HCID 56926521, compound → Ribonolactone

HRID 864691Notes

Reaction equation

HRID 864691 reaction equation
[O:1]=[C:2]([O-:11])[C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])O)[OH:6])[OH:4].[Na+].[O:13]=[C:14]([O-])[C@@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16].[Na+]>[Ni]>[C:2]1(=[O:1])[O:11][C@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[C@H:3]1[OH:4].[CH2:14]([OH:13])[C@@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16]

Participants

5

Reactant 2

HCID 56926521HCID 56926521, compoundHCID 86749920Sodium arabinate

Product 2

HCID 111064RibonolactoneHCID 178521086HCID 178521086, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

According to this example the dissolution of the nickel catalyst was prevented by lowering the acidity of the reaction solution with an addition of alkali. The hydrogenation proceeded smoothly and the yield of pentitols was close to the maximum value of 75% in this case. The salts of pentonic acids, of course, did not undergo hydrogenation. On the contrary, sodium D-arabinonate was partly isomerized to sodium D-ribonate, and the subsequent hydrogenation of D-ribono-1,4-lactone resulted in enhanced formation of ribitol. In spite of the isomerization of the starting material, the control of pH can be applied in the production of xylitol from D-arabinonic acid as both arabinitol and ribitol yield xylitol in the second isomerization step. On the contrary, the control of pH can not be applied when L-xylonic acid is to be converted to xylitol.

Workup

  1. additionwith an addition of alkali

Sources & evidence

ORD record
ord-38311581f21548e4a6b21d10460f8d81
Source dataset
uspto-grants-1996_10
Patent number
US05563303

Reaction notes

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