3-chloropropene (allyl chloride)

3-chloropropene (allyl chloride) - Names and Identifiers

Name	Allyl chloride
Synonyms	3-Chloroprene Allyl chloride 3-chloro-propen 3-chloro-1-propen 3-Chloro-1-propene 2-propenylchloride 3-chloroprop-1-ene 3-chloro-prop-1-ene 3-Chloro-1-propylene 3-chloropropene(allylchloride) 3-chloropropene (allyl chloride)
CAS	107-05-1
EINECS	203-457-6

3-chloropropene (allyl chloride) - Physico-chemical Properties

Molecular Formula	C3H5Cl
Molar Mass	76.52
Density	0.939g/mLat 25°C(lit.)
Melting Point	-136 °C
Boling Point	44-46°C(lit.)
Flash Point	−20°F
Water Solubility	3.6 G/L (20 ºC)
Solubility	alcohol: miscible(lit.)
Vapor Presure	20.58 psi ( 55 °C)
Vapor Density	2.6 (vs air)
Appearance	Powder/Solid
Specific Gravity	0.939
Color	White
Odor	pungent odor
Exposure Limit	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.
Merck	14,289
BRN	635704
Storage Condition	Store at +2°C to +8°C.
Stability	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 alum
Explosive Limit	3.3-11.2%(V)
Refractive Index	n20/D 1.414(lit.)
Physical and Chemical Properties	Properties of colorless flammable liquid, corrosive and irritating smell. boiling point 45 ℃ freezing point -134.5 ℃ relative density 0.9382 refractive index 1.4160 flash point -31.7 ℃ solubility slightly soluble in water, miscible with ethanol, chloroform, ether and petroleum ether.
Use	Used in organic synthesis, pesticides, coatings, synthetic resins, but also used as adhesives, lubricants, etc

3-chloropropene (allyl chloride) - Risk and Safety

Risk Codes	R45 - May cause cancer R46 - May cause heritable genetic damage R11 - Highly Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. R48/20 - R50 - Very Toxic to aquatic organisms R68 - Possible risk of irreversible effects R40 - Limited evidence of a carcinogenic effect R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R48/23/24/25 -
Safety Description	S53 - Avoid exposure - obtain special instructions before use. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S46 - If swallowed, seek medical advice immediately and show this container or label. S25 - Avoid contact with eyes. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed.
UN IDs	UN 1100 3/PG 1
WGK Germany	2
RTECS	UC7350000
FLUKA BRAND F CODES	19
TSCA	Yes
HS Code	2903 29 00
Hazard Note	Flammable
Hazard Class	3
Packing Group	I
Toxicity	LD50 orally in rats: 0.7 g/kg (Smyth, Carpenter)

3-chloropropene (allyl chloride) - Nature

Open Data Verified Data

colorless flammable liquid, corrosive and irritating odor. Relative density (d20) 0.9382. Freezing point -134.5 °c. Boiling point 45. Refractive index 4160. Viscosity (20 C) 0.336MPA-s. Specific heat capacity (30 degrees C) 1.633 J/(g. C). Flash point (closed Cup)- 31.7 °c. Vapor pressure (20 °c) 39. 396 kPa. Spontaneous ignition point 392. Can occur oxidation, addition, polymerization, hydrolysis, ammoniation, cyanation, esterification and other reactions. Slightly soluble in water, and ethanol, chloroform, ether and petroleum ether miscible. Toxic!

Last Update：2024-01-02 23:10:35

3-chloropropene (allyl chloride) - Preparation Method

Open Data Verified Data

high temperature chlorination propylene is subjected to high temperature chlorination after preheating, and the crude product is obtained by condensation and distillation to obtain a finished product.
the oxychlorination method is prepared by a gas phase reaction of propylene, hydrogen chloride and oxygen in the presence of a tellurium catalyst.
allyl alcohol chloride method this method is suitable for small batch production.

Last Update：2022-01-01 10:15:06

3-chloropropene (allyl chloride) - Use

Open Data Verified Data

The production of glycerol, epichlorohydrin, allyl alcohol and other organic synthesis intermediates, but also pesticides, pharmaceutical raw materials. It can also be used as a raw material for synthetic resins, coatings, adhesives, plasticizers, stabilizers, surfactants, lubricants, Soil improvers and perfumes.

Last Update：2022-01-01 10:15:07

3-chloropropene (allyl chloride) - Safety

Open Data Verified Data

strong vapor irritation, weak anesthetic effect, strong eye, nose and throat stimulation. The damage to the liver is small, and the damage to the lung and kidney is large. Among the halogenated hydrocarbons, allyl chloride is a highly toxic substance. Rat oral LD50 0.7g/kg. Rats inhaled a concentration of 300 x 10-6 vapor and died within a few hours. In Guinea Pigs, the concentration of lO ~ lOOmg/L strongly stimulates the mucosa, and then invades the lung and causes death. Can be absorbed through the skin, if attached to the clothing must be replaced immediately. The operator should wear protective gear. The maximum allowable concentration in workplace air is 1 × 10-6 (3mg/m3).
can be shipped with iron drum and tank car. The storage tank should be stored in a cool and ventilated place. Fire prevention, Explosion Prevention, sun protection and leakage prevention. It can be transported by rail and road. The flammable and toxic substances shall be stored and transported according to the regulations.

Last Update：2022-01-01 10:15:07

3-chloropropene (allyl chloride) - Reference Information

freezing point	-134.5 ℃
Henry's Law Constant	2.69 at 25 °C (static headspace-GC, Welke et al., 1998)
LogP	2.1 at 25℃
NIST chemical information	information provided by: webbook.nist.gov (external link)
(IARC) carcinogen classification	3 (Vol. 36, Sup 7, 71, 125) In prep.
EPA chemical substance information	information provided by: ofmpeb.epa.gov (external link)
Introduction	allyl chloride, also known as allyl chloride, is a raw material for organic synthesis. The physical properties of allyl chloride are: colorless flammable liquid, corrosive and irritating smell. Slightly soluble in water, and ethanol, chloroform, ether and petroleum ether miscible. Its use: can be used as the production of epichlorohydrin, propylene alcohol, glycerol and other intermediates, used as a solvent for special reactions, but also pesticides, pharmaceuticals, spices, coatings of raw materials.
Use	can be used as an intermediate in the production of epichlorohydrin, allyl alcohol, glycerol, etc., as a solvent for special reactions, as well as pesticides, raw materials of medicine, perfume, coating used in organic synthesis and pharmaceutical industry 3-chloropropene, also known as allyl chloride, is a kind of organic synthesis raw materials, used in the synthesis of pesticides, the intermediate N,N-dimethylpropenamine and the intermediate of pyrethroid, Acryl ketone, are also important raw materials for medicine, synthetic resin, coating and perfume. The product has the reactivity of olefin and halogenated hydrocarbon, and is an organic synthesis intermediate of glycerol, epichlorohydrin, allyl alcohol, etc. Also used for pesticides, pharmaceutical raw materials. Can also be used as synthetic resins, coatings, binders, plasticizers, stabilizers, surfactants, lubricants, soil conditioners, spices and other fine chemicals raw materials, mainly used in the manufacture of epichlorohydrin, glycerol, chloropropanol, allyl alcohol, pesticide insecticidal double, medicine, resin, coating, adhesive, and sodium acrylate, lubricant, etc. used in organic synthesis, pesticides, coatings, synthetic resins, also used as adhesives, lubricants, etc. Because of its active chemical properties, it is an important intermediate in organic synthesis, in addition to the production of epichlorohydrin, glycerol raw materials, can also be used as raw materials for the synthesis of allyl alcohol, pharmaceuticals, dyes, pesticides and synthetic resins.
production method	1. High temperature chlorination propylene and chlorine are subjected to chlorination at high temperature; The process is as follows; Dried propylene (fresh propylene: recycled propylene = 1:3) is preheated to 350-400 °c with heating, at the inlet of the reaction column, it is mixed with chlorine gas (chlorine gas: Propylene = 1:3), and sprayed into the furnace through a special nozzle. The temperature in the furnace is about 500 ° C., and propylene is preheated by chlorination reaction heat. The conversion of propylene per pass is 25%, the conversion of chlorine into stoichiometric amount, the total yield of allyl chloride is 80-85%, in addition to the main product Allyl, there are 1, 2-dichloropropene, 1, 3-dichloropropene, hydrogen chloride, 1,2, 3-trichloropropane and other minor by-products. The chlorination reaction was quenched to 50-100 °c to remove hydrogen chloride and propylene and fractionated to yield propylene chloride. For an annual output of 1. For the 350,000 t allyl chloride plant, about 700kg of propylene and 1120kg of chlorine gas are consumed per ton of product. 2. Oxychlorination method allyl chloride was obtained by the following reaction using propylene as a raw material and tellurium as a catalyst; Propylene, hydrochloric acid and oxygen were mixed in a molar ratio of 2.5 to 1:1 to 0.2. The reaction was carried out at 240 °c, 0.101MPa. The reactor is a fluidized bed, the catalyst is Te V2 O5 H3 PO4 on a carrier, and a nitrogen-containing substance is added as a promoter. The selectivity is more than 90%, and the space-time yield of the fluidized bed is more than 100g of allyl chloride/L of catalyst. In small batch production, it can be obtained by chlorination of allyl alcohol; Sulfuric acid is added to allyl alcohol, cuprous chloride and hydrochloric acid at 10-20 °c. After addition, the reaction was incubated for 5H. The mixture of acid in the lower layer was separated and separated. The upper layer was washed with water once, 5% sodium carbonate solution once, and then washed with water once, allyl chloride was obtained. The yield was 73%. The preparation method includes a high-temperature chlorination method, a propylene oxychlorination method, an allyl alcohol chlorination method, and the like. The high temperature chlorination method is prepared by the high temperature of propylene. Reaction equation: CH3CH = CH2 + Cl2 → ClCH2CH = CH2 + HCl the dried propylene is preheated at 350~400 ℃, and the liquid chlorine is heated and gasified, the two materials are mixed and reacted under the condition of high-speed injection, the ratio of propylene to chlorine is 4~5 ∶ 1 (molar ratio), and the residence time of the reactor is 1.5~2s, the reaction temperature was 470 to 500 °c. The reaction product was quenched to 50-100 °c to remove HCl and propylene and fractionated to obtain the product. This method is used by most domestic and foreign production enterprises. Propylene oxychlorination process propylene, hydrogen chloride and oxygen mixed in a ratio of 2.5 to (1: 1: 1) to 0.2 (molar ratio) are reacted in a fluidized bed reactor, the catalyst is Te, V2O5 or H3PO4 supported on the carrier, and the nitrogen-containing substance is added as a promoter. The oxychlorination reaction is carried out at 240~260 ℃ under atmospheric pressure to prepare 3-chloropropene. Reaction equation: CH3CH = CH2 + HCl +1/2O2 [catalyst] → CH2 = CHCH2Cl + H2O allyl alcohol chlorination reaction equation: CH2 = CHCH2OH[Cu2Cl2,HCl]→ CH2 = CHCH2Cl + H2O sulfuric acid was dripped into allyl alcohol, cuprous chloride and hydrochloric acid at 10~20 ℃. After the dropwise addition was completed, the reaction was maintained for 5h, and the mixture was allowed to stand and layered, the 5% sodium carbonate solution and the water were washed once each, and after removing the water, the fraction above 40 ° C. Was collected by distillation, which was 3-chloropropene. This method is suitable for small batch production.
category	flammable liquid
toxicity grade	poisoning
Acute toxicity	oral-rat LD50: 1100 mg/kg; Oral-mouse LD50: 425 mg/kg
stimulation data	Skin-rabbit 10 mg/24 h; eye-rabbit 500 mg moderate
explosive hazard characteristics	explosive when mixed with air
flammability hazard characteristics	in case of open flame, high temperature, flammable oxidant; Toxic chloride smoke generated by combustion; thermal decomposition of toxic hydrogen chloride gas
storage and transportation characteristics	The warehouse is ventilated and dried at low temperature; It is stored separately from oxidants, acids and alkalis
extinguishing agent	dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent
Occupational Standard	TWA 1 PPM
spontaneous combustion temperature	390°C
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)
immediate life-and health-threatening concentration	250 ppm