Benzyl methacrylate Chemical Properties

Melting point:

<25 °C

Boiling point:

95-98 °C/4 mmHg (lit.)

Density 

1.04 g/mL at 25 °C (lit.)

vapor pressure 

3Pa at 20℃

refractive index 

n20/D 1.512(lit.)

Flash point:

225 °F

storage temp. 

2-8°C(protect from light)

form 

clear liquid

color 

Colorless

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

BRN 

2045924

Stability:

Stable. Flammable. Incompatible with free-radical initiators, oxidizing agents, reducing agents. Avoid heat. Light-sensitive.

LogP

3.1 at 20℃

CAS DataBase Reference

2495-37-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzyl methacrylate(2495-37-6)

EPA Substance Registry System

2-Propenoic acid, 2-methyl-, phenylmethyl ester (2495-37-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

1

TSCA 

Yes

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Benzyl methacrylate Usage And Synthesis

Uses in Perfume

Benzyl methacrylate has found some use in perfume compositions where it may introduce very desirable notes in Rose and other floral fragrances, in Chypre, Oriental and heavy woody fragrance types, etc. It blends excellently with Oakmoss, Vetiver, Phenylacetaldehyde dimethylacetal, Citrcnel101,as well as with Lavender, Lavandin, Spike Lavender, etc. The ester is also used in soap and detergent perfumes, where its low cost allows for a more liberal application.

Description

The cyclic methacrylate monomer benzyl methacrylate (BzMA) was evaluated as an alternative to traditional methyl methacrylate (MMA) as a hard monomer in the application of an acrylate latex pressure-sensitive adhesive (PSA). BzMA is widely used in nanoimprinting lithography, paint applications, inkjet inks, transparent adhesives, orthodontic adhesive compositions, and stationary phases in liquid chromatography[1].

Chemical Properties

Colorless oily liquid. Very slightly soluble in water, soluble in alcohol and oils. Soft, warm, herbaceous-rosy odor of moderate tenacity.

Uses

Benzyl methacrylate is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Flammability and Explosibility

Not classified

Synthesis

GENERAL METHODS: In Examples 62-64, methyl methacrylate was converted to benzyl methacrylate with benzyl alcohol by an ester exchange reaction as shown in Table 13. In Example 62, lanthanum nitrate and tri-n-octylphosphine were first azeotropically refluxed with dimethyl carbonate for 1 hour according to the method of Example 24, followed by evaporation of the dimethyl carbonate at room temperature, and the resulting catalyst was used in the reaction. In Examples 63 and 64, methyltridecylammonium methyl carbonate was used directly as the catalyst. Under these conditions, benzyl methacrylate was obtained in high yields. It is to be noted that in Example 62, higher yields than Example 62 are expected to be obtained if isolated phosphonium salts are used rather than in situ prepared catalysts. Although not listed in Table 13, a variety of by-products are generated when potassium tert-butoxide is used as a catalyst.

Advantages

The Tg of the copolymer was elevated, while thermal stability was first increased and then decreased with the introduction of Benzyl methacrylate. Besides, the water resistance of the latex PSA was improved by the presence of BzMA, which was confirmed by water contact angle measurements. Furthermore, as the BzMA content increased, the gel content slightly decreased, while sol molecular weight (Mw, Mn) of the polymer increased. Finally, with respect to the adhesive properties of the PSA, it was observed that loop tack decreased, while shear strength increased with the incorporation of BzMA. 180° peel strength initially increased and then decreased with the addition of Benzyl methacrylate from 0 to 30 wt%, with a maximum value at 5 wt%.

References

[1] Cheng Fang , Xiaolong Zhu, Fuxiang Zhou . “The application research of benzyl methacrylate (BzMA) in acrylate latex pressure sensitive adhesives.” International Journal of Adhesion and Adhesives 107 (2021): Article 102861.

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