Dimethyl dicarbonate

Clear, colorless liquid

Colorless liquid

Soluble in water with decomposition; miscible with toluene

dec.

BP: 44-47 °C at 5 mm Hg

45.00 to 46.00 °C. @ 5.00 mm Hg

Hazardous decomposition products: By Fire and Thermal Decomposition: Methanol; Carbon oxides, nitrogen oxides (NOx), other potentially toxic fumes.

When heated to decomposition it emits acrid smoke and irritating fumes.

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

Colourless liquid, decomposes in aqueous solution. It is corrosive to skin and eyes and toxic by inhalation and ingestion

Liquid

Danger

H226 (23.6%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 106 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Dicarbonic acid, dimethyl ester

Regulation (EC) No 1333/2008 (amended)

Dicarbonic acid, dimethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Dimethyl dicarbonate (CAS Reg. No. 4525-33-1) may be safely used in food in accordance with the following prescribed conditions: (a) The additive meets the following specifications: (1) The additive has a purity of not less than 99.8 percent ... (2) The additive contains not more than 2,000 ppm (0.2 percent) dimethyl carbonate. ... (b) The additive is used or intended for use as a microbial control agent in the following beverages under normal circumstances of bottling, canning, or other forms of final packaging, where the viable microbial load has been reduced to 500 microorganisms per milliliter or less by current good manufacturing practices such as heat treatment, filtration, or other technologies prior to the use of dimethyl dicarbonate: (1) In wine, dealcoholized wine, and low alcohol wine in an amount not to exceed 200 parts per million. (2) In ready-to-drink teas in an amount not to exceed 250 parts per million. (3) In carbonated or noncarbonated, nonjuice-containing (less than or equal to 1 percent juice), flavored or unflavored beverages containing added electrolytes (5-20 milliequivalents/liter sodium ion (Na+) and 3-7 milliequivalents/liter potassium ion (K+)) in an amount not to exceed 250 parts per million. (4) In carbonated, dilute beverages containing juice, fruit flavor, or both, with juice content not to exceed 50 percent, in an amount not to exceed 250 parts per million.

The skin-irritant effects of dimethyldicarbonate (DMDC) were investigated in 6 white New Zealand rabbits of both sexes with body weights of 3-4 kg. Approximately 0.5 mL of the substance were applied to the shaved skin of every animal. Exposure times were 30 min or 4 hr. At the end of the exposure period, skin areas were washed and dried. Skin changes were recorded at 24, 48, and 72 hr, as well as 7 days after the start of the exposure. After an exposure for both 30 min and 4 hr, scale formation and necroses passing beyond the application area were observed. The skin reactions were not reversible within the 7 day follow-up observation period. Consequently, DMDC proved to be highly irritant and corrosive to rabbit skin.

Introduction of dimethyldicarbonate (DMDC) into the conjunctival sac of rabbits caused considerable irritation. The cornea was still entirely cloudy after 7 days.

Suitable Extinguishing Media: All extinguishing media are suitable. Special Fire Fighting Procedures: Firefighters should be equipped with self-contained breathing apparatus to protect against potentially toxic and irritating fumes. Use cold water spray to cool fire-exposed containers to minimize risk of rupture.

Storage Temperature: minimum: 20 °C (68 °F); maximum: 30 °C (86 °F). Storage Period: 12 Months: Keep in a dry place. Expiration date on label is day/month/year. Handling/Storage Precautions: Do not breathe vapors or spray mist. Do not get on skin or clothing. Do not get in eyes. Do not taste or swallow. Use only with adequate ventilation/personal protection. Wash thoroughly after handling. Keep container closed when not in use. Store in a dry place away from excessive heat in original or similar containers. Protect from freezing. Further Info on Storage Conditions: Avoid extreme heat. Product can react with water. Avoid contact with moisture/water. Light sensitive. If the material does crystallize, it must be reliquified before being used. The recommended method to reliquify is to simply place the container in an appropriate storage area and allow it to gradually reach ambient temperatures. An alternative is to reliquify by gently heating it in a water bath. Do NOT apply heat/flame directly to container.

Spill and Leak Procedures: Cleanup personnel must use appropriate personal protective equipment. Do not allow spilled material or wash water to enter sewers, surface waters, or groundwater systems. Remove all sources of ignition, including flames, heat, and sparks. Ventilate area to remove vapors or dust. Evacuate and keep unnecessary people out of spill area. Cover spill with damp, fluid-binding material (for example, sand, sawdust, chemical binder based on calcium silicate hydrate). Transfer to an open waste container after approximately one hour, cover loosely and remove to an isolated area. Do not seal the container as carbon dioxide given off by the slow reaction between Velcorin and water may cause a tightly sealed container to burst. Flush the spill with cold water but avoid flushing into open drains. Hot water should never be used for this purpose since it would cause considerable vaporization of the spilled material. Use the paper Velcorin indicator strips to insure that there is no residual Dimethyl Dicarbonate in the air.

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.

Empty Container Precautions: Recondition or dispose of empty container in accordance with governmental regulations. Do not reuse empty container without proper cleaning. Label precautions also apply to this container when empty. Empty containers retain product residue (dust, liquid, vapor and/or gases) and can be dangerous. Remove empty bottle from automatic metering system to a well-ventilated area (outdoors is also suitable). Fill bottle carefully with water to the brim so as to avoid overflow. Do not tighten the screw lid back on the container due to possible pressurization from evolution of carbon dioxide. After 24 hours of standing, the water containing the hydrolyzed products of the residual amount of Velcorin can be added to the plant's waste water. The bottle may then be disposed of like any other glass container. Soiled empty containers are to be treated in the same manner.

Hand Protection: PVC disposable gloves, Nitrile rubber gloves. After each use, immerse in cold water and discard. Eye Protection: Chemical resistant goggles must be worn. Chemical safety goggles in combination with a full face shield if a splash hazard exists. Skin and body protection: Permeation resistant clothing and foot protection. Wash carefully in cold water immediately after use.

Respiratory Protection: The odor of Velcorin can not be used as a warning property againt inhalation exposure. Air concentrations of Velcorin should not be allowed to exceed 0.04 ppm, even momentarily. A NIOSH approved airpurifying organic vapor respirator must be used when Velcorin concentrations are between >0.04 ppm and <10 ppm and during disposal. Positive pressure air-supplied respirators if concentrations are unknown or exceed 10 ppm or if the workspace is confined and unventilated. Use air-supplied respirators or selfcontained breathing apparatus in emergency situations. Observe OSHA regulations for respirator use. The metering equipment, particularly the cabinet in which the bottle is kept, should be enclosed. The room housing the equipment should have adequate general room ventilation.

Industrial Hygiene/Ventilation Measures: Use local and general exhaust ventilation to control levels of exposure.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that dimethyl dicarbonate is expected to have very high mobility in soil(SRC). Volatilization of dimethyl dicarbonate from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dimethyl dicarbonate is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.46 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2013); however, structurally similar dimethyl cabonate was >90% biodegraded in the Modified MITI test(4), suggesting 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 1(SRC), determined from a structure estimation method(2), indicates that dimethyl dicarbonate 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 4.5X10-4 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 2.7 hours and 5.3 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -0.86(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Dimethyldicarbonate (DMDC) is unstable in aqueous solution and breaks down almost immediately after addition to beverages; principal breakdown products in wine and aqueous liquids are methanol and carbon dioxide(8). Biodegradation data in water were not available(SRC, 2013); however, structurally similar dimethyl carbonate was >90% biodegraded in the Modified MITI test(8), suggesting 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 dicarbonate, which has an estimated vapor pressure of 1.46 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor. Vapor-phase dimethyl dicarbonate 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 0.4352X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dimethyl dicarbonate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

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

An estimated BCF of 3.2 was calculated in fish for dimethyl dicarbonate(SRC), using an estimated log Kow of -0.86(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).

The Henry's Law constant for dimethyl dicarbonate is estimated as 4.5X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethyl dicarbonate 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 2.7 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 5.3 days(SRC). Dimethyl dicarbonate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dimethyl dicarbonate is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.46 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Acute Exposure/ Introduction of dimethyldicarbonate (DMDC) into the conjunctival sac of rabbits caused considerable irritation. The cornea was still entirely cloudy after 7 days.

/LABORATORY ANIMALS: Acute Exposure/ The skin-irritant effects of dimethyldicarbonate (DMDC) were investigated in 6 white New Zealand rabbits of both sexes with body weights of 3-4 kg. Approximately 0.5 mL of the substance were applied to the shaved skin of every animal. Exposure times were 30 min or 4 hr. At the end of the exposure period, skin areas were washed and dried. Skin changes were recorded at 24, 48, and 72 hr, as well as 7 days after the start of the exposure. After an exposure for both 30 min and 4 hr, scale formation and necroses passing beyond the application area were observed. The skin reactions were not reversible within the 7 day follow-up observation period. Consequently, DMDC proved to be highly irritant and corrosive to rabbit skin.

/LABORATORY ANIMALS: Acute Exposure/ Attachment of small pieces of wool holding 50 uL dimethyldicarbonate (DMDC) to the skin of rabbits caused swelling and reddening, which were still visible after 7 days.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The subchronic toxicity of dimethyldicarbonate (DMDC)-treated beverages was tested in Wistar (SPF) rats (28-32 days of age at the start of the experiment). Groups of 15 male and 15 female rats received orange juice, black currant juice, beer (lager type), or wine (Riesling) without (control groups) or with 4000 mg/L DMDC instead of drinking water for a period of 3 months. The animals were inspected daily. Body weights and food consumption were recorded weekly, drink consumption daily. Clinical chemical tests were performed on five rats of each sex for every group 1 and 3 months after the start of the experiment. Hematological parameters investigated were hemoglobin concentration, hematocrit, erythrocyte and leukocyte counts, mean cell hemoglobin (MCH), mean cell volume (MCV), the reticulocyte count, differential blood count, and, at the end of the experiment, thromboblastin time. Liver function was assessed by measurement of the activities of alkaline phosphatase (AP), glutamate-pyruvate-transaminase (GPT), glutamate-oxalacetate-transaminase (GOT), and glutamate dehydrogenase (GLDH), as well as the concentrations of bilirubin in the blood plasma. Kidney function was assessed by measurement of plasma urea and creatinine concentrations as well as by urinalysis. Blood glucose and cholesterol levels were also determined. Surviving animals were autopsied at the end of the experiment, animals that died earlier were autopsied immediately. Samples from 22 different tissues were fixed for histopathological examinations. Animals receiving DMDC showed no differences in appearance, behavior, or consumption of drink or food as compared to the corresponding controls. Body weight gain was not significantly different in animals receiving DMDC in comparison with the respective controls. Application of DMDC did not affect mortality. No significant differences in hematological parameters or in parameters of liver and kidney function were observed between rats receiving DMDC and their controls. Also, blood glucose and cholesterol concentrations remained within physiological ranges for all groups. On autopsy, no pathological changes attributable to the treatment were observed in any group. Only slight and randomly distributed differences in organ weights were seen. Histomorphological examination of fixed organs revealed no changes which were attributable to the administration of DMDC-treated drinks. It was concluded that 4000 mg DMDC/L in fruit juice or alcoholic beverage was tolerated by rats without signs of toxicity.

For more Non-Human Toxicity Excerpts (Complete) data for Dimethyl dicarbonate (9 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of dimethyl dicarbonate with photochemically-produced hydroxyl radicals has been estimated as 0.4352X10-12 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 dicarbonate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Occupational exposure to dimethyl dicarbonate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl dicarbonate is produced or used. Use data indicate that the general public may be exposed to dimethyl dicarbonate via ingestion of foods containing this preservative. (SRC)

Dimethyl dicarbonate's production and use as a preservative, in particular in wine and soft drinks, may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.46 mm Hg at 25 °C indicates dimethyl dicarbonate will exist solely as a vapor in the atmosphere. Vapor-phase dimethyl dicarbonate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 24.6 days. Dimethyl dicarbonate contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, dimethyl dicarbonate is expected to have very high mobility based upon an estimated Koc of 1. Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 4.5X10-4 atm-cu m/mole. Dimethyl dicarbonate may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data in soil or water were not available; however, structurally similar dimethyl cabonate was >90% biodegraded in the Modified MITI test, suggesting that biodegradation may be an important environmental fate process in soil and water. If released into water, dimethyl dicarbonate is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces may be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. 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. Occupational exposure to dimethyl dicarbonate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl dicarbonate is produced or used. Use data indicate that the general public may be exposed to dimethyl dicarbonate via ingestion of foods containing this preservative. Dimethyldicarbonate (DMDC) is unstable in aqueous solution and breaks down almost immediately after addition to beverages; principal breakdown products in wine and aqueous liquids are methanol and carbon dioxide. (SRC)

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/

LD50 Mouse (female) oral 752.7 mg/kg

LD50 Mouse (male) oral 906.5 mg/kg

LD50 Mouse (female) ip 44.5 mg/kg

LD50 Mouse (male) ip 44.9 mg/kg

For more Non-Human Toxicity Values (Complete) data for Dimethyl dicarbonate (12 total), please visit the HSDB record page.

Dimethyl dicarbonate (CAS Reg. No. 4525-33-1) may be safely used in food in accordance with the following prescribed conditions: (a) The additive meets the following specifications: (1) The additive has a purity of not less than 99.8 percent ... (2) The additive contains not more than 2,000 ppm (0.2 percent) dimethyl carbonate. ... (b) The additive is used or intended for use as a microbial control agent in the following beverages under normal circumstances of bottling, canning, or other forms of final packaging, where the viable microbial load has been reduced to 500 microorganisms per milliliter or less by current good manufacturing practices such as heat treatment, filtration, or other technologies prior to the use of dimethyl dicarbonate: (1) In wine, dealcoholized wine, and low alcohol wine in an amount not to exceed 200 parts per million. (2) In ready-to-drink teas in an amount not to exceed 250 parts per million. (3) In carbonated or noncarbonated, nonjuice-containing (less than or equal to 1 percent juice), flavored or unflavored beverages containing added electrolytes (5-20 milliequivalents/liter sodium ion (Na+) and 3-7 milliequivalents/liter potassium ion (K+)) in an amount not to exceed 250 parts per million. (4) In carbonated, dilute beverages containing juice, fruit flavor, or both, with juice content not to exceed 50 percent, in an amount not to exceed 250 parts per million.

Dimethyldicarbonate (DMDC), like diethyldicarbonate, has a broad antimicrobial activity when added to drinks. The inactivation of microorganisms proved to be strongly related to the inactivation of enzymes by protein modification, mainly through reaction with nucleophilic groups (imidazoles, amines, thiols).

Food additive; fungicide

Preservative

Potential preservative in unstandardized water-based non-alcoholic beverages (ready-to-drink teas, fruit-flavored sport drinks, energy drinks, and carbonated flavored soft drinks).

Dimethyldicarbonate (DMDC) is used as a cold sterilization agent for soft drinks and wines. It has a broad antimicrobial range of action against yeasts, mold fungi, and bacteria.

To help prevent fermentation in finished wines; to control spoilage yeast such as Brettanomyces; to decrease the amount of sulfur dioxide used in wines; to reduce warehouse holding time in early-to-market wines /Velcorin/

Food additives

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Dicarbonic acid, 1,3-dimethyl ester: ACTIVE

Dimethyldicarbonate (DMDC) is unstable in aqueous solution and breaks down almost immediately after addition to beverages. The principal breakdown products in wine and aqueous liquids are methanol and carbon dioxide. Dimethylcarbonate (DMC) and methyl ethyl carbonate (MEC), as well as carbomethoxy adducts of amines, sugars, and fruit acids, are also formed in minor amounts. In the presence of trace quantities of ammonia or ammonium ions (e.g. in wines), DMDC forms trace quantities of methylcarbamate (MC).

Preservative in wine, authorized in U.S. up to the cumulative amount of 200 ppm, in Australia up to 200 mg/kg, and in Europe up to 200 mg/L

Permitted addition to food with the following specifications: 1) purity of not less than 99.8%; 2) contains not more than 2000 ppm (0.2%) dimethyl carbonate; 3) in carbonated or noncarbonated, nonjuice containing, flavored ro unflavored beverages ... not to exceed 250 parts/trillion; 4) in cabonated, dilute beverages containing juice ... not to exceed 250 parts/trillion