Outline Reference quality standards The application of dimethyl carbonate Chemical Properties Uses Production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage characteristics Extinguishing agent
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Dimethyl carbonate

Outline Reference quality standards The application of dimethyl carbonate Chemical Properties Uses Production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage characteristics Extinguishing agent
Product Name
Dimethyl carbonate
CAS No.
616-38-6
Chemical Name
Dimethyl carbonate
Synonyms
DIMETHYL CARBONATE;METHYL CARBONATE;CARBONIC ACID DIMETHYL ESTER;Dimethylcarbonat;dimetyl carbonate;methylcarbonate((meo)2co);CH3OCOOCH3;Dimethylcarbonate,99%;DMC;DMC
CBNumber
CB8853983
Molecular Formula
C3H6O3
Formula Weight
90.08
MOL File
616-38-6.mol
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Dimethyl carbonate Property

Melting point:
2-4 °C (lit.)
Boiling point:
90 °C (lit.)
Density 
1.069 g/mL at 25 °C (lit.)
vapor density 
3.1 (vs air)
vapor pressure 
18 mm Hg ( 21.1 °C)
refractive index 
n20/D 1.368(lit.)
Flash point:
65 °F
storage temp. 
Store below +30°C.
solubility 
139g/l
form 
Liquid
color 
<50(APHA)
Odor
Pleasant
explosive limit
4.22-12.87%(V)
Water Solubility 
139 g/L
Sensitive 
Moisture Sensitive
Merck 
14,3241
BRN 
635821
Dielectric constant
3.1699999999999999
Stability:
Stable. Highly flammable. Incompatible with strong oxidizing agents, potassium t-butoxide.
InChIKey
IEJIGPNLZYLLBP-UHFFFAOYSA-N
LogP
0.23-0.354 at 20-25℃
CAS DataBase Reference
616-38-6(CAS DataBase Reference)
NIST Chemistry Reference
Carbonic acid, dimethyl ester(616-38-6)
EPA Substance Registry System
Carbonic acid, dimethyl ester (616-38-6)
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Safety

Hazard Codes 
F
Risk Statements 
11
Safety Statements 
9-16-2017/9/16
RIDADR 
UN 1161 3/PG 2
WGK Germany 
1
RTECS 
FG0450000
Autoignition Temperature
458 °C
TSCA 
Yes
HS Code 
2920 90 10
HazardClass 
3
PackingGroup 
II
Hazardous Substances Data
616-38-6(Hazardous Substances Data)
Toxicity
LD50 in rats (g/kg): 13.8 orally; 2.5 dermally; LC50 (4 hr) in rats (mg/l): 140 by inhalation (Ono)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.03525
Product name
Dimethyl carbonate
Purity
for synthesis
Packaging
100mL
Price
$39.9
Updated
2024/03/01
Sigma-Aldrich
Product number
8.03525
Product name
Dimethyl carbonate
Purity
for synthesis
Packaging
1L
Price
$95.3
Updated
2024/03/01
Sigma-Aldrich
Product number
8.03525
Product name
Dimethyl carbonate
Purity
for synthesis
Packaging
2.5L
Price
$167
Updated
2024/03/01
Sigma-Aldrich
Product number
517127
Product name
Dimethyl carbonate
Purity
anhydrous, ≥99%
Packaging
1l
Price
$134
Updated
2024/03/01
Sigma-Aldrich
Product number
13259
Product name
Dimethyl carbonate
Purity
analytical standard
Packaging
100mg
Price
$108
Updated
2024/03/01
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Dimethyl carbonate Chemical Properties,Usage,Production

Outline

Dimethyl carbonate is briefly referred to as DMC. At room temperature, it is a colorless and transparent liquid with a pungent odor with a relative density (D204) of 1.0694, a melting point of 4 °C, boiling point of 90.3 °C, the flash point being 21.7 °C (opening) and being 16.7 °C (closed ) and the refractive index (nd20) being 1.3687. It is flammable and non-toxic and is miserable with almost all organic solvents in any proportion with alcohols, ketones and esters. It is slightly soluble in water. It can be used as the methylating agent. Compared with other methylating reagent such as methyl iodide and dimethyl sulfate, dimethyl carbonate is less toxic, and biodegradable.
The past method of making dimethyl carbonate with phosgene as raw materials is not frequently used. Instead, people now adopt the catalytic oxidative carbonylation of methanol in the presence of oxygen which is more environmentally friendly than the previous method.
Dimethyl carbonate can enable to methylation of aniline, phenol and carboxylic acid. However, many reaction demands high-pressure. DBU can be added during reflux of DMC for catalyzing the methylation of carboxylic acid with dimethyl carbonate.

Reference quality standards

Index name battery grade excellent grade first grade qualified experimental methods
Appearance, colorless and transparent liquid
Dimethyl carbonate content% ≥99.9 ≥99.5 ≥99.0 ≥98.5 Gas Chromatography
Water, Water Content% ≤30ppm ≤0.10 ≤0.10 ≤0.10 GB606
Alkalinity mmol/10Og-≤0.10 ≤0.12 ≤0.12 Q/GNPC-JX 017
Non-volatile matter, %-≤0.02 ≤0.02 ≤0.02 GB6324.2
Peroxide (By H2O2) ≤5ppm---GB6016-85
Density (20 ℃), Density g/cm3 1.071 ± 0.005

The application of dimethyl carbonate

1, a novel type of low toxicity solvents and can substitute solvent such as toluene, xylene, ethyl acetate, butyl acetate, acetone or butanone in paints and adhesive industry, and is environmentally friendly green chemical products.
2, it is excellent methylating agent, carbonylation agent, hydroxymethylation agent and methoxylation agent and is a kind of chemical raw material of wide application.
3, it can be used as ideal substitute of highly toxic product such as phosgene, dimethyl sulfate, and methyl chloroformate.
4, it can be used for synthesizing polycarbonate, diphenyl carbonate, and isocyanate and so on.
5, in the field of medicine, it can be for the synthesis of anti-infective drugs, anti-inflammatory medicines, vitamin-class medicines and central nervous system drugs.
6, in the field of pesticides, it can be mainly used for the production of methyl isocyanate, thereby producing some carbamate drugs, pesticides (anisole).
7, it can be used as gasoline additives and lithium battery electrolyte and so on.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Chemical Properties

It is colorless liquid with a pungent odor. It is insoluble in water and soluble in alcohol, ether and other organic solvents.

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.

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.

Category

Flammable liquid

Toxicity grading

Low toxicity

Acute toxicity

Oral-rat LD50: 13000 mg/kg; Oral-Mouse LD50: 6000 mg/kg.

Flammability and hazard characteristics

It is flammable in case of fire, high temperature and oxidant with burning causing irritated fume.

Storage characteristics

Treasury: ventilation, low-temperature and dry; store it separately from oxidants.

Extinguishing agent

Dry powder dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Chemical Properties

Dimethyl carbonate is miscible with most acids and alkalis, soluble in most organic solvents, but insoluble in water.

Uses

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.

Uses

Environmentally benign substitute for dimethyl sulfate, q.v., and methyl halides in methylation reactions and for phosgene, q.v., in methylcarbonylation reactions.

Definition

ChEBI: Dimethyl carbonate is a carbonate ester that is carbonic acid in which both hydrogens are replaced by methyl groups. A flammable, colourless liquid (m.p. 2-4°C, b.p. 90°C) with a characterstic ester-like odour, it is used as a 'green' methylating agent and as a solvent. It has a role as a solvent and a reagent.

Preparation

Dimethyl carbonate (DMC) is formed by the reaction of MeOH with phosgene or methyl chloroformate in the presence of a concentrated sodium hydroxide solution in a two-phase reaction in high yields and purity. Other alcohols can also be phosgenated. As DMC is now more easily accessible via the direct oxidative carbonylation of MeOH, phosgenation is losing its attractiveness in this application.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 1122, 1984 DOI: 10.1021/jo00180a033
Tetrahedron Letters, 15, p. 803, 1974

General Description

Dimethyl carbonate appears as a clear, colorless liquid with a pleasant odor. Denser than water and slightly soluble in water. Vapors are heavier than air. Used to make other chemicals and as a special purpose solvent.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Dimethyl carbonate reacts with acids to liberate heat along with methanol and carbon dioxide. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides.

Hazard

Flammable, dangerous fire risk. Toxic by inhalation, strong irritant.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highly flammable

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An irritant. Violent reaction or ignition on contact with potassium-tertbutoxide. A very dangerous fire hazard when exposed to heat, open flames (sparks), or oxiduers. To fight fire, use alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

If the reagent has broad intense bands at 3300cm-1 and above (i.e. OH stretching), then it should be purified further. Wash it successively with 10% Na2CO3 solution, saturated CaCl2, H2O, and dry it by shaking mechanically for 1hour with anhydrous CaCl2, and fractionate. [Bowden & Butler J Chem Soc 78 1939, Vogel J Chem Soc 1847 1948, Beilstein 3 IV 3.]

Dimethyl carbonate Preparation Products And Raw materials

Raw materials

CARBON MONOXIDE Petrochemical Ethylene carbonate Methyl chloroformate PHOSGENE Methanol Propylene carbonate Propylene oxide

Preparation Products

Boron trifluoride-DiMethyl carbonate coMplex (1,3,5-TRIMETHYL-1H-PYRAZOL-4-YL)METHYLAMINE 1-Methylimidazole 4-DIMETHOXYMETHYL-6-HYDROXYPYRIMIDINE-2-THIOL N-Methyl-3-carbomethoxy-4-piperidone hydrochloride DIMETHYL METHOXYMALONATE Asulam Ethyl methyl carbonate 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid 1H-Azepine-3-carboxylicacid,hexahydro-,methylester(9CI) Ciprofloxacin 1,3,5-Trimethyl-1H-pyrazole-4-carboxaldehyde 4-Bromo-1,3,5-trimethyl-1H-pyrazole 1,3,5-Trimethylpyrazole 1H-Pyrazole-4-carbonyl chloride, 1,3,5-trimethyl- (9CI) Diethyl carbonate 1,5-Diphenylcarbazide 2-PHENYLMALONAMIDE
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View Lastest Price from Dimethyl carbonate manufacturers

Hebei Jingbo New Material Technology Co., Ltd
Product
Dimethyl carbonate 616-38-6
Price
US $8.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000
Release date
2023-12-29
Hebei Weibang Biotechnology Co., Ltd
Product
Dimethyl Carbonate 616-38-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-01
Qingdao RENAS Polymer Material Co., Ltd.
Product
Dimethyl carbonate 616-38-6
Price
US $0.00/kg
Min. Order
20kg
Purity
99.0%
Supply Ability
20 tons
Release date
2024-07-02

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