625-58-1 Usage
Description
Ethyl nitrate has formula C2H5NO3. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes. Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. Originally thought to be a pollutant, formed mainly by the combustion of fossil fuels, recent analysis of ocean water samples reveal that in places where cool water rises from the deep, the water is saturated with alkyl nitrates, likely formed by natural processes.
Chemical Properties
Different sources of media describe the Chemical Properties of 625-58-1 differently. You can refer to the following data:
1. Ethyl nitrate is capable of explosive decomposition when exposed to heat.
2. Colorless liquid; pleasant odor; sweet
taste.Soluble in alcohol and ether;
insoluble in water.
Uses
Organic synthesis, drugs, perfumes, dyes,
rocket propellant.
Production Methods
The alkyl nitrates are produced from the corresponding alcohols by esterification
with nitric acid in the presence of urea or urea nitrate.
Preparation
Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at ?10 °C . The reaction was subsequently studied in detail.
General Description
A clear colorless liquid with a pleasant odor. Flash point 50°F. Prolonged exposure to fire or heat may cause vigorous decomposition and rupturing of the container. Denser than water and insoluble in water. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Organonitrates, such as Ethyl nitrate, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive.
Hazard
Flammable, dangerous, fire and explosion
risk.
Health Hazard
Different sources of media describe the Health Hazard of 625-58-1 differently. You can refer to the following data:
1. Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
2. In humans ethyl nitrate can cause headache, narcosis and vomiting, but no cases of
industrial intoxication have been reported .
Industrial uses
Ethyl nitrate is used in the synthesis of certain drugs, perfumes and dyes. It has
also found some use as a rocket fuel.
Safety Profile
A poison by
intraperitoneal route. Mutation data
reported. A very dangerous fire hazard when
exposed to heat or flame; can react
vigorously with oxibzing materials. A
moderate explosion hazard when exposed to
heat (explodes @ 185'F). To fight fire, use
foam, CO2, dry chemical, water to blanket
fire. Incompatible with Lewis acids. When
heated to decomposition it emits toxic
fumes of NOx. See also NITRATES and ESTERS.
Metabolism
There is no information concerning the in vivo metabolism of ethyl nitrate, but it
seems likely that one route for biotransformation is hydrolysis to yield an alcohol
and nitrate. Such a pathway is common to other alkyl nitrates such as nitroglycerin
and amyl nitrate.
Check Digit Verification of cas no
The CAS Registry Mumber 625-58-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 5 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 625-58:
(5*6)+(4*2)+(3*5)+(2*5)+(1*8)=71
71 % 10 = 1
So 625-58-1 is a valid CAS Registry Number.
InChI:InChI=1/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3
625-58-1Relevant articles and documents
Evidence Against Ion-pair Formation in the Reactions of Ethyl Halides with Silver Salts
Kevill, Dennis N.,Fujimoto, Edward K.
, p. 1149 - 1150 (1983)
Contrary to a previous report, the product ratio from the reaction of ethyl iodide with silver nitrate in ethanol varies with the salt concentration; the product ratios obtained are very similar to those for the corresponding SN2 reactions of triethyloxonium hexafluorophosphate.
Kinetics and Products of the Reactions of Ethyl and n-Propyl Nitrates with OH Radicals
Morin, Julien,Bedjanian, Yuri,Romanias, Manolis N.
, p. 822 - 829 (2016/11/02)
The kinetics of the reactions of ethyl (1) and n-propyl (2) nitrates with OH radicals has been studied using a low-pressure flow tube reactor combined with a quadrupole mass spectrometer. The rate constants of the title reactions were determined under pseudo–first-order conditions from kinetics of OH consumption in high excess of nitrates. The overall rate constants, k1 = 1.14 × 10?13 (T/298)2.45 exp(193/T) and k2 = 3.00 × 10?13 (T/298)2.50 exp(205/T) cm3 molecule?1 s?1 (with conservative 15% uncertainty), were determined at a total pressure of 1 Torr of helium over the temperature range (248–500) and (263–500) K, respectively. The yields of the carbonyl compounds, acetaldehyde and propanal, resulting from the abstraction by OH of an α-hydrogen atom in ethyl and n-propyl nitrates, followed by α-substituted alkyl radical decomposition, were determined at T = 300 K to be 0.77 ± 0.12 and 0.22 ± 0.04, respectively.
FTIR spectroscopic study of the OH-induced oxidation of two linear acetates: Ethyl and n-propyl acetates
Picquet-Varrault,Doussin,Durand-Jolibois,Carlier
, p. 2595 - 2606 (2007/10/03)
OH-induced oxidation mechanisms of ethyl and n-propyl acetates have been investigated at room temperature (298 ± 5 K) and atmospheric pressure by photolysing CH3ONO/acetate/NO mixtures with FTIR spectroscopy as analytical device. The main oxidation products and their yields were as follows: from ethyl acetate, acetic acid (0.75 ± 0.13), acetoxyacetaldehyde (0.15 ± 0.05), acetic anhydride (0.02 ± 0.01), formic acetic anhydride (0.02 ± 0.01) and peroxyacetyl nitrate (PAN); from n-propyl acetate, acetoxyacetaldehyde (0.22 ± 0.06), formic acetic anhydride (0.28 ± 0.03), acetic acid (0.15 ± 0.02), acetaldehyde (0.35 ± 0.10), peroxypropionyl nitrate (PPN) and probably acetoxypropionaldehyde (0.30 ± 0.10). From these data, oxidation schemes of these two acetates were elucidated. This study reveals in particular the specifc reactivity of acetates by confirming the novel α-ester rearrangement proposed recently by Tuazon et al. (J. Phys. Chem. A, 1998, 102, 2316) and then by showing that oxygenated alkoxyl radicals may not follow the same rules of reactivity as other alkoxyl radicals. This last observation shows the necessity for further experiments to understand the influence of the oxygenated function on alkoxyl reactivity.
Nitration of alcohols by nitryl fluoride
Fedorov,Eremenko
, p. 1022 - 1023 (2007/10/03)
A general method for the preparation of nitrates by treatment of alcohols with nitryl fluoride (FNO2) in MeCN in the presence of KF has been developed.