Mesitylene, also known as 1,3,5-trimethylbenzene, is an organic compound with the formula C9H12. It is a colorless liquid that is slightly denser than water and has a sharp, sweet odor. Some key physical and chemical properties of 1,3,5-trimethylbenzene include:
- Molecular formula: C9H12
- Molecular weight: 120.19 g/mol
- Melting point: -46 °C (-51 °F)
- Boiling point: 165 °C (329 °F)
- Density: 0.86 g/cm3 (liquid), 0.869 g/cm3 (solid) at 20°C
- Solubility: Slightly soluble in water, miscible with organic solvents
- Vapor pressure: 1.13 kPa at 20°C
- Flash point: 45 °C (113 °F)
1,3,5-trimethylbenzene is classified as an aromatic hydrocarbon as it contains a benzene ring with three methyl substitutions. It exhibits limited solubility in water but is miscible with common organic solvents such as alcohols, ethers, and hydrocarbons. Due to its low melting and boiling points, 1,3,5-trimethylbenzene remains a liquid under normal conditions.
Synthesis and Industrial Production of Mesitylene
Industrially, 1,3,5-trimethylbenzene is produced predominantly as a byproduct during the catalytic reformating of petroleum naphthas or catalytic crackers. In catalytic reforming, the feedstock is treated with a platinum catalyst to produce 1,3,5-trimethylbenzene along with other aromatic compounds. Alternatively, it can be synthesized via Friedel-Crafts alkylation, where toluene reacts with propene over an aluminum chloride catalyst.
The global production capacity for 1,3,5-trimethylbenzene exceeds 1.2 million metric tons annually. The United States, China, and Middle Eastern nations are among the top producers worldwide. Following synthesis, 1,3,5-trimethylbenzene undergoes purification using techniques like distillation to obtain high-purity 1,3,5-trimethylbenzene suitable for industrial applications.
Applications of Mesitylene in Chemistry and Industries
Due to its aromatic structure, 1,3,5-trimethylbenzene finds a variety of uses in chemical industries and downstream applications:
- Solvent in paints, coatings, and adhesives: 1,3,5-trimethylbenzene acts as a good thinning agent and solvent due to its low volatility, Mesitylene toxicity and odor. It improves the application and performance of paints, varnishes and glues.
- Extractant in fragrance and flavor industry: The sweet aroma of 1,3,5-trimethylbenzene makes it useful for extracting fragrance and essential oils from plants. It is used as a solvent in perfumes, soaps and flavor formulations.
- Intermediate in organic synthesis: Reactions like Friedel-Crafts acylation, formylation and methylation yield valuable aromatic compounds using 1,3,5-trimethylbenzene as the intermediate. These derivatives see application as dyes, drugs and agrochemicals.
- Fuel blending: Certain fuel oxygenates and methyl-tert-butyl ether (MTBE) use 1,3,5-trimethylbenzene during their production. Its high octane rating makes it suitable as a gasoline blending component.
- Other uses: Minor applications include 1,3,5-trimethylbenzene as a laboratory reagent, corrosion inhibitor, and as a starting material in rubber chemicals and surfactant manufacturing.
Outlook for the Use of Mesitylene
With rapidly expanding global demand for chemicals, many of the industries employing 1,3,5-trimethylbenzene are forecasted to grow in the coming years. Due to its diverse functionalities, 1,3,5-trimethylbenzene consumption is projected to rise by 3-4% annually to support growing end-use markets. While petroleum-based production currently dominates, new biosynthetic methods may provide more sustainable routes. Overall, mesitylene will likely maintain its importance as a key aromatic building block with broad industrial applications. Tightening regulations may spur the development of low-emission production technologies and safer alternatives to traditional solvent uses.
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