基本情報
- 標準SMILES
CCO[N+](=O)[O-]- InChIKey
IDNUEBSJWINEMI-UHFFFAOYSA-N- 分子式
- C2H5NO3
- 平均分子量
- 91.07 g/mol
- 単同位体質量
- 91.02694302
概要
Ethyl nitrate appears as a clear colorless liquid with a pleasant odor. 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.
名称と識別子
- 優先名称
- Ethyl Nitrate
- IUPAC
- ethyl nitrate
- 現地名
- 硝酸エチル
- 英語名
- Ethyl nitrate
- 分子式
- C2H5NO3
- 分子量
- 91.07
名称と別名
名称をさらに表示
データベース識別子
- CAS
625-58-1- PubChem CID
- 12259
- DTXSID
DTXSID0060806- UNII
- E1ZT886LR5
- EC Number
- 210-903-3
- Nikkaji
- J1.687J
物性
構造計算による物性
- XLogP
- 0.9
- 極性表面積
- 55.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 1
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 47.2
実験および物理化学的性質
Chemical Classes
Nitrogen Compounds -> Nitrates and Nitrites
Flammable agents - 3rd degree
Density
1.1084 @ 20 °C/4 °C
1.004 @ 20°C
Solubility
Sol in alcohol and ether; insoluble in water
1.3 G SOL IN 100 ML WATER @ 55 °C
Sol in water, miscible in ethanol and ethyl ether
Flash Point
50 °F (NFPA, 2010)
50 °F (closed cup)
Boiling Point
87.2 °C @ 762 mm Hg
87.7 °C @760 [mm Hg]
Decomposition
On decomp, they emit toxic fumes. /Nitrates/
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point
-94.6 °C
-112 °C
物理化学的性質
- 融点
- -94.59 °C · -94.59°C
- 沸点
- 87.25 °C · 87.25°C
- 比重(密度)
- 1.1084 · 1.1084
- 屈折率
- 1.3852 · 1.3852
- 溶解性
- 1.3 ml · 1.3 ml を 100 ml の水に 55°C で溶解; アルコールおよびエーテルと混和性
- Henry's Law Constant
- 1.6 · 1.6×10-2 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
- Dielectric constant
- 19.7 · 19.7(20℃)
- EPAの化学物質情報
- Ethyl nitrate (625-58-1)
化学的性質
化学的特性Ethyl nitrate is capable of explosive decomposition when exposed to heat.
安全と法規制
GHS分類
GHS Classification
Danger
H200: (Deleted) Unstable Explosive [Danger Explosives]
P201, P202, P281, P372, P373, P380, P401, and P501 (click each P-code to see the statement)
Danger
H200: (Deleted) Unstable Explosive [Danger Explosives]
P201, P202, P281, P372, P373, P380, P401, and P501 (click each P-code to see the statement)
危険有害性情報
Regulatory Information
Chemical: Nitric acid, ethyl ester
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
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.
NFPA Hazard Classification
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.
4 - Materials that in themselves are readily capable of detonation or explosive decomposition or explosive reaction at normal temperatures and pressures.
安全と保護具
Fire Fighting Procedures
FOAM, CARBON DIOXIDE, DRY CHEM...
EXTINGUISHING METHOD... WATER MAY BE INEFFECTIVE EXCEPT AS BLANKET.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply watt from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-half (1/2) mile radius.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
Precautions should be taken to prevent the spread of any liq that may accidentally escape from a container. ...should not be exposed in.../poorly/ ventilated conditions.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amount of water or soap and water.
If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.
Protective Action Criteria (PAC)
2.2 [ppm]
24 [ppm]
150 [ppm]
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that ethyl nitrate is expected to have very high mobility in soil(SRC). Volatilization of ethyl nitrate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethyl nitrate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 64 mm Hg(4).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from an estimation method(2), indicates that ethyl nitrate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.1 and 120 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1.8(SRC), from an estimated log Kow of 24(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl nitrate, which has a vapor pressure of 64 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl nitrate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 80 days(SRC), calculated from its rate constant of 2.7X10-13 cu cm/molecule-sec at 25 °C(3).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethyl nitrate can be estimated to be 24(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl nitrate is expected to have very high mobility in soil(2).
Natural Pollution Sources
The atmospheric photochemistry of the organosulfur compounds methyl sulfide, ethyl sulfide, & methanethiol was studied with emphasis on gaseous & particulate reaction products & their modes of formation when exposed to sunlight irradiation & various NO(x) mixtures. Experimental results show that ethyl nitrate is a gas-phase photooxidation product of ethyl sulfide.
The yields of alkyl nitrates formed in the NOx-air photooxidations of the homologous series of n-alkanes from ethane through n-octane have been determined at 299 +/- 2 K & 735 torr total pressure for 2 different chemical systems. Alkyl peroxy radicals were generated by reaction of the n-alkanes with OH radicals (generated from the photolysis of methyl nitrite in air) or Cl atoms (from photolysis of CL2 in air). The alkyl nitrate yields obtained from the 2 systems, corrected for secondary reactions, were in agreement within the exptl errors & incr monotonically with the carbon number of the n-alkane, from equal to or less than 1% for ethane to approx 33% for n-octane, with the yields apparently approaching a limit of approx 35% for larger n-alkanes. Data are consistent with the alkyl nitrates being formed almost entirely from the reaction of peroxy radicals with NO, & the ratios of the corrected alkyl nitrate yields reflect the fraction of RO2 radicals which react with NO to form alkyl nitrates.
Atmospheric Concentrations
SOURCE DOMINATED: Ethyl nitrate was detected in air samples collected between November 1988 and April 1989 from Juelich, a city surrounded by five lignite-coal-burning power plants in the Black Forest region of Germany at a mean concn of 47.7 parts per trillion(1).
URBAN/SUBURBAN: Ethyl nitrate was detected not quantified in air samples from Vancouver, British Columbia, Canada(1).
RURAL/REMOTE: Ethyl nitrate was detected in air samples collected in May/June 1989 from Schauinsland, southwest of Juelich in the Black Forest region of Germany at a mean concn of 9.5 parts per trillion(1).
Human Toxicity Excerpts
...HIGHLY TOXIC & IN LARGE DOSES MAY CAUSE DIZZINESS, ABDOMINAL CRAMPS, VOMITING, BLOODY DIARRHEA, WEAKNESS, CONVULSIONS, & COLLAPSE. SMALL, REPEATED DOSES MAY LEAD TO WEAKNESS, GENERAL DEPRESSION, HEADACHE, & MENTAL DISORDERS. /ALKYL NITRATES/
IT IS SAID THAT ETHYL NITRATE HAS ANESTHETIC PROPERTIES & ON INHALATION CAUSES HEADACHE.../PRC: CNS DEPRESSION/ & VOMITING.
A poison by intraperitoneal route. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. A moderate explosion hazard when exposed to heat (explodea @ 185 °F).
Environmental Bioconcentration
An estimated BCF of 2(1) was calculated for ethyl nitrate(SRC), using an estimated log Kow of 1(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(3).
Volatilization from Water/Soil
The Henry's Law constant for ethyl nitrate is estimated as 3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl nitrate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). Ethyl nitrate's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of ethyl nitrate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 64 mm Hg(3).
Non-Human Toxicity Excerpts
IN CATS, 400 MG/KG IN OLIVE OIL IP PRODUCES UNCONSCIOUSNESS, INCR RESP RATE, DILATATION & FIXATION OF PUPILS, & DEATH IN 90 MIN; 300 MG/KG...FOLLOWED BY RECOVERY. MODERATE METHEMOGLOBINEMIA & HEINZ BODY FORMATION...OBSERVED AFTER...125-250 MG/KG.
SUBCUTANEOUS ADMIN OF ETHYL NITRATE TO RABBITS RESULTED IN THE CONVERSION OF HEMOGLOBIN INTO METHEMOGLOBIN. METHEMOGLOBIN REACHED PEAK 1-2 HR AFTER ADMIN & GRADUALLY DECREASED.
INDUCED MUTATIONS IN BACTERIOPHAGE TAB AFTER 24 & 48 HR EXPOSURE. ABILITY TO ALKYLATE DNA SEEMS TO VARY INVERSELY WITH LENGTH OF HYDROCARBON RADICAL.
MUTAGENIC TO E COLI BACTERIOPHAGE T43.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of ethyl nitrate with photochemically-produced hydroxyl radicals is 2.7X10-13 cu cm/molecule-sec at 36 °C(1). This corresponds to an atmospheric half-life of about 80 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Ethyl nitrate may photolyze due to it's absorption in the environmental UV spectrum (>290 nm)(3).
安全データ
- tsca
- TSCA listed
- ridadr
- 0473
- risk_code
- 2
- hazard_code
- E
- safety_code
- 23-24/25
- hazard_class
- 1.1A
- 有毒物質データの
- 625-58-1(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used as a chemical intermediate for production of other organic chemicals; [HSDB]
Organic synthesis of drugs, perfumes, and dyes, and as rocket propellant.
CHEM INT FOR DRUGS, PERFUMES; COMPONENT OF ROCKET PROPELLANTS
Methods of Manufacturing
REACTION OF ETHANOL, UREA NITRATE, AND NITRIC ACID, FOLLOWED BY DISTILLATION
By heating alcohol, urea nitrate, and nitric acid, with subsequent distillation.
応用分野
説明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.
使用Organic synthesis, drugs, perfumes, dyes, rocket propellant.
一般的な説明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.
調製方法
The alkyl nitrates are produced from the corresponding alcohols by esterification with nitric acid in the presence of urea or urea nitrate.
製造方法Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at 10 °C . The reaction was subsequently studied in detail.
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