Ethylene Oxide → 3-Phenoxy-1,2-propanediol

HRID 5244

반응식

HRID 5244 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[O:26]1CC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br-].C([N+](CCC)(CCC)CCC)CC.C1(C)C=CC=CC=1>[O:5]([CH2:1][CH:2]([OH:4])[CH2:3][OH:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

7

반응물 4

HCID 6354Ethylene OxideHCID 7108PhenothiazineHCID 31217Phenyl glycidyl etherHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 108573-Phenoxy-1,2-propanediol

시약·촉매·용매 2

HCID 74745Tetrapropylammonium bromide촉매HCID 1140Toluene용매2회

실험 절차

A solution of 150.2 g. phenyl glycidyl ether (1.0 eq.), 200.0 g. AOnPA (1.15 eq., of Example 1), 200.0 g. toluene, 4.0 g. tetrapropylammonium bromide (0.015 eq.), and 1.0 g. phenothiazine was heated at reflux for 6.0 hours. Conversion, measured by residual oxirane titer, was ca. 93%. Upon cooling, the reactor was charged with 186.0 g. of the AOnPA (1.07 eq.), 150.0 g. toluene, and 10.0 g. p-toluenesulfonic acid monohydrate (0.05 eq.). The mixture was again heated at reflux. After 6.0 hrs., conversion was 90%. The product was extracted with ether and purified by washing. It had an acrylate titer of 3.8 meq./g. (theory: 4.17 meq./g.) and Brookfield viscosity of 230 centipoise at 25° C.

후처리

  1. temperatureat reflux for 6.0 hours
  2. temperatureUpon cooling
  3. additionthe reactor was charged with 186.0 g
  4. temperatureThe mixture was again heated
  5. temperatureat reflux
  6. extractionThe product was extracted with ether
  7. custompurified
  8. washby washing
  9. customat 25° C.

출처 및 근거

ORD 기록
ord-167fda6db42f40c2b04d4c02c0deb86d
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243069

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