Brassylic acid

Structural formula
General
Surname	Brassylic acid
other names	Tridecanedioic acid; 1,11-undecanedicarboxylic acid;
Molecular formula	C 13 H 24 O 4
Brief description	crystalline, beige, odorless solid
External identifiers / databases
EC number	208-011-4
ECHA InfoCard	100.007.284
PubChem	10458
Wikidata	Q2099072
properties
Molar mass	244.33 g mol −1
Physical state	firmly
density	1.15 g cm −3 (25 ° C)
Melting point	108-113 ° C
boiling point	250 ° C (63.9 hPa)
solubility	practically insoluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 319-412
	P: 305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Brassylic acid , also tridecanedioic acid or 1,11-undecanedicarboxylic acid , is a dicarboxylic acid and belongs to its homologous series .

Extraction and presentation

Brassylic acid can be obtained together with pelargonic acid by ozonolysis of erucic acid . On an industrial scale, mutants of Candida tropicalis are used to extract brassylic acid from tridecane .

use

Brassylic acid can be used to make plastics. To do this, it undergoes reductive amination . The diamine can then be polymerized to nylon 13,13 with equal proportions of brassylic acid .

Ethylene brassylate, an ethylene glycol diester of brassylic acid, is also used in the food and cosmetics industries. The macrocyclic compound smells sweet like musk and can be found e.g. B. under the name Musk T in trade.

safety instructions

The acid can cause serious eye irritation, so eye protection is required. It is also assigned to water hazard class 1.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tridecanedioic acid in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ Peter Kurzweil, Paul Scheipers: Chemistry. Basics, advanced knowledge, applications and experiments . Vieweg + Teubner, Wiesbaden 2010, ISBN 978-3-8348-0341-2 , pp. 272 ( limited preview in Google Book search).
↑ Ronald D. Klein, M. Anne Favreau: The Candida Species. Biochemistry, Molecular Biology, and Industrial Applications . In: YH Hui, George G. Khachatourians (Eds.): Food Biotechnology. Microorganisms . Wiley-VCH, 1995, ISBN 978-0-471-18570-3 , pp. 320 f . ( limited preview in Google Book search).
↑ Albrecht Weiss: Selective Microbial Oxidations in Industry. Oxidations of Alkanes, Fatty Acids, Heterocyclic Compounds, Aromatic Compounds and Glycerol Using Native or Recombinant Microorganisms . In: Rolf D. Schmid, Vlada Urlacher (Ed.): Modern Biooxidation. Enzymes, Reactions and Applications . Wiley-VCH, 2007, ISBN 978-3-527-61153-9 , pp. 197 ( limited preview in Google Book search).
↑ Elmar W. Weiler, Lutz Nover: General and molecular botany . Thieme, Stuttgart 2008, ISBN 978-3-13-152791-2 , p. 326 ( limited preview in Google Book search).
↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . 6th edition. CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 573 f . ( limited preview in Google Book search).
↑ Wolfgang Legrum: Fragrances, between stench and fragrance. Occurrence, properties and application of fragrances and their mixtures . 2nd Edition. Springer, 2015, ISBN 978-3-658-07310-7 , pp. 170 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tridecanedioic acid in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Pohling-2] Peter Kurzweil, Paul Scheipers: Chemistry. Basics, advanced knowledge, applications and experiments . Vieweg + Teubner, Wiesbaden 2010, ISBN 978-3-8348-0341-2 , pp. 272 ( limited preview in Google Book search).

[3] Ronald D. Klein, M. Anne Favreau: The Candida Species. Biochemistry, Molecular Biology, and Industrial Applications . In: YH Hui, George G. Khachatourians (Eds.): Food Biotechnology. Microorganisms . Wiley-VCH, 1995, ISBN 978-0-471-18570-3 , pp. 320 f . ( limited preview in Google Book search).

[4] Albrecht Weiss: Selective Microbial Oxidations in Industry. Oxidations of Alkanes, Fatty Acids, Heterocyclic Compounds, Aromatic Compounds and Glycerol Using Native or Recombinant Microorganisms . In: Rolf D. Schmid, Vlada Urlacher (Ed.): Modern Biooxidation. Enzymes, Reactions and Applications . Wiley-VCH, 2007, ISBN 978-3-527-61153-9 , pp. 197 ( limited preview in Google Book search).

[Botanik-5] Elmar W. Weiler, Lutz Nover: General and molecular botany . Thieme, Stuttgart 2008, ISBN 978-3-13-152791-2 , p. 326 ( limited preview in Google Book search).

[6] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . 6th edition. CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 573 f . ( limited preview in Google Book search).

[7] Wolfgang Legrum: Fragrances, between stench and fragrance. Occurrence, properties and application of fragrances and their mixtures . 2nd Edition. Springer, 2015, ISBN 978-3-658-07310-7 , pp. 170 ( limited preview in Google Book search).