Succinimide

Structural formula
General
Surname	Succinimide
other names	2,5-pyrrolidinedione Succinic acid imide 3,4-dihydropyrrole-2,5-dione Butanimide
Molecular formula	C 4 H 5 NO 2
Brief description	beige solid
External identifiers / databases
CAS number 123-56-8 EC number 204-635-6 ECHA InfoCard 100.004.215 PubChem 11439 Wikidata Q419430
properties
Molar mass	99.08 g mol −1
Physical state	firmly
density	1.41 g cm −3
Melting point	123-125 ° C
boiling point	285-290 ° C
solubility	Easily soluble in water (240 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	14,000 mg kg −1 ( LD 50 ,  rat ,  oral )
Thermodynamic properties
ΔH f 0	−459.0 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Succinimide is a chemical compound from the group of carboximides and the imide of succinic acid .

history

Succinimide was discovered by Felix d'Arcet in 1835. The name is derived from the term "succinyl acid" for succinic acid.

Extraction and presentation

Succinimide is formed when ammonia gas is introduced into succinic anhydride . Alternatively, succinic acid can react directly with concentrated ammonia to form ammonium succinate, which is converted into succinimide by heating.

properties

Succinimide crystallizes in colorless rhombic tablets, which lose crystal water in the air. It is easily soluble in water and ethanol , but only slightly in ether . When heated above 287 ° C it begins to decompose. The flash point is 201 ° C. It reacts as a very weak acid , which is caused by the mesomerism of the group CO – NH – CO.

It reacts easily with iodine , bromine and chlorine to form N-iodosuccinimide , N-bromosuccinimide or N-chlorosuccinimide . Another derived compound is N-hydroxysuccinimide .

use

Succinimide is used as a starting material in a number of organic syntheses and in industrial silver coating processes.

The basic structure of succinimide is part of some chemical compounds that are used, among other things, as medicinal substances (for example, the anti- epileptic drugs ethosuximide , phensuximide and mesuximide ). Succinimides are also used to form covalent bonds between proteins or peptides and plastics.

The plastic polysuccinimide has the same structure in its repeating unit as succinimide, but is not made from the latter.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on succinimide in the GESTIS substance database of the IFA , accessed on December 22, 2019(JavaScript required) .
2. ↑ 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.
3. ↑ Edmund H. Miller: SUCCINIMID, J. Am. Chem. Soc. , 1894 , 16  (7), pp. 433-462; doi : 10.1021 / ja02105a001 .
4. ↑ Data sheet succinimide (PDF) from Merck , accessed on May 4, 2010.