Phenoxyethanol

Structural formula
General
Surname	Phenoxyethanol
other names	2-phenoxy-1-ethanol 2-phenoxyethanol ( IUPAC ) Phenylcellosolve Phenyl glycol Monophenyl glycol Ethylene glycol monophenyl ether PHENOXYETHANOL ( INCI )
Molecular formula	C 8 H 10 O 2
Brief description	oily liquid with a faint aromatic odor and burning taste
External identifiers / databases
CAS number 122-99-6 EC number 204-589-7 ECHA InfoCard 100.004.173 PubChem 31236 ChemSpider 13848467 DrugBank DB11304 Wikidata Q418038
properties
Molar mass	138.16 g mol −1
Physical state	liquid
density	1.11 g cm −3
Melting point	14 ° C
boiling point	242 ° C
Vapor pressure	4 Pa (20 ° C)
solubility	little in water (24 g l −1 at 20 ° C)
Refractive index	1.534 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302-319 P: 305 + 351 + 338
MAK	DFG / Switzerland: 20 ml m −3 or 110 mg m −3
Toxicological data	1260 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

2-Phenoxyethanol (phenylglycol) is an organic compound . It is an ether of phenol with ethylene glycol with the empirical formula C ₈ H ₁₀ O ₂ .

properties

At room temperature, phenoxyethanol is a colorless, viscous liquid with a slightly aromatic, rose-like odor, which is sparingly soluble in water. The vapor pressure function results according to Antoine according to log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 5.13710, B = 2379.346 and C = −54.424 in the temperature range from 351 K to 518 K.

Extraction and presentation

Phenoxyethanol is made by reacting phenol with ethylene oxide .

INCI -compliant indication of the ingredients (including phenoxyethanol) of a cosmetic on the bottom of the back of the pack.

use

Phenoxyethanol has a bactericidal effect and is used in dermatological products such as B. skin cream, used as a preservative, for which the German Cosmetics Ordinance allows a concentration of up to 1%.
Phenoxyethanol is used to replace sodium azide in biological buffer solutions because it is less toxic and does not react with copper or lead . It is used as a narcotic for fish, which means it can be used to calm, anesthetize or euthanize fish, depending on the dosage. It is also used as a preservative for vaccines in the pharmaceutical industry and is found in most baby wipes and lubricants. Phenoxyethanol is also used as a solvent in inks, ballpoint pen pastes, printing pastes and stamp inks, as a fixative for perfumes and soaps, and for the manufacture of plasticizers and air fresheners.

Usage Restrictions

In the South Sea state of Palau , phenoxyethanol has been banned in sunscreens to protect coral reefs since January 2020. The ban is based on the results of a study published in 2017 on the pollution of the underwater world at Jellyfish Lake .

safety instructions

Phenoxyethanol mixed with methyldibromoglutaronitrile can trigger type 4 allergies ( allergic contact eczema ); The mixture known as MDBGN / PE is a frequent contact allergen with a 4% share of all allergies. Phenoxyethanol has a flash point of 121 ° C and only forms flammable vapor-air mixtures at higher temperatures. When reacting with oxygen, phenoxyethanol can form peroxides .

Individual evidence

1. ↑ Entry on PHENOXYETHANOL in the CosIng database of the EU Commission, accessed on June 22, 2020.
2. ↑ ^{a b c d e f g h i j k l} Entry on ethylene glycol monophenyl ether in the GESTIS substance database of the IFA , accessed on February 19, 2017(JavaScript required) .
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. 3-422.
4. ↑ Entry on 2-phenoxyethanol 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 122-99-6 or phenoxyethanol ), accessed on November 2, 2015.
6. ↑ ^{a b c d} Entry on 2-phenoxyethanol. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2011.
7. ↑ Stull, DR: Vapor Pressure of Pure Substances Organic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .
8. ↑ Baby wipes. Test J1301 at Öko-Test on January 11, 2013.
9. ^ The Republic of Palau Bans Sunscreen Chemicals to Protect its Coral Reefs and UNESCO World Heritage site - International Coral Reef Initiative. In: icriforum.org. November 4, 2018, accessed February 20, 2020 . 
10. ^ Coral Reef Research Foundation: Final Report - Sunscreen Pollution Analysis in Jellyfisch Lake , Palau, January 2017 ( PDF ).
11. ↑ G. Parmentier GmbH: Wool wax alcohols, a common contact allergen? (PDF; 21 kB) ( Memento of the original dated December 22, 2009 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. 
12. ^ White Paper Allergy in Germany. 2nd, updated and expanded edition; Ed .: German Society for Allergology and Clinical Immunology (DGAI), Association of German Allergologists (ÄDA), German Academy for Allergology and Environmental Medicine.
13. ^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.