Di- n- butyl ether

Structural formula
General
Surname	Di- n- butyl ether
other names	Butyl ether (ambiguous); Dibutyl ether (ambiguous); 1-butoxybutane; 1,1'-oxybisbutane;
Molecular formula	C 8 H 18 O
Brief description	flammable, colorless liquid with a fruity odor
External identifiers / databases
EC number	205-575-3
ECHA InfoCard	100.005.069
PubChem	8909
Wikidata	Q1207808
properties
Molar mass	130.23 g mol −1
Physical state	liquid
density	0.77 g cm −3
Melting point	−95 ° C
boiling point	141 ° C
Vapor pressure	6.4 hPa (20 ° C); 45 hPa (50 ° C); 75 hPa (65 ° C);
solubility	very heavy in water (0.3 g l −1 at 25 ° C); miscible with most organic solvents;
Refractive index	1.398-1.399 (20 ° C)
safety instructions
H and P phrases	H: 226-315-319-335-412
	P: 210-273-305 + 351 + 338-302 + 352
Toxicological data	7400 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

Di- n -butyl ether is a chemical compound from the group of ethers , more precisely the dibutyl ether .

Extraction and presentation

Di- n -butyl ether can be prepared by condensation of 1-butanol with an acid ( sulfuric acid , hydrochloric acid ) as a catalyst are recovered.

Another possibility is the Williamson ether synthesis :

{\ displaystyle \ mathrm {CH_ {3} (CH_ {2}) _ {3} ONa + CH_ {3} (CH_ {2}) _ {3} Cl \ longrightarrow (CH_ {3} (CH_ {2})) _ {3}) _ {2} O + NaCl}}

properties

Di- n -butyl ether is a colorless liquid with a fruity or fish-like odor. Its odor threshold is 0.37 - 2.5 mg / m ³ . According to Antoine, the vapor pressure function results according to log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 3.93018, B = 1302.768 and C = −81.481 in the temperature range from 362 K to 413 K.

Safety-related parameters

Di- n -butyl ether forms highly flammable vapor-air mixtures. The compound has a flash point of 25 ° C. The explosion range is between 0.9% by volume (48 g / m ³ ) as the lower explosion limit (LEL) and 8.5% by volume (460 g / m ³ ) as the upper explosion limit (UEL). The limit gap width was determined to be 0.86 mm. This results in an assignment to explosion group IIB. The ignition temperature is 175 ° C. The substance therefore falls into temperature class T4.

use

Di- n -butyl ether is used as a solvent for Grignard reactions as well as fats, oils, organic acids, alkaloids and others. It also serves as a constituent for catalysts for (co) polymerizations and is used in the production of pesticides (e.g. cyhexatin ). Studies have shown suitability as a fuel or as a component of fuels.

literature

Luca Bernazzani, Maria R. Carosi u. a .: Thermodynamic study of organic compounds in di-n-butyl ether. Enthalpy and Gibbs energy of solvation. In: Physical Chemistry Chemical Physics. 2, p. 4829, doi : 10.1039 / B004804F .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on dibutyl ether in the GESTIS substance database of the IFA , accessed on July 5, 2019(JavaScript required) .
↑ ^a ^b ^c dibutyl ether (Wacker)
↑ Entry on dibutyl ether in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ di-n-butyl ether (Enius)
↑ J. Cidlinsky, J. Polak: Saturated Vapor Pressures of Some Ethers. In: Collect Czech Chem Commun . 34, 1969, pp. 1317-1321, doi: 10.1135 / cccc19691317 .
↑ ^a ^b ^c ^d E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ Entry on dibutyl ether. In: Römpp Online . Georg Thieme Verlag, accessed on July 5, 2019.
↑ Damyanov, Hofmann, Pichler, Schwaiger: "Biogenic ethers - production and use in diesel engine operation", Motortechnische Zeitschrift, January 2019

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on dibutyl ether in the GESTIS substance database of the IFA , accessed on July 5, 2019(JavaScript required) .

[wacker-2] utyl ether (Wacker)

[CLP_100.005.069-3] Entry on dibutyl ether in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[4] -n-butyl ether (Enius)

[5] J. Cidlinsky, J. Polak: Saturated Vapor Pressures of Some Ethers. In: Collect Czech Chem Commun . 34, 1969, pp. 1317-1321, doi: 10.1135 / cccc19691317 .

[Brandes-6] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[Roempp-7] Entry on dibutyl ether. In: Römpp Online . Georg Thieme Verlag, accessed on July 5, 2019.

[8] Damyanov, Hofmann, Pichler, Schwaiger: "Biogenic ethers - production and use in diesel engine operation", Motortechnische Zeitschrift, January 2019