化工社化工社 化学情報印刷レポート · 研究参考用
ポリ(ビニルエチルエーテル)
エチルビニルエーテル · 2-エトキシエテン · ビニル(エチル)エーテル · エトキシエテン · エテニルエチルエーテル · エトキシエチレン · エチルエテニルエーテル · 3-オキサ-1-ペンテン
識別子と物理属性
| CAS No. | 109-92-2 |
|---|---|
| 分子式 | C4H8O |
| 平均分子量 | 72.11 g/mol |
| 単同位体質量 | 72.05751488 g/mol |
| SMILES | C=COCC |
| InChIKey | FJKIXWOMBXYWOQ-UHFFFAOYSA-N |
| PubChem CID | 8023 |
| ChEMBL | CHEMBL116745 |
| EC No. | 203-718-4 |
| DTXSID | DTXSID3029609 |
| 現地名 | エチルビニルエーテル |
化学・物理的性質
| XLogP | 1 |
|---|---|
| 極性表面積 | 9.2 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 2 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 24.8 |
| 物質分類 | Flammable agents - 4th degree |
| Polymers | Plastics & Rubber -> Other Monomers |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | log Kow = 1.04 |
| 密度 | 0.7589 at 68 °F (USCG, 1999) - Less dense than waterwill float0.7589 at 20 °CRelative density (water = 1): 0.80.754 @25 °C0.753 g/mL at 25 °C (lit.) |
| Viscosity | 0.3 mm²/s |
| Color/Form | Colorless liquidEther-like odor |
| 溶解度 | In water, 7800 mg/L at 25 °CIn water, 10000 mg/L at 37 °CSlightly soluble in carbon tetrachloridesoluble in ethanolmiscible in etherSolubility in water, g/l at 15 °C: 8.3 (slightly soluble)8.3g/リットル7.8g/L(25℃) |
| 引火点 | less than -50 °F (USCG, 1999)< -50 °F (< -46 °C) /closed cup/−50 °F |
| 沸点 | 96 °F at 760 mmHg (USCG, 1999)35.5 °C36 °C35.6 °C @760 [mm Hg]33 °C (lit.) |
| Decomposition | Hazardous decomposition products formed under fire conditions. - Carbon oxidesWhen heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | -175 °F (USCG, 1999)-115.8 °C-115 °C-116 °C (lit.) |
| 蒸気圧 | 560 hPa (20 °C) |
| 屈折率 | n20/D 1.376(lit.) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 液体 |
| 色 | 無色透明 |
| 臭い | nauseating-ethereal but sweet odor |
| 爆発限界 | 1.3-12.0%(V) |
| BRN | 605351 |
| ヘンリー定数 | 1.8×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。とても燃えやすい。強力な酸化剤とは相容れない。保管中に過酸化物が発生する場合があります。使用前に劣化がないか確認してください。 |
| InChI | 1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 |
| InChIKey | FJKIXWOMBXYWOQ-UHFFFAOYSA-N |
| SMILES | CCOC=C |
| LogP（分配係数） | 1.63 at 25℃ |
| CAS データベース | 109-92-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Ethene, ethoxy-(109-92-2) |
| EPAの化学物質情報 | Vinyl ethyl ether (109-92-2) |
化学的特性
Colorless liquid. Extremely reactive, can be polymerized in liquid or vapor phase. Slightly soluble in water (0.9% by weight). Commercial material contains inhibitor to prevent premature polymerization. Often stored underground to minimize vapor losses.
安全性と法規制
| GHS 分類 | DangerH225 (29%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 710 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H224: Extremely flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Ethene, ethoxy-Ethene, ethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethene, ethoxy- 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: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24588Vinamar: HSNO Approval: HSR004474 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.) |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | Behavior in Fire: Explosive hazard (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Vapour/air mixtures are explosive. |
| 火災の可能性 | Flammable liquid |
| 健康有害性 | INHALATION OR INGESTION: Excitement followed by unconsciousness and respiratory paralysis. CNS depression. EYES: May cause irritation and transient injury to cornea. SKIN: Prolonged contact can cause tissue defatting and dehydration leading to dermatitis. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes. |
| 有害性の概要 | A mild skin irritantCauses general anesthesia in inhalation lethal-concentration studies of mice[RTECS] May polymerize on heating or contamination and form unstable peroxides on exposure to oxygen[CAMEO] May cause CNS depression[ICSC] A skin and eye irritant that may cause transient corneal injuryMay cause reddening of skin if spilled and allowed to remain on clothesInhalation can cause CNS depressionHigh vapor concentrations may cause mild smarting of eyes and respiratory systemMay cause liver injury[CHRIS] Stabilized with 0.1% potassium hydroxideMay form explosive peroxidesA skin and strong eye irritantInhalation may cause unconsciousness and respiratory paralysis[Sigma-Aldrich MSDS] Vinyl ethyl ether, stabilized (UN1302) has warning of explosive polymerization[ERG 2016] See Butyl vinyl ether. |
| 輸送番号・ガイド（DOT） | 1302 127P |
| FDA 要件 | Vinyl ethyl ether is an indirect food additive for use only as a component of adhesives. |
| 反応性グループ | Ethers |
| UN 分類 | UN Hazard Class: 3UN Pack Group: I |
| Special Reports | Toxikologische Bewertung. Heidelberg, Berufsgenossenschaft der chemischen Industrie 263 (2000) |
| Reactivity Alerts | Highly Flammable |
| 消火 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)polymerization hazard]:Use foam, dry powder, carbon dioxide, water. In case of fire: keep drums, etc., cool by spraying with water. |
| 応急処置措置 | Fresh air, rest. Refer immediately for medical attention.Rinse and then wash skin with water and soap.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 immediately for medical attention. |
| 漏出応急措置 | · 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. |
| 応急処置 | Call a doctor.General First Aid: |
| 安全保管 | Fireproof. Separated from strong oxidants and acids. See Chemical Dangers. Cool. Keep under inert gas. Store only if stabilized. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | Alcohol Foam.Water May be Ineffective.To fight fire, use alcohol foam, foam, CO2, dry chemical.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Handle and open container with care. Air sensitive. |
| 清掃方法 | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)polymerization hazard]: |
| 処分方法 | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product. |
| 漏出処分 | Evacuate danger area! Consult an expert! Remove all ignition sources. Ventilation. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Wash away remainder with plenty of water. Then store and dispose of according to local regulations. |
| 相互作用 | Alkyl ether-degrading Rhodococcus sp. strain DEE5151, isolated from activated sewage sludge, has an activity for the oxidation of a variety of alkyl ethers, aralkyl ethers and dibenzyl ether. The whole cell activity for diethyl ether oxidation was effectively inhibited by 2,3-dihydrofurane, ethyl vinyl ether and glutaraldehyde. Glutaraldehyde of less than 30 uM inhibited the activity by a competitive manner with the inhibition constant, K(I) of 7.07+/-1.36 uM. The inhibition type became mixed at higher glutaraldehyde concentrations >30 uM, probably due to the inactivation of the cell activity by the Schiff-base formation. Structurally analogous ethyl vinyl ether inhibited the diethyl ether oxidation activity in a mixed manner with decreasing the apparent maximum oxidation rate, v(max)(app), and increasing the apparent Michaelis-Menten constant, K(M)(app). The mixed type inhibition by ethyl vinyl ether seemed to be introduced not only by the structure similarity with diethyl ether, but also by the reactivity of the vinyl ether with cellular components in the whole cell system.1. In rats, surgically anesthetized with Urethane, an increase in the depth of anesthesia upon administration of ethyl carbamate (Urethane), pentobarbitone sodium (Nembutal), thiopentone sodium (Intraval), althesin, ketamine, trichloroethylene, halothane, methoxyflurane, diethyl ether, ethyl-vinyl ether, cyclopropane, enflurane or chloroform resulted in a dose-dependent increase in the latency, the decrease in the amplitudes of the initial positive and negative components of the short latency cortical response to electrical stimuli applied to the forepaw. 2. The same changes were seen when starting from initially unanesthetized rats and anesthetizing them with Urethane. 3. With all the inhalational agents used, these changes lasted for as long as the administration except with nitrous oxide where the changes in the cortical response were transient. 4. The tranquilizing agents diazepam, chlordiazepoxide, and haloperidol showed no such action. Chloral hydrate and chlorpromazine, on the other hand, produced moderate changes in the evoked cortical response similar to those seen with the other anesthetic agents used.The effects of ten inhalational anesthetic agents on drug metabolism were studied in rats. Male Sprague Dawley-rats were exposed to below anesthetic concentrations of the test agents 7 hours a day for 1 to 7 days, or up to 15 days when nitrous-oxide was used. A single intraperitoneal injection of 125 milligrams per kilogram (mg/kg) hexobarbital, a sleep inducer, was given 20 to 22 hours after the last exposure to the anesthetic, and sleeping time was determined. Some animals were given an intraperitoneal injection of 50 mg/kg SKF-525-A, an inhibitor of hepatic microsomal enzyme activity, 30 minutes before the hexobarbital injection. Liver homogenates prepared from some rats pretreated with diethyl-ether or halothane were incubated with hexobarbital and assayed for O-demethylase activity and aniline-hydroxylase activity. Hexobarbital sleeping time was significantly reduced after a single 7 hour exposure to diethyl-ether, isopropyl-ether, fluroxene, enflurane, and Forane. Two exposures to halothane and ethyl-vinyl-ether were required to cause a significant reduction in sleeping time. Chloroform caused an increase in sleeping time after one exposure, no change with two or four exposures, and a decrease after five or more exposures. Nitrous-oxide and cyclopropane had no effect on hexobarbital sleeping time. SKF-525-A blocked the decrease in sleeping time caused by diethyl-ether and halothane. The rate of hydroxylation of hexobarbital and aniline by rat liver homogenates was increased by pretreatment with either diethyl-ether or halothane, but demethylase activity was increased only by diethyl-ether pretreatment. The authors conclude that exposure to inhalation anesthetics can enhance the ability of rats to metabolize drugs. ... |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that vinyl ethyl ether is expected to have very high mobility in soil(SRC). Volatilization of vinyl ethyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 515 mm Hg(3), and water solubility, 7800 mg/L(4). Vinyl ethyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. A 100% degradation using activated sludge in the OECD Guideline 302B (Inherent biodegradability: Zahn-Wellens/EMPA) test(4) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that vinyl ethyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.3X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 515 mm Hg(4), and water solubility, 7800 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.6 hours and 3.4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 2(SRC), from its log Kow of 1.04(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 100% degradation using activated sludge in the OECD Guideline 302B (Inherent biodegradability: Zahn-Wellens/EMPA) test(5) suggests that biodegradation is an important environmental fate process in water(SRC). Vinyl ethyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Vinyl ethyl ether is an olefin and olefins react with photooxidants in natural waters (such as hydroxyl, peroxy and singlet oxygen) exposed to sunlight with a half-life on the order of 25 days(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vinyl ethyl ether, which has a vapor pressure of 515 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase vinyl ethyl ether 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 5 hours(SRC), calculated from its rate constant of 7.79X10-11 cu cm/molecule-sec at 25 °C(3). Vapor-phase vinyl ethyl ether is also degraded in the atmosphere by reaction with ozone and nitrate radicals(SRC)the half-lives for these reactions in air is estimated to be 1.4 and 0.6 hours(SRC), calculated from respective rate constants of 2.0X10-16 and 1.40X10-12 cu cm/molecule-sec at 25 °C(3). Vinyl ethyl ether does not absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its vapour. |
| 毒性の概要 | IDENTIFICATION AND USE: Vinyl ethyl ether is a flammable liquid. It is used in proteomics research and organic synthesis. It was studied as an anesthetic agent in the 1950s. HUMAN STUDIES: Vinyl ethyl ether was studied in clinical trials to investigate whether it was suitable as an anesthetic. Some patients participating in these studies suffered complications (generalized convulsions due to hypercarbia and respiratory and circulatory depression as well as respiratory and cardiac arrest), which were attributed to overdosage. The degree of muscle relaxation obtained with this type of anesthesia was considered to be inadequate. Liver function tests conducted after several hours of anesthesia showed that hepatic function was not affected. Urinalyses, blood counts and electrocardiograms obtained after anesthesia revealed slight, reversible changes in some cases. There is a report of one case of transient damage to the human cornea, which was reversible after 48 hr. ANIMAL STUDIES: In rabbits, it caused only very mild irritation to the skin and eye. On acute oral administration, dermal application and inhalation exposure, vinyl ethyl ether was found to be of low toxicity. A rapid induction of CNS depression and rapid recovery from narcosis was noted with monkeys, dogs, rats. The clinical signs of intoxication were characterized by the CNS depressant effect of the substance. In the Salmonella/microsome assay, vinyl ethyl ether was found to test negative both with and without metabolic activation. In the sister chromatid exchange assay in Chinese hamster ovary cells, the chemical caused a significant increase in sister chromatid exchange rate. |
| Signs and Symptoms | Cough. Incoordination. Dizziness. Drowsiness. Headache. Wheezing. Unconsciousness.Redness. Dry skin.Aspiration hazard! Headache. Nausea. |
| Effluent Concentrations | Vinyl ethyl ether has been detected in emissions from turbine engines(1). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of vinyl ethyl ether can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that vinyl ethyl ether is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ ... /CNS depression/ was also studied in one human subject. The induction period was 60 seconds, duration of light anesthesia was 6 minutes. Recovery was rapid and uneventful. Blood pressure and pulse were not altered. The subject stated that the vapors did not irritate the upper respiratory tract./HUMAN EXPOSURE STUDIES/ In the 1950s, ethoxyethene was studied in clinical trials to investigate whether it was suitable as an anesthetic. Some patients participating in these studies suffered complications (generalized convulsions due to hypercarbia and respiratory and circulatory depression as well as respiratory and cardiac arrest), which were attributed to overdosage. The degree of muscle relaxation obtained with this type of anesthesia was considered to be inadequate. Liver function tests conducted after several hours of anesthesia showed that hepatic function was not affected. Urinalyses, blood counts and electrocardiograms obtained after anesthesia revealed slight, reversible changes in some cases./HUMAN EXPOSURE STUDIES/ The pharmacological effects were studied in 29 patients, aged 14 to 58 years (7 males, 22 females). Gynecological and orthopedic cases prevailed. Ethyl vinyl ether (EVE) was used in combination with other common anesthetics. In brief, findings were as follows: Liver function was unchanged in 58% of the patients. Bromsulphthalein excretion was observed in some cases. In two of these, large doses up to 110 mL EVE had been used. Urinalysis: no changes were noted in 68% of the patients. Six patients (20%) showed findings (traces of acetone (n=6), increased sugar (n=2), traces of albumin (n=3) which had returned to normal on day 5 post treatment. Blood: no changes in 82% of the patientsthe remainder showed slight leucocytosis. ECG: no change in 48% of the patients. Tachycardia, auricular and ventricular premature contractions were all seen. Mild myocardial depression was noted in 5 cases (17%). Nausea, vomiting: was seen in 10 out of 29 patients. Salivation: was quite severe at timeswas treatable with atropine./CASE REPORTS/ There is a report of one case of transient damage to the human cornea, which was reversible after 48 hr./OTHER TOXICITY INFORMATION/ A rapid induction of /CNS depression/ and rapid recovery from narcosis was noted with monkeys, dogs, rats, and man. Compared with diethylether approximately 50% less the quantity was required. |
| Artificial Pollution Sources | Vinyl ethyl ether's production and use in copolymerizations and as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). Vinyl ethyl ether is released to air in emissions from turbine engines(2). Vinyl ethers are released to the atmosphere entirely from anthropogenic sources(3). |
| Environmental Biodegradation | AEROBIC: Using OECD Guideline 302B (Inherent biodegradability: Zahn-Wellens/EMPA Test) with an activated, non-adapted industrial sludge inoculum, vinyl ethyl ether, at 400 mg/L, reached 100% degradation (DOC removal) after 5 days of incubation. Using OECD Guideline 310 (Ready Biodegradability - CO2 in Sealed Vessels, Headspace Test) with a domestic activated sludge, the analog isobutyl vinyl ether, at 27.7 mg/L, reached 60-70% after 28 days of incubation(1)the interpretation of the test result was readily biodegradable, but failing the 10-day window(1). |
| Environmental Bioconcentration | An estimated BCF of 2 was calculated in fish for vinyl ethyl ether(SRC), using a log Kow of 1.04(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| DHS Chemicals of Interest (COI) | Vinyl ethyl ether110000Flammable chemical that can be released at a facility. |
| F | 19 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | KO0710000 |
| 輸送番号（UN） | UN 1302 (VINYL ETHYL ETHER, STABILIZED) |
| 毒性 | LD50 orally in Rabbit: 6120 mg/kg LD50 dermal Rabbit > 15000 mg/kg |
| 税関コード | 29091900 |
| 危険文句（R） | 12-19-36/37/38-11 |
| 化審法 | (2)-372 |
| 消防法 | 危-4-特-I |
| 危険表示 | F+,Xi,F |
| 安全措置（S） | 16-23-26-3/7-33-36-9 |
| 危険等級 | 3Aquatic Chronic 3Flam. Liq. 2STOT SE 3 |
| 包装等級 | I |
| 自然発火温度 | 178 °C |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 109-92-2(Hazardous Substances Data) |
用途
解説
エチルビニルエーテル (英: Ethyl Vinyl Ether) とは、特有のエーテル臭を有する無色の液体で、化学式 CH2CHOC2H5の有機化合物です。 別名として、エトキシエテン、ビニルエチルエーテル、3‐オキサ‐1‐などがあります。厚生労働省による職場の安全データシートや日本国内の大手試薬メーカーのウェブサイトでは、主に「エチルビニルエーテル」の名称が使用されています。 エチルビニルエーテルは、主にポリマーの原料や有機合成試薬、吸入麻酔として用いられています。エチルビニルエーテルの引火点は-45度と低く、容易に引火してしまうため、危険物第4類の特殊引火物に定められています。
用途
有機合成原料、ポリマー原料、吸入麻酔。
使用
Ethyl vinyl ether is used in fragrances, lubricating oil additives and spices preparation. It acts as an intermediate for sulfadiazine. It finds application in pharmaceuticals as anesthetics and analgesics. Further, it is used as a solvent in organic synthesis.
一般的な説明
A clear colorless low-boiling liquid (35-36°C) with an ether-like odor. Flash point below -50°F. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently. Less dense than water and slightly soluble in water. Hence floats on water. Vapors are heavier than air.
使用用途
エチルビニルエーテルは、主にポリマー合成における原料モノマー、有機化学反応における試薬、吸入麻酔として使われています。また、エチルビニルエーテルは、有機溶媒に溶けやすいことから塗料やの溶剤としても活用されています。 エチルビニルエーテルはビニル基構造を有しており、重合によってポリエチルビニルエーテルへと変換することが可能です。例えば、ブレンステッド酸またはルイス酸を触媒としてエチルビニルエーテルをカチオン重合することにより、ポリエチルビニルエーテルが得られます。ポリビニルエーテル類は、接着剤やインク材料、コーティング材料の原料です。 有機合成試薬としては、様々な有機化学反応の原料として使われています。また、エチルビニルエーテルは吸入麻酔としても使用されています。厚生労働省による職場の安全データシートによると、エチルビニルエーテルの吸入による外科麻酔濃度は6％です。
製法・合成法
製造方法
Ethyl vinyl ether (EVE) can be prepared by reacting acetylene with absolute ethanol in the presence of an alkali catalyst. The most commonly used catalyst for vinylation is an alkali metal hydroxide or an alkali metal alkoxide. In China, three processes for the manufacture of EVE using the acetylene route were used:A continuous process with a homogeneous catalyst under high pressure. The advantages of this process are fast reaction rate and high conversion, but the disadvantages include the requirement of high standard equipment, large energy consumption, and easy safety issues. A process with a solid catalyst (heterogeneous catalyst) under atmospheric pressure is relatively simple in product separation and refining compared with a process with a homogeneous catalyst under high pressure. However, it has the disadvantages of low output, the short service life of catalyst (about 110 h), and a high requirement on the specification of carrier lime.A process with a homogeneous catalyst under atmospheric pressure has the advantages of high output and good safety but disadvantages of low conversion.In the process with solid catalyst under atmospheric pressure, acetylene, and ethanol vapor were introduced into a fixed-bed reactor, and the vinylation reaction was carried out at a temperature as high as about 180 °C. EVE was produced with a concentration of about 70% in the outlet gas stream from the reactor. The fixed-bed reactor was charged with 4–5 mesh catalyst particles of potassium hydroxide supported on lime.
純化方法
It usually contains polymerization inhibitors (usually amines, e.g. triethanolamine) which can be removed by fractional distillation. Redistil it from sodium. [Beilstein 1 IV 2049.] LACHRYMATORY.