Linalyl acetate

  • Essigsäurelinalylester
  • Ethansäurelinalyester
  • Linaloolacetat
  • (3,7- Dimethylocta -1 ,6- dien-3- yl ) acetate
  • Bergamiol

Colorless, pleasant -smelling bergamot liquid

Liquid

0.9 g · cm -3

<-20 ° C

220 ° C

1 mbar (20 ° C)

  • Sparingly soluble in water ( 1.34 g · l -1) and glycerol
  • Poorly in ethanol
  • Soluble in diethyl ether, diethyl phthalate, benzyl benzoate and mineral oil

Attention

13,900 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Linalyl acetate is a monoterpenoid ester with the molecular formula C12H20O2. It is a colorless liquid with a fresh, sweet smell.

According to ESIS, the substance is produced in high quantities ( " HPV Chemical ").

Occurrence

Linalyl acetate is found as a major component in lavender oil ( 30-60 %), the lavandin oil ( 25-50 %), the clary sage (up to 75 %) and bergamot oil ( 30-45 %) and comes in addition to many other essential oils.

Production and representation

Linalyl acetate can be obtained from the above-mentioned essential oils.

Synthetic can linalyl acetate by esterification of linalool win, being careful to mild reaction conditions, since linalool as the unsaturated tertiary alcohol tends to dehydrate and cyclization. Suitable synthetic routes starting from linalool would, for example, the reaction with Ethenon with boiling acetic anhydride while distilling off the produced acetic acid or a transesterification by means of acetic acid tert-butyl ester in the presence of sodium methoxide.

From Dehydrolinalool it can be obtained by esterification with acetic anhydride and subsequent partial hydrogenation.

Is also used in the reaction of β -pinene with acetic acid and sodium acetate in the presence of copper ( I) chloride, said linalyl acetate with a yield of 75-80 % is formed.

Use

Linalyl acetate is extensively used in perfumery. Due to its good stability in an alkaline environment, it is also often used in soaps or detergents.

Safety

The vapors of linalyl acetate can form (94 ° C, ignition temperature 225 ° C flash point) with air to form an explosive mixture.

CAS registry number PubChem Bergamot orange Vapor pressure Dangerous Substances Directive (67/548/EEC) European chemical Substances Information System Dehydration reaction Ethenone Digital Object Identifier
513548
de