Propionic Acid → Butyric Acid

HRID 2206441Notes

Reaction equation

HRID 2206441 reaction equation
O=C[C@@H]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])O)O)O)O.[C:13]([OH:18])(=[O:17])[C@H:14]([CH3:16])[OH:15].C(O)(=O)CC>C(O)(=O)C>[C:11]([OH:12])(=[O:15])[CH2:9][CH2:7][CH3:5].[C:13]([OH:18])(=[O:17])[CH2:14][CH3:16]

Participants

6

Reactant 3

HCID 1032Propionic Acid2×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal3×HCID 107689L-Lactic Acid3×

Product 2

HCID 264Butyric AcidHCID 1032Propionic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

When glucose is used as the sole substrate, as in the first experiment, the difference between total carbon yield and butyric carbon yield is greater than when a combination of glucose and L-lactic acid is used, because higher amounts of acetic acid and propionic acid are generated during the fermentation. See FIG. 7. In addition, the butyric carbon yield (61%) is much higher than that of free cell fermentation (see Table 1, 36%), because the immobilized cell beads can be used repeatedly for a long period of time, which may cause cell adaptation to endure higher butyrate concentration, thereby resulting in a higher butyric carbon yield. The second experiment using a feedstock containing both glucose and L-lactic acid affords 69% butyric carbon yield (higher than the theoretical yield), while suppressing the generation of acetic acid and propionic acid (the difference between total carbon yield and butyric carbon yield is only 5%). See FIG. 8. Third, when L-lactic acid is used as the sole substrate, butyric acid is produced in an significant amount, although acetic acid and propionic acid are also generated (the difference between total carbon yield and butyric carbon yield is 23%). See FIG. 9. The total carbon yield, 96%, is very close to the theoretical value (100%). In view of the above, the combination of lactic acid and carbohydrate as substrates in fermentation exceeds those results anticipated under conventional fermentation using glucose as the only substrate, and in some instances may be deemed synergistic with the improvement of the butyric carbon yield.

Workup

  1. customthe difference between total carbon yield
  2. custombutyric carbon yield
  3. customIn addition, the butyric carbon yield (61%)
  4. waitbecause the immobilized cell beads can be used repeatedly for a long period of time, which
  5. concentrationbutyrate concentration
  6. customresulting in a higher butyric carbon
  7. customyield
  8. customaffords 69% butyric carbon
  9. customyield (higher than the
  10. customtheoretical yield),
  11. customyield
  12. custombutyric carbon yield

Sources & evidence

ORD record
ord-2a41070f5b8a437e92f5e2d04bb46477
Source dataset
uspto-grants-2016_06
Patent number
US09371548B2

Reaction notes

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