Storage and transportation
Ventilation, low temperature and drying; keeping away from oxidants, acids stored; deterioration after a long period
manufacture of colloidal forms of metals; making plastics, perfumes; warning agent in methyl chloride refrigerant. Has been used in military poison gas mixtures. Used in organic syntheses. Aquatic herbicide.
Air & Water Reactions
Highly flammable. A dangerous fire risk [Hawley]. Water soluble. Reacts slowly and exothermically with water to give 3-hydroxypropionaldehyde. A hazard can develop from this reaction if acrolein is stored over a layer of water.
Acrolein is colorless, transparent, flammable volatile and volatile liquid, with a strong irritation and the steam has a strong tearing property.
It is soluble in 2 to 3 times of the water, soluble in alcohol, ether and acetone.
Flammability hazard characteristics
Inflammable in the presence of fire, high temperature and oxidant; stimulating smoke when in combustion
Explosives hazardous characteristics
Explosive when mix with air
Under fire conditions, polymerization may occur. If inside a container, violent rupture of the container may take place. When heated to decomposition, Acrolein emits highly toxic fumes. Alkalis or strong acids act as catalysts, causing a condensation reaction and liberating energy. Reaction may be very rapid and violent. Readily converted by oxygen to hazardous peroxides and acids. Unstable, avoid exposure to alkalis, strong acids, oxygen, elevated temperatures, such as fire conditions. (Polymerization inside container could cause violent rupture of container under fire conditions.)
Purify acrolein by fractional distillation, under nitrogen, drying with anhydrous CaSO4 and then distilling under vacuum. Blacet, Young and Roof [J Am Chem Soc 59 608 1937] distilled it under nitrogen through a 90cm column packed with glass rings. To avoid formation of diacryl, the vapour is passed through an ice-cooled condenser into a receiver cooled in an ice-salt mixture and containing 0.5g catechol. The acrolein is then distilled twice from anhydrous CuSO4 at low pressure, catechol being placed in the distilling flask and the receiver to avoid polymerization. [Alternatively, hydroquinone (1% of the final solution) can be used.] [Beilstein 1 IV 3435.]
TWA 0.25 mg/m3; STEL 0.75 mg/m3
1. Propylene catalytic air oxidation method: the bismuth molybdate and bismuth phosphomolybdate catalyst of propylene is directly oxidated in the presence of air at the reaction temperature of 310-470 ° C, atmospheric pressure. The product is acquired when the acid of the by-product is removed from the product in the reaction, and then distillation. 2. Glycerol dehydration method: Glycerol and potassium bisulfate or potassium sulfate, boric acid, aluminum chlorides are under heat at 215-235 ° C in the system. 3. Formaldehyde-acetaldehyde method: under the catalysis of silica gel which is impregnated in sodium silicate, it is produced by gas-phase condensation of formaldehyde and acetaldehyde in the system.
Laboratory method: Heat glycerol and potassium bisulfate or magnesium sulfate, boric acid, aluminum oxide together at 215~235 ° C. Distil off and condensate acrolein gas in the reaction, thus generating the crude. 10% sodium hydrogen phosphate solution were added to the crude to adjust the pH value to 6. Through fractionation, collecting 50~75 ℃ distillate, pure acrolein was abtained.
Feed ratio (mol): glycerol: potassium hydrogen sulfate: potassium sulfate = 1 ︰ 0.5: 0.026.
Industrial production method: at present, the main industrial method is propylene catalytic air oxidation method.
The mixture of propylene, air and steam in a certain proportion is mixed with catalyst and sent to a fixed bed reactor. The reaction is carried out at 0.1~0.2 MPa and 350~450 ℃ for 0.8 s. The heat released from the reaction is recovered by steam produce. The resulting gaseous mixture is quenched with water and the exhaust gas from the quench tower is washed before being vented. The organic liquid coming out of the bottom of the quench tower is stripped of the stripper to vaporize the acrolein and other light components and then to remove water and acetaldehyde from the crude acrolein by distillation.
Feed ratio (mol) Propylene: Air: Water vapor = 1: 10: 2.
ACROLEIN, [INHIBITED] can react violently with oxidizing agents. Polymerizes exothermically on contact with small amounts of acids (including sulfur dioxide), alkalis, volatile amines and pyridines, salts, thiourea, oxidizing agents (air) and on exposure to light and heat. Polymerization initiated by amines and pyridines occurs after a deceptive induction period. Water solutions of mineral acids and metal ions can initiate polymerization. The inhibitor (usually hydroquinone) greatly reduces tendency to polymerize. Undergoes Diels-Alder reaction with itself to give acrolein dimer. This can become a runaway reaction at 90°C [Kirk-Othmer, 4th Ed, Vol. 1]. Mixing in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: 2-aminoethanol, ammonium hydroxide, chlorosulfonic acid, ethylenediamine, ethyleneimine [NFPA 1991].
Dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent
It is used as oil field water injection fungicide, to inhibit the growth of bacteria in the water injection, to prevent bacteria in the formation of corrosion and blockage and other issues in overseas. Acrolein is an important organic synthesis intermediates which can be used in the manufacture of methionine (feed additives). Allyl alcohol derived from the reduction of acrolein can be used as raw materials for the production of glycerol; by oxidation, acrylic acid can be obtained to further prepare acrylic ester for acrylate coating. Acrolein dimer can be used to produce dialdehyde compounds, widely used in paper, tanning and textile auxiliaries. Acrolein is raw materials for glutaraldehyde, 1,2,6-hexanetriol crosslinking agents.It is also used for the production of colloidal osmium, ruthenium, rhodium. The reaction between acrolein and bromine can obtain 2,3-dibromopropanal. 2.3-dibromopropanal is a pharmaceutical intermediates, used to produce anti-tumor drugs such as methotrexate. As a standard substance for chromatographic analysis, also used in organic synthesis. For the synthetic resin industry, one of the important raw materials, but also for a large number of organic synthesis and drug synthesis.
This product can be used to produce methionine and other acrolein derivatives in the manufacture of methionine (feed additives); allyl alcohol derived from the reduction of acrolein can be used as raw materials for the production of glycerol; by oxidation, acrylic acid can be obtained to further prepare acrylic ester for acrylate coating; Acrolein is raw materials for glutaraldehyde, 1, 2, 6-hexanetriol crosslinking agents. It is also used for the production of colloidal osmium, ruthenium and rhodium. The reaction between acrolein and bromine can obtain 2,3-dibromopropanal. 2.3-dibromopropanal is a pharmaceutical intermediates, used to produce anti-tumor drugs such as methotrexate. Acrolein is a very important intermediate for the production of imidacloprid, a biological pesticide.
Oral-Rat LD50: 46 mg/kg; Oral-mouse LD50: 40 mg/kg
Acrolein is a kind of irritant aldehyde compound. It is colorless to yellowish transparent liquid at normal temperature. It has the similar odor of charred oil, soluble in water, ethanol, ether, paraffin (n-hexane, N-octane, cyclopentane), toluene, xylene, chloroform, methanol, ethylether, acetaldehyde, acetone, acetic acid, acrylic acid and ethyl acetate. Acrolein easily polymerized into two polyacrolein; turned into a translucent solid in the light irradiation and generated acrylic acid when in oxidation. 0.2% hydroquinone can be added as a stabilizer when in storage. It is used in the manufacture of resins, pharmaceuticals, glycerol, methionine-alike (auxiliary feed) and so on. It is the more common pollutants in the environment. Acute exposure will damage the respiratory tract, eye and skin, and cause lung and tracheal edema, but also lead to abnormal fat metabolism in the human body, resulting in a lot of fat accumulation in the subcutaneous tissue. Subchronic and chronic exposure has caused monkeys, dogs and other experimental animals, tracheal and nasal cytoplasmic hyperplasia, but no carcinogenic phenomenon. Acute and chronic poisoning concentrations in freshwater were 68 μg/L and 21 μg/L, respectively. The intolerant concentration was 10 mg/m3. During the First World War the French army has used it to make chemical grenades.
Acrolein and nicotine, carbon monoxide in cigarettes are the three major harmful ingredients, which can lead to gene mutation, and reduce the ability of cell-repair damage, and they are major factors to the damage of the retina. In cigarettes, the content of acrolein is 10,000 times higher than the carcinogenic substances of polycyclic aromatic hydrocarbons. As a tar component, acrolein toxicity is also thousands of times higher than formaldehyde, and the boiling point is of only 50 degrees Celsius. Cigarettes will immediately gasify when be ignited, invading the retinal pigment epithelium, causing its oxidative damage and preventing the intracellular "energy plant" mitochondria from producing energy. This epithelium is responsible for a variety of nutrients on the retina and waste metabolism. If they "strike", a number of eye cells die.
"Air Quality Assessment Guidelines for Passenger Cars" clearly stipulates the concentration of volatile organic compounds (VOCs) in the air of the vehicle, such as benzene, toluene, xylene, ethylbenzene, styrene, formaldehyde, acetaldehyde and acrolein. Limits. Benzene ≤ 0.11mg/m3, toluene ≤ 1.10mg/m3, xylene ≤ 1.50mg/m3, ethylbenzene ≤ 1.50mg/m3, styrene ≤ 0.26mg/m3, formaldehyde ≤ 0.10mg/m3, acetaldehyde ≤ 0.05 Mg/m3, acrolein ≤ 0.055 mg/m3. These standards apply not only to new cars, but also to vehicles.
Extremely toxic; probable oral human lethal dose is 5-50 mg/kg, between 7 drops and one teaspoon for a 70 kg (150 lb.) person. Inhalation of air containing 10 ppm of acrolein may be fatal in a few minutes. Death from cardiac failure accompanied by hyperemia and hemorrhage of the lungs and degeneration of the bronchial epithelium is possible. Acrolein causes acute respiratory and eye irritation; severe gastrointestinal distress with slowly developing pulmonary edema (lungs fill up with fluid); and skin irritation.
Acrolein is used in the synthesis of acrylic acid.
Eye-Rabbit 1 mg Severe; Skin-Rabbit 5 mg Severity
colourless to slightly yellow liquid