112-57-2

Usage

Uses

Used in Chemical Industry:
1,4,7,10,13-Pentaazatridecane is used as a solvent for sulfur, acid gases, and various resins and dyes due to its ability to dissolve these substances effectively.
Used in Manufacturing Industry:
1,4,7,10,13-Pentaazatridecane is used as a saponifying agent for acidic materials, which helps in the production of soaps and detergents.
Used in Rubber Industry:
1,4,7,10,13-Pentaazatridecane is used in the manufacture of synthetic rubber, contributing to the development of various rubber products.
Used in Automotive Industry:
1,4,7,10,13-Pentaazatridecane is used as a dispersant in motor oils, enhancing the performance and longevity of the oil.
Used in Oil Industry:
1,4,7,10,13-Pentaazatridecane is used as an intermediate for oil additives, improving the properties and performance of various oil products.

Air & Water Reactions

Soluble in water. Hygroscopic.

Reactivity Profile

1,4,7,10,13-Pentaazatridecane is hygroscopic. 1,4,7,10,13-Pentaazatridecane can react with oxidizing materials and strong acids. 1,4,7,10,13-Pentaazatridecane may attack some forms of plastics.

Hazard

Strong irritant to eyes and skin.

Health Hazard

Inhalation may cause nausea and slight irritation; compound is a sensitizer, and prolonged contact may cause asthma. Ingestion can cause burns of mouth, esophagus, and possibly stomach. Contact with eyes or skin may cause burns. Repeated skin contact may cause dermatitis.

Fire Hazard

Special Hazards of Combustion Products: Ammonia and toxic oxides of nitrogen may form in fires.

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by skin contact. Mutation data reported. A corrosive irritant to skin, eyes, and mucous membranes. Combustible when exposed to heat or flame. Can react with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Tetraethylenepentamine is used as a solvent for resins and dyes, in manufacture of synthetic rubber; and intermediate for oil additives; in papermaking.

Shipping

UN2320 Tetraethylenepentamine, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Distil the amine under vacuum. Also purify via its penta hydrochloride, nitrate or sulfate. Jonassen, Frey and Schaafsma [J Phys Chem 61 504 1957] cooled a solution of 150g of the base in 300mL of 95% EtOH, and added dropwise 180mL of conc HCl, keeping the temperature below 20o. The white precipitate was filtered off, crystallised three times from EtOH/water, then washed with diethyl ether and dried by suction. Reilley and Holloway [J Am Chem Soc 80 2917 1958], starting with a similar solution cooled to 0o, added slowly (keeping the temperature below 10o) a solution of 4.5g-moles of HNO3 in 600mL of aqueous 50% EtOH (also cooled to 0o). The precipitate was filtered by suction, recrystallised five times from aqueous 5% HNO3, then washed with acetone and absolute EtOH and dried at 50o. [For purification via the sulfate see Reilley and Vavoulis (Anal Chem 31 243 1959), and for an additional purification step using the Schiff base with benzaldehyde see Jonassen et al. J Am Chem Soc 79 4279 1957]. [Beilstein 4 IV 1244.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. This chemical is strongly alkaline; reacts with acids.

InChI:InChI=1/C8H23N5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h11-13H,1-10H2/p+5

Synthetic route

1,2-dichloro-ethane (107-06-2) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3)

Conditions	Yield
With ammonia

1,5-diamino-3-azapentane (111-40-0) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With ammonia; water; 1,2-dichloro-ethane unter Druck;

ethyleneimine (151-56-4) + triethylentetramine (112-24-3) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + tris(2-aminoethyl)-N,N,N'-ethyldiamine (31295-46-2)

Conditions	Yield
With hydrogenchloride In water at 25℃; Kinetics; Thermodynamic data; acid-catalyzed ring opening reactions at various temperature, Ea, ΔH are given;
With hydrogenchloride In water at 55℃;	A 64.5 % Chromat. B 35.5 % Chromat.
With hydrogenchloride In water at 35℃;	A 61.4 % Chromat. B 38.6 % Chromat.

1-<2-<(2-aminoethyl)amino>ethyl>aziridine (23435-23-6) + ethylenediamine (107-15-3) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With hydrogen cation In water at 40 - 60℃; Rate constant; Thermodynamic data; Ea, ΔH;
With hydrogen cation In water

{COFeC8H23N5}(2+) (46467-99-6) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
In water in acidic medium;
In water in acidic medium;

diethylenetriaminediacetonitrile (1051939-66-2) → 1-<2-(2-aminoethyl)aminoethyl>piperazine (24028-46-4) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With hydrogen; Cr-doped Raney cobalt In tetrahydrofuran at 120℃; under 75007.5 Torr; for 3h; Product distribution / selectivity; Autoclave;

1,2-dichloro-ethane (107-06-2) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
Stage #1: 1,2-dichloro-ethane With ammonia Stage #2: With sodium hydroxide Product distribution / selectivity;
With ammonium hydroxide at 140℃; under 105011 Torr;

1,2-dichloro-ethane (107-06-2) → piperazine (110-85-0) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonium hydroxide In water at 120℃; under 90009 Torr; Concentration;

1,2-dichloro-ethane (107-06-2) → piperazine (110-85-0) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonium hydroxide; ethylenediamine In water at 100℃; under 18751.9 Torr;

ethanolamine (141-43-5) → piperazine (110-85-0) + 1-(2-hydroxyethyl)piperazine (103-76-4) + aminoethylpiperazine (140-31-8) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonia; hydrogen In water at 92℃; under 26463 Torr; Temperature;

ethylenediamine (107-15-3) + 2,2'-iminobis[ethanol] (111-42-2) → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With imidazolidone at 270℃; for 5h; Inert atmosphere;

1,2-dichloro-ethane (107-06-2) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3)

Conditions	Yield
With ammonia

1,5-diamino-3-azapentane (111-40-0) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With ammonia; water; 1,2-dichloro-ethane unter Druck;

ethyleneimine (151-56-4) + triethylentetramine (112-24-3) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + tris(2-aminoethyl)-N,N,N'-ethyldiamine (31295-46-2)

Conditions	Yield
With hydrogenchloride In water at 25℃; Kinetics; Thermodynamic data; acid-catalyzed ring opening reactions at various temperature, Ea, ΔH are given;
With hydrogenchloride In water at 55℃;	A 64.5 % Chromat. B 35.5 % Chromat.
With hydrogenchloride In water at 35℃;	A 61.4 % Chromat. B 38.6 % Chromat.

1-<2-<(2-aminoethyl)amino>ethyl>aziridine (23435-23-6) + ethylenediamine (107-15-3) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With hydrogen cation In water at 40 - 60℃; Rate constant; Thermodynamic data; Ea, ΔH;
With hydrogen cation In water

{COFeC8H23N5}(2+) (46467-99-6) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
In water in acidic medium;
In water in acidic medium;

diethylenetriaminediacetonitrile (1051939-66-2) → 1-<2-(2-aminoethyl)aminoethyl>piperazine (24028-46-4) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With hydrogen; Cr-doped Raney cobalt In tetrahydrofuran at 120℃; under 75007.5 Torr; for 3h; Product distribution / selectivity; Autoclave;

1,2-dichloro-ethane (107-06-2) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
Stage #1: 1,2-dichloro-ethane With ammonia Stage #2: With sodium hydroxide Product distribution / selectivity;
With ammonium hydroxide at 140℃; under 105011 Torr;

1,2-dichloro-ethane (107-06-2) → piperazine (110-85-0) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonium hydroxide In water at 120℃; under 90009 Torr; Concentration;

1,2-dichloro-ethane (107-06-2) → piperazine (110-85-0) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonium hydroxide; ethylenediamine In water at 100℃; under 18751.9 Torr;

ethanolamine (141-43-5) → piperazine (110-85-0) + 1-(2-hydroxyethyl)piperazine (103-76-4) + aminoethylpiperazine (140-31-8) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonia; hydrogen In water at 92℃; under 26463 Torr; Temperature;

ethylenediamine (107-15-3) + 2,2'-iminobis[ethanol] (111-42-2) → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With imidazolidone at 270℃; for 5h; Inert atmosphere;

2-oxo-imidazolidine-1-ethanol (3699-54-5) + 2-aminoethylimidazolidone (6281-42-1) + 1,5-diamino-3-azapentane (111-40-0) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
Stage #1: 2-oxo-imidazolidine-1-ethanol; 2-aminoethylimidazolidone; 3-azapentane-1,5-diamine at 270℃; under 3375.34 - 10501.1 Torr; for 9h; Autoclave; Inert atmosphere; Stage #2: With water; sodium hydroxide at 200℃; under 2550.26 Torr; for 4h; Autoclave; Inert atmosphere;

2-oxo-imidazolidine-1-ethanol (3699-54-5) + 1,5-diamino-3-azapentane (111-40-0) → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
at 270℃; under 2475.25 - 7125.71 Torr; for 6h; Autoclave; Inert atmosphere;

U1TEPA → N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
Stage #1: U1TEPA With water at 235 - 270℃; under 22502.3 Torr; for 5h; Inert atmosphere; Stage #2: With water; sodium hydroxide at 220℃; for 2.5h; Concentration; Temperature; Inert atmosphere;

U1TEPA → DU1,3TEPA + DU1,4TEPA + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
at 220 - 280℃; under 2.25023 - 12.7513 Torr; for 10h;

U2TEPA → DU1,3TEPA + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
at 220 - 280℃; under 2.25023 - 12.7513 Torr; for 10h;

ethyl trifluoroacetate, (383-63-1) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → N,N'-(((azanediylbis(ethane-2,1-diyl))bis(azanediyl))bis(ethane-2,1-diyl))bis(2,2,2-trifluoroacetamide) (936720-60-4)

Conditions	Yield
In methanol at -78 - 20℃; for 25h;	100%
In dichloromethane at 0 - 20℃; for 1.5h;
In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;

guanidine hydrochloride (50-01-1) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + tridecanoic acid (638-53-9) → C37H77N11O2*ClH

Conditions	Yield
Stage #1: N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine; tridecanoic acid With toluene-4-sulfonic acid at 155℃; for 2.75h; Stage #2: guanidine hydrochloride at 152 - 176℃; for 5h;	98.5%

N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + Stearoyl chloride (112-76-5) → Octadecanoic acid bis-{2-[octadecanoyl-(2-octadecanoylamino-ethyl)-amino]-ethyl}-amide

Conditions	Yield
With triethylamine In acetone for 3h; Ambient temperature;	98%

2-acetyldimedone (1755-15-3) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → 1,13-bis[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-tetraethylenepentamine (936720-58-0)

Conditions	Yield
With molecular sieve In ethanol at 20℃; for 24h;	98%

N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + 2-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)benzaldehyde (122174-22-5) → NH(CH2CH2NHCH2CH2NCHC6H3(OH)OCH2CH2OCH2CH2OCH3)2 (155990-29-7)

Conditions	Yield
In methanol for 2h; Heating;	96%

N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + 2-Hydroxy-3-{2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-benzaldehyde (155990-24-2) → NH(CH2CH2NHCH2CH2NCHC6H3(OH)OCH2(CH2OCH2)5CH2OH)2 (155990-31-1)

Conditions	Yield
In methanol for 2h; Heating;	96%

nickel(II) chloride hexahydrate + tetrabutylammonium hexachlororhenate(IV) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → [Ni(tetraethylpentamine)][ReCl6] (840454-35-5)

Conditions	Yield
In methanol a soln. of Ni-salt and pentamine in methanol was added dropwise to the hot (50°C) soln. of (N(C4H9)4)2ReCl6 in methanol, the mixt. was slowly heated up to 50°C for about 0.5 h; filtered, washed with methanol and diethyl ether; elem. anal.;	96%

N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + 2-Hydroxy-3-[2-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzaldehyde (155990-23-1) → NH(CH2CH2NHCH2CH2NCHC6H3(OH)OCH2(CH2OCH2)4CH2OCH3)2 (155990-30-0)

Conditions	Yield
In methanol for 2h; Heating;	95%

methanol (67-56-1) + nickel(II) chloride hexahydrate + tetrabutylammonium hexachlororhenate(IV) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → [Ni(tetraethylpentamine)][ReCl6]*CH3OH (840454-36-6)

Conditions	Yield
In methanol a soln. of Ni-salt and pentamine in methanol was added dropwise to the soln. of (N(C4H9)4)2ReCl6 in methanol, the mixt. was stirred at room temp.; filtered, washed with methanol and diethyl ether; elem. anal.;	92%

rhodamine B (81-88-9) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → N-(rhodamine B)lactam-tetraethylenepentamine (1313741-43-3)

Conditions	Yield
In ethanol at 80℃; for 12h; Solvent; Temperature;	90.8%
In ethanol at 80℃; Inert atmosphere;	87%
at 80℃; Inert atmosphere;	87%
In ethanol for 12h; Reflux;	72%

rhodamine B (81-88-9) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → C36H53N7O2

Conditions	Yield
In ethanol for 12h; Reflux;	90.8%

4-amino-2-methoxy-1-methyl-5-nitroso-6-oxo-1,6-dihydropyrimidine (75482-16-5) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → C18H31N13O4

Conditions	Yield
In methanol at 20℃;	90%

N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + acrylonitrile (107-13-1) → 3-(Bis-{2-[{2-[bis-(2-cyano-ethyl)-amino]-ethyl}-(2-cyano-ethyl)-amino]-ethyl}-amino)-propionitrile

Conditions	Yield
In water for 24h; Heating;	89%

salicylaldehyde (90-02-8) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → C29H35N5O3 (1427062-13-2)

Conditions	Yield
In ethanol for 8h; Reflux;	89%
In ethanol

p-acetoxycinnamoyl chloride (53901-95-4, 108608-06-6, 58523-18-5) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → N1,N4,N7,N10,N13-penta(4-o-acetylcoumaroyl)tetraethylenepentamine (364049-01-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	87%

hydrogen iodide (10034-85-2) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + lead(II) iodide → C8H23N5*Pb(2+)*5I(1-)*3H(1+)

Conditions	Yield
In ethanol; water at 150℃; for 96h;	87%

3,5-dichloropyridine (2457-47-8) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → N-(2-aminoethyl)-N'-{2-{{2-[(5-chloropyridin-3-yl)amino]ethyl}amino}ethyl}ethane-1,2-diamine + N,N'-bis-(2-{2-[2-(2-amino-ethylamino)-ethylamino]-ethylamino}-ethyl)-pyridine-3,5-diamine

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane for 5h; Heating;	A 86% B 14%

3,4,5-Trimethoxybenzoyl chloride (4521-61-3) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → C58H73N5O20

Conditions	Yield
With potassium carbonate In water; ethyl acetate	85%

N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) + silver(I) iodide + lead(II) iodide → [(tepa)(PbAg2I4)]n

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide at 90℃; for 72h; Autoclave;	85%

carbon disulfide (75-15-0) + dimethyltin dichloride (753-73-1) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → tetraethylenepentamine bis(dithiocarbamate) dimethyltin(IV) (1228345-48-9)

Conditions	Yield
With KOH In methanol addn. of CS2 to methanolic soln. of amine deriv. at 0°C, addn. ofmethanolic soln. of KOH, stirring for 3 h at 4°C, addn. of metha nolic soln. of tin compd., stirring for 3 h at room temp.; evapn., washing with methanol and diethyl ether, drying in vac. over P2O5, elem. anal.;	81%

phosphoric acid (86119-84-8, 7664-38-2) + water (7732-18-5) + zinc(II) acetate dihydrate (5970-45-6) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → 6Zn(2+)*5PO4(3-)*HPO4(2-)*H2N(CH2CH2NH2CH2CH2NH3)2(5+)*5H2O=[Zn6(PO4)5(HPO4)][H2N(CH2CH2NH2CH2CH2NH3)2]*5H2O

Conditions	Yield
In water High Pressure; Zn(OAc)2*2H2O dispersed into H2O; H3PO4 slowly added; tetraethylenepentamine added dropwise with stirring; heated in autoclave at 393 K for 2 dsunder autogenous pressure; filtered; washed (H2O); dried at room temp.; elem. anal.;	80%

cis-3-(6-bromohexyl)-8-(4-isopropyl-cyclohexyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one trifluoroacetate + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → cis-8-(4-isopropyl-cyclohexyl)-3-(7,10,14,17,20-pentaazaeicosanyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one trifluoroacetate

Conditions	Yield
In ethanol at 20℃; for 24h;	78%

pyridine-2-carbaldehyde (1121-60-4) + copper(II) choride dihydrate + water (7732-18-5) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → [Cu(C5H4NCHNCH2CH2(NHCH2CH2)3NCHC5H4N)](2+)*2Cl(1-)*H2O=[Cu(C5H4NCHNCH2CH2(NHCH2CH2)3NCHC5H4N)]Cl2*H2O

Conditions	Yield
In methanol polyamine (2 mmol) and 2-pyridinecarboxaldehyde (4 mmol) refluxed in MeOH, MeOH soln. of CuCl2*2H2O (2 mmol) added, mixt. refluxed for 1 h; concd., ppt. filtered off, washed (Et2O), dried (vac.), elem. anal.;	78%

ferrocenecarboxaldehyde (12093-10-6) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → 1,15-diferrocenyl-2,5,8,11,14-pentaazapentadecane (217494-67-2)

Conditions	Yield
Stage #1: ferrocenecarboxaldehyde; N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine In methanol at 70℃; for 24h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 12.5h; Inert atmosphere;	77%
With LiAlH4 In tetrahydrofuran; ethanol refluxing the aldehyde and the amine in EtOH for 3 h, evapn. to dryness,dissoln. (THF), addn. of LiAlH4, reflux under argon for 1 h, quenching with H2O; filtration, evapn. to dryness, addn. of basic H2O and CH2Cl2, drying (Na2SO4), chromy. (alumina; CH2Cl2, then CH2Cl2/MeOH); elem. anal.;	70%

carbon monoxide (201230-82-2) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → {COFeC8H23N5}(2+)*2I(1-)={COFeC8H23N5}I2

Conditions	Yield
With sodium hydroxide; hydrogen iodide; iron(II) sulfate In water at room temp. under CO pressure of 3 atm for 6 d; washing with ethanol, then ether, drying in vacuum;	76%
With HI; FeSO4; NaOH In water at room temp. under CO pressure of 3 atm for 6 d; washing with ethanol, then ether, drying in vacuum;	76%
With sodium hydroxide; hydrogen iodide; iron(II) sulfate In water at room temp. under CO pressure of 3 atm for 3 d; washing with ethanol, then ether, drying in vacuum;	57%
With FeSO4; HI; NaOH In water at room temp. under CO pressure of 3 atm for 3 d; washing with ethanol, then ether, drying in vacuum;	57%

selenium (7782-49-2) + tin (IV) chloride pentahydrate + cobalt(II) chloride hexahydrate + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → [Co(tetraethylenepentamine)]2(μ2-Sn2Se6)

Conditions	Yield
In water High Pressure; mixt. of CoCl2*6H2O, SnCl4*5H2O, Se amine and water heated in sealed tube at 157°C for 1 d; washed with EtOH, dried in vac.; elem. anal.;	75%

manganese(II) chloride tetrahydrate + germanium dioxide + sulfur (7704-34-9) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → [Mn(II)(tetraetylenepentamine)]2(μ2-Ge2S6)

Conditions	Yield
In water High Pressure; tetraethylenepentamine/H2O soln. heated at 180 °C for 7 d in container under autogenous pressure; filtration, washing (ethanol, diethyl ether), drying and stored under vac., elem. anal.;	75%

dimethyl 5,5'-(oxybis(methylene))bis(furan-2-carboxylate) (36801-99-7) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2) → 1,4,7-Trioxa-10,13,16,19,22-pentaazadifuro<2,1,5-a,x:2,1,5-f,g>cyclotetraeicosane-9,23-dione (102432-83-7)

Conditions	Yield
In ethanol for 20h; Heating;	73.8%

Upstream product

• 107-06-2 1,2-dichloro-ethane 
• 111-40-0 3-azapentane-1,5-diamine 
• 151-56-4 ethyleneimine 
• 112-24-3 triethylentetramine 
• 23435-23-6 1-<2-<(2-aminoethyl)amino>ethyl>aziridine 
• 107-15-3 ethylenediamine 
• 46467-99-6 {COFeC₈H₂₃N₅}⁽²⁺⁾ 
• 3699-54-5 2-oxo-imidazolidine-1-ethanol 
• 6281-42-1 2-aminoethylimidazolidone 
• 111-42-2 2,2'-iminobis[ethanol] 
• 141-43-5 ethanolamine 
• 1051939-66-2 diethylenetriaminediacetonitrile 

Downstream Products

• 119721-03-8 {2-[2-(2-{2-[Bis-(3-dimethylamino-phenoxy)-thiophosphorylamino]-ethylamino}-ethylamino)-ethylamino]-ethyl}-thiophosphoramidic acid O,O'-bis-(3-dimethylamino-phenyl) ester 
• 109505-22-8 C₈₈H₁₁₈N₁₅O₁₀P₅S₅ 
• 107-15-3 ethylenediamine 
• 138403-41-5 3-(4-nitrobenzyl)-2,6-dioxo-1,4,7,10,13,16-hexaazacyclooctadecane 
• 364049-01-4 N¹,N⁴,N⁷,N¹⁰,N¹³-penta(4-o-acetylcoumaroyl)tetraethylenepentamine 
• 936720-58-0 1,13-bis[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-tetraethylenepentamine 
• 1268832-63-8 2-[2-[tert-butoxycarbonyl-[2-[tert-butoxycarbonyl-[2-[tert-butoxycarbonyl-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]amino]ethyl]amino]ethyl]amino]ethylcarbamoyl]benzoic acid 
• 1326318-82-4 C₁₁₃H₁₆₃N₅O₄₀ 
• 1268839-83-3 C₄₄H₅₈N₁₀ 
• 1427062-13-2 C₂₉H₃₅N₅O₃ 
• 3216-98-6 C₁₄H₂₉N₇ 
• 111682-55-4 N,N''''-bis(salicylaldimino)tetraethylenepentaamine 
• 343315-27-5 tetraethylenepentamine β-cyclodextrin 

Relevant academic research and scientific papers

PROCESS TO CONVERT THE CYCLIC MONOUREA OF AN ETHYLENE AMINE COMPOUND INTO THE ETHYLENE AMINE COMPOUND

The present invention relates to a process to convert the cyclic monourea of ethylene amine compounds (U-EA) into ethylene amine compound (EA) by performing a reactive separation step using a reaction mixture containing the cyclic monourea, wherein one cyclic monourea (U-EA) reacts with another cyclic monourea (U-EA) to transfer its urea unit thereto and the obtained ethylene amine compound (EA) without urea unit is separated from the reaction mixture.

TWO-STEP PROCESS FOR CONVERTING CYCLIC ALKYLENE UREAS INTO THEIR CORRESPONDING ALKYLENE AMINES

The invention pertains to a process for converting cyclic alkyleneureas into their corresponding alkyleneamines, comprising - in a first step converting cyclic alkyleneureas into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO2, so as to convert between 5 mole% and 95 mole% of alkyleneurea moieties in the feedstock to the corresponding amines, and - in a second step adding an inorganic base and reacting cyclic alkylene ureas remaining from the first step with the inorganic base to convert them partially or completely into their corresponding alkyleneamines. It has been found that the two-step process of the present invention makes it possible to still obtain a high conversion of cyclic alkyleneureas, while using substantially less strong inorganic base. The process according to the invention also shows a higher selectivity to amines than the prior art process.

PROCESS FOR MAKING HIGHER ETHYLENE AMINES

The invention pertains to a process to prepare ethylene amines with n ethyleneunits and n+1 amine groups wherein n is at least 4, or urea derivatives of said ethylene amines, by reacting an ethanolamine-functional compound, an amine-functional compound, and a carbon oxide delivering agent, wherein the ethanolamine-functional compound is of the formula HO-(C2H4-NH-)qH, q is at least 1, the amine-functional compound is of the formula H2N-(C2H4-NH-)rH, r is at least 1, the sum q+r is at least 4 and wherein optionally one or more of the ethanol-amine functional compound or amine-functional compound are at least partly used as their cyclic carbamate derivative, or linear or cyclic urea derivative. The process provides TEPA and higher ethylene amines in high yield and high selectivity, without having to use expensive or hazardous startingmaterials. Various urea derivatives of TEPA and PEHA are also claimed.

METHOD FOR PRODUCING POLYETHYLENE POLYAMINES

PROBLEM TO BE SOLVED: To provide a method for producing polyethylene polyamines with high selectivity and high yield. SOLUTION: In the presence of a solid acid catalyst, ethylene amines and aziridine are reacted with each other so that an equivalent of ethylene amines is 3 equivalents or more and 30 equivalents or less relative to aziridine. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

PROCESS FOR MANUFACTURING CHAIN-EXTENDED HYDROXYETHYLETHYLENEAMINES, ETHYLENEAMINES, OR MIXTURES THEREOF

The invention pertains to 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 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, wherein -the molar ratio of amine-functional compound to diethanolamine is at least 0.2:1, and -the molar ratio of carbon oxide delivering agent to –NH-CH2-CH2-NH-units in the amine-functional compound is at least 0.1:1. The invention makes it possible to obtain higher hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof from diethanolamine, which is an attractive starting material.

PREPARATION METHOD OF ETHYLENEAMINE-BASED COMPOUNDS

The present invention relates to a method for preparing ethylene amine-based compounds which allows selective preparation of ethylene amine compounds having a higher molecular weight at a high ratio while improving the overall energy efficiency. The method for preparing ethylene amine-based compounds according to the present invention comprises a first reaction step and a second reaction step in which ethylene dichloride reacts with aqueous ammonia so that the molar ratio of ethylene dichloride (EDC) to ammonia may be 1:4-1:10. In the method, ethylene dichloride is introduced in an amount corresponding to 30-70 mol% of the total feed, and the balance amount is introduced in the second reaction step.COPYRIGHT KIPO 2017

Amination process for manufacturing amines using catalyst

Disclosed is a process for the preparation of an amine (particularly diamines and polyamines) by reacting an alkanolamine or a polyol with ammonia in the presence of a catalyst composed of two active metals from the group of transition metals, namely nickel and chromium supported on a microporous refractory substrate, in a hydrogenated, trickle bed reactor.

METHOD FOR PRODUCING ETHYLENEAMINES

The present invention relates to method for producing ethyleneamines that includes: reacting ethylenedichloride with ammonia water under conditions optimizing the molar ratio of ethylenedichloride to ammonia in a defined range to produce amine compounds, ammonium chloride, and water; and isolating the amine compounds, ammonium chloride, and water, respectively. The present invention provides a continuous process for producing ethyleneamines using ethylenedichloride and ammonia by efficiently controlling the composition of the ethyleneamine product in accordance with the supply and demand of ethyleneamines to optimize the distribution of ethyleneamines.

FUNCTIONALIZED HIGHLY BRANCHED MELAMINE-POLYAMINE POLYMERS

The present invention relates to a method for producing amphiphilic functionalized highly branched melamine-polyamine polymers by condensing melamine and optionally a melamine derivate having at least one different amine having at least two primary amino groups and optionally also with urea and/or at least one urea derivative and/or with at least one at least difunctional diisocyanate or polyisocyanate and/or at least one carbolic acid having at least two carboxyl groups or at least one derivative thereof, optionally quaternizing a portion of the amino groups of the polymer thereby obtained, reacting the polymer thus obtained with at least one compound capable of undergoing a condensation or addition reaction with amino groups, and optionally quaternizing at least part of the amino groups of the polymer obtained in the first step. The invention further relates to the amphiphilic functionalized highly branched melamine-polyamine polymers that can be obtained by the method according to the invention, and to the use thereof as surface active agents.

METHOD FOR PRODUCING TETRAETHYLENEPENTAMINE

The invention relates to a process for preparing tetraethylenepentamine (TEPA) by hydrogenation of diethylenetriaminediacetonitrile (DETDN) over a catalyst. If appropriate, DETDN can also be present as a constituent of an amino nitrile mixture which additionally comprises diethylenetriaminemonoacetonitrile (DETMN).