70394-23-9

Basic information

• Product Name: 3-(dimethylamino)hexahydro-2H-azepin-2-one
• Synonyms: 3-(dimethylamino)hexahydro-2H-azepin-2-one;L-(-)-α-Dimethylamino-ε-caprolactam;3-(Dimethylamino)hexahydro-1H-azepin-2-one;D-(+)-α-Dimethylamino-ε-caprolactam
• CAS NO: 70394-23-9
• Molecular Formula: C8H16N2O
• Molecular Weight: 156.22544
• EINECS: 274-592-6
• Mol File: 70394-23-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 307°C at 760 mmHg
• Flash Point: 139.5°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 0.000743mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 3-(dimethylamino)hexahydro-2H-azepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(dimethylamino)hexahydro-2H-azepin-2-one(70394-23-9)
• EPA Substance Registry System: 3-(dimethylamino)hexahydro-2H-azepin-2-one(70394-23-9)

Safety Data

• Hazardous Substances Data: 70394-23-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H16N2O/c1-10(2)7-5-3-4-6-9-8(7)11/h7H,3-6H2,1-2H3,(H,9,11)

Upstream product

• 50-00-0 formaldehyd 
• 21568-87-6 2-aminocaprolactam 
• 67-56-1 methanol 
• 56-87-1 L-lysine 
• 26081-03-8 (S)-3-aminocaprolactam hydrochloride 
• 17929-90-7 3-aminoazepan-2-one 
• 29426-64-0 (R)-α-amino-ε-caprolactam hydrochloride 
• 70-54-2 2,6-diaminocaproic acid 

Relevant articles and documents

Preparation method of caprolactam

The invention provides a preparation method of caprolactam. According to the method, lysine or alpha-amino-epsilon-caprolactam and a salt thereof and alpha-(N,N-dimethylamino)-epsilon-caprolactam anda salt thereof are used as reaction raw materials, a transition metal supported by an acidic carrier is taken as a catalyst, methanol is taken as a solvent, and one-step catalytic conversion is carried out under the conditions that the temperature is 150-300 DEG C and the hydrogen pressure is 1-12 MPa, so that the process for producing caprolactam from lysine derived from biomass and other raw materials is realized. According to the invention, the reaction process is simple, the raw materials such as lysine, alpha-amino-epsilon-caprolactam and a salt thereof and alpha-(N, N-dimethylamino)-epsilon-caprolactam and a salt thereof can be derived from biomass, and have the advantages of being environmentally friendly, renewable and the like, the supported catalyst is easy to separate, and the transition metal catalyst supported by the acidic carrier is not easy to lose in the reaction process.

One-pot conversion of lysine to caprolactam over Ir/H-Beta catalysts

Amino acid lysine could serve as an ideal bio-based feedstock for the synthesis of caprolactam (CPL), which is currently a petroleum-derived monomer. Herein, we report the one-pot conversion of l-lysine to CPL via hydrogenolysis over bifunctional metal supported catalysts. Among the various hydrogenation metals and different supports, the combination of Ir and HB zeolite gave the best performance. Under optimal conditions, a 30% yield of CPL from l-lysine and a 58% yield from the reaction intermediate α-dimethyl amino caprolactam (DMAC) were obtained over a 2Ir/HB-124 catalyst at 250 °C in an autoclave or fixed-bed reactor. The reaction solvent dramatically affected the reaction selectivity, and methanol was found to be the best due to its unique contribution towards the formation of α-dimethyl amino caprolactam (DMAC) as well as the following C-N breakage of the C-N(CH3)2 bond. The acid sites on the catalyst accelerate lactam formation, and the synergy between the acid sites and hydrogenation sites favours C-N bond hydrogenolysis to produce CPL. Besides the acidity, the large pore size of HB is able to accommodate big reaction intermediate molecules inside the pores further ensures the superior performance of Ir/HB. The reaction route was identified, i.e., l-lysine first undergoes cyclization and N-methylation to DMAC, and then C-N(CH3)2 bond hydrogenolysis to form CPL. The Ir/HB catalyst has reasonably good stability and high selectivity, making this one-pot conversion process a novel and environmentally benign way of producing CPL from easily available renewable feedstocks.