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Title: Preparation of (-)-Levoglucosenone from Cellulose Using Sulfuric Acid in Polyethylene Glycol
Contributor(s): Klepp, J  (author); Dillon, W (author); Lin, Y (author); Feng, P (author); Greatrex, B W  (author)orcid 
Publication Date: 2020
Open Access: Yes
DOI: 10.15227/orgsyn.097.0038Open Access Link
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Abstract: (-)-Levoglucosenone (LGO, 1). Polyethylene glycol 4000 (PEG) (200 g) (Note 2) is ground to a course powder (Figure 1) in a mortar (φ: 200 mm) and pestle (203 mm) and placed in a 500 mL beaker. A diluted solution of sulfuric acid (2.50 g, 25.5 mmol) in methanol (15 mL) (Note 3) is added at ambient temperature (22 °C) and the powder is mixed using a large spatula (18 cm) to distribute the acid into the powdered PEG and allowing most of the methanol to evaporate. Cellulose powder (50 g, 308 mmol of monomer) (Note 4) is added and the powders combined by stirring with the spatula for three minutes giving an intimate mixture of PEG/acid and cellulose powders (Figure 2). The powder mixture is transferred using a large powder funnel into a 1 L three-necked, round-bottomed flask. The left neck is equipped with a distillation head with the water-cooled Liebig condenser and 100 mL receiver flask. The center neck is equipped with a 29/32 cap, and the right neck is equipped with a thermocouple inserted through a 15/25 rubber septum (Figure 3). Two traps are connected to distillation setup. The first one is 100 mL two-necked flask and the second trap is a cold-finger. Each trap is cooled to -78 °C using a dry ice/methanol bath.
Publication Type: Journal Article
Source of Publication: Organic Syntheses, v.97, p. 38-53
Publisher: John Wiley & Sons, Inc
Place of Publication: United States of America
ISSN: 2333-3553
Field of Research (FOR): 030503 Organic Chemical Synthesis
Socio-Economic Objective (SEO): 970103 Expanding Knowledge in the Chemical Sciences
860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology

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