Water → Stearyl Stearate

HRID 1656061Notes

Reaction equation

HRID 1656061 reaction equation
[C:1]([OH:20])(=[O:19])[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][CH2:16][CH2:17][CH3:18].[CH2:21](O)[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][CH2:36][CH2:37][CH3:38].C1(C)C(S(O)(=O)=O)=CC=CC=1.O>C1(C)C=CC=C(C)C=1>[C:1]([O:20][CH2:38][CH2:37][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][CH3:21])(=[O:19])[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][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 5281Stearic AcidHCID 69252-Methylbenzenesulfonic acidHCID 8221Stearyl Alcohol

Product 1

HCID 17720Stearyl StearateYield 112.5%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

71.1 grams (0.25 mole) of purified stearic acid (melting point 70° C.) and 101.5 grams (0.375 mole) of 1-octadecanol were added to 5.5 grams of toluenesulfonic acid in 100 ml of m-xylene and charged into a Dean-Stark equipped 1-liter round bottom flask. After 4 hours of reflux under nitrogen at a pot temperature of 180° C., 6 ml of water was collected. The solvent and any excess alcohol were stripped under 29 inches of mercury vacuum at 130° C. to give 151 grams of a solid having a melting point of 58° C. The acid number of the product was 3.0. 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-a1a95d04f477451ca0f5f69380725a90
Source dataset
uspto-grants-1993_10
Patent number
US05252650

Reaction notes

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