Process for manufacturing a cyclic urea adduct of an ethyleneamine compound

Patent metadata

Field	Value
Publication number	US-11292769-B2
Application number	US-201816615758-A
Country	US
Kind code	B2
Filing date	May 18, 2018
Priority date	May 23, 2017
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

Methods are provided for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethyleneamine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1. It has been found that the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof leads to a substantial increase of the reaction rate as compared to a process wherein the auxiliary compound is not present.

First claim

The invention claimed is:

1. A method for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the method comprises:
reacting the ethyleneamine compound with CO 2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1.

2. The method according to claim 1 , wherein the ethyleneamine compound is selected from diethylenetriamine (DETA), triethylenetetramine (L-TETA), aminoethylethanolamine (AEEA), and hydroxyethyldiethylenetriamine (HE-DETA).

3. The method according to claim 1 , wherein the molar ratio of auxiliary compound to amine compound is at least 0.05:1.

4. The method according to claim 1 , wherein the reaction is carried out at a temperature of at least 120° C. and at most 400° C.

5. The method according to claim 1 , wherein the molar ratio between CO2 and —NH—CH2-CH2-NH— moieties in the amine compound is at least 0.5:1 and at most 500:1.

6. The method according to claim 1 , wherein the reaction time is at most 10 hours.

7. A method to prepare ethylene amines or cyclic urea adducts thereof, the method comprising the steps of
a) manufacturing a cyclic urea adduct of an ethylene amine compound, the ethylene amine compound being selected from the group of ethylene amines and hydroxyethyl ethylene amines and comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethylene amine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylene diamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1, and
b1) where the cyclic urea adduct of an ethylene amine compound is a cyclic urea adduct of ethylene amine, reacting the cyclic urea adduct of ethylene amine with an ethanolamine-functional compound, or a urea- or carbamate additive thereof, or
b2) where the cyclic urea adduct of an ethylene amine compound is a cyclic urea adduct of a hydroxyethyl ethyleneamine, reacting the cyclic urea adduct of a hydroxyethyl ethyleneamine with a ethylene amine compound, or a urea- or carbamate additive thereof.

8. The method according to claim 7 , which comprises the steps of
a) manufacturing a cyclic urea adduct of an ethylene amine compound, the ethylene amine compound being selected from the group of ethylene amines comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethylene amine compound is reacted with CO 2 in the presence of monoethanolamine (MEA), the molar ratio of monoethanolamine to amine compound being at least 0.02:1, and
b) reacting the cyclic urea adduct of ethylene amine with monoethanolamine or the carbamate derivative thereof.

9. The method according to claim 8 , wherein the molar ratio of monoethanolamine to amine compound is at least 0.1:1.

10. The method according to claim 8 , wherein step b, b1, or b2 is performed at a temperature of at least 100° C. and lower than 400° C.

11. The method according to claim 7 , which comprises the steps of
a) manufacturing a cyclic urea adduct of an ethylene amine compound, the ethylene amine compound being selected from the group of hydroxyethyl ethylene amines comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethylene amine compound is reacted with CO 2 in the presence of ethylene diamine (EDA), the molar ratio of ethylene diamine to amine compound being at least 0.02:1, and
b) reacting the cyclic urea adduct of hydroxyethyl ethylene amine with ethylene diamine or the urea derivative thereof.

12. The method according to claim 11 , wherein the molar ratio of ethylene diamine to amine compound is at least 0.1:1.

13. The method according to claim 7 wherein the ethylene amine compound is selected from diethylenetriamine (DETA), triethylenetetramine (TETA), aminoethylethanolamine (AEEA), and hydroxyethyldiethylenetriamine (HE-DETA).

14. The method according to claim 7 , wherein step a) is carried out at a temperature of at least 120° C. and at most 400° C.

15. The method according to claim 7 , wherein the reaction time in step a) is at most 10 hours and at least 5 minutes.

Assignees

• Nouryon Chemicals Int Bv

Inventors

• Lake Karl Fredrik
• Kantzer Eike Nicolas
• Edvinsson Rolf Krister
• Ehlers Ina
• Van Dam Hendrik
• Adrian Meredith Jenny Valborg Therese
• Hagberg Lars Torbjörn
• Ten Kate Antoon Jacob Berend
• Veneman Rens
• Raaijmakers Michiel Jozef Thomas
• Jovic Slavisa

Classifications

• C07D233/36 Primary

  with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms · CPC title

• C07D233/32 Primary

  One oxygen atom · CPC title

• C07D233/34 Primary

  Ethylene-urea · CPC title