甲酸乙酯

Ethyl formate

HCID 8025CAS 109-94-4

基本信息

标准SMILES
CCOC=O
InChIKey
WBJINCZRORDGAQ-UHFFFAOYSA-N
分子式
C3H6O2
平均分子量
74.08 g/mol
单同位素质量
74.03677943

概述

Ethyl formate appears as a clear colorless liquid with a pleasant odor. Flash point -4 °F. Less dense than water. Vapors heavier than air.

名称与标识

首选名称
Ethyl formate
IUPAC
ethyl formate
中文名
甲酸乙酯
英文名
Ethyl formate
分子式
C3H6O2
分子量
74.08

名称与别名

ETHYL FORMATE109-94-4AreginalFormic acid, ethyl esterEthyl methanoateEthyl formic esterAethylformiatFormic etherEthylformiaatMrowczan etyluCarboxylic acid oxaethaneEthyle (formiate d')
展开更多名称
甲酸乙酯蚁酸乙酯甲酸乙烷基乙基甲酸酯天然甲酸乙酯甲酸乙酯CP甲酸乙酯超干甲酸乙酯/GC利扎曲坦杂质7甲酸(酯)乙烷基FORMIC ACID ETHYL ESTEREthyl forMatEthylformiatethyl formiateHCOOC2H5FEMA 2434
Etile (formiato di)FEMA No. 2434Ethyl ester of formic acidEthylester kyseliny mravenciDTXSID60401170K3E2L5553NSC-406578CHEBI:52342

数据库标识

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

性质

结构计算性质

XLogP
0.5
极性表面积
26.3 Ų
氢键供体
0
氢键受体
2
可旋转键
2
重原子
5

实验与物化性质

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Esters (<C12)
SpringerMaterials PropertiesCoriolis coupling
FragrancesFragrance Ingredient (Ethyl formate) -> IFRA transparency List
Pesticides · 2 条

Insecticides

Active substance -> EU Pesticides database: Not approved

LogP · 4 条

0.23

0.23

0.23

0.27

物理化学性质

熔点
-80 °C · -80 °C (lit.)
沸点
52 · 52-54 °C (lit.)
密度
0.921 g/mL · 0.921 g/mL at 20 °C (lit.)
蒸气密度
2.5 · 2.5 (vs air)
蒸气压
15.16 psi · 15.16 psi ( 55 °C)
折射率
20 · n20/D 1.359(lit.)
化学性质 · 1 条

无色透明液体,易挥发,有类似于乙酸乙 酯的特有的辣的刺激味和菠萝样的香气,还有强烈朗姆酒似香气,并略带苦味。 熔点-80℃,沸点53~ 54℃,相对密度0.917,折光率1.3597,自燃温度455℃,蒸气压26.6kPa (20.6℃)、40.0kPa(30.2℃)。能溶于约10份水中,并逐渐分解成游离酸和醇,能混溶于乙醇、乙醚、苯和丙二醇,微溶于矿物油和水(在水中逐渐分解),不溶于甘油,在碱性中容易水解成游离酸和乙醇。其化学结构上具有活泼羰基和酯基性质,有还原性,能进行酯缩合反应。易燃烧,蒸气可与空气形成爆炸性混合物,爆炸极限3.5%~16.5%(体积)。密闭并加氯化钙保存。甲酸乙酯可用于日化香精配方中,但主要用于食用香精配方中。

安全与法规

GHS分类

GHS Classification · 6 条

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]

危害信息

Regulatory Information · 4 条

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.)

Other Safety InformationIMAP assessments - Formic acid, ethyl ester: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 条

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 · 2 条

Burning Rate: 3.6 mm/min.

DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS.

Health Hazards · 2 条

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.

安全与防护

Fire Fighting · 2 条

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 · 4 条

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 · 2 条

· 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 · 3 条

Excerpt from NIOSH Pocket Guide for Ethyl formate:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants. Cool.
Firefighting HazardsVapor is heavier than air and may travel long distance to a source of ignition and flash back.

毒理信息

Target OrgansEyes, respiratory system, central nervous system
Environmental Fate · 3 条

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 ValuesEthyl 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 EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 条

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 · 5 条

Cough. Shortness of breath. Headache. Drowsiness.

Redness.

Redness. Pain.

Sore throat. Further see Inhalation.

irritation eyes, upper respiratory system; In Animals: narcosis

法规信息

FDA RequirementsSubstance added directly to human food affirmed as generally recognized as safe (GRAS).
FIFRA Requirements · 3 条

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.

安全数据

wgk
1
tsca
TSCA listed
毒性
LD50 orally in rats: 4.29 g/kg (Smyth)
RTECS号
LQ8400000
包装类别
II
危险等级
3
毒性防护 · 4 条

毒性ADI O~3(FAO/WHO,1994)。GRAS(FDA,§184.1295,2000)。LD50 1850mg/kg(大鼠,经口)。根据有关资料报道,甲酸乙酯对大鼠和豚鼠的急性口服LD50值有三个不同的测试结果,分别是4.29g/kg、1.85g/kg和1.11g/kg。

急性毒性口服- 大鼠 LD50: 1850 毫克/ 公斤

刺激数据皮肤- 兔子 460 毫克 轻度; 眼睛- 兔子 100 毫克/ 24 小时 中度

职业标准TWA 300 毫克/ 立方米; STEL 450 毫克/立方米

包装储运 · 4 条

爆炸物危险特性与空气混合可爆

可燃性危险特性遇明火、高温、氧化剂易燃; 燃烧产生刺激烟雾; 水中缓慢水解为甲酸和乙醇

储运特性库房通风低温干燥; 与氧化剂分开存放

灭火剂干粉、二氧化碳、泡沫、1211灭火剂

化学与工业

药理信息

Mechanism of ActionIt has been assumed, but not proved, that hydrolysis and release of formic acid on the moist surfaces are responsible for the irritant action of ethyl formate.
Metabolism/Metabolites · 2 条

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 · 2 条

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...

Cellular LocationsCytoplasm

用途与制造

Uses · 6 条

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 · 2 条

(1978) PROBABLY GREATER THAN 4.54X10+5 G

(1982) PROBABLY GREATER THAN 9.08X10+5 G

Methods of Manufacturing · 3 条

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 · 3 条

AREGINAL.../IS/ MIXTURE OF METHYL FORMATE AND ETHYL FORMATE.

ASSAY: 95% MINIMUM.

GRADES: TECHNICAL; FCC.

Use Classification · 4 条

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 条

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.

应用领域 · 4 条

用途用作硝基纤维素、醋酸纤维素的溶剂,医药上用于脲嘧啶、胞嘧啶、胸腺嘧啶的中间体。

用途用作色谱分析标准物质、溶剂及杀菌剂,也用于香精的配制、丙酮代用品

用途在日用化学品香精中偶尔用于修饰花香型,在食用香精中主要用于果香型如樱桃、杏子、桃子、草莓、悬钩子、苹果、凤梨、香蕉、梅子、葡萄等。在酒用中常用于朗姆、白兰地、威士忌和白葡萄等型中。

用途甲酸乙酯用作硝酸纤维素、乙酸纤维素等的溶剂,以及食品、香烟、谷类、干燥果品等的杀菌剂、杀幼虫剂和熏蒸剂。甲酸乙酯作为香精可用于调合桃子、香蕉、苹果、杏、菠萝、浆果等香气,亦可作为黄油、白兰地酒、甜酒、威士忌酒等的香料。甲酸乙酯也是有机合成的中间体。例如在制药工业,用于抗肿瘤药物富雪定、维生素B1的生产;甲酸乙酯与丙酮在甲醇钠-二甲苯溶液中缩合可得乙酰基乙烯醇钠,与乙酰甘氨酸酯缩合再与硫氰化钾环合可得2-巯基咪唑-4-羧酸乙酯。甲酸乙酯用于生产鱼腥草素、痛惊宁、康复龙、噻嘧啶、噻啶苯芥、利血生、全合成法山莨菪等的药物。

制备方法

生产方法1. 硫酸酯化法:由乙醇和甲酸在硫酸存在下加热酯化后,用五氧化二磷或无水氯化钙脱水精馏而得。将甲酸与乙酸乙酯在浓硫酸存在下共蒸馏也制得甲酸乙酯。2. 三氯化铝催化酯化法:由甲酸和乙醇在结晶三氯化铝催化剂存在下酯化而得。

试剂价格

A11113 · 500ml
甲酸乙酯, 98+% Ethyl formate, 98+% — 404元
42924 · 100ml
甲酸乙酯[用于分光光度测定法]Ethyl formate, 98+%, Extra Dry, AcroSeal™, Thermo Scientific Chemicals — 432元

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