beta-Maltose → D-(+)-Cellobiose (CNP0226604.15)

HRID 861634Notes

Reaction equation

HRID 861634 reaction equation
[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@H:12]([OH:17])[O:11][C@@H:10]2[CH2:18][OH:19])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].C(=O)([O-])[O-:25].[Ca+2].[Br-].[Ca+2].[Br-]>O>[CH2:1]([OH:23])[C@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]([C@H:14]([OH:15])[C@@H:13]([OH:16])[C:12]([OH:17])=[O:11])[C@H:10]([OH:25])[CH2:18][OH:19])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[CH2:1]([OH:23])[C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@H:12]([OH:17])[O:11][C@@H:10]2[CH2:18][OH:19])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22]

Participants

6

Reactant 3

HCID 6255beta-Maltose4×HCID 10112Calcium CarbonateHCID 5360316Calcium Bromide

Product 2

HCID 10712D-(+)-Cellobiose (CNP0226604.15)HCID 6452827Cellobionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
8 °C

Procedure

Maltose (1 kg, 2.92 moles) is dissolved into 3.8 l, deionized water with heating, in the range of about 40° C. to 60° C., or sufficient to dissolve the maltose. Calcium carbonate (381 g, 3.81 moles) and calcium bromide (51 g, 0.26 mole) are added with mixing. The solution is poured into an electrolysis chamber equipped with a cooling loop and cooled. Six volts DC are applied to opposite graphite electrodes. At 8 hour intervals, the potential is reversed. After 24 h, maltose (1 kg, 2.92 moles) is added and electrolysis is continued until essentially all of the maltose is converted to its acid form (as measured by HPLC), about 104 h total time. The solution is filtered to remove excess calcium carbonate and the pH of the filtrate is adjusted to 2.0 with sulfuric acid. The solution is cooled about 12 to 16 h to 8° C., and filtered to remove calcium sulfate. Calcium ions are removed by batch adsorption to Amberlite IRA 120 resin in the hydrogen form. The sulfate and bromide ions are removed by batch adsorption to Amberlite IRA 68 resin in the hydroxide form. The solution is spray dried with a Bowen 3 ft (1 m) flat bottom laboratory spray drier with a 2 fluid nozzle atomizer. The inlet temperature is kept at about 280° F. to 300° F. (138° C. to 149° C.) with all ports closed. The cellobionic acid is produced in the same manner from cellobiose.

Workup

  1. temperaturewith heating, in the range of about 40° C. to 60° C.
  2. additionwith mixing
  3. additionThe solution is poured into an electrolysis chamber
  4. customequipped with a cooling loop
  5. temperaturecooled
  6. waitAfter 24 h
  7. customis converted to its acid form (as measured by HPLC), about 104 h total time
  8. filtrationThe solution is filtered
  9. customto remove excess calcium carbonate
  10. filtrationfiltered
  11. customto remove calcium sulfate
  12. customCalcium ions are removed by batch adsorption to Amberlite IRA 120 resin in the hydrogen form
  13. customThe sulfate and bromide ions are removed by batch adsorption to Amberlite IRA 68 resin in the hydroxide form
  14. customdried with a Bowen 3 ft (1 m) flat bottom laboratory spray drier with a 2 fluid nozzle atomizer
  15. customis kept at about 280° F. to 300° F.
  16. custom(138° C. to 149° C.)
  17. customclosed

Sources & evidence

ORD record
ord-0332836363304d12928bc277ba5b437b
Source dataset
uspto-grants-1998_02
Patent number
US05714598

Reaction notes

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