Laurolactam

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Structural formula
Laurolactam
General
Surname Laurolactam
other names
  • Laurolactam
  • 12-Amino-dodecanoic acid lactam
  • 12-aminododecanolactam
  • Azacyclotridecan-2-one
  • 2-azacyclotridecanone
  • Cyclododecalactam
  • Dodecane-12-lactam
  • Dodecyl lactam
  • Laurinolactam
Molecular formula C 12 H 23 NO
Brief description

beige to colorless crystalline solid

External identifiers / databases
CAS number 947-04-6
EC number 213-424-8
ECHA InfoCard 100.012.204
PubChem 13690
Wikidata Q2043636
properties
Molar mass 197.32 g mol −1
Physical state

firmly

density

0.973 g cm −3 (20 ° C)

Melting point
boiling point

348 ° C at 1013 hPa

solubility
  • very heavy in water (0.223 g l −1 at 20 ° C)
  • soluble in dioxane, benzene, cyclohexane, cyclododecanone
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Laurolactam (mostly laurolactam in English ) is a macrocyclic lactam that is used as a monomer for polyamide 12 and as a comonomer for copolyamides.

Manufacturing

The in the oxidation of cyclododecane with air or oxygen in the presence of boric acid and transition metal salts, z. B. Cobalt (II) acetate , also known as an ol / on mixture, the cyclododecanol / cyclododecanone mixture is quantitatively dehydrated to cyclododecanone on a copper contact and this is converted with hydroxylamine to form cyclododecanone oxime. The oxime is rearranged to laurolactam in a Beckmann rearrangement in the presence of a strong acid.

Laurolactam synthesis

An alternative process subjects cyclododecane to photonitrosation with nitrosyl chloride in the presence of anhydrous hydrogen chloride . The resulting cyclododecanone oxime is extracted with concentrated sulfuric acid and rearranged to laurolactam by heating to 160 ° C. The overall yield (photonitrosation + Beckmann rearrangement) is up to 93% of theory. Laurinlactam is manufactured in Europe by Arkema and Evonik Industries and in Japan by a joint venture between Ems-Grivory and Ube Industries .

properties

Laurolactam is a practically water-insoluble, technical grade mostly beige colored and in the pure state (monomer quality with 99.9% purity) white crystalline solid, which in many organic solvents, z. B. 1,4-dioxane , benzene , cyclohexane , is soluble. Purification takes place conventionally by multi-stage distillation under reduced pressure. The combination of distillation and crystallization from solution or melt provides very pure laurolactam (> 99%). The hazard potential emanating from laurolactam is assessed as low.

use

The ring-opening polymerization of the monomer laurolactam initially proceeds with the addition of water in a prepolymerization at approx. 300 ° C under pressure to form a prepolymer , which in a subsequent polycondensation stage at normal or reduced pressure and temperatures of approx. 250 ° C to give higher molecular weight polyamide 12 ( PA 12: - [NH- (CH 2 ) 11 -CO] n -) reacts.

Polyamide12

Laurolactam is used as a comonomer together with ε-caprolactam for the production of copolyamide 6/12.

Individual evidence

  1. ↑ a b c d data sheet 12-amino-dodecanoic acid lactam from Sigma-Aldrich , accessed on February 1, 2014 ( PDF ).
  2. ↑ a b Entry on laurolactam in the GESTIS substance database of the IFA , accessed on February 1, 2014(JavaScript required) .
  3. ↑ a b GPS Safety Report: Dodecane-12-lactam
  4. ↑ a b c d OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Dodecane-12-lactam , accessed on November 4, 2014.
  5. ↑ a b T. Schiffer, G. Oenbrink: Cyclododecanol, Cyclododecanone, and Laurolactam. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim 2002, doi : 10.1002 / 14356007.a08_201 .
  6. ↑ a b H.-J. Arpe: Industrial Organic Chemistry. 6., completely revised Ed., Wiley-VCH Verlag, Weinheim, 2007, ISBN 978-3-527-31540-6 .
  7. ^ Douglass F. Taber, Patrick J. Straney: The Synthesis of Laurolactam from Cyclododecanone via a Beckmann Rearrangement . In: Journal of Chemical Education . tape 87 , no. December 12 , 2010, p. 1392-1392 , doi : 10.1021 / ed100599q ( PDF ).
  8. ↑ Patent US8309714 : Process for Producing laurolactam .. Published on November 13, 2012 , Applicant: Ube Industries, Ltd., Inventor: J. Kugimoto et al
  9. ^ Y. Furuya et al .: Cyanuric Chloride as a Mild and Active Beckmann Rearrangement Catalyst. In: J.Am.Chem.Soc. 127, No. 32, 2005, pp. 11240-11241, doi : 10.1021 / ja053441x
  10. ↑ Patent US6197999 : Photonitrosation of cyclododecane in chloroform in quasi-anhydrous medium .. Published on March 6, 2001 , applicant: Atofina, inventor: J. Ollivier, D. Drutel. ‌
  11. ↑ Patent US8399658 : Method for isolation of laurolactam from a laurolactam synthesis process stream. Published on March 19, 2013 , Applicant: Evonik Degussa GmbH, inventor A. Hengstermann et al ..
  12. ↑ Patent US5362448 : Continuous polymerization method of laurolactam and apparatus therefor. Published on November 8, 1994 , Applicant: Ube Industries, Ltd., Inventor: A. Kawakami et al
  13. ↑ Patent DE3730504 : Copolyamides containing caprolactam and laurolactam, process for the preparation thereof and use thereof for heat-sealing textiles. Published on March 16th, 1989 , Applicant: Atochem Werke GmbH, inventors E. De Jong et al ..