Glycidol

  • 2,3-epoxy -1-propanol
  • Oxirane- 2-methanol
  • Glycidol
  • Glycidyl alcohol
  • Glyceringlycid
  • 556-52-5 (racemate )
  • 57044-25-4 [( R)-isomer ]
  • 60456-23-7 [(S )-isomer ]

Colorless and odorless liquid

Liquid

1.1143 g · cm -3 ( racemate)

-54 ° C

162-163 ° C ( decomposition)

1.2 hPa (20 ° C)

  • Soluble in water, lower alcohols, ketones, ethers, benzene
  • Insoluble in aliphatic hydrocarbons

1.433 at 20 ° C.

Risk

Template: Infobox chemical / molecular formula search available

Glycidol is an organic chemical compound from the groups of epoxides ( oxiranes ) and the alcohols. The substance is a clear, odorless and tasteless liquid that reacts slowly with water to glycerol. The Glycidolmolekül is chiral and therefore occurs in two different mirror-image enantiomers.

Physical Properties

The rotation value for undiluted ( R) - ( )- glycidol is 15 °.

Production

Racemic glycidol can be obtained by dehalogenation and epoxide formation from 3-chloro -1 ,2-propanediol with bases.

Of allyl alcohol and tert- butyl hydroperoxide in the presence of catalytic amounts of vanadium ( IV) oxy - (acetylacetonate ) (VO (acac ) 2) can also be synthesized glycidol.

Also by oxidation of allyl alcohol with cumene hydroperoxide can be in a Sharpless epoxidation stereospecifically in the presence of titanium tetraisopropoxide or titanium tetraethoxide and diethyl tartrate as a chiral auxiliary selectively the (R) - or ( S)- enantiomer present.

Reactions

By reaction of the epoxy group of glycidol can undergo a variety of reactions with nucleophiles. With alcohols are formed via ring opening ether. Through the OH group can form both ester and ether.

Use

Glycidol is used as a stabilizer for vegetable oils and vinyl polymers and separation of emulsions. It is also used for the production of surfactants, pharmaceuticals, synthetic resins and finishing agents for textiles. Based on glycidol ethers and esters are used as epoxy resins and as reactive diluents in paints, adhesives and coatings for use.

Safety

In the presence of suitable catalysts glycidol can polymerize explosively. The substance is carcinogenic, severely irritating to the mucous membranes and skin caused by contact and by injury to the cornea eye damage. The central nervous system can be stimulated in a subsequent potential depression. In animal studies with rats and mice, glycidol was found to be genotoxic, carcinogenic and produced decreased fertility through to sterility.

In Baden- Württemberg glycidol fatty acid esters were found in edible vegetable oils such as palm oil that may arise in the refining process. This ester hydrolysis in the human digestive tract to fatty acids and glycidol. Therefore, the BfR advises against the use of palm oil -containing baby food.

Stereochemistry CAS registry number PubChem Vapor pressure Dangerous Substances Directive (67/548/EEC) Specific rotation 3-MCPD Titanium ethoxide Stabilizer (chemistry) Major depressive disorder CRC Handbook of Chemistry and Physics Beilstein database
269654
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