107-05-1 Usage
Chemical Description
Allyl chloride is an organic compound with the formula CH2=CHCH2Cl, which is used in the production of various chemicals.
Chemical Properties
Different sources of media describe the Chemical Properties of 107-05-1 differently. You can refer to the following data:
1. colourless, light yellow or amber liquid with an unpleasant smell
2. 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.
3. 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
Different sources of media describe the Uses of 107-05-1 differently. You can refer to the following data:
1. 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).
2. Allyl chloride is used in the synthesis of glycerol, allyl alcohol and epichlorohydrin.
3. 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).
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
Different sources of media describe the Health Hazard of 107-05-1 differently. You can refer to the following data:
1. Causes marked irritation of skin and may burn. Burns the eyes; effect may be delayed.
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 107-05-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 107-05:
(5*1)+(4*0)+(3*7)+(2*0)+(1*5)=31
31 % 10 = 1
So 107-05-1 is a valid CAS Registry Number.
107-05-1Relevant articles and documents
Sharman et al.
, p. 5965,5971 (1958)
Collisional Energy Transfer in Thermal Decomposition Reaction of 1,2-Dichloropropane
Yun, Sun Jin,Jung, Kyung-Hoon,Kang, Wee-Kyeong
, p. 5842 - 5847 (1988)
The thermal decomposition reaction of 1,2-dichloropropane (1,2-DCP) was studied at temperatures from 663.2 to 703.2 K over the pressure range 0.04-10.0 Torr.The decomposition modes of 1,2-DCP were monitored via four reaction channels of unimolecular HCl eliminations and a negligible portion of a side radical chain reaction. 3-Chloropropene (3-CP), cis-1-chloropropene (cis-1-CP), trans-1-chloropropene (trans-1-CP), and 2-chloropropene (2-CP) were produced.Rate parameters for the thermal processes found in this study are k3(3-CP)/s-1=1013.61 +/- 0.30exp-1/RT>, kcis(cis-1-CP)/s-1=1012.90 +/- 0.70exp-1/RT>, ktrans(trans-1-CP)/s-1=1013.21 +/- 0.80exp-1/RT>, k2(2-CP)/s-1=1013.05 +/- 0.44exp-1/RT>, and ktot(total)/s-1=1013.70 +/- 0.50exp-1/RT>.The unimolecular thermal decomposition reactions of the four-channel 1,2-DCP system were carried out in the presence of a He bath gas to evaluate intermolecular-energy-transfer parameters.The average energies removed per collision from energized 1,2-DCP by bath gas are as follows: by the substrate, 1200 cm-1 for the stepladder model; by He, 250 cm-1 for the exponential model.The effects of active additives, CO2 and HCl, and the surface condition of the reaction vessel were also studied to ascertain the potential properties of the thermal decomposition reaction of 1,2-DCP.
Pressure dependence of the reaction Cl + C3H6
Kaiser,Wallington
, p. 9788 - 9793 (1996)
The rate constant for the reaction Cl + C3H6 (k1) has been measured relative to that of Cl + C2H6 over the range 0.3-700 Torr in N2 at 298 K. UV irradiation was used to generate Cl atoms in mixtures of C3H6, C2H6, Cl2, and N2 in two different reactors using FTIR or GC analysis. The yields of the two major products, allyl chloride (3-C3H5Cl) and 1,2-dichloropropane were measured. k1 decreases by a factor of 5 between 700 and 1 Torr. Below 1 Torr, the rate constant becomes independent of pressure. The results indicate that k1 is a composite of three reaction channels, each having a different pressure dependence. Measurement of the yield of 1,2-dichloropropane, the final product formed from the addition of Cl to C3H6, at each pressure allows a determination of the rate constant (k1a) for the addition of Cl to C3H6. Assuming a typical center broadening factor (Fc = 0.6), the high- and low-pressure limiting constants are calculated to be k1a(∞) = (2.7 ± 0.4) × 10-10 cm3 molecule-1 s-1 and k1a(0) = (4.0 ± 0.4) × 10-28 cm6 molecule-2 s-1. The pressure dependence of the yield of 3-C3H5Cl indicates that the allyl radical is likely formed by both abstraction and addition-elimination channels. The rate constant of the abstraction reaction from the methyl radical in C3H6 is (2.3 ± 0.3) × 10-11 cm3 molecule-1 s-1. At pressures below 10 Torr, the rate constant for formation of the allyl radical increases by 50%, and this is ascribed to an addition-elimination process. Relative rate constant ratios were also measured for Cl atom reactions with allyl chloride (k6) and 1,2-dichloropropane (k7) relative to C3H6, C2H5Cl, or CH3Cl to correct the product yield experiments for secondary consumption. The observed values of k6/k1 are 0.75 for total pressures of 10-700 Torr, 0.44 at 1 Torr, and 0.33 at 0.4 Torr. On the basis of the relative rate measurements k7 = (3.9 ± 0.6) × 10-12 cm3 molecule-1 s-1 over the range 1-700 Torr.
KrF Excimer Laser-induced Dehydrochlorination of 1,2-Dichloropropane
Ouchi, Akihiko,Niino, Hiroyuki,Yabe, Akira,Kawakami, Haruhiko
, p. 917 - 920 (1988)
Dehydrochlorination of 1,2-dichloropropane was conducted with and without irradiation of KrF excimer laser (248 nm).It afforded four products, cis-1-, trans-1-, 2-, and 3-chloropropene.The reaction was remarkably accelerated with irradiation of laser especially at the low temperatures.
Preperation and Properties of Inclusion Compounds of η3-Allylpalladium Complexes with Cyclodextrins
Harada, Akira,Takeuchi, Mizutomo,Takahashi, Shigetoshi
, p. 4367 - 4370 (1988)
Inclusion compounds of di-μ-chloro-bis(η-allyl)dipalladium and its analogues with cyclodextrins (CDs; α-CD, β-CD, and γ-CD) were prepared.One-to-one inclusion compounds were obtained in high yields by the treatment of β- and γ-cyclodextrin with di-μ-chlor
Silphos [PCl3-n(SiO2)n]: A heterogeneous phosphine reagent for the conversion of epoxides to β-bromoformates or alkenes
Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
, p. 1823 - 1827 (2006)
Silphos [PCl3-n(SiO2)n] as a heterogeneous phosphine reagent is efficiently applied for the transformation of epoxides to β-bromoformates in the presence of bromine or N-bromosuccinimide in dimethyl formamide at 0 °C. The combination of Silphos and iodine was also found suitable for the room temperature preparation of alkenes. The use of Silphos provides the advantage of easy separation of the phosphine oxide by-product from the reaction mixture.
Method for preparing 2-chloro-5-substituted pyridine
-
Paragraph 0061-0064; 0065-0067, (2021/09/21)
The invention belongs to the technical field of chemical synthesis of pesticides, and particularly relates to a method for preparing 2-chloro-5-substituted pyridine, in particular to a method for preparing 2-chloro-5-methylpyridine. The method comprises the following steps: reacting amide as shown in a formula C which is used as a raw material in the presence of a chlorinating agent and N, N-dimethylformamide, and distilling after the reaction is finished to obtain the 5-substituted 2-chloropyridine as shown in a formula I which is described in the specification. When the 5-substituted 2-chloropyridine is prepared from the compound with the structure shown in the formula C, the by-product is allyl chloride (or homologues thereof) with small molecular weight, the boiling point of the by-product is obviously different from that of the product, the reaction conversion rate and the yield are higher than those of the prior art, the by-product is easy to separate from the product, and the by-product is more beneficial to recovery; therefore, according to the preparation method, the equipment investment can be greatly saved, the production cost is reduced, and the operation procedure is simplified; and in the route, the amine with lower price is used as a starting raw material, so that the production cost is reduced.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Piperazine-promoted gold-catalyzed hydrogenation: The influence of capping ligands
Barbosa, Eduardo C. M.,Camargo, Pedro H. C.,Fiorio, Jhonatan L.,Hashmi, A. Stephen K.,Kikuchi, Danielle K.,Rossi, Liane M.,Rudolph, Matthias
, p. 1996 - 2003 (2020/04/22)
Gold nanoparticles (NPs) combined with Lewis bases, such as piperazine, were found to perform selective hydrogenation reactions via the heterolytic cleavage of H2. Since gold nanoparticles can be prepared by many different methodologies and using different capping ligands, in this study, we investigated the influence of capping ligands adsorbed on gold surfaces on the formation of the gold-ligand interface. Citrate (Citr), poly(vinyl alcohol) (PVA), polyvinylpyrrolidone (PVP), and oleylamine (Oley)-stabilized Au NPs were not activated by piperazine for the hydrogenation of alkynes, but the catalytic activity was greatly enhanced after removing the capping ligands from the gold surface by calcination at 400 °C and the subsequent adsorption of piperazine. Therefore, the capping ligand can limit the catalytic activity if not carefully removed, demonstrating the need of a cleaner surface for a ligand-metal cooperative effect in the activation of H2 for selective semihydrogenation of various alkynes under mild reaction conditions.
