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Allyl chloride, also known as 3-chloropropene, is an organic compound with the chemical formula of C3H5Cl. It is a colorless transparent liquid, insoluble in water, and miscible in most organic solvents such as ethanol, ether, chloroform, petroleum ether, etc. It is mainly used as an intermediate in the production of epichlorohydrin, allyl alcohol, glycerin, etc., as a solvent for special reactions, and as a raw material for pesticides, medicines, spices, and coatings.
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Chemical Formula |
C3H5Cl |
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Exact Mass |
76 |
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Molecular Weight |
77 |
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m/z |
76 (100.0%), 78 (32.0%), 77 (3.2%), 79 (1.0%) |
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Elemental Analysis |
C, 47.09; H, 6.59; Cl, 46.33 |
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3-chloropropene (also known as allyl chloride, chemical formula C ∝ H ₅ Cl) is an important organic intermediate, which contains both unsaturated double bonds and active chlorine atoms in its molecular structure. It has high chemical reactivity and can undergo various reactions such as addition, substitution, and polymerization.
Core position: About 90% of 3-chloropropene is used for the synthesis of Epichlorohydrin, which is its largest consumer area.
Reaction pathway: Allyl alcohol is generated through hydrolysis reaction, followed by dichloropropyl alcohol under the action of chlorine gas, and finally epichlorohydrin is generated through cyclization reaction.
Downstream applications: Epichlorohydrin is a key raw material for producing epoxy resin, which is widely used in coatings, adhesives, electronic packaging materials, and other fields; Meanwhile, epichlorohydrin is also an important intermediate for the synthesis of glycerol, which has a huge demand in industries such as food, medicine, and cosmetics.
Pharmaceutical intermediates
Antibiotics and Vitamin Synthesis:
It is an intermediate for synthesizing vitamin A and provides key raw materials for industrial production.
Its derivatives can be used to synthesize antibiotics (such as tetracyclines) and other drugs, such as producing allyl alcohol through hydrolysis reactions, and further synthesizing anti-tumor drug intermediates.
Research and development of bioactive molecules:
The chlorine atom and double bond structure of 3-chloropropene make it a potential drug molecular skeleton, which can be used to design novel anti-inflammatory and antibacterial drugs.
Synthesis of insecticides:
Insecticidal single/insecticidal double/fenitrothion: used for synthesizing intermediate N, N-dimethylacrylamine, further producing sandworm toxin insecticides (such as insecticidal single, insecticidal double), which have the characteristics of high efficiency, low toxicity, and broad-spectrum against pests such as rice borers.
Pyrethroid intermediate: It can be used to synthesize acrylic ketone as a raw material for pyrethroid insecticides, and is used in the production of products such as cypermethrin and bromopyrethroids.
Synthesis of fungicides:
Used for synthesizing fungicides such as allyl thiazole, it has a preventive effect on diseases such as rice sheath blight and wheat powdery mildew.
Spices and surfactants
Spice synthesis:
Acrolein is generated through oxidation reaction, and flavor intermediates (such as citral and citronellal) are further synthesized for the preparation of daily chemical essence and food essence.
Surfactant:
Reacts with long-chain alkyl primary amines to generate alkyl allyl ammonium chloride, which is used as a cationic surfactant in fields such as textile softeners and hair conditioners.
Rubber modification:
It can be used as a comonomer to copolymerize with other monomers (such as butadiene and styrene) to prepare rubber with chlorinated propylene structure. This type of rubber has excellent oil resistance, heat resistance, and aging resistance, and is widely used in fields such as automotive seals and industrial hoses.
Functional polymer materials:
Ion exchange resin: copolymerized with divinylbenzene and introduced with sulfonic acid groups to prepare strong acidic cation exchange resin for water treatment and chemical separation (such as metal ion recovery).
Soil amendment: By polymerization reaction, polyacrylamide substances are generated to improve soil structure and enhance water and fertilizer retention capacity.
Coatings and adhesives
Paint raw materials:
Used for synthesizing acrylic monomers (such as 3-chloro-2-hydroxypropyl acrylate) as modifiers for coating resins to enhance the chemical resistance and adhesion of coatings.
Adhesive:
As an active diluent for epoxy resin adhesives, it reduces system viscosity and improves construction performance; Simultaneously participating in the curing reaction to improve the strength of the adhesive layer.
lubricant:
Reacts with fatty acids to produce allyl fatty acids, which are used as lubricant additives to enhance lubrication performance and wear resistance.
Plasticizer:
Used for synthesizing diallyl phthalate (DAP) as a plasticizer for polyvinyl chloride (PVC), endowing the material with flexibility and aging resistance.
Other applications
Solvent and extractant:
3-chloropropene has selective solubility in certain organic compounds and can be used as a solvent or extractant for special reactions.
Soil improvement:
Polyacrylamide is generated through polymerization reaction for soil solidification and prevention of soil erosion.
Preparation of 3-chloropropene:
The synthesis process of allyl chloride is relatively mature, and the synthesis methods mainly include high-temperature chlorination, propylene oxychlorination, allyl alcohol chlorination, etc.
High temperature chlorination method:
Propylene and chlorine are chlorinated at high temperature; the process is as follows; dry propylene (fresh propylene: circulating propylene = 1:3) is preheated to 350-400°C in heating, and mixed with chlorine gas at the entrance of the reaction tower ( Chlorine: propylene = 1:3), sprayed into the furnace through a special nozzle, the temperature in the furnace is about 500 ℃, and the propylene is preheated with the heat of chlorination reaction.
The single-pass conversion rate of propylene is 25%, the conversion of chlorine is stoichiometric, and the total yield of it is 80-85%. In addition to the main product chloropropene, there are also 1,2-dichloropropene, 1,3 -Dichloropropene, hydrogen chloride, 1,2,3-trichloropropane and other minor by-products. The chlorination reactant is cooled rapidly to 50-100°C to remove hydrogen chloride and propylene, and then fractionated to obtain 3-chloropropene. For an annual output of 13,500 tons of propylene chloride, the consumption of propylene per ton is about 700kg and chlorine gas is 1120kg.
Oxychlorination method:
Propylene is used as raw material and tellurium is used as catalyst to obtain propene chloride through the following reaction; propene, hydrochloric acid and oxygen are mixed according to the ratio of 2.5-1:1:1-0.2 (molar ratio). The reaction was carried out at 240°C and 0.101MPa. The reactor is a fluidized bed, the catalyst is TeV2O5H3PO4 loaded on the carrier, and nitrogen-containing substances are added as a promoter, the selectivity is over 90%, and the space-time yield of the fluidized bed is greater than 100g product/L catalyst hour .
Allyl chloride method:
Add sulfuric acid dropwise to allyl alcohol, cuprous chloride and hydrochloric acid at 10-20°C. After the dropwise addition, keep it warm for 5 hours, let it stand for stratification, and wash the upper layer with water, 5% sodium carbonate solution and water once respectively. After separating the water, distill and collect the fraction above 40°C, which is 3-chloropropene. This method is suitable for small batch production, and the yield is 73%.
A method for preparing 3-chloropropene by catalytic oxidation of 1,2-dichloropropane :
The method for preparing 3-chloropropene by catalytic oxidation of 1,2-dichloropropane is characterized in that: the metal carbonyl catalyst is placed in a fixed-bed reactor, nitrogen gas is passed through, and 1,2-dichloropropane is passed through after heating up to carry out Dehydrochlorination reaction, the reaction product is collected to generate 3-chloropropene; the reaction product is washed with water, alkali neutralized, and washed, then sent to the propylene compressor, cooled to become liquid, then passed through the cooler, and then dried by the propylene drying tower, and then After fractionation and rectification, the obtained recombination is divided into products.
The method finds a way for a large number of applications of the industrial by-product 1,2-dichloropropane, reduces the production cost of 3-chloropropene, not only increases the economic benefits of the enterprise, but also solves the problem of disposal of toxic industrial by-products, and has obvious environmental protection benefits.
FAQ
What is allyl chloride used for?
Allyl chloride is primarily used in the manufacture of epichlorohydrin and glycerin pesticides, epoxy resins, monomers of polyacrylonitrile, and allyl compounds such as sodium allyl sulfonate. The threshold limit value in the United States is 1 ppm. Allyl chloride may be absorbed via the oral or inhalation route.
What is vinyl chloride and allyl chloride?
C H 2 = CH - Cl and C H 2 = CH - C H 2 - Cl respectively. - As we can see that in vinyl chloride the chlorine atom which is attached to the carbon is s p 2 hybridised whereas, in allyl chloride, the chlorine atom which is attached to the carbon is s p 3 hybridised.
What are the health effects of allyl chloride?
Chronic (long-term) exposure to allyl chloride in humans causes injury to the liver and kidneys and the onset of pulmonary edema (fluid in the lungs). There are no human cancer data available for allyl chloride.
How is allyl chloride made?
In a catalytic oxychlorination process, allyl chloride is prepared by the reaction of oxygen and hydrogen chloride with propylene in the presence of an oxychlorination catalyst at a temperature effective to produce allyl chloride. Suitable catalysts are described in U.S. Pat.
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