11-Aminoundecanoic acid

January 2024 11-Aminoundecansäure Strukturformel.svg 11-Aminoundecanoic acid 2432-99-7 correct CAS correct FDA SFU34976HB 17083 16168 C(CCCCCN)CCCCC(=O)O 1/C11H23NO2/c12-10-8-6-4-2-1-3-5-7-9-11(13)14/h1-10,12H2,(H,13,14) GUOSQNAUYHMCRU-UHFFFAOYAM 1S/C11H23NO2/c12-10-8-6-4-2-1-3-5-7-9-11(13)14/h1-10,12H2,(H,13,14) GUOSQNAUYHMCRU-UHFFFAOYSA-N 11 23 1 2 White solid 1,1720 g·cm−3 188–191 11-Aminoundecanoic acid is an organic compound with the formula H2N(CH2)10CO2H. This compound is classified as an amine and a fatty acid. 11-Aminoundecanoic acid is a precursor to Nylon-11. 10.1002/14356007.a21_179.pub3 Polyamides Ullmann's Encyclopedia of Industrial Chemistry 2013 Herzog Ben Kohan Melvin I. Mestemacher Steve A. Pagilagan Rolando U. Redmond Kate 978-3-527-30385-4 11-Aminoundecanoic acid is a white crystalline and odorless solid with low solubility in water. Production As practiced by Arkema, 11-aminoundecanoic acid is prepared industrially from undecylenic acid, which is derived from castor oil.A. Chauvel, G. Lefebvre, Petrochemical Processes: Technical and Economic Characteristics, Band 2, S. 277, Editions Technip, Paris, 1989, 2-7108-0563-4. The synthesis proceeds in four separate reactions: Crude castor oil consists of about 80% triglycerides, from the ricinoleic acid, itself representing about 90% of the oil.https://onlinelibrary.wiley.com/doi/abs/10.1002/jsfa.2740020603 10.1002/jsfa.2740020603 The fatty acids and glycerides of castor oil 1951 Gupta S. S. Hilditch T. P. Riley J. P. Journal of the Science of Food and Agriculture 2 6 245–251 1951JSFA....2..245G subscription It is quantitatively transesterified with methanol to methyl ricinoleate (the methyl ester of ricinoleic acid) in the presence of the basic sodium methoxide at 80 °C within 1 h reaction time in a stirred reactor. left|300px|Rizinusöl-Umesterung The methyl ricinoleate is converted to heptanal and methyl undecenoate by combining with steam in a cracking furnace at 400 - 575 °C. The cleavage of the aliphatic chain occurs selectively between the hydroxymethylene and the allyl-methylene group. Besides heptanal and methyl undecenoate, a mixture of methyl esters of saturated and unsaturated C18-carboxylic acids is obtained. This mixture is known under the trade name Esterol and is used as a lubricant additive. left|400px|Pyrolyse von Ricinolsäuremethylester The methyl ester is next hydrolyzed to give 10-undecenoic acid (undecylenic acid). 600px The undecenoic acid is dissolved in toluene and, in the presence of the radical initiator benzoyl peroxide (BPO), gaseous hydrogen bromide is added, in contrary to the Markovnikov rule ("anti-Markovnikov"). When cooled to 0 °C, the fast and highly exothermic reaction produces 11-bromoundecanoic acid in 95% yield - the Markovnikov product 10-bromoundecanoic acid is produced in small quantities as a by-product. Toluene and unreacted hydrogen bromide are extracted under reduced pressure and reused. 600px 11-Bromodecanoic acid is mixed at 30 °C with a large excess of 40% aqueous ammonia solution. When the reaction is complete, water is added and the mixture is heated to 100 °C to remove the excess ammonia. 600px The acid can be recrystallized from water. For further purification, the hydrochloride of 11-aminoundecanoic acid, which is available by acidification with hydrochloric acid, can be recrystallized from a methanol/ethyl acetate mixture. Bulletin of the Korean Chemical Society 33 6 1873-1878 2012 Divergent Process for C10, C11 and C12 ω-Amino Acid and α,ω-Dicarboxylic Acid Monomers of Polyamides from Castor Oil as a Renewable Resource Koh, Moo-Hyun; Kim, Hyeon-Jeong; Shin, Na-Ra; Kim, Hyun-Su; Yoo, Dong-Won; and Kim, Young-Gyu 10.5012/bkcs.2012.33.6.1873 Use By acylation of 11-aminoundecanoic acid with chloroacetyl chloride, chloroacetylamino-11-undecanoic acid can be produced, which acts as a fungicide and insecticide. US 4055663 Halogenated acylamino acids as fungicides June 27, 1974 1977-10-25 Sol J. Barer et al., National Patent Development Corp. N-acyl derivatives of 11-aminoundecanoic acid in the form of oligomeric amides have remarkable properties as gelling agents for water and organic solvents. 10.1039/B307846A 11-Aminoundecanoic acid: A versatile unit for the generation of low molecular weight gelators for water and organic solvents 2004 d'Aléo Anthony Pozzo Jean-Luc Fages Frédéric Schmutz Marc Mieden-Gundert Gudrun Vögtle Fritz Caplar Vesna Zinic Mladen Chem. Commun. 2 190–191 14737543 Monomer for polyamide 11 By far the most important application of 11-aminoundecanoic acid is its use as a monomer for polyamide 11 (also: nylon-11). Wallace Carothers, the inventor of polyamide (nylon 66), is said to have polymerized 11-aminoundecanoic acid as early as 1931.Renewable Polymers: Synthesis, Processing, and Technology, edited by V. Mittal, J. Wiley & Sons, Hoboken, NJ, 978-0-470-93877-5 600px Although polyamide 11 is derived from a renewable raw material (i.e. biobased), it is not biodegradable. Nevertheless, it has the most advantageous ecological profile of comparable thermoplastics.Jim Mason: Rilsan Polyamide-11 - A success story for sustainable resource based engineering thermoplastics https://web.archive.org/web/20161204111934/http://oasys2.confex.com/acs/235nm/techprogram/P1170979.HTM December 4, 2016 , 9. April 2008. Due to its excellent toughness at low temperatures, polyamide 11 can be used at temperatures as low as −70 °C. Its relatively non-polar molecular structure due to the low frequency of amide bonds in the molecule results in low moisture absorption compared to polyamide 6 or polyamide 66. In addition, polyamide 11 has very good chemical stability, e.g. against hydrocarbons, low density, good thermal stability, weather resistance and is easy to process. References Category:Amino acids