11-Aminoundecanoic acid

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11-Aminoundecanoic acid
11-Aminoundecansäure Strukturformel.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.652
Properties
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[edit]

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):

Bromundecansäure.svg

Conversion of the bromide to the amine completes the synthesis:

Synthese von 11-Aminoundecansäure.svg

References[edit]

  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