Dimethyl terephthalate

Base Information

• Chemical Name: Dimethyl terephthalate
• CAS No.: 120-61-6
• Deprecated CAS: 202644-54-0,63143-14-6,63143-14-6
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 2917 37 00
• European Community (EC) Number: 204-411-8
• ICSC Number: 0262
• NSC Number: 3503
• UN Number: 2811
• UNII: IKZ2470UNV
• DSSTox Substance ID: DTXSID0020498
• Nikkaji Number: J2.003F
• Wikipedia: Dimethyl_terephthalate
• Wikidata: Q421276
• Metabolomics Workbench ID: 103984
• ChEMBL ID: CHEMBL1870757
• Mol file: 120-61-6.mol

Synonyms:dimethyl 4-phthalate;dimethyl p-phthalate;dimethyl terephthalate;dimethylterephthalate

Chemical Property of Dimethyl terephthalate

Chemical Property:

• Appearance/Colour: White needle crystal
• Vapor Pressure: 1.15 mm Hg ( 93 °C)
• Melting Point: 140 °C
• Refractive Index: 1.4752
• Boiling Point: 285 °C at 760 mmHg
• PKA: 0[at 20 ℃]
• Flash Point: 148 °C
• PSA: 52.60000
• Density: 1.175 g/cm³
• LogP: 1.25980
• Storage Temp.: Store below +30°C.
• Solubility.: water: slightly soluble0.0493g/L at 20°C
• Water Solubility.: It is slightly soluble in water but soluble in hot alcohol and ether.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 192
• Transport DOT Label: Poison

Purity/Quality:

≥99% ^*data from raw suppliers

1,4-BenzenedicarboxylicAcidDimethylEster ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C(=O)OC
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: May cause mechanical irritation.
• Description: 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.
• Uses: Dimethyl terephthalate is used widely as an industrial intermediate to manufacture polyethylene terephthalate (PET) and dioctyl terephthalate (OECD, 2001).It is used in the Polyester Film (Audio/Video Tape,X-ray Film,Photo Film), Polyester Fiber, Pet Bottle, Polyester Adhesive, Engineering Plastics. DMT is volatile, it is an intermediate in some schemes for the recycling of PET. Dimethyl terephthalate is used in the production of polyesters, including polyethylene terephthalate (PET) and poly trimethylene terephthalate. It consists of benzene substituted with carboxy methyl groups (CO2CH3) at the 1 and 4 positions. Because DMT is volatile, it is an intermediate in some schemes for the recyclic of PET, e.g. from plastic bottles. Hydrogenation of DMT affords the diol cyclohexanedimethanol, which is a useful monomer.

Technology Process of Dimethyl terephthalate

There total 194 articles about Dimethyl terephthalate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.2%

phosgene (75-44-5) + terephthalic acid (100-21-0) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + terephthaloyl chloride (100-20-9)

Guidance literature:

In dichloromethane;

Reference yield: 86.0%

bromochlorobenzene (106-39-8) + carbon monoxide (201230-82-2) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + Methyl 4-chlorobenzoate (1126-46-1) + para-chlorobenzoic acid (74-11-3)

Guidance literature:

With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 8h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

Reference yield: 86.0%

methanol (67-56-1) + bromochlorobenzene (106-39-8) + carbon monoxide (201230-82-2) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + Methyl 4-chlorobenzoate (1126-46-1) + para-chlorobenzoic acid (74-11-3)

Guidance literature:

With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 8h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

upstream raw materials:

diazomethane

terephthalic acid

methanol

1,4-Diacetylbenzene

Downstream raw materials:

terephthalic acid dipropyl ester

terephthalic acid diisopropyl ester

terephthalic acid monoisopropyl ester

p-dibenzyl benzenedicarboxylate

Refernces

• 1、 Dombrovskii,Yanovskaya. "". . . Retrieved 1977.
• 2、 Senthil Murugan, Arumugam,Abel Noelson, Enose Rajan,Annaraj, Jamespandi. "Solvent dependent colorimetric, ratiometric dual sensor for copper and fluoride ions: Real sample analysis, cytotoxicity and computational studies". . p. 131 - 139. Retrieved 2016.
• 3、 Joshi, Bhupendra Prasad,Memeo, Misal Giuseppe,Quadrelli, Paolo. "Solid-phase supported nitrosocarbonyl intermediates: Old scope and new limitations in the organic synthesis". . p. 3271 - 3275. Retrieved 2017.
• 4、 Orazov, Marat,Davis, Mark E.. "Catalysis by framework zinc in silica-based molecular sieves". . p. 2264 - 2274. Retrieved 2016.
• 5、 Gondi, Sudershan R.,Son, David Y.. "Synthesis of N, N′-bis(2-thiazolinyl)-, N, N′-bis(2-thiazolyl)- , and N, N′-bis (2-pyrimidinyl)-benzene dicarboxamides". . p. 3061 - 3072. Retrieved 2004.
• 6、 Warrener, Ronald N.,Russell, Richard A.,Solomon, Robert,Pitt, Ian G.,Butler, Douglas N.. "TRANSFER TECHNOLOGY I. An Improved Protocol for Chemical Synthesis.". . p. 6503 - 6506. Retrieved 1987.
• 7、 Chihara, Teiji. "Highly Selective Monomethyl Esterification of Terephthalic Acid by Use of Monocarboxylate Chemisorption of Alumina". . p. 1215 - 1216. Retrieved 1980.
• 8、 Cacchi, Sandro,Ciattini, Pier Giuseppe,Morera, Enrico,Ortar, Giorgio. "PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES. SYNTHESIS OF ARENECARBOXYLIC ACID DERIVATIVES FROM PHENOLS". . p. 3931 - 3934. Retrieved 1986.
• 9、 Antebi, Shlomo,Arya, Prabhat,Manzer, Leo E.,Alper, Howard. "Carbonylation reactions of iodoarenes with PAMAM dendrimer-palladium catalysts immobilized on silica". . p. 6623 - 6631. Retrieved 2002.
• 10、 Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.. "Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis". supporting information. . Retrieved 2022/02/21.