기본 정보
- 표준 SMILES
CCON=O- InChIKey
QQZWEECEMNQSTG-UHFFFAOYSA-N- 분자식
- C2H5NO2
- 평균 분자량
- 75.07 g/mol
- 단동위원소 질량
- 75.0320284
개요
Ethyl nitrite, solution appears as a clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31 °F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.
이름 및 식별자
- 우선 이름
- Ethyl Nitrite
- IUPAC
- ethyl nitrite
- 현지명
- 에틸 니트리트(아질산에틸)
- 영어명
- Ethyl nitrite
- 분자식
- C2H5NO2
- 분자량
- 75.07
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
109-95-5- PubChem CID
- 8026
- DTXSID
DTXSID9046574- ChEMBL
CHEMBL1551365- ChEBI
CHEBI:173313- UNII
- 8C7CJ279RV
- EC Number
- 203-722-6
- Nikkaji
- J47.917I
물성
구조 계산 물성
- XLogP
- 0.4
- 극성 표면적
- 38.7 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 5
- 형식 전하
- 0
- 복잡도
- 28.8
실험 및 물리화학적 성질
Chemical Classes
Nitrogen Compounds -> Nitrates and Nitrites
Flammable agents - 4th degree
Taste
FRUITY TASTE
Burning, sweetish taste
Density
0.9 at 59 °F (USCG, 1999) - Less dense than water; will float
0.90 @ 15 °C/15 °C
0.900 @ 15.5°C
Flash Point
-31 °F (USCG, 1999)
-31 °F (-35 °C) (CLOSED CUP)
Boiling Point
63 °F at 760 mmHg (USCG, 1999)
17 °C
17 °C @760 [mm Hg]
Melting Point
-58 °F (USCG, 1999)
FP: -58 °F= -50 °C= 233 deg K
-50 °C
물리화학적 성질
- 끓는 점
- 17 ° · bp 17°
- 밀도
- 0.792 g/mL · 0.792 g/mL at 25 °C
- 굴절률
- 20 · n20/D 1.36
- FEMA
- 2446 · 2446 | ETHYL NITRITE
- 인화점
- 59 °F · 59 °F
- 저장 조건
- 2 · 2-8°C
- 물리적 상태
- liquid
- 냄새
- 에테르의 냄새
- 냄새 유형
- 미묘한
- Merck
- 3831 · 3831
- Henry's Law Constant
- 1.1 · 1.1×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- 1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3
- InChIKey
- QQZWEECEMNQSTG-UHFFFAOYSA-N
- SMILES
- CCON=O
- LogP
- 1.04 · 1.04
- NIST
- Nitrous acid, ethyl ester(109-95-5)
- EPA
- Ethyl nitrite (109-95-5)
화학적 성질
Ethyl nitrite has a characteristic ether-like odor.
안전 및 규제
GHS 분류
GHS Classification
Danger
H220: Extremely flammable gas [Danger Flammable gases]
P203, P210, P222, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P377, P381, P403, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 13.2% (36 of 272) of reports.
Danger
H220 (86.8%): Extremely flammable gas [Danger Flammable gases]
유해성 정보
Regulatory Information
Chemical: Nitrous acid, ethyl ester
Nitrous acid, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard
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.)
Fire Hazards
Special Hazards of Combustion Products: Toxic oxides of nitrogen are generated.
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Inhalation or ingestion causes headache, increased pulse rate, decreased blood pressure, and unconsciousness. Contact with liquid irritates eyes and skin. (USCG, 1999)
· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.
Hazards Summary
Inhalation or ingestion can cause headache, rapid pulse, hypotension, and unconsciousness. [CHRIS] One fatality was reported after the breakage of a 4 liter bottle containing 24% ethyl nitrite in alcohol. Three cases of methemoglobinemia were reported in workers exposed during the synthesis of hydantoin (glycolylurea). [HSDB] Inhalation of high concentrations causes narcosis; Chronic exposure to chemicals with this reactive group can cause hepatitis; [CAMEO]
FDA Requirements
Ethyl nitrite is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
안전 및 보호
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
INHALATION: remove victim from exposure; if breathing has stopped, give artificial respiration; call physician.
General First Aid:
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]
Fire Fighting Procedures
Use water spray, dry chemical, foam, or carbon dioxide. Use water spry to keep fire-exposed containers cool. Fight fire from protected location or maximum possible distance.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or 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 water 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.
Storage Conditions
KEEP TIGHTLY CLOSED, IN A COOL PLACE, PROTECTED FROM LIGHT.
Store away from heat, oxidizers, and sunlight. Must be stored in a dry location. Outside or detached storage is preferred.
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
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 amounts 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.
Isolation and Evacuation
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Immediate precautionary measure
독성 정보
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that ethyl nitrite is expected to have very high mobility in soil(SRC). Volatilization of ethyl nitrite from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethyl nitrite from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 620 mm Hg(SRC), determined from a fragment constant method(4). A decomposition rate has not been published, however it is known that ethyl nitrite is slightly soluble(5) and decomposes in water(5). In addition, decomposition of ethyl nitrite is hastened by air, light, and moisture(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that ethyl nitrite 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 8.7X10-5 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 7 and 146, respectively(SRC). A decomposition rate has not been published, however it is known that ethyl nitrite is slighlty soluable in water and is decomposed by it(7). In addition, decomposition of ethyl nitrite is hastened by air, light, and moisture(7). According to a classification scheme(5), an estimated BCF of 2(SRC), from an estimated log Kow(8) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: A decomposition rate has not been published, however it is known that decomposition of ethyl nitrite is hastened by air, light,and moisture(4). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl nitrite, which has an estimated vapor pressure of 620 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Vapor-phase ethyl nitrite 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 34.5 days(SRC), calculated from its rate constant of 1.75X10-12 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 nitrite can be estimated to be 81(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl nitrite is expected to have high mobility in soil.
Human Toxicity Excerpts
MAY CAUSE METHEMOGLOBINEMIA & HYPOTENSION, &, IN HIGH CONCN.../SRP: CNS DEPRESSION/.
Industrial intoxications characterized by headache, tachycardia, and methemoglobinemia have occurred. A fatality has been described following the inhalation of ethyl nitrite after accidental breakage of a 4 liter bottle containing 24% ethyl nitrite in alcohol.
Three cases of ethyl nitrite intoxication have been reported from Czechoslovakia during a synthesis of hydantoin (glycolylurea). Symptoms of both "nitrite" effect and methemoglobinemia were noted. In addition, there was a vasodilator effect upon the blood vessels of the sclerae, producing a peculiar redness of the eyes, ... No Heinz bodies were seen.
ADMIN OF SWEET SPIRITS OF NITRE (4% ETHYL NITRITE IN 70% ETHANOL) WAS FOLLOWED BY ACUTE METHEMOGLOBINEMIA & SEVERE ANOXIC METABOLIC ACIDOSIS IN INFANT TWINS, METHYLENE BLUE ADMIN REVERSED METHEMOGLOBINEMIA IN BOTH, BUT ONE TWIN DIED FROM THE CONSEQUENCES OF HYPOXEMIA.
For more Human Toxicity Excerpts (Complete) data for ETHYL NITRITE (6 total), please visit the HSDB record page.
Environmental Bioconcentration
An estimated BCF of 2 was calculated for ethyl nitrite(SRC), using an estimated log Kow of 1.4(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.
Volatilization from Water/Soil
The Henry's Law constant for ethyl nitrite is estimated as 8.7X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl nitrite 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 7 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 6 days(SRC). Ethyl nitrite's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of ethyl nitrite from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 620 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts
Mice and cats exposed for 15 min to 15 ppm did not show recognizable effects.
Inhalation of ethyl nitrite by dogs results in as much as 70 mm Hg depression in the blood pressure. This lasts approx 2 min after a single inhalation. Methemoglobin is formed but Heinz bodies have not been found.
Environmental Abiotic Degradation
A decomposition rate has not been published, however it is known that ethyl nitrite is slighlty soluable in water and is decomposed by it(2). In addition, decomposition of ethyl nitrite is hastened by air, light,and moisture(2). The rate constant for the vapor-phase reaction of ethyl nitrite with photochemically-produced hydroxyl radicals is 1.75X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 34 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
Probable Routes of Human Exposure
Occupational exposure to ethyl nitrite may occur through inhalation and dermal contact with this compound at workplaces where ethyl nitrite is produced or used. The general population may be exposed to ethyl nitrite via inhalation of auto exhaust from alcohol-fueled vehicles and ingestion of food in which ethyl nitrite has been used as a synthetic flavoring. (SRC)
Other Environmental Concentrations
ETHYL NITRITE IS DETECTED IN EXHAUSTS WHEN METHANOL & ETHANOL ARE USED AS FUELS. ETHYL NITRITE CONTENT OF EXHAUST FROM A VEHICLE FUELED WITH ETHANOL & OPERATED AT HIGHWAY CONDITIONS IS 1.0-9.0 & 16.5-27.0 PPM, RESPECTIVELY, IN INITIAL 1/2 HR & IN 17 HR.
Environmental Fate/Exposure Summary
Ethyl nitrite's production and use for preparing spirit nitrous ether and also for use in organic reactions may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 620 mm Hg at 25 °C indicates ethyl nitrite will exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl nitrite will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 34 days. If released to soil, ethyl nitrite is expected to have high mobility based upon an estimated Koc of 81. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole. Ethyl nitrite may volatilize from dry soil surfaces based upon its vapor pressure. If released into water, ethyl nitrite is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 7 hours and 146 hours, respectively. A decomposition rate has not been published, however it is known that ethyl nitrite is slighlty soluable in water and is decomposed by it. In addition, decomposition of ethyl nitrite is hastened by air, light,and moisture. An estimated BCF of 2 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to ethyl nitrite may occur through inhalation and dermal contact with this compound at workplaces where ethyl nitrite is produced or used. The general population may be exposed to ethyl nitrite via inhalation of auto exhaust from alcohol-fueled vehicles and ingestion of food in which ethyl nitrite has been used as a synthetic flavoring. (SRC)
규제 정보
FDA Requirements
Ethyl nitrite is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
DHS Chemicals of Interest (COI)
Ethyl nitrite
1
10000
Flammable chemical that can be released at a facility.
안전 데이터
- wgk
- WGK 1
- tsca
- TSCA listed
- rtecs
- RA0810000
- ridadr
- UN 1194
- 독성
- cat,LC,inhalation,> 200mg/m3/15M (200mg/m3),Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(1), Pg. 62, 1983.
- risk_code
- 11-20/21/22-2
- hazard_code
- F,Xn,E
- safety_code
- 7-16-35
- 포장분류
- I
- 위험 등급
- 3
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2
- 스토리지 클래스
- 3 - Flammable liquids
- 유해 물질 데이터
- 109-95-5(Hazardous Substances Data)
화학 및 산업
약리 정보
Mechanism of Action
THE REACTIONS OF HUMAN HEMOGLOBIN WITH SODIUM NITRITE AND ETHYL NITRITE IN DEOXYGENATED MEDIA HAVE BEEN EXAMINED IN KINETIC DETAIL. ETHYL NITRITE REACTS WITH HEMOGLOBIN AT RATES THAT ARE AT LEAST 10 TIMES SLOWER THAN THOSE EXTRAPOLATED FOR NITROUS ACID, & HYDROLYSIS OF ALKYL NITRITE IS NOT COMPETITIVE WITH OXIDATION OF HEMOGLOBIN. THE EXPERIMENTAL RESULTS ARE INTERPRETED TO DESCRIBE ALKYL NITRITE, AND PRESUMABLY, NITROUS ACID ASSOCIATION WITH HEMOGLOBIN FOLLOWED BY RATE-LIMITED ELECTRON TRANSFER RESULTING IN NITRIC OXIDE AND ALKOXIDE (OR HYDROXIDE) PRODN. PROTON TRANSFER RESULTING IN ALC (OR WATER) FORMATION OCCURS SUBSEQUENT TO THE RATE-LIMITING STEP AS DO REACTIONS OF HEMOGLOBIN WITH NITRIC OXIDE.
THE REACTION OF HUMAN HEMOGLOBIN AND SPERM WHALE MYOGLOBIN UNDER AEROBIC CONDITIONS WITH ETHYL NITRITE HAVE BEEN EXAMINED. ETHYL NITRITE CONVERTS TWO EQUIVALENTS OF OXYHEMOGLOBIN TO THEIR OXIDIZED COUNTERPARTS WITH CONCURRENT PRODN OF ONE EQUIVALENT OF MOLECULAR OXYGEN, NITRATE ION, & ETHYL ALCOHOL.
용도 및 제조
Uses
Used to flavor foods and to synthesize other organic chemicals; [HSDB]
For preparing spirit nitrous ether
CHEM INTERMEDIATE; FLAVOR IN FOODS & BEVERAGES
Organic reactions, synthetic flavoring
FLAVORS USEFUL IN RUM, BRANDY, FRUIT FLAVORS.
Methods of Manufacturing
REACTION OF NITROUS ACID & ETHANOL
Made by action of sodium nitrite on mixture of alcohol and sulfuric acid in the cold. In lab ethyl nitrite gas is ... Generated by placing 20 L of 90% ethanol in suitable vessel, diluting with 200 L of water ... While stirring, adding to dilute alcohol 18.3 kg of nitrosyl chloride @ the rate of 2.25 kg/hr ... Chase, US patent 2,615,896 (1952).
General Manufacturing Information
Nitrous acid, ethyl ester: ACTIVE
FEMA LIST OF GRAS SUBSTANCES REPORT USAGE AS SYNTHETIC FLAVOR INGREDIENT IN NON-ALCOHOLIC BEVERAGES 3.0 PPM, ICE CREAM, ICES...4.5 PPM; CANDY 0.10-8.0 PPM; BAKED GOODS 0.10 PPM; CHEWING GUM 3.9 PPM; SYRUPS 52 PPM; ICINGS 13 PPM.
FEMA NUMBER 2446
In prepn of spirit nitrous ether by mixing with 21 parts alcohol by weight.
응용 분야
개요The chemical compound ethyl nitrite is an alkyl nitrite. It may be prepared from ethanol Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known as Witdulsies and sold in pharmacies. It is known as a traditional Afrikaans remedy and may have Dutch roots, as the same remedy is apparently made by the Germano-Dutch Amish people in the USA. However FDA has blocked over-the-counter sales of this same remedy, known in the USA as sweet nitrite or sweet spirit of nitre since 1980 .
용도Ethyl Nitrite is an S-nitrosylating agent that improve tissue oxygenation in humans and sheep at normoxia and at reduced fraction of inspired oxygen during microvasculature. Ethyl Nitrite is also used as a therapeutic gas utilized in neonatal Intensive Care Unit.
일반 설명A clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31°F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.
제조 방법
From sodium nitrite in aqueous solution by displacing the acid with H2SO4 in the presence of ethyl alcohol; it forms azeotropic mixtures with isopentane (85%), amyl bromide (40%) and carbon disulfide (96%).
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