What Is Methyl Benzoate?
Methyl benzoate is a colorless liquid characterized by an aromatic odor.
Also known under the IUPAC designation methyl benzoate, this organic compound is alternately known as methylbenzoate, benzoic acid methyl ester, or Niobe oil.
With the chemical formula C8H8O2 and a molecular weight of 136.15, its CAS registration number is 93-58-3. It is classified as a hazardous substance under various safety laws.
Uses of Methyl Benzoate
This ester compound, recognized for its fruity aroma, is naturally present in guava, mango, and kiwi fruit. It finds applications in food flavoring and the composition of ylang-ylang-based fragrances and perfumes due to its distinct aroma.
Additionally, methyl benzoate serves various purposes, including acting as a solvent for synthetic resins, cellulose esters, and rubber, assisting in the dyeing of polyester fibers, and as a component in fungicides and pesticides. Male orchid bees collect methyl benzoate from plants for use in pheromone synthesis.
In chemical synthesis, it serves as a precursor for:
- the selective synthesis of benzaldehyde via supported manganese oxide catalysts
- the Friedel-Crafts acylation reaction with aryl compounds to produce benzophenone derivatives
Properties of Methyl Benzoate
As a liquid, it has a melting point of -15°C, a boiling point of 199.6°C, a flash point of 82°C, and a density of 1.094 g/cm3 at room temperature. Its lipophilic nature allows for high solubility in ethanol and acetone, while it remains insoluble in water.
The reactivity of methyl benzoate varies, targeting either the ring or the ester groups based on the reactants employed. For instance, nitration with nitric acid under acidic conditions yields 3-nitro methyl benzoate. Similarly, its carbonyl carbon’s susceptibility to nucleophilic attack facilitates hydrolysis with NaOH solution to produce sodium benzoate.
Other Information on Methyl Benzoate
1. Production Methods
Methyl benzoate can be synthesized through Fischer’s esterification, reacting benzoic acid with methanol in the presence of a minimal amount of a strong acid catalyst, such as sulfuric acid.
Naturally, it is extracted from specific aquatic plants, like the Japanese pepper tree.
2. Safety Precautions and Storage
Handling
Being a flammable substance, methyl benzoate should be kept away from ignition sources such as high temperatures, open flames, and sparks. Its vapors may ignite from electrostatic discharge.
Appropriate grounding or other anti-static measures are advisable. Utilize in well-ventilated areas, preferably in a fume hood, and always wear personal protective equipment.
Fire Response
Thermal decomposition from fire can produce hazardous gases like carbon dioxide and carbon monoxide. Employ water spray, foam, powder extinguishers, carbon dioxide, or sand to combat fires.
Skin Contact
Avoid direct skin contact by wearing suitable protective clothing and gloves, ensuring that sleeves remain unrolled to prevent skin exposure.
In case of contact, cleanse with soap and ample water. Remove and isolate contaminated clothing. Seek medical advice if skin irritation develops.
Eye Contact
Use protective eyewear or goggles. If contact occurs, rinse your eyes thoroughly with water. Remove contact lenses if easily possible and continue rinsing. Seek medical attention if irritation persists.
Storage
Store in a glass container with a tight seal in a well-ventilated, cool location away from direct sunlight. Keep away from strong oxidizers.