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Succinimide

Succinimide Structure
CAS No.
123-56-8
Chemical Name:
Succinimide
Synonyms
SI;Pyrrolidine-2,5-dione;2,5-PYRROLIDINEDIONE;3,4-Dihydropyrrole-2,5-dione;Lubrizol 2153;succiminide;Succinic imide;Orotric;BUTANIMIDE;SUCCINIMIDE
CBNumber:
CB4852973
Molecular Formula:
C4H5NO2
Molecular Weight:
99.09
MOL File:
123-56-8.mol
MSDS File:
SDS
Modify Date:
2024/7/26 15:15:06

Succinimide Properties

Melting point 123-125 °C (lit.)
Boiling point 285-290 °C (lit.)
Density 1.41
vapor pressure <1 hPa (50 °C)
refractive index 1.4166 (estimate)
Flash point 201 °C
storage temp. Store below +30°C.
solubility 330g/l
pka 9.6(at 25℃)
form Powder or Flakes
color Off-white to beige to light brown
PH 4-6 (200g/l, H2O)
Odor nearly odorless
Water Solubility Soluble in water and ethanol. Insoluble in ether and chloroform.
Merck 14,8871
BRN 108440
InChIKey KZNICNPSHKQLFF-UHFFFAOYSA-N
LogP -0.85 at 20℃
CAS DataBase Reference 123-56-8(CAS DataBase Reference)
NIST Chemistry Reference 2,5-Pyrrolidinedione(123-56-8)
EPA Substance Registry System Succinimide (123-56-8)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  22-24/25-36-26-S24/25
WGK Germany  2
RTECS  WN2200000
TSCA  Yes
HS Code  29251995
Toxicity LD50 orally in rats: 14 g/kg (Melon)
NFPA 704
0
1 0

Succinimide price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) S9381 Succinimide 123-56-8 500G ₹6256.85 2022-06-14 Buy
Sigma-Aldrich(India) 8.07971 Succinimide for synthesis 123-56-8 250G ₹7070 2022-06-14 Buy
Sigma-Aldrich(India) 8.07971 Succinimide for synthesis 123-56-8 1KG ₹12470 2022-06-14 Buy
TCI Chemicals (India) S0108 Succinimide 123-56-8 25G ₹1800 2022-05-26 Buy
TCI Chemicals (India) S0108 Succinimide 123-56-8 500G ₹4900 2022-05-26 Buy
Product number Packaging Price Buy
S9381 500G ₹6256.85 Buy
8.07971 250G ₹7070 Buy
8.07971 1KG ₹12470 Buy
S0108 25G ₹1800 Buy
S0108 500G ₹4900 Buy

Succinimide Chemical Properties,Uses,Production

Chemical Properties

white crystalline powder

Uses

Succinimide is used in organic syntheses and in industrial silver plating processes. It is a reagent that is used in the synthesis of Lumiflavin (L473900), which is a toxic photolysis product of vitamin B2 (R415000). Further, it is used to form covalent bonds between proteins, peptides and plastics. In addition to this, it is used as an important raw material for the synthesis of heterocyclic compounds through N-acyliminium cyclizations.

Definition

ChEBI: Succinimide is a dicarboximide that is pyrrolidine which is substituted by oxo groups at positions 2 and 5. It is a pyrrolidinone and a dicarboximide.

Preparation

To a flask equipped with a dropping funnel, mechanical stirrer, and a 40 cm long side arm of not less than 10 mm inside diameter is added 236 gm (2.0 mole) of succinic acid. The flask is cooled and 270 ml (4.0 moles) of 28% aqueous ammonia is slowly added with stirring. The flask is rapidly heated with an oil bath until 200 ml of water distils. The temperature of the bath is rapidly raised to 275°C. Succinimide starts to distil over the range 275-289°C, to afford 168 gm of crude product which solidifies on cooling. The intermediate fraction, boiling between 102° and 275°C, is redistilled to afford 10.0 gm of crude succinimide, b.p. 275-289°C. The combined product (178 gm) is added to 178 gm of hot ethanol. The solution is cooled, the crystals filtered, washed with 25 ml of cold ethanol, and dried to afford 163-164 gm (82-83%), m.p. 123-125°C. Approximately 4-5 gm of additional product may be obtained by concen­trating the mother liquor.
Recent Japanese patents suggested inert aprotic solvents such as cyclic amides (e.g., N-methylpyrrolidone, N-acetyl-2-pyrrolidone, DMF, or tet-ramethylurea) and azeotroping solvents (e.g., toluene, 0-xylene, hexane, or pentane) or other high-boiling solvents (e.g., chlorobenzene or chlo-rotoluene) as dehydrating agents for the formation of imides from di­basic acids (e.g., 3- and/or 4) hydroxyphthalic acid with a large variety of diamines including diaminosiloxanes such as bis (3-aminopropyl)-tetra-methylsiloxane.
Preparation of Succinimide

Purification Methods

Crystallise the imide from EtOH (1mL/g) or water. [Beilstein 21 H 369, 21/9 V 438.]

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