Sulfuric Acid → Isosorbide

Weighed amounts of aqueous 70% sorbitol solution were added to 12 separate glass reaction tubes. Each of these reaction tubes was connected to a water trap and set up according to the diagram in FIG. 1. The water trap contained 25 mL of water. Into each reaction tube was injected 483 μL of an aqueous solution containing 0.1075 g of concentrated sulfuric acid. The nitrogen purge into each tube was adjusted to 150 cm3/min. All of the reaction tubes were lowered at once into a 180° C. oil bath. Each tube was pulled from the oil bath at different times as listed in Table 1 to cool and stop the reaction. The mass of the crude remaining in each tube was determined. Small weighed samples of crude material (on the order of 150 mg) from each separate reaction tube were removed and diluted with a weighed amount of 1,9-nonanediol (external standard) contained in approximately 10 mL of anhydrous dimethylacetamide. Approximately 1 mL of each of these solutions was transferred to a gc vial, and treated with 0.150 ml of the silating agent trimethylsilylimidazole in order to determine and quantitate the components in each reaction tube by gas chromatographic analysis. The results of these experiments are presented in Table 1.

1. customseparate
2. customglass reaction tubes
3. customEach of these reaction tubes
4. customwas connected to a water trap
5. customInto each reaction tube was injected
6. customThe nitrogen purge into each tube
7. customAll of the reaction tubes
8. customonce into a 180° C.
9. customEach tube was pulled from the oil bath at different times
10. temperatureto cool
11. customthe reaction
12. customThe mass of the crude remaining in each tube
13. customfrom each separate reaction tube
14. customwere removed
15. additiondiluted with a weighed amount of 1,9-nonanediol (external standard)
16. additiontreated with 0.150 ml of the silating agent trimethylsilylimidazole in order
17. customThe results of these experiments

ORD record

ord-ad7b9b6fa4d44af292077f78cd855096

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06689892B2