Carbonochloridic acid, 2-chloroethyl ester

142.969

142.97

210-982-4

4D32H07Z9I

3277

DTXSID2060832

Colorless liquid

2915900090

26.30000

1.51

Chloroethyl chloroformate is a liquid. (EPA, 1998)

1.3847 g/cm³ @ Temp: 20 °C

<25 °C

155 °C

59.8±15.2 °C

1.439

Sol in alcohol, ether, acetone, benzene

Refrigerator

0.23 psi ( 20 °C)

Decomp in alkaline soln and hot water|Chloroformates are reactive intermediates that combine acid chloride, and ester functions. They undergo many reactions of acid chlorides, however, the rates are usually slower. Reactions of chloroformates, like other acid chlorides, proceed faster with better yields when alkali hydroxides or tertiary amines are present to react with the HCl as it forms. /Chloroformates/|Hydrolyze in water /chloroformates/|Conversion factor: 5.84 mg/cu m = 1 ppm|Flash point: 158 °F (70 °C)

Decomposed slowly by water forming ethanol, HCl, and CO2; on contact with moist air, it gives off HCl fumes; attacks many metals especially in humid atmosphere. REF [Handling Chemicals Safely, 1980. p. 476].

Halogenated Organic Compounds

Water-Reactive

CHLOROETHYL CHLOROFORMATE is an acid halide. Acid halides are water reactive; some are violently reactive. They are incompatible with strong oxidizing agents, alcohols, amines, alkali. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

II

6.1(a)

3277

3

R23;R34

S26-S36/37/39-S45

LQ5950000

T:Toxic;

P261-P280-P305 + P351 + P338-P310

H314-H331

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.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)

|Danger|H314 (91.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P321, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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)

(Non-Specific -- Ethyl Chloroformate) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire. Shut off ignition sources; no flares, smoking or flames in hazard area. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

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 protectionequipment should be worn even when contact lenses are in place.

Very irritating to eyes and skin.

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Chloroethyl chloroformate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.

Chloroethyl chloroformate's use as a chemical intermediate in the synthesis of other chemicals(1) could release the compound to the environment through various waste streams generated at sites of production and use(SRC).

TERRESTRIAL FATE: Chloroformates hydrolyze readily in water(1); therefore, aqueous hydrolysis will be the dominant fate process in moist soils(SRC). The low-boiling chloroformic esters, such as chloroethyl chloroformate, are highly volatile(2); therefore, evaporation from dry surfaces to the atmosphere will occur(SRC). Results of a single biodegradation study (using the Japanese MITI protocol) have classified ethyl chloroformate (a compound similar in structure to chloroethyl chloroformate) as biodegradable(3) but ethyl chloroformate hydrolyzes so fast the the biodegradation rates are probably for the hydrolysis products.|AQUATIC FATE: Chloroformates hydrolyze readily in water(1); ethyl chloroformate has an hydrolysis half-life of 31.5 min at 25 °C(1) and chloroethyl chloroformate is predicted to hydrolyze at a faster rate(2) forming the chloroethyl carbonate which can further hydrolyze to 2-chloroethanol and formic acid; therefore, aqueous hydrolysis will be the dominant fate process in the aquatic environment(SRC). Aqueous volatilization, bioconcentration, biodegradation, and adsorption to sediment are not expected to be important fate processes due to rapid hydrolysis(SRC).|ATMOSPHERIC FATE: Based upon a vapor pressure of 13 mm Hg at 48-49 °C(1), chloroethyl chloroformate is expected to exist primarily in the vapor-phase in the ambient atmosphere(2,SRC). It will degrade in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 14 days(3,SRC). Since chloroformates hydrolyzes readily in water(4), atmospheric degradation may occur through dissolution into clouds or through contact with rain or other atmospheric water(SRC).

The rate constant for the vapor-phase reaction of chloroethyl chloroformate with photochemically produced hydroxyl radicals has been estimated to be 1.13X10-12 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 14 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Chloroformates hydrolyze readily in pure water(2); although the hydrolysis rate specific to chloroethyl chloroformate was not found, the rate constant for the aqueous hydrolysis of ethyl chloroformate in water at 25 °C has been experimentally determined to be 3.67X10-4/sec which corresponds to a half life of 31.5 min(2); an hydrolysis rate estimation program(3) predicts that chloroethyl chloroformate will hydrolyze as much as three times faster than ethyl chloroformate(SRC).

Chloroformates hydrolyze readily in water(1); therefore, bioconcentration in aquatic organisms will not be an important process(SRC).

Using a structure estimation method based on molecular connectivity indexes, the Koc for chloroethyl chloroformate can be estimated to be approximately 15(1,SRC). According to a suggested classification scheme(2), this estimated Koc value suggests that chloroethyl chloroformate has high mobility in soil(SRC). However, chloroformates hydrolyzes readily in water(3); therefore, leaching in soil is not expected to be an important fate process(SRC).

The Henry's Law Constant for chloroethyl chloroformate can be estimated to be 1.1X10-3 atm-cu m/mole using a structure estimation method(1,SRC); this value of Henry's Law Constant indicates that volatilization from water is potentially an important fate process(2). However, chloroformates hydrolyze readily in water(3); therefore, volatilization from water is not expected to be important(SRC). The low- boiling chloroformic esters, such as chloroethyl chloroformate, are highly volatile(4); therefore, evaporation from dry surfaces will occur(SRC).

Chloroethyl chloroformate was tentatively identified in water sample collected from the Philadelphia, PA Torresdale water treatment plant in Mar 1975(1).

... by ingestion and inhalation.|The low-boiling chloroformic esters (such as chloroethyl chloroformate) are highly volatile(1); therefore, occupational exposure can occur through inhalation(SRC).

Carbon dioxide, hydrogen chloride, phosgene, and alkyl chlorides; main impurities are corresponding carbonates /chloroformic esters/

(Non-Specific -- Ethyl Chloroformate) Poisonous; may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. (EPA, 1998)

Warning: Respiratory effects may be delayed up to 72 hrs after exposure. Caution is advised. Signs and Symptoms of Chloroethyl Chloroformate Exposure: Signs and symptoms of acute exposure to chloroethyl chloroformate may include irritation and burns of the eyes and skin. Irritation of esophagus or gastrointestinal tract may also occur. Acute inhalation exposure to chloroethyl chloroformate may result in respiratory tract irritation, which can progress to pulmonary edema up to 72 hours after exposure. Emergency Life-Support Procedures: Acute exposure to chloroethyl chloroformate may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to chloroethyl chloroformate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support, with close arterial blood gas monitoring, if possible. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to chloroethyl chloroformate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. DO NOT induce vomiting. 4. Give the victims water or milk: children up to 1 year old, 125 mL (4 oz or 1/2 cup); children 1 to 12 years old, 200 mL (6 oz or 3/4 cup); adults, 250 mL (8 oz or 1 cup). Water or milk should be given only if victims are conscious and alert. 5. Activated charcoal may be administered if victims are conscious and alert. Use 30 to 100 g in adults and 15 to 30 g in children (1 to 2 g/kg in infants). 6. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Use 30 to 100 g in adults and 15 to 30 g in children. 7. Transport to a health care facility. (EPA, 1998)

Typical specifications of commercial chloroformates: purity, 98%; phosgene, <0.1%, iron, <10 ppm; acidity as HCl, <0.1%; alcohol or phenol, <2% /chloroformic esters/|Commercial products have concentrations of 97-99 wt% /chloroformic esters/|97%

Carbonochloridic acid, 2-chloroethyl ester: ACTIVE|Most chloroformate production is used captively and production figures are not available /chloroformic esters/|Can be prepared by reacting phosgene with ethylene oxide

The quantitative analysis of chloroformic esters can be carried out by titration, gas chromatography, high-performance liquid chromatography (HPLC) /chloroformic esters/