Acetone dicarboxylic acid

Structural formula
General
Surname	Acetone dicarboxylic acid
other names	Acetone-1,3-dicarboxylic acid; α, α'-acetone dicarboxylic acid; 3-oxopentanedioic acid; β-ketoglutaric acid;
Molecular formula	C 5 H 6 O 5
Brief description	colorless solid
External identifiers / databases
EC number	208-797-9
ECHA InfoCard	100.007.999
PubChem	68328
Wikidata	Q2823239
properties
Molar mass	146.10 g mol −1
Physical state	firmly
density	1.28 g cm −3
Melting point	132 ° C (decomposition)
solubility	soluble in water and ethanol; slightly soluble in ethyl acetate and ether; practically insoluble in chloroform;
Refractive index	1.392 (25 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-280-305 + 351 + 338-304 + 340-405-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Acetonedicarboxylic acid is a chemical compound from the group of carboxylic acids . It was discovered by Hans von Pechmann in 1884 .

Extraction and presentation

Acetone dicarboxylic acid, by decarbonylation of citric acid with fuming sulfuric acid are obtained in an ice / sodium chloride cooling bath.

It can also be prepared by hydrolysis of 1,3-dicyanoacetone, which can be obtained from 1,3-dichloroacetone and alkali metal cyanides, or from acetone and carbon dioxide.

properties

Acetonedicarboxylic acid is a colorless solid that is soluble in water and ethanol . When stored, it slowly breaks down into acetone and carbon dioxide . It decomposes rapidly during distillation, during heating or in the presence of mineral acids , metal salts or alkalis, the unstable acetoacetic acid being formed as an intermediate in all cases . Acetone dicarboxylic acid dissolved in water and iron (III) chloride give it a deep red-violet color, while in alcoholic solution it turns wine-red.

use

Acetondicarboxylic acid is used as a building block in organic chemistry. It is used in particular for the synthesis of heterocyclic rings and in the Weiss-Cook reaction , which involves the production of cis-bicyclo [3.3.0] octane-3,7-dione by reaction with diacyl (1,2-ketone). Its presence in human urine is used as a diagnostic test for the presence of harmful intestinal flora such as Candida albicans . Like all β-dicarbonyl compounds, acetone dicarboxylic acid forms with a variety of suitable metal ions, e.g. B. copper or iron ions , chelate-like metal complexes, which are suitable for the separation of heavy metal traces from fats, oils and petroleum products.

Individual evidence

^ ^A ^b ^c Roger Adams, HM Chiles, CF Rassweiler: Acetonedicarboxylic Acid In: Organic Syntheses . 5, 1941, p. 5, doi : 10.15227 / orgsyn.005.0005 ; Coll. Vol. 1, 1941, p. 10 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet Acetone-1,3-dicarboxylic acid, 97% from AlfaAesar, accessed on August 13, 2017 ( PDF )(JavaScript required) .
↑ ^a ^b The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 68 ( books.google.de ).
^ H. von Pechmann: Ueber die Acetondicarbonsäure . In: Reports of the German Chemical Society . tape 17 , no. 2 , 1884, p. 2542-2543 , doi : 10.1002 / cber.188401702177 .
↑ ^a ^b ^c alpha, alpha'-acetone dicarboxylic acid - Lexicon of Chemistry . ( Spektrum.de ).
↑ Arno Müller: On the knowledge of the formation of coumarins from citric acid and phenols . In: Reports of the German Chemical Society . tape 58 , no. 9 , 1925, pp. 2202–2209, here p. 2208 , doi : 10.1002 / cber.19250580947 .
↑ Werner Baumann, Bettina Herberg-Liedtke: Chemicals in metal processing: data and facts on environmental protection . Springer-Verlag, 2013, ISBN 978-3-642-61004-2 , p. 1286 ( books.google.de ).

[org-1] A ^b ^c Roger Adams, HM Chiles, CF Rassweiler: Acetonedicarboxylic Acid In: Organic Syntheses . 5, 1941, p. 5, doi : 10.15227 / orgsyn.005.0005 ; Coll. Vol. 1, 1941, p. 10 ( PDF ).

[Alfa-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet Acetone-1,3-dicarboxylic acid, 97% from AlfaAesar, accessed on August 13, 2017 ( PDF )(JavaScript required) .

[Yaws-3] The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 68 ( books.google.de ).

[4] H. von Pechmann: Ueber die Acetondicarbonsäure . In: Reports of the German Chemical Society . tape 17 , no. 2 , 1884, p. 2542-2543 , doi : 10.1002 / cber.188401702177 .

[spektrum-5] , alpha'-acetone dicarboxylic acid - Lexicon of Chemistry . ( Spektrum.de ).

[6] Arno Müller: On the knowledge of the formation of coumarins from citric acid and phenols . In: Reports of the German Chemical Society . tape 58 , no. 9 , 1925, pp. 2202–2209, here p. 2208 , doi : 10.1002 / cber.19250580947 .

[7] Werner Baumann, Bettina Herberg-Liedtke: Chemicals in metal processing: data and facts on environmental protection . Springer-Verlag, 2013, ISBN 978-3-642-61004-2 , p. 1286 ( books.google.de ).