Dimethyl carbonate

Base Information

• Chemical Name: Dimethyl carbonate
• CAS No.: 616-38-6
• Molecular Formula: C3H6O3
• Molecular Weight: 90.0788
• Hs Code.: 2920 90 10
• European Community (EC) Number: 210-478-4
• ICSC Number: 1080
• NSC Number: 9371
• UN Number: 1161
• UNII: KE9J097SPN
• DSSTox Substance ID: DTXSID9029192
• Nikkaji Number: J7.032G
• Wikipedia: Dimethyl_carbonate
• Wikidata: Q416254
• Metabolomics Workbench ID: 43920
• ChEMBL ID: CHEMBL3185216
• Mol file: 616-38-6.mol

Synonyms:dimethyl carbonate;methyl carbonate;methyl carbonate, 11C-labeled;methyl carbonate, hexachloroantimonate (1-);methyl carbonate, hexachloroantimonate (1-) (2:1)

Chemical Property of Dimethyl carbonate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 18 mm Hg ( 21.1 °C)
• Melting Point: 2-4 °C(lit.)
• Refractive Index: n20/D 1.368(lit.)
• Boiling Point: 90.5 °C at 760 mmHg
• Flash Point: 18.333 °C
• PSA: 35.53000
• Density: 1.024 g/cm³
• LogP: 0.39920
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Solubility.: 139g/l
• Water Solubility.: 139 g/L
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 90.031694049
• Heavy Atom Count: 6
• Complexity: 44
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl Carbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-2017/9/16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)OC
• Effects of Short Term Exposure: The vapour is mildly irritating to the eyes.
• Uses: Dimethyl carbonate product can be used as traditional substitute of toxic materials phosgene, dimethyl sulfate and methyl chloride and so on. It can be used for synthesis of polycarbonate, diphenyl carbonate, isocyanate and allyl diglycol carbonate ester; it can also used for the synthesis of various kinds of carbamate pesticides such as carbaryl and so on; it can also be used as intermediate of organic synthesis such as anisole, dimethoxybenzene, alkylated aryl amines, symmetrical diamine urea, methyl carbazate and so on; in the pharmaceutical industry, it can be used for making amino oxazolidinone, ciprofloxacin, β-keto acid ester class pharmaceutical intermediates. In addition, it can be used as additives of gasoline, diesel fuel, the refrigerator oil and solvent. Dimethyl carbonate is used as a solvent in organic synthesis and considered as a replacement for solvent like methyl ethyl ketone, tert-butyl acetate and parachlorobenzotrifluoride. It is involved as an intermediate in the preparation of diphenylcarbonate, which in turn is used as a key raw material for the synthesis of Bisphenol-A-polycarbonate. It is also used as a 'green' methylating agent involved in the methylation of aniline, phenols and carboxylic acids. It can be used as a fuel additive due to its high oxygen content. It also finds applications related to supercapacitors and lithium batteries. Environmentally benign substitute for dimethyl sulfate, q.v., and methyl halides in methylation reactions and for phosgene, q.v., in methylcarbonylation reactions.
• Production method: It can be produced through the reaction between methyl chloroformate ([79-22-1]) and methanol. The raw material, methyl chloroformate is produced from the reaction between methanol and phosgene. For the preparation, it is also plausible to have this phosgenation product been without isolation and add excess methanol for reflux reaction to synthesize dimethyl carbonate. The above reaction is called conventional phosgene method. 2 Transesterification methods: this is based on the transesterification between ethylene carbonate or propylene carbonate and methanol which can also produce dimethyl carbonate. This method has a high yield, small equipment corrosion and mild reaction conditions. However, the source of raw materials is limited by the development of petrochemical industry and the elements utilization rate is low. 3. Oxidative carbonylation method: this is based on the reaction of methanol, carbon monoxide and oxygen in the catalyst for direct synthesis of dimethyl carbonate. This method has a lot of advantages including easily available and cheap raw material, low toxicity and simple process. Therefore, it is the most promising approach. According to the technology conditions, it can be divided into liquid phase method and gas phase method. Gas phase can be further divided into one-step and two-step method, wherein the liquid phase of methanol oxidation-carbonylation method and the gas-phase oxidative carbonylation step method has been industrialized while the one-step way of gas-phase oxidative-carbonylation of methanol is still in development. 4. The synthesis reaction between methanol and CO2. This process route is still in development. 5. Synthesis method via reaction between methanol and urea. This process route is still in development.

Technology Process of Dimethyl carbonate

There total 288 articles about Dimethyl carbonate 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:

C8H18N2O3Si (87580-31-2) → Trimethylmethoxysilane (1825-61-2) + C3H6N3O3(1-)*K(1+) (135516-79-9) + carbonic acid dimethyl ester (616-38-6)

Guidance literature:

With potassium methanolate; tin(IV) chloride; dinitrogen pentoxide; Yield given. Multistep reaction; 1.) CH₂Cl₂, -15 deg C, 90 min, 2.) -40 deg C, 30 min;

DOI:10.1007/BF00961361

Reference yield:

C8H18N2O4Si (87580-29-8) → Trimethylmethoxysilane (1825-61-2) + C3H6N3O4(1-)*K(1+) (135516-78-8) + carbonic acid dimethyl ester (616-38-6)

Guidance literature:

With potassium methanolate; tin(IV) chloride; dinitrogen pentoxide; Yield given. Multistep reaction; 1.) CH₂Cl₂, -20 deg C, 50 min, 2.) -40 deg C, 30 min;

DOI:10.1007/BF00961361

Reference yield:

methanol (67-56-1) + C14H10ClN3O5 → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-chlorobenzamidoxime (5033-28-3) + carbonic acid dimethyl ester (616-38-6)

Guidance literature:

With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;

DOI:10.1135/cccc19990265

upstream raw materials:

methanol

phosgene

trichloromethyl ether

chloropicrin

Downstream raw materials:

bis(trichloromethyl) carbonate

2-oxotetrahydrofuran-3-carboxylic acid methyl ester

α-(2-Tetrahydrofuranylidene)-γ-butyrolactone

3-methyltetrahydro-2-furanone

Refernces

• 1、 Chaugule, Avinash A.,Tamboli, Ashif H.,Kim, Hern. "Efficient fixation and conversion of CO2 into dimethyl carbonate catalyzed by an imidazolium containing tri-cationic ionic liquid/super base system". . p. 42279 - 42287. Retrieved 2016.
• 2、 Wang, Dengfeng,Zhang, Xuelan,Gao, Yangyan,Xiao, Fukui,Wei, Wei,Sun, Yuhan. "Zn/Fe mixed oxide: Heterogeneous catalyst for the synthesis of dimethyl carbonate from methyl carbamate and methanol". . p. 430 - 433. Retrieved 2010.
• 3、 Chiang, Chao Lung,Lin, Kuen Song,Yu, Ssu-Han. "Preparation and characterization of H3PW12O40/ZrO2 catalyst for carbonation of methanol into dimethyl carbonate". . p. 3797 - 3811. Retrieved 2018.
• 4、 Kohno, Kazufumi,Choi, Jun-Chul,Ohshima, Yoshihiro,Yili, Abulimiti,Yasuda, Hiroyuki,Sakakura, Toshiyasu. "Reaction of dibutyltin oxide with methanol under CO2 pressure relevant to catalytic dimethyl carbonate synthesis". . p. 1389 - 1392. Retrieved 2008.
• 5、 Kumar, Subodh,Kumar, Pawan,Jain, Suman L.. "Graphene oxide immobilized copper phthalocyanine tetrasulphonamide: The first heterogenized homogeneous catalyst for dimethylcarbonate synthesis from CO2 and methanol". . p. 18861 - 18866. Retrieved 2014.
• 6、 Schneider, Martin Johannes,Haumann, Marco,Stricker, Marion,Sundermeyer, Joerg,Wasserscheid, Peter. "Gas-phase oxycarbonylation of methanol for the synthesis of dimethyl carbonate using copper-based Supported Ionic Liquid Phase (SILP) catalysts". . p. 71 - 78. Retrieved 2014.
• 7、 Zhu, Li,Lu, Feng,Liu, Xiao-Dan,Liu, Xiao-Qin,Sun, Lin-Bing. "A new redox strategy for low-temperature formation of strong basicity on mesoporous silica". . p. 10058 - 10061. Retrieved 2015.
• 8、 Dibenedetto, Angela,Aresta, Michele,Giannoccaro, Potenzo,Pastore, Carlo,Papai, Imre,Schubert, Gabor. "On the existence of the elusive monomethyl ester of carbonic acid [CH 3OC(O)OH] at 300 K: 1H- and 13C NMR measurements and DFT calculations". . p. 908 - 913. Retrieved 2006.
• 9、 Wang, Xuan Yun,Liu, Su Qin,Huang, Ke Long,Feng, Qiu Ju,Ye, De Lai,Liu, Bing,Liu, Jin Long,Jin, Guan Hua. "Fixation of CO2by electrocatalytic reduction to synthesis of dimethyl carbonate in ionic liquid using effective silver-coated nanoporous copper composites". . p. 987 - 990. Retrieved 2010.
• 10、 Sankar, Meenakshisundaram,Satav, Srikanth,Manikandan, Palanichamy. "Transesterification of cyclic carbonates to dimethyl carbonate using solid oxide catalyst at ambient conditions: Environmentally benign synthesis". . p. 575 - 578. Retrieved 2010.