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