D-(-)-Fructose → 5-(Hydroxymethyl)furfural

HRID 1500256Notes

Reaction equation

HRID 1500256 reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])O)O)=O>O1CCOCC1>[CH:7]1[CH:5]=[C:3]([CH:2]=[O:1])[O:10][C:9]=1[CH2:11][OH:12]

Participants

3

Reactant 1

HCID 5984D-(-)-Fructose2×

Product 1

HCID 2373325-(Hydroxymethyl)furfural

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

14.3 g of high-fructose maize syrup (containing 10 g of carbohydrate, wherein fructose is 9 g, 50 mmol) was put into a 250 mL round-bottom flask, and 10 g of Amberlyst 15 resin was added therein. Next, 100 mL of dioxane was put into the reactor, and stirred for 3 hours at 100° C. After the reaction, Amberlyst 15 was filtered, and then the reactant was washed and reactivated by processing with acetone for 3 times, with distilled water for 3 times, with 2N NaOH for 2 times, with distilled water for 2 times, with 3N HCl for 2 times, with distilled water for 2 times, and with acetonitrile for 2 times. Then, the reactant was dried and reused for the next reaction. As a result of the HPLC analysis on the yield rates of 5-hydroxymethyl-2-furfural obtained by reusing Amberlyst 15 resin, it could be seen that the activity of Amberlyst 15 was sustainable.

Workup

  1. customwas put into a 250 mL round-bottom flask
  2. addition10 g of Amberlyst 15 resin was added
  3. customAfter the reaction, Amberlyst 15
  4. filtrationwas filtered
  5. washthe reactant was washed
  6. customThen, the reactant was dried
  7. customreused for the next reaction

Sources & evidence

ORD record
ord-01a5626f59c84e6aadbd1f7ae41349fc
Source dataset
uspto-grants-2015_12
Patent number
US09206148B2

Reaction notes

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