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Dimethyl carbonate

Dimethyl carbonate structure

Dimethyl carbonate 

structure
  • CAS No:

    616-38-6

  • Formula:

    C3H6O3

  • Chemical Name:

    Dimethyl carbonate

  • Synonyms:

    Carbonic acid,dimethyl ester;Dimethyl carbonate;Methyl carbonate ((MeO)2CO);Methyl carbonate;NSC 9371;AK 100;AK 100 (carbonate)

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the US. Dimethyl carbonate is often considered to be a green reagent.


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.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


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.|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℃, b.p. 90℃) 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.

Dimethyl carbonate Basic Attributes

90.0779

90.0317

210-478-4

KE9J097SPN

1080

9371

1161

DTXSID9029192

Colorless liquid

2920909090

Characteristics

35.53

0.3992

colourless liquid

1.069

41674ºC

90ºC

18ºC

1.3672-1.3692

In water, 1.38X10+5 mg/L at 25 °C (est)|Miscible with alcohol and ether|Miscible with acids and alkalies; stable in the presence of water; soluble in most organic solvents|Soluble in oxygenated solvents|Solubility in water: none

Flammables area

55.40 mmHg|55.364 mm Hg at 25 °C|Vapor pressure, kPa at 25 °C: 7.4

Relative vapor density (air = 1): 3.1

Pleasant odor

3.10e-13 cm3/molecule*sec

Henry's Law constant = 6.2X10-4 atm-cu m/mol at 25 °C (est)

MP also listed as 4 °C|BP also stated as 89.7 °C|Hydroxyl radical reaction rate constant = 0.4352X10-12 cu cm/molecule-sec at 25 °C (est)

Highly flammable. Slightly soluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Highly Flammable

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.

458 °C

The vapour is heavier than air and may travel along the ground; distant ignition possible. The vapour mixes well with air, explosive mixtures are easily formed.

3.8363X10+7 J/Kmol at 273.15 K

Critical temperature: 548.00 K; Critical pressure: 4.5X10+6 Pa

Safety Information

II

3

1

R11

FG0450000

F

Stable. Highly flammable. Incompatible with strong oxidizing agents, potassium t-butoxide.

S16-S9

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Vapor/air mixtures are explosive.|Violent reaction or ignition on contact with potassium tert-butoxide.

UN 1161

P210; P370 + P378; P403 + P235

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Highly flammable. Vapour/air mixtures are explosive.|Flammable - 3rd degree, Reactive - 1st degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|Aggregated GHS information provided by 904 companies from 7 notifications to the ECHA C&L Inventory.|Warning|H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P261, P271, P280, P281, P303+P361+P353, P304+P340, P308+P313, P312, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Protective gloves. Wear safety goggles.

A very dangerous fire hazard when exposed to heat, open flames (sparks), or oxidizers.

Explosive limits, vol% in air: 4.2-12.9|Explosive limits , vol% in air: 4.2-12.9

Explosion: In case of fire: keep drums, etc., cool by spraying with water.|Use water spray, dry chemical, foam, or carbon dioxide. Water may be ineffective. Use water spray to keep fire-exposed containers cool.

Use water spray to cool and disperse vapors and protect personnel. Control runoff and isolate discharged material for proper disposal.|Personal protection: filter respirator for organic gases and vapors adapted to the airborne concentration of the substance. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Impervious clothing., Flame retardant antistatic protective clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|NO open flames, NO sparks and NO smoking. NO contact with oxidizing agents.|For more Preventive Measures (Complete) data for DIMETHYL CARBONATE (8 total), please visit the HSDB record page.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: 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.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for DIMETHYL CARBONATE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Irritating to skin, eye, and respiratory system.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Fireproof. Separated from strong oxidants. Well closed. Store in an area without drain or sewer access.

The vapour is mildly irritating to the eyes.

NO open flames, NO sparks and NO smoking. NO contact with oxidizing agents. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling. Use non-sparking handtools.

Use ventilation.

Protective gloves.

Wear safety goggles.

Air Quality: Revision to Definition of Volatile Organic Compounds--Exclusion of Propylene Carbonate and Dimethyl Carbonate. This action revises EPA's definition of volatile organic compounds (VOCs) for purposes of preparing state implementation plans (SIPs) to attain the national ambient air quality standard for ozone under Title I of the Clean Air Act (Act). This revision adds the compounds propylene carbonate and dimethyl carbonate to the list of compounds which are excluded from the definition of VOC on the basis that these compounds make a negligible contribution to tropospheric ozone formation.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Toxicity

LD50 Mouse ip 800 mg/kg|LD50 Mouse oral 6 g/kg|LD50 Rat oral 13 g/kg|LD50 Rat inhalation > or = 140 mg/L/4 hours|For more Non-Human Toxicity Values (Complete) data for DIMETHYL CARBONATE (7 total), please visit the HSDB record page.

Dimethyl carbonate's production and use as an environmentally benign methylating agent(1,2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.9 (SRC), determined from a structure estimation method(2), indicates that dimethyl carbonate is expected to have very high mobility in soil(SRC). Volatilization of dimethyl carbonate from moist soil surfaces may be expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.2X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dimethyl carbonate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 55.364 mm Hg at 25 °C(4). A >90% biodegradation using activated sludge in the OECD Modified MITI test(5) indicates that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.9(SRC), determined from a structure estimation method(2), indicates that dimethyl carbonate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 6.2X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.9 hours and 4.2 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.23(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A >90% biodegradation using activated sludge in the OECD Modified MITI test(7) indicates that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl carbonate, which has a vapor pressure of 55 mm Hg at 25 °C (2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl carbonate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 24.6 days(SRC), calculated from its rate constant of 0.44X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dimethyl carbonate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of dimethyl carbonate with photochemically-produced hydroxyl radicals has been estimated as 0.44X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 24.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The alkyl carbonate esters hydrolyze very slowly in water when compared to the chloroformates. Under alkaline conditions, the rates of hydrolysis are similar to those of the corresponding acetic acid esters. The net result is the formation of hydroxy compounds and carbon dioxide(2). Dimethyl carbonate does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3.2 was calculated in fish for dimethyl carbonate(SRC), using an estimated log Kow of 0.23(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dimethyl carbonate can be estimated to be 2.9 (SRC). According to a classification scheme(2), this estimated Koc value suggests that dimethyl carbonate is expected to have very high mobility in soil.

The Henry's Law constant for dimethyl carbonate is estimated as 6.2X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethyl carbonate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 1.9 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4.2 days(SRC). Dimethyl carbonate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dimethyl carbonate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 55.364 mm Hg at 25 °C(3).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of dimethyl carbonate is 100 to 999; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,725 workers (0 of these were female) were potentially exposed to dimethyl carbonate in the US(1). Occupational exposure to dimethyl carbonate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl carbonate is produced or used.

Drug Information

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: 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. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)


Fresh air, rest.


Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Provide a low-stimulus environment. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Treat frostbite by rapid rewarming ... . /Esters and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

dimethyl carbonate

Cough.


Redness.

Dimethyl carbonate Use and Manufacturing

Methods of Manufacturing

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.|Dimethyl carbonate is also manufactured by carbonylation of methylnitrite through a catalytic redox process. The process is practiced commercially in the gas phase by Ube Industries, LTD., Japan using a palladium supported catalyst system.

Uses

Component in Li-ion electrolyte


Adhesives and sealants

Production

10,000,000 - 50,000,000 lb|Carbonic acid, dimethyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Carbonic acid, dimethyl ester. Aggregated National Production Volume: 1 to < 10 million lbs.|Production volume for non-confidential chemicals reported under the 2012 Chemical Data Reporting Rule. Chemical: Carbonic acid, dimethyl ester. Aggregated National Production Volume: 17,917,274 lb/yr.

Grade: Technical

Adhesive manufacturing|Carbonic acid, dimethyl ester: ACTIVE|DMCD was considered acceptable for use as a cold sterilizing agent for beverages when used in accordance with Good Manufacturing Practice up to a maximum of 25 mg/L.

Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Normal alkane RI, non-polar column, custom temperature program Capillary HP-5 620. custom temperature program 60. m/0.25 mm/0.25 μm, Helium; Program: 30 0C (2 min) 2 0Cmin -> 60 0C 10 0C/min -> 100 0C 20 0C/min -> 140 0C 10 0C/min -> 200 0C (10 min) Rotsatschakul, P.Visesanguan, W.Smitinont, T.Chaiseri, S.Changes in volatile compounds during fermentation of nham (Thai fermented sausage)Int. Food Res. J.2009, 16, 391-414.

Computed Properties

Molecular Weight:90.08
XLogP3:0.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:90.031694049
Monoisotopic Mass:90.031694049
Topological Polar Surface Area:35.5
Heavy Atom Count:6
Complexity:44
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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  • Data: 2026-07-31
  • Price: 4350.00Yuan/mt
  • Change: 33.33

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