Ethyl Lactate → Lauryl Lactate

HRID 249643Notes

Reaction equation

HRID 249643 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14](OCC)(=[O:18])[CH:15]([CH3:17])[OH:16]>>[C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:18])[CH:15]([CH3:17])[OH:16]

Participants

3

Reactant 2

HCID 7344Ethyl LactateHCID 81931-Dodecanol

Product 1

HCID 22692Lauryl LactateYield 78%

Conditions

Temperature
60 °C

Procedure

Novozym® 435 (250-300 g), molecular sieves (2250-2350 g), 1-dodecanol (540-560 mL), and ethyl lactate (1350-1450 mL) were mixed together in a 12″×20″ stainless steel tray (bed depth ˜1.25″). A total of four trays were prepared in parallel, and maintained at 60° C. in a convection oven for 32 hours. After cooling to ambient temperature, the contents of each tray were diluted with petroleum ether, and the enzyme/sieves mixture was removed by vacuum filtration. The combined filtrates were transferred to a 50 L reactor and processed accordingly. Upon work-up, 2024 g of lauryl lactate (78% yield) was obtained as a pale yellow liquid. The purity of the product was >98% as assessed by HPLC-RI.

Workup

  1. customA total of four trays were prepared in parallel, and
  2. temperatureAfter cooling to ambient temperature
  3. customthe enzyme/sieves mixture was removed by vacuum filtration
  4. customThe combined filtrates were transferred to a 50 L reactor

Sources & evidence

ORD record
ord-611118cc5b704d23bc8641a164ac263f
Source dataset
uspto-grants-2011_01
Patent number
US07863025B2

Reaction notes

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