Sorbitol → Isosorbide

HRID 29094

Reaction equation

HRID 29094 reaction equation
O[CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])O)[OH:4]>O>[CH2:11]1[O:12][C@@H:5]2[C@@H:3]([OH:4])[CH2:2][O:8][C@@H:7]2[C@@H:9]1[OH:10]

Participants

3

Reactant 1

HCID 5780Sorbitol

Product 1

HCID 12597IsosorbideYield 42.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
280 °C

Procedure

Sorbitol (25.21 g) was dissolved in water (500 ml) and then transferred to a 1 L autoclave reactor vessel. The catalyst, MFI-40 (HZSM-5 zeolite, 5.02 g), was added. After flushing three times with hydrogen, pressure was set to 300 psi and the reactor was heated with stirring to 280° C. The pressure increased to 1100 psi with heating. Timing began when the reactor reached 280° C. After 30 minutes a 42.4% yield of isosorbide (calculated as mol isosorbide produced/mol starting sorbitol) was obtained.

Workup

  1. customtransferred to a 1 L autoclave reactor vessel
  2. customAfter flushing three times with hydrogen, pressure
  3. temperaturethe reactor was heated
  4. temperatureThe pressure increased to 1100 psi
  5. temperaturewith heating
  6. customreached 280° C

Sources & evidence

ORD record
ord-6664c497811a452b9628c86e54eaa2d4
Source dataset
uspto-grants-2008_09
Patent number
US07420067B2

Linked notes

Loading…