Hydrochloric Acid → (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 1951965Notes

Reaction equation

HRID 1951965 reaction equation
CC1OC(CO)C(O)C([O:11][CH:12]2[O:17][CH:16]([CH2:18][O:19]C3OCC(O)C(OC)C3O)[CH:15]([OH:30])[CH:14]([O:31]C)[CH:13]2[OH:33])C1O.Cl>O>[O:11]=[CH:12][C@@H:13]([C@H:14]([C@H:15]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:30])[OH:31])[OH:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24847856HCID 24847856, compound

Product 1

HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

500 kg of galactoarabinan (e.g. FiberAid®) are dissolved or suspended in 4,000-5,000 l of water. The pH is adjusted using approximately 50-60 l hydrochloric acid (30% by weight) to a value in the range from 1.0-1.5. The temperature is adjusted to 100° C. The hydrolysis is carried out for 24 hours (hydrolysis control by means of HPLC). Once the hydrolysis is complete cooling takes place to 50-60° C., with filtration (for example by means of a chamber filter press, for example with the Hyflo filter aid) and neutralization, with the solution or the suspension being passed over an alkaline ion exchanger and then again over an acid ion exchanger and then again over an alkaline ion exchanger. The ion exchangers are rinsed with approximately 2,000 l town water. Then the solution or suspension is concentrated by distillation (to approximately 1,500 l) and made to crystallize. The raw ingredient is centrifuged. 500 l 90% by weight of ethanol (remainder: water) are added to the raw product and agitated for one hour at a temperature of approximately 20° C. Through filtration (for example in a chamber filter press) the flushing liquor is separated from the solid matter. This process is carried out twice. The D-galactose raw product is dissolved for recrystallization (100° C., water, saturated solution), active charcoal is added and then filtration performed, for example via the Hyflo filter aid. From the filtrate the D-galactose can be crystallized again and then centrifuged. If necessary, for further purification, recrystallization can be performed again (saturated solution crystallization). Next, the D-galactose obtained in this way is dried (for example by circulating air or vacuum drying cabinet) and ground to the desired particle size.

Workup

  1. customis adjusted to 100° C
  2. custom(hydrolysis control by means of HPLC)
  3. temperatureOnce the hydrolysis is complete cooling
  4. customto 50-60° C.
  5. filtrationwith filtration (for example by means of a chamber
  6. filtrationfilter press
  7. washThe ion exchangers are rinsed with approximately 2,000 l town water
  8. concentrationThen the solution or suspension is concentrated by distillation (to approximately 1,500 l)
  9. customto crystallize
  10. addition500 l 90% by weight of ethanol (remainder: water) are added to the raw product
  11. filtrationThrough filtration (for example in a chamber
  12. filtrationfilter press) the flushing liquor
  13. customis separated from the solid matter
  14. dissolutionThe D-galactose raw product is dissolved for recrystallization (100° C., water, saturated solution), active charcoal
  15. additionis added
  16. filtrationfiltration
  17. filtrationfilter aid
  18. customFrom the filtrate the D-galactose can be crystallized again
  19. customIf necessary, for further purification, recrystallization
  20. custom(saturated solution crystallization)

Sources & evidence

ORD record
ord-593063820edb4017b9279e7265a59ced
Source dataset
uspto-grants-2013_03
Patent number
US08404835B2

Reaction notes

Loading…