Names | |
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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 | |
3D model (JSmol) | |
Abbreviations | DMT |
1107185 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.004.011 |
EC Number |
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MeSH | Dimethyl+4-phthalate |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H10O4 | |
Molar mass | 194.186 g·mol−1 |
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 [77 °F], 100 kPa). |
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. [1]
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). [1]
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. [2]
Oxidation of methyl p-toluate followed by esterification also yields dimethyl terephthalate (DMT) as shown in the below reaction: [1]
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.
in the presence of o-xylene at 250–300 °C.
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.
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.
In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.
Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile. Bases catalyze the reaction by removing a proton from the alcohol, thus making it more nucleophilic. The reaction can also be accomplished with the help of other enzymes, particularly lipases.
Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.
Although PET is used in several applications, as of 2022 only bottles are collected at a substantial scale. The main motivations have been either cost reduction or recycle content of retail goods. An increasing amount is recycled back into bottles, the rest goes into fibres, film, thermoformed packaging and strapping. After sorting, cleaning and grinding, 'bottle flake' is obtained, which is then processed by either:
Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.
p-Toluic acid (4-methylbenzoic acid) is a substituted benzoic acid with the formula CH3C6H4CO2H. It is a white solid that is poorly soluble in water but soluble in acetone. A laboratory route to p-toluic acid involves oxidation of p-cymene with nitric acid.
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
p-Xylene (para-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The p- stands for para-, indicating that the two methyl groups in p-xylene occupy the diametrically opposite substituent positions 1 and 4. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and m-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable. The odor threshold of p-xylene is 0.62 parts per million (ppm).
Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.
Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.
Polytrimethylene terephthalate (PTT), is a polyester synthesized and patented in 1941. It is produced by a method called condensation polymerization or transesterification. The two monomer units used in producing this polymer are: 1,3-propanediol and terephthalic acid or dimethyl terephthalate. Similar to polyethylene terephthalate, the PTT is used to make carpet fibers.
The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.
Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.
Dimethyl oxalate is an organic compound with the formula (CO2CH3)2 or (CH3)2C2O4. It is the dimethyl ester of oxalic acid. Dimethyl oxalate is a colorless or white solid that is soluble in water.
Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.
PBAT is a biodegradable random copolymer, specifically a copolyester of adipic acid, 1,4-butanediol and terephthalic acid. PBAT is produced by many different manufacturers and may be known by the brand names ecoflex, Wango,Ecoworld, Eastar Bio, and Origo-Bi. It is also called poly(butylene adipate-co-terephthalate) and sometimes polybutyrate-adipate-terephthalate or even just "polybutyrate". It is generally marketed as a fully biodegradable alternative to low-density polyethylene, having many similar properties including flexibility and resilience, allowing it to be used for many similar uses such as plastic bags and wraps. The structure is a random-block polymer consisting of butanediol–adipic acid and butanediol-terephthalic acid blocks.
Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.
Methyl p-toluate is the organic compound with the formula CH3C6H4CO2CH3. It is a waxy white solid that is soluble in common organic solvents. It is the methyl ester of p-toluic acid. Methyl p-toluate per se is not particularly important but is an intermediate in some routes to dimethyl terephthalate, a commodity chemical.