Sebacic acid

Structural formula
General
Surname	Sebacic acid
other names	Decanedioic acid 1,8-octanedicarboxylic acid
Molecular formula	C 10 H 18 O 4
Brief description	white, fine crystalline powder with a fatty acid odor
External identifiers / databases
CAS number 111-20-6 EC number 203-845-5 ECHA InfoCard 100.003.496 PubChem 5192 ChemSpider 5004 DrugBank DB07645 Wikidata Q413454
properties
Molar mass	202.25 g mol −1
Physical state	firmly
density	1.21 g cm −3
Melting point	131-134 ° C
boiling point	295 ° C (133 hPa)
Vapor pressure	1.3 h Pa (183 ° C)
solubility	poor in water (1 g l −1 at 20 ° C)
Refractive index	1.422 (133 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
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

In chemistry, sebacic acid (decanedioic acid, 1,8-octanedicarboxylic acid, HOOC (CH ₂ ) ₈ COOH) belongs to the homologous series of dicarboxylic acids . Their salts and esters are called sebacates.

It lies between azelaic acid and undecanedioic acid . The diesters with 2-ethylhexanol and 1-butanol are used as plasticizers for plastics , such as the dibutyl sebacate . Sebacic acid, and especially its dichloride, react with hexamethylenediamine (1,6-diaminohexane) to form a polyamide , nylon 6.10 (or PA 6.10).

Manufacturing

Sebacic acid is primarily obtained by alkaline cleavage of ricinoleic acid with sodium hydroxide or, on an industrial scale, directly from castor oil (contains about 87% ricinoleic acid). This reaction leads to sodium sebacate , which is worked up to sebacic acid, and 2-octanol as a by-product.

The synthesis of sebacic acid via Kolbe electrolysis by dimerizing decarboxylation of monomethyl adipate to dimethyl sebacate is also of technical importance . In addition, sebacic acid can be produced via the oxidation of stearic acid or 1,10-decanediol and via fermentation processes.

use

Sebacic acid is used as a raw material for various products. The best-known application is its use in the production of polyamides , especially polyamide 6.10. Here, hexamethylene diamine (HMD) is reacted with the sebacic acid in order to obtain the plastic. The polyester obtained by polycondensation from sebacic acid and glycerine is used as a biologically compatible plastic for medical products in surgery and in research as a framework for 3D cell cultures.

The esters of sebacic acid are used in the plastics industry as plasticizers . The esters also serve as components of lubricants and as extenders; Due to their low toxicity , they are often used in packaging films.

Individual evidence

1. ↑ ^{a b c d} data sheet sebacic acid (PDF) from Merck , accessed on May 9, 2017.
2. ↑ ^{a b} Data sheet sebacic acid from AlfaAesar, accessed on February 21, 2010 ( PDF )(JavaScript required) .
3. ↑ Data sheet sebacic acid at Acros, accessed on February 21, 2010.
4. ↑ 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. 3-458.
5. ↑ ^{a b c d} Boy Cornils, Peter Lappe: Discarboxylic Acids, Aliphatic . In: Ullmann's Encyclopedia of Industrial Chemistry , Wiley-VCH, Weinheim 2005, doi : 10.1002 / 14356007.a02_143.pub2 .
6. ↑ Hans-Jürgen Arpe: Industrial Organic Chemistry: Significant preliminary and intermediate products. Wiley-VCH, Weinheim 2007; P. 263; ISBN 978-3-527-31540-6 ( limited preview in Google Book Search).
7. ↑ Ranja Rai, Marwa Tallawi, Alexandra Grigore, Aldo R. Boccaccini: Synthesis, properties and biomedical applications of poly (glycerol sebacate) (PGS): A review. Progress in Polymer Science , 37 (2012) 1051-1078, doi : 10.1016 / j.progpolymsci.2012.02.001 .