Ethylene Oxide → Bis(2-hydroxyethyl) terephthalate

HRID 918114Notes

Reaction equation

HRID 918114 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([CH:16]1OCC[O:17]1)CC.[CH2:21]1[O:23][CH2:22]1>C([O-])(=O)C1C=CC(C([O-])=O)=CC=1.C([N+](CC)(CC)CC)C.C([N+](CC)(CC)CC)C>[C:1]([O:12][CH2:21][CH2:22][OH:23])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:13][CH2:16][OH:17])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 7489Terephthalic AcidHCID 1798322-Propyl-1,3-dioxolane

Product 1

HCID 13739Bis(2-hydroxyethyl) terephthalate

Reagents, catalysts & solvents 1

HCID 19591307Tetraethyl ammonium terephthalateCatalyst

Conditions

Temperature
155 °C

Procedure

A 3-liter autoclave is charged with 600 grams of crude terephthalic acid (3.61 moles), 1600 ml. of 2-propyldioxolane reaction medium, 0.11 mole of tetraethyl ammonium terephthalate catalyst and then purged with nitrogen. Liquid ethylene oxide (473 grams, 10.75 mole) is then pumped in and the reactor heated quickly to 155°C. by passing steam through internal coils. After about 31/2 minutes the reaction is terminated by pressuring the contents of the autoclave into a vessel where the ethylene oxide is flashed and then the unreacted terephthalic acid removed by filtration. Cooling of the filtrate to about 18°C. yields about 742 grams of crude bis(2-hydroxyethyl) terephthalate.

Workup

  1. custompurged with nitrogen
  2. customAfter about 31/2 minutes the reaction is terminated
  3. customthe unreacted terephthalic acid removed by filtration
  4. temperatureCooling of the filtrate to about 18°C.

Sources & evidence

ORD record
ord-ba6d303984584c57b5402f3698f81288
Source dataset
uspto-grants-1976_07
Patent number
US03969394

Reaction notes

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