Dimethyl carbonate

Dimethyl carbonate - Names and Identifiers

Name	Dimethyl carbonate
Synonyms	DMC Methyl carbonate METHYL CARBONATE dimetyl carbonate DIMETHYL CARBONATE Dimethyl carbonate methylcarbonate((meo)2co) Carbonic acid dimethyl ester CARBONIC ACID DIMETHYL ESTER DIMETHYL CARBONATE, ANHYDROUS DimethylCarbonateForSynthesis DIMETHYL CARBONATE, REAGENTPLUS
CAS	616-38-6
EINECS	210-478-4
InChI	InChI=1/C3H6O3/c1-5-3(4)6-2/h1-2H3
InChIKey	IEJIGPNLZYLLBP-UHFFFAOYSA-N

Dimethyl carbonate - Physico-chemical Properties

Molecular Formula	C3H6O3
Molar Mass	90.08
Density	1.069 g/mL at 25 °C (lit.)
Melting Point	2-4 °C (lit.)
Boling Point	90 °C (lit.)
Flash Point	65°F
Water Solubility	139 g/L
Solubility	139g/l
Vapor Presure	18 mm Hg ( 21.1 °C)
Vapor Density	3.1 (vs air)
Appearance	Liquid
Color	<50(APHA)
Odor	Pleasant
Merck	14,3241
BRN	635821
Storage Condition	Store below +30°C.
Stability	Stable. Highly flammable. Incompatible with strong oxidizing agents, potassium t-butoxide.
Sensitive	Moisture Sensitive
Explosive Limit	4.22-12.87%(V)
Refractive Index	n20/D 1.368(lit.)
Physical and Chemical Properties	Characteristics of colorless transparent liquid, irritating odor. properties is an important organic synthesis intermediates, molecular structure containing carbonyl, methyl and methoxy functional groups, with a variety of reaction properties, in the production of safe and convenient, characteristics of less pollution and easy transportation
Use	Used in chemical synthesis of methylating agent and carbonylating agent, widely used in food antioxidants, plant protection agents and other fields

Dimethyl carbonate - Risk and Safety

Hazard Symbols	F - Flammable
Risk Codes	11 - Highly Flammable
Safety Description	S9 - Keep container in a well-ventilated place. S16 - Keep away from sources of ignition. S2017/9/16 -
UN IDs	UN 1161 3/PG 2
WGK Germany	1
RTECS	FG0450000
TSCA	Yes
HS Code	2920 90 10
Hazard Class	3
Packing Group	II
Toxicity	LD50 in rats (g/kg): 13.8 orally; 2.5 dermally; LC50 (4 hr) in rats (mg/l): 140 by inhalation (Ono)

Dimethyl carbonate - Upstream Downstream Industry

Raw Materials	Propylene oxide Methyl alcohol Propylene carbonate
Downstream Products	Diethyl carbonate Methyl ethyl carbonate asulam Ciprofloxacin

Dimethyl carbonate - Nature

Open Data Verified Data

colorless transparent liquid with pungent odor. The relative density was 1.073. The melting point was 2-4 °c. Boiling point 90.2 °c. Refractive index 3697. Flash point (Open Cup) 21.7 °c. Viscosity 0.664MPA. s. Insoluble in water, soluble in ethanol, ether and other organic solvents.

Last Update：2024-01-02 23:10:35

Dimethyl carbonate - Preparation Method

Open Data Verified Data

transesterification method dimethyl carbonate can be obtained by performing a transesterification reaction of ethylene carbonate or propylene carbonate with methanol. This method has high yield, small equipment corrosion and mild reaction conditions, but the source of raw materials is restricted by the development of petrochemical industry and the utilization rate of elements is low.
oxidative carbonylation of methanol, carbon monoxide and oxygen in the presence of a catalyst in the direct synthesis of dimethyl carbonate. This method is the most promising method with cheap raw materials, low toxicity and simple process. According to the classification of process conditions, can be divided into liquid phase method and gas phase method, gas phase method can be divided into one-step method and two-step method. Among them, the two-step method of liquid phase oxidative carbonylation of methanol and gas phase oxidative carbonylation has been industrialized, while the one-step method of gas phase oxidative carbonylation of methanol is still under development.
synthesis of methanol with CO2
synthesis of methanol and urea by reaction

Last Update：2022-01-01 10:33:53

Dimethyl carbonate - Use

Open Data Verified Data

dimethyl carbonate can replace the traditional use of toxic raw materials such as phosgene, dimethyl sulfate and methyl chloride. Can be used for non-phosgene synthesis of polycarbonate, diphenyl carbonate, isocyanate and allyl diethylene glycol carbonate; For the synthesis of various carbamate pesticides, such as carbaryl; Organic synthesis intermediates, such as anisole, alkyl Arylamine, symmetrical diaminourea, methyl formate, etc.; Pharmaceutical industry, can be used for the production of amino oxazolidinone, ciprofloxacin, p ketone carboxylic acid ester pharmaceutical intermediates. In addition, it can also be used as gasoline, diesel additives, refrigerator oil and solvents.

Last Update：2022-01-01 10:33:52

Dimethyl carbonate - Safety

Open Data Verified Data

This product is a non-toxic chemical. On the eyes, skin, mucous membranes have mild irritation. The oral LD50 of rats was 6.4-12. 8 g/kg. The raw material phosgene used in the phosgene process is highly toxic, and the equipment must be strictly sealed, the ventilation should be strengthened, and the operators should wear all kinds of protective equipment.
This product is packaged in an iron drum. This product is flammable, and the contact with the oxidant can cause combustion, should be stored in a cool and ventilated special warehouse, away from the fire source. To prevent the leakage of packaging container damage. According to the provisions of flammable and toxic hazardous chemicals storage and transportation.

Last Update：2022-01-01 10:33:53

Dimethyl carbonate - Nature

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	18mm Hg ( 21.1 °C)
refractive index	n20/D 1.368(lit.)
flash point	65 °F
storage conditions	Store below +30°C.
solubility	139g/l
morphology	Liquid
color	<50(APHA)
Odor	Pleasant
explosion limit value (explosive limit)	4.22-12.87%(V)
water solubility	139 g/L
sensitivity	Moisture Sensitive
Merck	14,3241
BRN	635821
stability	Stable. Highly flammable. Incompatible with strong oxidizing agents, potassium t-butoxide.
InChIKey	IEJIGPNLZYLLBP-UHFFFAOYSA-N
NIST chemical information	Carbonic acid, dimethyl ester(616-38-6)
EPA chemical information	Carbonic acid, dimethyl ester (616-38-6)

Last Update：2024-04-10 22:29:15

Dimethyl carbonate - Reference standard

index name battery-grade superior products first-grade qualified products experimental method
Appearance, Appearance colorless and transparent body, colorless and transparent liquid
Dimethyl carbonate content, DMC content% ≥ 99.9 ≥ 99.5 ≥ 99.0 ≥ 98.5 gas chromatography
Water, Water Content% ≤ 30ppm ≤ 0.10 ≤ 0.10 ≤ 0.10 GB606
Alkalinity (0H),Alkalinity mmol/10Og - ≤ 0.10 ≤ 0.12 ≤ 0.12 Q/GNPC-JX 017
Non-volatile, Non-volatile matter % - ≤ 0.02 ≤ 0.02 ≤ 0.02 GB6324.2
Peroxide (calculated as H2O2),Peroxide(By H2O2) ≤ 5ppm --- GB6016-85
Density (20 ℃),Density g/cm3 1.071±0.005

Last Update：2024-04-10 21:08:14

Dimethyl carbonate - Use

Dimethyl carbonate (DMC) has a unique molecular structure (CH3O-CO-OCH3). Its molecular structure contains carbonyl, methyl, methoxy and carbonyl methoxy, so it can be widely used in carbonylation, Methylation, methoxylation and carbonyl methylation and other organic synthesis reactions, so it has a very wide range of uses, mainly used as carbonylation and methylation reagents, gasoline additives, raw materials for the synthesis of polycarbonate (PC). The large-scale production of DMC was developed along with the non-phosgene synthesis process of polycarbonate.
1. A new type of low-toxic solvent can replace toluene, xylene, ethyl acetate, butyl acetate, acetone or butanone and other solvents in the paint and adhesive industry. It is an environmentally friendly green chemical product.
2. Good methylating agent, carbonylation agent, hydroxymethylating agent and methoxylating agent are a chemical raw material with a wide range of uses.
3, phosgene, dimethyl sulfate, methyl chloroformate and other drugs ideal substitutes.
4. Synthesis of polycarbonate, diphenyl carbonate, isocyanate, etc.
5. Medicine is used to synthesize anti-infective drugs, antipyretic and analgesic drugs, vitamin drugs, and central nervous system drugs.
6. Pesticides are mainly used to produce methyl isocyanate, and then to produce certain carbamate drugs and pesticides (anisole).
7. Gasoline additives, lithium battery electrolyte, etc.

Last Update：2024-04-10 21:08:33

Dimethyl carbonate - Production method

1. It is obtained by reacting methyl chloroformate ([79-22-1]) with methanol. The raw material methyl chloroformate used in the reaction is obtained by the reaction of methanol and phosgene. During preparation, this phosgenation product can also be added without separation and excess methanol reflux reaction to synthesize dimethyl carbonate. The above reaction is called the traditional phosgene method.

2. The transesterification method uses ethylene carbonate or propylene carbonate and methanol for transesterification to produce dimethyl carbonate. This method has high yield, low corrosion of equipment and mild reaction conditions, but the source of raw materials is restricted by the development of petrochemical industry and the utilization rate of elements is low.

3. Oxidative carbonylation of methanol, carbon monoxide and oxygen directly synthesize dimethyl carbonate under the action of a catalyst. This method is the most promising method with cheap raw materials, low toxicity and simple process. According to the classification of process conditions, it can be divided into liquid phase method and gas phase method, and gas phase method can be divided into one-step method and two-step method. Among them, the two-step method of methanol liquid phase oxidative carbonylation and gas phase oxidative carbonylation has been industrialized, while the one-step method of methanol gas phase oxidative carbonylation is still under development.

4. Reaction synthesis of methanol and CO2. This route is still under development. 5. Methanol and urea reaction synthesis method. This route is still under development.

Last Update：2024-04-10 21:09:09

Dimethyl carbonate - Security information

category	flammable liquid
toxicity classification	low toxicity
acute toxicity	oral-rat LD50: 13000 hok/kg; Oral-mouse LD50: 6000 mg/kg
flammability hazard characteristics	it is flammable in case of open flame, high temperature and oxidant; combustion produces stimulating smoke
storage and transportation characteristics	The warehouse is ventilated and dry at low temperature; stored separately from the oxidant
fire extinguishing agent	dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent

security information

dangerous goods mark	F
hazard category code	11
safety instructions	9-16-2017/9/16
dangerous goods transport number	UN 1161 3/PG 2
WGK Germany	1
RTECS number	FG0450000
auto-ignition temperature	458 °C
TSCA	Yes
customs code	2920 90 10
HazardClass	3
PackingGroup	II
toxic substance 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)

Last Update：2024-04-10 21:09:51

Dimethyl carbonate - Introduction

dimethyl carbonate is abbreviated as DMC. it is a colorless, transparent and pungent liquid at normal temperature. its relative density (d204) is 1.0694, melting point is 4 ℃, boiling point is 90.3 ℃, flash point is 21.7 ℃ (opening) is 16.7 ℃ (closed), refractive index (nd20) is 1.3687, flammable and non-toxic. It can be mixed with almost all organic solvents such as alcohols, ketones, esters, etc. in any proportion, and is slightly soluble in water. It can be used as a methylation reagent. Compared with other methylation reagents, such as methyl iodide and dimethyl sulfate, dimethyl carbonate is less toxic and can be biodegraded.
In the past, the method of using phosgene as raw material to prepare dimethyl carbonate is not commonly used. Instead, it is prepared by the catalytic oxidative carbonylation reaction of methanol in the presence of oxygen, which is more environmentally friendly than the previous method.
Dimethyl carbonate can methylate aniline, phenol and carboxylic acid, but many reactions require high pressure. DBU can be added when refluxing DMC to catalyze the reaction of dimethyl carbonate methylated carboxylic acid

Last Update：2024-04-09 20:52:54

Dimethyl carbonate - Reference Information

LogP	0.23-0.354 at 20-25℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
overview	dimethyl carbonate is abbreviated as DMC. it is a colorless, transparent and pungent liquid at normal temperature. its relative density (d204) is 1.0694, melting point is 4 ℃, boiling point is 90.3 ℃, flash point is 21.7 ℃ (opening) is 16.7 ℃ (closed), refractive index (nd20) is 1.3687, flammable and nontoxic. It can be mixed with almost all organic solvents such as alcohols, ketones, esters, etc. in any proportion, and is slightly soluble in water. It can be used as a methylation reagent. Compared with other methylation reagents, such as methyl iodide and dimethyl sulfate, dimethyl carbonate is less toxic and can be biodegraded. In the past, the method of using phosgene as raw material to prepare dimethyl carbonate is not commonly used. Instead, it is prepared by the catalytic oxidative carbonylation reaction of methanol in the presence of oxygen, which is more environmentally friendly than the previous method. Dimethyl carbonate can methylate aniline, phenol and carboxylic acid, but many reactions require high pressure. DBU can be added when refluxing DMC to catalyze the reaction of dimethyl carbonate methylated carboxylic acid:
reference quality standard	index name battery grade superior grade first grade qualified product experimental method appearance, Appearance colorless transparent body, colorless and transparent liquid dimethyl carbonate content, DMC content% ≥ 99.9 ≥ 99.5 ≥ 99.0 ≥ 98.5 gas chromatography moisture, Water Content% ≤ 30ppm ≤ 0.10 ≤ 0.10 ≤ 0.10 GB606 alkalinity (0H), alkalinity mmol/10Og - ≤ 0.10 ≤ 0.12 ≤ 0.12 Q/GNPC-JX 017 non-volatile, Non-volatile matter % - ≤ 0.02 ≤ 0.02 ≤ 0.02 GB6324.2 peroxide (based on H2O2),Peroxide(By H2O2) ≤ 5ppm-GB6016-85 density (20 ℃),Density g/cm3 1.071±0.005
Uses	Dimethyl carbonate (DMC) has a unique molecular structure (CH3O-CO-OCH3), and its molecular structure contains carbonyl, methyl, methoxy and carbonyl methoxy, so it can be widely used in organic synthesis reactions such as carbonylation, methylation, methoxylation and carbonyl methylation. It has a very wide range of uses, mainly used as carbonylation and methylation reagents, gasoline additives, raw materials for the synthesis of polycarbonate (PC), etc. The large-scale production of DMC was developed along with the non-phosgene synthesis process of polycarbonate. Its uses are as follows: 1. A new type of low-toxic solvent can replace toluene, xylene, ethyl acetate, butyl acetate, acetone or butanone and other solvents in the paint and adhesive industry. It is an environmentally friendly green chemical product. 2. Good methylating agent, carbonylation agent, hydroxymethylating agent and methoxylating agent are widely used in food antioxidants, plant protection agents and other fields. It is a widely used chemical raw material. 3. An ideal substitute for severe drugs such as phosgene, dimethyl sulfate and methyl chloroformate. 4. Synthesis of polycarbonate, diphenyl carbonate, isocyanate, etc. 5. In medicine, it is used to synthesize anti-infective drugs, antipyretic and analgesic drugs, vitamin drugs and central nervous system drugs. 6. Pesticides are mainly used to produce methyl isocyanates, and then to produce certain carbamate drugs and pesticides (anisole). 7. Gasoline additives, lithium battery electrolyte, etc.
market situation	dimethyl carbonate mainly has 3 categories: industrial grade, medical grade and battery grade. Among them, the industrial grade dimethyl carbonate accounts for more than half of the market share. These produced dimethyl carbonate are mainly used to produce polycarbonate and electrolyte solvents. The foreign production process of dimethyl carbonate is mainly gas phase oxidative carbonylation and liquid phase oxidative carbonylation. The domestic processes are mainly PO transesterification, two-step urea, one-step urea, coal-to-ethylene glycol, methanol carbonyl oxidation and EO transesterification. Sabic Spain in Spain, Bayer in Germany and Lotte in South Korea are major producers in the dimethyl carbonate market. In 2019, they produced the world's 33.45% dimethyl carbonate. The products are basically self-produced and self-produced. The development of dimethyl carbonate in China is relatively stable. In 2020, China's dimethyl carbonate production capacity will account for the 58% of the world. Shida Shenghua invested in the construction of dimethyl carbonate production capacity to 175,000 tons in 2019, maintaining the leading position of domestic dimethyl carbonate production. Anhui Zhongyan Red Sifang and Taiwan Chi Mei followed. From a regional point of view, the output of dimethyl carbonate in China accounts for more than half of the global market, but the technology is relatively backward, the capacity utilization rate of products is low, and the price of dimethyl carbonate produced is lower than the global average price. The United States is the second largest producer of dimethyl carbonate. It is estimated that the output in 2020 will be less than 1/4 of that in China, but the price of its products is relatively high. Now the major manufacturers in the Chinese market occupy an important position in the international market, in the future, we need to upgrade our technology level to stabilize our market leading position.
Preparation	Using methanol, carbon monoxide, oxygen and chlorine-containing organic matter as raw materials, and activated carbon supported PdCl2-CuCl2-CH3COOK as catalyst, gas phase catalytic synthesis of dimethyl carbonate and azeotropic distillation separation products, Its characteristics are:(1) The mixture of catalyst and quartz sand is loaded into a tubular reactor, under a nitrogen gas atmosphere, the catalyst bed in the reactor is heated to 130-170 ℃;(2) The molar percentage of raw materials composed of carbon monoxide 25-50%, oxygen 8-20%, methanol 40-65% and 1-5% of chlorine-containing organic matter is preheated to 120-170 ℃ by preheater;(3) The material from the preheater enters the tubular reactor from the upper end of the reactor, and the gas phase space velocity of the material is 1800-8000h-1, (4) The material from the reactor is condensed by the condenser into a gas-liquid two-phase, the gas phase is recycled, the liquid phase enters the azeotropic distillation column in the middle of the azeotropic distillation column, and the chlorinated organic matter in the raw material is used as the azeotropic agent to obtain the dimethyl carbonate product in the azeotropic distillation column; the chlorine-containing organic matter is selected from dichloromethane, trichloromethane, chloroethane, dichloroethane, trichloroethane, trichloroethylene, perchloroethylene, carbon tetrachloride.
Production method	It is obtained by reacting methyl chloroformate with methanol. The raw material methyl chloroformate used in the reaction is obtained by the reaction of methanol and phosgene. During preparation, this phosgenation product can also be added without separation, and excessive methanol reflux reaction can be added to synthesize dimethyl carbonate. The above reaction is called the traditional phosgene method. By transesterification, dimethyl carbonate can be prepared by transesterification reaction between ethylene carbonate or propylene carbonate and methanol. This method has high yield, low equipment corrosion and mild reaction conditions, but the source of raw materials is restricted by the development of petrochemical industry and the utilization rate of elements is low. Oxidative carbonylation of methanol, carbon monoxide and oxygen directly synthesize dimethyl carbonate under the action of a catalyst. This method is the most promising method with cheap raw materials, low toxicity and simple process. According to the classification of process conditions, it can be divided into liquid phase method and gas phase method, and gas phase method can be divided into one-step method and two-step method. Among them, the two-step method of methanol liquid phase oxidative carbonylation and gas phase oxidative carbonylation has been industrialized, while the one-step method of methanol gas phase oxidative carbonylation is still under development. Reaction synthesis of methanol and CO2. This route is still under development. Reaction synthesis of methanol and urea. This route is still under development.
category	flammable liquid
toxicity classification	low toxicity
acute toxicity	oral administration-rat LD50: 13000 hock/kg; Oral administration-mouse LD50: 6000 mg/kg
flammability hazard characteristics	flammability in case of open flame, high temperature and oxidant; Combustion produces stimulating smoke
storage and transportation characteristics	warehouse ventilation and low temperature drying; separate from oxidant
fire extinguishing agent	dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent
spontaneous combustion temperature	458°C
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)