1-Tetradecanol → Myristyl myristate

HRID 736022Notes

Reaction equation

HRID 736022 reaction equation
[C:1]([OH:16])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>>[C:1]([O:16][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 82091-TetradecanolHCID 11005Myristic Acid

Product 1

HCID 18605Myristyl myristate

Procedure

34.3 g myristic acid and 32.2 g myristyl alcohol were heated up to 95° C. and 4 g ground immobilised esterase as prepared in Example 13 were added. Samples of the reaction mixture were withdrawn after 1, 2, 4, 8 and 24 h for conversion determination by acid value titration. The initial activity in myristyl myristate synthesis was determined by the help of the mathematical means from example 1.2. After 24 h the reaction was stopped and the enzyme was recovered by mixing the ester with 200 g warm acetone, filtering and washing the residual enzyme with 40 g warm acetone twice. After drying the enzyme in an exsiccator over night under 20 mbar vacuum and ambient temperature, the recovered enzyme was used again in myristyl myristate synthesis in the same manner as described above and was shown to maintain its activity following the above described procedure. The procedure was repeated 10 times. The enzyme was stable throughout the entire test, in the last cycle a relative activity of approx. 95% was found which is within the detection limits. The results are shown in Table 14.

Workup

  1. customas prepared in Example 13
  2. additionwere added
  3. customSamples of the reaction mixture were withdrawn after 1, 2, 4, 8 and 24 h for conversion determination by acid value titration
  4. customThe initial activity in myristyl myristate synthesis
  5. customthe enzyme was recovered
  6. additionby mixing the ester with 200 g
  7. temperaturewarm acetone
  8. filtrationfiltering
  9. washwashing the residual enzyme with 40 g
  10. temperaturewarm acetone twice
  11. customAfter drying the enzyme in an exsiccator over night under 20 mbar vacuum and ambient temperature
  12. customsynthesis in the same manner
  13. temperatureto maintain its activity

Sources & evidence

ORD record
ord-927e9ff0b0c04559992986024f75b0e6
Source dataset
uspto-grants-2009_09
Patent number
US07595181B2

Reaction notes

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