Chloroacetic anhydride

H301+H311+H331 (67.5%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (71.4%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H317 (24.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H318 (68.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H331 (71.4%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H400 (71.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (67.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 154 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Colorless to slightly yellow solid with a pungent odor; [HSDB] White or off-white crystalline powder; [MSDSonline]

PRISMS FROM BENZENE

Colorless to slightly yellow crystals

Pungent odor

203 °C @ 760 mm Hg

Freely sol in ether, chloroform; slightly sol in benzene; practically insol in cold petroleum ether

1.5494 @ 20 °C/4 °C

0.03 [mmHg]

3.72X10-2 mm Hg @ 25 °C

Hydrolyzes with water to chloroacetic acid

Boiling point

Crystal structure

Formula unit

Formula weight

Heat of sublimation

Nuclear quadrupole resonance spectroscopy

Quadrupole coupling

Space group

Unit cell

Unit cell parameter

Vapor pressure

Other Classes -> Acid Anhydrides, Other

Dermatotoxin - Skin burns.

Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

IRRITATING TO SKIN & EYES, MODERATELY TOXIC BY INHALATION.

Chloroacetic anhydride (CAS# 541-88-8) was evaluated for acute dermal toxicity in six guinea pigs at a dose range of 0.1 to 1.0 g/kg. The test substance was applied as a solid moistened with water on the cuff. Toxic signs with 24-hours included moderate edema and an entire patch area necrotic with hemorrhagic ban at periphery. After 1-week there was a depressed eschar over the entire patch area with moderate erythema at periphery. After 2-weeks, a secondary eschar appeared on one rabbit and another rabbit had one depressed, and a third had scarring. Time of death was between 4 and 24 hours. The test substance was determined to be a severe skin irritant with evidence of percutaneous absorption. The LD50 was determined to be between 0/1 and 0/2 g/kg.

Chloroacetic anhydride's production and use as an intermediate for cellulose chloroacetate may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 3.72X10-2 mm Hg at 25 °C indicates chloroacetic anhydride will exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetic anhydride 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 73 days. If released to soil, chloroacetic anhydride will rapidly react with water; an estimated base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively. Chloroacetic anhydride is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, chloroacetic anhydride will react rapidly with water and will not adsorb to suspended solids or sediment, volatilize or bioconcentrate. Occupational exposure to chloroacetic anhydride may occur through inhalation and dermal contact with this compound at workplaces where chloroacetic anhydride is produced or used. (SRC)

Chloroacetic anhydride's production and use in N-acetylation of amino acids in alkaline solution(1) and its use as an intermediate for cellulose chloroacetate(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) estimated using a structure estimation method(2); corresponding to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(1). Therefore, chloroacetic anhydride will not adsorb to soil nor volatilize from moist soil due to this rapid reaction with water. Chloroacetic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.72X10-2 mm Hg(2).

AQUATIC FATE: A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(1). This hydrolysis rate indicates that chloroacetic anhydride will react rapidly with water and will not adsorb to suspended solids or sediment, volatilize, or bioconcentrate(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroacetic anhydride, which has a vapor pressure of 3.72X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetic anhydride 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 73 days(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of chloroacetic anhydride with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 73 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(2).

An estimated BCF of 3 was calculated for chloroacetic anhydride(SRC), using an estimated log Kow of -0.07(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. Bioconcentration is unlikely to occur due to an estimated base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) which corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for chloroacetic anhydride can be estimated to be 3(SRC). According to a classification scheme(2), this estimated Koc value suggests that chloroacetic anhydride is expected to have very high mobility. An estimated base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) which corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(3) will make it unlikely for chloroacetic anhydride to be mobile.

The Henry's Law constant for chloroacetic anhydride is estimated as 4.42X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chloroacetic anhydride could volatilize from water surfaces(2) if it did not hydrolyze. A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) which corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(4), makes chloroacetic anhydride very susceptible to hydrolysis. Chloroacetic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.72X10-2 mm Hg(3).

Occupational exposure to chloroacetic anhydride may occur through inhalation and dermal contact with this compound at workplaces where chloroacetic anhydride is produced or used. (SRC)

Chloroacetic anhydride's production and use as an intermediate for cellulose chloroacetate may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 3.72X10-2 mm Hg at 25 °C indicates chloroacetic anhydride will exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetic anhydride 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 73 days. If released to soil, chloroacetic anhydride will rapidly react with water; an estimated base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively. Chloroacetic anhydride is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, chloroacetic anhydride will react rapidly with water and will not adsorb to suspended solids or sediment, volatilize or bioconcentrate. Occupational exposure to chloroacetic anhydride may occur through inhalation and dermal contact with this compound at workplaces where chloroacetic anhydride is produced or used. (SRC)

Chloroacetic anhydride's production and use in N-acetylation of amino acids in alkaline solution(1) and its use as an intermediate for cellulose chloroacetate(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) estimated using a structure estimation method(2); corresponding to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(1). Therefore, chloroacetic anhydride will not adsorb to soil nor volatilize from moist soil due to this rapid reaction with water. Chloroacetic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.72X10-2 mm Hg(2).

AQUATIC FATE: A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(1). This hydrolysis rate indicates that chloroacetic anhydride will react rapidly with water and will not adsorb to suspended solids or sediment, volatilize, or bioconcentrate(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroacetic anhydride, which has a vapor pressure of 3.72X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetic anhydride 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 73 days(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of chloroacetic anhydride with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 73 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(2).

An estimated BCF of 3 was calculated for chloroacetic anhydride(SRC), using an estimated log Kow of -0.07(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. Bioconcentration is unlikely to occur due to an estimated base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) which corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for chloroacetic anhydride can be estimated to be 3(SRC). According to a classification scheme(2), this estimated Koc value suggests that chloroacetic anhydride is expected to have very high mobility. An estimated base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) which corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(3) will make it unlikely for chloroacetic anhydride to be mobile.

The Henry's Law constant for chloroacetic anhydride is estimated as 4.42X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chloroacetic anhydride could volatilize from water surfaces(2) if it did not hydrolyze. A base-catalyzed second-order hydrolysis rate constant of 1.9X10+5 L/mole-sec(SRC) which corresponds to half-lives of 37 and 4 seconds at pH values of 7 and 8, respectively(4), makes chloroacetic anhydride very susceptible to hydrolysis. Chloroacetic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.72X10-2 mm Hg(3).

Occupational exposure to chloroacetic anhydride may occur through inhalation and dermal contact with this compound at workplaces where chloroacetic anhydride is produced or used. (SRC)

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.