# Acetylenediol

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**Acetylenediol**, or **ethynediol**, is a [chemical substance](/source/Chemical_substance) with formula HO−C≡C−OH (an [ynol](/source/Ynol)). It is the [diol](/source/Diol) of [acetylene](/source/Acetylene). Acetylenediol is unstable in the condensed phase, although its [tautomer](/source/Tautomerism) [glyoxal](/source/Glyoxal) (CHO)2 is well known.

## Detection

Acetylenediol was first observed in the gas-phase by [mass spectrometry](/source/Mass_spectrometry).[1] The compound was later obtained by [photolysis](/source/Photodissociation) of [squaric acid](/source/Squaric_acid) in a [solid argon matrix](/source/Matrix_isolation) at 10 K (−263 °C).[2] Recently, this molecule was synthesized in interstellar ice analogs composed of [carbon monoxide](/source/Carbon_monoxide) (CO) and [water](/source/Water) (H2O) upon exposure to energetic electrons and detected upon sublimation by isomer-selective photoionization [reflectron time-of-flight mass spectrometry](/source/Time-of-flight_mass_spectrometry#Reflectron_TOF).[3]

## Derivatives

### Alkoxide derivatives

Like the diol, most simple ether derivatives are labile. [Di-tert-butoxyacetylene](/source/Di-tert-butoxyacetylene) is however a distillable liquid.

### Acetylenediolate salts

Salts of the **acetylenediolate** (**ethynediolate**) dianion −O−C≡C−O− are known. They are not however prepared from ethynediol, but by the reduction of [carbon monoxide](/source/Carbon_monoxide). Potassium acetylenediolate (K2C2O2) was first obtained by [Liebig](/source/Justus_von_Liebig) in 1834, from the reaction of [carbon monoxide](/source/Carbon_monoxide) with metallic [potassium](/source/Potassium);[4] but for a long time the product was assumed to be "potassium carbonyl" (KCO). Over the next 130 years were described the "carbonyls" of [sodium](/source/Sodium) (Johannis, 1893), [barium](/source/Barium) (Gunz and Mentrel, 1903), [strontium](/source/Strontium) (Roederer, 1906), and [lithium](/source/Lithium), [rubidium](/source/Rubidium), and [caesium](/source/Caesium) (Pearson, 1933).[5] The reaction was eventually shown to yield a mixture of the potassium acetylenediolate K2C2O2 and potassium [benzenehexolate](/source/Benzenehexolate) K6C6O6.[6]

The structure of these salts was clarified only in 1963 by Büchner and Weiss.[7][8]

Acetylenediolates can also be prepared by the rapid reaction of CO and a solution of the corresponding metal in liquid [ammonia](/source/Ammonia) at low temperature.[5] Potassium acetylenediolate is a pale yellow solid that reacts explosively with air, halogens, halogenated hydrocarbons, alcohols, water, and any substance which possesses an acidic hydrogen.[9]

### Coordination complexes

Acetylenediol can form [coordination compounds](/source/Coordination_compound), such as [TaH(HOC≡COH)(dmpe)2Cl]+Cl− where dmpe is [bis(dimethylphosphino)ethane](/source/1,2-Bis(dimethylphosphino)ethane).[10]

Acetylenediolate and related anions such as [deltate](/source/Deltic_acid) C3O32- and [squarate](/source/Squarate) C4O42- have been obtained from carbon monoxide under mild conditions by reductive coupling of CO ligands in [organouranium complexes](/source/Organouranium_chemistry).[11]

## See also

- [Acetylenedicarboxylic acid](/source/Acetylenedicarboxylic_acid)
- [Ethynol](/source/Ethynol)
- [Ynol](/source/Ynol)

## References

1. Terlouw, Johan K.; Burgers, Peter C.; van Baar, Ben L. M.; Weiske, Thomas; Schwarz, Helmut (1986). ["The Formation in the Gas Phase of HO–CC–OH, H2N–CC–NH2, H2N–CC–OH and Related Compounds by Selective Reduction of Their Cations"](https://web.archive.org/web/20110719095453/http://www.chem.tu-berlin.de/Thomas.Weiske/Publikationen/Publikation0017/Text0017.HTML). *CHIMIA*. **40** (10): 357–359. [doi:10.2533/chimia.1986.357](https://doi.org/10.2533/chimia.1986.357). Archived from [the original](http://www.chem.tu-berlin.de/Thomas.Weiske/Publikationen/Publikation0017/Text0017.HTML) on 19 July 2011. Retrieved 2009-08-01.

1. Maier, Günther & Rohr, Christine (1995). "Ethynediol: Photochemical generation and matrix-spectroscopic identification". *Liebigs Annalen*. **1996** (3): 307–309. [doi:10.1002/jlac.199619960303](https://doi.org/10.1002/jlac.199619960303)

1. Wang, Jia; Turner, Andrew M.; Marks, Joshua H.; Zhang, Chaojiang; Kleimeier, N. Fabian; Bergantini, Alexandre; Singh, Santosh K.; Fortenberry, Ryan C.; Kaiser, Ralf I. (1 June 2024). "Preparation of Acetylenediol (HOCCOH) and Glyoxal (HCOCHO) in Interstellar Analog Ices of Carbon Monoxide and Water". *The Astrophysical Journal*. **967** (2): 79. [Bibcode:2024ApJ...967...79W](https://ui.adsabs.harvard.edu/abs/2024ApJ...967...79W). [doi:10.3847/1538-4357/ad3c3e](https://doi.org/10.3847/1538-4357/ad3c3e)

1. Justus Liebig (1834), Annalen der Chemie und Pharmacie, volume 11, p. 182. Cited by Raymond N. Vrtis et al. (1988), JACS p. 7564.

1. T. G. Pearson (1933), *Carbonyls of Lithium, Rubidium and Caesium*. Nature, volume 131, pp. 166–167 (4 February 1933). [doi:10.1038/131166b0](https://doi.org/10.1038/131166b0)

1. Werner Büchner, E. Weiss (1964) *Zur Kenntnis der sogenannten «Alkalicarbonyle» IV[1] Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid. Helvetica Chimica Acta*, Volume 47 Issue 6, Pages 1415–1423.[doi:10.1002/hlca.19640470604](https://doi.org/10.1002/hlca.19640470604)

1. Werner Büchner, E. Weiss (1963) *Zur Kenntnis der sogenannten «Alkalicarbonyle» I Die Kristallstruktur des Kalium-acetylendiolats, KOC≡COK*. Helvetica Chimica Acta, Volume 46 Issue 4, Pages 1121–1127. [doi:10.1002/hlca.19630460404](https://doi.org/10.1002/hlca.19630460404)

1. E. Weiss, Werner Büchner (1963), *Zur Kenntnis der sogenannten Alkalicarbonyle. II. Die Kristallstrukturen des Rubidium- und Caesium-acetylendiolats, RbOC≡CORb und CsOC≡COCs.* Zeitschrift für anorganische und allgemeine Chemie, Volume 330 Issue 5-6, Pages 251–258. [doi:10.1002/zaac.19643300504](https://doi.org/10.1002/zaac.19643300504)

1. Charles Kenneth Taylor (1982), *The Chemical Behavior of the Alkali Metal Acetylenediolates*. Thesis, Pennsylvania State University; also Technical Memo A642321, Penn State University Park Applied Research Lab. 227 pages.

1. Raymond N. Vrtis, Ch. Pulla Rao, Simon G. Bott, and Stephen J. Lippard (1988), *Synthesis and Stabilization of Tantalum-Coordinated Dihydroxyacetylene from Two Reductively Coupled Carbon Monoxide Ligands* J. Am. Chem. Soc., volume 110 issue 22, pp. 7564–7566. [doi:10.1021/ja00230a062](https://doi.org/10.1021/ja00230a062)

1. Alistair S. Frey, F. Geoffrey N. Cloke, Peter B. Hitchcock (2008), *Mechanistic Studies on the Reductive Cyclooligomerisation of CO by U(III) Mixed Sandwich Complexes; the Molecular Structure of [(U(η-C8H6{Si'Pr3-1,4}2)(η-Cp*)]2(μ-η1:η1-C2O2)* Journal of the American Chemical Society, volume 130, issue 42, pages 13816–13817. [doi:10.1021/ja8059792](https://doi.org/10.1021/ja8059792)

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