Water → Triethylene glycol di(1-hydroxyethyl) ether

HRID 377531

Reaction equation

HRID 377531 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH:13]=[CH2:14])=[CH2:2].C1(C)C=CC(S([O-])(=O)=[O:22])=CC=1.[NH+]1C=CC=CC=1.C(N(CC)CC)C.C(OC(Cl)C)C.[OH2:45]>O1CCCC1.C(OCC)(=O)C>[OH:45][CH:13]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH:1]([OH:22])[CH3:2])[CH3:14]

Participants

8

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 23478Ethane, 1-chloro-1-ethoxy-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 3033992Triethylene glycol divinyl ether

Product 1

HCID 88244959Triethylene glycol di(1-hydroxyethyl) ether

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The thus obtained partially hydroxypropylated polyhydroxystyrene, 90 g, was dissolved in 180 g of tetra-hydrofuran. With stirring under ice cooling, 2.3 g of triethylene glycol divinyl ether and then 1.8 g of pyridinium p-toluenesulfonate were added. Reaction was carried out for 6 hours at room temperature, 46.5 g of triethylamine and then 30.0 g of 1-chloroethyl ethyl ether were added, and reaction was carried out for a further 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 5) in which 31.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, and the alcoholic hydroxyl group moieties which had been introduced in an amount of 2.0 mol % formed ether bonds with alcoholic hydroxyl groups of triethylene glycol di(1-hydroxyethyl) ether to provide crosslinking.

Workup

  1. customThe thus obtained partially hydroxypropylated polyhydroxystyrene, 90 g
  2. customReaction
  3. customreaction
  4. waitwas carried out for a further 2 hours at room temperature
  5. customfollowed by separation
  6. washThe ethyl acetate layer was washed twice with 300 g of water
  7. concentrationconcentrated in vacuum
  8. dissolutionThe residue was dissolved in 300 g of methanol
  9. additionadded dropwise to 20 liters of water whereupon a powdery solid
  10. customprecipitated
  11. filtrationThe solid was collected by filtration
  12. washwashed with 20 liters of water
  13. customdried in vacuum at 40° C. for 24 hours
  14. additionthe alcoholic hydroxyl group moieties which had been introduced in an amount of 2.0 mol %

Sources & evidence

ORD record
ord-0469937e5bd246509598a2c90db6c037
Source dataset
uspto-grants-2000_02
Patent number
US06027854

Linked notes

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