Sorbitol → Sorbitol glycidyl ether

HRID 373332

반응식

HRID 373332 반응식
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[OH:6][CH2:7][C@@H:8]([C@H:10]([C@@H:12]([C@@H:14]([CH2:16][OH:17])[OH:15])[OH:13])[OH:11])[OH:9]>[Sn](F)F>[CH2:1]([O:17][CH2:16][C@@H:14]([C@H:12]([C@@H:10]([C@@H:8]([CH2:7][OH:6])[OH:9])[OH:11])[OH:13])[OH:15])[CH:3]1[O:5][CH2:4]1

참가 물질

4

반응물 2

HCID 5780SorbitolHCID 7835Epichlorohydrin3회

생성물 1

HCID 54252585Sorbitol glycidyl ether

시약·촉매·용매 1

HCID 24550Stop촉매

반응 조건

온도
110 °C

실험 절차

A 750 ml reactor equipped with reflux condenser, thermometer, stirrer and metering device for epichlorohydrin is charged with 72.9 g (0.4 mol) of sorbitol and 1.25 g (0.008 mol) of tin difluoride in 88.5 g (0.957 mol) of epichlorohydrin, and the charge is heated to 110° C. Then, with stirring, 132.1 g (1.429 mol) of epichlorohydrin are added at a rate of 1.5 ml/min, while keeping the temperature at 110°-115° C. Stirring is continued for a further 8 hours at 125°-130° C. Excess epichlorohydrin is removed by distillation under a water jet vacuum and the residue is diluted with 441 g of methyl isobutyl ketone. With efficient stirring, 142.4 g (1.78 mol) of a 50% solution of sodium hydroxide are added dropwise over 1 hour and the reaction mixture is kept for another 2 hours at this temperature. The reaction mixture is neutralised by addition of dry ice and filtered, and the organic phase is dried over magnesium sulfate. The solvent is removed on a rotary evaporator and the residue is dried under vacuum (2 hours/60° C.), giving 155.2 g of sorbitol glycidyl ether for which the following analytical values are obtained: epoxy value: 5.5 eq/kg; total chlorine content 15.56%; hydrolysable chlorine content 1.09%; viscosity at 40° C.: 2460 mPa.s; average molecular weight Mn (GPC): 658.

후처리

  1. customA 750 ml reactor equipped
  2. temperaturewith reflux condenser
  3. customat 110°-115° C
  4. stirringStirring
  5. customExcess epichlorohydrin is removed by distillation under a water jet vacuum
  6. additionthe residue is diluted with 441 g of methyl isobutyl ketone
  7. additionWith efficient stirring, 142.4 g (1.78 mol) of a 50% solution of sodium hydroxide are added dropwise over 1 hour
  8. waitthe reaction mixture is kept for another 2 hours at this temperature
  9. additionThe reaction mixture is neutralised by addition of dry ice
  10. filtrationfiltered
  11. dry with materialthe organic phase is dried over magnesium sulfate
  12. customThe solvent is removed on a rotary evaporator
  13. customthe residue is dried under vacuum (2 hours/60° C.)

출처 및 근거

ORD 기록
ord-b3e233332f48425ea55d66e8103dd3ca
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162547

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