Sodium Chloride → Sweetrex
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].[OH:13][CH2:14][C:15]([C@H:17]([C@@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])=[O:16].[Na+].[Cl-]>CC(CC(C)=O)C>[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].[OH:13][CH2:14][C:15]([C@H:17]([C@@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
An aqueous solution containing 10 wt % glucose and 10 wt % fructose (3 mL, 0.0022 mol glucose, 0.0023 mol fructose) was mounted in an Ace vial pressure tube (stable to ˜20 Bar). Solid NaCl (150 mg, 0.0026 mol) was dissolved in the aqueous phase followed by the addition of MIBK (12 ml) as extracting solvent. The pressure stable tube was sealed and heated to 160° C. for 105 min and subsequently allowed cooling to room temperature. A sample of the reaction mixture was collected and filtered through a syringe filter (0.45 μm PTFE), mixed with an internal standard (i-PrOH) and analyzed via HPLC. The results of the HPLC showed 80% glucose from glucose, 0.0018 mol; 4% fructose from fructose, 9.5·10−5 mol; 64% HMF from fructose, 0.0015 mol; total sugar conversion 59%; HMF selectivity from fructose 67%.
Workup
- customwas mounted in an Ace vial pressure tube
- extractionas extracting solvent
- customThe pressure stable tube was sealed
- temperaturesubsequently allowed cooling to room temperature
- customA sample of the reaction mixture was collected
- filtrationfiltered through a syringe
- filtrationfilter (0.45 μm PTFE)
- additionmixed with an internal standard (i-PrOH)
- customThe results of the HPLC
Sources & evidence
- ORD record
- ord-d69a1eb0b124470eb2d63323484a8b55
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604225B2
Reaction notes
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