HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl formate
FORMIC ACID ETHYL ESTER · ETHYL METHANOATE · Ethyl forMat · Ethylformiat · ethyl formiate · Areginal · HCOOC2H5 · FEMA 2434
Identifiers & Physical Properties
| CAS No. | 109-94-4 |
|---|---|
| Molecular formula | C3H6O2 |
| Average molar mass | 74.08 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 0.5 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 2 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 26.1 |
| Chemical classes | Flammable agents - 3rd degree |
| Solvents | Solvents -> Esters (<C12) |
| SpringerMaterials Properties | Coriolis coupling |
| Fragrances | Fragrance Ingredient (Ethyl formate) -> IFRA transparency List |
| Pesticides | InsecticidesActive substance -> EU Pesticides database: Not approved |
| LogP (partition coefficient) | 0.230.27 |
| Odor | Fruity odor.Characteristicpleasant aromatic. |
| Taste | SLIGHTLY BITTER TASTE |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 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.) |
| Flavoring agents | EU Flavoring substances |
| Color/Form | MOBILE LIQUIDWATER-WHITE LIQColorless liquid. |
| Melting point | -80 °C (lit.) |
| Boiling point | 52-54 °C (lit.) |
| Vapor density | 2.5 (vs air) |
| Vapor pressure | 15.16 psi ( 55 °C) |
| Refractive index | n20/D 1.359(lit.) |
| FEMA | 2434 | ETHYL FORMATE |
| FLAVIS Number | 09.072 | Ethyl formate |
| Flash point | 7 °F |
| Storage conditions | 2-8°C |
| Solubility | Miscible with alcohol, benzene, and ether (Hawley, 1981)11 g/100 mL (18 ºC) |
| Physical state | Liquid |
| Color | Clear |
| Biological source | synthetic |
| Odor type | ethereal |
| Odor threshold | 2.7ppm |
| Explosive limits | 16% |
| Thermal conductivity | 0.16 W/(m·K) at 25 ℃ |
| Specific heat capacity | Cp(liquid): 2.02 J/(g·K), at 25℃ |
| Sensitivity | Moisture Sensitive |
| JECFA Number | 26 |
| Merck | 14,3807 |
| BRN | 906769 |
| Henry's law constant | 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) |
| Dielectric constant | 8.4(6℃) |
| Exposure limits | ACGIH:TLV-STEL 100 ppm (303 mg/m3)OSHA:PEL-TWA 100 ppm (300 mg/m3)NIOSH:REL-TWA 100 ppm |
| Stability | 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. |
| Major applications | agriculturecleaning productscosmeticsenvironmentalflavors and fragrancesfood and beveragespersonal care |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C3H6O2/c1-2-5-3-4/h3H,2H2,1H3 |
| InChIKey | WBJINCZRORDGAQ-UHFFFAOYSA-N |
| SMILES | CCOC=O |
| LogP (partition coefficient) | 1.504 at 25℃ |
| CAS DataBase Reference | 109-94-4(CAS DataBase Reference) |
| SCOGS (Select Committee on GRAS Substances) | Ethyl formate |
| Substances Added to Food (formerly EAFUS) | ETHYL FORMATE |
| FDA 21 CFR | 184.1295 |
| EWG's Food Scores | 2 |
| FDA UNII | 0K3E2L5553 |
| NIST Chemistry Reference | Formic acid, ethyl ester(109-94-4) |
| EPA Substance Registry System | Ethyl formate (109-94-4) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H302+H332-H319-H360-H370-H373-H350-H335-H336-H225 |
| GHS precautionary statements | P501-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P308+P311-P303+P361+P353-P301+P312+P330-P304+P340+P312-P403+P233-P403+P235-P405 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves |
| Hazard symbols | F,Xn |
| Risk statements (R) | 11-20/22-36/37 |
| Safety statements (S) | 9-16-24-26-33 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 100 ppm (300 mg/m3) |
| UN transport number | UN 1190 |
| Water hazard class (WGK) | 1 |
| RTECS number | LQ8400000 |
| Autoignition temperature | 851 °F |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2STOT SE 3 |
| Packing group | II |
| Customs code | 29151300 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 109-94-4(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 4.29 g/kg (Smyth) |
| Immediately dangerous to life or health concentration | 1,500 ppm |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | 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] |
|---|---|
| Regulatory information | 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.) |
| Other safety information | IMAP assessments - Formic acid, ethyl ester: Human health tier I assessment |
| DOT label | Flammable Liquid |
| Fire hazards | 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. |
| Fire potential | Burning Rate: 3.6 mm/min.DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS. |
| Health hazards | 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. |
| Hazards summary | 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 ID and guide | 1190 129 |
| FDA requirements | Substance added directly to human food affirmed as generally recognized as safe (GRAS). |
| Reactive group | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| EC classification | Symbol: F, XnR: 11-20/22-36/37S: (2)-9-16-24-26-33 |
| UN classification | UN Hazard Class: 3UN Pack Group: II |
| Fire fighting | 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. |
| First aid measures | 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 . |
| 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 | Excerpt from NIOSH Pocket Guide for Ethyl formate:General First Aid:(General first aid procedures) |
| Safe storage | 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. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA).100.0 [ppm] |
| Fire fighting procedures | Dry chemical, ... carbon dioxide. |
| Storage conditions | KEEP TIGHTLY CLOSED & PREFERABLY IN CONTACT WITH CALCIUM CHLORIDE. |
| Cleanup methods | 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. |
| Nonfire spill response | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| 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.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. |
| Target organs | Eyes, respiratory system, central nervous systemRespiratory system |
| Environmental fate | 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). |
| Food survey values | 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). |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | 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 requirements | 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. |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 100 ppm (300 mg/m3) |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves |
| Water hazard class (WGK) | 1 |
| Immediately dangerous to life or health concentration | 1,500 ppm |
| TSCA inventory status | TSCA listed |
| RTECS number | LQ8400000 |
| UN transport number | UN 1190 |
| Customs code | 29151300 |
| Toxicity | LD50 orally in rats: 4.29 g/kg (Smyth) |
| Risk statements (R) | 11-20/22-36/37 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Hazard symbols | F,Xn |
| Safety statements (S) | 9-16-24-26-33 |
| Hazard class | 3Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2STOT SE 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H302+H332-H319-H360-H370-H373-H350-H335-H336-H225 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 851 °F |
| GHS precautionary statements | P501-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P308+P311-P303+P361+P353-P301+P312+P330-P304+P340+P312-P403+P233-P403+P235-P405 |
| Hazardous substances data | 109-94-4(Hazardous Substances Data) |
Applications & Uses
Description
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.
Uses
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.
General Description
A clear colorless liquid with a pleasant odor. Flash point -4°F. Less dense than water. Vapors heavier than air.
Preparation & Synthesis
Preparation
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.