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Org. Synth. 1936, 16, 75
DOI: 10.15227/orgsyn.016.0075
SUCCINIMIDE
Submitted by H. T. Clarke and Letha Davies Behr.
Checked by W. H. Carothers and W. L. McEwen.
1. Procedure
In a 1-l. distilling flask, fitted with a side arm 40 cm. in length and not less than 10 mm. in internal diameter (Note 1), is placed 236 g. (2 moles) of succinic acid. To this is added slowly, with cooling and shaking, 270 cc. (243 g., 4 moles) of 28 per cent aqueous ammonia (sp. gr. 0.90). Most of the acid dissolves, forming a clear solution. The flask is set for downward distillation, and a water-cooled 500-cc. distilling flask is attached to the side arm. Provision may be made for removal of ammonia from the side tube of the receiver. The mixture is heated gently over a free flame; solution takes place rapidly, and a small amount of uncombined ammonia passes over with the first portions of the distillate. The temperature of the vapor rises to 100° and remains at this point until about 200 cc. of water has distilled. The flame is then increased, and the ammonium succinate begins to decompose with evolution of ammonia; the temperature of the vapor falls to 97° during the distillation of the next 30 cc. When the vapor temperature has risen to 102°, the receiver is changed and an intermediate fraction collected from 102° to 275°. Succinimide then distils and is collected over the range 275–289°, largely at 285–289°. Decomposition takes place to a small extent with formation of a black tar; the distillation is stopped when the tarry residue begins to decompose with evolution of yellow fumes.
The crude succinimide, which solidifies completely, amounts to about 168 g. The intermediate fraction is redistilled from a smaller flask and furnishes about 10 g. more of crude succinimide boiling between 275° and 289°. The two portions of crude succinimide are combined and crystallized from 95 per cent ethyl alcohol, employing 1 cc. of solvent for every gram of product. If the mixture is chilled to 0° for some hours before filtration and about 25 cc. of cold alcohol is employed for washing the crystals, the first crop amounts to 163–164 g. (82–83 per cent of the theoretical amount). On concentrating the mother liquor to one-third of its volume, a second crop of 4–5 g. can be secured (Note 2). The product melts at 123–125° and contains no water of crystallization.
2. Notes
1. It is essential to employ a side arm of at least this diameter in order to avoid clogging by crystals of succinimide when this first passes over.
2. A further small quantity of a less pure product can be obtained by evaporating the dark mother liquor to dryness and recrystallizing the residue from fresh 95 per cent alcohol.
3. Discussion
Succinimide has usually been prepared by heating succinic acid in a current of ammonia1, 2 or by distilling ammonium succinate.1, 3
This preparation is referenced from:

References and Notes
  1. Fehling, Ann. 49, 198 (1844).
  2. Franchimont and Friedmann, Rec. trav. chim. 25, 79 (1906).
  3. Bunge, Ann. Suppl. 7, 118 (1870); Menschutkin, Ann. 162, 166 (1872).

Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)

ethyl alcohol,
alcohol (64-17-5)

ammonia (7664-41-7)

Succinic acid (110-15-6)

Succinimide (123-56-8)

ammonium succinate