Epichlorohydrin

Hazardous Air Pollutants (HAPs)

Carcinogens

log Kow = 0.45

0.45

0.26

0.45

Odor is sweet, pungent or chloroform-like ... generally perceived as a slightly irritating chloroformlike odor

Pungent, garlic-like odor

1.18 to 1.801 at 68 °F (EPA, 1998)

1.1750 at 25 °C/4 °C

Relative density (water = 1): 1.2

1.18

1.175 @25 °C

1.18

50 to 100 mg/mL at 72 °F (NTP, 1992)

Miscible with most organic solvents

Miscible with alcohol, ether, chloroform, trichloroethylene, carbon tetrachloride; immiscible with petroleum hydrocarbons.

In water, 6.59X10+4 mg/L at 25 °C

65.9 mg/mL at 25 °C

Solubility in water, g/100ml at 20 °C: 6

93 °F (EPA, 1998)

88 °F

88 °F (31 °C) (Closed cup)

31 °C c.c.

93 °F

93 °F

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P321, P330, P333+P317, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1920) of reports.

Danger

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Oxirane, (chloromethyl)-

Hazard Traits - Carcinogenicity; Ocular Toxicity; Reproductive Toxicity; Respiratory Toxicity

Regulation (EC) No 178/2002 (amended)

Oxirane, 2-(chloromethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxirane, 2-(chloromethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 14-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15559

Oxirane, (chloromethyl)-: HSNO Approval: HSR000977 Approved with controls

When heated to decomposition, this compound evolves highly toxic fumes of phosgene and carbon monoxide. Reactive and incompatible with strong oxidizers, strong acids, caustics, zinc, aluminum, chlorides of iron and aluminumand compounds with an active hydrogen atom, including water. Unstable, avoid heat, contaminants, strong acids and bases, certain curing agents such as ethylenediamine. Hazardous polymerization may occur. (EPA, 1998)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 31 °C explosive vapour/air mixtures may be formed.

This compound 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. (EPA, 1998)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

Epichlorohydrin is mainly used in the production of epoxy resins. Acute (short-term) inhalation exposure to epichlorohydrin in the workplace has caused irritation to the eyes, respiratory tract, and skin of workers. At high levels of exposure, nausea, vomiting, cough, labored breathing, inflammation of the lung, pulmonary edema, and renal lesions may be observed in humans. Chronic (long-term) occupational exposure of humans to epichlorohydrin in air is associated with high levels of respiratory tract illness and hematological effects. Damage to the nasal passages, respiratory tract and kidneys have been observed in rodents exposed to epichlorohydrin by inhalation for acute or chronic duration. An increased incidence of tumors of the nasal cavity has been observed in rats exposed by inhalation. EPA has classified epichlorohydrin as a Group B2, probable human carcinogen.

Can cause severe skin burns and a skin sensitizer; Inhalation of vapor can cause lung edema and asthma-like reactions; [ICSC] In high-dose animal studies, epichlorohydrin causes testicular damage and sterility. [Frazier, p. 340] Animals exposed in subchronic inhalation studies at 50 ppm show kidney damage and liver effects. TLV Basis is respiratory tract irritant; [ACGIH] Suspected germ cell mutagen (3B); [MAK] Destructive to mucous membranes and upper respiratory tract; [Sigma-Aldrich MSDS] Epichlorohydrin (UN2023) has warning of explosive polymerization; [ERG 2016]

2023 131P

2023 131P

USEPA; Response To Public Comments On Draft Health Assessment Document for Epichlorohydrin (1983) EPA 600/8-83-032A Contract 68-02-4030

USEPA; Health Assessment Document: Epichlorohydrin (1983) EPA-600/8-83-032A

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Epichlorohydrin (106-89-8) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s082epic.pdf]

European Commission, ESIS; IUCLID Dataset, 1-Chloro-2,3-epoxypropane (106-89-8) (2000 CD-ROM edition).[Available from, as of March 4, 2009: http://esis.jrc.ec.europa.eu/]

If fire becomes uncontrollable, or containers are exposed to direct flames, evacuate for a radius of 1,500 feet. Isolate for one-half mile in all directions if tank car or truck is involved in fire.

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.

Wear protective gloves when administering first aid. First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Put clothes in sealable container. Refer immediately for medical attention.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Warning: Effects may be delayed for several hours. Caution is advised.

General First Aid:

(General first aid procedures)

· Wear positive pressure self-contained breathing apparatus (SCBA).

687.0 [ppm]

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.

Separate from acids, alkalies, salts, water, and oxidizers. Store in a cool, dry, well-ventilated location. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet.

/Store at/ ambient temperature

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Epichlorohydrin should be stored in tightly closed, labeled containers in fire-proof, cool, dry rooms. Apply ventilation across the floor. Epichlorohydrin attacks steel in the presence of moisture. The compound should be stored away from strong acids and bases, zinc, aluminium, metal chlorides, alcohol-containing material, isopropylamine, trichloroethylene, and oxidizing agents.

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/

For more Cleanup Methods (Complete) data for EPICHLOROHYDRIN (8 total), please visit the HSDB record page.

[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 °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 °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 °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/

For more Disposal Methods (Complete) data for EPICHLOROHYDRIN (8 total), please visit the HSDB record page.

Gastrointestinal

[in animals: nasal cancer]

Respiratory

Eyes, skin, respiratory system, kidneys, liver, reproductive system

Minimum inhibitory concentration; Species: Microcystis aeruginosa (Blue algae); Conditions: static, 27 °C, pH 7.0; Concentration: 6.0 mg/L for 8 days; Effect: cell multiplication /from table/

Minimum inhibitory concentration; Species: Scenedesmus quadricauda (Green algae); Conditions: static, 27 °C, pH 7.0; Concentration: 5.4 mg/L for 8 days; Effect: cell multiplication /from table/

Minimum inhibitory concentration; Species: Pseudomonas putida (Bacteria); Conditions: static, 25 °C, pH 7.0; Concentration: 55 mg/L for 16 hr; Effect: cell multiplication /from table/

Minimum inhibitory concentration; Species: Entosiphon sulcatum (Protozoa); Conditions: static, 25 °C, pH 6.9; Concentration: 35 mg/L for 72 hr; Effect: cell multiplication /from table/

For more Ecotoxicity Values (Complete) data for EPICHLOROHYDRIN (18 total), please visit the HSDB record page.

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 °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 °C(3).

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

IDENTIFICATION: Epichlorohydrin is a colorless liquid in which the vapor forms explosive mixtures in air. Phosgene, hydrogen chloride and carbon monoxide are liberated while burning. Acids, caustic solutions and halide salts initiate polymerization reactions. The compound is very reactive with metals such as zinc, aluminum, anhydrous metal halides, strong acids and bases along with alcohol containing materials. In the presence of moisture epichlorohydrin is corrosive to steel. Epichlorohydrin has a chloroform like odor. It is soluble in water. Epichlorohydrin is used for the manufacture of glycerine and unmodified epoxyresins. It is also used in the production of elastomers, glycidil ether, cross linked food starch, wet strength resins for the paper industry, water treatment resins, surfactants, ion exchange resins, plasticizers, dyestuffs, pharmaceutical products, emulsifiers, lubricants and adhesives. HUMAN EXPOSURE: On the basis of use patterns and the chemical and physical properties of epichlorohydrin, human exposure is mainly occupational, through vapor inhalation, direct skin contact and a slight exposure resulting from food consumption. Five human volunteers showed significant electroencephalogram changes in the voltage spikes of the alpha rhythm when they were exposed to a vapor of epichlorohydrin. Burning of the eyes and nasal mucosa was reported along with throat irritation. Seven cases of epichlorohydrin spills on the hands, thighs or feet have been described. In two cases epichlorohydrin was mixed with methanol. All spills resulted in protracted chemical burns with a latent period of between 10 minutes and several hours before the first symptoms appeared. Redness, swelling, edema, erosion and ulceration. One case was reported of a 39 year old man who inhaled a few deep breaths of epichlorohydrin vapor occured. Initially only a slight irritation of the eyes and throat was experienced with headache, nausea and vomiting; later chronic asthmatic bronchitis developed. Several biopsies over 2 yr period showed fatty degeneration together with functional disturbances of the liver. ANIMAL/FISH/PLANT/BACTERIAL/ PROTOZOAN/ STUDIES: When the tails of mice were immersed in undiluted epichlorohydrin for 15-60 minutes, most died exhibiting severe systemic poisoning. Within 7 days, 50% of the rabbits died after the application of epichlorohydrin on an occluded patch of shaved skin for 24 hr. Eight hours after oral administration of epichlorohydrin to rats less than 10% of the dose was recovered in the gastrointestinal tract; peak tissue levels occurred approximately 2 hr after dosing in the males and 4 hr in the females. Almost all orally ingested epichlorohydrin was absorbed from the gastrointestinal tract of rats. After absorption by rats, epichlorohydrin was distributed widely through out many tissues. Concentrations of epichlorohydrin found in the blood, 2-4 hr after oral ingestion were subsequently exceeded by a factor of 2 or more in the stomach and intestines, kidneys, prostate and lacrimal glands and the liver. Directly after inhalation, such levels occurred mainly in the epithelium of the nasal turbinates, lacrimal glands, kidneys, liver and large intestine. The following metabolites have been identified in the urine of rats: 2,3-dihydroxypropyl-S-cysteine and its mercapturic acid, beta-chloroacetic acid, oxalic acid and 1,3-bis-mercaptylpropanol-2-ol. Epichlorohydrin is an alkylating agent and has been found to react with nucleic acid bases deoxyguanosine and deoxyadenosine in vitro. After acute intoxication through oral, inhalation or skin exposure death was due to respiratory failure. At lethal doses, histopathological changes were found in the lungs, liver, kidneys, adrenals and thyroid gland of mice and rats. Acute respiratory irritation with hemorrhage and severe edema occurred in rats after inhalation or oral dosing. Rats injected once sc with epichlorohydrin showed nephrotoxic degeneration of the epithelium of the proximal tubules with ischemic cortex necrosis in the first days after exposure. This phase was accompanied by anuria or oliguria then death. Renal insufficiency was noted along with functional disturbances such as proteinuria, increased sodium ion concentration in the urine and an increased potassium ion concentration in the serum. The activity of the enzymes cytochrome c-oxidase, catalase, glutamic pyruvic transaminase and to a lesser extent alkaline phosphatase and glutamic oxaloacetic transaminase was inhibited in renal tissue, while catalase activity was increased in the urine. Regeneration of the kidneys in surviving rats started 5 days after exposure. Slight histological liver changes were also found in mice after 2 hr inhalation exposure to epichlorohydrin which included increased pentobarbital sleeping time in mice and a dose related decrease in histaminases activity in rats. Application of 80% solution epichlorohydrin in cottonseed oil caused corneal damage in the rabbit eye. A 20% solution induced definitive conjunctival and palpebral irritation with edema. Severe skin irritation was seen in a 24 hr occluded patch test on the shaved back of rabbits using a 5% solution of epichlorohydrin in cotton seed oil. Groups of 20 male Wistar rats received epichlorohydrin in water by stomach tube five times a week for 12 weeks. Reduced body weight was noted. From the first week onwards, time and dose related increase was observed in the changes in the basal cell layer of the forestomach such as thickening of the stomach wall, hemorrhaging, hyperplasia and increased number of mitotic figures and nuclei. After 12 weeks some of the rats had papillomas and squamous cell carcinomas. Each group of 30 female ICR/HCA Swiss mice received an ip dose of epichlorohydrin in tricaprylin once a week for up to 450 rats. A group of 100 mice did not receive any treatment and a group of 50 mice received the vehicle only. Papillary tumors were observed in the lungs of 11 exposed mice and 10 vehicle control mice. A group of 40 C3H mice was painted three times a week with a brushful of undiluted epichlorohydrin on the clipped midline of the back for up to 25 months. At month 17, 30 mice were alive and at moth 24 only 1 . No tumors were found. Female rats received orally epichlorohydrin in cotton seed oil between the 6th and 15th day of pregnancy. Higher dose levels were toxic to the dams, no embryotoxic, fetotoxic or teratogenic effects were observed. Similar negative results were obtained when female rats and rabbits inhaled vapors of epichlorohydrin 7 hr/day between the 6th and 15th or the 18th day of pregnancy. Epichlorohydrin is acutely toxic to blue and green algae, bacteria, crustacea and fish.

/AQUATIC SPECIES/ The 14 day LC50 value of epichlorohydrin to the guppy (Poecilia reticulata) was determined. These data were investigated through the construction of a quantitative structure-activity relationship (QSAR). Both hydrophobicity and alkylating potency of the compound were found to be necessary parameters for the satisfactory description of the LC50 data. The log LC50 experimental data for epichlorohydrin was 0.85 umol/L as compared to the calculated QSAR value of 1.08 umol/L.

Cough. Sore throat. Burning sensation. Headache. Laboured breathing. Nausea. Shortness of breath. Vomiting. Tremor. Symptoms may be delayed.

MAY BE ABSORBED! Redness. Pain. Burning sensation. Blisters. Serious skin burns.

Pain. Redness. Loss of vision. Severe deep burns.

Sore throat. Burns in mouth and throat. Headache. Nausea. Vomiting. Diarrhoea. Shock or collapse.

irritation eyes, skin with deep pain; nausea, vomiting; abdominal pain; resp distress, cough; cyanosis; reproductive effects; [potential occupational carcinogen]

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=106-89-8]

Detected, not quantified in chemical industry effluent in Louisville, KY(1). Epichlorohydrin was identified, not quantified, in emissions from polyurethane carpet cushions(2). Atmospheric emissions of epichlorohydrin were reported as 479,000 lbs/yr in the US in a 1983 study(3). Epichlorohydrin was identified, not quantified, in sewage samples obtained from a municipal treatment plant which was also supplied with the pre-treated sewage from a chemical plant(4).

U041; As stipulated in 40 CFR 261.33, when epichlorohydrin, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, (chloromethyl)- is included on this list. Effective date 10/4/82; Sunset date: 10/4/92.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Epichlorohydrin is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Epichlorohydrin is included on this list.

Epichlorohydrin is a substance for which a Federal Register notice has been published that included consideration of the serious health effects, including cancer, from ambient air exposure to the substance.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

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. Epichlorohydrin is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1000 lbs.

Epichlorohydrin is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

Epichlorohydrin

1

20000

Toxic chemical that can be released at a facility.

(FL) FLORIDA 3 ug/l

(AZ) ARIZONA 3.5 ug/l

(ME) MAINE 35 ug/l

The two reactive electrophilic sites, the C-1 carbon in the epoxide ring and C-3, the chlorine-bearing carbon, behave as alkylating agents and can react nonenzymatically with glutathione or protein sulfhydryl groups.

3-Chloroglycerophosphate inhibited rat sperm enzyme activities (glyceraldehyde-3-phosphate dehydrogenase and triosephosphate isomerase) and hence glycolysis. Only the S(-) isomer and not the R(+) isomer of 3-chloro-1,2-propanediol produced antifertility or antiglycolytic effects. Since epichlorohydrin has not been shown to have enzyme inhibitory effects, it may be that it is metabolized in vivo to S(-) alpha-chlorohydrin phosphate, to exert its antifertility effect.

No reports found; [TDR, p. 619]

... Male mice were given a single ip injection of epichlorohydrin dissolved in corn oil. Groups of ten mice were killed by decapitation at 1, 3, 5, 7, 10, 15, 20 and 30 minutes after injection and blood samples were collected. The in vivo half-life of epichlorohydrin is extremely short, being only just detectable after 15 minutes.

Half-life values of ECH and its metabolite, alpha-chloro-hydrin, in the blood of Swiss-Albino mice, which has been administered 200 mg/kg bw doses of the substances (oral or ip) were found to be 3.6-5.3 and 65 minutes.

... WISTAR RATS DOSED ORALLY OR IP WITH ... EPICHLOROHYDRIN YIELD ... URINARY METABOLITES ... 2,3-DIHYDROXYPROPYL-S-CYSTEINE & ITS N-ACETATE. SINCE EPICHLOROHYDRIN IS A STRONG ELECTROPHILE THAT IS CAPABLE OF REACTING WITH CELLULAR NUCLEOPHILES, IT IS PROBABLE THAT SOME EPICHLOROHYDRIN METABOLITES ARE ALSO COVALENTLY BOUND TO VARIOUS TISSUE MACROMOLECULES.

Rats given oral (14)C labeled epichlorhydrin and sacrificed after 3 days: 38% exhaled as carbon dioxide; 50% excreted as metabolites in urine; 3% excreted in the feces; and the remainder was found in the tissues - liver, kidney, and forestomach.

The major urinary metabolite of (14)C-epichlorohydrin, after oral administration to rats, was identified previously to be N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine at 36% of the administered dose. In a similar study reported here, 1,2-dibromo-3- chloropropane was metabolized to at least 20 radioactive urinary metabolites. N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine was only a minor metabolite (4%) of 1,2-dibromo-3-chloropropane. Epichlorohydrin was metabolized in vitro by rat liver microsomes to alpha-chlorohydrin, but 1,2-dibromo-3-chloroproane was not metabolized to epichlorohydrin or alpha-chlorohydrin under similar conditions. Covalent binding of radioactivity to liver microsomal proteins occurred for both substrates, but was less for (14)C-epichlorohydrin than for (14)C-1,2-dibromo-3-chloropropane. Addition of 3,3,3-trichloropropylene oxide, an inhibitor of epoxide hydrolase, increased the extent of protein binding of epichlorohydrin, but decreased the amojnt of (14)C-1,2-dibromo-3-chloropropane which was bound. The data indicate the epichlorohydrin is not a significant in vivo nor in vitro metabolite of 1,2-dibromo-3-chloropropane in the rat, and is unlikely to be responsible for the toxicity of 1,2-dibromo-3-chloropropane.

In in vitro studies, it was shown that epichlorohydrin was hydrolyzed into 3-chloro-1,2-propanediol by the microsomal epoxide hydrolase(s) (EC 3.3.2.3) of mouse liver in the absence of NADPH, the roles of protein or glutathione in this detoxification being insignificant.

For more Metabolism/Metabolites (Complete) data for EPICHLOROHYDRIN (7 total), please visit the HSDB record page.

WITH EXCEPTION OF PANCREAS, A CORRELATION OBSERVED BETWEEN TISSUE DISTRIBUTION & TARGET ORGAN TOXICITY. EXCRETION MAINLY IN URINE. 21 & 18% OF DOSE EXCRETED AS CO2 IN MALE & FEMALE RATS. PEAK TISSUE LEVELS IN FEMALES LOWER.

/EPICHLOROHYDRIN MAY BE/ ABSORBED THROUGH THE SKIN.

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.

For more Absorption, Distribution and Excretion (Complete) data for EPICHLOROHYDRIN (7 total), please visit the HSDB record page.

The primary use of epichlorohydrin is in the production of epoxy resins used in coatings, adhesives, and plastics. Epichlorohydrin is also used in the manufacture of synthetic glycerine, textiles, paper, inks and dyes, solvents, surfactants, and pharmaceuticals.

Used primarily in the manufacture of epoxy and phenoxy resins; [ACGIH]

Semiconductor Manufacturing [Category: Industry]

PRODUCT PROFILE: Epichlorohydrin: Epichlorohydrin (ECH) is mainly used in epoxy resins, which account for up to 75% of output. Synthetic glycerine is an ECH 'sink' allowing integrated players to use spare capacity to run synthetic glycerine plants independently of the natural glycerine market, and exit or substitute the natural product whenever epoxy demand requires. Glycerine can run to 10-15% of demand while other end uses, such as water and paper treatment resins, and elastomers, account for the remainder.

Insect fumigant /Former US/

Solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for celluloid

(1978) 9.90X10+9 G

(1983) 8.22X10+9 G

(1985) 3.21X10+10 g

(1978) 1.5X10+9 G

(1983) 1.5X10+9 G

(1985) 1.34X10+10 g

2023: 400,000,000 - <550,000,000 lb

(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).

For more U.S. Production (Complete) data for EPICHLOROHYDRIN (6 total), please visit the HSDB record page.

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.

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.

Cosmetics product ingredient: 1-Chloro-2,3-epoxypropane

Information on 2 consumer products that contain Epichlorohydrin in the following categories is provided:

Wholesale and Retail Trade

Oxirane, 2-(chloromethyl)-: ACTIVE

Diethylaminoethyl dextran gel can be used as a temporary wound covering to promote the wound healing process by funtioning as a substrate and providing a directional influence for cell propagation. The hydrogel sheet was prepared using epichlorhyrin as the crosslinking agent.