Caprolactone

• ε - lactone
• 6- Hydroxyhexansäurelacton
• 6- Hydroxycapronsäurelacton
• 6- caprolactone
• Hexanolactone
• 6- Hexanolid
• 2- oxepanone
• Hexanoic acid epsilon -lactone
• Caprolactone

Colorless liquid

Liquid

1.08 g · cm -3 ( 20 ° C)

-1.5 ° C

235 ° C.

1.3 Pa (20 ° C)

Miscible with water

1.463 at 20 ° C.

Risk

5990 mg · kg -1 ( LD50, Rabbit, transdermal)

Template: Infobox chemical / molecular formula search available

ε -caprolactone, ε - lactone or even caprolactone is a chemical compound of the substance group of lactones. It consists of a seven membered ring.

Representation

There are a number of possibilities for the synthesis of caprolactone known, can be subdivided into two groups. Firstly, the production starting from open-chain compounds, mostly derivatives of the hexane, on the other hand is possible, the ring expansion of ketones.

Starting from the open-chain compounds, for example, 6 -hydroxyhexanoic acid, 1,6-hexanediol or adipic acid are used.

On the basis of the cyclic compounds can be prepared by a caprolactone, Baeyer-Villiger oxidation of cyclohexanone with peracids, such as peracetic acid, perbenzoic acid or m -chloroperbenzoic acid. The oxidation can however also be accomplished by means of catalysts by oxygen.

Properties

Caprolactone is a colorless liquid which solidifies at -1.5 ° C and boils at 235 ° C. It has at 20 ° C has a dynamic viscosity of 6.67 mPa · s ‣ Your flash point is 127 ° C, their ignition temperature of 204 ° C. In the range of 1.2 to 9 per cent by volume, it forms explosive mixtures with air. At temperatures above 220 ​​° C it begins to decompose.

Use

Caprolactone is used as a raw material for the production of polycaprolactone, a plastic selected from the group of thermoplastics.

Caprolactone can be easily opened by Lewis acids or Brønsted acids, which enables the production of Hexanderivaten.