Palmitic Acid → Stearyl Stearate

HRID 1106951Notes

Reaction equation

HRID 1106951 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=CC(S(O)(=O)=O)=CC=1.C(O)(=O)CCCCCCCCCCCCCCC.C(O)(=O)CCCCCCC/C=C\CCCCCCCC>O>[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

7

Reactant 5

HCID 985Palmitic AcidHCID 5281Stearic Acid3×HCID 6101p-Toluenesulfonic acidHCID 8221Stearyl AlcoholHCID 445639Oleic Acid

Product 1

HCID 17720Stearyl Stearate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A 2-liter round-bottom flask was charged with 142 g (0.5 mole) of rubber-maker's technical grade stearic acid, 203 g (0.75 mole) of 1-octadecanol, 11 g of p-toluenesulfonic acid and 200 ml of mixed xylenes. Rubber-maker's technical grade stearic acid typically contains approximately 56 percent by weight stearic acid, 29 percent by weight palmitic acid, 8 percent by weight oleic acid and 7 percent by weight other fatty acids. The flask was fitted with a Dean-Stark trap for water removal, a heating mantel and a thermocouple. The system was flushed with nitrogen and heated to a pot temperature of 180° C. for about 1 hour, wherein 12 ml of water were removed. Volatiles were removed under 29 inches of vacuum at 110° C. to give 342 g of a waxy solid melting at 47-55° C. and giving an infrared spectrum showing loss of hydroxyl absorption bands and formation of ester carbonyl functions.

Workup

  1. customThe system was flushed with nitrogen
  2. customwherein 12 ml of water were removed
  3. customVolatiles were removed under 29 inches of vacuum at 110° C.

Sources & evidence

ORD record
ord-d5824cb2b0d94c8ab873f4888dbad4b9
Source dataset
uspto-grants-2000_05
Patent number
US06057392

Reaction notes

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