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

HRID 5244

Reaction equation

HRID 5244 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 108573-Phenoxy-1,2-propanediol

Reagents, catalysts & solvents 2

HCID 74745Tetrapropylammonium bromideCatalystHCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-167fda6db42f40c2b04d4c02c0deb86d
Source dataset
uspto-grants-1993_09
Patent number
US05243069

Linked notes

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