|
| | Allyl chloride Basic information |
| | Allyl chloride Chemical Properties |
| Melting point | -136 °C | | Boiling point | 44-46 °C(lit.) | | density | 0.939 g/mL at 25 °C(lit.) | | vapor density | 2.6 (vs air) | | vapor pressure | 20.58 psi ( 55 °C) | | refractive index | n20/D 1.414(lit.) | | Fp | −20 °F | | storage temp. | Store at +2°C to +8°C. | | solubility | alcohol: miscible(lit.) | | form | Powder/Solid | | Specific Gravity | 0.939 | | color | White | | Odor | pungent odor | | explosive limit | 3.3-11.2%(V) | | Water Solubility | 3.6 G/L (20 ºC) | | FreezingPoint | -134.5℃ | | Merck | 14,289 | | BRN | 635704 | | Henry's Law Constant | 2.69 at 25 °C (static headspace-GC, Welke et al., 1998) | | Exposure limits | NIOSH REL: TWA 1 ppm (3 mg/m3), STEL 2 ppm (6 mg/m3), IDLH 250 ppm;
OSHA PEL: TWA 1 ppm; ACGIH TLV: STEL 2 ppm. | | Stability: | Stable, but reacts vigorously or violently with a wide variety of materials. Highly flammable. Incompatible with strong oxidizing agents, acids, amines, peroxides, chlorides of iron and aluminium, BF3, aromatic hydrocarbons, Lewis acids, metals, caustics, ammonia, ferric chloride, ethylene imine, ethylenediamine. Heat and light sensitive | | LogP | 2.1 at 25℃ | | CAS DataBase Reference | 107-05-1(CAS DataBase Reference) | | NIST Chemistry Reference | 1-Propene, 3-chloro-(107-05-1) | | IARC | 3 (Vol. 36, Sup 7, 71, 125) In prep. | | EPA Substance Registry System | Allyl chloride (107-05-1) |
| | Allyl chloride Usage And Synthesis |
| Chemical Properties | colourless, light yellow or amber liquid with an unpleasant smell | | Chemical Properties | Allyl chloride is a colorless liquid, insoluble in water but soluble in common organic solvents.
Allyl chloride is prepared by the reaction of propylene with chlorine. It is a common
alkylating agent relevant to the manufacture of pharmaceuticals and pesticides. It is also a
component in some thermo-setting resins. Allyl chloride has been produced commercially since 1945 and is used almost exclusively as a chemical intermediate, principally in the
production of epichlorohydrin or as a raw material for epichlorohydrin. It is also used as
a chemical intermediate in the preparation of glycerin, glycerol chlorohydrins, glycidyl
ethers, allylamines, and allyl ethers of trimethylpropane, sodium allyl sulfonate, a series of
allyl amines and quaternary ammonium salts, allyl ethers, and a variety of alcohols, phenols,
and polyols. It is also used in pharmaceuticals as a raw material for the production of
allyl isothiocyanate (synthetic mustard oil), allyl substituted barbiturates (sedatives), and
cyclopropane (anesthetic); in the manufacture of specialty resins for water treatment and
to produce babiturate and hypnotic agents such as aprobarbital, butalbital, methohexital
sodium, secobarbital, talbutal, and thiamyl sodium. | | Chemical Properties | Allyl chloride is a highly reactive and flammable, colorless, brown or purple liquid, with an unpleasant, pungent odor. | | Physical properties | Colorless to light brown to reddish-brown liquid with a pungent, unpleasant, garlic-like odor. An
experimentally determined odor threshold concentration of 470 ppbv was reported by Leonardos et
al. (1969). | | Uses | Allyl chloride (3-chloropropene; 1-chloro-2-propene) is a chemical intermediate used in the synthesis of allyl compounds found in varnish, resins, polymers, pesticides, and pharmaceuticals (O’Neil, 2001). | | Uses | Allyl chloride is used in the synthesis of glycerol, allyl alcohol and epichlorohydrin. | | Uses | Manufacture of epichlorohydrin,
epoxy resin, glycerin pesticides, and sodium
allyl sulfonate | | Production Methods | Allyl chloride can be synthesized by reaction of allyl alcohol with HCl or by treatment of allyl formate with HCl in the presence of a catalyst (ZnCl2). | | Definition | ChEBI: Allyl chloride is an organochlorine compound. | | General Description | A clear colorless liquid with an unpleasant pungent odor. Flash point -20°F. Boiling point 113°F. Less dense than water (7.8 lb / gal) and insoluble in water. Hence floats on water. Vapor irritates skin, eyes and mucous membranes. Vapors are heavier than air. Long exposure to low concentrations or short exposure to high concentrations may have adverse health effects from inhalation or skin absorption. | | Air & Water Reactions | Highly flammable. Insoluble in water. | | Reactivity Profile | Allyl chloride presents a serious fire and explosion hazard when exposed to heat, flame or oxidizing agents. Polymerizes violently and exothermically with Lewis acids (aluminum chloride, boron trifluoride, sulfuric acid) or metals (aluminum, magnesium, zinc, or galvanized metal) [MCA SD-99, 1973]. Incompatible with acids (nitric acid, chlorosulfonic acid, oleum), with strong bases (sodium hydroxide, potassium hydroxide), with ethyleneimine and ethylenediamine [Lewis, 3rd ed., 1993, p. 36]. Attempts to alkylate benzene or toluene using Allyl chloride in the presence of ethylaluminum chlorides have led to explosions. | | Hazard | Skin and eye irritant. Upper respiratory
tract irritant, liver and kidney damage. Question-
able carcinogen.
| | Health Hazard | Causes marked irritation of skin and may burn. Burns the eyes; effect may be delayed. | | Health Hazard | Allyl chloride is toxic and flammable. Exposures to allyl chloride cause a cough, sore throat,
headache, dizziness, weakness, respiratory distress, abdominal pain, burning sensation,
vomiting, and loss of consciousness. After acute inhalation exposures to high levels of
allyl chloride, workers developed irritation of the eyes and respiratory passages, loss of
consciousness, and fatal injury. Prolonged and intense exposure produced conjunctivitis,
reddening of eyelids, and corneal burn, damage to the CNS, causing motor and sensory
neurotoxic damage, and the heart and respiratory system, causing the onset of pulmonary
edema in humans. Laboratory rabbits exposed to allyl chloride through inhalation developed
degenerative changes that included dilation of sinusoids and vacuolar degeneration
in the liver, congestion or cloudy swelling and fatty degeneration of the epithelium of the
renal convoluted tubules, and thickening of the alveolar septa in the lungs. The exposed cat
exhibited only muscle weakness and unsteady gait toward the end of the exposure period. | | Fire Hazard | Special Hazards of Combustion Products: Releases irritating hydrogen chloride gas on combustion | | Flammability and Explosibility | Highlyflammable | | Safety Profile | Suspected carcinogen with experimental tumorigenic data. Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion, inhalation, and skin contact. Experimental teratogenic and reproductive effects. A skin and eye irritant. Human mutation data reported. Chronic exposure may cause liver and lildney damage. The vapors of allyl chloride are quite irritating to the eyes, nose, and throat. Contact of the liquid with the skin may lead, in addition to local vasoconstriction and numbness, to rapid absorption and distribution through the body. If remedial measures are not taken promptly, such contact may result in burns and internal injuries. Inhalation may cause headache, dizziness, and in htgh concentration, loss of consciousness; however, even in low concentration, its odor in most cases is irritating enough to give warning of its presence. Concentration of the vapors high enough to cause serious effects, includlng damage to the lungs, especially on repeated exposure, may not be intolerable. Consequently, the warning characteristics should never be disregarded. In general, precautions should be taken AT ALL TIMES to avoid splllage and accumulation of noticeable concentration of the vapors in the atmosphere. Acute exposure in experimental animals has resulted in marked inflammation of lungs, irritation of skin, and swelling of the hdneys. Chronically exposed animals have shown degenerative changes in the liver and kidneys. Reported human exposures have been principally cases of irritation of the eyes, skin, and respiratory tract, sometimes accompanied by aches and pains in the bones. Liver and hdney injury is possible. Dangerous fire and explosion hazard when exposed to heat, flame, or oxidlzers. Vigorous or explosive reaction above -7O℃ with alkyl aluminum chlorides (e.g., trichlorotriethyl dialuminum, ethyl aluminum dichloride, or diethyl aluminum chloride) + aromatic hydrocarbons (e.g., benzene or toluene). Violently exothermic polymerization reaction with Lewis acids (e.g., aluminum chloride, boron trifluoride, or sulfuric acid) and metals (e.g., aluminum, magnesium, zinc, or galvanized metals). Incompatible with HNO3, ethylene imine, ethylenedlamine, chlorosulfonic acid, oleum, NaOH. To fight fire, use CO2, alcohol foam, dry chemical. See also CHLORINATED HYDROCARBONS; ALIPHATIC; ALLYL COMPOUNDS; and CHLORIDES. Storage and Handling: Keep cool, away from heat sources. Maintain good vendation. Work in a fume hood or with closed system if possible; otherwise, use adequate vendation so that the odor of allyl chloride does not persist. If it should be necessary to enter an area in which the odor of allyl chloride is at all noticeable, use a gas mask equipped with an “organic vapor” canister. Do not dlsregard the warning odor or eye irritation of allyl chloride | | Potential Exposure | Allyl chloride is used as a chemical intermediate and in making allyl compounds, epichlorohydrin, and glycerol. | | Carcinogenicity | The IARC found that it could not
classify AC as a human carcinogen on the basis of available
data. In contrast, EPA considers AC to be a possible
human carcinogen and has ranked it in EPA’s Group
C. This classification was based on a low
incidence of forestomach tumors in female mice and positive
results in a variety of genetic toxicity tests. However, the
forestomach tumor data were not used for quantitative cancer
risk assessment. AC is a strong alkylating agent and is
structurally similar to other forestomach carcinogens, such
as propylene oxide and epichlorohydrin, which cause tumors
at the site of exposure.
Olsen reported on a cohort of 1064 men employed at a
Texas plant in epoxy resin, glycerin, andAC/epichlorohydrin
production between 1957 and 1986 and followed up through
1989. There were 66 total deaths [standardized mortality
ratio (SMR)=0.8; 95% CI 0.6–1.0] and 10 cancers
(SMR=0.5; CI 0.2–0.9).However, the authors noted that the
cohort was limited due to sample size, duration of follow-up,
small numbers of deaths both expected and found, and the
limited exposure potential. | | Environmental fate | Biological. Bridié et al. (1979) reported BOD and COD values of 0.23 and 0.86 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C and stirred for a period of 5 d. When a sewage seed was
used in a separate screening test, a BOD value of 0.42 g/g was obtained. The ThOD for allyl
chloride is 1.67 g/g.
Photolytic. Anticipated products from the reaction of allyl chloride with ozone or OH radicals in
the atmosphere are formaldehyde, formic acid, chloroacetaldehyde, chloroacetic acid, and
chlorinated hydroxy carbonyls (Cupitt, 1980).
Chemical/Physical. Hydrolysis under alkaline conditions will yield allyl alcohol (Hawley,
1981). The estimated hydrolysis half-life in water at 25 °C and pH 7 is 2.0 yr (Mabey and Mill,
1978). | | Shipping | UN1100 Allyl chloride, Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous materials | | Purification Methods | Likely impurities include 2-chloropropene, propyl chloride, iso-propyl chloride, 3,3-dichloropropane, 1,2-dichloropropane and 1,3-dichloropropane. Purify it by washing with conc HCl, then with Na2CO3 solution, dry it with CaCl2, and distil it through an efficient column [Oae & Vanderwerf J Am Chem Soc 75 2724 1953]. [Beilstein 1 IV 738.] LACHRYMATORY, TOXIC. | | Incompatibilities | Contact with water forms hydrochloric acid. Keep away from strong oxidizers, acids, aluminum, amines, peroxides, chlorides of iron and aluminum; magnesium, zinc. | | Waste Disposal | 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. Controlled incineration at a temperature of 982 C for 2 seconds minimum. |
| | Allyl chloride Preparation Products And Raw materials |
| Raw materials | Hydrochloric acid-->Chlorine-->Copper(I) chloride-->Oxygen-->Allyl alcohol-->PROPYLENE-->2-Amino-3-chlorobenzoic acid-->Hexanoyl chloride-->Tellurium-->1,2,3-Trichloropropane-->1,2-DICHLOROPROPENE | | Preparation Products | Epichlorohydrin-->1-Bromo-3-chloropropane-->Eugenol-->Molosultap-->3-(2-METHYL-1,3-THIAZOL-4-YL)BENZOIC ACID-->2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one-->3-(2-BROMOACETYL)BENZOIC ACID-->ETHYL 4-ACETYLBENZOATE-->3-ACETYLBENZONITRILE-->3-ACETYLBENZOIC ACID-->3-(2-Bromoacetyl)benzonitrile-->tert-Butyl carbamate-->Imazalil-->Cartap hydrochloride-->1-Chloro-2-propanol-->Thiocyclam-->4-Phenyl-1-butene-->1,3-Dichloropropene-->1,3-Dichloro-2-propanol-->Allylamine-->Fluorochloridone-->[[o-(allyloxy)phenoxy]methyl]oxirane-->Allylthiourea-->Diallyl phthalate-->1,2,3-Trichloropropane-->Neophyl chloride-->Allylmagnesium chloride-->Thiocyclam hydrogen oxalate-->2-(Allyloxy)phenol-->N,N-Dimethylallylamine-->Flocculant ST-->fixing agent TCD-R-->2-(1-hydroxy-3-butenyl)-5-methyl furan-->POLY DIMETHYL DIALLYL AMMONIUM CHLORIDE-->1,5-HEXADIENE-->1,2-Dibromo-3-chloropropane |
|
