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Dimethyl Sulfoxide → D-Arabinose

HRID 39495
Notes
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Reaction equation

HRID 39495 reaction equation
CS(C)=O.[O:5]=[CH:6][C@@H:7]([C@H:9]([C@@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8].C(=O)C1OC=CC=1>O>[O:5]=[CH:6][C@H:7]([C@@H:9]([C@@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7362Furfural2×HCID 644160aldehydo-D-Xylose2×

Product 1

HCID 66308D-Arabinose

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

ICBP Corn Cob (18.9 g, 1-2 mm, 92.5% dry matter) at 25% solid loading was placed in the reactor containing 0.15 M aqueous sulfuric acid (Comparative Example A) or 0.15 M aqueous hydrochloric acid solution (Comparative Example B) (51.1 g) and gradually heated to 160° C. over a period of 13 min and then maintained at this temperature for 30 min as described in the general procedure. At the end of the reaction, the reaction mixture was diluted with water (103.2 g) containing DMSO (1.33 g) and thoroughly mixed. A sample of this reaction mixture was analyzed as described above for xylose and furfural content. The reaction was repeated under identical conditions to validate the reproducibility of data. Results are presented in Table 2. A mixture of furfural, xylose and arabinose was obtained, indicating incomplete conversion of hemicellulose to the desired product furfural.

Workup

  1. dry with materialICBP Corn Cob (18.9 g, 1-2 mm, 92.5% dry matter) at 25% solid loading
  2. additioncontaining 0.15 M aqueous sulfuric acid (Comparative Example A) or 0.15 M aqueous hydrochloric acid solution (Comparative Example B) (51.1 g)
  3. temperaturemaintained at this temperature for 30 min
  4. customAt the end of the reaction
  5. additionthoroughly mixed
  6. customResults

Sources & evidence

ORD record
ord-3e785a1a7e1a40b582adaafdf67ff5eb
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524925B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes