Formation of dimethylbenzenediol via acyloin condensation and a reduction-oxidation pathway
Interest with benzenediol formation was initiated by the isolation and identification of 2,5-dimethyl-1,4-benzenediol from the liquefaction product of cellulose. During that same work 2,5-dimethyl-2,5-cyclohexadiene-1,4-dione(1), 2,3-butadione (biacetyl) and 3-hydroxy-2-butanone (acetoin) were also detected as liquefaction products under aqueous alkaline conditions. Several alkylbenzenediols have been isolated as alkaline degradation products of xylose and glucose, while 1 was observed after alkali treatment of sucrose. Early work had indicated that both 1 and 2,5-methyl-1,4-benzenediol, (2), could be prepared by warming 10g of biacetyl in 200 ml of dilute caustic solution. However, yield information was given only for the product of 2,3-pentadione (10% of 2,5-diethyl-2,5-cyclohexadiene-1,4-dione). Results with biacetyl under similar conditions suggested that the yields of 1 and 2 were in the 1 to 5% range depending upon reaction time; i.e. 0.75 hr was required for 1% 1 while 4 hrs were required for 5% 1. When acetoin was subjected to similar conditions neither 1 or 2 were detected during the initial 4 hr.
- Research Organization:
- Pacific Northwest Lab., Richland, WA (USA)
- DOE Contract Number:
- AC06-76RL01830
- OSTI ID:
- 6024412
- Report Number(s):
- PNL-SA-10350(2); ON: DE85005527
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
ALKALINE HYDROLYSIS
ALKYLATED AROMATICS
AROMATICS
CARBOHYDRATES
CELLULOSE
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DECOMPOSITION
GLYCOLS
HYDROCARBONS
HYDROLYSIS
HYDROXY COMPOUNDS
KETONES
LIQUEFACTION
LYSIS
ORGANIC COMPOUNDS
OXIDATION
POLYSACCHARIDES
REDUCTION
SACCHARIDES
SOLVOLYSIS
SYNTHESIS
THERMOCHEMICAL PROCESSES
XYLENES
YIELDS