Dimethyl Phthalate

Base Information

• Chemical Name: Dimethyl Phthalate
• CAS No.: 131-11-3
• Deprecated CAS: 64441-70-9,1352054-35-3,1352054-35-3
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 2917.34
• European Community (EC) Number: 205-011-6
• ICSC Number: 0261
• NSC Number: 15398
• UN Number: 3082
• UNII: 08X7F5UDJM
• DSSTox Substance ID: DTXSID3022455
• Nikkaji Number: J5.557C
• Wikipedia: Dimethyl_phthalate
• Wikidata: Q423551
• NCI Thesaurus Code: C76750
• Metabolomics Workbench ID: 67565
• ChEMBL ID: CHEMBL323348
• Mol file: 131-11-3.mol

Synonyms:dimethyl phthalate;dimethyl phthalate, conjugate diacid;dimethylphthalate

Chemical Property of Dimethyl Phthalate

Chemical Property:

• Appearance/Colour: clear oily liquid
• Vapor Pressure: 0.008 hPa (20 °C)
• Melting Point: 2 °C(lit.)
• Refractive Index: 1.512
• Boiling Point: 282.7 °C at 760 mmHg
• Flash Point: 146.7 °C
• PSA: 52.60000
• Density: 1.175 g/cm³
• LogP: 1.25980
• Storage Temp.: 2-8°C
• Solubility.: 4.0g/l
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 200
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl phthalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 20/21/22-36/37/38-39/23/24/25-23/24/25-11-52
• Safety Statements: 24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Phthalate Esters
• Canonical SMILES: COC(=O)C1=CC=CC=C1C(=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.
• Uses: 1. It is used as a plasticizer for cellulose acetate, polyvinyl fluoride coating repellent agents and solvents. 2. Dimethyl Phthalate is rodenticide rat poison, rat finished, chlorine mouse ketone intermediates, it is also an important solvent. 3. The product is a plasticizer for variety of resin having a very strong dissolving power, is compatible with a variety of cellulose resin, rubber, vinyl resin. It displays good film-forming character, adhesion and water resistance. It is usually used with diethyl phthalate in cellulose acetate film, varnish, transparent paper and molding powder production . A small amount of the product is used in nitrocellulose production. The product can also be used as a nitrile rubber plasticizers, with good resistance to cold products. The product can be mixed with other plasticizers. It can overcome the high volatility , low-temperature crystallization and other shortcomings. The products are also used as DEET oil (crude oil) and DDT solvents. The product is also used as gas chromatography stationary phase. Dimethyl phthalate is used as an insect repellant. It has also been employed as a solvent for cellulose acetate. Insect repellant. It is used as insect repellent. Dimethyl Phalate is the methyl ester of phthalic acid. Dimethyl phthalate is an ectoparasiticide and has many other uses, including in solid rocket propellants, plastics, and insect repellents. Solvent and plasticizer for cellulose acetate and cellulose acetate-butyrate compositions. Insect repellent for personal protection against biting insects.
• Production method: Esterified under normal pressure with an excess amount of the anhydride (4-fold) in methanol, excess methanol was refluxed with water, DMP was obtained from the reaction. The 600kg anhydride, 450kg methanol 90-95 ℃', 1050ml concentrated sulfuric acid were added into the reaction pot successively, heated to reflux for 24h. After completion of the reaction, methanol recovery, then neutralized with sodium carbonate, washed with water, and then distilled to obtain the finished product. Industrial grade product dimethyl phthalate purity of ≥99%. Material consumption fixed: anhydride 750kg/t, methanol 445kg/t.
• Description: Phthalates are plasticizers, and increase the flexibility of plastics. They are also found in deodorant formulations, perfumes, emollients and insect repellents.
• Physical properties: Clear, colorless, odorless, moderately viscous, oily liquid

Technology Process of Dimethyl Phthalate

There total 169 articles about Dimethyl Phthalate 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: 85.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2,3-dibromobenzene (583-53-9) → 2-bromobenzoic acid methyl ester (610-94-6) + phthalic acid dimethyl ester (131-11-3,64441-70-9) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5)

Guidance literature:

With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 18h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

Reference yield: 85.0%

carbon monoxide (201230-82-2) + 2,3-dibromobenzene (583-53-9) → 2-bromobenzoic acid methyl ester (610-94-6) + phthalic acid dimethyl ester (131-11-3,64441-70-9) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5)

Guidance literature:

With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 18h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

Reference yield: 76.0%

2-bromo-1-chlorobenzene (694-80-4) + carbon monoxide (201230-82-2) → methyl chlorobenzoate (610-96-8) + phthalic acid dimethyl ester (131-11-3,64441-70-9) + ortho-chlorobenzoic acid (118-91-2)

Guidance literature:

With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 10h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

upstream raw materials:

methanol

Diethyl phthalate

phthalic anhydride

Dimethyl ether

Downstream raw materials:

dibenzyl phthalate

3α,6α-diacetoxy-24,24-diphenyl-5β-choladiene-(20(22)ξ,23)

2-[2-(1-hydroxy-1-methylethyl)phenyl]-2-propanol

1-[2-(α-hydroxy-isopropyl)-phenyl]-ethanone

Refernces

• 1、 Ashe,A.J.,Friedman,H.S.. "". . p. 1283 - 1286. Retrieved 1977.
• 2、 Inouye et al.. "-". . p. 4713. Retrieved 1967.
• 3、 Pohlit,Lemmon. "". . p. 2558. Retrieved 1971.
• 4、 Miller,R.D.,Hedaya,E.. "". . p. 5401 - 5402. Retrieved 1969.
• 5、 Miller et al.. "". . p. 1845. Retrieved 1976.
• 6、 Varlamov, Alexey V.,Savitkina, Elena A.,Krapivko, Anatoly P.,Chernyshev, Alexey I.,Levov, Alexander N.. "Cleavage of 7- And 8-nitropyrido[1,2-a]benzimidazoles on treatment with dimethyl acetylenedicarboxylate". . p. 127 - 128. Retrieved 2005.
• 7、 Beerly, Rene,Rebek, Julius. "Barrelene Derivatives-Potential Modules for Assembly". . p. 1813 - 1816. Retrieved 1995.
• 8、 Stephan, Constantin,Munz, Christina,Dieck, Heindirk tom. "The palladium-catalyzed addition of various vinyl compounds to dimethyl acetylenedicarboxylate". . p. 223 - 227. Retrieved 1993.
• 9、 Sun, Chia-Hsing,Chow, Tahsin J.. "Reactions of 2,3-dicarbomethoxy-7-oxabicycloheptadiene with molybdenum carbonyls". . p. C21 - C24. Retrieved 1987.
• 10、 Elman,Perepukhov,Ovsyannikova,Maksimychev. "Preparation of phthalates via carbonylation of o-dibromobenzenes in solutions of Pd catalysts and reactivity of Ar?Br bonds". . . Retrieved 2017.