Water → Octadecyl hexadecanoate

HRID 1656062Notes

Reaction equation

HRID 1656062 reaction equation
[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:19](O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].O>C1(C)C=CC=C(C)C=1.C1(C)C(S(O)(=O)=O)=CC=CC=1>[C:1]([O:18][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 985Palmitic AcidHCID 8221Stearyl Alcohol

Product 1

HCID 75778Octadecyl hexadecanoateYield 129.3%

Reagents, catalysts & solvents 2

HCID 69252-Methylbenzenesulfonic acidCatalystHCID 7929M-XyleneSolvent

Procedure

128 grams (0.5 mole) of purified palmitic acid (melting point 63° C.) and 203 grams (0.75 mole) of 1-octadecanol were added to 11 grams of toluenesulfonic acid in 130 ml of m-xylene and charged into a Dean-Stark equipped 1-liter round bottom flask. After 6 hours of reflux under nitrogen at a pot temperature of 190° C., 13 ml of water was collected. The solvent and any excess alcohol were stripped under 29 inches of mercury vacuum at 130° C. to give 329 grams of a solid having a melting point of 55° C. The acid number of the product was 0. Infrared spectroscopic analysis showed formation of the ester function.

Workup

  1. additioncharged into a Dean-Stark
  2. customequipped 1-liter round bottom flask
  3. customwas collected
  4. customwere stripped under 29 inches of mercury vacuum at 130° C.

Sources & evidence

ORD record
ord-87454ddf1a47466793395abe5eb06084
Source dataset
uspto-grants-1993_10
Patent number
US05252650

Reaction notes

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