What is Furfural? - Uses, Structure & Production

Instructor: Korry Barnes

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

In this lesson, we will be discussing an organic compound called furfural. The specifics we will be exploring the structure of furfural, how it is produced both on small laboratory scales and industrially, and finally what it can be used for in terms of applications.

Where Do We Get That From?

Have you ever wondered where a lot of our chemical feedstocks come from? What we are referring to by 'feedstocks' is raw materials that can be used to manufacture chemicals that are important to the chemical industry and things we rely on daily for our lives. Obviously, we don't just get these raw materials out of thin air so where do they come from? Well, most raw materials we rely on actually come from petroleum-based sources. As you're probably aware, petroleum is a yellow-black liquid found beneath the earth's surface that contains various organic compounds (carbon-based compounds) that can be separated from one another into feedstocks that can be used by chemists for other chemicals.

Petroleum sources aren't going to last forever, and so there's been a big push recently for scientists to come up with alternative sources of fuel and feedstocks that aren't reliant on petroleum. In this lesson, we are going to be learning about an organic compound called furfural, which is considered a renewable chemical feedstock that's non-petroleum based (meaning it doesn't come from petroleum sources). Our main topics of discussion will be the structure of furfural, how it's made in terms of production, and finally some of the more important uses in which it finds application.

Structure of Furfural

Let's get started by looking at the structure of furfural. Furfural is an aldehyde of furan and is a yellow oily liquid in pure form, but tends to turn brown upon prolonged exposure to air and moisture. An aldehyde is an organic functional group that has a carbonyl group (carbon-oxygen double bond) attached to a hydrogen and some other carbon-based side chain. Furan is an aromatic five-membered ring that has an oxygen atom embedded within the ring system. Notice that the aldehyde portion of the molecule is bonded to the carbon that's directly adjacent to the oxygen of the furan ring.

Structure of furfural

Due to the polar nature of furfural, it will dissolve quite readily and form solutions with a variety of polar organic solvents like methanol, ethanol, chloroform, and dimethyl sulfoxide (DMSO). It will not, however, dissolve in water and particularly non-polar solvents like hexane.

Production of Furfural

We mentioned previously that furfural was a renewable chemical feedstock. The reason this is the case actually stems from how it's made. Furfural can be produced on large industrial scales by taking plant mass and treating it with an acid. When this happens, the 5-carbon sugar molecules undergo a dehydration (loss of water) reaction to give furfural.

Depending on the type of plant matter that's used, anywhere between 3% and 10% of the original plant mass can be recovered as furfural. Obviously, plants are constantly growing and being produced, that's why furfural is considered a 'green' or renewable source of chemical feedstocks. It could potentially represent an important source of organic compounds once petroleum resources start to dry up.

Uses of Furfural

Now that we know what the structure of furfural looks like and how it's produced, let's talk about a couple of the more important applications it can be utilized for. If we take furfural and convert the aldehyde to an alcohol in what's called a reduction reaction, we get furfuryl alcohol (abbreviated FA). FA is used in the manufacture of things like cement, adhesives, castings, and coatings.

Reduction of furfural to give furfuryl alcohol

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