Sodium Chloride → Sweetrex

HRID 1911988Notes

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

Conditions

Temperature: 150 °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 150° C. for 2 h 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 84% glucose from glucose, 0.0019 mol; 44% fructose from fructose, 0.0010 mol; 33% HMF from fructose, 0.0008 mol; total sugar conversion 33%; HMF selectivity from fructose 59%.

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-4f906185579249fa9fcd7e45e254fd0d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604225B2

Reaction notes

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