by Introduction
Mesitylene, also known as 1,3,5-trimethylbenzene, is an organic compound that consists of a benzene ring substituted with three methyl groups. While it may sound like an obscure chemical, Mesitylene plays an important role in industrial processes and research due its unique properties and reactivity. In this article, we will explore what Mesitylene is, how it is produced, its applications, and the future potential of this versatile chemical building block.
Chemical Properties and Structure
Mesitylene derives its name from Greek word “mesityl” which means “middle”. The positions of the three methyl groups on the benzene ring give Mesitylene high symmetry and stability. Chemically, it is classified as an aromatic hydrocarbon and falls under the category of trimethylbenzenes. The three methyl substitutions make Mesitylene non-planar and less reactive compared to benzene. However, due to its rigidity and stability, Mesitylene tends to retain its structure even under high reaction temperatures and pressures. These properties make it suitable for use as a starting material and intermediate in industrial processes.
Production
Industrially, Mesitylene is produced through catalytic reformatting of petroleum fractions obtained during crude oil refining. In this process, linear hydrocarbons are transformed into aromatic compounds through dehydrogenation and isomerization reactions over acidic catalysts like platinum or aluminium chloride. Majority of Mesitylene production occurs in oil refineries associated with chemical plants. Typical annual global production capacity is estimated to be several hundred thousand tons. It can also be synthesized through Friedel-Crafts alkylation of toluene with propene though this route is not economically viable at large scales.
Applications
Lubricant Production
A significant portion of the Mesitylene produced is consumed in the manufacturing of specialty synthetic lubricant additives. During alkylation, Mesitylene reacts with olefin polymers to introduce branching and impart desirable rheological properties to lubricants. Its three methyl groups allow for uniform branching that enhances lubricity and viscosity index of finished lubricant formulations.
Fragrance Chemicals
Some key fragrance chemicals derived from Mesitylene include musk xylene and musk ketone. These compounds have pleasant, long-lasting odors and are widely used in fine fragrances, soaps, cosmetics and household products. Musk xylene in particular imparts a sweet, woody aroma and remains an important natural musk substitute in perfumery.
Pharmaceutical Intermediate
Being an aromatic precursor, Mesitylene finds application as a starting material in the production of bulk and fine pharmaceutical actives. It can undergo nitration, halogenation, sulfonation and other substitution reactions to synthesize pharmaceutical intermediates like mesitylene sulfonic acid and its derivatives. These Mesitylene-derived compounds are building blocks for a variety of drug molecules across therapeutic classes.
Laboratory Reagent
Due to the stability and structural properties imparted by its multiple methyl groups, Mesitylene is utilized as a non-polar, inert solvent in organic synthesis and analytical chemistry. It has low volatility and solubilizes a wide range of organic compounds without undergoing undesirable side reactions. Mesitylene remains a preferred laboratory-grade hydrocarbon reagent.
Emerging Applications
Fuel Additive
With stringent fuel efficiency and emission norms, researchers are exploring Mesitylene and its derivatives as potential gasoline octane improvers and combustion modifying additives. Early studies indicate Mesitylene may enhance fuel ignition quality and oxygen content while reducing particulate emissions from engines when blended in small amounts. Further development could see Mesitylene feature more prominently in next-gen fuel formulations.
Lithium-ion Battery Technology
Mesitylene is being investigated for applications in lithium-ion batteries due to favourable electrochemical properties. When converted to a thin solid electrolyte interface layer between electrodes, Mesitylene and its polymers are found to improve lithium ion conductivity and suppress dendrite growth. This could lead to batteries with longer cycle life, higher power density and enhanced safety. Mesitylene may enable new lithium metal technologies.
Conclusion
Though often overlooked, Mesitylene forms the basis of numerous formulations across heavy industry segments as well as our daily consumer products. With unique three-dimensional structure and derived functionalities, it continues to attract interest from R&D. Future potential lies in refining Mesitylene-based materials for energy storage, sustainable fuels and new drug synthesis routes. As research advances applications, Mesitylene can be expected to remain a workhorse chemical with a versatile multipurpose role in the industry.
*Note:
1.Source: Coherent Market Insights, Public sources, Desk research
2.We have leveraged AI tools to mine information and compile it
