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Acrolein

Basic information Aldehyde compound Chemical properties Uses Preparation Category Toxicity Acute toxicity Stimulation data Explosives hazardous characteristics Flammability hazard characteristics Storage and transportation Extinguishing agent Occupational Standard Safety Related Supplier
Acrolein Basic information
Acrolein Chemical Properties
  • Melting point:−87 °C(lit.)
  • Boiling point:53 °C(lit.)
  • Density 0.839 g/mL at 25 °C(lit.)
  • vapor density 1.94 (vs air)
  • vapor pressure 4.05 psi ( 20 °C)
  • refractive index n20/D 1.403(lit.)
  • Flash point:−2 °F
  • storage temp. 2-8°C
  • solubility H2O: soluble2 to 3 parts
  • form Liquid
  • OdorPungent, lacrimatory, intensely irritating odor detectable at 0.02 to 0.4 ppm
  • explosive limit31%
  • Water Solubility Soluble. 21.25 g/100 mL
  • Sensitive Air & Light Sensitive
  • Merck 14,128
  • BRN 741856
  • Henry's Law Constant(x 10-6 atm?m3/mol at 25 °C): 135 (Snider and Dawson, 1985)
  • Exposure limitsNIOSH REL: TWA 0.1 ppm, STEL 0.3 ppm, IDLH 2 ppm; OSHA PEL: TWA 0.1 ppm; ACGIH TLV: TWA 0.1 ppm, STEL 0.3 ppm.
  • Stability:Stable, but very readily polymerizes. May have ca. 0.1% hydroquinone added as stabilizer. Flammable. Incompatible with oxidizing agents, reducing agents, oxygen, a variety of other chemicals, light. Very reactive with a wide variety of chemicals. May polymerize violently, especially on contact with strong acids or bases.
  • InChIKeyHGINCPLSRVDWNT-UHFFFAOYSA-N
  • CAS DataBase Reference107-02-8(CAS DataBase Reference)
  • NIST Chemistry Reference2-Propenal(107-02-8)
  • EPA Substance Registry System2-Propenal(107-02-8)
Safety Information
MSDS
Acrolein Usage And Synthesis
  • Aldehyde compoundAcrolein 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.
  • Chemical propertiesAcrolein 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.
  • UsesIt 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.
  • Preparation1. 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.
  • CategoryFlammable liquids
  • ToxicityHighly toxic
  • Acute toxicityOral-Rat LD50: 46 mg/kg; Oral-mouse LD50: 40 mg/kg
  • Stimulation dataEye-Rabbit 1 mg Severe; Skin-Rabbit 5 mg Severity
  • Explosives hazardous characteristicsExplosive when mix with air
  • Flammability hazard characteristicsInflammable in the presence of fire, high temperature and oxidant; stimulating smoke when in combustion
  • Storage and transportationVentilation, low temperature and drying; keeping away from oxidants, acids stored; deterioration after a long period
  • Extinguishing agentDry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent
  • Occupational StandardTWA 0.25 mg/m3; STEL 0.75 mg/m3
  • Chemical Propertiescolourless to slightly yellow liquid
  • Chemical PropertiesAcrolein is a highly flammable, clear to yellowish liquid. It has a piercing, disagreeable odor and causes tears.
  • Physical propertiesColorless to yellow, clear, watery liquid imparting a very sharp, acrid, pungent, or irritating odor. Odor threshold concentrations reported were 0.11 mg/kg by Guadagni et al. (1963), 0.21 ppmv by Leonardos et al. (1969), and 36 ppbv by Nagata and Takeuchi (1990). In addition, Katz and Talbert (1930) reported an experimental detection odor threshold concentration of 4.1 mg/m3 (1.8 ppmv).
  • UsesAcrolein is used as an antimicrobial agentto prevent the growth of microbes againstplugging and corrosion, to control the aquaticweed and algae, in slime control in papermanufacturing, as a tissue fixative, and inleather tanning.
    Because of its widespread use it occursin the environment—in air and water. Afterformaldehyde it is the second most abundantaldehyde, constituting 5% of total aldehydesin air. Acrolein is one of the toxic gasesproduced in a wood or building fire or whenpolyethylene or other polymer substancesburn (Morikawa 1988; Morikawa and Yanai1986). Firefighters are at greater risk ofexposure to this gas.
  • UsesContact herbicide and algicide; injected in water for the control of submerged and floating weeds in irrigation ditches and canals
  • UsesAcrolein is used in the etherification of food starch up to 0.6% and for the esterification and etherification of food starch up to 0.3% with vinyl acetate up to 7.5%.
  • UsesAcrolein is used in the synthesis of acrylic acid.
  • Usesmanufacture 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.
  • DefinitionA colorless liquid unsaturated aldehyde with a pungent odor. It can be polymerized to make acrylate resins.
  • Air & Water ReactionsHighly 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.
  • Reactivity ProfileACROLEIN, [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].
  • Health HazardExtremely 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.
  • Health HazardAcrolein is a highly toxic and corrosive substance. Inhalation of acrolein can cause moderate to severe eye, nose, and respiratory system irritation after a few minutes of exposure to concentrations as low as 0.25 ppm. Higher concentrations can cause immediate and/ or delayed lung injury including pulmonary edema and respiratory insufficiency; fatal reactions have occurred upon exposure to as little as 10 ppm. This substance is a powerful lacrimator, and eye contact with acrolein liquid or vapor can cause severe burns. Skin contact can cause severe redness, swelling, burns with blistering, and corrosion. Acrolein can be absorbed through the skin, leading to systemic effects including delayed pulmonary edema. Ingestion of acrolein can cause gastrointestinal distress, pulmonary congestion, and edema. Acrolein has been reported to be a weak skin sensitizer in some individuals. This substance is regarded as having adequate warning properties.Acrolein is mutagenic in bacteria but did not cause increased tumor incidence in animals exposed chronically by injection or inhalation. Administration to pregnant rats caused malformations and lethality to embryos. Chronic exposure to as little as 0.21 ppm acrolein caused inflammatory changes in lungs, liver, kidneys, and brains of experimental animals.
  • Health HazardAcrolein is a highly toxic compound thatcan severely damage the eyes and respiratorysystem and burn the skin. Ingestion can causeacute gastrointestinal pain with pulmonarycongestion.
    LD50 value, oral (mice): 40 mg/kg
    Acrolein is a strong lachrymator and anasal irritant. Direct contact of liquid in theeyes may result in permanent injury to thecornea. Inhalation can result in severe irritationof the eyes and nose. A concentration of0.5 ppm for 12 minutes can cause intolerableeye irritation in humans. In rats, exposure toa concentration of 16 ppm acrolein in air for4 hours was lethal.
    Acrolein can be absorbed through theskin; the spillage of liquid can cause severechemical burns. Skin contact may lead tochronic respiratory disease and producedelayed pulmonary edema. Subcutaneousadministration of acrolein produced degenerationof fatty liver and a general anestheticeffect.
    LD50 value, subcutaneous (mice): 30 mg/kg
    On the basis of the available data, aconcentration of 68 and 55 ppb may betoxic to aquatic life in fresh and salt water,respectively (U.S. EPA 1980). A concentrationas low as 21 ppb may producechronic toxicity to freshwater aquatic life.Acrolein is reported to be more toxic toaquatic organisms than are phenol, chloroandnitrophenols, aniline, o-xylene, and othertoxic compounds (Holcombe et al. 1987).Rainbow trout, spinally transected, wereexposed to an acutely toxic aqueous concentrationof acrolein to monitor their respiratory–cardiovascular responses. A steadyincrease was recorded in their cough rate.The ventilation rate, oxygen utilization, andheart rate steadily fell throughout their periodof survival.
    In a study on inhalation toxicity in rats,Crane et al. (1986) observed that the exposureto 1 atm of acrolein vapors causedphysical incapacitation. The animals lost theability to walk and expired. In a study oncytotoxicity of tobacco-related aldehydes tocultured human bronchial epithelial cells,acrolein was found to be more toxic thanformaldehyde (Graftstrom et al. 1985). Bothcompounds induced DNA damage.
    Certain sulfur compounds, such as dithiothreitol and dimercaptopropanol, reacted with acrolein to reduce itstoxicity (Dore et al. 1986). Such protectionagainst its toxicity was observed in isolatedrat hepatocytes.
  • Fire HazardUnder 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.)
  • Fire HazardAcrolein is a highly flammable liquid (NFPA rating = 3) and its vapor can travel a considerable distance and "flash back." Acrolein vapor forms explosive mixtures with air at concentrations of 2.8 to 31% (by volume). Carbon dioxide or dry chemical extinguishers should be used for acrolein fires.
  • Flammability and ExplosibilityAcrolein is a highly flammable liquid (NFPA rating = 3) and its vapor can travel a considerable distance and "flash back." Acrolein vapor forms explosive mixtures with air at concentrations of 2.8 to 31% (by volume). Carbon dioxide or dry chemical extinguishers should be used for acrolein fires.
  • Safety ProfileHuman poison by inhalation and intradermal routes. Poison experimentally by most routes. Human systemic irritant and pulmonary system effects by inhalation include: lachrymation, delayed hypersensitivity with multiple organ involvement, and respiratory system damage. Severe eye and skin irritant. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen. Dangerous fire hazard when exposed to heat, flame, or oxidizers. An explosion hazard. Incompatible with amines, SO2, metal salts, oxidants, (light + heat). Violent polymerization reaction on contact with strong acid, strong base, weak acid conditions (e.g., nitrous fumes, sulfur dioxide, carbon dioxide), thiourea, or dimethylamine. When heated to decomposition it emits highly toxic fumes; can react vigorously with oxidizing materials. To fight fire, use CO2, dry chemical, or alcohol foam,
  • Potential ExposureUsed as pharmaceutical; slimicide; and in production of cosmetics and food supplements; as an intermediate in the production of glycerine and in the production of methionine analogs (poultry feed protein supplements). It is also used in chemical synthesis (1,3,6-hexametriol and glutaraldehyde); as a liquid fuel; antimicrobial agent, in algae and aquatic weed control; and as a slimicide in paper manufacture; making plastics, drugs, and tear gas. Also, most allyl compounds may be metabolized to allyl alcohol which is metabolized to acrolein.
  • SourceReported in cigarette smoke (150 ppm) and gasoline exhaust (0.2 to 5.3 ppm) (quoted, Verschueren, 1983). May be present as an impurity in 2-methoxy-3,4-dihydro-2H-pyran (Ballantyne et al., 1989a).
    Acrolein was detected in diesel fuel at a concentration of 3,400 μg/g (Schauer et al., 1999). Gas-phase tailpipe emission rates from California Phase II reformulated gasoline-powered automobiles with and without catalytic converters were 0.06 and 3.8 mg/km, respectively (Schauer et al., 2002).
    Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of acrolein were 63 mg/kg of pine burned, 44 mg/kg of oak burned, and 56 mg/kg of eucalyptus burned.
  • Environmental FateBiological. Microbes in site water degraded acrolein to β-hydroxypropionaldehyde (Kobayashi and Rittman, 1982). This product also forms when acrolein is hydrated in distilled water (Burczyk et al., 1968). When 5 and 10 mg/L of acrolein were statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, complete degradation was observed after 7 days (Tabak et al., 1981). Activated sludge was capable of degrading acrolein at concentrations of 2,300 ppm but no other information was provided (Wierzbicki and Wojcik, 1965)
    Photolytic. Photolysis products include carbon monoxide, ethylene, free radicals and a polymer (Calvert and Pitts, 1966). Anticipated products from the reaction of acrylonitrile with ozone or hydroxyl radicals in the atmosphere are glyoxal, forma
    Groundwater. The half-life for acrolein in groundwater was estimated to range from 14 days to 8 weeks (Howard et al., 1991)
    Chemical/Physical. Wet oxidation of acrolein at 320°C yielded formic and acetic acids (Randall and Knopp, 1980). May polymerize in the presence of light and explosively in the presence of concentrated acids (Worthing and Hance, 1991) forming disacryl, a white plastic solid (Windholz et al., 1983; Humburg et al., 1989). In distilled water, acroleinwas hydrolyzed to β-hydroxypropionaldehyde (Burczyk et al., 1968; Reinert and Rodgers, 1987; Kollig, 1993). The reported hydrolysis rate constant at pH 7 is 6.68 × 108/year (Kollig, 1993). The estimated hydrolysis half-life in water is 22 days (Burczyk et al., 1968)
  • Metabolic pathwayWhen fish are exposed to 14C-acrolein, the metabolites are identified from the edible tissues and there is very little similarity in the metabolism of acrolein among the test species. The most notable observation is that acrolein is never detected in any tissues sampled, and glycidol, glycerol, 1,3- propanediol, and glyceric acid are the major metabolites found in catfish, crayfish, bluegill, and clams, respectively.
  • storageWork with acrolein should be conducted in a fume hood to prevent exposure by inhalation, and splash goggles and butyl rubber gloves should be worn at all times to prevent eye and skin contact. Acrolein should be used only in areas free of ignition sources. Containers of acrolein should be stored in secondary containers in areas separate from amines, oxidizers, acids, and bases.
  • ShippingAcrolein, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquids. Inhalation Hazard Zone A.
  • Purification MethodsPurify 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.]
  • IncompatibilitiesMay form explosive mixture with air. Elevated temperatures or sunlight may cause explosive polymerization. A strong reducing agent; reacts violently with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. 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. Reacts with acids, alkalis, ammonia, amines, oxygenperoxides. Shock-sensitive peroxides or acids may be formed over time. Attacks zinc and cadmium
  • Waste DisposalConsult 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. Incineration. Conditions are 816 C, 0.5 second minimum for primary combustion; 1093 C, 1.0 second for secondary combustion.
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