| Chemical Properties | Ethyl chloroacetate is a colourless liquid with a pungent, fruity odor.Ethyl chloroacetate has a vapor pressure of 10mmHg at 38 °C (Lewis, 1997). It is insoluble in water, but miscible with alcohol, ether, and acetone (Lide, 1998); it is soluble in benzene (Lewis, 1997). Ethyl chloroacetate readily decomposes in hot water and alkalis (Lewis, 1997). |
| Uses | Ethyl chloroacetate is a reagent used in the preparation of 5 member heterocycles. It is used as pharmaceutical and organic intermediate. It is used as a solvent for organic synthesis and the production of pesticides (such as sodium fluoroacetate). |
| Preparation | Ethyl chloroacetate is synthesized by esterification of chloroacetic acid and ethanol under the catalysis of sulfuric acid. The reaction equation is as follows:
ClCH2COOH+C2H5OH[H2SO4]→ClCH2COOC2H5+H2O
Reaction: Add chloroacetic acid, ethanol and benzene into the esterification pot, turn on the stirrer, slowly add sulfuric acid, heat to reflux, continuously steam out the benzene-water azeotrope, and de-esterify the water generated by condensation and separator layering, Benzene is refluxed into the esterification pot, cooled and discharged when there is no more water to steam out, the crude ester is washed with saturated sodium bicarbonate solution and water to neutrality, dried with anhydrous calcium chloride, distilled, and collected The fraction at 144-146°C is the finished product of ethyl chloroacetate, the content is ≥99.0%, and the yield is 85%. |
| Synthesis Reference(s) | Tetrahedron, 23, p. 359, 1967 DOI: 10.1016/S0040-4020(01)83321-4 |
| General Description | A clear colorless liquid with a pungent odor. Flash point 100°F. Denser than water and insoluble in water. Vapors heavier than air. |
| Air & Water Reactions | Highly flammable. Slow hydrolysis to acidic products will cause slow corrosion of common metals. No hazard involved. [USCG, 1999]. |
| Reactivity Profile | Ethyl chloroacetate is a chlorinated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. |
| Hazard | Strong irritant to eyes. |
| Health Hazard | Inhalation causes irritation of mucous membrane, headache, and nausea. Contact with liquid causes extreme eye irritation and conjunctivitis; irritates skin if not removed at once. Ingestion causes irritation of mouth and stomach. |
| Fire Hazard | Special Hazards of Combustion Products: Irritating, toxic hydrogen chloride and phosgene may be generated in fires. |
| Chemical Reactivity | Reactivity with Water Very slow, not hazardous; Reactivity with Common Materials: Slow hydrolysis to acidic products; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. |
| Safety Profile | oison by skin contact and subcutaneous routes. A severe eye irritant. Questionable carcinogen with experimental neoplastigenic data.Flammable liquid; a dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Will react with water or steam to produce toxic and corrosive fumes. Vigorous reaction with sodium cyanide. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of cl-. |
| Potential Exposure | Used to make rodenticides, dyes, and other chemicals. Also used as a military poison |
| Shipping | UN1181 Ethylchloroacetate, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid. |
| Purification Methods | Shake the ester with satutated aqueous Na2CO3 (three times), aqueous 50% CaCl2 (three times) and saturated aqueous NaCl (twice). Dry it with Na2SO4 or MgSO4 and distil it. [Beilstein 2 IV 481.] LACHRYMATORY. |
| Incompatibilities | May form explosive mixture with air. Incompatible with strong bases; strong acids; reducing agents. Moisture, water, and steam contact forms toxic and corrosive fumes. Violent reaction with oxidizers, alkaline earth metals (barium, calcium, magnesium, strontium, etc.), alkaline metals, sodium cyanide. Attacks metals in the presence of moisture. |
| Waste Disposal | Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. |
