Process for manufacturing chain-extended hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof
The present disclosure pertains to a process for preparing hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof. The process includes reacting diethanolamine with an amine-functional compound that includes at least two —NH— units of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups. The amine-functional compound includes at least one —NH—CH2-CH2-NH— unit wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound may be present in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties, in the presence of a carbon oxide delivering agent.
1. A process for preparing hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof comprising the step of reacting diethanolamine with an amine-functional compound comprising at least two —NH— units of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups, the amine-functional compound comprising at least one —NH—CH2-CH2-NH— unit wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound is present in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties, in the presence of a carbon oxide delivering agent, wherein
the molar ratio of amine-functional compound to diethanolamine is at least about 0.2:1,
the molar ratio of carbon oxide delivering agent to —NH—CH2-CH2-NH— units in the amine-functional compound is at least about 0.1:1,
the amino-functional compound and the carbon oxide delivering agent are not the same compound, and
the amine-functional compound comprises ethylenediamine (EDA), ethylene urea (EU), or a mixture thereof, and the reaction product comprises tetraethylenepentamine (TEPA) of the formula H2N—(CH2-CH2-NH-)p-H, wherein p is 4, wherein one or more —NH—CH2-CH2-NH— units is present as cyclic ethylene urea units and/or piperazine units, and wherein one or more ethyleneamines or ethylene urea derivatives thereof are connected to each other via a linear ethylene urea structure.
2. The process according to claim 1 , wherein the molar ratio of amine-functional compound to diethanolamine is at least about 0.5:1.
3. The process according to claim 1 , wherein the molar ratio of the carbon oxide delivering agent to —NH—CH2-CH2-NH— units in the amine-functional compound is from about 0.2:1 to about 3:1.
4. The process according to claim 1 , wherein diethanolamine is provided at least in part in a form of a CO adduct.
5. The process according to claim 1 , wherein the carbon oxide delivering agent includes carbon dioxide, and organic compounds which are condensation products of carbon dioxide and an organic compound that includes an amino group or a hydroxyl group.
6. The process according to claim 5 , wherein the carbon oxide delivering agent is selected from the group of carbon dioxide, carbon dioxide adducts of diethanolamine, and urea-derivatives of ethyleneamine compounds.
7. The process according to claim 1 , wherein at least two —NH— units in the amine-functional compound are selected from the group of primary amine groups and cyclic secondary amine groups.
8. The process according to claim 1 , wherein at least about 50% of CO is added in the form of CO adducts of diethanolamine and/or the amine-functional compound.
9. The process according to claim 1 , wherein the reaction product comprises ethyleneamines of a formula H2N—(CH2-CH2-NH-)p-H wherein p is at least 4 or derivatives thereof.
10. The process according to claim 1 , wherein the amine-functional compound comprises ethylenediamine (EDA).
11. A process for preparing hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof comprising the step of reacting diethanolamine with an amine-functional compound comprising at least two —NH— units of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups, the amine-functional compound comprising at least one —NH—CH2-CH2-NH— unit wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound is present in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties, in the presence of a carbon oxide delivering agent, wherein
the molar ratio of amine-functional compound to diethanolamine is at least about 0.2:1,
the molar ratio of carbon oxide delivering agent to —NH—CH2-CH2-NH— units in the amine-functional compound is at least about 0.1:1,
the amino-functional compound and the carbon oxide delivering agent are not the same compound,
the amine-functional compound comprises ethylenediamine (EDA), ethylene urea (EU), or a mixture thereof, and the reaction product comprises tetraethylenepentamine (TEPA) of the formula H2N—(CH2-CH2-NH-)p-H wherein p is 4, wherein one or more —NH—CH2-CH2-NH— units is present as cyclic ethylene urea units and/or piperazine units, and wherein one or more ethyleneamines or ethylene urea derivatives thereof are connected to each other via a linear ethylene urea structure, or
the amine-functional compound comprises diethylenetriamine (DETA), the urea adduct thereof (UDETA), or a mixture thereof, and the reaction product comprises hexaethyleneheptamine (HEHA) of the formula H2N—(CH2-CH2-NH-)p-H wherein p is 6, wherein one or more —NH—CH2-CH2-NH— units is present as a cyclic ethylene urea units and/or or piperazine units, and wherein one or more ethyleneamines or ethylene urea derivatives thereof are connected to each other via a linear ethylene urea structure.
12. A process for preparing hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof comprising the step of reacting diethanolamine with an amine-functional compound comprising at least two —NH— units of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups, the amine-functional compound comprising at least one —NH—CH2-CH2-NH— unit wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound is present in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties, in the presence of a carbon oxide delivering agent, wherein
the molar ratio of amine-functional compound to diethanolamine is at least about 0.2:1,
the molar ratio of carbon oxide delivering agent to —NH—CH2-CH2-NH— units in the amine-functional compound is at least about 0.1:1,
the amino-functional compound and the carbon oxide delivering agent are not the same compound,
the amine-functional compound comprises ethylenediamine (EDA), ethylene urea (EU), or a mixture thereof, and the reaction product comprises tetraethylenepentamine (TEPA) of the formula H2N—(CH2-CH2-NH-)p-H wherein p is 4, wherein one or more —NH—CH2-CH2-NH— units is present as cyclic ethylene urea units and/or piperazine units, and wherein one or more ethyleneamines or ethylene urea derivatives thereof are connected to each other via a linear ethylene urea structure, or
the amine-functional compound comprises piperazine (PIP) and the reaction product comprises hydroxyethyleneaminoethylpiperazine (HEAEPIP) and/or piperazinoethylaminoethylpiperazine (PEAEP).
13. The process according to claim 1 , further comprising the step of subjecting the reaction product to a CO removal reaction to convert urea adducts present therein into ethylene amines and/or ethanolamines.
14. The process according to claim 1 , wherein the molar ratio of amine-functional compound to diethanolamine is at least about 1:1.
15. The process according to claim 1 , wherein the molar ratio of amine-functional compound to diethanolamine is at least about 1.5:1.
16. The process according to claim 1 , wherein the molar ratio of amine-functional compound to diethanolamine is at least about 2:1.
17. The process according to claim 1 , wherein at least about 75% of CO is added in the form of CO adducts of diethanolamine and/or the amine-functional compound.
18. The process according to claim 1 , wherein at least about 90% of CO is added in the form of CO adducts of diethanolamine and/or the amine-functional compound.
19. The process according to claim 1 , wherein the amine-functional compound comprises ethylene urea (EU).