Dodecanoyl chloride

HCID 8166CAS 112-16-3
Substructure searchFind similar structures

Basic information

Standard SMILES
CCCCCCCCCCCC(=O)Cl
InChIKey
NQGIJDNPUZEBRU-UHFFFAOYSA-N
Molecular formula
C12H23ClO
Average molar mass
218.76 g/mol
Monoisotopic mass
218.143743

Names & identifiers

Preferred name
Dodecanoyl chloride
IUPAC
dodecanoyl chloride
English name
Lauroyl chloride
Molecular formula
C12H23ClO
Molecular weight
218.76

Names & synonyms

Lauroyl chlorideDODECANOYL CHLORIDE112-16-3Lauric acid chloriden-Dodecanoyl chlorideLauroylchlorideDodecanoic acid, chlorideDTXSID5044368MFCD000007401,3-dimethyl-1-methylazourea9LHL10777IUNII-9LHL10777I
Show more names
LACLLauric chlorideDodecanoyl chloridLauroyl chloride,98%Lauroyl chloride 98%Lauroyl Chloride >
dodecanoylchlorideDodecanoic Acid Chloride; Lauric Acid Chloride; n-Dodecanoyl ChlorideHSDB 5567EINECS 203-941-7Lauric acid, chlorideAI3-52409Lauroyl chloride, 98%EC 203-941-7

Database identifiers

CAS
112-16-3
PubChem CID
8166
DTXSID
DTXSID5044368
ChEMBL
CHEMBL3561663
UNII
9LHL10777I
EC Number
203-941-7
Nikkaji
J96.190F

Properties

Computed structural properties

XLogP
5.2
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
10
Heavy atoms
14

Experimental & physicochemical properties

Color/FormWATER-WHITE LIQUID
SolubilitySOL IN ETHER
Boiling Point145 °C @ 18 MM HG
Melting Point-17 °C
Refractive IndexINDEX OF REFRACTION: 1.4458 @ 20 °C/D
Physical Description · 2 items

Liquid

Water white liquid; [HSDB] Colorless liquid; [MSDSonline]

Physicochemical properties

Melting point
-17 °C · -17 °C
Boiling point
134 · 134-137 °C/11 mmHg (lit.)
Density
0.946 g/mL · 0.946 g/mL at 25 °C (lit.)
vapor pressure
0.5 Pa · 0.5Pa at 20℃
refractive index
20 · n20/D 1.445
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H290 (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.

Hazard information

Regulatory Information · 4 items

Chemical: Dodecanoyl chloride

Dodecanoyl 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/1369；Status: Active Update: 13-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14344

Lauroyl chloride: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Dodecanoyl chloride: Human health tier I assessment；IMAP assessments - Dodecanoyl chloride: Environment tier I assessment
Hazards SummaryReacts violently with water; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]
Hazard Classes and CategoriesMet. Corr. 1 (17.2%)；Skin Corr. 1B (99.5%)；Skin Sens. 1 (56.5%)；Eye Dam. 1 (57%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.；Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

Regulatory information

Regulatory Information · 4 items

Chemical: Dodecanoyl chloride

Dodecanoyl 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/1369；Status: Active Update: 13-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14344

Lauroyl chloride: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
hs_code
29159080
Toxicity
LD50 orally in Rabbit: 200 - 2000 mg/kg

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as a surfactant, polymerization initiator, anti-enzyme agent, and foaming agent; Also used to make lauroyl peroxide, sodium n-lauroyl sarcosinate, and other sarcosinates; [HSDB]

SURFACTANT, POLYMERIZATION INITIATOR, ANTIENZYME AGENT, FOAMER

IN SYNTHESIS OF LAUROYL PEROXIDE, SODIUM N-LAUROYL SARCOSINATE AND OTHER SARCOSINATES

U.S. Production2023: 1,000,000 - <2,500,000 lb；2022: 1,000,000 - <2,500,000 lb；2021: 1,000,000 - <2,500,000 lb；2020: 1,000,000 - <2,500,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

Oil and Gas Drilling, Extraction, and Support activities；All Other Chemical Product and Preparation Manufacturing

Dodecanoyl chloride: ACTIVE

Applications · 1 item

UsesLauroyl 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 methods · 1 item

PreparationLauroyl 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.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Related reactions

305 records
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Linked notes

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