Ацетооцтова кислота

Ацетооцтова кислота
Назва за IUPAC 3-оксобутанова кислота
Інші назви β-кетомасляна кислота
Ідентифікатори
Номер CAS [1] 541-50-4 [1]
DrugBank DB01762 Редагувати інформацію у Вікіданих
KEGG C00164 Редагувати інформацію у Вікіданих
ChEBI 15344 Редагувати інформацію у Вікіданих
SMILES CC(=O)CC(=O)O [1]
InChI 1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7) [1]
Номер Бельштейна 1747690 Редагувати інформацію у Вікіданих
Властивості
Молекулярна формула C4H6O3
Молярна маса 102,031694 г/моль [1]
Тпл 36,5 °C [1]
Розчинність (вода) 1000 г/л (20°C) [1]
Розчинність (діетиловий ефір) легко розчинний
Кислотність (pKa) 3,59 (0°C) [1]
Якщо не зазначено інше, дані наведено для речовин у стандартному стані (за 25 °C, 100 кПа)
Інструкція з використання шаблону
Примітки картки

Ацетооцтова кислота — це оксокислота з хімічною формулою H3C—CO—CH2—COOH. За звичайних умов є безбарвною кристалічною речовиною[1].

Хімічні властивості

Як і інші β-оксокислоти, ацетооцтова кислота є нестабільною. Дуже легко декарбоксилюється з утворенням ацетону[2]:

Ацетооцтовій кислоті властива кето-енольна таутомерія[3].

Частка енольної форми дуже сильно залежить від розчинника та коливається від 2% (гексафлуоропропан-2-ол) до 49% (карбон тетрахлорид) за температури 35 °С.[3]

Отримання

Ацетооцтова кислота утворюється при гідратації дикетену, який отримують з етенону[4]:

У лабораторії, ацетооцтову кислоту зазвичай отримують гідролізом етил ацетоацетату за низької температури та застосовують in situ.[5]

Примітки

  1. ↑ а б в г д е ж и Acetoacetic acid | C4H6O3 - PubChem. pubchem.ncbi.nlm.nih.gov (англійська) . Архів оригіналу за 13 серпня 2020.
  2. ↑ Нейланд (1990). Органическая химия (російська) . с. 636. ISBN 5-06-001471-1.
  3. ↑ а б Grande, Karen D.; Rosenfeld, Stuart M. (1980-04). Tautomeric equilibriums in acetoacetic acid. The Journal of Organic Chemistry (англ.). Т. 45, № 9. с. 1626—1628. doi:10.1021/jo01297a017. ISSN 0022-3263. Архів оригіналу за 2 листопада 2021. Процитовано 2 листопада 2021.
  4. ↑ Ластухін, Воронов (2006). Органічна хімія. Львів: Центр Європи. с. 497. ISBN 966-7022-19-6.
  5. ↑ Organic Syntheses Procedure. orgsyn.org (англ.). Архів оригіналу за 7 листопада 2021. Процитовано 7 листопада 2021.

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