Methyl Acrylate
Title: Methyl Acrylate
CAS Registry Number: 96-33-3
CAS Name: 2-Propenoic acid methyl ester
Additional Names: acrylic acid methyl ester
Molecular Formula: C4H6O2
Molecular Weight: 86.09
Percent Composition: C 55.81%, H 7.02%, O 37.17%
Line Formula: CH2=CHCOOCH3
Literature References: Convenient prepn from ethylene chlorohydrin: DE 571123 (1928 to Rohm & Haas). For direct syntheses from acetylene and carbon monoxide see W. Reppe, Chemie & Technik der Acetylen-Druck-Reaktionen (Weinheim, 2nd ed., 1952). Toxicity study: H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1948).
Properties: Liquid. Acrid odor. Lacrimator. d420 0.9561; d2020 0.9574; d40 0.9702; d4-5 0.9868; d4-10 0.9929. Weighs 8.0 lbs/gal. mp -76.5°. bp608 70°; bp428 60°; bp298 50°; bp200 40°; bp88 20°; bp54 10°; bp41.5 5°; bp32 0°; bp24.5 -5°; bp18.5 -10°. nD20 1.401. Sp heat at -60° = 0.444 cal/g/°C; heat of vaporization 8.25 kcal/mol; heat of combustion 502.88 kcal/mol. Soly in water at 20° = 6 g/100 ml, at 40° = 5 g/100 ml. Soly of water in methyl acrylate at 20° = 1.8 ml/100 g. Sol in alc, ether. Azeotropes: 9.5% water = bp 73°; 49.0% methanol = bp 61°. Easily polymerizes on standing. The polymerization process can be speeded up by heat, light, and peroxides. If pure, the monomer can be stored below +10° without incurring polymerization. LD50 orally in rats: 0.3 g/kg (Smyth, Carpenter).
Melting point: mp -76.5°
Boiling point: bp608 70°; bp428 60°; bp298 50°; bp200 40°; bp88 20°; bp54 10°; bp41.5 5°; bp32 0°; bp24.5 -5°; bp18.5 -10°; Azeotropes: 9.5% water = bp 73°; 49.0% methanol = bp 61°
Index of refraction: nD20 1.401
Density: d420 0.9561; d2020 0.9574; d40 0.9702; d4-5 0.9868; d4-10 0.9929
Toxicity data: LD50 orally in rats: 0.3 g/kg (Smyth, Carpenter)
 
Derivative Type: Polymer
Properties: Transparent, elastic substance. Practically no odor. Little adhesive power. Resists the usual solvents.
 
CAUTION: Potential symptoms of overexposure to the monomer are irritation of eyes, upper respiratory system and skin. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 198. See also Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 409.
Use: The monomer in manuf leather finish resins, textile and paper coatings, and plastic films. Produces the hardest resin of the acrylate ester series.

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