Azone/Pharmaceutical Grade | high Purity/ COAS 59227-89-3

Laurocapram
Properties
Melting point: -7 °C
Boiling point: 160 °C (at 50 mmHg)
Density: 0.906‑0.926
Refractive index: 1.470‑1.473
Storage condition: Sealed in dry, Room Temperature
Solubility: Slightly soluble in chloroform, ethanol and methanol
Form: Oily liquid
Acid dissociation constant (pKa): -0.43±0.20 (Predicted)
Color: Colorless
Merck: 14,5385
Cosmetic function: Skin‑conditioning agent
InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-13-16-19-17-14-11-12-15-18(19)20/h2-17H2,1H3
InChIKey: AXTGDCSMTYGJND‑UHFFFAOYSA‑N
SMILES: N1(CCCCCCCCCCCC)CCCCCC1=O
LogP: 6.570 (est)
CAS: 59227‑89‑3
EPA chemical substance information: Laurocapram (59227‑89‑3)
Uses and Synthesis Method
Brief Introduction
Laurocapram, also known as Azone, is a novel skin‑penetrating agent first reported by Stoughton in the early 1980s. Its chemical name is 1‑n‑dodecylazacycloheptan‑2‑one. At ambient temperature, it is a colorless, odorless oily transparent liquid with lubricity, good spread‑ability and strong penetration performance. As a versatile organic chemical, it gains wide attention for its high penetration‑boosting performance and favorable safety profile. It can enhance penetration for both hydrophilic and hydrophobic compounds.
Applications
It is widely applied in pharmaceutical, agrochemical, cosmetic, textile printing, leather‑making, petroleum, chemical fiber and other fields. Plenty of productive research has been carried out on its domestic production and application, and its application scope keeps expanding. Its annual consumption grows at a rate of 50%. With deeper understanding of this material, its industrialized production possesses promising prospects.
As an efficient skin penetration enhancer and new‑type non‑ionic surfactant, laurocapram has been popularized in pharmaceutical, daily‑chemical, agrochemical, textile printing, chemical fiber, leather and other industries with remarkable performance. More new application scenarios are being continuously explored.
Preparation
Solid‑liquid phase transfer catalytic method:
In this process, mixed base of KOH‑K₂CO₃ is adopted as deprotonating agent instead of single potassium hydroxide or sodium hydroxide. Tetrabutylammonium bromide or polyethylene glycol serves as phase‑transfer catalyst. Caprolactam reacts with 1‑bromododecane in toluene or ethane solvent to produce laurocapram in one‑step reaction, with yield above 93%.
This process features mild reaction conditions and easy operation without nitrogen protection. Reactions are carried out in non‑aqueous solvent. It is a mainstream manufacturing technology widely adopted by domestic producers for laurocapram.