Ethyl methacrylate

Description

Ethyl Methacrylate is the ester of ethyl alcohol and methacrylic acid. Other chemical names for this compound are Ethyl 2- Methyl-2-Propenoate; 2-Methyl-2-Propenoic Acid, Ethyl Ester; 2-Propenoic Acid, 2-Methyl-, Ethyl Ester; and Methyacrylic Acid, Ethyl Ester. It is a colorless liquid with a melting point below -75℃, a boiling point of 119℃, and a specific gravity of 0.911. It has a molecular weight of 114.14 Da, a refractive index (n, 25/D) of 1.4116, and a flash point (OC) of 70℃. Ethyl Methacrylate has an acrid acrylate odor and is soluble in alcohol and ether. It is readily polymerized and is chemically reactive. Ethyl Methacrylate monomer is very hydrophobic and poorly “wets” the hydrophilic keratin surface of the nail plate, requiring hydrophilic nail primers and additives to obtain sufficient adhesion[1].

References

[1] Andersen, F. A. “Amended Final Report on the Safety Assessment of Ethyl Methacrylate.” International Journal of Toxicology 21 1 (2002): 63–79.

Chemical properties

colourless liquid with an unpleasant odour

Chemical properties

Ethyl methacrylate is a clear, colorless, and highly flammable liquid that polymerizes but at a slower rate than that of the parent acrylate.

The Uses of Ethyl methacrylate

Ethyl methacrylate can be manufactured via a reaction of methacrylic acid or methyl acrylate with ethanol. It is used primarily for manufacturing polymers and as a component of acrylic polymers for surface coatings and as a structural monomer for some artificial fingernail formulations.

The Uses of Ethyl methacrylate

Polymers, chemical intermediates.

The Uses of Ethyl methacrylate

Ethyl methacrylate is used in dental protheses or in photobonded sculptured nails.

Production Methods

Ethyl methacrylate can be manufactured via a reaction of methacrylic acid or methyl acrylate with ethanol.

General Description

A colorless moderately toxic liquid with an acrid odor. Flash point of 70°F. Boiling point 278°F. Vapors irritate the eyes and respiratory system. Less dense than water. Not soluble in water. Used to make polymers and other chemicals.

Air & Water Reactions

Highly flammable. A very dangerous fire and explosion hazard. Not soluble in water.

Reactivity Profile

May polymerize if heated for prolonged periods or accidentally contaminated. If polymerization takes place inside a container, the container may violently rupture. Can react with oxidizing materials. When heated to decomposition Ethyl methacrylate emits irritating fumes and acrid smoke [Sax, 9th ed., 1996, p. 1576].

Hazard

Flammable, dangerous fire and explosion hazard. An irritant.

Health Hazard

Inhalation may cause irritation of the mucous membrane. Ingestion causes irritation of mouth and stomach. Contact with liquid irritates eyes and skin.

Fire Hazard

Behavior in Fire: Sealed containers may rupture explosively if hot. Heat can cause a violent polymerization reaction with rapid release of energy. Vapors are heavier than air and can travel to a source of ignition and flash back.

Flammability and Explosibility

Non flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: If proper concentration of inhibitor is not present or when material is hot, a violent polymerization reaction may occur; Inhibitor of Polymerization: Oxygen in the air inhibits polymerization.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by inhalation. Experimental teratogenic and reproductive effects. A skin irritant. A very dangerous fire and explosion hazard when exposed to heat, sparks, or flame; can react with oxidzing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

Purification Methods

Wash the ester successively with 5% aqueous NaNO2, 5% NaHSO3, 5% NaOH, then water. Dry it over MgSO4, add 0.2% (w/w) of phenyl-.-naphthylamine, and distil it through a short Vigreux column (p 11) [Schultz J Am Chem Soc 80 1854 1958]. [Beilstein 2 IV 1523.]