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methyl methacrylate

Product name methyl methacrylate
Synonyms MMA
methacrylic acid methyl ester
methyl 2-methylprop-2-enoate
GOST no data
CAS 80-62-6

Methyl methacrylate (MMA) is a clear, colorless liquid with a pungent unpleasant odor. It is slightly soluble in water (15.9g/1000g at 20°C). Fully miscible in diethyl ether, methanol and most organic solvents. Weakly soluble in ethylene glycol and glycerol. MMA forms azeotropes with water (bp=83°C, 14% of water by mass), methanol (bp=64.2°C, 84.5% of methanol by mass). Chemical properties of methyl methacrylate are determined by double bond and ester function. Thus, it can be hydrolysed in the presence of alkalies or strong mineral acids to release methacrylic acid. Reaction with alcohols catalyzed by alkalies results in interesterification. Also MMA reacts with ammonia to form methacrylamide. MMA can react with hydrogen, halogens, mineral acids, amines, alcohols to form corresponding double bond addition products. It acts as dienophile in Diels-Alder reactions. Methyl methacrylate can be easily polymerized by free radical or anion mechanism. Polymerization of MMA is exothermal process and spontaneous polymerization can occur violently, self-heating accelerates reaction and sometimes process results in explosion.

Production.

  • Most common process for methyl methacrylate preparation in an acetone cyanohydrin (ACH) route, with acetone and hydrogen cyanide as raw materials, and ammonium bisulphate as by-products:

    MMA synthesis from acetone cyanohydrin


  • by isobutylene oxidative ammonolysis to form methacrylonitrile followed by reaction with methanol:

    MMA preparation through methacrylonitrile formation


  • by methoxycarbonylation of ethylene to form methyl propionate with subsequent condensation with formaldehyde:

    MMA synthesis by ethylene carbonylation


  • by isobutylene oxidation with isolation of tert-butyl alcohol which is oxidized in vapour phase to form methacrylic acid. Then methacrylic acid is esterified with methanol to give MMA:

    (CH3)2C=CH2 + H2O --> (CH3)2C(OH)CH3
    (CH3)2C(OH)CH3 + O2 --> CH2=C(CH3)C(O)OH
    CH2=C(CH3)C(O)OH + CH3OH --> CH2=C(CH3)COOCH3 + H2O


    Uses.

  • as the monomer for the production of the transparent plastic polymethyl methacrylate (PMMA) used as a shatterproof replacement for glass;
  • as a comonomer for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC;
  • as a raw material in preparation of high alcohols esters of acrylic acid (by interesterification);
  • in undissolved surface coatings, adhesives, sealants, impact modifiers, emulsion polymers, surgical bone cements, packaging applications, vinyl siding and other construction materials;

  • Manufacturer(s) JSC DOS
    Chemical structure of methyl methacrylate

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