HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ameisensäure-ethylester
FORMIC ACID ETHYL ESTER · ETHYL METHANOATE · Ethyl forMat · Ethylformiat · ethyl formiate · Areginal · HCOOC2H5 · FEMA 2434
Identifikatoren & physikalische Daten
| CAS No. | 109-94-4 |
|---|---|
| Summenformel | C3H6O2 |
| Durchschnittliche Molmasse | 74,08 g/mol |
| Monoisotopische Masse | 74,03677943 g/mol |
| SMILES | CCOC=O |
| InChIKey | WBJINCZRORDGAQ-UHFFFAOYSA-N |
| PubChem CID | 8025 |
| ChEMBL | CHEMBL44215 |
| ChEBI | CHEBI:52342 |
| EC No. | 203-721-0 |
| DTXSID | DTXSID6040117 |
| Lokaler Name | Ameisensäure-ethylester |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 26,1 |
| Stoffklassen | Flammable agents - 3rd degree |
| Solvents | Solvents -> Esters (<C12) |
| SpringerMaterials Properties | Coriolis coupling |
| Duftstoffe | Fragrance Ingredient (Ethyl formate) -> IFRA transparency List |
| Pestizide | InsecticidesActive substance -> EU Pesticides database: Not approved |
| LogP (Verteilungskoeffizient) | 0.230.27 |
| Geruch | Fruity odor. |
| Geschmack | SLIGHTLY BITTER TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.922 at 68 °F (USCG, 1999) - Less dense than waterwill float0.9168 @ 20 °CCONVERSION FACTORS: 1 MG/L EQUIV TO 330 PPM1 PPM EQUIV TO 3.03 MG/CU MDENSITY OF SATURATED AIR: 1.25 (AIR= 1)Relative density (water = 1): 0.920.917-0.9220.921 g/mL at 20 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | MOBILE LIQUIDWATER-WHITE LIQColorless liquid. |
| Schmelzpunkt | -80 °C (lit.) |
| Siedepunkt | 52-54 °C (lit.) |
| Dampfdichte | 2.5 (vs air) |
| Dampfdruck | 15.16 psi ( 55 °C) |
| Brechungsindex | n20/D 1.359(lit.) |
| FEMA | 2434 | ETHYL FORMATE |
| Flammpunkt | 7 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Miscible with alcohol, benzene, and ether (Hawley, 1981)11 g/100 mL (18 ºC) |
| Aggregatzustand | Liquid |
| Farbe | Clear |
| Geruch | Characteristicpleasant aromatic. |
| Biologische Quelle | synthetic |
| Geruchsart | ethereal |
| Geruchsschwelle | 2.7ppm |
| Explosionsgrenze | 16% |
| Spezifische Wärmekapazität | Cp(liquid): 2.02 J/(g·K), at 25℃ |
| JECFA Number | 26 |
| Merck | 14,3807 |
| BRN | 906769 |
| Henry-Konstante | 0.097(x 10-3 atmm3/mol) at 5.00 °C, 0.13 at 10.00 °C, 0.17 at 15.00 °C, 0.23 at 20.00 °C, 0.29 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005) |
| Dielektrizitätskonstante | 8.4(6℃) |
| Stabilität | Stable. Extremely flammable. May form explosive mixtures with air. Note low flash point and wide explosive limits. Incompatible with strong oxidizing agents, strong bases, strong acids, nitrates. |
| Hauptanwendungen | agriculturecleaning productscosmeticsenvironmentalflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C3H6O2/c1-2-5-3-4/h3H,2H2,1H3 |
| InChIKey | WBJINCZRORDGAQ-UHFFFAOYSA-N |
| SMILES | CCOC=O |
| LogP (Verteilungskoeffizient) | 1.504 at 25℃ |
| CAS Datenbank | 109-94-4(CAS DataBase Reference) |
| NIST chemische Informationen | Formic acid, ethyl ester(109-94-4) |
| EPA chemische Informationen | Ethyl formate (109-94-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P330, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.6% (11 of 1923) of reports.H225 (99.4%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Formic acid, ethyl esterStatus: Active Update: 30-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17274Formic acid, ethyl ester: HSNO Approval: HSR001148 Approved with controlsThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Formic acid, ethyl ester: Human health tier I assessment |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Behavior in Fire: Vapor is heavier than air and may travel long distance to a source of ignition and flash back. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting. Risk of fire and explosion on contact with strong oxidants. |
| Brandpotenzial | Burning Rate: 3.6 mm/min.DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS. |
| Gesundheitsgefahren | Inhalation of vapor causes slight irritation of the eyes and rapidly increasing irritation of the nose. High concentrations cause deep narcosis within a few minutes followed by death within a few hours. Contact with liquid causes moderate irritation of eyes and mild irritation of skin. Ingestion causes irritation of mouth and stomachmay cause deep narcosis and death if not treated. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | Liquid causes second degree burns after contact for a few minutes. [CHRIS] The anesthetic potency of ethyl formate is greater than ethanol, acetone, and alkanes such as pentane, but less than chlorinated hydrocarbons and ethyl ether. TLV Basis = upper respiratory tract irritantReported to be irritating at 321 ppm[ACGIH] Esters may induce narcosis in animals, but workers' exposures are limited by irritating effects. See appendix in: [Dick RB, et al. Chemicals in the workplace: incorporating human neurobehavioral testing into the regulatory process. Am J Ind Med. 1998 May33(5):439-53.] Inhalation of high concentrations causes drowsiness and unconsciousnessA skin, eye, and respiratory tract irritant[ICSC] |
| DOT-Nummer und Handbuch | 1190 129 |
| FDA-Anforderungen | Substance added directly to human food affirmed as generally recognized as safe (GRAS). |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| EG-Einstufung | Symbol: F, XnR: 11-20/22-36/37S: (2)-9-16-24-26-33 |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: II |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Use powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Refer for medical attention . |
| 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 | Excerpt from NIOSH Pocket Guide for Ethyl formate:General First Aid:(General first aid procedures) |
| Sichere Lagerung | Fireproof. Separated from strong oxidants. Cool. |
| Firefighting Hazards | Vapor is heavier than air and may travel long distance to a source of ignition and flash back. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).100.0 [ppm] |
| Brandbekämpfungsverfahren | Dry chemical, ... carbon dioxide. |
| Lagerbedingungen | KEEP TIGHTLY CLOSED & PREFERABLY IN CONTACT WITH CALCIUM CHLORIDE. |
| Reinigungsverfahren | 1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE AREA OF SPILL OR LEAK. 3. FOR SMALL QUANTITIES, ABSORB ON PAPER TOWELS. EVAPORATE IN A SAFE PLACE (SUCH AS A FUME HOOD). ALLOW SUFFICIENT TIME FOR EVAPORATING VAPORS TO COMPLETELY CLEAR THE HOOD DUCTWORK. BURN THE PAPER IN A SUITABLE LOCATION AWAY FROM COMBUSTIBLE MATERIALS. LARGE QUANTITIES CAN BE COLLECTED AND ATOMIZED IN A SUITABLE COMBUSTION CHAMBER. ETHYL FORMATE SHOULD NOT BE ALLOWED TO ENTER A CONFINED SPACE, SUCH AS A SEWER, BECAUSE OF THE POSSIBILITY OF AN EXPLOSION. |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| 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.1. BY ABSORBING IT IN VERMICULITE, DRY SAND, EARTH OR A SIMILAR MATERIAL AND DISPOSING IN A SECURED SANITARY LANDFILL. 2. BY ATOMIZING IN A SUITABLE COMBUSTION CHAMBER. |
| Zielorgane | Eyes, respiratory system, central nervous system |
| Umweltverhalten | TERRESTRIAL FATE: If released to soil, ethyl formate would readily volatilize from the surface layers of soil as well as leach. While no data were located concerning the degradation in soil, it would be expected to readily degrade by chemical hydrolysis, especially in alkaline soil, and biodegrade. (SRC)AQUATIC FATE: Ethyl formate has a relatively high Henry's Law constant of 3.85X10-4 atm-cu m/mol(1) and if released to water, it will be lost due to evaporation. A volatilization half-life of 4.5 hrs was predicted for ethyl formate from a model river 1 m deep, flowing at 1 m/sec with a wind velocity of 3 m/sec(2,SRC). It would not be expected to sorb to sediment or bioconcentrate in aquatic organisms. Chemical hydrolysis will be an important fate process, especially in alkaline waters. The hydrolytic half-life is 3.1 days and 7.5 hr at pH 7 and 8, respectively(3,SRC). Based on limited data from screening tests supplemented by predictions of mathematical models and data on similar chemicals, ethyl formate should rapidly biodegrade(SRC).ATMOSPHERIC FATE: The half-life of ethyl formate in the atmosphere is estimated to be 11 days as a result of reaction with photochemically-produced hydroxyl radicals(1). Being fairly soluble in water, it should be readily washed out of the air by rain(SRC). |
| Lebensmitteluntersuchungswerte | Ethyl formate was identified, but not quantified, in roasted filberts(1), beer(2), wine(6,7), Korean chamchwi(3), blue cheese(4), and apples and pears(5). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour and by ingestion.inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Shortness of breath. Headache. Drowsiness.Redness.Redness. Pain.Sore throat. Further see Inhalation.irritation eyes, upper respiratory systemIn Animals: narcosis |
| Medical Surveillance | Employees should be screened for history of certain medical conditions which might place the employee at increased risk from ethyl formate exposure. /These include/ chronic respiratory disease ... skin disease ... liver disease ... kidney disease. ... Any employee developing the above-listed conditions should be referred for further medical examination. |
| Soil Adsorption/Mobility | Using a reported water solubility of 88.25 g/L(1) for ethyl formate, an estimated Koc of 8 was calculated using a regression equation(2,SRC). A Koc of 4 was estimated from molecular structure(3). According to a suggested classification scheme(3), this estimated Koc suggests that ethyl formate will be highly mobil in soil (SRC). |
| Natural Pollution Sources | /IT IS/ REPORTED IN OIL OF BORONIA DENTIGEROIDES. IT HAS BEEN IDENTIFIED IN FLORIDA ORANGE JUICE, SEVERAL VARIETIES OF HONEY, APPLES AND PEARS, & DISTILLED LIQUORS, SUCH AS RUM.Ethyl formate occurs widely in fruit(1). |
| Human Toxicity Excerpts | /IT IS/ IRRITATING TO SKIN, MUCOUS MEMBRANES, & IN HIGH CONCENTRATIONS.../A CNS DEPRESSANT/.No irritation was noted after a 48 hr closed-patch test of 4% ethyl formate on human subjects.Slight eye irritation in human subjects and strong persistent nasal irritation were noted on exposure to 330 ppm in the air. ... The irritating effects on the eyes and respiratory tract are probably due to rapid hydrolysis of the ester on contact with water, with the formation of alcohol and formic acid.THERE ARE NO REPORTS OF TOXIC EFFECTS ON HUMANS EXCEPT SLIGHT IRRITATION OF THE EYES AND NOSE...10,500 PPM CAUSES MODERATE BUT PROGRESSIVE IRRITATION OF EYES AND NOSE, REMAINING 4 HR AFTER EXPOSURE.THE ANESTHETIC POTENCY /IS/ ... LESS THAN THAT OF CHLORINATED HYDROCARBONS & ETHYL ETHER, BUT IT /IS/ ... MORE ACTIVE ... THAN ETHANOL, ACETONE AND ALIPHATIC HYDROCARBONS ... . |
| Fish/Seafood Concentrations | Ethyl formate was found in mussels at 4.08 ppm(1). |
| Artificial Pollution Sources | Ethyl formate maybe released to the environment as a result of its production, transport, disposal and use as a synthetic flavoring agent in lemonades, chewing gum, ice cream, essences (apple, pineapple, banana, and peach flavors), artificial rum and arracas a fungicide and larvicide for tobacco, cereals, dried fruit, and other crops(1,3) and as a solvent for cellulose nitrate and acetate, as an acetone substitute and fumigant in packaged food, and in organic synthesis(2-4). |
| FIFRA-Anforderungen | The food additive ethyl formate may be safely used in or on specified dried fruits in accordance with the following conditions: it is used or intended for use in or on raisins and dried Zante currants as a bulk and package fumigant.The food additive ethyl formate may be safely used in or on specified dried fruits in accordance with the following conditions: it is used in accordance with directions registered with the U.S. EPA, and so used that the total formic acid present free and combined, in the finished product shall not exceed 250 ppm.The food additive ethyl formate may be safely used in or on specified dried fruits in accordance with the following conditions: to assure safe use of the additive, its label and labeling shall conform to that registered with the USEPA. |
| Berufliche Expositionsstufe (OEB) | A |
| Arbeitsplatzgrenzwert (OEL) | TWA: 100 ppm (300 mg/m3) |
| Wassergefährdungsklasse (WGK) | 1 |
| Sofort lebensgefährliche Konzentration | 1,500 ppm |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1190 |
| Zollcode | 29151300 |
| RTECS-Nr. | LQ8400000 |
| R-Sätze (R) | 11-20/22-36/37 |
| Toxizität | LD50 orally in rats: 4.29 g/kg (Smyth) |
| Gefahrensymbole | F,Xn |
| Sicherheitshinweise (S) | 9-16-24-26-33 |
| Gefahrenklasse | 3Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 109-94-4(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 851 °F |
Anwendungen & Verwendung
Beschreibung
Der Ameisensäureethylester bildet eine farblose, wasserunlösliche, nach Arrak riechende Flüssigkeit. Die Verbindung wird in der Lebensmittelindustrie zur Herstellung künstlicher Arrak- und Rumessenzen verwendet. In der Humanmedizin wurde der Ester gegen Kehlkopf- und Rachenkatarrh angewendet. Die Veterinärmedizin setzte Ameisensäureethylester zur Behandlung der Maul- und Klauenseuche (MKS) ein.
Beschreibung
Ethyl formate is an ester formed when ethanol (an alcohol) reacts with formic acid (a carboxylic acid). It is also known as ethyl methanoate because formic acid is also known as methanoic acid. Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries.
Occurrence
Reported in the oil of Boronia dentigeroides; it has been identified in Florida orange juice, several varieties of honey, apple and pear and in distilled liquors, such as rum. Also reported found in peach, raspberry, strawberry, pineapple, cabbage, vinegar, cheeses, butter, cream, milk powder, cooked beef, beer, coffee, tea, honey, corn oil, brandy and mussels.
Verwenden
Ethyl Formate is a flavoring agent that occurs naturally in some plant oils, fruits, and juices but does not occur naturally in the ani- mal kingdom. it is used in food at a maximum level, as served, of 0.05% in baked goods; 0.04% in chewing gum, hard candy, and soft candy; 0.02% in frozen dairy desserts; 0.03% in gelatins, puddings, and fillings; and 0.01% in all other food categories.Ethyl formate is also used as a solvent for nitrocellulose; as fungicide and larvicide for tobacco, cereals, dried fruits, etc.; in organic synthesis.
Herstellung & Synthese
synthetische
Ethyl Formate is an ester of formic acid and is prepared by esterification of formic acid with ethyl alcohol or by distillation of ethyl acetate and formic acid in the presence of concentrated sulfuric acid.