11-Amino undecanoic acid

G. A. Sim. Acta Cryst. 8, 833-40 (1955). x-ray crystal structure of 11-amino-undecanoic acid hydrobromide hemihydratc. 

Production of 11-amino undecanoic acid. Economic data (France conditions, mid-1986)... 

Ricinoleate itself is a rich source of monomers for novel bio-based plastics (Fignre 6.2). The chemical bonds next to the hydroxyl group are susceptible to quantitative cleavage, producing an array of products depending on the chemistry of the reaction. The monomers produced include 11-amino undecanoic acid and sebacic acid, which are used to make Nylon 11 and Nylon 6,10, respectively [11]. 

The undecene methyl ester is saponified. The acid produced is converted to 11-bromoundecanoic acid in an anti-Markovnikov reaction under the influence of peroxides or light and hydrogen bromide. The bromoacid is converted to the ammonium salt of 11-amino undecanoic acid by ammonia and the free acid is liberated on lowering the pH. The free acid is polycondensed to polyamide (Nylon 11). 

Polyamide 11 is commercially produced by the polycondensation of 11-amino undecanoic acid, which is obtained from castor oil (see also Chapter 24). The monomer is also obtained by telomerization of ethylene and carbon... 

The heptanol (enanthol), which occurs on scission, is used for many different syntheses. The methyl undecylenate is saponified to the acid, to which hydrogen bromide is added across the double bond in an 02 initiated radical reaction to produce undecanoic acid. This is converted to 11-amino undecanoic acid by ammonolysis in aqueous dispersions, to which pure 11-bromoundecanoic acid can be added, since 10-bromoundecanoic acid cannot be ammonolyzed because of the secondary Br atom. Use of 3 kg of castor oil produces about 1 kg of nylon 11. 

Fig. 2.23. Separation of nucleotides by zwitterion-pair chromatography, showing pH effect. Packing material, ODS-Hypersil eluent, H20-MeOH (88 12, v/v), 75 mM in phosphate and 1.25 mM in 11-amino undecanoic acid (212)...

FIGURE 4.6 11-Amino undecanoic acid from methyl ricinoleate. 

Random poly(ester amide)s based on 11-amino undecanoic acid and e-caprolactone or lactic acid with amide contents of 40-75 mol% were prepared by solution polymerisation (Fig. 5.9(a)). XRD measurements showed a diffraction pattern very similar to the a form crystal of the nylon 11 homopolymer. A decrease of the crystallinity with increasing ester content is observed and which is most likely due to the insertion of e-caprolactoyl or lactyl units into the nylon 11 lattices. Such poly(ester amide)s with an ester/amide ratio of 40/60 have a typical microphase separated strueture, including an ester rieh phase, a middle phase composed of ester and amide segments and an amide rieh phase (Qian et al, 2003). 

This p. is based on - undecylenic acid, which derives from - castor oil and represents a p. of type II. Undecylenic acid is reacted with HBr in the presence of peroxides or air in, e.g., toluene at 30°C. 11-Bromo-undecanoic acid is formed in over 95% yield. Further reaction with 25% aqueous ammonia gives the desired 11-amino-undecanoic acid. Repeated crystallization enhances the pinity of the monomer. The polycondensation is carried out in a column with three zones melting, main reaction and equilibration of m.w. Phosphorous and phosphoric acids and their salts act as catalysts. The resulting p. (m.p. 190 °C) is very hydrophobic, has a low moisture content and is therefore used in electrical insulation. Other applications are as filament, powder - coatings and - molded goods. Castor oil consumption for this area was 35000 mt (1988). 

Two more polyamides based on co-amino acids were introduced into the markets after 1955, namely Nylon-11 (1955) and Nylon-12 (1966) [17]. Nylon-11 is produced by melt polycondensation of 11-amino undecanoic acid, which is... 

Rilsan, also known as nylon 11, has been manufactured in France by the self-condensation of to amino-undecanoic acid (NH,-—(CH,)io—COOH). 

Transformation of vegetable oils and fatty acids to sebacic acid and (o-amino-undecanoic acid. 

Nylon 11 was originally synthesized in France. The monomer, oa-amino-undecanoic acid, is obtained from methyl ricinoleate that comes from castor oil. Methyl ricinoleate is first cleaved thermally to heptaldehyde and methyl undecylenate ... 

When 1.88 was treated with n-butylamine and a rhodium catalyst, 1 l-(N-butyl-amino)undecanoic acid (1.267) was obtained. 51 This rhodium catalysis method allows an amine to add to an alkene in an anti-Markovnikov manner, as shown. The formation of 1.260 from the previous section also involves a rhodium species. 

Polyamide 11 and polyamide 12 are high performance materials. Polyamide 11 is produced by polymerisation of amino-undecanoic acid from castor oil. PA 12 is obtained from cmde oil by polycondensation of lauryllactam. 

FIGURE 4.2 Biomaterials from castor oil. From top left castor oil ricinoleic acid ricinoleyl-sulfate lithium grease Oithium hydroxystearate) 10-undecylenic add ll-amino-undecanoic acid. From top right dehydrated castor oil sebadc add. 

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