Ethylene glycol monoethyl ether

Structural formula
General
Surname	Ethylene glycol monoethyl ether
other names	2-ethoxyethanol ( IUPAC ); Ethyl glycol; Cellosolve, ethyl cellosolve; Glycol monoethyl ether; EGEE;
Molecular formula	C 4 H 10 O 2
Brief description	colorless, mild, almost odorless oily liquid
External identifiers / databases
EC number	203-804-1
ECHA InfoCard	100.003.459
PubChem	8076
ChemSpider	13836591
DrugBank	DB02249
Wikidata	Q209381
properties
Molar mass	90.12 g mol −1
Physical state	liquid
density	0.93 g cm −3 (20 ° C)
Melting point	−100 ° C
boiling point	135 ° C
Vapor pressure	5.06 h Pa (20 ° C); 9.30 hPa (30 ° C); 27.0 hPa (50 ° C);
solubility	miscible with water; miscible with all common organic solvents;
Refractive index	1.4054 (25 ° C)
safety instructions
H and P phrases	H: 226-302-331-360FD
	P: 201-210-304 + 340-308 + 310
Authorization procedure under REACH	of particular concern : toxic for reproduction ( CMR )
MAK	DFG : 2 ml m −3 or 7.5 mg m −3 ; Switzerland: 2 ml m −3 or 7.5 mg m −3 ;
Toxicological data	2130 mg kg −1 ( LD 50 , rat , oral ) ; 3300 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 monoethyl ether (according to IUPAC nomenclature: 2-ethoxyethanol , also known as ethyl glycol ) is an organic-chemical compound from the group of glycol ethers . It is a particularly valued, non-volatile solvent , which is mainly used in the paint industry .

Extraction and presentation

The large-scale production of ethyl glycol takes place by reacting ethylene oxide with ethanol at temperatures of 170-190 ° C and pressures of 10-15 bar. The process can be catalyzed either homogeneously with alkaline solutions such as sodium hydroxide or heterogeneously with aluminum oxide (Al ₂ O ₃ ).

Certain amounts of ethyl diglycol , ethyl triglycol and other oligomeric ethyl glycols are always formed as by-products . However, in order to reduce their formation, ethanol is usually used in large excess.

properties

Physical Properties

Ethylene glycol monoethyl ether has a relative gas density of 3.1 (density ratio to dry air at the same temperature and pressure ) and a relative density of the steam-air mixture of 1.01 (density ratio to dry air at 20 ° C and normal pressure ). The density is 0.93 g / cm ³ at 20 ° C. Ethyl glycol also has a vapor pressure of 5.06 hPa at 20 ° C, 9.3 hPa at 30 ° C and 27 hPa at 50 ° C. The evaporation rate (the time in which a substance evaporates completely in relation to the time it takes diethyl ether to evaporate) is 43. The electrical conductivity is rather low at 4.9 · 10 ⁻⁷ S · m ⁻¹ .

Chemical properties

Ethyl glycol is a flammable, medium to low volatility liquid from the group of glycol ethers . It can be mixed well with water in any ratio and with all common organic solvents . Ethyl glycol can form peroxides with air . In addition, violent reactions occur with strong oxidizing agents and light metals . An aqueous solution of ethyl glycol reacts neutrally at 20 ° C ( pH value at 7).

use

2-ethoxyethanol is an excellent solvent for cellulose nitrate , celluloid , ethanol-soluble resins , chlorinated rubber , polyvinyl acetates , polyvinyl butyrals , aldehyde and ketone resins , urea and melamine-formaldehyde resins , novolacs , resoles , alkyd and maleate resins , and polyacrylates . It also dissolves castor and linseed oil . It is also a widely used solvent in the paint industry . Due to its outstanding properties, it increases the blending ability in lacquer solutions and, because of its long evaporation time, can be used in numerous solvent mixtures whose high dissolving power ensures a clear lacquer film. Cleaning and paint stripping agents can also be added to ethyl glycol . Ethyl glycol is also a suitable solubilizer for emulsions of vegetable oils with water , which also increases the stability of these emulsions. It is also used as a solvent for natural and synthetic rubber , since ethyl glycol does not attack it.

safety instructions

The vapors of ethylene glycol can with air form when heated above the flash point an explosive mixture. 2-Ethoxyethanol is mainly absorbed through the respiratory tract and the skin . It is also very well absorbed through the digestive tract . Acute exposure to mild or moderate irritation to the skin and mucous membranes occurs . There is little acute inhalation and dermal toxicity . In oral poisoning particularly effects are the central nervous system on. More far-reaching consequences are metabolic disorders , changes in nerve function, as well as the influence on cardiovascular , liver and kidney functions . Long-term exposure can lead to chronic functional disorders of the blood and the blood-forming organs . A mutagenicity and a carcinogenicity can be ruled out, but is toxic to reproduction of a teratogenic effect expected. Animal experiments have also shown a teratogenic effect . Ethyl glycol has a lower explosion limit (LEL) of 1.8% by volume (67 g / m ³ ) and an upper explosion limit (UEL) of 15.7% by volume (590 g / m ³ ). The ignition temperature is 235 ° C. The substance therefore falls into temperature class T3 and explosion group IIB. The limit gap width was determined to be 0.78 mm. With a flash point of 40 ° C, ethyl glycol is considered flammable.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on ethylene glycol monoethyl ether in the GESTIS substance database of the IFA , accessed on April 13, 2019(JavaScript required) .
↑ ^a ^b entry on ethyl glycol. In: Römpp Online . Georg Thieme Verlag, accessed on April 13, 2019.
↑ 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. 3-234.
↑ Entry on 2-ethoxyethanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 13, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry in the SVHC list of the European Chemicals Agency , accessed on April 13, 2019.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 110-80-5 or 2-ethoxyethanol ), accessed on September 15, 2019.
↑ ^a ^b Hans-Jürgen Arpe: Industrial organic chemistry - important preliminary and intermediate products . 6th edition. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2007, ISBN 978-3-527-31540-6 , p. 176 .
↑ Technical rule for operational safety - TRBS 2153, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , as of April 2009, Jedermann-Verlag Heidelberg.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on ethylene glycol monoethyl ether in the GESTIS substance database of the IFA , accessed on April 13, 2019(JavaScript required) .

[RÖMPP-2] try on ethyl glycol. In: Römpp Online . Georg Thieme Verlag, accessed on April 13, 2019.

[CRC90_3_234-3] 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. 3-234.

[CLP_100.003.459-4] Entry on 2-ethoxyethanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 13, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[SVHC-5] Entry in the SVHC list of the European Chemicals Agency , accessed on April 13, 2019.

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 110-80-5 or 2-ethoxyethanol ), accessed on September 15, 2019.

[ARPE-7] Hans-Jürgen Arpe: Industrial organic chemistry - important preliminary and intermediate products . 6th edition. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2007, ISBN 978-3-527-31540-6 , p. 176 .

[8] Technical rule for operational safety - TRBS 2153, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , as of April 2009, Jedermann-Verlag Heidelberg.