Allyl chloride
- CAS No.
- 107-05-1
- Chemical Name:
- Allyl chloride
- Synonyms
- 3-CHLOROPROPENE;Chloropropene;3-CHLORO-1-PROPENE;CH2=CHCH2Cl;Barchlor;3-Chloroprene;Allile;NCI-C04615;Allylchlor;Allylchloide
- CBNumber:
- CB9852695
- Molecular Formula:
- C3H5Cl
- Molecular Weight:
- 76.52
- MOL File:
- 107-05-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/30 19:52:35
| 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 |
n |
| Flash point | −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. |
| Dielectric constant | 8.2（20℃） |
| 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) |
| IARC | 3 (Vol. 36, Sup 7, 71, 125) In prep. |
| NIST Chemistry Reference | 1-Propene, 3-chloro-(107-05-1) |
| EPA Substance Registry System | Allyl chloride (107-05-1) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |     GHS02,GHS07,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H225-H302+H312+H332-H315-H319-H341-H351-H371-H372-H400 | |||||||||
| Precautionary statements | P210-P273-P280-P303+P361+P353-P304+P340+P312-P308+P311 | |||||||||
| Hazard Codes | F,Xn,N,T | |||||||||
| Risk Statements | 45-46-11-20/21/22-36/37/38-48/20-50-68-40-39/23/24/25-23/24/25-48/23/24/25 | |||||||||
| Safety Statements | 53-26-36/37-45-61-46-25-16-7 | |||||||||
| OEB | B | |||||||||
| OEL | TWA: 1 ppm (3 mg/m3), STEL: 2 ppm (6 mg/m3) | |||||||||
| RIDADR | UN 1100 3/PG 1 | |||||||||
| WGK Germany | 2 | |||||||||
| RTECS | UC7350000 | |||||||||
| F | 19 | |||||||||
| Autoignition Temperature | 390 °C | |||||||||
| Hazard Note | Flammable | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 2903 29 00 | |||||||||
| HazardClass | 3 | |||||||||
| PackingGroup | I | |||||||||
| Toxicity | LD50 orally in rats: 0.7 g/kg (Smyth, Carpenter) | |||||||||
| IDLA | 250 ppm | |||||||||
| NFPA 704 |
|
Allyl chloride price More Price(12)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A30702 | Allyl chloride reagent grade, 98% | 107-05-1 | 500ML | ₹2542.55 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A30702 | Allyl chloride reagent grade, 98% | 107-05-1 | 1L | ₹3513.15 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.00257 | 3-Chloro-1-propene (stabilised with propylene oxide) for synthesis | 107-05-1 | 100ML | ₹3510 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.00257 | 3-Chloro-1-propene (stabilised with propylene oxide) for synthesis | 107-05-1 | 1L | ₹4880 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 236306 | Allyl chloride ReagentPlus?, 99% | 107-05-1 | 100ML | ₹2015.05 | 2022-06-14 | Buy |
Allyl chloride Chemical Properties,Uses,Production
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.
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).
History
Allyl chloride, the only chloropropene of industrial importance, was first produced in 1857 by A. CAHOURS and A. W. HOFMANN by reacting phosphorus chloride with allyl alcohol. The name allyl is derived from the latin allium, meaning garlic. Inhalation of even small amounts of allyl chloride produces, after a short time, the characteristic odor of garlic on the breath. At the end of the 1930s, IG Farbenindustrie and the Shell Development Co. developed the high-temperature chlorination of propene, permitting large-scale production of allyl chloride with good yields. A significant part of the development was done by the Shell Chemical Co. when erecting a commercial plant in 1945. Dow, Solvay, and Asahi-Kashima developed their own processes.
Reactivity Profile
1.Reactions of the Double Bond
The reaction of allyl chloride with oxygen in the liquid phase at ca. 120 ℃ and in the presence of metal acetates or hydrogen peroxide yields glycerol monochlorohydrin. Halogens add readily to the double bond yielding the corresponding trihalogeno compounds. The reaction with hypochlorous acid, yielding 2,3- and 1,3-glycerol dichlorohydrins (which are then dehydrochlorinated with alkali to give epichlorohydrin), is of great industrial importance. Allyl chloride reacts with hydrogen halides to form 1,2-dihalogeno compounds. In the presence of peroxides, the reaction with hydrobromic acid yields 1-bromo-3chloropropane (Kharasch effect), but in highly concentrated hydrogen peroxide solution, 1,2-dibromo- 3-chloropropane is formed. Addition reactions of silanes, boranes, carboranes, and phosphorus trichloride, as well as cycloadditions of allyl cations with alkenes, are known. Allyl chloride polymerizes with sulfur dioxide to form polysulfones.
2.Reactions of the Chlorine Atom
Recently, Allyl alcohol is produced increasingly by the isomerization of propene oxide. The chlorine atom is replaced easily by iodide, cyanide, isothiocyanate, sulfide, polysulfides (giving rubber-like condensation products), and alkyl thiols. The salts of carboxylic acids yield allyl esters (e.g., diallyl phthalate), which are easily polymerized to allyl resins or are copolymerized with other monomers. Sodium allyl sulfonate is obtained on reaction with sodium sulfite. The reaction of allyl chloride with ammonia yields a mixture of mono-, di-, and triallylamines, and the reaction with primary and secondary amines makes the corresponding alkylallylamines. Phase-transfer-catalyzed carbonylation (e.g., with Ni(CO)4 or (Me4N)2 [Ni6(CO)12]) in the presence of sodium hydroxide leads to the sodium salt of vinylacetic acid. In the presence of alkalis, allyl chloride reacts with polyols to form the corresponding allyl ethers.
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).
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).
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
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
Toxicology
Acute and Subacute Toxicity: LD50=460 mg/kg (rat, oral); LD50= 3.7 mg/kg (rabbit, percutaneous); LC50= 11 mg/L (rat, inhalation, 2 h). The inhalation of 3 ppm allyl chloride during 7 h/d on 5 days a week was tolerated by a group of rats, guinea pigs, and rabbits for 180 days without irreversible damage occurring. An analogous test using 8 ppm over a period of 35 days led to damage of the liver and kidneys. Further experiments demonstrate a neurotoxic effect of allyl chloride, in particular to the peripheral nerves of cats and rabbits.
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).
storage
Pure, dry allyl chloride (water content2 200 mg/kg) does not corrode iron and can be stored in ferrous containers for months at ambient temperatures without significant changes in quality. Lined vessels should be used if traces of iron chlorides are objectionable. Unwanted coloration can be prevented by the addition of a suitable stabilizer (e.g., propene oxide).
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
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| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Svak Life Sciences | +91-9963463333 +91-9705383777 | Hyderabad, India | 101 | 58 | Inquiry |
| Vijaya Pharma And Life Science | +91-8939866271 +91-8939866271 | Tamil Nadu, India | 320 | 58 | Inquiry |
| Dr Prem's Molecules Pvt. Ltd. | +91 9825310038 | New Delhi, India | 547 | 50 | Inquiry |
| Scientific OEM | +91-22- 2343 7546 / 2341 3094 | New Delhi, India | 1996 | 38 | Inquiry |
| ALPHA CHEMIKA | +91-22-22061123 +91-22-66382501 | Mumbai, India | 1681 | 43 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Otto Chemie Pvt. Ltd. | +91 9820041841 | Mumbai, India | 5873 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| JSK Chemicals | 58 |
| Svak Life Sciences | 58 |
| Vijaya Pharma And Life Science | 58 |
| Dr Prem's Molecules Pvt. Ltd. | 50 |
| Scientific OEM | 38 |
| ALPHA CHEMIKA | 43 |
| CLEARSYNTH LABS LTD. | 58 |
| TCI Chemicals (India) Pvt. Ltd. | 58 |
| Otto Chemie Pvt. Ltd. | 58 |
| Alfa Aesar | 58 |
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