Ethynediol
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| General | ||||||||||
| Surname | Ethynediol | |||||||||
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Dihydroxyacetylene |
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| Molecular formula | C 2 H 2 O 2 | |||||||||
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| Molar mass | 58.07 g mol −1 | |||||||||
| Physical state |
gaseous |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
Ethynediol is a chemical compound with the empirical formula C 2 H 2 O 2 . Ethynediol is unstable, but the tautomer glyoxal is stable.
Manufacturing
By passing carbon monoxide over molten potassium , Justus von Liebig came up with a substance with the molecular formula KCO in 1834, which he called carbon oxide potassium . The compound shown was the potassium salt of ethynediol. Only in the 1960s was it proven that the reaction carried out by Liebig produced a mixture of the potassium salt of ethynediol and the potassium salt of hexahydroxybenzene .
Free ethynediol was only detected in the gas phase by mass spectrometry in 1986 .
In 1995 the compound was established by photolysis of squaric acid in a solid argon matrix at 10 K.
Derivatives
Alkoxide derivatives
Although the diol is short-lived, the salts of the dianion [C 2 O 2 ] 2− are well known. In addition to the potassium salt produced by Liebig, the sodium , barium , strontium , lithium , rubidium and cesium salts have been produced over the years .
The ethynediolates can also be produced by reacting carbon monoxide with solutions of the metals in liquid ammonia at low temperatures. The potassium salt is a pale yellow solid that reacts explosively with air, halogens , halogenated hydrocarbons , alcohols and water .
Coordination links
Ethynediol forms coordination compounds such as [TaH (HOC≡COH) (dmpe) 2 Cl] + Cl - .
Other stable derivatives are the diethers of ethynediol.
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ^ WE Trout: The metal carbonyls. In: J. Chem. Educ. 1937, 14 (10), p. 453 ( doi: 10.1021 / ed014p453 ).
- ↑ WA Herrmann : 100 years of metal carbonyls. A chance discovery makes history. In: Chemistry in Our Time . 1988, 22nd year, No. 4, pp. 113-122 ( doi: 10.1002 / ciuz.19880220402 ).
- ↑ Werner Büchner, E. Weiss: On the knowledge of the so-called «alkali carbonyls» IV [1] About the reaction of molten potassium with carbon monoxide. In: Helvetica Chimica Acta , 47, 6, pp. 1415-1423 ( doi: 10.1002 / hlca.19640470604 ).
- ^ Johan K. Terlouw, Peter C. Burgers, Ben LM van Baar, Thomas Weiske, Helmut Schwarz: The Formation in the Gas Phase of HO-CC-OH, H 2 N-CC-NH 2 , H 2 N-CC- OH and related Compounds by Selective Reduction of their Cations , In: Chimia , 40, pp. 357-359. Online version. Retrieved June 21, 2014 .
- ^ Günther Maier, Christine Rohr: Ethynediol: Photochemical generation and matrix-spectroscopic identification. In: Liebigs Annalen , 1996, 3, pp. 307-309 ( doi: 10.1002 / jlac.199619960303 ).
- ↑ a b T. G. Pearson (1933), Carbonyls of Lithium, Rubidium and Cesium . In: Nature , 131, pp. 166-167 ( doi: 10.1038 / 131166b0 ).
- ↑ Raymond N. Vrtis, Ch. Pulla Rao, Simon G. Bott, and Stephen J. Lippard: Synthesis and Stabilization of Tantalum-Coordinated Dihydroxyacetylene from Two Reductively Coupled Carbon Monoxide Ligands In: J. Am. Chem. Soc. , 110, 22, pp. 7564-7566 ( doi: 10.1021 / ja00230a062 ).
- ↑ Anna Bou, Miquel A. Pericàs and Félix Serratosa (1981), Diisopropoxy- and di-tert-butoxyethyne: Stable acetylene diethers . In: Tetrahedron , 37, 7, pp. 1441-1449 ( doi: 10.1016 / S0040-4020 (01) 92464-0 ).