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Epichlorohydrin(CAS No. 106-89-8)

Epichlorohydrin C3H5ClO (cas 106-89-8) Molecular Structure

106-89-8 Structure

Identification and Related Records

【CAS Registry number】
2,3-epoxypropyl chloride
3-Chloro-1,2-propylene oxide
3-Chloropropylene Oxide
3-Chloropropyl epoxide
Allyl chloride oxide
Cardolite NC-513
(Chloromethyl) Ethylene Oxide
Epoxypropyl chloride
Glycerol Epichlorohydrin
Glycidyl chloride
gamma-Chloropropylene oxide
【Molecular Formula】
C3H5ClO (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

clear, colorless
【Melting Point】
【Boiling Point】
22mmHg at 25°C
【Refractive Index】
【Flash Point】
6 g/100 mL (10℃)
6 g/100 mL (10 oC) in water
Colorless liquid
Stability Unstable. Flammable - note wide explosion limits and low flash point. Vapours may flow along surfaces to source of ignition. Contact with strong oxidisers may lead to fire. Incompatible with strong acids, strong bases, strong oxidizing agents, metal salts, amines, aluminium, chlorine and a variety of chlorine compounds, most com
【Storage temp】
Refrigerator (+4°C) + Flammables area
【Spectral properties】
Index of refraction: 1.44195 at 11.6 deg C/D; 1.43969 at 16 deg C/D; 1.43585 at 25 deg C/D
IR: 946 (Coblentz Society Spectral Collection)
NMR: 16 (Sadtler Research Laboratories Spectral Collection)
MASS: 185 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
IR: 2:124F (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
RAMAN: 289 (Sadtler Research Laboratories Spectral Collection)
【Computed Properties】
Molecular Weight:92.5242 [g/mol]
Molecular Formula:C3H5ClO
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:1
Exact Mass:92.002892
MonoIsotopic Mass:92.002892
Topological Polar Surface Area:12.5
Heavy Atom Count:5
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Effective Rotor Count:1.6
Conformer Sampling RMSD:0.4
CID Conformer Count:6

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Moderately toxic by inhalation. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by inhalation: respiratory, nose, and eyes. Human mutation data reported. A skin and eye irritant. A sensitizer. Flammable liquid when exposed to heat or flame. Explosive reaction with aniline. Reaction with trichloroethylene forms the explosive dichloroacetylene. Ignition on contact with potassium tert-butoxide. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids, caustic alkalies, aluminum, aluminum chloride, iron(III) chloride, or zinc. When heated to decomposition it emits toxic fumes of Cl?.
Hazard Codes?: T?Toxic
Risk Statements? :45-10-23/24/25-34-43?
R45:May cause cancer.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R43:May cause sensitization by skin contact.
Safety Statements? :53-45?
S53:Avoid exposure - obtain special instructions before use.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR:? UN 2023 6.1/PG 2
WGK Germany:? 3

【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
Marked nose & eye irritation occur only ... /above/ 100 ppm.
Epichlorohydrin effect on the skin, eyes, and respiratory tract may be delayed for several hours. Epichlorohydrin causes dermatitis.
Inhalation of epichlorohydrin causes irritation of the eyes and throat. ...
【Cleanup Methods】
Remove all ignition sources. Ventilate area of spill or leak.
For small quantities, absorb on paper towels. Evaporate in a safe place (such as a fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn the paper in suitable location away from combustible materials.
... It should not be allowed to enter a confined space, such as a sewer, because of the possibility of an explosion. Sewers designed to preclude the formation of explosive concentrations of epichlorhydrin vapors are permitted.
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Eliminate all ignition sources. Approach release from upwind. Releases may require isolation or evacuation. Use appropriate foam to blanket release and suppress vapors. Use water spray to cool and disperse vapors, protect personnel, and dilute spills to form nonflammable mixtures. Do not use clay absorbents in cleanup. Control runoff and isolate discharged material for proper disposal.
/SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./Environmental Consideration: Land spill Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply "universal" gelling agent to immobilize spill. Apply appropriate foam to diminish vapor and fire hazard.
Environmental considerations: Water spill Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Environmental Considerations: Air spill Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors.
UN 2023
【Fire Fighting Procedures】
Avoid use of dry chemical if fire occurs in container with confined vent. Containers may explode in fire because of polymerization.
Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Fight fire from protected location or maximum possible distance. Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool.
If material on fire or involved in fire Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
Evacuation: If fire becomes uncontrollable or container is exposed to direct flame consider evacuation of one-third (1/3) mile radius.
【Fire Potential】
Flammable liquid when exposed to heat or flame.
Commercial specifications for a product sold by one USA manufacturer are a minimum of 98.0% wt purity and a max of 0.2% wt water.
【DOT Emergency Guidelines】
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will 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 131P: FLAMMABLE LIQUIDS-TOXIC/ 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 and poison 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 131P: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... 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 131P: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Evacuation: ... 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.
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Fire: CAUTION: All these products have a very low flash point. Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. 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. For massive fire use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Spill or Leak: Fully encapsulating, vapor protective clothing should be worn for spills and leaks with no fire. 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. Small spills: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces.
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. 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. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
【Reactivities and Incompatibilities】
Strong oxidizers, strong acids, certain salts, caustics, zinc, aluminum, water [Note: May polymerize in presence of strong acids and bases particularly when hot.].
Epichlorohydrin can violently react with compounds carrying an active hydrogen atom, including water.
Epichlorohydrin liberates heat in the presence of ... alkalis, and certain salts ...
Interaction /between epichlorohydrin and an N-substituted aniline/ is exothermic and mixt was normally maintained at 60 deg C by stirring and cooling. Malfunction caused temp incr to 70 deg C and cooling capacity was insufficient to regain control. Temp ... incr to 120 deg C, when explosive decomp occurred.
Mixing 2-aminoethanol and epichlorohydrin in a closed container caused the temperature and pressure to increase.
Mixing ethylene diamine and epichlorohydrin in a closed container caused the temperature and pressure to increase.
Mixing epichlorohydrin and ethyleneimine in a closed container caused the temperature and pressure to increase.
Mixing epichlorohydrin and 70% nitric acid in a closed container caused the temperature and pressure to increase.
Mixing epichlorohydrin and oleum in a closed container caused the temperature and pressure to increase.
Ignition occurs when potassium t-butoxide reacts with ... epichlorohydrin ...
Mixing epichlorohydrin and 96% sulfuric acid in a closed container caused the temperature and pressure to increase.
Ignition occurs on contact with potassium tert-butoxide. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids, caustic alkalies, aluminum, aluminum chloride, iron(III) chloride, or zinc.
Contact with strong acids and bases, zinc, aluminium, metal chlorides, alcohol-containing materials, isopropylamine, trichloroethylene, and oxidizing agents may cause fire and explosions.
【Other Preventative Measures】
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
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.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to disperse vapors and dilute standing pools of liquid.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet should be immediately removed due to its flammability hazard (i.e., for liquids with a flash point
If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.
Evacuation: If fire becomes uncontrollable or container is exposed to direct flame-consider evacuation of one-third (1/3) mile radius.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
Skin, eye, and respiratory contact must be avoided & protective clothing including PVC suits, plastic gloves, goggles or face shield, hat, & neoprene or PVC boots should be worn. Air concn should not exceed recommended limits of exposure. Where more exposure ... expected, positive pressure respirator ... worn.
Gloves made of butyl rubber, when exposed to epichlorhydrin, protected the hands better than surgical rubber, polyethylene, polyvinyl alcohol, saranex-lamenated tyvek, neoprene and others. [Stampfer JF et al; Am Ind Hyg Assoc J 45 (9): 642-54 (1984)] PubMed Abstract
PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Respirator Recommendations: At concentrations above the NIOSH REL, or where there in no REL, at any detectable concentration: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor and acid gas canister/Any appropriate escape-type, self-contained breathing apparatus.

?Epichlorohydrin , its CAS NO. is 106-89-8, the synonyms are 1-Chloro-2,3-epoxy propane ; 2-(Chloromethyl)oxirane ; 3-Chloro-1,2-epoxypropane .?

【Octanol/Water Partition Coefficient】
log Kow = 0.45

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 202.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 11 , 1976,p. 131.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

【Disposal Methods】
[40 CFR 240-280, 300-306, 702-799 (7/1/2008)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U014, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Epichlorohydrin is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.
A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may the be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Epichlorohydrin is commercially prepared by high temperature chlorination of propylene to allyl chloride, followed by chlorohydration with hypochlorous acid to form isomeric glycerol dichlorohydrins. The mixture is subsequently dehydrochlorinated with alkali to yield epichlorohydrin.
Made by chlorohydrination of allyl chloride ... which is obtained by high-temperature chlorination of propylene. Byproducts of chlorination are cis- and trans-1,3-dichloropropene and 1,2-dichloropropane. Glycerol dichlorohydrins are made from allyl chloride, with 1,2,3-trichloropropane being obtained as a byproduct. Finally, epichlorohydrin is produced from the glycerol-dichlorohydrin mixture by treatment with base.
PRODUCT PROFILE: Epichlorohydrin: ECH /epichlorohydrin/ is essentially a derivative of propylene and chlorine that combines the reactivity of an epoxide group (an oxygen bridge) with the additional reactivity of a chloro-group on to a propylene backbone. There are two production routes to ECH: via allyl chloride or allyl alcohol. Over 90% of global capacity is based on allyl chloride which offers better economics if the site is fully integrated with incineration and co-product hydrochloric acid demand.
U.S. Exports

(1978) 9.90X10+9 G
(1983) 8.22X10+9 G
(1985) 3.21X10+10 g
U.S. Imports

(1978) 1.5X10+9 G
(1983) 1.5X10+9 G
(1985) 1.34X10+10 g
U.S. Production

(1977) 1.32X10+11 G
(1982) 1.52X10+11 G
(1984) 2.00X10+11 g
Oxirane, (chloromethyl)- 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 volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >500 million - 1 billion 1990 >500 million - 1 billion 1994 >500 million - 1 billion 1998 >1 billion 2002 >500 million - 1 billion
PRODUCT PROFILE: Epichlorohydrin: Major global epichlorohydrin capacity in 2003 (thousand tonnes/year) Major global epichlorohydrin capacity in 2003 (thousand tonnes/year) Country Capacity Europe - Czech Republic 13 - France 32 - Germany 157 - Netherlands 80 - Poland 35 - Russia 55 Americas - USA 480 Asia - China 80 - Japan 115 - South Korea 60 - Taiwan 80
Consumption Patterns

Epoxy resins, 65%; glycerine, 25%; epichlorohydrin elastomers, 5%; miscellaneous, 5% (1984)
Global demand is /estimated/ ... to have recovered to some 920,000-940,000 tonnes/year, following the serious dip in demand to around 840,000 tonnes in 2001 after years of steady growth. World capacity is estimated at 1.24 million tonnes/year with an occupancy of about 75%, although real utilization, discounting idled capacity and scheduled downtime, may be nearer 87%. ... West European demand is hovering around 250,000 tonnes/year. Japanese demand is fairly stagnant at 95,000-100,000 tonnes/year.
【Sampling Procedures】
Analyte: Epichlorohydrin. Sampler: Solid adsorbent trapping. Matrix: Air. Sample flow: 0.01 to 0.2 l/min by personal sampling pump. Sample size: 21 (at 2 ppm) to 30 liters.
NIOSH Method 1010. Analyte: Epichlorohydrin. Matrix: Air. Sampler: Solid sorbent tube (coconut shell charcoal, 100 mg/50 mg). Flow Rate: 0.01 to 0.2 l/min or less. Sample Size: 20 liters. Shipment: routine. Sample Stability; at least 2 weeks at 25 deg C.

Biomedical Effects and Toxicity

【Pharmacological Action】
Epichlorohydrin is caustic as both a liquid and gas. Irritation of the eyes and skin, and skin sensitization has been observed. Exposure to epichlorohydrin has caused inflammation of the lungs, asthmatic bronchitis, and liver and kidney damage. In acute poisonings, death may be caused by respiratory paralysis.
【Biomedical Effects and Toxicity】
The upper respiratory tracts of male Fischer F344 rats were surgically isolated and connected to a specially designed flow system. The tracheal connection of the upper respiratory tract and the lower respiratory tract was interrupted. The upper respiratory tract was exposed to propylene-glycol- monomethyl ether, propylene glycol monomethyl ether acetate, epichlorohydrin, cmpd which include vapors while the rat spontaneously breathed from a stream of air. Intact rats were exposed nose only to the same compound and the percentages of vapor absorbed were determined for comparison purposes. Attempts were made to correlate the results with the water solubility of the compounds. The data were compared to predictions of two compartment mathematical models. More than 50 to 70% of the epichlorohydrin, vapors passing through the isolated upper respiratory tacts were absorbed. With the exception of styrene and methylene chloride, the percentage of vapors absorbed by the upper respiratory tract approximated that observed in the lower respiratory tract and nose only exposed animals. There was no correlation between absorption in the URT and water solubility. The mathematical models generally predicted the absorption of vapors by the lower respiratory tract and intact animals accurately. The models seriously underestimated absorption of epichlorohydrin, by the upper respiratory tract. /Results indicate/ that blood air partitioning can account for absorption of chemicals by the upper respiratory tract, but only if other metabolic and physiological parameters are considered.
The highest tissue concentrations in rodents were found in the nose after inhalation, and in the stomach after ingestion. In rats, regardless of the route of exposure, most absorbed epichlorohydrin is metabolized rapidly, part being excreted as carbon dioxide via the lungs and part as water-soluble compounds via the urine.
Eight hours after oral administration of epichlorohydrin to rats, less than 10% of the dose was recovered in the gastro- intestinal tract; peak tissue levels occurred approximately 2 hr after dosing in males and 4 hr in females. Almost all orally-ingested epichlorohydrin was absorbed from the gastrointestinal tract of rats. The plasma concentration of epichlorohydrin or its metabolites in rats was 36.1 mg/liter, 3 hr after oral administration of 100 mg/kg body weight and 18.3 mg/liter directly after inhalation at a level of 378 mg/cu m. ... After absorption by rats, epichlorohydrin was distributed widely throughout many tissues Concentrations of epichlorohydrin found in blood, 2-4 hr after oral ingestion, were subsequently exceeded by a factor of 2 or more in the stomach and intestines, the kidneys, the prostate and lacrimal glands, and the liver. Directly after inhalation, such levels occurred mainly in the epithelium of the nasal turbinates, the lacrimal glands, kidneys, liver, and large intestines.
The covalent binding of epichlorohydrin and its metabolites to macromolecules was investigated using tissue homogenates made of nasal epithelium, lungs, liver, kidneys, and testes obtained immediately post-mortem from humans and from rats. The study revealed that human tissue homogenates incubated with 14C-epichlorohydrin had binding levels that were usually statistically significantly less than those in rat tissues. In the same report, rats were nose-only exposed for 6 hours to 14C-epichlorohydrin vapor at 2 ppm. The levels of binding were generally higher in the nasal epithelium and kidneys as compared with lungs, liver, and testes. There was no significant difference between the 14C-epichlorohydrin or its metabolites in the various tissues immediately following exposure and 42 hours later. The investigators suggested that once epichlorohydrin is inhaled, it is rapidly degraded enzymatically or nonenzymatically to nonreactive species.
In one study, rats were exposed via inhalation at 1 or 100 ppm of 14C-epichlorohydrin for 6 hours. Approximately 90% of the estimated inhaled dose was excreted in the urine (50%) or exhaled as 14-CO2 (40%). In studies in which 14C-epichlorohydrin was administered orally, 40% to 50% of the total radioactivity administered was excreted in the urine, 25% to 40% was excreted as 14-CO2 in the exhaled air, and less than 4% of the radioactivity was recovered from the feces. In rats administered a single oral dose of 10 mg/kg 14C-epichlorohydrin, peak tissue levels of radioactivity were found after 2 to 4 hours mainly in the liver, kidneys, and pancreas. ...

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a log Kow of 0.45(2) and a regression-derived equation(3), indicates that epichlorohydrin is expected to have very high mobility in soil(SRC). Volatilization of epichlorohydrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), calculated from a vapor pressure of 16.4 mm Hg(4) and water solubility of 65,900 mg/L(5). The potential for volatilization of epichlorohydrin from dry soil surfaces may exist based upon the vapor pressure(4). Epichlorohydrin may undergo hydrolysis in moist soil surfaces based on a hydrolysis half-life of 8.2 days in distilled water(6). Epichlorohydrin achieved 3% of the theoretical BOD in a sewage sludge over a 5 day incubation period, but achieved 14% of the theoretical BOD following acclimation(7), suggesting that biodegradation in acclimated soils may be important(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a log Kow of 0.45(2) and a regression-derived equation(3), indicates that epichlorohydrin is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), calculated from its vapor pressure of 16.4 mm Hg(4) and water solubility of 65,900 mg/L(5). Using this estimated Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 19 hours and 12 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis half-life of epichlorohydrin is 8.2 days in distilled water and 5.3 days in simulated seawater(8). Epichlorohydrin achieved 3% of the theoretical BOD in a sewage sludge over a 5 day incubation period, but achieved 14% of the theoretical BOD following acclimation(9); thus biodegradation in acclimated water may be important(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), epichlorohydrin, which has a vapor pressure of 16.4 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase epichlorohydrin 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 36 days(SRC), calculated from its rate constant of 4.4X10-13 cu cm/molecule-sec at 25 deg C(3).

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