IP Library Granted Patent US 11,919,866
Granted Patent B2
US 11,919,866 · App. 16/638,347 · Granted Mar 5, 2024

Process for preparing cyclic alkylene ureas

Inventors: Antoon Jacob Berend Ten Kate (Arnhem, NL); Karl Fredrik Lake (Södertälje, SE); Michiel Jozef Thomas Raaijmakers (Deventer, NL); Rolf Krister Edvinsson (Partille, SE); Jenny Valborg Therese Adrian Meredith (Årsta, SE); Rens Veneman (Amersfoort, NL); Hendrik Van Dam (Ede, NL); Eike Nicolas Kantzer (Uddevalla, SE); Ina Ehlers (Stenungsund, SE); Slavisa Jovic (Utrecht, NL)
Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
C07D233/34
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Quick Facts
Patent No.
US 11,919,866
App. No.
16/638,347
Granted
Mar 5, 2024
Kind
B2
Abstract

A process for producing a cyclic alkylene urea product of Formula I: in which a compound of Formula II and/or Formula III is contacted in a reaction zone with a compound of Formula IV and/or Formula V and in the presence of one or more carbonyl delivering compounds; wherein the compound of Formula II and/or the compound of Formula III are added to a reaction zone comprising compound of Formula IV and/or compound of Formula (V) continuously or semi-continuously over a period of time, or in two or more batches.

Claims (12)

1. A process for producing 1-(2-aminoethyl) imidazolidin-2-one (UDETA), the process comprising:

contacting 2-oxazolidinone (CMEA) and/or monoethanolamine (MEA) in a reaction zone with ethyleneurea (EU) and/or ethylenediamine (EDA) and in the presence of one or more carbonyl delivering compounds;

wherein the ethyleneurea (EU) and/or the ethylenediamine (EDA) is present in a reaction zone, and wherein the 2-oxazolidinone (CMEA) and/or the monoethanolamine (MEA) are added to the reaction zone semi-continuously or in two or more batches.

2. The process of claim 1 , wherein the 2-oxazolidinone (CMEA) and/or the monoethanolamine (MEA) are added to the reaction zone semi-continuously.

3. The process of claim 1 , wherein the 2-oxazolidinone (CMEA) and/or the monoethanolamine (MEA) are added to the reaction zone in two or more batches.

4. The process of claim 1 , further comprising limiting an amount of CMEA and MEA and EU and EDA in the reaction zone to a predetermined molar ratio of CMEA and MEA to EU and EDA, wherein the predetermined molar ratio is 0.60:1.

5. The process of claim 1 , further comprising limiting an amount of CMEA and MEA and EU and EDA in the reaction zone to a predetermined molar ratio of CMEA and MEA to EU and EDA, wherein the predetermined molar ratio is 0.30:1.

6. The process of claim 1 , further comprising limiting an amount of CM EA and MEA and EU and EDA in the reaction zone to a predetermined molar ratio of CMEA and MEA to EU and EDA, wherein the predetermined molar ration is 0.25:1.

7. The process of claim 1 , further comprising limiting an amount of CM EA and MEA and EU and EDA in the reaction zone to a predetermined molar ratio of CMEA and MEA to EU and EDA, wherein the predetermined molar ration is 0.20:1.

8. The process of claim 1 , further comprising limiting an amount of CM EA and MEA and EU and EDA in the reaction zone to a predetermined molar ratio of CMEA and MEA to EU and EDA, wherein the predetermined molar ration is 0.16:1.

9. The process of claim 1 , wherein the carbonyl delivering compound is selected from carbon dioxide; inorganic carbonic acid salts; cyclic and non-cyclic carbonic acid esters; urea; optionally substituted alkyl ureas; optionally substituted cyclic alkylene ureas; carbamic acids; carbamic acid salts; and cyclic and non-cyclic carbamic acid esters.

10. The process of claim 1 , wherein the carbonyl delivering compound is selected from 2-oxazolidinone (CMEA) and ethylenediamine (EDA).

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2020
From: TEN KATE, ANTOON JACOB BEREND; RAAIJMAKERS, MICHIEL JOZEF THOMAS; EDVINSSON, ROLF KRISTER; VENEMAN, RENS; VAN DAM, HENDRIK; KANTZER, EIKE NICOLAS; EHLERS, INA; JOVIC, SLAVISA
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 052320/0292 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2020
From: LAKE, KARL FREDRIK; MEREDITH, JENNY VALBORG THERESE ADRIAN
To: RISE RESEARCH INSTITUTES OF SWEDEN AB; SURFACE, PROCESS AND FORMULATION
Reel/Frame 052320/0506 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2020
From: RISE RESEARCH INSTITUTES OF SWEDEN AB; SURFACE, PROCESS AND FORMULATION
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 052320/0607 →
CHANGE OF NAME Recorded Apr 6, 2020
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 052320/0688 →
Priority Claims (1)
EP 17186004 · Aug 11, 2017 · regional
Continuity (1)
Related Publication 20200223800A1 · Jul 16, 2020