Ethylvinylether
Ethoxyethene · EVE · VINYL ETHYL ETHER · Ethyl Vinyl Ethe · VINAMAR · ETHOXYETHYLENE · CH2=CHOC2H5 · ethoxy-ethen
Identifikatoren & physikalische Daten
| CAS No. | 109-92-2 |
|---|---|
| Summenformel | C4H8O |
| Durchschnittliche Molmasse | 72,11 g/mol |
| Monoisotopische Masse | 72,05751488 g/mol |
| SMILES | C=COCC |
| InChIKey | FJKIXWOMBXYWOQ-UHFFFAOYSA-N |
| PubChem CID | 8023 |
| ChEMBL | CHEMBL116745 |
| EC No. | 203-718-4 |
| DTXSID | DTXSID3029609 |
| Lokaler Name | Ethylvinylether |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 9,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 24,8 |
| Stoffklassen | Flammable agents - 4th degree |
| Polymers | Plastics & Rubber -> Other Monomers |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (Verteilungskoeffizient) | log Kow = 1.04 |
| Dichte | 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 |
| Löslichkeit | 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/l7.8 g/L (25 ºC) |
| Flammpunkt | less than -50 °F (USCG, 1999)< -50 °F (< -46 °C) /closed cup/−50 °F |
| Siedepunkt | 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. |
| Schmelzpunkt | -175 °F (USCG, 1999)-115.8 °C-115 °C-116 °C (lit.) |
| Dampfdruck | 560 hPa (20 °C) |
| Brechungsindex | n20/D 1.376(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| Geruch | nauseating-ethereal but sweet odor |
| Explosionsgrenze | 1.3-12.0%(V) |
| BRN | 605351 |
| Henry-Konstante | 1.8×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Highly flammable. Incompatible with strong oxidizing agents. May form peroxides in storage - check for their formation before use. |
| InChI | 1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 |
| InChIKey | FJKIXWOMBXYWOQ-UHFFFAOYSA-N |
| SMILES | CCOC=C |
| LogP (Verteilungskoeffizient) | 1.63 at 25℃ |
| CAS Datenbank | 109-92-2(CAS DataBase Reference) |
| NIST chemische Informationen | Ethene, ethoxy-(109-92-2) |
| EPA chemische Informationen | Vinyl ethyl ether (109-92-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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] |
|---|---|
| Regulatorische Informationen | 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.) |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | 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. |
| Brandpotenzial | Flammable liquid |
| Gesundheitsgefahren | 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. |
| Gefahrenübersicht | 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 |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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.