May form explosive mixture with air. Reacts explosively with carbon tetrachloride, strong bases. Also incompatible with strong acids. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Polymerization may be caused by heat above 99 C, peroxides, or oxidizers.
Colorless, mobile liquid with a pungent, mustard-like odor at high concentrations. At low
concentrations, odor resembles that of ethyl alcohol. Katz and Talbert (1930) and Dravnieks
(1974) reported experimental detection odor threshold concentrations of 3.3 mg/m3 (1.4 ppmv) and
5 mg/m3 (2.1 ppmv), respectively.
Male and female F344 rats were
given allyl alcohol in the drinking water at a concentration of
0 or 300 mg/L for 106 weeks. The incidence of tumors was
similar to that in controls . Male and female hamsters
were administered 2 mg allyl alcohol by oral gavage once a
week for 60 weeks. The incidence of tumors did not increase
significantly compared to controls.
Allyl alcohol is prepared by several different processes, the original is alkaline hydrolysis of allyl chloride
by steam injection at high temperatures. A more recent
commercial process used oxidation of propylene to acrolein,
which in turn reacts with a secondary alcohol to yield
allyl alcohol and a ketone. In this process, allyl alcohol is
not isolated, but its aqueous stream is converted directly to
glycerol. The most recent commercial process is isomerization
of propylene oxide over a lithium phosphate catalyst.
UN1098 Allyl alcohol Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquids, Inhalation Hazard Zone B.
Allyl alcohol is a flammable, colorless liquid. It has a pungent, mustard-like odor. It is used in making drugs, organic chemicals, pesticides, in the manufacture of allyl esters, and as monomers and prepolymers for the manufacture of resins and plastics. It has a large use in the preparation of pharmaceutical products, in organic synthesis, and as a fungicide and herbicide. Occupational workers engaged in industries such as the manufacture of drugs, pesticides, allyl esters, organic chemicals, resins, war gas, and plasticizers, are often exposed to this alcohol.
ChEBI: A propenol in which the C2C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.
Allyl alcohol presents a dangerous fire and explosion hazard when exposed to heat, flame, or oxidizing agents. Reacts violently or explosively with sulfuric acid, strong bases. Reacts violently with 2,4,6-trichloro-1,3,5-triazine and 2,4,6-tris(bromoamino)-1,3,5-triazine. Reacts with carbon tetrachloride to produce explosively unstable products [Lewis]. Mixing Allyl alcohol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, nitric acid, oleum, sulfuric acid [NFPA 491M. 1991].
Biological. Bridié et al. (1979) reported BOD and COD values of 1.79 and 2.12 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 alcohol is 2.21
Photolytic. Atkinson (1985) reported a rate constant of 2.59 x 10-11 cm3/molecule?sec at 298 K.
Based on an atmospheric OH concentration of 1.0 x 106 molecule/cm3, the reported half-life of
allyl alcohol is 0.35 d. The reaction of allyl alcohol results in the OH addition to the C=C bond
(Grosjean, 1997). In a similar study, Orlando et al. (2001) studied the reaction of allyl alcohol with
OH radicals at 298 K. Photolysis was conducted using a xenon-arc lamp within the range of 240–
400 nm in synthetic air at 700 mmHg. A rate constant of 4.5 x 10-11 cm3/molecule?sec was
reported. Products identified were formaldehyde, glycolaldehyde, and acrolein.
Chemical/Physical. Slowly polymerizes with time into a viscous liquid (Windholz et al., 1983).
Polymerization may be caused by elevated temperatures, oxidizers, or peroxides (NIOSH, 1997).
Toxic by skin absorption. Eye and upper
respiratory tract irritant. Questionable carcinogen.
Allyl alcohol is used in manufacture of allyl compounds, resins, plasticizers; fungicide and herbicide.
Suspected carcinogen. Poison by inhalation, ingestion, skin contact, subcutaneous, intraperitoneal, and possibly other routes. A slim, severe eye (human), and systemic irritant. Mutation data reported. Dangerous fire and explosion hazard when exposed to heat, flame, or oxidizers. Explosive or violent reaction with sulfuric acid, alkali + 2,4,6-trichloro-1,3,5triazine, or 2,4,6-tris(bromoamino)-1,3,5triazine. Reaction with carbon tetrachloride produces explosively unstable halogenated C4 epoxides. Incompatible with chlorosulfonic acid, HNO3, H2SO4, oleum, NaOH, dallyl phosphte, PCl3, and tri-nbromomelamine. When heated to decomposition it emits acrid smoke and fumes. To fight fire, use CO2, alcohol foam, dry chemical. See also ALLYL COMPOUNDS.
Used to make other chemicals and pharmaceuticals; as a laboratory chemical. Not currently registered in the United States as a pesticide or fungicide
Occupational workers should be careful during handling and use of allyl alcohol and wear
It can be dried with K2CO3 or CaSO4, or by azeotropic distillation with *benzene followed by distillation under nitrogen. It is difficult to obtain it free of peroxide. It has also been refluxed with magnesium and fractionally distilled [Hands & Norman Ind Chem 21 307 1945]. [Beilstein 1 IV 2079.]
Allyl alcohol is used as an intermediate compound for synthesizing raw materials such as epichlorohydrin C3H5ClO and 1,4- butanediol C4H10O2, and this development is bringing about expansion of the range of uses of allyl alcohol. The term allyl of allyl compounds is derived from allium, the Latin word for garlic.
The toxicity of allyl alcohol is moderately high, affecting primarily the eyes. The other target organs are the skin and respiratory system. Inhalation causes eyeirritation and tissue damage. A 25-ppmexposure level is reported to produce asevere eye irritation. It may cause atemporary lacrimatory effect, manifested by photophobia and blurred vision, for some hours after exposure. Occasional exposure of a person to allyl alcohol does not indicate chronic or cumulative toxicity. Dogterom and associates (1988) investigated the toxicity of allyl alcohol in isolated rathepatocytes. The toxicity was independent of lipid peroxidation, and acrylate was found to be the toxic metabolite Ingestion of this compound may cause irritation of the intestinal tract. The oral LD50 value in rats is 64 mg/kg (NIOSH 1986).
Used to induce a mouse model of liver damage that has been used to study the mechanisms of hepatotoxicity and hepatic stem cell-mediated repair.
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable at ordinary temperatures and pressures; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
A clear colorless liquid with a mustard-like odor. Flash point 70°F. Very toxic by inhalation and ingestion. Less dense than water (7.1 lb / gal). Vapors are heavier than air. Prolonged exposure to low concentrations or short exposure to high concentrations may have adverse health effects from inhalation.
Allyl alcohol vapor may explode if ignited in confined areas. Combustion products may be poisonous. The vapor is heavier than air and flashback along vapor trail may occur. Gives off toxic fumes when heated. May react vigorously with oxidizing materials, carbon tetrachloride, acids, oleum, sodium hydroxide, diallyl phosphite, potassium chloride, or tri-n-bromomelamine.
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration after dilution with a flammable solvent.
Air & Water Reactions
Highly flammable. Water soluble.
Allyl alcohol is used to produce glyceroland acrolein and other allylic compounds. Itis also used in the manufacture of militarypoison gas. The ester derivatives are used inresins and plasticizers.