Do You Know the Meaning of Anthracene?

Anthracene is a three-fused benzene ring solid polycyclic aromatic hydrocarbon (PAH) with the formula C14H10. It's a substance found in coal tar. Anthracene is used to make the red dye alizarin as well as other dyes. Anthracene is colourless but fluoresces blue (400–500 nm peak) when exposed to ultraviolet light.

This article will study the use of anthracene in detail.

Anthracene Sigma Aldrich

As we already studied anthracene meaning, let's discuss in detail about anthracene.

Three benzene rings are fused together to form anthracene, a polycyclic aromatic hydrocarbon. Sarah explains it simply: polycyclic refers to a molecule with more than one ring, aromatic refers to a molecule with alternating double-single bonds all over the ring structure, and hydrocarbon refers to a molecule composed entirely of carbon and hydrogen atoms.

Anthracene Sigma

The three rings that were bound together, as well as the network of alternating double and single bonds that ran all the way around them.

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Reactions of Anthracene

  1. Anthracene to Anthraquinone

Anthracene is converted to anthraquinone when it is reacted with an oxidising agent like hydrogen peroxide. Anthracene with two carbon-oxygen double bonds at the two middle carbons of the molecule is easily recognised as anthraquinone.

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  1. Methyl Anthracene

The Elbs reaction is an organic reaction in which an ortho methyl substituted benzophenone is pyrolyzed to produce a condensed polyaromatic. The reaction is named after Karl Elbs, a German chemist who also invented the Elbs oxidation. In 1884, the reaction was written. Elbs, on the other hand, misinterpreted the reaction product due to a lack of understanding of naphthalene structure.

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  1. Dibenzo Anthracene

The action of UV light causes anthracene to photo dimerize:

The [4+4] cycloaddition results in a pair of new carbon-carbon bonds connecting the dimer, which is known as dianthracene (or sometimes paranthracene). Thermally or with UV irradiation below 300 nm, it reverts to anthracene. The behaviour of substituted anthracene derivatives is similar. The presence of oxygen has an effect on the reaction.

  1. Magnesium Anthracene

Magnesium anthracene is an organomagnesium compound that is almost always isolated as a tetrahydrofuran (thf) adduct with three ligands. The air- and water-sensitive orange solid Mg(C14H10)(thf)3 is made by heating a suspension of magnesium in a thf solution of anthracene.

Use of Anthracene

  1. Anthracene is primarily converted to anthraquinone, a dye precursor.

  2. Anthracene, an organic semiconductor with a large band gap, is used as a scintillator for high-energy photon, electron, and alpha particle detectors. Plastics, such as polyvinyltoluene, can be doped with anthracene to create a water-equivalent plastic scintillator for use in radiation therapy dosimetry. The emission spectrum of anthracene peaks between 400 and 440 nm.

  3. Wood preservatives, insecticides, and coating materials all contain it.

  4. Anthracene is widely used as a UV tracer in printed wiring board conformal coatings. The anthracene tracer allows for UV inspection of the conformal coating. Anthracene is also used in anthraquinone use.

  5. Anthracene derivatives are used in a number of applications. 1-hydroxyanthracene and 2-hydroxyanthracene are hydroxylated derivatives of phenol and naphthols, and hydroxyanthracene (also known as anthrol and anthracenol) is pharmacologically active. 9,10-dihydroxyanthracene is an example of anthracene with several hydroxyl groups.

  6. During combustion processes, anthracene, like many other polycyclic aromatic hydrocarbons, is produced. Tobacco smoke and consumption of food tainted with combustion materials are the primary sources of human exposure.

  7. Anthracene is noncarcinogenic, according to several studies: "consistently negative results in numerous in vitro and in vivo genotoxicity experiments." Since crude samples were tainted with other polycyclic aromatic compounds, early studies suggested otherwise. It is also easily biodegradable in soil. In the presence of light, it is particularly vulnerable to deterioration.

Did you Know?

A polycyclic aromatic hydrocarbon (PAH) is a hydrocarbon with many aromatic rings, and is a chemical compound containing only carbon and hydrogen. The aromatic hydrocarbons are a significant subset of this category. Naphthalene, which has two aromatic rings, and the three-ring compounds anthracene and phenanthrene are the most basic of these chemicals. This principle is also known as polyaromatic hydrocarbon or polynuclear aromatic hydrocarbon. PAHs are non-polar, uncharged molecules with unique properties owing to delocalized electrons in their aromatic rings. Many are contained in coal and oil fields, as well as the thermal decomposition of organic matter in engines and incinerators, or when biomass burns in forest fires.

Polycyclic aromatic hydrocarbons are addressed as potential starting materials for abiotic synthesis of materials needed by life's earliest forms.

FAQs (Frequently Asked Questions)

1. Where do You Find Anthracene?

Ans: Vehicle exhaust gases, coal, coal tar, and hazardous waste sites have also been found to contain anthracene. These are all potential sources of contamination. Since anthracene has been discovered in cigarettes, you may be exposed by inhaling tobacco and cigarette smoke.

2. How do You Prepare Anthracene?

Ans: Anthracene is colourless, but when exposed to ultraviolet light, it fluoresces blue (400-500 nm peak). The cyclodehydration of o-methyl- or o-methyl-substituted diaryl ketones in the so-called Elbs reaction is a classic process for preparing anthracene in the laboratory.

3. Question: How do You Get Anthracene Out of Coal Tar?

Ans: A high-boiling coal-tar fraction crystallises crude anthracene. Recrystallization and sublimation are used to purify it. Anthraquinone is produced by oxidation and is used as an intermediate in the manufacture of dyes and pigments.