Description
Allyl glycidyl ether is a colorless liquid clycidyl ether with a pleasant odor. The compound is insoluble in water and less dense than water, therefore can easily float on water. When ingested or inhaled, allyl glycidyl ether is mildly toxic. It is not classified as a human carcinogen.
Preparation
In a condensation reaction, epichlorohydrin and allyl alcohol are used in the synthesis of allyl glycidyl ether.
Uses
Allyl glycidyl ether is utilized in sealants and adhesives. It is also used in the production of polyvinylcaprolactam.
Chemical Properties
Allyl glycidyl ether is a stable, colorless, flammable liquid with a pleasant odor. It is incompatible
with strong oxidizers agents, acids, and bases. It may form peroxides in storage if
in contact with air.
Physical properties
Clear, colorless, watery, combustible liquid with a strong, pleasant odor. An odor threshold value
of 47 mg/m
3 was reported (quoted, Verschueren, 1983).
Uses
AGE can be used as a terminal epoxy group in the development of adhesive surfaces by hydrosilylation process.
It can also be used in the synthesis of polymeric electrolytes for the fabrication of lithium batteries.
Useful in hydrosilylation, including the H
2PtCl
6·xH
2O catalyzed hydrosilylation of siloxanes to epoxysiloxanes.
Production Methods
AGE is manufactured through the condensation of allyl
alcohol and epichlorohydrin with subsequent dehydrochlorination
with caustic to form the epoxy ring.
Definition
The length of time something has existed.
General Description
A colorless liquid with a pleasant odor. Flash point 135°F. Slightly less dense than water and insoluble in water. Hence floats on water. Poisonous by ingestion and mildly toxic by inhalation and skin contact. Very irritating to skin and eyes. Used to make other chemicals.
Air & Water Reactions
Flammable. Insoluble in water.
Reactivity Profile
Allyl glycidyl ether reacts violently with oxidizing agents. Can form peroxides. Polymerizes readily [Handling Chemicals Safely 1980. p.128].
Hazard
Skin, eye, and upper respiratory tract irri-
tant, and dermatitis. Questionable carcinogen.
Health Hazard
Occupational workers exposed to allyl glycidyl ether develop severe symptoms of poisoning
that include, but are not limited to, irritation of the eyes, redness, pain, blurred vision,
deep skin burns, respiratory system; causes damage of the mucous membranes, dermatitis,
burning sensation, shortness of breath, headache, drowsiness, dullness, nausea, vomiting,
pulmonary edema, narcosis, possible hematopoietic and reproductive effects. Acute
exposure may cause CNS depression. The major target organs include the eyes, skin, respiratory
system, blood, and the reproductive system.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Contact allergens
Allyl glycidyl ether is a monoglycidyl derivative, used
as a reactive epoxy diluent for epoxy resins. As an
impurity, it was considered to be the sensitizing agent
in a plastic industry worker allergic to 3-glycidyloxypropyl
trimethoxysilane, an epoxy silane compound
used as a fixing additive in silicone and polyurethane
Safety Profile
Confirmed animal carcinogen. Poison by ingestion. Moderately toxic by inhalation and skin contact. Mutation data reported. A severe skin and eye irritant. Can cause central nervous system depression and pulmonary edema. A flammable liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical.When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS
Allyl glycidyl ether has an LD50 of 390 mg/kg (mouse, oral) and an LD50 of 1600 mg/kg (rat, oral). In rabbits, the dermal LD50 is 2550 mg/kg. Inhalational toxicity has been estimated: LC50 = 270 ppm (mice, 4 h) and 670 ppm (rats, 8 h)
Potential Exposure
Used as a solvent and emulsifier; making epoxy resins, chlorinated compounds; and rubber.
Carcinogenicity
In a 2-year inhalation carcinogenicity
study in Osborne Mendel rats and B6C3F1 mice
(50 of each sex at each exposure level), animals were exposed
to concentrations of 0, 5, or 10 ppm AGE, 6 h/day, 5 days/
week. Although occasional respiratory epithelial tumors
were observed, the NTP concluded the data provided only
equivocal evidence of carcinogenicity in male rats and
female mice. No evidence was obtained to support a carcinogenic
effect in female rats. Some evidence was provided
for a carcinogenic response in male mice, which included
three adenomas of the respiratory epithelium, dysplasia in
four mice, and focal basal cell hyperplasia of the respiratory
epithelium in the nasal passages of seven mice .
Environmental Fate
Biological. Bridié et al. (1979) reported BOD and COD values of 0.06 and 1.99 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. The ThOD for allyl glycidyl ether is
2.11 g/g.
Chemical/Physical. Hydrolysis of the epoxide ring is likely forming 1-allyloxy-2,3-
dihydroxypropane (Perez and Osterman-Golkar, 2000).
storage
Allyl glycidyl ether should be kept stored in a cool, dark, fi reproof area separated from
strong oxidants, strong bases, and strong acids.
Shipping
UN2219 Allyl glycidal ether, Hazard Class: 3; Labels: 3-Flammable liquid
Incompatibilities
Allyl glycidyl ether may form explosive mixture with air. Contact with acids or bases may cause explosive polymerization. Contact with oxidizers or amines may cause fire and explosions.
Toxics Screening Level
The initial risk screening level (IRSL) for allyl glycidyl ether (AGE) is 0.1 μg/m3 based on an annual averaging time.
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Precautions
During use and/or handling of allyl glycidyl ether, occupational workers should not be
near open flames, sparks, or smoking areas. For temperatures above 48°C, use a closedsystem
ventilation and explosion-proof electrical equipment. Workers should use protective
gloves, protective clothing, and avoid all contact.
