25038-74-8Relevant articles and documents
Enzyme-catalyzed laurolactam synthesis via intramolecular amide bond formation in aqueous solution
Ladkau, Nadine,Hermann, Inna,Buehler, Bruno,Schmid, Andreas
, p. 2501 - 2510 (2011)
Lactam formation from ω-aminocarboxylic acids is thermodynamically unfavored in aqueous solution and therefore hard to achieve. In the present work ω-laurolactam hydrolases from Acidovorax sp. T31 and Cupriavidus sp. U124 were investigated regarding their potential to catalyze lactam formation. Both enzymes are known to hydrolyze laurolactam to 12-aminododecanoic acid. The ω-laurolactam hydrolase genes were expressed in Escherichia coli BL21 (DE3) and the catalytic activity of the respective proteins was investigated. As expected from thermodynamics, only laurolactam hydrolysis but not 12-aminododecanoic acid cyclization was observed in whole-cell biotransformations and cell extract assays. The utilization of 12-aminododecanoic acid methyl ester, as an activated form of 12-aminododecanoic acid, resulted in intramolecular amide bond formation with the product laurolactam. Maximum laurolactam formation rates of 13.5 and 14.3 U g CDW-1 and molar yields of 11.5% and 13.0% were achieved in biotransformations at pH 10 with recombinant E. coli harboring the ω-laurolactam hydrolase from Cupriavidus sp. U124 and Acidovorax sp. T31, respectively. Furthermore, it was shown that under the harsh reaction conditions applied, the utilization of whole-cell biocatalysts enables 17.2-fold higher laurolactam formation activity in comparison to free enzymes in solution. This study shows that hydrolase-catalyzed laurolactam synthesis can be achieved in aqueous solution by selection of an appropriate substrate and reaction pH. Copyright
In situ multinuclear solid-state NMR spectroscopy study of Beckmann rearrangement of cyclododecanone oxime in ionic liquids: The nature of catalytic sites
Blasco,Corma,Iborra,Lezcano-Gonzalez,Monton
, p. 78 - 83 (2010)
The Beckmann rearrangement of cyclododecanone oxime into ω-laurolactam has been investigated in four ionic liquids: 1-butyl-3-methylimidazolium hexafluorophosphate and tetrafluoroborate ([C4mim], [C4mim]), and 1-butyl-2,3-dimethylimidazolium and 1-butyl-4-methylpyridinium hexafluorophosphates ([C4mpyr], [C4m2im]), in a batch reactor as well as by 'in situ' multinuclear solid-state NMR spectroscopy. The Beckmann rearrangement reaction of cyclododecanone oxime takes place in [C4mim] and [C4mpyr] with excellent activity and selectivity, while practically null activity is observed in [C4m2im] and [C4mim]. The results obtained indicate that a very low level of hydrolysis of the PF6- anion in [C4mim] and [C4mpyr] occurs under reaction conditions (130 °C), and the HF formed at the level of ppm acts as catalyst in the Beckmann rearrangement with excellent conversion and selectivity.
Efficient nitriding reagent and application thereof
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Paragraph 0420-0423, (2021/03/31)
The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
A process for preparing laurolactam
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Paragraph 0034-0042, (2021/10/05)
A novel process for the preparation of laurolactam (laurolactam) is disclosed. More specifically, cyclo dodecanone (C) as a starting material. 12 H22 O Is a process for the preparation of laurolactam with won -pot reactions (one-pot reaction) by adding a hydroxyl ammonium compound and an inorganic acid.