by Mesitylene, also known as 1,3,5-trimethylbenzene, is an organic compound that is used in various industrial applications. It has gained importance due to its uses in many different sectors. In this article, we will look at Mesitylene in detail including its properties, production, uses and health and environmental effects.
Properties of Mesitylene
Mesitylene is a clear, colorless liquid at room temperature with a sweet aromatic odor. Some key properties of Mesitylene include:
– Chemical Formula: C9H12
– Molecular Weight: 120.19 g/mol
– Melting Point: -45°C
– Boiling Point: 165°C
– Density: 0.86 g/cm3
– Solubility: Slightly soluble in water, soluble in organic solvents like ethanol and diethyl ether.
The molecular structure of Mesitylene consists of a benzene ring with three methyl substituents attached at the 1, 3, and 5 positions. This symmetric structure gives it higher stability and lower reactivity compared to other alkyl-substituted benzenes. Mesitylene is classified as a saturated hydrocarbon due to the absence of any double or triple carbon bonds.
Production of Mesitylene
Mesitylene can be produced through several chemical processes like aromatic substitution, catalytic reforming of petroleum products and methylation of toluene. However, the most common industrial production method involves catalytic alkylation of toluene with propylene:
Toluene + Propylene → Mesitylene
This reaction is catalyzed by acidic catalysts like aluminum chloride or zeolites. Commercially, the feedstocks used are crude C4 fractions from fluid catalytic cracking or pyrolysis gasoline, which are reacted with toluene in the presence of an acidic catalyst. The pure Mesitylene can be isolated through distillation. The worldwide production capacity for Mesitylene is estimated to be over 700,000 tons per year.
Uses of Mesitylene
Due to its unique structure and properties, Mesitylene finds applications in various fields as discussed below:
Intermediates in organic synthesis: Mesitylene and its derivatives are widely used as intermediates in organic synthesis to produce pharmaceuticals, agrochemicals, specialty chemicals and fine chemicals.
Solvents: Low toxicity and good solvent properties make Mesitylene suitable for use as a solvent in paints, coatings, adhesives, automotive fluids etc. It is used as an alternative to toluene in some applications.
Fuel blending: As a high-octane component, Mesitylene finds application in fuel blending to increase the octane rating of gasoline. It serves as a valuable blendstock in gasoline formulations.
Lubricant additives: Certain functionalized alkyl mesitylenes have shown potential as multifunctional lubricant additives providing benefits like improved viscosity properties.
Cosmetics: Ethoxylated mesitylene derivatives show emulsifying properties and are used as emulsifiers in cosmetic formulations like creams, lotions etc.
Other uses: Mesitylene also finds some minor uses as a fragrance ingredient in perfumes and as a chemical intermediate in production of dyes, pigments and engineering plastics.
Health and environmental effects
While Mesitylene has lower acute toxicity compared to benzene and toluene, it can be harmful if inhaled or ingested in large quantities. The following health effects are known:
– Skin and eye irritant
– Central nervous system depressant in high doses
– Possible carcinogen based on animal studies
– IARC groups it in Class 3 – not classifiable as to its carcinogenicity to humans.
Due to its volatility and solubility in water, Mesitylene can leach and contaminate surface and groundwater if released untreated into the environment from industrial waste streams. However, it is reported to biodegrade relatively fast in water and soil. Proper handling and treatment of wastes is necessary to prevent pollution issues.
Conclusion
In summary, Mesitylene is an important aromatic hydrocarbon that continues to witness steady growth in production and end use applications owing to its unique chemical properties. While handling and waste treatment need attention, it serves as a versatile building block in fine, specialty and agrochemical industries due to reactivity and high performance benefits. With new potential applications being discovered, the demand for Mesitylene is expected to rise further in the coming years.
*Note:
1.Source: Coherent Market Insights, Public sources, Desk research
2.We have leveraged AI tools to mine information and compile it
