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Ethylnitrit
Ethy nitrite · nitrousether · ETHYL NITRITE · hyponitrousether · nitrousethylether · Nitrosyl ethoxide · sweetspiritofnitre · sweetspiritofniter
Identifikatoren & physikalische Daten
| CAS No. | 109-95-5 |
|---|---|
| Summenformel | C2H5NO2 |
| Durchschnittliche Molmasse | 75,07 g/mol |
| Monoisotopische Masse | 75,0320284 g/mol |
| SMILES | CCON=O |
| InChIKey | QQZWEECEMNQSTG-UHFFFAOYSA-N |
| PubChem CID | 8026 |
| ChEMBL | CHEMBL1551365 |
| ChEBI | CHEBI:173313 |
| EC No. | 203-722-6 |
| DTXSID | DTXSID9046574 |
| Lokaler Name | Ethylnitrit |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 28,8 |
| Stoffklassen | Nitrogen Compounds -> Nitrates and NitritesFlammable agents - 4th degree |
| Geruch | SWEET, RUM-LIKE ODOR |
| Geschmack | FRUITY TASTEBurning, sweetish taste |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.9 at 59 °F (USCG, 1999) - Less dense than waterwill float0.90 @ 15 °C/15 °C0.900 @ 15.5°C0.792 g/mL at 25 °C |
| Color/Form | Colorless or yellowish, clear liquid |
| Löslichkeit | Slightly soluble in waterdecomposes in watermiscible with alcohol, ether |
| Flammpunkt | -31 °F (USCG, 1999)-31 °F (-35 °C) (CLOSED CUP)59 °F |
| Siedepunkt | 63 °F at 760 mmHg (USCG, 1999)17 °C17 °C @760 [mm Hg]bp 17° |
| Schmelzpunkt | -58 °F (USCG, 1999)FP: -58 °F= -50 °C= 233 deg K |
| Dampfdichte | 2.6 |
| Dampfdruck | 620.0 [mmHg] |
| Brechungsindex | n20/D 1.36 |
| FEMA | 2446 | ETHYL NITRITE |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | liquid |
| Geruch | Aromaticetherealcharacteristic. |
| Geruchsart | ethereal |
| Merck | 3831 |
| Henry-Konstante | 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 (Verteilungskoeffizient) | 1.04 |
| CAS Datenbank | 109-95-5(CAS DataBase Reference) |
| NIST chemische Informationen | Nitrous acid, ethyl ester(109-95-5) |
| EPA chemische Informationen | Ethyl nitrite (109-95-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH220: 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.H220 (86.8%): Extremely flammable gas [Danger Flammable gases] |
|---|---|
| Regulatorische Informationen | Chemical: Nitrous acid, ethyl esterNitrous acid, ethyl ester: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| DOT-Kennzeichnung | Flammable Liquid Poison |
| Brandgefahren | Special Hazards of Combustion Products: Toxic oxides of nitrogen are generated.· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | Flammable liquid. |
| Gesundheitsgefahren | Inhalation or ingestion causes headache, increased pulse rate, decreased blood pressure, and unconsciousness. Contact with liquid irritates eyes and skin. (USCG, 1999)· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| Gefahrenübersicht | 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 narcosisChronic exposure to chemicals with this reactive group can cause hepatitis[CAMEO] |
| DOT-Nummer und Handbuch | 1194 131 |
| FDA-Anforderungen | 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. |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| Reactivity Alerts | Explosive |
| Reactivity Profile | ETHYL NITRITE is a powerful oxidizing agent. Highly dangerous in contact with acid or acid fumes. Dangerous when heated. Decomposes spontaneously at 194 °F. Decomposed by light. |
| Flammable Limits | LOWER, 4.0%UPPER, 50.0% BY VOLUME IN AIR. |
| Brandbekämpfung | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | INHALATION: remove victim from exposureif breathing has stopped, give artificial respirationcall physician.General First Aid: |
| Firefighting Hazards | Closed containers may rupture violently when heated. |
| Expositionsschutz und Persönliche Schutzausrüstung | · 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] |
| Brandbekämpfungsverfahren | 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. |
| Lagerbedingungen | 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. |
| Reinigungsverfahren | Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: |
| Entsorgungsverfahren | 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 |
| Umweltverhalten | 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). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| 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. |
| Artificial Pollution Sources | Ethyl nitrite's production and use for preparing spirit nitrous ether(1), in exhaust from alcohol-fueled vehicles(2), and also for use in organic reactions(3) may result in its release to the environment through various waste streams(SRC). |
| 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 radicalsthe 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) |
| DHS Chemicals of Interest (COI) | Ethyl nitrite110000Flammable chemical that can be released at a facility. |
| Wassergefährdungsklasse (WGK) | WGK 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1194 |
| RTECS-Nr. | RA0810000 |
| R-Sätze (R) | 11-20/21/22-2 |
| Toxizität | cat,LC,inhalation,> 200mg/m3/15M (200mg/m3),Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(1), Pg. 62, 1983. |
| Gefahrensymbole | F,Xn,E |
| Sicherheitshinweise (S) | 7-16-35 |
| Gefahrenklasse | 3Eye Irrit. 2Flam. Liq. 2 |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 109-95-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
The 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 .
Verwenden
Ethyl 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.
Herstellung & Synthese
synthetische
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%).