CAS 25038-74-8 Laurolactam (HCID 13690)

Overview

Laurolactam is a keratan 6'-sulfate and an azamacrocycle.

Names & identifiers

Preferred name: Laurolactam
IUPAC: azacyclotridecan-2-one
English name: NYLON 12
Molecular formula: C36H69N3O3X2
Molecular weight: 197.32

Names & synonyms

Azacyclotridecan-2-one947-04-6LaurolactamLauryl lactamDodecyllactamLaurinolactamLaurin lactamomega-LaurolactamCYCLODODECALACTAMDodecanolactam2-Oxo-dodecamethylenimine1-Aza-2-cyclotridecanone

Show more names

Polyamide12NYLON 12 ISO 9001：2015 REACHNtylon-12POLYLAURYLLACTAMLauryl lactam, homopolymerazacyclotridecan-2-one,homopolymerAzacyclotridecane-2-one,homopolymer

omega-Dodecalactamomega-DodecanolactamDodecanoic acid, 12-amino-, lactamDTXSID1027344UB8VFC953GNSC-77100DTXCID107344RefChem:7697

Database identifiers

CAS: 25038-74-8、947-04-6
PubChem CID: 13690
DTXSID: DTXSID1027344
ChEMBL: CHEMBL3181948
ChEBI: CHEBI:172332
UNII: UB8VFC953G
EC Number: 213-424-8
Nikkaji: J12.504K

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 29.1 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 156

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Other Monomers

SpringerMaterials Properties15N nuclear magnetic resonance spectrum

SolubilityVIRTUALLY INSOL IN WATER

Vapor Pressure0.00000731 [mmHg]

Food Contact Substances · 2 items

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

Physical Description · 2 items

Dry Powder; Large Crystals

Solid; [eChemPortal: SIDSUNEP] Very faintly beige crystalline lumps; [MSDSonline]

Physicochemical properties

Melting point: 176 °C · 176 °C
Density: 1.01 g/mL · 1.01 g/mL at 25 °C(lit.)
form: pellets
Cosmetics Ingredients Functions: BULKINGVISCOSITY CONTROLLINGOPACIFYING
LogP: 3.123 · 3.123 (est)
FDA UNII: 446 U8J075B · 446U8J075B
EPA Substance Registry System: -2 · Azacyclotridecan-2-one, homopolymer (25038-74-8)
WGK Germany: 3 · 3
TSCA: TSCA listed

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 96.6% (115 of 119) of all reports.

Not Classified

Aggregated GHS information provided per 119 reports by companies from 2 notifications to the ECHA C&L Inventory.

Warning

H371: May cause damage to organs [Warning Specific target organ toxicity, single exposure]

P260, P264, P270, P273, P308+P316, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 3 items

Chemical: Azacyclotridecan-2-one

Azacyclotridecan-2-one is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Azacyclotridecan-2-one are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 12-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13738

Hazards SummaryMay cause irritation; [MSDSonline] See Caprolactam.

Hazard Classes and Categories · 2 items

Not Classified

Specific target organ toxicity - Single exposure - Category 2 (central nervous system, digestive system)

Toxicology

Non-Human Toxicity Excerpts · 2 items

ALL THE THIOLACTAMS STUDIED CAUSED CLONIC AND TONIC CONVULSIONS IN MICE A FEW SEC AFTER IP ADMIN. THE VARIATION IN THE ACUTE BASAL TOXICITY OF THE THIOLACTAMS WAS MAINLY DUE TO THE CHANGE IN THE LIPOHYDROPHILIC CHARACTER. THE DIPOLE MOMENT APPEARS TO PLAY A SIGNIFICANT ROLE IN DETERMINING THE CONVULSANT ACTIVITY IN THE TOXICITY OF THIOLACTAMS, LACTAMS, & GAMMA-THIOBUTYROLACTONE.

FOR LACTAMS WITH SMALL RING SIZE, CNS STIMULATION APPEARED TO BE DOMINANT IN MICE THAT WERE INJECTED IP WITH A SERIES OF LOGARITHMIC DOSES (30, 100, 300, AND 1000 MG/KG (GROUPS OF 6 ANIMALS, 3 MALES & 3 FEMALES). 2-AZACYCLOTRIDECANONE CAUSED TREMBLING AT 500 MG/KG IN 6/6 MICE.

Safety data

wgk: 3
tsca: TSCA listed

Chemistry & industry

Uses & manufacturing

UsesUsed as a monomer for the polymerization of polyamide; [eChemPortal: SIDSUNEP]

U.S. Production2023: 8,500,000 - <25,000,000 lb

Industry UsesMonomers

General Manufacturing Information · 2 items

Plastics Product Manufacturing

Azacyclotridecan-2-one: ACTIVE

Applications

Usesnylon 12 is a bulking and opacifying agent that provides good feel and good elasticity to moisturizers and makeup preparations, including foundations. nylon 12 reduces oiliness. It is a polyamide derivative of acid 12-aminododecanioic.

Preparation methods · 1 item

PreparationNylon 12 is produced by heating dodecyl lactam at about 300°C in the presence of aqueous phosphoric acid. The polymerization of dodecyllactam does not involve an equilibrium reaction (unlike the polymerization of caprolactam) and hence an almost quantitative yield of polymer is obtained and the removal of low molecular weight material is unnecessary.