Dodecanoyl chloride
DODECANOYL CHLORIDE · LACL · N-DODECANOYL CHLORIDE · Lauric chloride · LAUROYL CHLORIDE · Dodecanoyl chlorid · Lauroyl chloride,98% · LAURIC ACID CHLORIDE
Identifiers & Physical Properties
| CAS No. | 112-16-3 |
|---|---|
| Molecular formula | C12H23ClO |
| Average molar mass | 218.76 g/mol |
| Monoisotopic mass | 218.143743 g/mol |
| SMILES | CCCCCCCCCCCC(=O)Cl |
| InChIKey | NQGIJDNPUZEBRU-UHFFFAOYSA-N |
| PubChem CID | 8166 |
| ChEMBL | CHEMBL3561663 |
| EC No. | 203-941-7 |
| DTXSID | DTXSID5044368 |
Chemical & Physical Properties
| XLogP | 5.2 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 10 |
| Heavy atoms | 14 |
| Formal charge | 0 |
| Complexity | 134 |
| Color/Form | WATER-WHITE LIQUID |
| Solubility | SOL IN ETHERSoluble in ethanol and methanol.reacts |
| Boiling point | 145 °C @ 18 MM HG134-137 °C/11 mmHg (lit.) |
| Melting point | -17 °C |
| Refractive index | INDEX OF REFRACTION: 1.4458 @ 20 °C/Dn20/D 1.445 |
| Physical Description | LiquidWater white liquid[HSDB] Colorless liquid[MSDSonline] |
| Other Experimental Properties | DECOMP IN WATER, ALCOHOL |
| Density | 0.946 g/mL at 25 °C (lit.) |
| Vapor pressure | 0.5Pa at 20℃ |
| Flash point | >230 °F |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| Color | Clear |
| Sensitivity | Moisture Sensitive |
| BRN | 1281201 |
| Stability | Stable. Incompatible with strong oxidizing agents, amines, strong bases. Do not allow to come into contact with water or moisture. |
| InChI | 1S/C12H23ClO/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3 |
| InChIKey | NQGIJDNPUZEBRU-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCC(Cl)=O |
| CAS DataBase Reference | 112-16-3(CAS DataBase Reference) |
| FDA UNII | 9LHL10777I |
| NIST Chemistry Reference | Dodecanoyl chloride(112-16-3) |
| EPA Substance Registry System | Dodecanoyl chloride (112-16-3) |
| UNSPSC Code | 12352106 |
| NACRES | NA.22 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H314-H290 |
| GHS precautionary statements | P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | C |
| Risk statements (R) | 34-37-29-22-14 |
| Safety statements (S) | 26-36/37/39-45-8 |
| UN transport number | UN 3265 8/PG 2 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Skin Corr. 1B |
| Packing group | II |
| Customs code | 29159080 |
| Storage class | 8A - Combustible corrosive hazardous materials |
| Hazardous substances data | 112-16-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 200 - 2000 mg/kg |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH290 (17.2%): May be corrosive to metals [Warning Corrosive to Metals]H314 (99.5%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H317 (56.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (57%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P234, P260, P261, P264, P264+P265, P272, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P333+P317, P362+P364, P363, P390, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 186 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Dodecanoyl chlorideDodecanoyl chloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Dodecanoyl chloride 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: Cease Manufacture Update: 07-10-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/1369Status: Active Update: 13-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14344Lauroyl chloride: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Dodecanoyl chloride: Human health tier I assessmentIMAP assessments - Dodecanoyl chloride: Environment tier I assessment |
| Hazards summary | Reacts violently with waterA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis[MSDSonline] |
| Hazard Classes and Categories |
Applications & Uses
Uses
Lauroyl chloride is used as tailoring agent for chemical modification of nanocelluloses of different length, nanofibrillated cellulose and cellulose nanocrystals and in the preparation of acylated collagen with water solubility and better surface activity. It is also employed as organic low-friction boundary lubricant in the preparation of novel polyvinyl alcohol hydrogel.It is used in the synthesis of hemicellulose-based hydrophobic biomaterials.
Preparation & Synthesis
Preparation
Lauroyl chloride is synthesized by the reaction of lauric acid with thionyl chloride. Reaction: The flask was charged with lauric acid 1330 (200 g, 1.0 mol) and catalyst (imidazole, 2-methyl imidazole, 2.0 mol% based on the acid), and the mixture was heated with stirring to 90 C°. The stirred mixture was maintained at 90 C° for 1 h, at which time gaseous phosgene was introduced below the surface of the liquid at such a rate as to maintain a gentle phosgene reflux from the deflamator. Phosgene addition was regulated and calculated with the aid of a tubular flowmeter. The reaction was continued, generally within the temperature range 80–100 C°, until hydrogen chloride was no longer evolved (cessation of heat generation at the top of the water scrubber). The phosgene feed was stopped and the reaction mixture was kept at 85–95 C° with gentle phosgene reflux from the deflamator until the evolution of carbon dioxide had ceased (30–60 min, as evidenced by cessation of the gas entering at the base of the scrubber column). Occasionally, additional phosgene was required during this period to maintain phosgene reflux and to complete the reaction. Following complete reaction, the deflamator was replaced by a 10-in. (25 cm) glass helix packed distillation column fitted with a total reflux head, and dissolved phosgene was removed from the stirred reaction product by purging with dry nitrogen at 90 C° for 2 h. The product was distilled at 10 mmHg as a single fraction. Yield: 91–94.5% of lauroyl chloride.