Sulfuric Acid → Isosorbide

1.548 g (8.5 mol) of sorbitol, 3,000 ml of xylene and 20 ml of concentrated sulfuric acid were heated to reflux with stirring and about 306 ml of water were removed. The xylene was then removed by distillation (the last amount under vacuum) and the residue was taken up in 3,000 ml of tert.-butanol, heated to 55° to 65° C., 2,432 ml (30.4 mol) of an aqueous solution of sodium hydroxide and 2,682 g (21.25 mol) of dimethyl sulfate were added dropwise simultaneously at this temperature while keeping the mixture always alkaline. When the addition is completed, the mixture was stirred for three hours at 60° C. and the alcohol was then removed up to a distillation temperature of 97° to 98° C. The residue was taken up in 8,500 ml of water and the aqueous solution was extracted three times with 1,000 ml portions of ethylene chloride. The solvent was evaporated from the combined organic phases and was fractioned in a column to recover the fraction in the boiling range of 118° to 120° C. mbar which was 1,037 g (70% yield) of dimthyl isosorbide.

1. temperatureto reflux
2. customabout 306 ml of water were removed
3. customThe xylene was then removed by distillation (the last amount under vacuum) and the residue
4. temperatureheated to 55° to 65° C.
5. additionWhen the addition
6. stirringthe mixture was stirred for three hours at 60° C.
7. customthe alcohol was then removed up to a distillation temperature of 97° to 98° C
8. extractionthe aqueous solution was extracted three times with 1,000 ml portions of ethylene chloride
9. customThe solvent was evaporated from the combined organic phases
10. customto recover the fraction in the boiling range of 118° to 120° C. mbar which

ORD 기록

ord-d28e7c5329dc48668c3d24bf4e4459ae

출처 데이터셋

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04659846