that, like any organic solvent, it serves an important purpose. If used and handled correctly, it can be a powerful tool for the organic chemist to have at his or her disposal. Let's explore THF in terms of structure, primary applications for use, and the hazards associated with it.

Structure of THF

THF is composed of 4 carbon atoms, 8 hydrogen atoms, and one oxygen atom. It is most importantly characterized as being a heterocyclic ether. '-Cyclic' means it's a ring structure, the prefix 'hetero-' tells us that at least one of the atoms within the ring is something other than carbon (oxygen in this case), and the 'ether' portion of the name tells us the functional group. An ether is an organic functional group in which a central oxygen atom is bonded to two carbon-based groups.

What about the '-furan' portion of the name tetrahydrofuran? This tells us that it's a derivative or 'cousin' of its parent molecule, furan. THF only differs in the fact that the double bonds have been removed and replaced with 4 hydrogen atoms. Does the term 'tetra' mean anything to you? That's right it means 4, for the 4 hydrogen atoms that have been added!

Structures of Furan and tetrahydrofuran (THF). THF has 4 hydrogen atoms replacing the double bonds of furan.

Another important structural aspect of THF is that it is a polar molecule. Since oxygen is more electronegative than carbon and hydrogen, the oxygen pulls electron density towards itself in the form of the covalent bonds within the ring structure. As a consequence of its polarity, THF mixes readily with other polar species like water, methanol, ethanol, and acetonitrile, just to name a few.

Uses of THF

Let's take a look at a couple of the more common applications THF can serve.

Use as a Solvent

Probably one of the most common applications is as a solvent. A solvent is used to create solutions, and in this case THF serves to dissolve or form solutions with other organic compounds. In the chemical industry, THF is the solvent of choice in making polyvinyl chloride (PVC), which is the plastic that a lot of our indoor plumbing and sprinkler system pipes are made out of.

THF is the solvent used in the synthesis of PVC pipes, which are commonly found in household plumbing systems

THF is also a popular solvent choice for small-scale laboratory experiments, mainly because it can dissolve a wide variety of organic compounds and has a relatively low boiling point. The low boiling point is convenient because it makes the solvent easy to remove from the chemical reaction by evaporation.

Polymerization Applications

It turns out that if you take THF and expose it to a strong acid, it will polymerize (form a repeating network of THF molecules) into what's called poly(tetramethylene ether) glycol or PTMEG for short. That's a long, complicated name, but PTMEG is the polymer used for making something a lot of use daily, spandex!

THF will polymerize when treated with strong acid to form PTMEG, a polymer used for making spandex

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