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Methylformiat
HCOOCH3 · METHYL METHANOATE · Methyl formate analytical standard · Metil · formiatedemethyle · formiatedemethyle(french) · Methyl forMate (C1:0) Solution · METHYL FORMATE FOR SYNTHESIS 1 L
Identifikatoren & physikalische Daten
| CAS No. | 107-31-3 |
|---|---|
| Summenformel | C2H4O2 |
| Durchschnittliche Molmasse | 60,05 g/mol |
| Monoisotopische Masse | 60,02112937 g/mol |
| SMILES | COC=O |
| InChIKey | TZIHFWKZFHZASV-UHFFFAOYSA-N |
| PubChem CID | 7865 |
| ChEMBL | CHEMBL295026 |
| ChEBI | CHEBI:77699 |
| EC No. | 203-481-7 |
| DTXSID | DTXSID5025609 |
| Lokaler Name | Methylformiat |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 4 |
| Formalladung | 0 |
| Komplexität | 18 |
| Stoffklassen | Flammable agents - 4th degree |
| Solvents | Solvents -> Esters (<C12) |
| SpringerMaterials Properties | Coriolis coupling |
| LogP (Verteilungskoeffizient) | log Kow = 0.03-0.21 |
| Geruch | AgreeablePleasant odor. |
| Dichte | 0.977 at 68 °F (USCG, 1999) - Less dense than waterwill float0.987 at 15 °C/15 °CDENSITY OF SATURATED AIR: 1.83 (AIR= 1)Relative density (water = 1): 0.970.975 @ 20°C0.974 g/mL at 20 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 0.325 mPa-s at 25 °C |
| Color/Form | Colorless liquid [Note: A gas above 89 degrees F]. |
| Löslichkeit | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)28.35 kJ/mol at 25 °CSoluble in ether, chloroformmiscible with ethanolIn water, 230,000 mg/L at 25 °CSolubility in water, g/100ml at 20 °C: 30 (good)30%300g/l, 25% soluble in water, miscible with alcohol, Propylene glycol, Glycerin and oils.300 G/L (20 ºC) |
| Flammpunkt | -26 °F (NTP, 1992)-2 °F-2 °F (-19 °C) (Closed Cup)−16 °F |
| Siedepunkt | 88.7 °F at 760 mmHg (NTP, 1992)31.5 °C32 °C89 °F31.5 °C @760 [mm Hg]32-34 °C (lit.) |
| Schmelzpunkt | -100 °C (lit.) |
| Dampfdichte | 2.1 (vs air) |
| Dampfdruck | 32.91 psi ( 55 °C) |
| Brechungsindex | n20/D 1.343(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| Geruch | Pleasantagreeable. |
| pH | 4-5 (200g/l, H2O, 20℃) |
| Explosionsgrenze | 5-23%(V) |
| Geruchsschwelle | 130ppm |
| Biologische Quelle | synthetic |
| Geruchsart | fruity |
| Spezifische Wärmekapazität | Cp(liquid): 1.98 J/(g·K)Cp(gas): 1.07 J/(g·K), at 25℃ |
| Merck | 14,6077 |
| BRN | 1734623 |
| Henry-Konstante | 0.90 at 5.00 °C, 1.18 at 10.00 °C, 1.51 at 15.00 °C, 1.91 at 20.00 °C, 2.36 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005) |
| Dielektrizitätskonstante | 8.5(20℃) |
| Stabilität | Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point and very wide explosion limits. Incompatible with oxidizing agents. |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| InChI | 1S/C2H4O2/c1-4-2-3/h2H,1H3 |
| InChIKey | TZIHFWKZFHZASV-UHFFFAOYSA-N |
| SMILES | [H]C(=O)OC |
| LogP (Verteilungskoeffizient) | -0.21 at 25℃ |
| CAS Datenbank | 107-31-3(CAS DataBase Reference) |
| NIST chemische Informationen | Methyl formate(107-31-3) |
| EPA chemische Informationen | Methyl formate (107-31-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH224: Extremely 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 1.4% (11 of 764) of reports.H224 (98.6%): Extremely flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Formic acid, methyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Formic acid, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Formic acid, methyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 07-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/2054Formic acid, methyl ester: HSNO Approval: HSR001192 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, methyl ester: Environment tier I assessment |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Extremely 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 | Flammable liquid.Mixes with water. Flammable, irritating vapor is produced.Very dangerous fire hazard when exposed to heat or flame. |
| Gesundheitsgefahren | Inhalation causes irritation of mucous membranes. Prolonged inhalation can produce narcosis and central nervous symptoms, including some temporary visual disturbance. Contact with liquid irritates eyes and may irritate skin if allowed to remain. Ingestion causes irritation of mouth and stomach and central nervous system depression, including visual disturbances. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | TLV Basis is CNS impairment, upper respiratory tract irritation, and eye damage. In animal inhalation studies, narcosis, pulmonary edema, and death occur at concentrations in the range of 5000 ppm to 10,000 ppm for one to three hours of exposure. Human volunteers exposed to 100 ppm for 8 hours have increased fatigue. Foundry workers exposed to 36 ppm had no adverse effects. Methyl formate breaks down into methanol and formic acid. Formic acid causes optic neuropathy in cases of methanol poisoning. Exposure to methyl formate at 50 ppm is equivalent to methanol exposure at the TLV. [ACGIH] Intravenous doses of approximately 4g/kg cause significant methemoglobinemia in experimental dogs. [HSDB] No reported cases of toxic pneumonitis in humansMay cause slight skin irritation[CHEMINFO] A skin and eye irritant that causes CNS effects at high concentrations[ICSC] |
| DOT-Nummer und Handbuch | 1243 129 |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| EG-Einstufung | Symbol: F+, XnR: 12-20/22-36/37S: (2)-9-16-24-26-33 |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: I |
| Special Reports | EPA/Office of Pollution prevention and toxicsHigh production Volume (HPV) Challenge program's Robust summaries and Test Plans. Availible form: http://www.epa.gov/chemrtk/viewsrch.htm on Formates (December 2001) as of July 12, 2005.European Chemicals BureauIUCLID Dataset, Methyl formate (107-31-3) (2000 CD-ROM edition). Available from the database query page: http://ecb.jrc.it/esis/esis.php as of July 12, 2005. |
| 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. Rest. 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 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid:(General first aid procedures) |
| Sichere Lagerung | Fireproof. Separated from strong oxidants. Cool. |
| Firefighting Hazards | Vapors are heavier than air (vapor density, 2.07) and may travel to a source of ignition and flash back. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).50.0 [ppm] |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Do not extinguish unless flow can be stopped. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Do not use water on material itself.Water may be ineffective. /Use/ alcohol foam. |
| Lagerbedingungen | Store in cool, dry, well-ventilated location. Seperate from alkalis, oxidizing materials, and moisture. Outside or detached storage is prefered. |
| 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 reclaimed or collected and atomized in a suitable combustion chamber. |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Methyl formate may be disposed of by atomizing in a suitable combustion chamber. |
| Zielorgane | Eyes, respiratory system, central nervous system |
| Ökotoxizitätswerte | LC50 Leuciscus idus (Ide) about 120 mg/L/96 hrstatic /97.7% pure/EC50 Daphnia magna (Water fleaimmobilization) >500 mg/L/24 hr /Conditions of bioassay not specified in source examined/EC50 Scenedesmus subspicatus (Green algaecell multiplication inhibition) 240 mg/L/72 hr /Conditions of bioassay not specified in source examined/cell multiplication inhibition) 190 mg/L/96 hr /Conditions of bioassay not specified in source examined/EC50 Pseudomonas putida (aquatic bacteriacell multiplication inhibition) >10,000 mg/L/17 hr /Conditions of bioassay not specified in source examined/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a log Kow of 0.03(2) and a regression-derived equation(3), indicates that methyl formate is expected to have very high mobility in soil(SRC). Volatilization of methyl formate from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.2X10-4 atm-cu m/mole(4). Methyl formate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.9X10+2 mm Hg(5). Methyl formate is expected to undergo hydrolysis in moist soil. A base-catalyzed second-order hydrolysis rate constant of 16 L/mole-sec(SRC) was estimated using a structure estimation method(6)this corresponds to half-lives of 5.1 and 12 days at pH values of 7 and 8, respectively(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a log Kow of 0.03(2) and a regression-derived equation(3), indicates that methyl formate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.2X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.3 hours and 4.0 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is expected to be an important fate process for methyl formate. A base-catalyzed second-order hydrolysis rate constant of 16 L/mole-sec(SRC) was estimated using a structure estimation method(7)this corresponds to half-lives of 5.1 and 12 days at pH values of 7 and 8, respectively(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl formate, which has a vapor pressure of 5.9X10+2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl formate 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 71 days(SRC), calculated from its rate constant of 2.3X10-13 cu cm/molecule-sec at 25 °C(3). Methyl formate did not undergo direct photolysis when irradiated with UV light >300 nm(4). |
| Lebensmitteluntersuchungswerte | Methyl formate was detected in the volatiles of chicken, beef, and pork flavor(1). Methyl formate was identified as a volatile constituent in brewed, roasted, and dried coffee(2). It has also been detected as an aroma substance in apples(3). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Threshold /CNS depressant/ concentration to tadpoles (Rana pipiens): 240 mmol/L at room temperature. |
| Signs and Symptoms | Cough. Shortness of breath. Headache. Drowsiness.Redness.Redness. Pain.Sore throat. Further see Inhalation.irritation eyes, nosechest tightness, dyspnea (breathing difficulty)visual disturbancecentral nervous system depressionIn Animals: pulmonary edemanarcosis |
| Effluent Concentrations | The amount of methyl formate detected in exhaust gases from the combustion of various hydrocarbon fuels ranged from <0.1 to 0.7 ppm(1). |
| Soil Adsorption/Mobility | The Koc of methyl formate is estimated as 25(SRC), using a log Kow of 0.03(1)and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methyl formate is expected to have very high mobility in soil. |
| Natural Pollution Sources | Methyl formate was identified as an aroma substance in apples(1). |
| Atmospheric Concentrations | RURAL/REMOTE: Methyl formate was qualitatively detected in vapor-phase ambient air samples collected in the Kanawha Valley, WV in Sept 1977(1). |
| TSCA-Anforderungen | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methyl formate is included on this list. |
| Luftstandards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Methyl formate is produced, as an intermediate or final product, by process units covered under this subpart. |
| DHS Chemicals of Interest (COI) | Methyl formate110000Flammable chemical that can be released at a facility. |
| Berufliche Expositionsstufe (OEB) | A |
| Arbeitsplatzgrenzwert (OEL) | TWA: 100 ppm (250 mg/m3), STEL: 150 ppm (375 mg/m3) |
| Wassergefährdungsklasse (WGK) | 1 |
| Sofort lebensgefährliche Konzentration | 4,500 ppm |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1243 |
| Zollcode | 2915 13 00 |
| RTECS-Nr. | LQ8925000 |
| R-Sätze (R) | 12-20/22-36/37 |
| Toxizität | LD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rat > 4000 mg/kg |
| Gefahrensymbole | F+,Xn |
| Sicherheitshinweise (S) | 9-16-24-26-33 |
| Gefahrenklasse | 3Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Flam. Liq. 1STOT SE 1STOT SE 3 |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 107-31-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 842 °F |
Anwendungen & Verwendung
Beschreibung
Methyl Formate, also known as methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, it is a clear liquid with an ethereal odour, high vapor pressure, and low surface tension. It is an aromatic compound found in apples (Neubeller and Buchloh, 1986), and was identified as a volatile constituent in brewed, roasted, and dried coffee (Lovell et al., 1980); Methyl formate is used primarily to manufacture formamide, dimethylformamide, and formic acid. It is also used as a solvent for quick-drying finishes such as lacquers and in organic synthesis.
Verwenden
Methyl formate is used as a fumigant, as alarvicide for food crops, and as a solvent forcellulose acetate.