ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Nitro compounds > Nitroethane
Basic information Summary Nitromethane Nucleophilic addition reaction Preparation of antihypertensive drug methyldopa Dangerous situation Harmful effects and toxic symptoms first aid Protection measures keep in storage chemical property Uses Production method category Toxicity grading acute toxicity Explosive hazard characteristics Storage and transportation characteristics Fire extinguishing agent Occupation standard Safety Related Supplier
Nitroethane Chemical Properties
- Melting point:-90 °C
- Boiling point:114-115 °C(lit.)
- Density 1.045 g/mL at 25 °C(lit.)
- vapor density 2.58 (vs air)
- vapor pressure 15.6 mm Hg ( 20 °C)
- refractive index n
- Flash point:87 °F
- storage temp. Flammables area
- solubility acetone: soluble(lit.)
- pka8.5(at 25℃)
- form Colorless, oily liquid
- PH6 (1g/l, H2O, 25℃)
- explosive limit3.4%(V)
- Water Solubility 4.6 g/100 mL (20 ºC)
- Merck 14,6596
- BRN 1209324
- Henry's Law Constant3.50 at 20.00 °C, 5.86 at 30.00 °C, 9.38 at 40.00 °C, 15.7 at 50.00 °C (inert gas stripping, Bene? and Dohnal, 1999)
- Exposure limitsNIOSH REL: TWA 100 ppm (310 mg/m3), IDLH 1,000 ppm; OSHA PEL: TWA 100 ppm; ACGIH TLV: TWA 100 ppm (adopted).
- Stability:Stability Contact with a variety of materials may cause fire or explosion, especially if heated. Incompatible with amines, strong acids, strong oxidizing agents, combustible materials, metal oxides, strong bases, alkalies.
- CAS DataBase Reference79-24-3(CAS DataBase Reference)
- NIST Chemistry ReferenceEthane, nitro-(79-24-3)
- EPA Substance Registry SystemNitroethane (79-24-3)
- Hazard Codes T,Xn
- Risk Statements 45-10-20/22-68
- Safety Statements 9-23-41-25-45-36/37-53
- RIDADR UN 2842 3/PG 3
- WGK Germany 2
- RTECS KI5600000
- Autoignition Temperature778 °F
- TSCA Yes
- HazardClass 3
- PackingGroup III
- HS Code 29042090
- Hazardous Substances Data79-24-3(Hazardous Substances Data)
- ToxicityAcute oral LD50 for mice 860 mg/kg, rats 1,100 mg/kg (quoted, RTECS, 1985).
Nitroethane Usage And Synthesis
- SummaryIt is colorless oily liquid, with unpleasant odor. The molecular weight is 75.07, the melting point is-50℃. The boiling point is 114 ℃ to 114.8 ℃. The relative density is 1.0528. The refractive index is 1.3917. The flash point is 30 ℃. It can be soluble in methanol, ethanol, ether, chloroform and aqueous alkali miscible, soluble in water. The solubility in water is 4.5mL/100mL(20℃), but the water solubility in this product is 0.9mL/100mL (20 ℃). Steam and air can form explosive mixtures, explosion limit is 3%~5% (in volume). Toxic! Due to chemical properties of nitro ethane is stable, can be used as nitrocellulose and cellulose acetate, vinyl and alkyd resin, wax, grease, fat and dye solvent, is also used as a propellant and fuel additives, pharmaceutical and organic synthesis intermediates. It can be prepared by direct gas phase nitration of ethane or produced by the effect of α-acid chloride and sodium nitrite.
The above information is Chemicalbook Hanya edited.
- NitromethaneNitromethane is the simplest organic nitro compounds, is a colorless oily with a faint aromatic smell of transparent liquid at room temperature, with a larger polar, flammable, poisonous, and explosive. It can be used as fuel. It can be miscible with ethanol, acetone and ethyl ether, is a good solvent and extractant. At the same time, because the nitro α-hydrogen has strong activity, nitromethane is the chemical and organic synthesis of common materials for preparation of drugs, pesticides, explosives, dyes and fibers.
Nitromethane is a synthesis of carbon sub in organic synthesis. By the influence of nitro suction electronic effect, hydrogen of carbon has acidity, and react with alkali to deprotonate. The generation of negative ions of carbon can with aldehydes occurs 1,2 addition generateβ-hydroxy nitro compounds , if loss of water is generated nitro olefin. The reaction is called as Henry reaction. As negative ions of carbon nucleophiles to body, nitromethane can be occurrence conjugate addition with α,β-unsaturated carbonyl compounds under the catalysis of alkali , which is said Michael addition reaction.
In Industry, we can take nitric acid gas phase (350-450℃) nitrification propane method for preparation of the nitro methane and other low-level nitro compounds, such as nitroethane, 1-nitropropane and 2-nitropropane and so on. The reaction is exothermic reaction, free radical mechanism, intermediates is alkyl nitrite homolytic production of free radical CH3CH2CH2O type. Most of them were unstable, prone to C-C bond cleavage, so the reaction obtained a nitro compounds and lower mixture of nitro compounds.
- Nucleophilic addition reactionUnder the cataelysis of alkali, the reaction of nitro alkanes with aldehyde and ketone generated aldehyde condensation to obtain β-nitro alcohols, which was eliminated gradually, and obtained α,β-unsaturated nitro alkanes, which is called Henry.
Because nitro has electron withdrawing effect in nitroethane, and nitro adjacent carbon of hydrogen becomes lively, strip of hydrogen is a negative ion of carbon. And aldehyde carbon of benzaldehyde influenced by oxygen, with some positively charged, so it can be attacked, nitroethane and benzaldehyde react to 1-phenyl-2-nitro-1-propanol, the latter soon remove a molecule of water to obtain 1-phenyl-2-Nitro propylene.
- Preparation of antihypertensive drug methyldopaThe vanillin with dimethyl sulfate methylate to veratraldehyde, then with nitroethane condensation to obtain the 1-(2-nitro-propenyl) 3', 4'-dimethoxy benzene, by reduction with iron powder and hydrolyzed generation to 3 ', 4'-dimethoxy benzene acetone and by cyclization, ring opening, hydrolysis reaction to get methyldopa DL, splitting the levorotatory to obtain an antihypertensive drug methyldopa.
- Dangerous situation(1) It is toxic, inhalation and ingestion of this product can cause poisoning; the high fever will be decomposed, decomposition products are highly toxic.
(2) flammable, secondary combustion risk, ignition is 415 ℃. Vapor can form explosive mixtures with air, lower limit of explosion limit is 3.4%, high limit is unknown. Rapid heating to a high temperature may cause an explosion; in the solid sealed conditions, the effect of strong explosion also exploded. Air in the allowable concentration of the United States is 100 ppm (310mg/m3).
- Harmful effects and toxic symptomsContacting with the skin can cause contact dermatitis, inhalation of high concentration has effect of anesthesia.
- first aidIf the chemicals into the eyes, rinse with water immediately; in case of contacting with skin, rapid wash with soap and water; If a large number of inhalation, immediately moved away from the scene to fresh air. When necessary, carry out artificial respiration; If mistakenly swallowed, emetic, gastric lavage, give the medical gaze, symptomatic treatment; severe cases, do not induce vomiting immediately , should be sent to hospital for treatment.
- Protection measuresProduction site should strengthen ventilation, equipment should be sealed. Operation should wear suitable protective clothing, to prevent skin repeatedly or prolonged contact. Also need to wear a mask or respirator isolation to prevent inhalation of smoke and gas. If the skin of workers is wet or contaminated and should be a quick rinse. If work clothes was wet or contaminated, immediately remove, in order to avoid fire hazard.
- keep in storageUsing glass bottles or drum costumes to prevent mechanical damage; used in containers shall not again for holding. It is best to use open or attached to build warehouse in outdoor storage, must be placed within the flammable liquids designed library. And other flammable liquid or gas should be isolated. Explosive and dangerous work prohibited in the warehouse district around. With the oxidant separated.
- chemical propertyColorless transparent oily liquid. Insoluble in water, immiscible with ethanol, ether, chloroform and alkali solution.
- Uses1.Used as industrial solvents and pharmaceutical intermediates, explosives, rocket fuels, etc.
2.Used as solvent, pharmaceutical intermediate, explosive, rocket fuel and analytical reagent.
3.Used as a solvent, also used in organic synthesis.
4.Solvents. Organic synthesis.
- Production methodIn Industry, mainly uses low carbon alkane direct vapor phase nitration method for production. With methane as raw material, only production of nitromethane; ethane as raw material, can prepare nitromethane and nitroethane two products; with propane as raw materials, can prepare the methane, nitroethane and 1-nitropropane, 2-nitropropane four products. In terms of ethane and propane as raw materials, you can through changes condition to change the proportion of products.
- categoryFlammable liquid
- Toxicity gradingpoisoning
- acute toxicityOral administration of LD50: 1100 mg/kg in rats; oral administration of 860 mg/kg of LD50: in mice
- Explosive hazard characteristicsIn case of thermal explosion.
Flammable risk characteristics in case of fire, high temperature, oxidation of flammable; heat decomposition of toxic nitrogen oxide gas.
- Storage and transportation characteristicswarehouse ventilation low temperature drying and oxidation agent, alkali and hydrocarbons separately.
- Fire extinguishing agentdry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.
- Occupation standardTWA 310 mg/cubic meter
- Chemical Propertiescolourless oily liquid with an unpleasant odour
- Chemical PropertiesNitroethane is a colorless, oily liquid with a mild, fruity odor. The Odor Threshold is 163 ppm.
- Physical propertiesColorless, very flammable liquid with a fruity odor. Odor threshold concentration is 2.1 ppm (quoted, Amoore and Hautala, 1983). Concentrated mixtures usually contain 98 wt % nitroethane and 2 wt % moisture.
- UsesCommon industrial solvent; more recently a commercial artificial nail remover
- UsesSolvent, artificial fingernail glue remover; in organic syntheses. Experimentally as liquid propellant.
- Production MethodsIndustrial production of nitroethane is by vapor-phase nitration of propane with nitric acid, followed by fractional distillation (Baker and Bollmeier 1978). U.S. production was greater than 454 kg in 1975 (HSDB 1988).
- DefinitionChEBI: A nitroalkane that is ethane substituted by a nitro group.
- General DescriptionA colorless oily liquid with a pleasant odor. Flash point of 82°F. Decomposes above 350°F. Density 1.052 g / cm3. Vapors much heavier than air. and insoluble in water. Vapors may irritate skin, eyes and mucous membranes. Produces toxic oxides of nitrogen during combustion. Used as a propellant and as a solvent.
- Air & Water ReactionsHighly flammable. Water soluble.
- Reactivity ProfileThe nitroparaffins, nitromethane, nitropropane, etc. form salts with inorganic bases such as calcium hydroxide. The dry salts are explosive [Chem. Eng. News 30:2344. 1952]. Nitroethane and other nitro compounds are mild oxidizers and should not be heated with easily oxidizable hydrocarbons under confinement [Chem. Eng. News 30:2344. 1940].
- HazardModerate fire risk.Upper respiratory tract irritant, central nervous system impairment, and liver damage.
- Health HazardInhalation causes moderate irritation of respiratory tract. Ingestion causes irritation of mouth and stomach. Contact with liquid causes irritation of eyes and mild irritation of skin.
- Health HazardNitroethane is irritating to the eyes and mucous membranes (HSDB 1988), however, there have been no reports of serious toxic effects of the chemical in humans.
- Fire HazardSpecial Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.
- Industrial usesNitroethane is used as a solvent for cellulose esters, vinyl and other resins and waxes and as a solvent in batteries (Baker and Bollmeier 1978).
- Safety ProfilePoison by intraperitoneal route. Moderately toxic by ingestion. Mildly toxic by inhalation. Causes injury to liver and hdneys. An eye and mucous membrane irritant. Flammable liquid when exposed to heat, sparks, flame, or oxidizers. To fight fire, use alcohol foam, CO2, dry chemical; water can blanket fire. Incompatible with Ca(OH)2, hydrocarbons, hydroxides, inorganic bases, KOH, NaOH, metal oxides, Explodes when heated. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS.
- Potential ExposureNitroethane is used as solvent for polymers, cellulose esters; vinyl, waxes, fats, dyestuffs, and alkyd resins; as a stabilizer. It has been used as a rocket propellant. It is used as an intermediate in pharmaceutical manufacture and in pesticide manufacture.
- Environmental FateChemical/Physical. 2-Nitroethane will not hydrolyze because it does not contain a hydrolyzable functional group.
- MetabolismNitroethane was partially excreted by the lungs when given to rabbits intravenously
(1 g) or orally (1 or 2 g/kg). It was eliminated from the blood within 30 h after
the intravenous dose (Machle et al 1942). A peak blood nitroethane concentration
of 1.10 mg/ml was recorded after oral administration of 1.26 g/kg to rabbit. Following
inhalation exposure of rabbits to about 13,500 p.p.m. or 2,700 p.p.m., peak
nitroethane blood concentrations were 2.70 mg/ml after 360 min, and 0.36 mg/ml
after 500 min, respectively. Blood nitrite and nitrate concentrations increased
during the exposures, indicating that nitrite was formed as a result of the metabo-lism of nitroethane, and was oxidized to nitrate (Scott 1943). Absorption of
nitroethane during inhalation exposure occurs in both the upper (URT) and lower
(LRT) respiratory tract of rats (Stott and McKenna 1984). The isolated URT, LRT
and intact respiratory tract absorbed 65, 71 and 58%, respectively, of the nitroethane
presented at a rate comparable to a normal respiratory minute volume for
rats. The absorption of nitroethane by the URT was linear over a 10-fold exposure
range. During exposures only 2.8 and 2.0% of nitroethane was excreted from the
URT and LRT, respectively.
Porter and Bright (1977) showed that nitroethane is readily converted by glucose oxidase in vitro to acetaldehyde, nitrite, nitrate, hydrogen peroxide and dinitroethane. However, the role of this enzyme in vivo is unknown. Bray and James (1958) recovered a small amount of a mercapturic acid metabolite from the urine of rabbits dosed with nitroethane.
- ShippingUN2842 Nitroethane, Hazard Class: 3; Labels: 3-Flammable liquid.
- Purification MethodsPurify it as described for nitromethane below. A spectroscopic impurity can be removed by shaking it with activated alumina, decanting and distilling it rapidly. [Beilstein 1 IV 170.]
- IncompatibilitiesA nitroparaffin, nitroethane forms explosive mixture with air. Explodes when heated or when shocked; in confined area, with elevated temperatures. A strong reducing agent. Violent reaction with oxidizers, hydrocarbons, other combustibles; amines, metal oxides. Forms shock-sensitive compounds with strong acids; strong alkalis. Attacks some plastics and coatings.
- Waste DisposalIncineration: large quantities of material may require nitrogen oxide removal by catalytic or scrubbing processes.
Nitroethane Preparation Products And Raw materials
- Raw materialsNitromethane2-Nitropropane1-Nitropropane
- Preparation ProductsNitromethane2-(8-BROMO-2,3,6,7-TETRAHYDRO-BENZO[1,2-B:4,5-B']DIFURAN-4-YL)-1-METHYL-ETHYLAMINE2-NitropropaneMethylthioacetaldoxime3,5-DIMETHYLISOXAZOLE-4-CARBONYL CHLORIDES-(-)-Carbidopa3,5-DIMETHYLISOXAZOLE-4-CARBOXYLIC ACID2-Fluorophenylacetone3-Methyl-4-isoxazolecarboxylic acidMethyldopa1-Nitropropane 2-Fluoroisonicotinic acidETHYL 3,5-DIMETHYLISOXAZOLE-4-CARBOXYLATE2-Methoxyphenylacetone2-Fluoropyridine-6-carboxylic acidDL-Norephedrine hydrochloride
- Nitromethane Cesium nitrate 1-(2,3-METHYLENEDIOXYPHENYL)-2-NITROETHANE 1-(2,4,6-TRIHYDROXYPHENYL)-2-NITROETHANE 1-(2,4,5-TRIMETHOXYPHENYL)-2-NITROETHANE 1-BROMO-1-NITROETHANE Tris(hydroxymethyl)nitromethane 2,3-DIMETHYL-2,3-DINITROBUTANE 5-NITROOROTIC ACID, POTASSIUM SALT MONOHYDRATE, 98 PICROLONIC ACID 2-NITROCYCLOHEXANONE 5-Nitrouracil NITROCYCLOPENTANE 5-NITROHEXAHYDROPYRIMIDINE-2,4,6-TRIONE HYDRATE 2-NITRO-1,3-INDANDIONE 2-Methyl-2-nitropropan-1-ol 2-BROMO-2-NITROPROPANE 1,1-Dimethyl-1-nitroethane,1,1-Dimethyl-2-nitroethane