Acetylenedicarboxylic acid

Structural formula
General
Surname	Acetylenedicarboxylic acid
other names	Butynedioic acid
Molecular formula	C 4 H 2 O 4
Brief description	beige solid
External identifiers / databases
EC number	205-536-0
ECHA InfoCard	100.005.033
PubChem	371
Wikidata	Q410634
properties
Molar mass	114.05 g mol −1
Physical state	firmly
density	0.55 g cm −3 (bulk density)
Melting point	180-185 ° C
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-315-319-335
	P: 261-301 + 310-305 + 351 + 338
Toxicological data	63 mg kg −1 ( LD 50 , mouse , oral )
Thermodynamic properties
ΔH f 0	−577.3 kJ / mol
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acetylenedicarboxylic acid is a chemical compound from the group of carboxylic acids . It is the simplest dicarboxylic acid with a C≡C triple bond.

Extraction and presentation

Acetylenedicarboxylic acid was first described in 1877 by the Polish chemist Ernest Bandrowski . It can be obtained by the dehydrobromination of α, β- dibromosuccinic acid with potassium hydroxide in methanol or ethanol . The reaction yields potassium bromide and the potassium salt of acetylenedicarboxylic acid, which is treated with sulfuric acid to produce acetylenedicarboxylic acid.

properties

Acetylenedicarboxylic acid is a beige solid that is soluble in water. The heat of decomposition determined by DSC is −154 kJ · mol ⁻¹ or −1355 kJ · kg ⁻¹ .

use

The diesters of acetylenedicarboxylic acid (e.g. dimethyl acetylenedicarboxylate ), which are used as intermediates for the preparation of heterocycles and as dienophiles in Diels-Alder reactions , are primarily used.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Acetylenedicarboxylic acid, 95% from Sigma-Aldrich , accessed on December 14, 2011 ( PDF ).
↑ ^a ^b ^c Data sheet acetylenedicarboxylic acid (PDF) from Merck , accessed on December 14, 2011.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.
↑ E. Bandrowski: Ueber Acetylenedicarboxylic acid , Chemical Reports, 1877, Volume 10, pp. 838-842.
↑ TW Abbott, Richard T. Arnold, Ralph B. Thompson: Acetylenedicarboxylic acid In: Organic Syntheses . 18, 1938, p. 3, doi : 10.15227 / orgsyn.018.0003 ; Coll. Vol. 2, 1943, p. 10 ( PDF ).
↑ Grewer, T .; Klais, O .: Exothermic decomposition - investigations of the characteristic material properties , VDI-Verlag, series "Humanisierung des Arbeitsleben", Volume 84, Düsseldorf 1988, ISBN 3-18-400855-X , p. 9.
^ Lexicon of Chemistry: Acetylenedicarboxylic acid

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet Acetylenedicarboxylic acid, 95% from Sigma-Aldrich , accessed on December 14, 2011 ( PDF ).

[Merck-2] Data sheet acetylenedicarboxylic acid (PDF) from Merck , accessed on December 14, 2011.

[CRC90_5_25-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.

[bandro-4] E. Bandrowski: Ueber Acetylenedicarboxylic acid , Chemical Reports, 1877, Volume 10, pp. 838-842.

[abbott-5] TW Abbott, Richard T. Arnold, Ralph B. Thompson: Acetylenedicarboxylic acid In: Organic Syntheses . 18, 1938, p. 3, doi : 10.15227 / orgsyn.018.0003 ; Coll. Vol. 2, 1943, p. 10 ( PDF ).

[Grewer-6] Grewer, T .; Klais, O .: Exothermic decomposition - investigations of the characteristic material properties , VDI-Verlag, series "Humanisierung des Arbeitsleben", Volume 84, Düsseldorf 1988, ISBN 3-18-400855-X , p. 9.

[7] Lexicon of Chemistry: Acetylenedicarboxylic acid