Ethylene glycol monobutyl ether

Structural formula
General
Surname	Ethylene glycol monobutyl ether
other names	2-butoxyethan-1-ol ( IUPAC ); Butyl glycol; 1-butoxy-2-hydroxyethane; Ethylene glycol butyl ether; EGBE; BG;
Molecular formula	C 6 H 14 O 2
Brief description	colorless liquid with a slightly ethereal odor
External identifiers / databases
EC number	203-905-0
ECHA InfoCard	100.003.550
PubChem	8133
Wikidata	Q421557
properties
Molar mass	118.18 g mol −1
Physical state	liquid
density	0.90 g cm −3 (20 ° C)
Melting point	−75 ° C
boiling point	171 ° C
Vapor pressure	0.8 mbar (20 ° C)
solubility	miscible with water; miscible with organic solvents;
Refractive index	1.4198 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 302-331-315-319
	P: 261-270-280-301 + 312-302 + 352-305 + 351 + 338
MAK	DFG : 20 ppm, 98 mg m −3 ; Switzerland: 10 ml m −3 or 49 mg m −3 ;
Toxicological data	470 mg kg −1 ( LD 50 , rat , oral ) ; 220 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

Ethylene glycol monobutyl ether is a chemical compound from the group of glycol ethers .

Extraction and presentation

Ethylene glycol monobutyl ether can be obtained from ethylene oxide and n -butanol .

The annual production in Europe in 2003 was about 161,000 tons. This makes it one of the chemical substances that are produced in large quantities (" High Production Volume Chemical ", HPVC) and for which the Organization for Economic Cooperation and Development (OECD) collects data on possible dangers (" Screening Information Dataset ", SIDS).

properties

Ethylene glycol monobutyl ether is a colorless liquid with a slightly ethereal odor. It slowly reacts with atmospheric oxygen to form peroxides . In commercial products, 0.008-0.012% butylated hydroxytoluene is added to suppress the formation of peroxides.

Ethylene glycol monobutyl ether constitutes 79% water a constant boiling at 98.8 ° C azeotrope .

Glycol monoalkyl ethers are inert towards light metals such as aluminum or magnesium . However, slow superficial corrosion can be observed at the boiling point. A 10% addition of water suppresses aluminum corrosion and accelerates magnesium corrosion.

use

Ethylene glycol monobutyl ether is used as a solvent for printing inks, thinners , finishing agents and for the production of paints. In addition, it is used as a lubricant in hydraulic fracturing or as a solvent in the workover of oil production wells used. About 60% of the compound is used in Europe for paints and varnishes, about 11% is used in detergents and cleaning agents and up to 0.5% is used as a solvent in hair dyes. It is usually found in hair dyes in concentrations of less than 2%.

safety instructions

The vapors of ethylene glycol monobutyl ether can form an explosive mixture with air at high temperatures ( flash point 61 ° C, ignition temperature 240 ° C). The compound has low acute toxicity. Complete recovery was observed in humans after oral exposure to approximately 0.5 and 1.5 g / kg body weight and initially severe symptoms.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on ethylene glycol monobutyl ether in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b butyl glycol data sheet (PDF) from Merck , accessed on February 13, 2010.
↑ 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. 3-76.
↑ Entry on 2-butoxyethanol 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 .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 111-76-2 or ethylene glycol monobutyl ether ), accessed on November 2, 2015.
↑ ^a ^b OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for ethanol, 2-butoxy- , accessed on October 3, 2014.
↑ ^a ^b ^c ^d EU -Scientific Committee on Consumer Products: Opinion of the Scientific Committee on Consumer Products on ethylene glycol monobutyl ether , March 21, 2007, accessed on June 4, 2014
↑ Azeotrope named in BASF patent DE10056179, filed November 13, 2000 .
↑ C. Yoshimura, T. Ogura, "Corrosion Behavior of Aluminum and Magnesium in Ethers." in Keikinzoku 32: 443-450 (1982); Journal of Japan Institute of Light Metals; Note: It is unclear whether atmospheric oxygen was excluded in the study.
↑ Nachrichten aus der Chemie, 60, January 2012, pp. 31–34.
↑ ENVI: Effects of Shale Gas and Shale Oil Extraction on the Environment and Human Health

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on ethylene glycol monobutyl ether in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[merck-2] utyl glycol data sheet (PDF) from Merck , accessed on February 13, 2010.

[CRC90_3_76-3] 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. 3-76.

[CLP_100.003.550-4] Entry on 2-butoxyethanol 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 .

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 111-76-2 or ethylene glycol monobutyl ether ), accessed on November 2, 2015.

[SIDS-6] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for ethanol, 2-butoxy- , accessed on October 3, 2014.

[EU-7] EU -Scientific Committee on Consumer Products: Opinion of the Scientific Committee on Consumer Products on ethylene glycol monobutyl ether , March 21, 2007, accessed on June 4, 2014

[8] Azeotrope named in BASF patent DE10056179, filed November 13, 2000 .

[9] C. Yoshimura, T. Ogura, "Corrosion Behavior of Aluminum and Magnesium in Ethers." in Keikinzoku 32: 443-450 (1982); Journal of Japan Institute of Light Metals; Note: It is unclear whether atmospheric oxygen was excluded in the study.

[10] Nachrichten aus der Chemie, 60, January 2012, pp. 31–34.

[11] ENVI: Effects of Shale Gas and Shale Oil Extraction on the Environment and Human Health