Methanol → Methyl hex-2-ulofuranoside

HRID 1865154Notes

Reaction equation

HRID 1865154 reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].[CH3:13]O>>[CH3:13][O:4][C@:3]1([CH2:2][OH:1])[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@@H:5]1[OH:6]

Participants

3

Conditions

Temperature
160 °C

Procedure

A mixture of methanol and fructose was initially charged in a stirred vessel A. The fraction of fructose was 30% of the methanol fraction. The mixture was conveyed by a suitable pump B at a pressure of 120 bar continuously through the reactor C. The tubular reactor C was heated to a temperature of 160° C. by the heater D. A carrier stream comprising pure methanol from the reservoir F was heated to approx. 300° using the preheater G. At the mixing point H, the carrier stream was mixed with the reactant stream and fed to the reactor. The preheating temperature was sufficiently high that reaction temperature was already present at the mixing point, so that the temperature gradient in the reactor was sufficiently low to prevent carbonization at the wall. The residence time in the tubular reactor was approx. 2 min. With the aid of the control valve E, the pressure was kept at the target value mentioned. At the outlet of the system, the reacted product mixture was collected. According to HPLC, the product mixture contained 4% product.

Workup

  1. additionwas initially charged in a stirred vessel A
  2. temperaturewas heated to approx. 300°
  3. additionAt the mixing point H, the carrier stream was mixed with the reactant stream and fed to the reactor
  4. customThe preheating temperature was sufficiently high that reaction temperature
  5. customAt the outlet of the system, the reacted product mixture was collected

Sources & evidence

ORD record
ord-b4fe85b5472a401290812f2f9c128c1b
Source dataset
uspto-grants-2009_12
Patent number
US07626006B2

Reaction notes

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