Benzyl acrylate
[CAS# 2495-35-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Benzyl acrylate
• Synonyms: benzyl prop-2-enoate
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• CAS Registry Number: 2495-35-4
• EC Number: 219-673-9
• SMILES: C=CC(=O)OCC1=CC=CC=C1

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*, 1.06 g/mL (Expl.)
• Boiling point: 228.7±9.0 °C 760 mmHg (Calc.)^*, 274.4 °C (Expl.)
• Flash point: 115.5±9.9 °C (Calc.)^*
• Solubility: Soluble in organic solvents (Expl.)
• Index of refraction: 1.517 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H317-H319-H335-H411
• Safety Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Benzyl acrylate is a chemical compound classified as an acrylate ester, formed by the esterification of acrylic acid with benzyl alcohol. Its molecular structure consists of a vinyl group conjugated with an ester functionality attached to a benzyl moiety. Benzyl acrylate is a clear, colorless liquid that possesses a characteristic acrylate odor.

The compound was first synthesized during the early development of acrylic esters used in polymer chemistry. Its synthesis typically involves the reaction of acrylic acid with benzyl alcohol under acid catalysis or by employing suitable esterification agents to facilitate the formation of the ester bond. The development of benzyl acrylate and other acrylate esters was driven by the need for monomers that could polymerize readily and impart desirable properties to the resulting polymers.

Benzyl acrylate is primarily used as a monomer in the production of copolymers and polymers through free radical polymerization. These polymers find applications in coatings, adhesives, sealants, and elastomers due to their ability to provide flexibility, adhesion, and chemical resistance. The benzyl group contributes to the polymer’s hydrophobicity and can influence the thermal and mechanical properties of the polymeric materials.

In coatings, benzyl acrylate-containing polymers are valued for their clarity, gloss, and resistance to environmental factors. The compound is also used in specialty adhesives where strong bonding to various substrates is required, including plastics, metals, and glass. Its role in elastomer formulations contributes to the elasticity and durability of materials used in automotive and industrial applications.

Additionally, benzyl acrylate serves as an intermediate in organic synthesis, where its reactive acrylate group enables further chemical modifications, such as Michael additions and other nucleophilic reactions. This versatility has been exploited in designing functional polymers with tailored properties for biomedical and electronic applications.

Safety considerations for benzyl acrylate include its potential to cause skin and respiratory irritation, necessitating appropriate handling measures in industrial settings. The compound’s reactivity also requires storage away from strong acids, bases, and oxidizing agents to prevent unwanted polymerization or degradation.

Overall, benzyl acrylate’s discovery and incorporation into polymer chemistry have contributed significantly to the development of advanced materials with applications spanning multiple industries. Its utility as a reactive monomer and intermediate underscores its importance in modern chemical manufacturing.

References

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