Acetyl chloride → Stearic Acid

HRID 1251298Notes

Reaction equation

HRID 1251298 reaction equation
C(Cl)(=O)CCCCCCCCCCCCCCCCCCCCC.[C:25]([OH:48])(=[O:47])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]CCCC.C(Cl)(=O)C>C(Cl)(Cl)Cl>[C:25]([OH:48])(=[O:47])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

5

Reactant 3

HCID 6367Acetyl chloride3×HCID 8215Docosanoic Acid3×HCID 4104741Docosanoyl chloride2×

Product 1

HCID 5281Stearic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Acylation was performed according to the invention on Whatman n0 2 paper with behenic acid chloride, behenic acid being a fatty acid with a saturated linear chain having C22. To this end, 500 mg of behenic acid were dissolved in 100 ml of chloroform in the presence of 500 mg of acetyl chloride. At the end of 15 minutes, a sample of paper was impregnated with the chloroform solution, the solvent was allowed to evaporate and a stream of gas at 150° C. was passed over the sample for 15 seconds. The presence of an excess of acetyl chloride made it possible, by means of a transchlorination reaction, to prepare behenic acid chloride extemporaneously. The excess of acetyl chloride was then eliminated by the gas stream by virtue of its high volatility. The very short dwell time of the acetyl chloride was, moreover, not sufficient for it to react significantly with the support. It was found that behenic acid was efficiently grafted onto the paper sample while providing a hydrophobic character very significantly greater than that provided by stearic acid.

Workup

  1. customAt the end of 15 minutes
  2. customto evaporate
  3. customby means of a transchlorination reaction
  4. customnot sufficient for it to react significantly with the support
  5. customwhile providing a hydrophobic character very significantly greater than

Sources & evidence

ORD record
ord-b1bb3d16366d435588dce270f9383814
Source dataset
uspto-grants-2002_01
Patent number
US06342268B1

Reaction notes

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