基本情報
- 標準SMILES
CCOC=O- InChIKey
WBJINCZRORDGAQ-UHFFFAOYSA-N- 分子式
- C3H6O2
- 平均分子量
- 74.08 g/mol
- 単同位体質量
- 74.03677943
概要
Ethyl formate appears as a clear colorless liquid with a pleasant odor. Flash point -4 °F. Less dense than water. Vapors heavier than air.
名称と識別子
- 優先名称
- Ethyl formate
- IUPAC
- ethyl formate
- 現地名
- ギ酸エチル
- 英語名
- Ethyl formate
- 分子式
- C3H6O2
- 分子量
- 74.08
名称と別名
名称をさらに表示
データベース識別子
- CAS
109-94-4- PubChem CID
- 8025
- DTXSID
DTXSID6040117- ChEMBL
CHEMBL44215、CHEMBL55595- ChEBI
CHEBI:52342- UNII
- 0K3E2L5553
- EC Number
- 203-721-0
- Nikkaji
- J1.971B
物性
構造計算による物性
- XLogP
- 0.5
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 2
- 重原子数
- 5
- 形式電荷
- 0
- 複雑度
- 26.1
実験および物理化学的性質
Pesticides
Insecticides
Active substance -> EU Pesticides database: Not approved
LogP
0.23
0.23
0.23
0.27
Density
0.922 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9168 @ 20 °C
CONVERSION FACTORS: 1 MG/L EQUIV TO 330 PPM; 1 PPM EQUIV TO 3.03 MG/CU M; DENSITY OF SATURATED AIR: 1.25 (AIR= 1)
Relative density (water = 1): 0.92
0.917-0.922
0.92
Color/Form
MOBILE LIQUID
WATER-WHITE LIQ
Colorless liquid.
物理化学的性質
- 融点
- -80 °C · -80 °C (lit.)
- 沸点
- 52 · 52-54 °C (lit.)
- 比重(密度)
- 0.921 g/mL · 0.921 g/mL at 20 °C (lit.)
- 蒸気密度
- 2.5 · 2.5 (vs air)
- 蒸気圧
- 15.16 psi · 15.16 psi ( 55 °C)
- 屈折率
- 20 · n20/D 1.359(lit.)
- FEMA
- 2434 · 2434 | ETHYL FORMATE
- 闪点
- 7 °F · 7 °F
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- アルコール、ベンゼン、エーテルと混和する (Hawley, 1981)
- 外見
- 液体
- 色
- クリア
- 臭い (Odor)
- 特性;心地よい芳香。
- 由来生物
- synthetic
- においのタイプ
- エーテル的な
- 臭気閾値(Odor Threshold)
- 2.7 ppm · 2.7ppm
- 爆発限界(explosive limit)
- 16 % · 16%
- 水溶解度
- 11 g/100mL · 11g/100mL(18℃)
- 比熱容量
- 2.02 J/ · Cp(liquid): 2.02 J/(g·K), at 25℃
- JECFA Number
- 26 · 26
- Merck
- 14 · 14,3807
- BRN
- 906769 · 906769
- Henry's Law Constant
- 0.097 · 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 · 8.4(6℃)
- 安定性
- 安定。非常に可燃性。空気と爆発性混合物を形成する可能性があります。引火点が低く、爆発限界が広いことに注意してください。強酸化剤、強塩基、強酸、硝酸塩とは相容れない。
- 主な用途
- 農業洗浄剤化粧品環境フレーバーそして香料食品および飲料パーソナルケア
- 化粧品成分の機能
- 香料
- InChI
- 1S/C3H6O2/c1-2-5-3-4/h3H,2H2,1H3
- InChIKey
- WBJINCZRORDGAQ-UHFFFAOYSA-N
- SMILES
- CCOC=O
- LogP
- 1.504 at · 1.504 at 25℃
- CAS データベース
- 109 · 109-94-4(CAS DataBase Reference)
- NISTの化学物質情報
- Formic acid, ethyl ester(109-94-4)
- EPAの化学物質情報
- Ethyl formate (109-94-4)
安全と法規制
GHS分類
GHS Classification
Danger
H225: 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.
Danger
H225 (99.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]
危険有害性情報
Regulatory Information
Chemical: Formic acid, ethyl ester
Status: Active Update: 30-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17274
Formic acid, ethyl ester: HSNO Approval: HSR001148 Approved with controls
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
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 stomach; may 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 irritant; Reported 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 May;33(5):439-53.] Inhalation of high concentrations causes drowsiness and unconsciousness; A skin, eye, and respiratory tract irritant; [ICSC]
DOT ID and Guide
1190 129
1190 129
安全と保護具
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)
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
100.0 [ppm]
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.
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.
毒性情報
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).
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 system; In 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 ... .
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 arrac; as 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).
法規制情報
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.
安全データ
- OEB
- A
- OEL
- TWA: 100 ppm (300 mg/m3)
- wgk
- 1
- IDLA
- 1,500 ppm
- tsca
- TSCA listed
- rtecs
- LQ8400000
- ridadr
- UN 1190
- 毒性
- LD50 orally in rats: 4.29 g/kg (Smyth)
- hs_code
- 29151300
- risk_code
- 11-20/22-36/37
- 化審法
- (2)-678
- 安衛法
- 57,57-2
- 消防法
- 危険物第4類第一石油類(非水溶性)
- hazard_code
- F,Xn
- safety_code
- 9-16-24-26-33
- hazard_class
- 3
- packing_group
- II
- 自然発火温度
- 851 °F
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2STOT SE 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 109-94-4(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
A MUCH STRONGER IRRITANT THAN ETHYL ACETATE, PROBABLY BECAUSE OF HYDROLYSIS TO FORMIC ACID.
Ethyl formate is metabolized by esterases in Streptomyces nitrificans.
Absorption, Distribution and Excretion
BECAUSE OF RELATIVELY GOOD SOLUBILITY IN PLASMA, ETHYL FORMATE PASSES READILY THROUGH THE PULMONARY ALVEOLI AND, DUE TO HIGH WATER SOLUBILITY, HAS A HIGH BLOOD-AIR DISTRIBUTION COEFFICIENT.
ETHYL FORMATE IS ABSORBED BY THE LUNGS AND THE GI TRACT; SLIGHT PENETRATION OF THE SKIN IS SAID TO OCCUR...
用途と製造
Uses
Used as flavoring agent, solvent for nitrocellulose, and reagent in organic synthesis; Also used as a fungicide/larvicide for tobacco, cereals, and dried fruit; [ACGIH]
Farming (Pesticides) [Category: Industry]
IN LACQUER INDUSTRY, IN ARTIFICIAL SILK MFR AS SOLVENT FOR CELLULOSE ACETATE; IN MFR OF SAFETY GLASS; IN SHOE INDUSTRY AS SOLVENT FOR CELLULOID
SOLVENT FOR OILS AND GREASES
FLAVOR FOR LEMONADE & ESSENCES; MFR OF ARTIFICIAL RUM & ARRAC; SOLVENT FOR NITROCELLULOSE; FUNGICIDE AND LARVICIDE; IN ORGANIC SYNTHESIS
ACETONE SUBSTITUTE; IN SYNTHETIC RESINS
U.S. Production
(1978) PROBABLY GREATER THAN 4.54X10+5 G
(1982) PROBABLY GREATER THAN 9.08X10+5 G
Methods of Manufacturing
ESTERIFICATION OF FORMIC ACID WITH ETHYL ALCOHOL IN THE PRESENCE OF SULFURIC ACID
/IT IS/...PREPARED BY ESTERIFICATION OF ETHYL ALCOHOL AND FORMIC ACID OR BY DISTILLATION OF ETHYL ACETATE & FORMIC ACID IN PRESENCE OF CONCN SULFURIC ACID.
Produced by carbonylation of ethanol with carbon monoxide...
Formulations/Preparations
AREGINAL.../IS/ MIXTURE OF METHYL FORMATE AND ETHYL FORMATE.
ASSAY: 95% MINIMUM.
GRADES: TECHNICAL; FCC.
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Formic acid, ethyl ester: ACTIVE
USE IN FOODS RESTRICTED TO 0.0015%.
NON-ALCOHOLIC BEVERAGES 9.4 PPM, ALCOHOLIC BEVERAGES 10 PPM, ICE CREAM, ICES, ETC 21 PPM, CANDY 50 PPM, BAKED GOODS 98 PPM, GELATINS AND PUDDINGS 0.35-11 PPM, CHEWING GUM 430 PPM.
OF DIRECT FOOD ADDITIVES: LIMITATIONS- SYNTHETIC FLAVOR.
応用分野
解説C3H6O2(74.08).HCOOC2H5.ギ酸エチルは,濃硫酸の存在下,ギ酸をエタノールでエステル化すると得られる.無色の液体.沸点54 ℃.d2040.917.n20D1.359.水,エタノール,有機溶媒に可溶.加水分解,引火(引火点-28 ℃)しやすいので,乾燥剤を入れて冷暗所に保存する.ホルミル化剤,殺菌,殺虫剤,フレーバーとして使われる.森北出版「化学辞典(第2版)
用途フレーバーとしての用途は広くピーチ、パイナップル、アップル、アプリコット、バナナ、ベリー、バター、ブランデー、ラムウイスキーに用いる
用途香味料原料、医薬品原料
説明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.
天然物の起源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.
使用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.
一般的な説明A clear colorless liquid with a pleasant odor. Flash point -4°F. Less dense than water. Vapors heavier than air.
使用用途ギ酸エチルは、パイナップルなどの果実系香料やウィスキー、ラム酒、ブランデーなどの洋酒のフレーバーとして、様々な用途で用いられています。純粋なギ酸エチルのみを高濃度で嗅うぐ、スーッとするや除光液のような匂いに感じます。
調製方法
製造方法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.
製造方法図3. ギ酸エチルの製造 ギ酸とエタノールを混合し、触媒を加えるとエステル化によってギ酸エチルが生成します。触媒としては濃硫酸などの強酸が用いられます。この反応ではからのH+が触媒として働くと同時に、生成する水が濃硫酸と水和して反応系から排除されるので、下の図の平衡がより右に移動します。
純化方法Free acid or alcohol is removed by standing the ester over anhydrous K2CO3, with occasional shaking, then decanting and distilling from P2O5. Alternatively, the ester can be kept over CaH2 for several days, then distilled from fresh CaH2. It cannot be dried with CaCl2 because it reacts rapidly with the ester to form a crystalline compound. [Beilstein 2 IV 23.]
上流・下流製品情報
上流原料
下流製品
補足説明
定義ChEBI: Ethyl formate is a formate ester resulting from the formal condensation of formic acid with ethanol. It has a role as a fumigant and a plant metabolite. It is a formate ester and an ethyl ester.
関連反応
関連ノート
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