D-(-)-Fructose → Mannitol

HRID 2082971Notes

Reaction equation

HRID 2082971 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].O=C[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.OCC([C@H]([C@@H]([C@@H](CO)O)O)O)=O>O[Mo](O)(=O)=O>[CH2:11]([OH:12])[C@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10]

Participants

5

Reactant 3

HCID 5984D-(-)-FructoseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal6×HCID 161658Demannose

Product 1

HCID 6251Mannitol

Reagents, catalysts & solvents 1

HCID 82208Molybdic acidCatalyst

Procedure

A D-glucose solution is added molybdic acid compound thereto and heated at a temperature of 110°-160° C with pH 2.0-4.5 to perform epimerizing reaction of D-glucose, and thereby 30-36%, based on the D-glucose, of D-mannose is formed. To the epimerized mixture thus obtained is further added glucose-isomerase to perform enzymatic isomerizing reaction of D-glucose remaining in the epimerized mixture, thereby 46% based on the remaining D-glucose is converted into D-fructose. The epimerized mixture or enzymatically isomerized mixture is subjected to catalytic hydrogenation under high pressure, and thereby is produced D-mannitol at high yield based on the initial D-glucose.

Workup

  1. temperatureheated at a temperature of 110°-160° C with pH 2.0-4.5
  2. customis formed
  3. customTo the epimerized mixture thus obtained

Sources & evidence

ORD record
ord-fe3238c72b6946bc86da17c79c5dde8c
Source dataset
uspto-grants-1978_04
Patent number
US04083881

Reaction notes

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