Mesitylene, also known as 1,3,5-trimethylbenzene, is a clear, colorless liquid at room temperature with a distinctive odor. Some of its key physical and chemical properties include:

- Molecular formula: C9H12
- Molar mass: 120.19 g/mol
- Melting point: -48°C
- Boiling point: 165°C
- Density: 0.862 g/cm3 at 25°C
- Solubility: Practically insoluble in water, miscible with most organic solvents
- Vapor pressure: 1.3 kPa at 25°C
- Flash point: 49°C
- Autoignition temperature: 410°C

As an aromatic hydrocarbon, 1,3,5-trimethylbenzene contains a benzene ring with three methyl substituents. This makes it significantly more stable than benzene and less reactive. However, it can still undergo electrophilic aromatic substitution reactions when treated with strong acids, bases, or oxidizing agents. The methyl groups also impart increased hydrophobicity compared to benzene.

Production and Applications of Mesitylene

Most 1,3,5-trimethylbenzene is produced as a byproduct during the methylation of toluene to produce xylene isomers, Mesitylene which are important intermediates in the production of many petrochemicals and polymers. In the methylation reaction, toluene reacts with methanol in the presence of an acid catalyst to yield a mixture of xylene isomers and trimethylbenzenes including 1,3,5-trimethylbenzene.

1,3,5-trimethylbenzene finds several important uses due to its unique physical and chemical properties. One major application is as a precursor in the production of various lubricant additives. Specifically, chloromesytilenes are reacted with alcohols or amines to synthesize important viscosity index improvers and dispersants. 1,3,5-trimethylbenzene is also commonly used as a solvent in paints, varnishes and rubber and chewing gum production due to its low volatility, odor and relatively low toxicity compared to benzene. It also sees some use as an intermediate in the production of perfumes, dyes and pharmaceuticals.

Health and Safety Considerations

While much less hazardous than benzene, 1,3,5-trimethylbenzene should still be handled with care due to potential health risks if proper precautions are not followed. Inhalation of high vapor concentrations can cause dizziness, nausea, and respiratory irritation. Skin contact may lead to defatting of the skin and dermatitis. 1,3,5-trimethylbenzene is not classified as a carcinogen but long term effects are still being studied.

The occupational exposure limits established by organizations like OSHA recommend time-weighted average limits of no more than 25 ppm over 8 hours for workplace airborne 1,3,5-trimethylbenzene exposure. Proper ventilation and use of personal protective equipment like gloves and goggles are recommended when handling the liquid form. 1,3,5-trimethylbenzene vapors are heavier than air and can travel long distances to an ignition source, so precautions against fire and explosion must also be taken, especially in confined or enclosed spaces. Overall, 1,3,5-trimethylbenzene can be safely handled if standard safety protocols for an aromatic hydrocarbon of its class are followed.

Environmental Fate and Regulations

As an aromatic hydrocarbon, 1,3,5-trimethylbenzene is considered a volatile organic compound and has some potential for bioaccumulation in aquatic organisms due to its moderate-high log Kow value of 3.5. Its low water solubility limits extensive contamination of water systems, but 1,3,5-trimethylbenzene released to air or soil may slowly breakdown through interaction with sunlight and microbes. The main breakdown products include carbon dioxide and complex organic molecules.

Most developed countries have established regulatory limits for 1,3,5-trimethylbenzene releases and content in manufactured products due to concerns over environmental and health impacts. In the U.S., the maximum acceptable concentration in drinking water is set at 200 μg/L. The European Union has designated 1,3,5-trimethylbenzene as a dangerous substance subject to labeling and notification if produced or handled above certain annual tonnage thresholds. Overall, with proper handling and controls on industrial emissions, mesitylene is not viewed as a high priority environmental pollutant, but requires responsible management consistent with other volatile aromatics.

As a valuable aromatic hydrocarbon platform chemical, mesitylene plays an important role in many industrial sectors. It is easily produced on a large scale and offers unique properties exploited in the synthesis of lubricant and fuel additives, solvents, and chemical intermediates. While acute toxicity is relatively low compared to benzene, 1,3,5-trimethylbenzene still requires prudent handling, worker exposure controls, and management of industrial emissions to prevent harm to human health and the environment. With appropriate safety measures in place, mesitylene helps facilitate the production of important products and materials in a sustainable manner.
 
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