The Reaction of Terephthalic Acid with Ethylene Oxide in the Presence of Amines

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Other Title
  • アミン存在下におけるテレフタル酸とエチレンオキシドとの皮応
  • アミン存在下におけるテレフタル酸とエチレンオキシドとの反応

Description

The reaction of terephthalic acid (TPA) with ethylene oxide (EO) in the presence of various amines was studied in organic solvents at various temperatures. Main reaction products were found to vary with reaction temperatures; (2-hydroxyethyl)triethylammonium hydrogen tere- phthalate, (2-hydroxyethyl)triethylammonium 2-hydroxyethyl terephthalate, and bis (2-hydro xyethyl) terephthalate were obtained in excellent yields at 50°C, 70°C, and 90°C, respectively, when the reaction was carried out in the presence of equivalent triethylamine in tetrahydro- furan or acetone.<BR>Studies on the reaction products and kinetics showed that the actual catalyst for the esteri fication of TPA with EO was not an amine itself but a quaternary ammonium terephthalate formed from TPA, EO, and amine.<BR>The rate of quaternization of amines was markedly affected by their molecular structures. Trialkylamines were quickly converted into the corresponding quaternary ammonium salts at an early stage of the reaction but the quaternization of primary or secondary amine was slow.<BR>The rate of esterification of TPA with EO was investigated in the presence of catalytically sufficient amounts of quaternary ammonium terephthalates obtained from primary, secondary, and tertiary amines, and it was found that these ammonium salts have almost the same cata lytic effect. Therefore, it was found that for the esterification of TPA the process of catalyst formation from amines, TPA, and EO is most important.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1977 (10), 1505-1511, 1977-10-10

    The Chemical Society of Japan

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