Ethyl vinyl ether

Structural formula
General
Surname	Ethyl vinyl ether
other names	Vinyl ethyl ether; Agrisynth; Ethoxyethylene;
Molecular formula	C 4 H 8 O
Brief description	colorless liquid with an ethereal odor
External identifiers / databases
EC number	203-718-4
ECHA InfoCard	100.003.382
PubChem	8023
Wikidata	Q1371500
properties
Molar mass	72.11 g · mol -1
Physical state	liquid
density	0.75 g cm −3
Melting point	−115 ° C
boiling point	36 ° C
Vapor pressure	231 h Pa (0 ° C); 570 hPa (20 ° C); 1634 hPa (50 ° C);
solubility	8.3 g l −1 water at 15 ° C
Refractive index	1.3767 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 225
	P: 210-233-240-403 + 235
Toxicological data	8.16 ml kg −3 ( LD 50 , rat , oral )
Thermodynamic properties
ΔH f 0	−167.4 kJ / mol
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ethyl vinyl ether is an intermediate ( monomer ) in the manufacture of polymeric adhesives. Its previous experimental use as an anesthetic has been abandoned due to dosing complications.

Presentation and extraction

Ethyl vinyl ether is produced on an industrial scale by reacting acetylene ( ethyne ) with ethanol in the presence of strongly basic substances ( Reppesche vinylation reaction ). Temperatures between 150 and 180 ° C and high pressure promote the implementation. More than 1,000 tons of vinyl ethyl ether are produced annually (as of 1988).

properties

Vinyl ethyl ether is a colorless, volatile, flammable liquid with an ether-like odor that can polymerise spontaneously when heated. Solid potassium hydroxide , diethylamine , triethanolamine or hydroquinone are therefore added to the substance to stabilize it .

Safety-related parameters

Vinyl ethyl ether forms highly flammable vapor-air mixtures. The compound has a flash point below −45 ° C. The explosion range is between 1.7 vol.% (50 g · m ⁻³ ) as the lower explosion limit (LEL) and 28 vol.% (835 g · m ⁻³ ) as the upper explosion limit (UEL). The ignition temperature is 200 ° C. The substance therefore falls into temperature class T4.

use

In addition to the synthesis of adhesives, ethyl vinyl ether is also used in ring-opening metathesis polymerizations ( ROMP for short ) to detach the metal initiator (see Grubbs catalyst ) from the propagating chain end. By adding trifluoroacetyl chloride , 4-ethoxy-1,1,1-trifluoro-3-buten-2-one can be obtained.

toxicology

In animal experiments, the ethyl vinyl ether proves to be slightly toxic ( LD ₅₀ rat oral 8.16 ml / kg). The skin is only slightly irritated. The narcotic effect of vinyl ethyl ether only occurs at higher concentrations, but in individual cases cramps, respiratory and circulatory depressions up to respiratory and cardiac arrest can occur earlier. For this reason, its use as a narcotic in humans was discontinued.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on ethyl vinyl ether in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g ^h Toxicological assessment of vinyl ethyl ether (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-256.
↑ ^a ^b Entry on ethyl vinyl ether in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 19, 2016.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-26.
↑ Patent US8981115 : Process for the synthesis of halogenated cyclic compounds. Registered on April 29, 2013 , published on March 17, 2015 , applicant: Solvay SA, inventor: Max Braun. ‌
↑ EP 1 803 703 A1: “Halogenated alkenone ethers, for example 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (“ ETFBO ”), are building blocks in chemical synthesis. They can be prepared by reacting an acid chloride with a vinyl ether in the presence of a base; the base can also be used as a solvent in excess. "

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on ethyl vinyl ether in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[BGChem-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Toxicological assessment of vinyl ethyl ether (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

[CRC90_3_256-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-256.

[chemid-4] Entry on ethyl vinyl ether in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 19, 2016.

[CRC90_5_26-5] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-26.

[6] Patent US8981115 : Process for the synthesis of halogenated cyclic compounds. Registered on April 29, 2013 , published on March 17, 2015 , applicant: Solvay SA, inventor: Max Braun. ‌

[7] EP 1 803 703 A1: “Halogenated alkenone ethers, for example 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (“ ETFBO ”), are building blocks in chemical synthesis. They can be prepared by reacting an acid chloride with a vinyl ether in the presence of a base; the base can also be used as a solvent in excess. "