Sebacic acid

• Decanedioic
• 1.8 octanedicarboxylic

White fine crystalline powder with odor fettsäureartigem

Fixed

1.21 g · cm -3

131-134 ° C

295 ° C ( 133 hPa)

1.3 hPa ( 183 ° C)

Poorly in water (1 g · l-1 at 20 ° C)

1.422 ( 133 ° C)

Template: Infobox chemical / molecular formula search available

Sebacic acid ( decanedioic, 1,8- octanedicarboxylic, HOOC ( CH2) 8COOH ) belongs in chemistry for the homologous series of dicarboxylic acids. Their salts and esters are referred to as sebacates.

This places it between the azelaic acid and the undecanedioic. The diester with 2-ethylhexanol and 1-butanol are used as plasticizers for plastics, such as the dibutyl sebacate. Sebacic acid, and especially light her dichloride react with hexamethylene diamine (1,6- diamino hexane ) to give a polyamide, the nylon 6.10 ( or PA 6.10).

Production

Sebacic acid is mainly determined by alkaline cleavage of ricinoleic acid with sodium hydroxide or a large scale directly from castor oil ( containing about 87 % ricinoleic acid ) won. This reaction results in Natriumsebacat which is processed to sebacic acid, and 2 -octanol as a byproduct.

Also of technical importance is the synthesis of the sebacic acid via the Kolbe electrolysis by decarboxylation of dimerizing to Monomethyladipats dimethyl. Moreover, sebacic acid can be prepared via the oxidation of 1,10- decanediol, or stearic acid, as well as fermentation processes. About the ozonolysis of palmitic acid, a mixture of dicarboxylic acids, in which sebacic acid is included.

Use

Sebacic acid is used as a raw material for various products. The most known application is the use for the production of polyamides, especially the polyamide 6.10 (also known as nylon). Here hexamethylenediamine (HMD) is reacted with the sebacic acid, to obtain the plastic.

The esters of sebacic acid, used in the plastic industry as plasticizers, also serve as components of the esters as lubricants, and diluents; due to the low toxicity, they are often used in packaging films.