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Dimethyl terephthalate

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Dimethyl terephthalate
Structural formula of dimethyl terephthalate
Names
Preferred IUPAC name Dimethyl terephthalate
Systematic IUPAC name 1,4-Dimethyl benzene-1,4-dicarboxylate
Other names 1,4-Benzenedicarboxylic acid dimethyl ester

Dimethyl 4-phthalate
Dimethyl-p-phthalate
Di-Me terephthalate
Methyl 4-carbomethoxybenzoate
Methyl-p-(methoxycarbonyl)benzoate
Methyl terephthalate

Terephthalic acid methyl ester
Identifiers
CAS Number
3D model (JSmol)
Abbreviations DMT
Beilstein Reference 1107185
ChemSpider
ECHA InfoCard 100.004.011 Edit this at Wikidata
EC Number
  • 204-411-8
MeSH Dimethyl+4-phthalate
PubChem CID
RTECS number
  • WZ1225000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3Key: WOZVHXUHUFLZGK-UHFFFAOYSA-N
  • InChI=1/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3Key: WOZVHXUHUFLZGK-UHFFFAOYSA-N
SMILES
  • COC(=O)C1=CC=C(C=C1)C(=O)OC
  • O=C(OC)c1ccc(cc1)C(=O)OC
Properties
Chemical formula C10H10O6
Molar mass 226.184 g·mol
Appearance white solid
Density 1.2 g/cm³, ?
Melting point 142 °C (288 °F; 415 K)
Boiling point 288 °C (550 °F; 561 K)
Acidity (pKa) -7.21
Basicity (pKb) -6.60
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(CO2CH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.

Production

DMT has been produced in a number of ways. Conventionally and still of commercial value is the direct esterification of terephthalic acid. Alternatively, it can be prepared by alternating oxidation and methyl-esterification steps from p-xylene via methylp-toluate.

Use

DMT is used in the production of polyesters, including polyethylene terephthalate (PET) and polytrimethylene terephthalate. It consists of benzene substituted with carboxymethyl groups (CO2CH3) at the 1 and 4 positions. Because DMT is volatile, it is an intermediate is some schemes for the recyclic of PET, e.g. from plastic bottles.

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

References

  1. ^ Richard J. Sheehan "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a26_193

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