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

HRID 2184093Notes

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

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

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

Sources & evidence

ORD record: ord-f9ee999ff0274b738ca5477d51a63f54
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900295B2

Reaction notes

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