Aziridine

Hazardous Air Pollutants (HAPs)

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Carcinogens

Pungent, ammonia-like odor

Amine odor

0.8321 at 68 °F (EPA, 1998) - Less dense than water; will float

0.8321 at 24 °C/4 °C

Relative density (water = 1): 0.8

0.83

0.832 @25 °C

0.83

Oily, water-white liquid

Colorless liquid ... [Note: Usually contains inhibitors to prevent polymerization].

Miscible (NIOSH, 2024)

SOL IN ALKALI

Soluble in ethanol; slightly soluble in ether; very soluble in chloroform; miscible in organic solvents

In water, 1X10+6 mg/L (miscible)

Solubility in water: miscible

Miscible

12 °F (EPA, 1998)

The Guide from the Emergency Response Guidebook is for "ethylenimine, inhibited." -11 °C

12 °F (-11 °C) (Closed cup)

-11 °C c.c.

12 °F

12 °F

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Chemical: Aziridine

Hazard Traits - Carcinogenicity; Genotoxicity; Hematotoxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Ocular Toxicity; Respiratory Toxicity

Status: Active Update: 26-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14422

Ethylenimine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Irritating vapors are generated when heated. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. May polymerize in fires with evolution of heat and container rupture. Runoff to sewer may create fire or explosion hazard. Ethyleneimine vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents. Toxic oxides of nitrogen are produced during combustion. Upon treatment with sodium hypochlorite, it gives off the explosive compound 1-chloroazidine. Avoid acids, sodium hypochlorite. If heated under pressure, instability may result. Hazardous polymerization may occur. Avoid contact with silver or aluminum. Explosive polymerization may occur upon contact with acids. Polymerization is catalyzed by carbon dioxide. (EPA, 1998)

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

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with acids or oxidizing agents.

Ethyleneimine is classified as extremely toxic with a probable oral lethal dose of 5-50 mg/kg which is approximately 7 drops to 1 teaspoonful for a 70 kg (150 lb.) person. Ethyleneimine gives inadequate warning when over-exposure is by inhalation or skin absorption. It is a severe blistering agent, causing third degree chemical burns of the skin. Also, it has a corrosive effect on mucous membranes and may cause scarring of the esophagus. It is corrosive to eye tissue and may cause permanent corneal opacity and conjunctival scarring. Severe exposure may result in overwhelming pulmonary edema. Renal damage has been described. Hemorrhagic congestion of all internal organs has been observed. (EPA, 1998)

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

Ethyleneimine has many uses, including in polymerization products and in adhesives and binders. Acute (short-term) inhalation exposure to ethyleneimine causes severe respiratory tract irritation and inflammation in humans, but symptoms may be delayed for several hours. Some symptoms of acute inhalation exposure in humans include tearing and burning of the eyes, sore throat, nasal secretion, bronchitis, shortness of breath, and edema of the lungs. Ethyleneimine is a severe blistering agent, causing third degree chemical burns of the skin. It is also corrosive to eye tissue and may cause permanent corneal opacity and conjunctival scarring. At low levels, chronic (long-term) inhalation exposure has been reported to result in effects on the blood in humans. EPA has not classified ethyleneimine for carcinogenicity.

Liquid causes first degree burns on short exposure and second degree burns on long exposure; [CHRIS] Skin sensitization, mucous membrane irritation, liver and kidney injury, and toxic pneumonitis have been seen after occupational exposure; [ACGIH] A lachrymator; [HSDB] Germ cell mutagens that have shown to increase the mutant frequency in the progeny of exposed mammals. [MAK] Ethyleneimine, stabilized (UN1185) has warning of explosive polymerization; [ERG 2016]

1185 131P

1185 131P(inhibited)

P054; As stipulated in 40 CFR 261.33, when ethyleneimine, 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 container or inner liner used to hold this waste or 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(e)).

Do not extinguish fire unless flow can be stopped; use water in flooding quantities as a fog. Solid streams of water may be ineffective. Apply water from as far a distance as possible.

Use water in large amounts, alcohol-resistant foam, powder. NO carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

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

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer 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: Ethyleneimine exposure may result in delayed pulmonary edema within 24 to 48 hours. Also, acute effects such as nausea, eye irritation, etc., are often delayed for 30 minutes to 3 hours. Caution is advised.

General First Aid:

(General first aid procedures)

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

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Use dry chemical, "alcohol resistant" foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors & toxic decomp products. Explosive decomp may occur under fire conditions. Fight fire from protected location or maximum possible distance.

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. /Ethyleneimine, stabilized/

Use dry-chemical, foam, and carbon dioxide extinguishers. Water spray, though ineffective to extinguish, may help to keep fire-exposed containers cool. Fight fires from safe distances.

Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one (1) mile radius. /Ethyleneimine, stabilized/

Can be stored for some time over a few pellets of sodium hydroxide. /In a closed container/

Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, & sunlight. Separate from oxidizing materials & peroxides.

/Aziridine/ normally stored over solid caustic alkali, to minimize polymerization catalysed by presence of carbon dioxide.

Cover with a 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton.

Spill or Leak Procedures: Releases may require isolation or evacuation. Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use water spray to cool and disperse vapors, protect personnel, and dilute spill to form nonflammable mixtures. Absorb in noncombustible material for proper disposal.

[40 CFR 240-280, 300-306, 702-799 (7/1/2005)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P054, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P054, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Good candidate for liquid injection with a temperature of 650-1,600 °C with residence times of 0.1-2 seconds. Good candidate for rotary kiln with a temperature of 820-1,600 °C with residence times for liquids and gases: seconds; solids: hours. Good candidate for fluidized bed with a temperature of 450-980 °C with residence times for liquids and gases: seconds; solids: longer.

Incineration: 1) Dissolve in such combustible solvent as alcohols, benzene etc. Spray the soln into the furnace with afterburner and scrubber. 2) Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in the furnace.

Frequency of somatic point mutation induced by ethylenimine in Drosophila melanogaster larvae (heterozygous females and hemizygous males) was reduced after caffeine treatments, but it increased the frequency of chromosome aberrations and mitotic recombinations that were induced.

Barley (Hordeum vulgare) seeds were treated with ethylenimine and diethyl sulfate separate and in combination. Combination of the two was simultaneous (EI + diethyl sulfate) or sequential (EI followed by diethyl sulfate or diethyl sulfate followed by EI). Frequency of chromosome aberrations and chlorophyll mutation induced by EI was significantly higher than that induced by diethyl sulfate. Highest frequency of mutation was obtained with EI followed by diethyl sulfate, next (in descending order) was EI + diethyl sulfate, EI alone, diethyl sulfate followed by EI, and diethyl sulfate alone. Interaction of these agents with genetic material is complex and specific, depending on sequence in which the mutagens are applied.

Sodium selenite significantly decreased frequency of chromosome aberrations induced in wheat by ethyleneimine. Optimum concentration of sodium selenite ranged from 0.01 to 0.1 ug/mL. At these concentrations it displayed high antimutagenic activity without affecting cell division.

When barley seeds were treated wiith ethylenimine and cysteine, mutations induced by ethylenimine were markedly suppressed by cysteine.

LC50 Leuciscus idus melanotus (Carp) 2.4 mg/L/48 hr /formulated product/ /Conditions of bioassay not specified in source examined/

LC50 Daphnia magna (Water flea) 14 mg/L/24 hr; static /formulated products/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from an assigned water solubility of 1X10+6 mg/L (miscible)(2) and a regression-derived equation(3), indicates that ethyleneimine is expected to have very high mobility in soil(SRC). However, the pKa of ethyleneimine is 8.04(4), indicating that this compound will partially exist as a cation in the environment and cations generally do adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of ethyleneimine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 213 mm Hg(6), and assigned value for water solubility(2). Ethyleneimine is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). Biodegradation data were not available(SRC, 2006).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from an assigned water solubility of 1X10+6 mg/L (miscible)(2) and a regression-derived equation(3), indicates that ethyleneimine is not expected to adsorb to suspended solids and sediment(SRC). However volatilization will be attenuated as ethyleneimine exits as a cation (pKa = 8.04(4)) under environmental conditions and will therefore absorb to solids and sediment. Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 213 mm Hg(5), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 17 days, respectively(SRC). Attenuation is pH dependent with little volatilization expected under acidic conditions(6). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyleneimine, which has a vapor pressure of 213 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyleneimine 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 2.6 days(SRC), calculated from its rate constant of 6.10X10-12 cu cm/molecule-sec at 25 °C(3). Ethyleneimine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

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

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

Cough. Dizziness. Headache. Laboured breathing. Nausea. Vomiting. Symptoms may be delayed.

MAY BE ABSORBED! Redness. Skin burns. Blisters.

Redness. Pain. Severe deep burns.

Abdominal pain. Burning sensation. Vomiting. Shock or collapse. Further see Inhalation.

irritation eyes, skin, nose, throat; nausea, vomiting; headache, dizziness; pulmonary edema; liver, kidney damage; eye burns; skin sensitization; [potential occupational carcinogen]

Examinations for leukocyte counts, erythrocytes, and thrombocytes and check for kidney disorders.

Examinations should include a history of exposure to other carcinogens, smoking, alcohol, medications, and family history. The skin, eye, lung, and liver should be evaluated. Sputum or urine cytology should be helpful.

The Koc of ethyleneimine is estimated as 2(SRC), using an assigned value for water solubility of 1X10+6 mg/L (miscible)(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethyleneimine is expected to have very high mobility in soil. However, the pKa of ethyleneimine is 8.04(4), indicating that this compound will partially exist as a cation the environment and cations generally do adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Ethyleneimine readily complexes with metal salts(6) which may be present in soil(SRC).

P054; As stipulated in 40 CFR 261.33, when ethyleneimine, 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 container or inner liner used to hold this waste or 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(e)).

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. Ethyleneimine is included on this list.

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 1 lb or 0.454 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. Ethyleneimine is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Ethyleneimine

1

10000

Flammable chemical that can be released at a facility.

The ethylenimines are classic alkylating agents with biologic effects similar to the beta-chloroethylamines. /Ethylenimines/

Ethyleneimine reacted with guanosine in aqueous medium to yield two identified products: imidazole-ring-opened 7-alkylguanosine (80%) and intact 1-alkylguanosine (14%). Incubation of ethyleneimine with guanosine or deoxyguanosine at pH 6.0 (1 hr, 37 °C) yielded some intact 7-alkylated products. Half-life of imidazole ring opening of 7-alkylguanosine was 11, 5, and 2.8 min at pH 7.0, 7.7, and was 21 min at pH 7.7.

... Examples of direct-acting mutagens include alkylating agents such as ... ethyleneimine ... Direct-acting carcinogens are typically carcinogenic at multiple sites and in all species examined ...

When (14)C-ethyleneimine (0.30-0.42 mg/kg body weight) was injected ip into rats, approx one-half of the (14)C was excreted into the urine and 2-6% in feces after 96 hr. Only a small amount of urinary (14)C was ethyleneimine; the major portion of the urinary (14)C was found in a number of unidentified products. Three to 5% of the (14)C was expired as CO2, and 1-3% was expired as ethyleneimine.

Goups of 5-6 male Dow-Wistar rats were injected intraperitoneally with 0.3-0.42 mg/kg 14-C-aziridine (ethyleneimine) and were sacrificed after 24 and 96 hours. In both cases, ca. 50% of the administered dose was excreted in the urine; small amounts were present in the feces and expired air (3-5%). A small amount of the test substance itself was detected in urine, the major part of the radioactivity was due to unknown metabolites. Radioactivity was distributed throughout the rats, with a slight accumulation in liver, intestine, caecum, spleen, and kidneys.

... /It/ penetrates animal skin so rapidly that its percutaneous toxicity is not decreased if it is washed off 1 min after contact.

Ethyleneimine is used in polymerization products; as a monomer for polyethyleneimine; as a comonomer for polymers (e.g., with ethylenediamine); and in paper and textile chemicals, adhesives, binders, petroleum refining chemicals, fuels and lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion exchange resins, photographic chemicals, and surfactants.

Used to produce polyethyleneimine and other organic chemicals; [ACGIH] Used in the paper, textile, petroleum, lacquer, cosmetic, and photography industries; [HSDB]

Regulated as a carcinogen--See 29CFR1910.1003 (Code of Federal Regulations pertaining to the manufacturing, processing, repackaging, releasing, handling, and storing of this chemical);

Petroleum Production and Refining [Category: Industry]

Ethyleneimine is used to manufacture triethylene melamine and is used in its polymeric form in paper and textile chemicals, adhesive binders, petroleum refining chem, fuels & lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion exchange resins, photographic chemicals, colloid flocculants and surfactants.

Monomer for polyethyleneimine

This chemical is listed as a High Production Volume (HPV) (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).

(1977) AT LEAST 4.54X10+8 G

(1978) greater than 1.50X10+9 g

(1994) >1 million-10 million pounds

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

Prepared by treating 2-chloroethylamine hydrochloride with sodium hydroxide ... from beta-aminoethylsulfuric acid by reaction with sodium hydroxide ... .

Prepn: Ethanolamine is /esterified/ by sulfuric acid to ethanolamine-sulfuric acid ester, which is reacted with sodium hydroxide in a normal reaction to form ethyleneimine.

Reaction of ammonia with ethylene dichloride

Commercially, 2-aminoethyl hydrogen sulfate cyclizes at 120-140 °C under pressure to give ethyleneimine

Purity 99%

Caustic alkalis are added /to inhibit polymerization/.

Food Contaminant -> CONTAMINANT -> JECFA Functional Classes

Cosmetics -> Viscosity controlling