Isopropyl Stearate → (S)-(+)-2-Decanol

HRID 1939753Notes

Reaction equation

HRID 1939753 reaction equation
C(OC(C)C)(=O)CCCCCCCCCCCCCCCCC.C([O:43][CH:44]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH3:45])(=O)CCCCCCCCCCCCCCCCC>O>[CH3:45][C@H:44]([OH:43])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

4

Conditions

Temperature
85 °C

Procedure

In a 300 ml separable flask were put 1 g of Lipase PL, and 40 g of (R,S)-2-decanol, and the mixture was subjected to ultrasonication with the same ultrasonic wave generating equipment as used in Example 1 at room temperature and 90 kHz for 1 minute. To the mixture was added 60 g of isopropyl stearate, followed by stirring at 85° C. and 250 rpm for 30 hours to carry out interesterification. The water content of the reaction system was 0.02% by weight, and 96% of the lipase particles had a particle size of 10 to 40 μm. Gas chromatographic analysis of the reaction mixture revealed that 57 mol % of (R,S)-2-decanol had been converted to 2-decyl stearate. Lipase was removed by filtration in the same manner as in Example 8, and the filtrate was subjected to simple distillation at 70° C. and 5 mmHg to recover unreacted (S)-(+)-2-decanol (yield: 73.5%; chemical purity: 99.9%; optical purity: 93% ee).

Workup

  1. customIn a 300 ml separable flask were put
  2. customas used in Example 1 at room temperature
  3. wait250 rpm for 30 hours to carry out
  4. customLipase was removed by filtration in the same manner as in Example 8
  5. distillationthe filtrate was subjected to simple distillation at 70° C.

Sources & evidence

ORD record
ord-3cef74ef0e8b49e485f41a429ef145a5
Source dataset
uspto-grants-1997_12
Patent number
US05696299

Reaction notes

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