n -butyl vinyl ether

Structural formula
General
Surname	n -butyl vinyl ether
other names	Vinyl butyl ether; NBVE; Butyloxyethylene; 1- (ethenyloxy) butane;
Molecular formula	C 6 H 12 O
Brief description	colorless, volatile, highly flammable liquid with an ethereal odor
External identifiers / databases
EC number	203-860-7
ECHA InfoCard	100.003.510
PubChem	8108
Wikidata	Q1018214
properties
Molar mass	100.16 g mol −1
Physical state	liquid
density	0.78 g cm −3
Melting point	−113 ° C
boiling point	94 ° C
Vapor pressure	51 hPa (20 ° C); 65 hPa (25 ° C); 208 hPa (50 ° C);
solubility	poor in water (3 g l −1 at 20 ° C)
Refractive index	1.4005-1.4025
safety instructions
H and P phrases	H: 225-315-317
	EUH: 019
	P: 210-240-280-302 + 352-403 + 233
Toxicological data	10,000 mg kg −1 ( LD 50 , rat , oral )
	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

n -Butyl vinyl ether is a chemical compound from the group of enol ethers .

properties

Physical Properties

The compound is a colorless liquid that boils at 94 ° C under normal pressure . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in Torr, T in ° C) with A = 7.58994, B = 1524.9662 and C = 229.982 in the temperature range from 1.43 ° C to 115.96 ° C. Important thermodynamic quantities are given in the following table:

Compilation of the most important thermodynamic properties
property	Type	Value [unit]	Remarks
Standard enthalpy of formation	Δ _f H ⁰_liquid Δ _f H ⁰_gas	−215.8 kJ mol ⁻¹ −179.2 kJ mol ⁻¹	as a liquid as a gas
Enthalpy of combustion	Δ _c H ⁰_liquid	−3860.2 kJ mol ⁻¹	as a liquid
Heat capacity	c _p	231.8 J mol ⁻¹ K ⁻¹ (25 ° C) 2.31 J g ⁻¹ K ⁻¹ (25 ° C)	as a liquid
Critical temperature	T _c	540.5 K
Critical pressure	p _c	32.0 bar
Critical density	ρ _c	2.607 mol·l ⁻¹
Enthalpy of evaporation	Δ _V H	32.5 kJ mol ⁻¹	at normal pressure boiling point

It has a viscosity of 0.44 mPas (at 20 ° C).

Chemical properties

n -Butyl vinyl ether is chemically unstable at elevated temperatures. The measurement by means of differential thermal analysis shows exothermic decomposition above 240 ° C. It forms an explosive peroxide in air . Spontaneous polymerization is also possible in air , which means that it is usually offered in a stabilized form (e.g. with potassium hydroxide ).

Safety-related parameters

n -Butyl vinyl ether forms highly flammable vapor-air mixtures. The compound has a flash point of −12 ° C. The explosion range is between 1.2 vol.% As the lower explosion limit (LEL) and 8.6 vol.% As the upper explosion limit (UEL). The ignition temperature is 190 ° C. The substance therefore falls into temperature class T4

use

n -Butyl vinyl ether is used as a reactive diluent in hybrid radiation curing and as an intermediate product in the production of polyvinyl ether and other chemical compounds.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on butyl vinyl ether in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

↑ Entry on N- butyl vinyl ether at ChemBlink , accessed on February 25, 2011.

^ Yaws, CL: The Yaws Handbook of Vapor Pressure - Antoine Coefficients , Second Edition, Elsevier 2015, ISBN 978-0-12-802999-2 .

↑ ^a ^b ^c ^d ^e ^f ^g Steele, WV; Chirico, RD; Knipmeyer, SE; Nguyen, A .; Smith, NK: Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo [2.2.1] hept-2-ene, 5-vinylbicyclo [2.2.1] hept-2 -ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol in J. Chem. Eng. Data 41 (1996) 1285-1302, doi : 10.1021 / je960117w .

^ Schildknecht, CE; Zoss, AO; McKinley, C .: Vinyl alkyl ethers in Ind. Eng. Chem. 39 (1947) 180-186, doi : 10.1021 / ie50446a021 .

↑ BASF: MSDS (English) ( page no longer available , search in web archives ) Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. (PDF; 56 kB)@1@ 2

^ ^A ^b E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on butyl vinyl ether in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .