Lauroyl chloride Property

Melting point:

-17 °C

Boiling point:

134-137 °C/11 mmHg (lit.)

Density 

0.946 g/mL at 25 °C (lit.)

vapor pressure 

0.5Pa at 20℃

refractive index 

n20/D 1.445

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

Soluble in ethanol and methanol.

form 

Liquid

color 

Clear

Water Solubility 

reacts

Sensitive 

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.

InChIKey

NQGIJDNPUZEBRU-UHFFFAOYSA-N

CAS DataBase Reference

112-16-3(CAS DataBase Reference)

NIST Chemistry Reference

Dodecanoyl chloride(112-16-3)

EPA Substance Registry System

Dodecanoyl chloride (112-16-3)

Safety

Hazard Codes 

C

Risk Statements 

34-37-29-22-14

Safety Statements 

26-36/37/39-45-8

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29159080

Hazardous Substances Data

112-16-3(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 200 - 2000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

P405Store locked up.

Lauroyl chloride Chemical Properties,Usage,Production

Chemical Properties

colourless to light yellow liquid with odor of hydrochloric acid. Soluble in ether, decomposed in water and alcohol.

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.

Application

Dodecanoyl chloride aslo known as lauroyl chloride is an acid chloride that can be used as a reagent for the surface modification of:
Chitosans, by converting it into acylated chitosans for increasing solubility in organic solvents.
Microfibrillated cellulose (MFC) for improving dispersibility in biopolyamide nanocomposites.
It can also be used as a:
Starting material for the synthesis of (R)-3-aminotetradecanoic acid (iturinic acid).
Reagent for the preparation of (3,6-bis(dodecanamido)-2,7-dibromo-9-dodecyl-9H-carbazole).This amide intermediate can be further used in the synthesis of azomethine-bridged ladder-type poly( p-phenylene)s.

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.

Reactions

Lauroyl chloride is a substrate for diverse reactions characteristic of acid chlorides. With base, it converts to laurone, a ketone with the formula [CH3(CH2)10]2CO. With sodium azide, it reacts to give undecyl isocyanate via a Curtius rearrangement of the acyl azide.

Flammability and Explosibility

Not classified