Kyselina glyoxalová

Kyselina glyoxalová
Strukturní vzorec
Strukturní vzorec
Obecné
Systematický názevkyselina oxoethanová
Triviální názevkyselina glyoxalová
Ostatní názvykyselina formylmravenčí, kyselina glyoxylová
kyselina methanalkarboxylová, karboxylaldehyd
Anglický názevGlyoxylic acid
Německý názevGlyoxylsäure
Funkční vzorecCHOCOOH
Sumární vzorecC2H2O3
Identifikace
Registrační číslo CAS298-12-4
SMILESC(=O)C(=O)O
InChIInChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
Vlastnosti
Molární hmotnost74,04 g/mol
Teplota tání80 °C (353 K)
Teplota varu111 °C (384 K)
Hustota1,384 g/cm3
Disociační konstanta pKa3,18
Bezpečnost
GHS05 – korozivní a žíravé látky
GHS05
GHS07 – dráždivé látky
GHS07
[1]
Nebezpečí[1]
Není-li uvedeno jinak, jsou použity
jednotky SI a STP (25 °C, 100 kPa).
Některá data mohou pocházet z datové položky.

Kyselina glyoxalová, též kyselina glyoxylová, systematický název kyselina oxoethanová je nejjednodušší oxokyselina, obsahuje vedle sebe aldehydovou a karboxylovou skupinu. Jedná se o přechodnou sloučeninu mezi glyoxalem a kyselinou šťavelovou.

Společně s kyselinou octovou, glykolovou, šťavelovou a glycinem jde o jednu z dvouuhlíkatých karboxylových kyselin.

Výskyt a příprava

Konjugovaná báze této kyseliny se nazývá glyoxylát, jde o meziprodukt glyoxylátového cyklu.

Kyselina glyoxalová se vyrábí oxidací glyoxalu horkou kyselinou dusičnou (kdy vzniká také kyselina šťavelová) nebo ozonolýzou kyseliny maleinové.

V minulosti se vyráběla elektrosynteticky v roztoku kyseliny sírové za použití olověné katody a anody z oxidu olovičitého:[2][3][4]

Reakce a použití

Kyselina glyoxalová je asi desetkrát silnější než kyselina octová, její pKa je 3,32.

V přítomnosti zásady dochází k disproporcionaci:

2 OCHCOOH + H2O → HOCH2COOH + HOOC–COOH

Bezpečnost

Tato látka není výrazně jedovatá, smrtelná dávka pro krysy je asi 2,5 g/kg.

Reference

V tomto článku byl použit překlad textu z článku Glyoxylic acid na anglické Wikipedii.

  1. ↑ a b Glyoxylic acid. pubchem.ncbi.nlm.nih.gov [online]. PubChem [cit. 2021-05-23]. Dostupné online. (anglicky) 
  2. ↑ TAFEL, JULIUS; AND FRIEDRICHS, GUSTAV. Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung. Berichte der deutschen chemischen Gesellschaft. 1904, s. 3187-3191. Dostupné online [cit. 19 December 2013]. DOI 10.1002/cber.190403703116. 
  3. ↑ COHEN, Julius. Practical Organic Chemistry 2nd Ed.. London: Macmillan and Co. Limited, 1920. Dostupné online. S. 102-104. 
  4. ↑ François Cardarelli. Materials Handbook: A Concise Desktop Reference. [s.l.]: Springer, 2008. Dostupné online. ISBN 1-84628-668-9. S. 574. 

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