111-40-0

Usage

Uses

Used in Chemical Synthesis:
Diethylenetriamine is used as a solvent for sulfur, acidic gas, resin, and dye intermediates in organic synthesis. It is also used as a saponification agent for acidic materials and as a fuel component.
Used in Industrial Applications:
Diethylenetriamine is used as a hardener and stabilizer for epoxy resins, particularly in the production of reactive polyamide resins, aminoamides, and imidazolines from fatty acids. It is also used in the production of paper wet strength resins and piperazine.
Used in Solvent Applications:
Diethylenetriamine serves as a solvent for various applications, including plastics and dyes, and is used in chemical synthesis.
Used in Fuel Components:
It is used as a component in the fuel industry, contributing to the overall performance and efficiency of the fuel.
Used in the Production of Epoxy Resins:
Diethylenetriamine is used as a hardener in epoxy resins of the Bisphenol A type, enhancing their properties and making them suitable for various applications.
Used in Ultrasonic Baths for Cleaning Jewels:
It has been reported as a sensitizer in ultrasonic baths for cleaning jewels, improving the cleaning process and efficiency.
Used in Synthetic Lubricants:
Diethylenetriamine is used in the formulation of synthetic lubricants, enhancing their performance and durability.
Used in Carbonless Copy Paper:
It is also used in the production of carbonless copy paper, contributing to the paper's unique properties and functionality.

Production Methods

Diethylenetriamine is produced by the reaction of ethylene dichloride with ammonia. Diethylenetriamine is used in biological studies, for polyamines inhibition to carbonic anhydrases by anchoring to the zinc-coordinated water molecule.

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 5002, 1983 DOI: 10.1021/ja00353a025

Air & Water Reactions

Soluble in water.

Reactivity Profile

Diethylenetriamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

Prolonged breathing of vapors may cause asthma. Liquid burns skin and eyes. A skin rash can form.

Health Hazard

Brief contact with concentrated diethylenetriamine can produce severe local injury to the eyes and skin resembling the effect from strong base. Human subjects are susceptible to sensitization responses either as dermatitis or an asthma-like response. A time-weighted average of 1 p.p.m. is recommenced for diethylenetriamine (ACGIH 1986).

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors are generated when heated.

Flammability and Explosibility

Nonflammable

Contact allergens

Diethylenetriamine is a hardener in epoxy resins of the Bisphenol A type. It has been reported to be a sensitizer when used in an ultrasonic bath for cleaning jewels, in synthetic lubricants, or in carbonless copy paper.

Safety Profile

Poison by skin contact and intraperitoneal routes. Moderately toxic by ingestion. Corrosive. A severe skin and eye irritant. High concentration of vapors causes irritation of respiratory tract, nausea, and vomiting. Repeated exposures can cause asthma and sensitization of skin. Combus uble when exposed to heat or flame; can react with oxidizing materials. Mxture with nitromethane is a shock-sensitive explosive. Ignites on contact with cellulose nitrate of high surface area. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Carcinogenicity

DETA has a strong ammonia-like odor, but it does not provide adequate warning of hazardous concentrations. The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for diethylene triamine is 1ppm (4.2mg/m3) with a notation for skin absorption.

Metabolism

Diethylenetriamine is readily absorbed through the gastrointestinal tract and 96% of the administered dose is excreted within 48 h (USEPA 1983a). Roughly equal amounts are excreted in the feces and urine with at least 4 metabolites being detected (but not identified) in the latter. Only a small proportion (<2%) was recovered as expired carbon dioxide. Any residual remaining in the animal was found primarily in kidney, liver, bladder and large intestine.

Purification Methods

Dry the amine with Na and distil, preferably under reduced pressure, or in a stream of N2. [Beilstein 4 IV 1284.]

InChI:InChI=1/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2/p+3

Synthetic route

iminodiacetonitrile (628-87-5) → piperazine (110-85-0) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With ammonia; hydrogen; potassium hydroxide In ethanol at 80℃; under 90009 Torr; Pressure; Reagent/catalyst; Solvent; Temperature; Time;	A 1.03% B 97.53%

ethyleneimine (151-56-4) + ethylenediamine (107-15-3) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With iron(II) sulfate at 150℃; for 2h; Autoclave;	93%
palladium at 120℃; for 12h;	81%
With hydrogenchloride In water at 35℃; Kinetics; Thermodynamic data; ring opening reactions, at various temperature, Ea is given;

[C5H4NCH2Cr(NH((CH2)2NH2)2)]Cl2 (99708-65-3) → 1,2-di-(3-pyridyl)-ethane (4916-58-9) + 3-Methylpyridine (108-99-6) + chromium(III) hexahydrate cation (14873-01-9) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
In perchloric acid Kinetics; (N2); decompn. of Cr complex in 1 M HClO4 depending on temp. under anaerobic conditions; not isolated, monitored by UV;	A 30% B 55% C n/a D n/a
In perchloric acid Kinetics; decompn. of Cr complex in 1 M HClO4 depending on temp. under aerobic conditions; not isolated, monitored by UV;	A 38% B 48% C n/a D n/a

ethylene glycol (107-21-1) → piperazine (110-85-0) + ethanolamine (141-43-5) + 2-(2-Aminoethylamino)ethanol (111-41-1) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
Stage #1: ethylene glycol With ammonia; hydrogen at 150℃; under 150015 Torr; Stage #2: copper oxide; graphite; molybdenum oxide; nickel oxide; zirconium dioxide; mixture of at 170℃; under 150015 Torr;	A 6.8% B 29% C 5.7% D 49.5% E 3.9% F 1.7%
With ammonia; hydrogen at 170 - 180℃; under 150015 Torr; Conversion of starting material;
With ammonia; water; hydrogen at 180℃; under 150015 Torr; Conversion of starting material;
With ammonia; hydrogen at 150 - 170℃; under 150015 Torr; Conversion of starting material;
With ammonia; hydrogen at 200℃; under 150015 Torr; Conversion of starting material;

bis(phthalimidylethyl)amine (63563-83-7) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With hydrogenchloride; water

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + ethylenediamine (107-15-3) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With sodium hydroxide; water at 104℃;
With sodium hydroxide; water at 104℃;

1,2-dichloro-ethane (107-06-2) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With ammonia
With ammonia; water at 115 - 120℃;

1-(2-amino-ethyl)-aziridine (4025-37-0) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With hydrogenchloride; ammonia; ammonium chloride In water at 50℃; Rate constant; Thermodynamic data; effect of the ammonia an d hydrochloric acid concn. and the temperature;
With hydrogenchloride; ammonia In water at 60℃; Thermodynamic data; ΔH(scission), activation energy;

ethyleneimine (151-56-4) + ammonium chloride + ammonia (7664-41-7) → piperazine (110-85-0) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
at 100℃; under 36775.4 Torr;
at 25℃; under 7355.08 Torr;

1,7-di-p-toluenesulfonyl-triethylenediamine → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With hydrogenchloride at 160℃;

ammonia (7664-41-7) + 1,2-dichloro-ethane (107-06-2) → ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
unter Druck;

ammonia (7664-41-7) + ethylene dibromide (106-93-4) → ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3) + diethylene-diamine

ammonia (7664-41-7) + 1,2-dichloro-ethane (107-06-2) → ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylanetetraamine

Conditions	Yield
unter Druck;

ethylene dibromide (106-93-4) → 1,5-diamino-3-azapentane (111-40-0) + triethylenetriamine

Conditions	Yield
With ammonia

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + ammonia (7664-41-7) + aqueous NaOH → 2-(2-Aminoethylamino)ethanol (111-41-1) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
at 130℃; mit Dimethylamin und anderen Alkylaminen an Stelle von NH3 verlaeuft die Reaktion analog;

(Z)-1-[N-(2-aminoethyl)-N-(2-ammonioethyl)-amino]-diazen-1-ium-1,2-diolate → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With sodium hydroxide; phosphate buffer at 37℃; pH=5.88 - 7.46; Kinetics; Further Variations:; pH-values; Reagents;

N,N-bis(2-(1,3-dioxoisoindolin-2-yl)ethyl)-4-methylbenzenesulfonamide (23538-91-2) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With hydrogen bromide; acetic acid for 72h; Heating;

ethanolamine (141-43-5) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With ammonia; ethylenediamine; monoaluminum phosphate In tungstosilicic acid

ethylenediamine (107-15-3) → piperazine (110-85-0) + 1-(2-hydroxyethyl)piperazine (103-76-4) + aminoethylpiperazine (140-31-8) + 2-(2-Aminoethylamino)ethanol (111-41-1) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With hydrogen at 150 - 160℃; under 22502.3 Torr;

ethylenediamine (107-15-3) → piperazine (110-85-0) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
hetrogeneous catalyst at 162 - 186℃; Conversion of starting material;
With hydrogen; heterogeneous Ni-Re on a 1/16" alumina silica (80:20) support at 152.1℃; under 42148.7 Torr; Product distribution / selectivity;
6.8 weight% Ni and 1.8 weight% Re on mixture of θ -alumina and silica (80:20), activated on heating in H2 at 140℃; Product distribution / selectivity; Gas phase;

ethanolamine (141-43-5) → piperazine (110-85-0) + 1-(2-hydroxyethyl)piperazine (103-76-4) + aminoethylpiperazine (140-31-8) + 2-(2-Aminoethylamino)ethanol (111-41-1) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With ammonia; hydrogen at 170℃; under 150015 Torr;

ethylenediamine (107-15-3) → 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With hydrogen; DE-A19 53 263 catalyst at 150 - 170℃; under 12751.3 - 150015 Torr; Conversion of starting material;
With hydrogen; nickel on silica/alumina (Sud-Chemie C46-7-03) at 156℃; under 42133 - 59457.9 Torr; for 1h; Product distribution / selectivity; Autoclave;
With hydrogen; heterogeneous Ni-Re on a 1/16" alumina silica (80:20) support at 150.3℃; under 42148.7 Torr; Product distribution / selectivity;

oxirane (75-21-8) → piperazine (110-85-0) + ethanolamine (141-43-5) + 2-(2-Aminoethylamino)ethanol (111-41-1) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
Stage #1: oxirane With ammonia at 95℃; under 105011 Torr; Stage #2: With hydrogen; DE-A19 53 263 catalyst In water at 170 - 210℃; under 150015 Torr;

triethylentetramine (112-24-3) → 1,5-diamino-3-azapentane (111-40-0)

[C5H4NCH2Cr(NH((CH2)2NH2)2)]Cl2 (99708-64-2) → α-picoline (109-06-8) + chromium(III) hexahydrate cation (14873-01-9) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
In perchloric acid Kinetics; (N2); decompn. of Cr complex in 1 M HClO4 depending on temp. under anaerobic conditions; not isolated, monitored by UV;
In perchloric acid Kinetics; decompn. of Cr complex in 1 M HClO4 depending on temp. under aerobic conditions; not isolated, monitored by UV;

ethanolamine (141-43-5) → ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With ammonia; 10wt% CoO/10wt%NiO/4wt%CuO on γ-Al2O3 activated with hydrogen at 174.8 - 175℃; under 150015 - 165017 Torr; Product distribution / selectivity;
With ammonia; Ni-Re Product distribution / selectivity;

ethylenediamine (107-15-3) → piperazine (110-85-0) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With hydrogen; 10% by weight of CoO, 10% by weight of NiO and 4% by weight of CuO on γ-Al2O3 at 150 - 175℃; under 21752.2 - 67506.8 Torr; Product distribution / selectivity;
With hydrogen; 57percent nickel on silica (Engelhard Ni5256E) at 173℃; under 50407.6 - 111433 Torr; for 3h; Product distribution / selectivity; Autoclave;
With hydrogen; heterogeneous Ni-Re on a 1/16" alumina silica (80:20) support at 155.5℃; under 52491.9 Torr; Product distribution / selectivity;
With hydrogen; 6.8 wtpercent Co on theta alumina/silica (80:20) at 124 - 146℃; under 31789.8 Torr; for 487h; Product distribution / selectivity; Neat (no solvent);

ethylenediaminemonoacetonitrile + 2,2’-(ethane-1,2-diylbis(azanediyl))diacetonitrile (18907-76-1) → piperazine (110-85-0) + aminoethylpiperazine (140-31-8) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

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

2-aminoacetonitrile (540-61-4) + iminodiacetonitrile (628-87-5) → ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With hydrogen; Cr-doped Raney cobalt In tetrahydrofuran Product distribution / selectivity; In autoclave;
With hydrogen; Cr-doped Raney cobalt In tetrahydrofuran; water Product distribution / selectivity; In autoclave;
With hydrogen In tetrahydrofuran; water for 7h; Product distribution / selectivity; Autoclave;

trityl chloride (76-83-5) + 1,5-diamino-3-azapentane (111-40-0) → N-(2-(triphenylmethyl)amino)ethyl-1,2-ethanediamine

Conditions	Yield
In dichloromethane at 0 - 20℃; for 5h;	100%
In dichloromethane at 0℃;	94%

5,11,17,23-tetra-tert-butyl-25,27-di(ethoxycarbonylmethoxy)-26,28-dihydroxycalix[4]arene (1262336-92-4) + 1,5-diamino-3-azapentane (111-40-0) → (C6H2(C(CH3)3)OCH2)4H2(CH2C(O)NHCH2CH2)2NH (136158-03-7)

Conditions	Yield
In methanol; toluene at 80℃;	100%
In methanol; toluene for 24h; Heating;	72%
In methanol; toluene Ambient temperature;	63%
In ethanol Heating;	60%
In methanol; toluene for 48h;

pyridine-2-carbaldehyde (1121-60-4) + 1,5-diamino-3-azapentane (111-40-0) → N-pyridin-2-ylmethyl-N'-{2-[(pyridin-2-ylmethyl)amino]ethyl}ethane-1,2-diamine (58214-73-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 2585.74 Torr; for 24h;	100%
Stage #1: pyridine-2-carbaldehyde; 3-azapentane-1,5-diamine In ethanol at 50℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In ethanol at 50℃; for 2h; Inert atmosphere; chemoselective reaction;	92%
Stage #1: pyridine-2-carbaldehyde; 3-azapentane-1,5-diamine With acetic acid; zinc In methanol at 70 - 80℃; for 4.5h; Stage #2: With hydrogenchloride In methanol at 20℃; Stage #3: With sodium hydroxide In water	85%

furan-3-carboxaldehyde (498-60-2) + 1,5-diamino-3-azapentane (111-40-0) → N-furan-3-ylmethyl-N'-{2-[(furan-3-ylmethyl)-amino]-ethyl}-ethane-1,2-diamine

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 2585.74 Torr; for 24h;	100%

2,4,6-trimethylphenyl bromide (576-83-0) + 1,5-diamino-3-azapentane (111-40-0) → (2,4,6-Me3C6H2NHCH2CH2)2NH (236111-35-6)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene Heating;	100%

ethyl trifluoroacetate, (383-63-1) + 1,5-diamino-3-azapentane (111-40-0) → 2,2,2-trifluoro-N-[2-({2-[(trifluoroacetyl)amino]ethyl}amino)ethyl]acetamide (88793-42-4)

Conditions	Yield
In acetonitrile at 20℃;	100%
In water; acetonitrile for 18h; Reflux;	99%
In tetrahydrofuran Acylation; Heating;	95%

1,5-diamino-3-azapentane (111-40-0) + 1-chloro-6-methylxanthone (359028-02-7) → 1-[(2-aminoethyl)aminoethylamino]-6-methylxanthone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;	100%

2,6-bis(methoxycarbonyl)pyridine (5453-67-8) + 1,5-diamino-3-azapentane (111-40-0) → C5H3N(CONHCH2CH2NHCH2CH2NH2)2 (955084-14-7)

Conditions	Yield
In methanol for 1h; Heating;	100%

1,5-diamino-3-azapentane (111-40-0) + 2,2-dimethyltetrahydro-[1,3]dithiol[4,5-c]furan (55550-98-6) → C18H29N3O6S4 (869193-24-8)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 1h;	100%

formaldehyd (50-00-0) + 1,5-diamino-3-azapentane (111-40-0) → 1-(2-aminoethyl)imidazolidine (49859-90-7)

Conditions	Yield
In water at 60℃; for 0.5h; Temperature; Solvent; Inert atmosphere;	100%
In water at 0℃; for 1.16667h;	95%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 1,5-diamino-3-azapentane (111-40-0) → N,N'-bis-(3,5-di-tert-butylsalicylidene)diethylenetriamine

Conditions	Yield
In toluene at 20℃; for 4h;	100%

1,5-diamino-3-azapentane (111-40-0) + carbonic acid dimethyl ester (616-38-6) → C8H17N3O4 (1312807-92-3)

Conditions	Yield
at 20℃; under 6000600 Torr; for 16h; neat (no solvent);	100%

1,5-diamino-3-azapentane (111-40-0) + 3-phenyl-propenal (104-55-2) → C22H25N3

Conditions	Yield
In ethanol for 1h;	100%

copper(II) carbonate hydroxide + water (7732-18-5) + 1,5-diamino-3-azapentane (111-40-0) → di(μ-carbonato)bis[aqua(diethylenetriamine)copper(II)] hexahydrate

Conditions	Yield
at 20℃;	100%

1,5-diamino-3-azapentane (111-40-0) + 2-(1-hydroxy-3-methylbutylidene)-5,5-dimethylcyclohexane-1,3-dione (172611-72-2) → 2,2'-(((azanediylbis(ethane-2,1-diyl))bis(azanediyl))bis(3-methylbutan-1-yl-1-ylidene))bis(5,5-dimethylcyclohexane-1,3-dione)

Conditions	Yield
In dichloromethane Solvent;	100%

terephthalic acid (100-21-0) + 1,5-diamino-3-azapentane (111-40-0) → C16H24N6

Conditions	Yield
at 170 - 270℃;	100%

4'-(2-chloroacetamido)-4'-deoxy-2'',3',3''',4''',5'',6-hexa-O-benzyl-1,2',2''',3,6',6'''-hexaazidoneomycin + 1,5-diamino-3-azapentane (111-40-0) → 4'-[2-(2-(2-aminoethylamino)ethylamino)acetamido]-4'-deoxy-2'',3',3''',4''',5'',6-hexa-O-benzyl-1,2',2''',3,6',6'''-hexaazidoneomycin

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	100%

4-chloropent-2-ene (1458-99-7) + 1,5-diamino-3-azapentane (111-40-0) → C14H29N3*2ClH

Conditions	Yield
In water at 80℃; under 760.051 Torr; for 0.75h; Inert atmosphere;	99.96%

4-chloropent-2-ene (1458-99-7) + 1,5-diamino-3-azapentane (111-40-0) → C9H21N3*ClH (1191290-73-9)

Conditions	Yield
In water at 80℃; under 760.051 Torr; for 0.75h; Inert atmosphere;	99.94%

4-chloropent-2-ene (1458-99-7) + 1,5-diamino-3-azapentane (111-40-0) → C19H37N3*3ClH

Conditions	Yield
In water at 80℃; under 760.051 Torr; for 0.75h; Inert atmosphere;	99.8%

1,5-diamino-3-azapentane (111-40-0) + chloroacetic acid (79-11-8) → diethylene triaminepentaacetic acid

Conditions	Yield
Stage #1: 3-azapentane-1,5-diamine; chloroacetic acid With sodium hydroxide In water at 35 - 60℃; for 8h; pH=11.2 - 11.5; Stage #2: With sodium carbonate In water at 40 - 80℃; for 2h; Reagent/catalyst;	99.7%

2,3,4,5,6-pentamethylbromobenzene (5153-40-2) + 1,5-diamino-3-azapentane (111-40-0) → N1-(2,3,4,5,6-pentamethylphenyl)-N2-(2-(2,3,4,5,6-pentamethylphenylamino)ethyl)ethane-1,2-diamine (862464-60-6)

Conditions	Yield
With sodium t-butanolate; (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate In 1,2-dimethoxyethane at 100℃; for 14h; Product distribution / selectivity;	99.4%

salicylaldehyde (90-02-8) + 1,5-diamino-3-azapentane (111-40-0) → N,N'-bis(salicylidene)diethylenetriamine (2851-60-7)

Conditions	Yield
In neat (no solvent) at 20℃; Green chemistry;	99%
In ethanol at 20℃; for 24h;	92.5%
In water at 20℃; for 1h;	92%

2,6-Bis(2-formylphenoxymethyl)pyridine (66433-95-2) + 1,5-diamino-3-azapentane (111-40-0) → C25H26N4O2

Conditions	Yield
In toluene	99%

1,5-diamino-3-azapentane (111-40-0) + p-toluenesulfonyl chloride (98-59-9) → 1,4,7-tritosyl-1,4,7-triazaheptane (56187-04-3)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0℃; for 1h;	99%
With triethylamine In dichloromethane at 0℃; for 24h;	95%
With potassium carbonate In water; acetone at 0 - 20℃; for 5h;	92%

1,5-diamino-3-azapentane (111-40-0) + D-Glucono-1,5-lactone (90-80-2) → (2S,3R,4S,5R)-2,3,4,5,6-Pentahydroxy-hexanoic acid {2-[2-((2S,3R,4S,5R)-2,3,4,5,6-pentahydroxy-hexanoylamino)-ethylamino]-ethyl}-amide

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; amidation;	99%

1,5-diamino-3-azapentane (111-40-0) + 1H-benzotriazole-1-carboxamidine hydrochloride → N,N-di(2-guanidinylethyl)amine (90010-56-3)

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 6h;	99%

1,5-diamino-3-azapentane (111-40-0) + N,N-dimethyl-1H-benzotriazole-carboximidamide hydrochloride → N'-{2-[2-(N',N'-dimethyl-guanidino)-ethylamino]-ethyl}-N,N-dimethyl-guanidine

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 6h;	99%

bis(1,1,1-trifluoroacetylacetonato)copper(II) + 1,5-diamino-3-azapentane (111-40-0) → copper bis(1,1,1-trifluoro-2,4-pentanedionate) diethylenetriamine

Conditions	Yield
In chloroform anhydrous dien added to soln. of complex;; pptd. from hexane; vacuum-dried; elem. anal.;;	99%

nickel(II) chloride hexahydrate + hexafluoroacetone hydrate (677-71-4) + 1,5-diamino-3-azapentane (111-40-0) → [Ni(di(2-aminoethyl)amine)2][HOC(CF3)2O]2

Conditions	Yield
With KOH In ethanol byproducts: KCl; HOC(CF3)2OH and KOH ethanol soln. addn. to NiCl2 ethanol soln., stirring(30 min); solvent and KCl removing, recrystn. (methanol/ethanol/2-propanol); elem.anal.;	99%

Upstream product

• 151-56-4 ethyleneimine 
• 107-15-3 ethylenediamine 
• 926-39-6 sulfuric acid mono-(2-amino-ethyl ester) 
• 107-06-2 1,2-dichloro-ethane 
• 4025-37-0 1-(2-amino-ethyl)-aziridine 
• 7664-41-7 ammonia 
• 106-93-4 ethylene dibromide 
• 141-43-5 ethanolamine 
• 75-21-8 oxirane 
• 112-24-3 triethylentetramine 
• 99708-65-3 [C₅H₄NCH₂Cr(NH((CH₂)2NH₂)2)]Cl₂ 
• 99708-64-2 [C₅H₄NCH₂Cr(NH((CH₂)2NH₂)2)]Cl₂ 
• 18907-76-1 2,2’-(ethane-1,2-diylbis(azanediyl))diacetonitrile 
• 540-61-4 2-aminoacetonitrile 

Downstream Products

• 1965-29-3 2-[2-(2-aminoethylamino)ethylamino]ethanol 
• 110-85-0 piperazine 
• 85204-23-5 1,1'-(3-aza-pentanediyl)-bis-pyrrolidin-2-one 
• 24656-17-5 2-[2-(2-amino-ethylamino)-ethylamino]-1-phenyl-ethanol 
• 73998-54-6 2-(2-benzyl-4,5-dihydro-imidazol-1-yl)-ethylamine 
• 39549-34-3 1-Benzyldiethylenetriamine 
• 45244-49-3 1-lauroyl diethylenetriamine 
• 3030-47-5 N,N,N',N'',N'''-pentamethyldiethylenetriamine 
• 27825-74-7 N,N-bis-[2-(bis-cyanomethyl-amino)-ethyl]-glycine nitrile 
• 67-43-6 diethylenetriaminopentaacetic acid 
• 16445-01-5 N,N'-(3-aza-pentanediyl)-bis-oleamide 
• 20513-79-5 1-(2-aminoethyl)-2-heptyl-4,5-dihydroimidazole 
• 6313-92-4 3-Nitro-1-<2-(2-nitramino-Δ²-imidazolinyl-(1))-ethyl>-guanidin 
• 100801-42-1 N-[1-(2-amino-ethyl)-4,5-dihydro-1H-imidazol-2-ylmethyl]-p-toluidine 

Related news

Research paperEncapsulation of nano zerovalent iron with ethylenediamine and Diethylenetriamine (cas 111-40-0) for removing cobalt and zinc and their radionuclides from water08/29/2019

This paper demonstrates a new protection technique of nano zerovalent iron (NZVI) by using ethylenediamine (ED) and diethylenetriamine (DETA) as a protective shell in order to prevent the oxidation process. Newly prepared nano sorbent was characterized and applied as efficient adsorbents for zin...detailed

Multi-channel-contained few-layered MoSe2 nanosheet/N-doped carbon hybrid nanofibers prepared using Diethylenetriamine (cas 111-40-0) as anodes for high-performance sodium-ion batteries08/28/2019

A facile new strategy for the synthesis of multi-channel-contained N-doped carbon nanofibers composed of few-layered MoSe2 nanosheets (denoted as MC-NCNF/MoSe2) was introduced and the composite was demonstrated as an anode material for sodium-ion batteries. This was the first time that diethylen...detailed

Liquid–vapor equilibria of pure and aqueous solutions of Diethylenetriamine (cas 111-40-0) or dipropylenetriamine08/26/2019

Vapor pressures of pure and aqueous diethylenetriamine (DETA) and dipropylenetriamine (DPTA) were measured by means of a static apparatus at temperatures between (283 and 363) K. The data were correlated with the Antoine equation and fitted to Redlich–Kister equation using Barker's method....detailed

Application of Diethylenetriamine (cas 111-40-0) grafted on glyoxal cross-linked chitosan composite for the effective removal of metal ions in batch system08/25/2019

This investigation studied the removal of Cu2+, Pb2+, Cd2+, Zn2+, Ni2+ and Cr6+ ions from synthesised wastewater using modified chitosan macromolecules. On this note, chitosan beads (CS) were prepared and cross-linked with glyoxal solution. It was found that cross-linking increased the beads mec...detailed

Effect of Diethylenetriamine (cas 111-40-0) as additive to stabilize the lithium metal anode08/21/2019

Li metal has been regarded as the most promising anode material for next high-energy batteries. However, the dendrite growth during the lithium deposition and low Coulombic efficiencies have restricted their practical applications. In the paper, we investigate the electrodeposition process of li...detailed

Sequestration of U(VI) from aqueous phase using Diethylenetriamine (cas 111-40-0) anchored polystyrene-divinylbenzene copolymer08/20/2019

Diethylenetriamine (DETA) moiety was chemically anchored on polystyrene-divinylbenzene (PS-DVB) co-polymer, and the resultant resin (PS-DETA) was studied for the extraction of uranium from aqueous solution. The extraction behavior of U(VI) was studied in PS-DETA a function of duration of equilib...detailed

Relevant academic research and scientific papers

Gas-phase studies on the reactivity of the azido(diethylenetriamine)platinum(II) cation and derived species

The recent report of the gas-phase loss of nitrogen from [Pt(dien)N3]+ (dien = diethylenetriamine = N-(2-aminoethyl)ethane-1,2-diamine) under collision-induced dissociation (CID) conditions has prompted us to investigate the intriguing structure(s) of [Pt(dien)N]+. This was carried out via CID and ion-molecule reactions (IMR) of [Pt(dien)N]+ in the gas phase. Labelling studies (15N and 2H labelling of the dien ligand) were also employed. As a result, some of the previously proposed structures were ruled out and three other potential structures of [Pt(dien)N]+ are considered. Labelling studies also indicate that the hydrogen atoms of both the amino groups and the carbon backbone of the dien ligand are involved in loss of NH3 from [Pt(dien)N]+. The gas-phase chemistry of [Pt(dien)N-NH3]+, the fragmentation product of [Pt(dien)N]+, was also probed using IMR and CID. The crystal structure of the [Pt(dien)N3]+ cation has also been determined.

METHOD FOR THE PRODUCTION OF ETHYLENEAMINES

The present invention relates to a process for preparing alkanolamines and/or ethyleneamines in the liquid phase, by reacting ethylene glycol and/or monoethanolamine with ammonia in the presence of an amination catalyst comprising Co, Ru and Sn.

PROCESS FOR PREPARING CYCLIC ALKYLENE UREAS

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; in which; R1 is –[A?X?]qR3; R2 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from ?OH and ?NH2; R3 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from ?OH and ?NH2; A is on each occurrence independently selected from C1 to C3 alkylene units, optionally substituted by one or more C1 to C3 alkyl groups; X is on each occurrence independently selected from ?O?, ?NR2?, groups of Formula VI, and groups of Formula VII and p and q are each independently selected from a whole number in the range of from 0 to 8; 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.

PROCESS FOR CONVERTING CYCLIC ALKYLENE UREAS INTO THEIR CORRESPONDING ALKYLENE AMINES

The invention relates to a process for converting one or more cyclic ethylene ureas into corresponding ethylene amines and carbon dioxide. In the process, water is contacted with one or more cyclic alkylene urea compounds comprising one or more cyclic alkylene urea moieties in a reaction vessel at a temperature of 150 to 400°C, optionally in the presence of an amine compound selected from the group of primary amines, cyclic secondary amines and bicyclic tertiary amines. The mole ratio of water to cyclic alkylene urea moieties is in the range of from 0.1 to 20. In the reaction, at least a portion of the cyclic alkylene urea moieties are converted to corresponding alkylenediamine moieties and carbon dioxide, and the carbon dioxide is removed from the liquid reaction mixture in a stripping vessel by feeding a stripping fluid to the stripping vessel, and removing a carbon dioxide-containing stripping fluid.

PROCESS FOR CONVERTING CYCLIC ALKYLENEUREAS INTO THEIR CORRESPONDING ALKYLENEAMINES

The present invention is directed to a process for converting cyclic alkyleneureas into their corresponding alkyleneamines wherein a feedstock comprising cyclic alkyleneureas is reacted in the liquid phase with water in an amount of 0. -20 mole water per mole urea moiety, at a temperature of at least 230°C, with removal of CO2. It has been found that the process according to the invention allows the efficient conversion of alkyleneureas into the corresponding alkyleneamines. The process has a high yield and low side product production. It is preferred for the cyclic alkyleneurea to comprises one or more of EU (ethyleneurea, the urea derivative of ethylenediamine (EDA)), UDETA (the urea derivative of diethylenetriamine (DETA)), UTETA (the group of urea derivatives of triethylenetetraamine (TETA), DUTETA (the diurea derivative of triethylenetetramine), UTEPAs (the urea derivatives of tetraethylenpentamine (TEPA)), DUTEPAs (the diurea derivatives of TEPA), or urea derivatives of pentaethylenehexamine (PEHA) and higher analogues, UAEEA (the urea derivative of aminoethylethanolannine), HE-UDETA (the urea derivative of hydroxyethyl diethylenetriamine), HE-UTETA (the urea derivative of hydroxyethyl triethylenetetraamine, HE-DUTETA (the diurea derivative of hydroxyethyl triethylenetetraamine), or any mixture of these.

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.

Effects of Ni particle size on amination of monoethanolamine over Ni-Re/SiO2 catalysts

Ni-Re/SiO2 catalysts with controllable Ni particle sizes (4.5–18.0 nm) were synthesized to investigate the effects of the particle size on the amination of monoethanolamine (MEA). The catalysts were characterized by various techniques and evaluated for the amination reaction in a trickle bed reactor at 170°C, 8.0 MPa, and 0.5 h?1 liquid hourly space velocity of MEA (LHSVMEA) in NH3/H2 atmosphere. The Ni-Re/SiO2 catalyst with the lowest Ni particle size (4.5 nm) exhibited the highest yield (66.4%) of the desired amines (ethylenediamine (EDA) and piperazine (PIP)). The results of the analysis show that the turnover frequency of MEA increased slightly (from 193 to 253 h?1) as the Ni particle sizes of the Ni-Re/SiO2 catalysts increased from 4.5 to 18.0 nm. Moreover, the product distribution could be adjusted by varying the Ni particle size. The ratio of primary to secondary amines increased from 1.0 to 2.0 upon increasing the Ni particle size from 4.5 to 18.0 nm. Further analyses reveal that the Ni particle size influenced the electronic properties of surface Ni, which in turn affected the adsorption of MEA and the reaction pathway of MEA amination. Compared to those of small Ni particles, large particles possessed a higher proportion of high-coordinated terrace Ni sites and a higher surface electron density, which favored the amination of MEA and NH3 to form EDA.

Effect of Re promoter on the structure and catalytic performance of Ni-Re/Al2O3 catalysts for the reductive amination of monoethanolamine

In this paper, Ni/Al2O3 catalysts (15 wt% Ni) with different Re loadings were prepared to investigate the effect of Re on the structure and catalytic performance of Ni-Re/Al2O3 catalysts for the reductive amination of monoethanolamine. Reaction results reveal that the conversion and ethylenediamine selectivity increase significantly with increasing Re loading up to 2 wt%. Ni-Re/Al2O3 catalysts show excellent stability during the reductive amination reaction. The characterization of XRD, DR UV-Vis spectroscopy, H2-TPR, and acidity-basicity measurements indicates that addition of Re improves the Ni dispersion, proportion of octahedral Ni2+ species, reducibility, and acid strength for Ni-Re/Al2O3 catalysts. The Ni15 and Ni15-Re2 catalysts were chosen for in-depth study. The results from SEM-BSE, TEM, and CO-TPD indicate that smaller Ni0 particle size and higher Ni0 surface area are obtained in the reduced Ni-Re/Al2O3 catalysts. Results from in situ XPS and STEM-EDX line scan suggest that Re species show a mixture of various valances and have a tendency to aggregate on the surface of Ni0 particles. During reaction, the Ni0 particles on the Al2O3 support are stabilized and the sintering process is effectively suppressed by the incorporation of Re. It could be concluded that sufficient Ni0 sites, the collaborative effect of Ni-Re, and brilliant stability contribute to the excellent catalytic performance of Ni-Re/Al2O3 catalysts for the reductive amination of monoethanolamine.

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

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