Muconic acid

The muconic acid (hexa-2,4-diendisäure, butadiene-1,4-dicarboxylic acid) is an unsaturated dicarboxylic acid with conjugated π-electron system. Their different arrangement results in three diastereomers .

properties

The isomeric muconic acids are easily soluble in glacial acetic acid and very sparingly soluble in water. In an alkaline solution, muconic acid can be reduced to hex-3-endioic acid by sodium amalgam . ( E , E ) -muconic acid can be converted into a lactone with sulfuric acid, but this does not work with ( Z , Z ) -muconic acid. Because of its double bonds, the compound enters into a number of reactions and forms a number of derivatives such as lactones, sulfones, polyamides, polyesters and others.

Muconic acid
Surname	( E , E ) -muconic acid	( E , Z ) -Muconic acid	( Z , Z ) -Muconic acid
Structural formula
CAS number	3588-17-8	1119-73-9	1119-72-8
	505-70-4 (mixture of isomers)
PubChem	5356793	5280614	5280518
Molecular formula	C 6 H 6 O 4
Molar mass	142.11 g mol −1
Physical state	firmly
Brief description	colorless solid
Melting point	290 ° C		194-195 ° C
density	1.17 g cm −3		1.17 g cm −3
solubility	Easily soluble in glacial acetic acid and ethanol, very sparingly soluble in water
GHS labeling	Caution	no classification available	Caution
H and P phrases	315-319-335	see above	302-315-319-335
	no EUH phrases	see above	no EUH phrases
	261-305 + 351 + 338	see above	261-305 + 351 + 338

presentation

Muconic acid can be obtained by dehydrohalogenation of 3,4 -dihaloadipic acid with alkaline solutions or by oxidation of hexa-2,4-dienedial with peroxy acids . ( E , E ) -Muconic acid can be obtained from glucose with the help of bacteria such as Escherichia coli .

use

( E , E ) -Muconic acid is of physiological interest because it is excreted by the animal organism after the administration of benzene-containing foods.

Individual evidence

1. ↑ ^{a b c d} Spektrum.de: Muconsäure - Lexikon der Chemie , accessed on December 12, 2015
2. ↑ Houben-Weyl Methods of Organic Chemistry Vol. VI / 2, 4th Edition O-Metal Derivatives of Organic Hydroxy Compounds; Lactones . Georg Thieme Verlag, 2014, ISBN 3-13-180074-7 , p. 607 ( limited preview in Google Book search).
3. ^ Johannes Karl Fink: Reactive Polymers Fundamentals and Applications A Concise Guide to Industrial Polymers . William Andrew, 2013, ISBN 1-4557-3158-7 , pp. 399 ( limited preview in Google Book search).
4. ↑ Entry on muconic acids. In: Römpp Online . Georg Thieme Verlag, accessed on June 4, 2019.
5. ↑ ^{a b} Data sheet trans, trans-Muconic acid, 98% from Sigma-Aldrich , accessed on December 12, 2015 ( PDF ).
6. ↑ ^{a b} Data sheet cis, cis-Muconic acid, ≥97.0% (HPLC) from Sigma-Aldrich , accessed on December 12, 2015 ( PDF ).
7. ^ ^{A b} Carl L. Yaws: 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. 101 ( limited preview in Google Book search).
8. ↑ A. Albu, C. Anderson, I. Bang, F. Bottazzi, W. Caspari, S. Fränkel, Fr. Koppelsröder, L. Halberstaedter, A. Heffter, M. Jakoby, A. Loewy, P. Mayer, J Morgenroth, C. Neuberg, A. Pappenheim: The urine as well as the other excretions and body fluids of humans and animals, their examination and composition in normal and pathological condition Part I A manual for doctors, chemists and pharmacists as well as for use in agricultural research stations . Springer-Verlag, 2013, ISBN 978-3-642-91001-2 , pp. 280 ( limited preview in Google Book search).
9. ↑ Oliver Türk: Material use of renewable raw materials Basics - Materials - Applications . Springer-Verlag, 2013, ISBN 978-3-8348-2199-7 , pp. 458 ( limited preview in Google Book search).