ChemicalBook CAS DataBase List 1-(2-Aminoethyl)imidazolidin-2-one

1-(2-Aminoethyl)imidazolidin-2-one synthesis

10synthesis methods

Product Name:1-(2-Aminoethyl)imidazolidin-2-one
CAS Number:6281-42-1
Molecular formula:C5H11N3O
Molecular Weight:129.16

111-40-0

57-13-6

6281-42-1

693 kg (6.728 kmol) of diethylenetriamine (DETA) was added to a 1 m3 stirred reactor equipped with a double jacket, a liquid feed device, a nitrogen inerting system, a reaction vessel, and a scrubber tower for recovery of ammonia and ammonia solution. The reaction system was warmed up to 130°C while nitrogen was introduced to remove oxygen from the DETA. When the temperature reached 130 °C, slow addition of a 40% aqueous urea solution totaling 671.4 kg (4.476 kmol) was initiated, resulting in a molar ratio of DETA to urea of 1.5:1. The addition of the urea solution continued for a period of 4 h in batches. The ammonia released immediately at the beginning of the reaction was recovered through a scrubbing tower, and the scrubbing solution and the aqueous ammonia solution were collected in a special container. After the addition was completed, the reaction mixture was kept at 130°C for 1.5 hours to ensure complete water removal. Subsequently, the reaction temperature was gradually increased: first to 140 °C in 45 min and held for 45 min, then to 150 °C and held for 45 min, and finally at 160 °C for 5 h. The reaction temperature was then increased to 140 °C in 45 min and held for 45 min. At the end of the reaction, the system was cooled to 125 °C and the excess DETA was removed by distillation under a reduced pressure of 10 to 1.5 mbar and a mild nitrogen stream, a process that did not take more than 5 hours. After restoring the system to atmospheric pressure, it was cooled to 60 °C and the product was removed from the reactor. The resulting product contained 95-96% of 1-(2-aminoethyl)-2-imidazolidinone (UDETA) and 1-2.5% of tetraethyleneurea (TETU).

111-40-0
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57-13-6 Synthesis

57-13-6
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6281-42-1
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Yield: 96%

Reaction Conditions:

with ammonia at 125 - 160;Inert atmosphere;Large scale;Concentration;Temperature;

Steps:

1 Preparation of UDETA from DETA and Urea (R=1.5)
693 kg (6728 M) of DETA were introduced into a 1 m³stirred reactor which has a double jacket, a device for introducing liquid, a nitrogen inerting system, a container and a scrubbing column for recovering the ammonia gas and the aqueous ammoniacal liquors. The reaction medium was brought to 130° C. while at the same time performing nitrogen sparging so as to deoxygenate the DETA. When the temperature was reached, the introduction of an aqueous solution of urea at 40%, on the basis of 671.4 kg (4476 M), was begun. The DETA:urea molar ratio was therefore 1.5:1.[0045]The urea was introduced fractionwise over the course of 4 h.[0046]The release of ammonia, which appeared at soon as the running-in began, was scrubbed on the scrubbing column and the aqueous ammoniacal liquors were collected in the container. The reaction mixture was then kept at 130° C. for 1 h30 in order to finish off the removal of the water.[0047]The reaction medium was then gradually heated by bringing it: to 140° C. for 45 min, then to 150° C. for 45 min, then to 160° C. for 5 h. It was cooled to 125° C. at the end of the reaction, and then the excess DETA was removed under reduced pressure of from 10 to 1.5 mbar and with mild nitrogen sparging, for a maximum of 5 h. The product obtained after returning the equipment to atmospheric pressure, cooling to 60° C. and withdrawal from the reactor had a UDETA titer of 95-96% and contained 1-2.5% of TETU

References:

Arkema France;Baloche, Alain;Gamet, Jean-Paul;Gillet, Jean-Philippe US2013/23667, 2013, A1 Location in patent:Paragraph 0044; 0045; 0046; 0047

111-40-0
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616-38-6 Synthesis