Dimethyl terephthalate: Difference between revisions

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			{{Distinguish\|text = the psychoactive chemical ], which is also commonly abbreviated as DMT}}

	{{Chembox		{{Chembox
	\| Watchedfields = changed		\|Watchedfields = changed
	\| verifiedrevid = ~~443690907~~		\|verifiedrevid = 447275147
	\| ImageFile = Dimethylterephthalat.svg		\|ImageFile = Dimethylterephthalat.svg
	\| ImageName = Structural formula of dimethyl terephthalate		\|ImageName = Structural formula of dimethyl terephthalate
	\| PIN = Dimethyl ~~terephthalate~~		\|PIN = Dimethyl benzene-1,4-dicarboxylate
			\|OtherNames = Dimethyl terephthalate<br />1,4-Benzenedicarboxylic acid dimethyl ester<br />Dimethyl 4-phthalate<br />Dimethyl ''p''-phthalate<br />Di-Me terephthalate<br />Methyl 4-carbomethoxybenzoate<br />Methyl-p-(methoxycarbonyl)benzoate<br />Methyl terephthalate, di-<br />Terephthalic acid dimethyl ester (2:1)
	\| SystematicName = 1,4-Dimethyl benzene-1,4-dicarboxylate
			\|Section1={{Chembox Identifiers
	\| OtherNames = 1,4-Benzenedicarboxylic acid dimethyl ester<br />
			\|Abbreviations = DMT
	Dimethyl 4-phthalate<br />
			\|CASNo = 120-61-6
	Dimethyl-p-phthalate<br />
			\|CASNo_Ref = {{cascite\|correct\|CAS}}
	Di-Me terephthalate<br />
			\|UNII_Ref = {{fdacite\|correct\|FDA}}
	Methyl 4-carbomethoxybenzoate<br />
			\|UNII = IKZ2470UNV
	Methyl-p-(methoxycarbonyl)benzoate<br />
			\|PubChem = 8441
	Methyl terephthalate<br />
			\|PubChem1 = 12241382
	Terephthalic acid methyl ester<br />
			\|PubChem1_Comment = (<sup>2</sup>''H''<sub>4</sub>)
	\| Section1 = {{Chembox Identifiers
			\|ChEBI = 156286
	\| Abbreviations = DMT
			\|ChemSpiderID = 13863300
	\| CASNo = 120-61-6
	\| ~~CASNo_Ref~~ = {{~~Cascite~~\|correct\|~~CAS~~}}		\|ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\|EINECS = 204-411-8
	\| PubChem = 8441
			\|MeSHName = Dimethyl+4-phthalate
	\| PubChem_Ref = {{Pubchemcite\|correct\|PubChem}}
			\|RTECS = WZ1225000
	\| PubChem1 = 12241382
			\|StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| PubChem1_Comment = (<sup>2</sup>''H''<sub>4</sub>)
			\|StdInChI = 1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3
	\| PubChem1_Ref = {{Pubchemcite\|correct\|PubChem}}
			\|StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| ChemSpiderID = 13863300
			\|StdInChIKey = WOZVHXUHUFLZGK-UHFFFAOYSA-N
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\|SMILES = COC(=O)C1=CC=C(C=C1)C(=O)OC
	\| EINECS = 204-411-8
			\|SMILES1 = O=C(OC)c1ccc(cc1)C(=O)OC
	\| MeSHName = Dimethyl+4-phthalate
			\|InChI = 1/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3
	\| RTECS = WZ1225000
			\|InChIKey = WOZVHXUHUFLZGK-UHFFFAOYSA-N
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
			\|Beilstein = 1107185}}
	\| StdInChI = 1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3
			\|Section2={{Chembox Properties
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
			\|C=10 \| H=10 \| O=4
	\| StdInChIKey = WOZVHXUHUFLZGK-UHFFFAOYSA-N
			\|Appearance = white solid
	\| SMILES = COC(=O)C1=CC=C(C=C1)C(=O)OC
			\|Density = 1.2 g/cm<sup>3</sup>, ?<!-- 1.2 g/cm<sup>3</sup>, solid / ? g/mL, liquid / ? g/L, gas -->
	\| SMILES1 = O=C(OC)c1ccc(cc1)C(=O)OC
			\|MeltingPtC = 142
	\| InChI = 1/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3
			\|BoilingPtC = 288
	\| InChIKey = WOZVHXUHUFLZGK-UHFFFAOYSA-N
			\|pKa = -7.21
	\| Beilstein = 1107185}}
			\|pKb = -6.60}}
	\| Section2 = {{Chembox Properties
	\| C = 10
	\| H = 10
	\| O = 6
	\| ExactMass = 198.083015792 g mol<sup>-1</sup>
	\| Appearance = white solid
	\| Density = 1.2 g/cm³, ?<!-- 1.2 g/cm³, solid / ? g/ml, liquid / ? g/l, gas -->
	\| MeltingPtC = 142
	\| BoilingPtC = 288
	\| pKa = -7.21
	\| pKb = -6.60}}
	\| Section7 = {{Chembox Hazards
	\| ExternalMSDS =
	\| MainHazards =
	}}
	}}		}}

	'''Dimethyl terephthalate''' (DMT) is an ] with the formula C<sub>6</sub>H<sub>4</sub>(~~CO<sub>2</sub>CH~~<sub>3</sub>)<sub>2</sub>. It is the di] formed from ] and ]. It is a white solid that melts to give a distillable colourless liquid.<ref name=Ullmann>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}}</ref>		'''Dimethyl terephthalate''' ('''DMT''') is an ] with the formula C<sub>6</sub>H<sub>4</sub>(COOCH<sub>3</sub>)<sub>2</sub>. It is the ] formed from ] and ]. It is a white solid that melts to give a distillable colourless liquid.<ref name=Ullmann>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}}</ref>

	==Production==		==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-] steps from ] via ~~methyl~~].<ref name=Ullmann/>		Dimethyl terephthalate (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-] steps from ] via ] (PT).<ref name=Ullmann/>

			===Dimethyl terephthalate by the Witten process===
	==Use==
			The method for the production of DMT from ''p''-xylene (PX) and methanol consists of a multistep process involving both oxidation and esterification. A mixture of p-xylene (PX) and methyl ''p''-toluate is oxidized with air in the presence of cobalt and manganese catalysts. The acid mixture resulting from the oxidation is esterified with methanol to produce a mixture of esters. The crude ester mixture is then distilled to remove all the heavy boilers and residue that are produced; lighter esters such as monomethyl terephthalate are recycled to the oxidation section. The raw DMT is then sent to the crystallization section to remove DMT isomers, residual acids and aromatic aldehydes.<ref>{{Cite web\|url = http://www.gtctech.com/technology-licensing/polyester-technologies/dimethyl-terephthalate-technology/\|title = Dimethyl Terephthalate (DMT)\|date = 2013-05-02\|access-date = 2015-03-05\|archive-date = 2017-10-07\|archive-url = https://web.archive.org/web/20171007020846/http://www.gtctech.com/technology-licensing/polyester-technologies/dimethyl-terephthalate-technology/\|url-status = dead}}</ref>
	DMT is used in the production of ]s, including ] (PET) and ]. It consists of ] substituted with carboxymethyl groups (CO<sub>2</sub>CH<sub>3</sub>) 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 ]s.
			]
			Oxidation of methyl p-toluate followed by esterification also yields dimethyl terephthalate (DMT) as shown in the below reaction:<ref name=Ullmann/>
			:]

			===Dimethyl terephthalate by direct esterification===
			DMT can also be made by a different route, namely direct esterification of terephthalic acid with methanol. The dimethyl terephthalate that is formed is then purified by distillation. Even terephthalic acid of low purity may be used in this method.
			:C<sub>8</sub>H<sub>6</sub>O<sub>4</sub> + 2CH<sub>3</sub>OH → C<sub>10</sub>H<sub>10</sub>O<sub>4</sub> + 2 H<sub>2</sub>O
			in the presence of o-xylene at 250–300 °C.

			==Uses==
			DMT is used in the production of ]s, including ] (PET), ] (PTT), and ] (PBT). Structurally, DMT consists of a ] ring substituted at the 1 and 4 positions with methyl carboxylate (-CO<sub>2</sub>CH<sub>3</sub>) groups. Because DMT is volatile, it is an intermediate in some schemes for the recycling of PET, e.g. from ]s.

	Hydrogenation of DMT affords the diol ], which is a useful monomer.		Hydrogenation of DMT affords the diol ], which is a useful monomer.
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	==External links==		==External links==
			* Supplier:Teijin Limited https://web.archive.org/web/20150503041344/http://www.teijin.com/products/chemicals/dmt/
	* http://www.inchem.org/documents/icsc/icsc/eics0262.htm		* http://www.inchem.org/documents/icsc/icsc/eics0262.htm
	* {{ICSC\|0262\|02}}		* {{ICSC\|0262\|02}}
			*

			{{Authority control}}
	{{DEFAULTSORT:Dimethyl Terephthalate}}
	]
	]

			]

			]
	{{ester-stub}}
			]

	]
	]
	]
	]
	]
	]
	]

Latest revision as of 21:03, 16 April 2024

Not to be confused with the psychoactive chemical N,N-Dimethyltryptamine, which is also commonly abbreviated as DMT.

Dimethyl terephthalate
Names

Preferred IUPAC name Dimethyl benzene-1,4-dicarboxylate
Other names 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)
Identifiers
CAS Number	120-61-6
3D model (JSmol)	Interactive image Interactive image
Abbreviations	DMT
Beilstein Reference	1107185
ChEBI	CHEBI:156286
ChemSpider	13863300
ECHA InfoCard	100.004.011
EC Number	204-411-8
MeSH	Dimethyl+4-phthalate
PubChem CID	8441 12241382 (H₄)
RTECS number	WZ1225000
UNII	IKZ2470UNV
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/cm, ?
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(COOCH₃)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

Dimethyl terephthalate (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 methyl p-toluate (PT).

Dimethyl terephthalate by the Witten process

The method for the production of DMT from p-xylene (PX) and methanol consists of a multistep process involving both oxidation and esterification. A mixture of p-xylene (PX) and methyl p-toluate is oxidized with air in the presence of cobalt and manganese catalysts. The acid mixture resulting from the oxidation is esterified with methanol to produce a mixture of esters. The crude ester mixture is then distilled to remove all the heavy boilers and residue that are produced; lighter esters such as monomethyl terephthalate are recycled to the oxidation section. The raw DMT is then sent to the crystallization section to remove DMT isomers, residual acids and aromatic aldehydes.

Oxidation of methyl p-toluate followed by esterification also yields dimethyl terephthalate (DMT) as shown in the below reaction:

Dimethyl terephthalate by direct esterification

DMT can also be made by a different route, namely direct esterification of terephthalic acid with methanol. The dimethyl terephthalate that is formed is then purified by distillation. Even terephthalic acid of low purity may be used in this method.

C₈H₆O₄ + 2CH₃OH → C₁₀H₁₀O₄ + 2 H₂O

in the presence of o-xylene at 250–300 °C.

Uses

DMT is used in the production of polyesters, including polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), and polybutylene terephthalate (PBT). Structurally, DMT consists of a benzene ring substituted at the 1 and 4 positions with methyl carboxylate (-CO₂CH₃) groups. Because DMT is volatile, it is an intermediate in some schemes for the recycling 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
"Dimethyl Terephthalate (DMT)". 2013-05-02. Archived from the original on 2017-10-07. Retrieved 2015-03-05.

External links

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