Lauroyl chloride is the organic compound with the formula CH₃(CH₂)₁₀COCl. It is the

acid chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

lauric acid Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of Medium-chain triglyceride, medium-chain fatty acids. It is a bright white, powdery solid with a faint odor of Piment ...

. Lauroyl chloride is a standard reagent for installing the lauroyl group. It is mainly produced as a precursor to

dilauroyl peroxide Dilauroyl peroxide is an organic compound with the formula (C11H23CO2)2. A colorless solid, it is often sold as a water-damped solid. It is the symmetrical peroxide of lauric acid Lauric acid, systematically dodecanoic acid, is a saturated fatt ...

, which is widely used in free-radical polymerizations. Lauroyl chloride is a substrate for diverse reactions characteristic of acid chlorides. With base, it converts to laurone, a ketone with the formula H₃(CH₂)₁₀sub>2CO. With

sodium azide Sodium azide is an inorganic compound with the formula . This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is highly soluble in water and is acutely poisonou ...

, it reacts to give undecyl

isocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...

via a

Curtius rearrangement The Curtius rearrangement (or Curtius reaction or Curtius degradation), first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. The isocyanate then undergoes attack by a ...

of the

acyl azide In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group () or hydrogen in the case of formyl group ( ...

.{{cite journal , doi=10.15227/orgsyn.024.0094, title=Undecyl Isocyanate, first1=C. F. H., last1=Allen, first2=Alan, last2=Bell, journal=Organic Syntheses, year=1944, volume=24, page=94

References

Acyl chlorides Fatty acids Laurates