PRODUCTS

EPICHLOROHYDRINE

Epichlorohydrine (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrine is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

CAS NO.: 106-89-8
EC NO.: 203-439-8

Synonyms:
2-(Chloromethyl)oxirane; (Chloromethyl)oxirane; Epichlorohydrin; 1-Chloro-2,3-epoxypropane; γ-Chloropropylene oxide; Glycidyl chloride; ECH; Epiklorohidirin; Epiklorohidrine; epichlorohydrine; Epiklorohidrin; Epiklorohidrine; Epiclorohidrin; epichlorohydrin; Epichlorohydrin; Epiklorohidrine; Epichlorohidrine; Epichlorhydrin; epiklorohidrin; 1-Chloro-2,3-epoxypropane; 2-Chloromethyl oxirane; 2,3-Epoxypropyl chloride epichlorohydrine; chloromethyloxirane; γ-chloropropylene Epichlorohydrin; EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; 106-89-8; Epichlorhydrin; 1-Chloro-2,3-epoxypropane; Glycidyl chloride; Oxirane, (chloromethyl)-; Epichlorhydrine; Chloromethyloxirane; 1,2-Epoxy-3-chloropropane; 2,3-Epoxypropyl chloride; Chloropropylene oxide; 3-Chloro-1,2-epoxypropane; Glycerol epichlorhydrin; Epichloorhydrine; Glycerol epichlorohydrin; 3-Chloropropylene oxide; (CHLOROMETHYL)OXIRANE; Epicloridrina; 3-Chloro-1,2-propylene oxide; Epichlorohydryna; Epichlorophydrin; (Chloromethyl)ethylene oxide; alpha-Epichlorohydrin; epi-Chlorohydrin; 3-Chloropropene-1,2-oxide; SKEKhG; Oxirane, 2-(chloromethyl); (+/-)-Epichlorohydrin; Epoxypropyl chloride; gamma-Chloropropylene oxide; Propane, 1-chloro-2,3-epoxy-; 1-Chlor-2,3-epoxy-propan; 1-Cloro-2,3-epossipropano; 2-Chloromethyl-oxirane; 1-Chloor-2,3-epoxy-propaan; Rcra waste number U041; (+/-)-2-(Chloromethyl)oxirane; Allyl chloride oxide; DL-a-Epichlorohydrin; Epoxy-3-chloropropane; Caswell No. 424; (chloromethyl)-Oxirane; Chloropropylene;.alpha.-Epichlorohydrin; epichlorohydrine; Epicloridrina [Italian]; Epichloorhydrine [Dutch]; Epichlorhydrine [French]; Epichlorohydryna [Polish]; (RS)-3-chloro-1,2-epoxypropane; NSC 6747; Alyl chloride oxide; Chloropropyl epoxide;.gamma.-Chloropropylene oxide; CCRIS 277; HSDB 39; (DL)-.alpha.-Epichlorohydrin; 3-Chloropropyl epoxide; Epichlorohydrin, 99%; Oxirane,(chloromethyl)-; Chloro-1,2-epoxypropane; Chloro-2,3-epoxypropane; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; ECH; Chloropropene-1,2-oxide; 3-Chloro-propylene oxide; 2-(chloromethyl)-oxirane; EINECS 203-439-8; UN2023; 1-Chlor-2,3-epoxy-propan [German]; RCRA waste no. U041; 1-Chloor-2,3-epoxy-propaan [Dutch]; 1-Cloro-2,3-epossipropano [Italian]; Chloro-1,2-propylene oxide; oxirane, 2-(chloromethyl)-; (chloromethyl) Ethylene oxide; 1-chloro-2,3-epoxy-propane; 1-Chloro-2,3-epoxy propone; 56227-39-5; ECH; EPI; Polidexide; Oxirane, (chloromethyl)-, (R)-; Epichlorohydrin, 99%, AcroSeal(R); Polidexidi sulfas; 2596849; CAS-106-89-8; C3H5ClO; Sulfate de polidexide; Sulfato de polidexido; 5-17-01-00020 (Beilstein Handbook Reference); CCRIS 6387; epichiorohydrin; Polidexidi sulfas [INN-Latin]; epi-chlorohydrine; a-Epichlorohydrin; Epichloro hydrine; BRN 1420785; Sulfate de polidexide [INN-French]; Sulfato de polidexido [INN-Spanish]; (rs)-epichlorohydrin; (+) epichlorohydrin; (-) epichlorohydrin; 2-chloromethyloxirane; (?)-Epichlorohydrin; chloromethyl) Oxirane; (rac)-epichlorohydrin; Cardolite NC-513; racemic epichlorohydrin; beta-epoxypropylchloride; racemic epichlorohydrine; Epoxy-3-chlor opropane; 3-Chloropro pylene Oxide; 2-(chloromethyl) Oxirane; ech; (DL)-alpha-Epichlorohydrin; (RS)-(chloromethyl)oxirane; 3-chloro-1,2-epoxypropene; Epichlorohydrin Reagent Grade; (+/-)-1-Chloro-2,3-epoxypropane; Epichlorohydrin [UN2023] [Poison]; Epichlorohydrin [UN2023] [Poison]; (+/-)-Epichlorohydrin, analytical standard; DB-018066; Epichlorhydrin 1000 microg/mL in Methanol; LS-101030; E0012; Epichlorhydrin 100 microg/mL in Cyclohexane; (+/-)-Epichlorohydrin, purum, >=99% (GC); (+/-)-Epichlorohydrin, puriss., >=99.5% (GC); Starch, 2-(diethylamino)ethyl 2-((2-(diethylamino)ethyl)diethylammonio)ethyl ether, chloride, hydrochloride, polymer with (chloromethyl)oxirane

Epichlorohydrine

Production of Epichlorohydrine
Epichlorohydrine is traditionally manufactured from allyl chloride in two steps, beginning with the addition of hypochlorous acid, which affords a mixture of two isomeric alcohols:

In the second step, this mixture is treated with base to give the epoxide:

In this way, more than 800,000 tons (1997) of Epichlorohydrine are produced annually.

Glycerol routes of Epichlorohydrine
Epichlorohydrine was first described in 1848 by Marcellin Berthelot. The compound was isolated during studies on reactions between glycerol and gaseous hydrogen chloride.

Reminiscent of Berthelot's experiment, glycerol-to-Epichlorohydrine (GTE) plants have been commercialized. This technology capitalizes on the availability of cheap glycerol from biofuels processing. In the process developed by Dow Chemical, glycerol undergoes two substitution reactions when treated with hydrogen chloride in the presence of a carboxylic acid catalyst. This is the same intermediate formed in the allyl chloride/hypochlorous acid process, and is likewise then treated with base to form Epichlorohydrine.

Other routes
Routes that involve fewer chlorinated intermediates have continued to attract interest. One such process entails epoxidation of allyl chloride.

Properties of Epichlorohydrine
Chemical formula    C3H5ClO
Molar mass    92.52 g/mol
Appearance    colorless liquid
Odor    garlic or chloroform-like
Density    1.1812 g/cm3
Melting point    −25.6 °C (−14.1 °F; 247.6 K)
Boiling point    117.9 °C (244.2 °F; 391.0 K)
Solubility in water    7% (20°C)
Vapor pressure    13 mmHg (20°C)

Applications of Epichlorohydrine
Glycerol and epoxy resins synthesis
Epichlorohydrine is mainly converted to bisphenol A diglycidyl ether, a building block in the manufacture of epoxy resins. It is also a precursor to monomers for other resins and polymers. Another usage is the conversion to synthetic glycerol. However, the rapid increase in biodiesel production, where glycerol is a waste product, has led to a glut of glycerol on the market, rendering this process uneconomical. Synthetic glycerol is now used only in sensitive pharmaceutical, and biotech applications where quality standards are very high.

Minor and niche applications of Epichlorohydrine
Epichlorohydrine is a versatile precursor in the synthesis of many organic compounds. For example, it is converted to glycidyl nitrate, an energetic binder used in explosive and propellant compositions. The Epichlorohydrine is reacted with an alkali nitrate, such as sodium nitrate, producing glycidyl nitrate and alkali chloride. It is used as a solvent for cellulose, resins, and paints, and it has found use as an insect fumigant.

Polymers made from Epichlorohydrine, e.g., polyamide-Epichlorohydrine resins, are used in paper reinforcement and in the food industry to manufacture tea bags, coffee filters, and sausage/salami casings as well as with water purification.

An important biochemical application of Epichlorohydrine is its use as crosslinking agent for the production of Sephadex size-exclusion chromatographic resins from dextrans.

Safety of Epichlorohydrine
Epichlorohydrine is classified by several international health research agencies and groups as a probable or likely carcinogen in humans. Prolonged oral consumption of high levels of Epichlorohydrine could result in stomach problems and an increased risk of cancer. Occupational exposure to Epichlorohydrine via inhalation could result in lung irritation and an increased risk of lung cancer.

Epichlorohydrine is a volatile and flammable, clear, colorless, liquid, chlorinated cyclic ether with an irritating, chloroform-like odor that emits toxic fumes of hydrochloric acid and other chlorinated compounds when heated to decomposition. Epichlorohydrine is used in the manufacture of epoxy resins, synthetic glycerin and elastomers. Exposure to Epichlorohydrine irritates the eyes, skin and respiratory tract, and can cause chemical pneumonitis, pulmonary edema, and renal lesions. This substance also affects the blood. Epichlorohydrine is reasonably anticipated to be a human carcinogen and may be associated with an increased risk of developing respiratory cancer.

NCI Thesaurus
Epichlorohydrine is an epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine. It is an organochlorine compound and an epoxide. It derives from a 1,2-epoxypropane.

(Chloromethyl)oxirane, also known as alpha-Epichlorohydrine or 1-chloro-2, 3-epoxypropane, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms) (Chloromethyl)oxirane exists as a liquid, soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, (chloromethyl)oxirane is primarily located in the cytoplasm (Chloromethyl)oxirane can be biosynthesized from 1, 2-epoxypropane.

Epichlorohydrine is a chlorinated epoxy compound used as an industrial solvent.Epichlorohydrine is a strong skin irritant and carcinogen.
(Chloromethyl)oxirane is used for cross-linking dextrose units in food starch (Chloromethyl)oxirane belongs to the family of Epoxides.
These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).Molecular Formula of Epichlorohydrine is C3H5ClO.

Epichlorohydrine is mainly used in the production of epoxy resins. Acute (short-term) inhalation exposure to Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine as a Group B2, probable human carcinogen.
Epichlorohydrine is a clear colorless liquid with an irritating chloroform-like odor. Density 9.8 lb / gal. Flash point 87°F. Polymerizable. If polymerization takes place inside a closed container, the container is subject to violent rupture. Irritates the skin and respiratory system. Toxic by ingestion. A confirmed carcinogen. Vapors heavier than air. Used to make plastics and as a solvent.

Colorless liquid with a slightly irritating, chloroform-like odor.Epichlorohydrine is colorless liquid.Odor of Epichlorohydrine is sweet, pungent or chloroform-like... generally perceived as a slightly irritating chloroform like odor.
Boiling Point of Epichlorohydrine is 241.7° F at 760 mm Hg.Melting Point of Epichlorohydrine -54.4 to -14.1° F.Flash Point of Epichlorohydrine 93° F and solubility 50 to 100 mg/mL at 72° F.Density of Epichlorohydrine 1.18 to 1.801 at 68° F.Epichlorohydrine can be oxidized by free radical process in liquid or gas phases; these reactions may occur as photochemically initiated atmospheric reactions.

The primary use of Epichlorohydrine is in the production of epoxy resins used in coatings, adhesives, and plastics.
Epichlorohydrine is also used in the manufacture of synthetic glycerine, textiles, paper, inks and dyes, solvents, surfactants, and pharmaceuticals.
Epichlorohydrine is also listed as an inert ingredient in commercial pesticides.Industry Uses of Epichlorohydrine are adhesives and sealant chemicals,intermediates,solvents (which become part of product formulation or mixture).

Consumer Uses of Epichlorohydrine are Adhesives and Sealants,Paints and Coatings.

Epichlorohydrine is a chlorinated epoxy component used as an industrial solvent. Epichlorohydrine is skin irritant and carcinogenic.
(Chloromethyl) oxirane is used for crosslinking dextrose units of the Epoxides family of oxyran in food starch (Chloromethyl).
These are compounds containing three ring atoms (one oxygen and two carbon atoms) a ringed ether. The molecular formula of Epichlorohydrine is C3H5ClO.

Epichlorohydrine is mainly used in the production of epoxy resins. Acute (short-term) respiratory exposure to Epichlorohydrine at the workplace caused irritation of the eyes, respiratory tract and workers' skin.
In case of high exposure, people may experience nausea, vomiting, cough, lactating breathing, inflammation of the lungs, pulmonary edema and renal lesions.

Exposure to Epichlorohydrine in people in the air is associated with chronic (long-term) occupational exposure, high levels of respiratory diseases and hematological effects.

In rodents administered Epichlorohydrine by inhalation for acute or chronic periods, nasal passages, respiratory tract and kidneys were damaged. An increase in the rate of tumor of the nasal cavity was observed in inhaled rats.

EPA has classified Epichlorohydrine as a possible human carcinogen, Group B2.
Epichlorohydrine is a clear colorless liquid with a clear chloroform-like odor. Density 9.8 lb / gal. The flash point is 87 ° F. It can be polymerized. If polymerization takes place in a closed container,
The container is subject to severe tearing. Irritating to skin and respiratory system. Toxic when swallowed. Carcinogen detected. Used in plastic making and as a solvent.

Epichlorohydrine is a colorless liquid with a slightly irritant and chloroform-like odor. It can be oxidized by flux free radical treatment of Epichlorohydrine. These reactions can occur in the form of photochemically initiated atmospheric reactions.
The primary use of Epichlorohydrine is used in the production of epoxy resins used in coatings, adhesives and plastics.

Epichlorohydrine is also used in the production of synthetic glycerin, textiles, paper, inks and dyes, solvents, surfactants and pharmaceutical products.
Epichlorohydrine is listed as an inert ingredient in commercial insecticide. The use of Epichlorohydrine in the industry are adhesives and sealant chemicals, intermediates, solvents (part of the product formulation or mixture).).
Consumer uses of Epichlorohydrine are adhesives and sealants, paints and coatings.

Epichlorohydrine (chloromethyloxirane) is an organic substance , a chloro derivative of propylene oxide, with the formula CH 2 (O) CH-CH 2 Cl. It is widely used in organic synthesis, used in the production of epoxy resins and glycerin. Highly toxic, irritant.

Epichlorohydrine is an epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine. It is an organochlorine compound and an epoxide. It derives from a 1,2-epoxypropane.

Preferred IUPAC name
2-(Chloromethyl)oxirane
Other names
(Chloromethyl)oxirane
Epichlorohydrine
1-Chloro-2,3-epoxypropane
γ-Chloropropylene oxide
Glycidyl chloride

Physical properties of Epichlorohydrine
It is a colorless mobile transparent liquid with an irritating odor of chloroform , poorly soluble in water , well in most organic solvents. Forms an azeotropic mixture with water with a boiling point of +88 ° C and contains 75% Epichlorohydrine. Forms azeotropic mixtures with a large number of organic liquids. Epichlorohydrine is optically active due to the presence of an asymmetric carbon atom.

Chemical properties of Epichlorohydrine
Epichlorohydrine is a chemically highly reactive compound with an active epoxy group and a mobile chlorine atom.

Halogenation reaction of Epichlorohydrine
When chlorine interacts with Epichlorohydrine under normal conditions, 3,3-dichloropropylene oxide (3,3-dichloroepoxypropylene) is formed:

Hydrochlorination reaction of Epichlorohydrine
Easily adds hydrogen chloride at ordinary temperature both in solution and in anhydrous medium, with the formation of 1,3-dichlorohydrin:

Dehydrochlorination reaction of Epichlorohydrine
In the presence of small amounts of alkali, Epichlorohydrine easily attaches compounds containing one or more mobile hydrogen atoms to form chlorohydrins :

With an increase in the alkali concentration, the reaction proceeds with the elimination of hydrogen chloride and the reduction of the epoxy group, but in a different position :

Hydrolysis reaction of Epichlorohydrine
With an excess of alkali ( sodium carbonate is most often used ) and at a temperature of 100 ° C, Epichlorohydrine is slowly converted into glycerin

Hydration reaction of Epichlorohydrine
in the presence of dilute inorganic acids ( sulfuric or orthophosphoric ), Epichlorohydrine forms glycerol α-monochlorohydrin
As the temperature rises, the hydration of Epichlorohydrine increases.

Esterification reaction of Epichlorohydrine
When Epichlorohydrine interacts with alcohols , the epoxy ring opens with the formation of a hydroxyl group in position 2 and with the formation of an ether

Amination reaction

Epichlorohydrine already at ordinary temperature adds ammonia or amines with ring opening

Epichlorohydrine reacts with diphenylolpropane to form a polymeric diglycidal ether

Diglycidether
This reaction is an example of the production of epoxy resins , which have recently become very widespread due to their exceptional properties

Polymerization reaction of Epichlorohydrine
Epichlorohydrine is capable of polymerizing. Depending on the catalyst used, mobile liquids, high-viscosity oils or resin-like products are obtained

Application of Epichlorohydrine
It is used as an intermediate for the synthesis of glycerin derivatives , dyes and surfactants ; for the production of synthetic materials (mainly epoxy resins ).

Toxicology and safety of Epichlorohydrine
The general nature of the action
It has an irritating and allergic effect. In experiments on animals, it selectively affects the kidneys. Penetrates the skin.

Epichlorohydrine is a highly toxic and flammable compound . Epichlorohydrine vapors, when inhaled, even in small concentrations, cause nausea , dizziness and lacrimation , and with
prolonged exposure lead to more serious consequences (often severe pulmonary edema occurs). Epichlorohydrine on contact with the skin and prolonged contact causes dermatitis,

Chemical formula: С 3 H 5 ClO

Form of release and appearance of Epichlorohydrine: colorless liquid with a pungent odor of chloroform.

Production of Epichlorohydrine
The main production method is based on the interaction of allyl chloride (obtained by chlorination of propylene) and hypochlorous acid to obtain chlorine derivatives of propyl alcohols. Further, in the presence of alkali, the epoxy cycle closes. ECH is also obtained by processing glycerin, an available by-product of biodiesel production. The chemical route of synthesis is similar - chlorination of glycerol and subsequent closure of the epoxy bond in the presence of alkali.

Properties of Epichlorohydrine:
Poorly soluble in water;
Miscible with most polar organic solvents
Melting point -27 ° C; boiling point 118 ° C

Main areas and methods of application of Epichlorohydrine
Main application - production of epoxy resins and adhesives; ion exchange resins; is also an intermediate in the production of synthetic glycerin. It is a similar raw material for a variety of organic synthesis products, including dyes, surfactants, pharmaceuticals, lubricants. Can be used as a solvent.

SPECIFICATIONS of Epichlorohydrine
Index    Value
Basic substance content, wt%    99.9 min
Moisture content, ppm    500 max
APHA chromaticity    15 max
Density at 20 О С, kg / l    1.180 - 1.1185
Packing:
-   Metal barrels of 240 kg net
- Bulk in ISO tanks.

Safety and storage rules of Epichlorohydrine
The product is highly toxic and flammable. Avoid inhalation of product vapors and skin contact. The product should be stored in dry ventilated areas away from sources of heat, sparks and open flames. Store in tightly closed original containers.

Epichlorohydrine can be oxidized by free radical process in liquid or gas phases; these reactions may occur as photochemically initiated atmospheric reactions.

Characterized by two potentially reactive sites: the epoxide ring and the chlorine atom. Presence of the highly strained 3-membered ring makes Epichlorohydrine a relatively reactive compound.

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, Epichlorohydrine, 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 Epichlorohydrine, 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 Epichlorohydrine, 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 Epichlorohydrine is metabolized rapidly, part being excreted as carbon dioxide via the lungs and part as water-soluble compounds via the urine.

The major urinary metabolite of (14)C-Epichlorohydrine, 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. Epichlorohydrine was metabolized in vitro by rat liver microsomes to alpha-chlorohydrin, but 1,2-dibromo-3-chloroproane was not metabolized to Epichlorohydrine or alpha-chlorohydrin under similar conditions. Covalent binding of radioactivity to liver microsomal proteins occurred for both substrates, but was less for (14)C-Epichlorohydrine 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 Epichlorohydrine, but decreased the amojnt of (14)C-1,2-dibromo-3-chloropropane which was bound. The data indicate the Epichlorohydrine 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.

Within 20 min of the oral or intraperitoneal administration of Epichlorohydrine in mice, the compound was no longer detectable in the blood by gas chromatography with mass spectrometric detection, while the level of 3-chloro-1,2-propanediol reached a peak. The latter was measurable up to 5 hr after exposure.

Used mainly for the production of glycerol, unmodified epoxy resins (Epichlorohydrine-bisphenol A resin), and elastomers. Several other products made from epihydrin are glycidyl ethers, Epichlorohydrine-polyamide resins, and alkyl glyceryl ether solfonate salts.

Epichlorohydrine 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 Epichlorohydrine.

Epichlorohydrine in water can be analyzed by direct injection of an aqueous sample into a gas chromatograph. The potential sensitivity range is 1-10 ppm. The determination of Epichlorohydrine in water at the level of a few parts per billion has been performed by extraction of aqueous samples with ether and analysis of the extract by gas chromatography-mass spectrometry. This method provides the highest sensitivity and high specificity.

Epichlorohydrine was determined in water samples by extracting the water samples with carbon tetrachloride and spectrophotometric determination of absorbance at 1,274 1/cm (wavelength not given).

Epichlorohydrine has been determined by volumetric or titrimetric analysis.

Levels of Epichlorohydrine in male mice blood samples were determined by a gas chromatograph with a flame ionization detector (extraction method not given).

Health Hazards of Epichlorohydrine
This compound is caustic as both a liquid and gas. Irritation of the eyes and skin, and skin sensitization has been observed. Exposure to Epichlorohydrine has caused inflammation of the lungs, asthmatic bronchitis, and liver and kidney damage. In acute poisonings, death may be caused by respiratory paralysis.

Hazards Summary of Epichlorohydrine
Epichlorohydrine is mainly used in the production of epoxy resins. Acute (short-term) inhalation exposure to Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine as a Group B2, probable human carcinogen.

Epichlorohydrine effect on the skin, eyes, and respiratory tract may be delayed for several hours. Epichlorohydrine causes dermatitis.

Fire Fighting
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. Epichlorohydrine may react violently with water. Use water spray, dry chemical, foam or carbon dioxide. Water spray may be used to dilute spills to non-flammable mixtures. If leak or spill has not ignited, use water spray to disperse the vapors. Keep fire-exposed containers cooled with water.

Epichlorohydrine 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.

Epichlorohydrine should be stored in tightly closed, labeled containers in fire-proof, cool, dry rooms. Apply ventilation across the floor. Epichlorohydrine 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.

Epichlorohydrine 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.

The heat evolved by the reaction of Epichlorohydrine with acids, alkalis, active hydrogen, including water, and certain salts may cause overflow from the container or explosion.

In a train accident in January 1978 in West Virginia more than 20,000 gal of Epichlorohydrine were spilled about 150 feet from the Ohio River near the center of the town of Point Pleasant. Although the chemical was reported not to have contaminated the Ohio River, local officials ordered the removal of about 1 acre of soil (several feet deep). The level of Epichlorohydrine in water from wells closest to the spill area at the time was 75 ppm. The city's wells were closed, after an estimation of subsurface movement. Since the closing of the wells, water has been obtained from a radial collector several miles from the city.

Evaluation: There is inadequate evidence in humans for the carcinogenicity of Epichlorohydrine. There is sufficient evidence in experimental animals for the carcinogenicity of Epichlorohydrine. Overall evaluation: Epichlorohydrine is probably carcinogenic to humans (Group 2A). In making the overall evaluation, the Working Group took into consideration the known chemical reactivity of Epichlorohydrine and its direct activity in a wide range of genetic tests.

Toxicity Summary of Epichlorohydrine

IDENTIFICATION:
Epichlorohydrine 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 Epichlorohydrine is corrosive to steel. Epichlorohydrine has a chloroform like odor. It is soluble in water. Epichlorohydrine 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 Epichlorohydrine, 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 Epichlorohydrine. Burning of the eyes and nasal mucosa was reported along with throat irritation. Seven cases of Epichlorohydrine spills on the hands, thighs or feet have been described. In two cases Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine for 15-60 minutes, most died exhibiting severe systemic poisoning. Within 7 days, 50% of the rabbits died after the application of Epichlorohydrine on an occluded patch of shaved skin for 24 hr. Eight hours after oral administration of Epichlorohydrine 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 Epichlorohydrine was absorbed from the gastrointestinal tract of rats. After absorption by rats, Epichlorohydrine was distributed widely through out many tissues. Concentrations of Epichlorohydrine 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. Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine which included increased pentobarbital sleeping time in mice and a dose related decrease in histaminases activity in rats. Application of 80% solution Epichlorohydrine 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 Epichlorohydrine in cotton seed oil. Groups of 20 male Wistar rats received Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine 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 Epichlorohydrine 7 hr/day between the 6th and 15th or the 18th day of pregnancy. Epichlorohydrine is acutely toxic to blue and green algae, bacteria, crustacea and fish.

Acute Exposure/ No sensitization was observed when Epichlorohydrine was repeatedly applied to the skin of guinea pigs at 0.01% in cotton seed oil or in another study using a modified Draize sensitization test. In another study, sensitization in guinea pigs was reported. The test procedure consisted of four applications of Epichlorohydrine to the back of the guinea pig, an intradermal injection of Freund's adjuvant at the third application, and a 2-week rest period, followed by a challenge to Epichlorohydrine.

Epichlorohydrine's production and use as a solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, and cement for celluloid may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 16.4 mm Hg at 25 °C indicates Epichlorohydrine will exist solely as a vapor in the ambient atmosphere. Vapor-phase Epichlorohydrine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 36 days. If released to soil, Epichlorohydrine is expected to have very high mobility based upon an estimated Koc of 40. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole. Epichlorohydrine may volatilize from dry soil surfaces based upon its vapor pressure. Epichlorohydrine is expected to undergo hydrolysis in moist soil surfaces. Limited data suggest that Epichlorohydrine may undergo biodegradation in acclimated soil and surface waters. If released into water, Epichlorohydrine is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 19 hours and 12 days, respectively. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is expected to be an important environmental fate process based upon hydrolysis half-lives of 8.2 days and 5.3 days in distilled water and simulated seawater, respectively. Occupational exposure to Epichlorohydrine may occur through inhalation and dermal contact with this compound at workplaces where Epichlorohydrine is produced or used. Use data suggest that the general population may be exposed to Epichlorohydrine via inhalation and dermal contact with products containing this compound.

Based on a classification scheme, an estimated Koc value of 40, determined from a log Kow of 0.45 and a regression-derived equation, indicates that Epichlorohydrine is expected to have very high mobility in soil. Volatilization of Epichlorohydrine from moist soil surfaces is expected to be an important fate process given an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole, calculated from a vapor pressure of 16.4 mm Hg and water solubility of 65,900 mg/L(5). The potential for volatilization of Epichlorohydrine from dry soil surfaces may exist based upon the vapor pressure. Epichlorohydrine may undergo hydrolysis in moist soil surfaces based on a hydrolysis half-life of 8.2 days in distilled water(6). Epichlorohydrine 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.

Based on a classification scheme, an estimated Koc value of 40, determined from a log Kow of 0.45 and a regression-derived equation, indicates that Epichlorohydrine is not expected to adsorb to suspended solids and sediment in water. Volatilization from water surfaces is expected based upon an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole, calculated from its vapor pressure of 16.4 mm Hg and water solubility of 65,900 mg/L(5). Using this estimated Henry's Law constant and an estimation method, volatilization half-lives for a model river and model lake are 19 hours and 12 days, respectively. According to a classification scheme(6), an estimated BCF of 3, from its log Kow and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis half-life of Epichlorohydrine is 8.2 days in distilled water and 5.3 days in simulated seawater(8). Epichlorohydrine 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.

According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere, Epichlorohydrine, which has a vapor pressure of 16.4 mm Hg at 25 °C, is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase Epichlorohydrine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 36 days, calculated from its rate constant of 4.4X10-13 cu cm/molecule-sec at 25 °C.

An unspecified amount of Epichlorohydrine reached 18% of its theoretical BOD in 1 week using an activated sludge inoculum and the Japanese MITI test. Pure cultures were able to biodegrade Epichlorohydrine rapidly to 3-chloro-1,2-propanediol. Epichlorohydrine 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. Epichlorohydrine was 67% biodegraded in an activated sludge degradability test following a 1 day acclimation period.

The rate constant for the vapor-phase reaction of Epichlorohydrine with photochemically-produced hydroxyl radicals has been measured as 4.4X10-13 cu cm/molecule-sec at 25 °C. This corresponds to an atmospheric half-life of about 36 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm. Epichlorohydrine hydrolyzes in distilled water to yield 1-chloro-2,3-propanediol, with a half-life of 8.2 days. Acid catalysis contributes less than 10% to the rate of hydrolysis and base catalysis is not detectable at pH<10. The hydrolysis half-life of Epichlorohydrine in 3% sodium chloride (simulated seawater) is 5.3 days. The reported hydrolysis half-life of Epichlorohydrine in acidic waters (pH = 2.5) was reported as 3.3 days and in alkaline waters (pH = 12) 2.6 days. Anions such as chloride attack the epoxide ring producing 1,3-dichloro-2-propanol. When irradiated in the presence of 5 ppm nitric oxide to simulate photochemical smog conditions, the half-life of Epichlorohydrine was 16 hours(5).

The Koc of Epichlorohydrine is estimated as 40, using a log Kow of 0.45 and a regression-derived equation. According to a classification scheme, this estimated Koc value suggests that Epichlorohydrine is expected to have very high mobility in soil.

An estimated BCF of 3 was calculated for Epichlorohydrine, using a log Kow of 0.45 and a regression-derived equation. According to a classification scheme, this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Henry's Law constant for Epichlorohydrine is estimated as 3.0X10-5 atm-cu m/mole from its vapor pressure, 16.4 mm Hg, and water solubility, 65,900 mg/L. This Henry's Law constant indicates that Epichlorohydrine is expected to volatilize from water surfaces. Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as 19 hours. The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as 12 days. However, this process may be superceded by rapid hydrolysis. Epichlorohydrine's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is expected to be an important fate process. Epichlorohydrine is expected to volatilize from dry soil surfaces based upon its vapor pressure.

Detected, not quantified in chemical industry effluent in Louisville, KY. Epichlorohydrine was identified, not quantified, in emissions from polyurethane carpet cushions. Atmospheric emissions of Epichlorohydrine were reported as 479,000 lbs/yr in the US in a 1983 study. Epichlorohydrine 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.

At a distance of 100 to 200 meters from a factory discharging Epichlorohydrine into the atmosphere in the former USSR, the airborne Epichlorohydrine concentration ranged from 0.5 to 1.2 mg/cu m. At a distance of 400 meters, levels in 5 out of 29 samples exceeded 0.2 mg/cu m; at 600 meters, Epichlorohydrine was identified, but not quantified.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 80,170 workers (14,921 of these were female) were potentially exposed to epichlorohyddrin in the US. Occupational exposure to Epichlorohydrine may occur through inhalation and dermal contact with this compound at workplaces where Epichlorohydrine is produced or used. Use data suggest that the general population may be exposed to Epichlorohydrine via inhalation and dermal contact with products containing this compound.