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Dimethyl terephthalate

Dimethyl terephthalate
  • Dimethyl terephthalate
  • 1,4-Benzenedicarboxylic acid dimethyl ester
  • Dimethyl 4-phthalate
  • Dimethyl p-phthalate
  • Di-Me terephthalate
  • Methyl 4-carbomethoxybenzoate
  • Methyl-p-(methoxycarbonyl)benzoate
  • Methyl terephthalate, di-
  • Terephthalic acid dimethyl ester (2:1)

Dimethyl terephthalate (DMT) is an organic compound with the formula . It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid. it is an intermediate in some schemes for the recycling of PET, e.g. from plastic bottles.

Production

Dimethyl terephthalate (DMT) can be prepared via a direct esterification of terephthalic acid with methanol: : On a commercial scale, this reaction is usually done at 250–300 C using o-xylene as a solvent. The dimethyl terephthalate that is formed is then purified by distillation. Even terephthalic acid of low purity may be used in this method.

Alternatively, it can be prepared from para-xylene by alternating oxidation and methyl-esterification steps via methyl para-toluate (PT).

Structure of monomethyl terephthalate

Uses

DMT is used in the production of polyesters, including polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), and polybutylene terephthalate (PBT). These polymers are produced by transesterification with a diol. In the production of PET, the transesterification initially produces 2-hydroxyethyl methyl terephthalate.

Hydrogenation of DMT affords the diol cyclohexanedimethanol, which is a useful monomer.

Hazards

DMT is not directly dangerous to humans, but it is harmful to aquatic organisms, so environmental releases are avoided. It is flammable and the dust may form explosive mixtures with air.

References

References

  1. J. Sheehan, Richard. "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid".
  2. Elliott, John H.. (1968-10-01). "Thermodynamic properties of high-purity dimethyl terephthalate". Journal of Chemical & Engineering Data.
  3. Zhang, Hui. (2013-04-10). "Solubility of Dimethyl Terephthalate and Monomethyl Terephthalate in the Methanol Aqueous Solution and Its Application To Recycle Monomethyl Terephthalate from Crude Dimethyl Terephthalate". Industrial & Engineering Chemistry Research.
  4. Baikerikar, Kiran K.. (March 2010). "UV curable, liquid diacrylate monomers based on (cis,trans)-1,3/1,4-cyclohexanedimethanol". Journal of Coatings Technology and Research.
  5. {{ICSC. 0262. 02
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