Anthracene: Hazards & Uses

Instructor: Korry Barnes

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

The focus of this lesson will be on an organic molecule known as anthracene. Our main points of exploration will be on its structure, reactions it undergoes, uses, and hazards.

Learning about Aromatic Compounds

Luke is currently in his second semester of organic chemistry, and the class has been going over the chapter dealing with aromatic compounds. Yesterday, they spent the entire lecture talking and learning about a specific aromatic compound called anthracene. Luke left the lecture feeling down, as he found most of the information the professor covered to be very confusing and he felt like he didn't understand very much.

Fortunately for Luke, his good friend Sarah has already finished organic chemistry and has agreed to tutor him and bring him up to speed on anthracene so he can feel more confident moving forward in the material. Have you ever heard of or are you familiar with anthracene? Let's sit in on their tutoring session and learn side-by-side with Luke about this particular compound!

Structure of Anthracene

Sarah starts things off by going over the structure of anthracene with Luke, since having a basic understanding of anthracene and being able to recognize it is the first thing we must be comfortable with. Anthracene is a polycyclic aromatic hydrocarbon that has three benzene rings fused together. Sarah breaks it down very simply: polycyclic means more than one ring, aromatic means the molecule has alternating double-single bonds all around the ring system, and hydrocarbon means it's only made of carbon and hydrogen atoms.

Structure of anthracene

Once she broke down the components of the description of anthracene, Luke was able to see clearly what Sarah meant. He noticed the three rings that are joined together, and he also realized that there is a network of alternating double and single bonds all around the three rings.

Reactions of Anthracene

Now that Luke knows what anthracene is and how to recognize it, Sarah begins to teach him about a couple of the chemical reactions it can undergo.

Dimerization of Anthracene

If we take anthracene and expose it to ultra-violet light, it will actually undergo what's called a dimerization reaction. This is when two molecules of anthracene combine with one another to form an even larger hydrocarbon structure. Sarah teaches Luke that the prefix di- in dimerization means 'two' (e.g. two molecules of anthracene) so this reaction is easy to recognize.

In terms of usefulness, compounds such as anthracene dimers and other polycyclic aromatic hydrocarbons play in important role in organic semi-conductors. Additionally, they have received considerable attention from researchers for their application as organic materials that can serve in solar panels to harness the energy of the sun.

Oxidation of Anthracene

If anthracene is reacted with an oxidizing agent, such as hydrogen peroxide, the product we get is anthraquinone. Anthraquinone is easy to recognize; it's just anthracene with two carbon-oxygen double bonds at the two middle carbons of the molecule.

Structure of anthraquinone, the oxidized version of anthracene

Uses of Anthracene

The next thing Sarah is teaching us about are some of the practical uses of anthracene. That way it doesn't just seem like an abstract molecule with no value or application. Some of the most common applications of anthracene include use as a preservative in wood and lumber and use as an insecticide for crops.

In terms of the oxidation reaction we just mentioned above, the product anthraquinone is actually used as a building block for a lot of dyes that the fabrics and textile industries rely on for the bright and vibrant colors they use. Luke asks if that's relevant, since it's not anthracene itself that is used, but Sarah is quick to point out that although that's true, anthraquinone is derived directly from anthracene, so it definitely plays an important role. Alizarin is an anthraquinone-dye that's a beautiful red colored dye.

Alizarin powder sample

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