Dimethyl terephthalate: Difference between revisions

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	\| ImageName = Structural formula of dimethyl terephthalate		\| ImageName = Structural formula of dimethyl terephthalate
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	\| MeSHName = Dimethyl+4-phthalate		\| MeSHName = Dimethyl+4-phthalate
	\| RTECS = WZ1225000		\| RTECS = WZ1225000
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	\| StdInChI = 1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3		\| StdInChI = 1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3
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	\| StdInChIKey = WOZVHXUHUFLZGK-UHFFFAOYSA-N		\| StdInChIKey = WOZVHXUHUFLZGK-UHFFFAOYSA-N
	\| SMILES = COC(=O)C1=CC=C(C=C1)C(=O)OC		\| SMILES = COC(=O)C1=CC=C(C=C1)C(=O)OC

Revision as of 15:19, 8 August 2011

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	120-61-6
3D model (JSmol)	Interactive image Interactive image
Abbreviations	DMT
Beilstein Reference	1107185
ChemSpider	13863300
ECHA InfoCard	100.004.011
EC Number	204-411-8
MeSH	Dimethyl+4-phthalate
PubChem CID	8441 12241382 (H₄)
RTECS number	WZ1225000
CompTox Dashboard (EPA)	DTXSID0020498
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	C₁₀H₁₀O₄
Molar mass	194.186 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 (pK_a)	-7.21
Basicity (pK_b)	-6.60
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y 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

^ 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

External links

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