D-(+)-Cellobiose (CNP0226604.15) → Adipic Acid

HRID 429503

Reaction equation

HRID 429503 reaction equation
C(O)[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O.[C:24]([O:34]C)(=[O:33])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30].CN(C1C=CC=CN=1)C.C(Cl)(=O)CCCCC(Cl)=O>O1CCOCC1>[C:24]([OH:34])(=[O:33])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30]

Participants

6

Reactant 4

HCID 10712D-(+)-Cellobiose (CNP0226604.15)HCID 12329DimethyladipateHCID 218852-DimethylaminopyridineHCID 61034Adipoyl chloride

Product 1

HCID 196Adipic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Five grams of resin (Mw of 50,000) synthesized from cellobiose and dimethyl adipate were poured into dioxane and then 3.7 g of dimethylaminopyridine and 3.0 g of adipic acid chloride were added dropwise thereto in a nitrogen atmosphere, followed by stirring for 20 hours at 50° C. A white powder, obtained from the resulting reaction mixture, was subjected to GPC. As a result, the molecular weight of the white powder was two to eight times larger than that of the resin measured before the reaction. The infrared absorption spectroscopy of the white powder revealed that the intensity of an absorption peak due to the C═O bond in the ester bond was higher than that shown in FIG. 8. Therefore, it was understood that esterification occurred in the saccharide portions in the resin of Example 1 and resulted in crosslinks by adipic acid.

Workup

  1. customA white powder, obtained from the resulting reaction mixture
  2. custommeasured before the reaction
  3. customThe infrared absorption spectroscopy of the white powder

Sources & evidence

ORD record
ord-ddbf35c92fb14be1a5d46f04956c4a83
Source dataset
uspto-grants-2001_11
Patent number
US06316606B1

Linked notes

Loading…