11-Aminoundecanoic acid

11-Aminoundecanoic acid

Identifiers
CAS Number	2432-99-7
3D model (Jmol)	Interactive image
ChemSpider	16168
ECHA InfoCard	100.017.652
PubChem	17083
InChI InChI=1S/C11H23NO2/c12-10-8-6-4-2-1-3-5-7-9-11(13)14/h1-10,12H2,(H,13,14) Key: GUOSQNAUYHMCRU-UHFFFAOYSA-N InChI=1/C11H23NO2/c12-10-8-6-4-2-1-3-5-7-9-11(13)14/h1-10,12H2,(H,13,14) Key: GUOSQNAUYHMCRU-UHFFFAOYAM
SMILES C(CCCCCN)CCCCC(=O)O
Properties
Chemical formula	C11H23NO2
Molar mass	201.31
Appearance	white solid
Density	1,1720 g·cm−3
Melting point	188–191 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

11-Aminoundecanoic acid is an organic compound with the formula H₂N(CH₂)₁₀CO₂H. This white solid is classified as an amine and a fatty acid. 11-Aminoundecanoic acid is a precursor to Nylon-11.^[1]

Preparation

As practiced by Arkema, 11-aminoundecanoic acid is prepared industrially from undecylenic acid, which is derived from castor oil.^[2] Undecylenic acid undergoes anti-Markovnikov hydrobromination in the presence of benzoylperoxide (BPO):

Conversion of the bromide to the amine completes the synthesis:

References

1. ↑ Ben Herzog, Melvin I. Kohan, Steve A. Mestemacher, Rolando U. Pagilagan and Kate Redmond "Polyamides" in Ullmann's Encyclopedia of Industrial Chemistry 2013, Wiley-VCH, Weinheim. doi:10.1002/14356007.a21_179.pub3
2. ↑ A. Chauvel, G. Lefebvre, Petrochemical Processes: Technical and Economic Characteristics, Band 2, S. 277, Editions Technip, Paris, 1989, ISBN 2-7108-0563-4