871-78-3

Basic information

• Product Name: N,N'-DIACETYLETHYLENEDIAMINE
• Synonyms: N,N'-ETHYLENEBISACETAMIDE;N,N'-DIACETYLETHYLENEDIAMINE;N1-[2-(ACETYLAMINO)ETHYL]ACETAMIDE;TIMTEC-BB SBB007829;1,2-ETHYLENEBISACETAMIDE;ETHYLENE BISACETAMIDE;N,N'-ethylenedi(diacetamide);N,N'-Diacetylethylenediamine,98%
• CAS NO: 871-78-3
• Molecular Formula: C₆H₁₂N₂O₂
• Molecular Weight: 144.17
• EINECS: 212-811-9
• Mol File: 871-78-3.mol
• Article Data: 35

Chemical Properties

• Melting Point: 170-172°C
• Boiling Point: 438.7 °C at 760 mmHg
• Flash Point: 214.8 °C
• Appearance: /
• Density: 1.033 g/cm³
• PKA: 15.67±0.46(Predicted)
• Water Solubility: almost transparency
• BRN: 1762229
• CAS DataBase Reference: N,N'-DIACETYLETHYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIACETYLETHYLENEDIAMINE(871-78-3)
• EPA Substance Registry System: N,N'-DIACETYLETHYLENEDIAMINE(871-78-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 871-78-3(Hazardous Substances Data)

Usage

Description

N,N'-DIACETYLETHYLENEDIAMINE, also known as diacetyl ethylenediamine, is a synthetic compound with the chemical formula C6H10N2O2. It is derived from ethylenediamine and acetic anhydride and is characterized by its crystalline solid form and solubility in water. With a molecular weight of 142.16 g/mol, this compound is primarily used for forming chemical bonds between different molecules, making it a vital ingredient in various industries.

Uses

Used in Chemical Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used as a crosslinking agent for enhancing the properties of resins, rubber, and adhesives. Its ability to form chemical bonds between molecules contributes to the improved performance and durability of these materials.
Used in Analytical Chemistry:
N,N'-DIACETYLETHYLENEDIAMINE is used as a chelating agent, playing a crucial role in the analysis and detection of various chemical compounds. Its chelating properties allow for the selective binding and separation of target molecules, facilitating accurate measurements and analyses.
Used in Pharmaceutical Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used in the preparation of pharmaceuticals, where its crosslinking capabilities can be employed to create stable and effective drug formulations. Its role in the synthesis of certain medications highlights its importance in the development of new therapeutic agents.
Used in Textile Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used as a crosslinking agent in textiles, improving the strength, durability, and resistance to environmental factors such as UV radiation and chemical exposure. This enhances the performance and longevity of textile products.
Used in Plastics Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used in the production of plastics to improve their structural integrity and resistance to wear and tear. Its crosslinking properties contribute to the development of high-performance plastic materials for various applications.
Used in Coatings Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used in the formulation of coatings to enhance their adhesion, durability, and resistance to environmental factors. Its crosslinking capabilities improve the overall performance and longevity of coated surfaces.
Safety Precautions:
It is important to handle N,N'-DIACETYLETHYLENEDIAMINE with caution, as it can be toxic if ingested, inhaled, or absorbed through the skin. Proper safety measures, such as wearing protective gear and following handling guidelines, should be strictly adhered to during its use in various applications.

Synthetic route

acetic anhydride (108-24-7) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
yttria-stabilized zirconia In acetonitrile for 2.5h; Heating;	99%
With silica gel for 0.05h; Microwave irradiation; neat (no solvent);	98%
With polydopamine sulfamic acid-functionalized silica gel nanocatalyst In neat (no solvent) at 20℃; for 0.2h;	96%

2,4,6-triacetyloxy-1,3,5-triazine (13483-16-4) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
at 25℃; for 0.0833333h; neat (no solvent);	99%

1,1,1-trichloroacetone (918-00-3) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
In hexane at 25℃;	97%

acetic acid (64-19-7) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
at 80 - 160℃;	93%
In water at 240 - 250℃; for 0.666667h;
With lithium chloride supported solid acid catalyst at 110 - 120℃; for 2h; Temperature; Large scale;

1,8-bis(acetylamino)-3,6-diaza-4,5-dimethyl-3,5-octadiene (137465-85-1) → N,N'-diacetylethylenediamine (871-78-3) + 1-isocyano-2-(N-acetylamino)-ethane (137465-87-3)

Conditions	Yield
With oxygen; rose bengal In acetonitrile at 13℃; for 11h; Irradiation;	A 87% B 87%

ethylenediamine (107-15-3) + microgel-supported-CH3CO → monoacetylaminoethylamine (1001-53-2) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
In tetrahydrofuran at 25℃; for 14h; Inert atmosphere;	A 83.5% B 9.9%

ethyl acetate (141-78-6) + ethylenediamine (107-15-3) → monoacetylaminoethylamine (1001-53-2) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
at 100℃; for 36h;	A 81% B n/a
at 20℃; for 6h;	A 70% B n/a
at 20℃;
at 100℃;

acetic acid (64-19-7) + ethylenediamine (107-15-3) → lysidine (534-26-9) + monoacetylaminoethylamine (1001-53-2) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With copper In benzene at 80℃; for 5h;	A 74% B n/a C n/a

C4H9ClN2O (321746-35-4) + monoacetylaminoethylamine (1001-53-2) → 1,2-bis(2-acetamidoethyl)-3-(acetamidomethyl)diaziridine (1021441-10-0) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With potassium carbonate In chloroform at 15℃; under 3750380 Torr; for 48h;	A 57% B n/a

ethylenediamine (107-15-3) + ethyl 2-acetylacetoacetate (603-69-0) → N,N'-diacetylethylenediamine (871-78-3) + ethyl (2Z)-3-[(2-{[(1Z)-3-ethoxy-1-methyl-3-oxoprop-1-enyl]amino}ethyl)amino]but-2-enoate (23652-55-3)

Conditions	Yield
In diethyl ether at 20℃;	A 48% B n/a

carbon dioxide (124-38-9) + ethylenediamine (107-15-3) + acetonitrile (75-05-8) → imidazolidone (120-93-4) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h;	A 27% B n/a

(N-chloromethyl)acetamide (44398-42-7) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With copper; benzene

1,2-ethanediamine monohydrate (6780-13-8) + acetic anhydride (108-24-7) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
Erhitzen bis der Siedepunkt auf 170grad bis 175grad gestiegen ist;

ethyl acetate (141-78-6) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

N-methyl-acetamide (79-16-3) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With di-tert-butyl peroxide

acetamide (60-35-5) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

N-methyl-acetamide (79-16-3) → N,N'-diacetylethylenediamine (871-78-3) + N,N'-dimethylsuccinamide (16873-50-0) + N-acetyl-β-alanine N'-methylamide (33233-69-1)

Conditions	Yield
In solid at -196.1℃; Product distribution; Mechanism; Irradiation; also in aqueous solution;

N,Ν,Ν'-triacetylenediamine (137706-80-0) → peracetic acid (79-21-0) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With 1,2-ethanediylbistetraphosphonic acid; dihydrogen peroxide at 25℃; Kinetics; Thermodynamic data; various pH values (carbonate buffer), other temperatures; ΔH(excit.), ΔS(excit.);

N,Ν,Ν'-triacetylenediamine (137706-80-0) → N,N'-diacetylethylenediamine (871-78-3) + acetic acid (64-19-7)

Conditions	Yield
With water at 25℃; Rate constant; pH 9.60 and 10.47 (carbonate buffer);

acetic anhydride (108-24-7) + ethylenediamine (107-15-3) → lysidine (534-26-9) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
	A 11 g B 80 g

acetic acid (64-19-7) + ethylenediamine (107-15-3) → 1H-imidazole (288-32-4) + lysidine (534-26-9) + 2-methylimidazole (693-98-1) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
5% platinum on alumina at 280 - 400℃;
5% platinum on alumina at 280 - 400℃; Product distribution; var. catalysts, temp. and contact time;

acetic acid (64-19-7) + ethylenediamine (107-15-3) → lysidine (534-26-9) + 1,2-dimethyl-1H-imidazole (1739-84-0) + 2-methylimidazole (693-98-1) + N,N'-diacetylethylenediamine (871-78-3) + 1-ethyl-2-methyl-4,5-dihydro-1H-imidazole (4814-93-1)

Conditions	Yield
With hydrogen; Pt/Al AP-64K catalyst at 280℃; Product distribution; var. temp. and molar ratio of ragents;

acetic acid (64-19-7) + ethylenediamine (107-15-3) → lysidine (534-26-9) + 1-ethyl-2-methylimidazole (21202-52-8) + 2-methylimidazole (693-98-1) + monoacetylaminoethylamine (1001-53-2) + N,N'-diacetylethylenediamine (871-78-3) + 1-ethyl-2-methyl-4,5-dihydro-1H-imidazole (4814-93-1)

Conditions	Yield
Pt/Al2O3 at 300 - 400℃; Product distribution; other ratios of reactants;

acetic acid (64-19-7) + ethylenediamine (107-15-3) → lysidine (534-26-9) + 2-methylimidazole (693-98-1) + monoacetylaminoethylamine (1001-53-2) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
γ-Al2O3 at 330℃; for 0.4h; Product distribution; var. temp. and contact time;

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → N,N'-diacetylethylenediamine (871-78-3) + N,Ν,Ν'-triacetylenediamine (137706-80-0)

Conditions	Yield
With iron(III) perchlorate In water at 20℃; for 480h; pH=2.9 - 5.5; Kinetics; Hydrolysis;

Isopropenyl acetate (108-22-5) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3) + N-acetyl-ethylenediamine

Conditions	Yield
With water

N,Ν,Ν'-triacetylenediamine (137706-80-0) + acetic acid (64-19-7) → N,N'-diacetylethylenediamine (871-78-3) + acetic anhydride (108-24-7)

Conditions	Yield
at 140℃; Kinetics; Temperature;

tetra-acetylenediamine → peracetic acid (79-21-0) + N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
With water; dihydrogen peroxide at 20℃;

N,N'-diacetylethylenediamine (871-78-3) + acetic anhydride (108-24-7) → N,Ν,Ν'-triacetylenediamine (137706-80-0)

Conditions	Yield
at 125℃; for 3h; Temperature;	99.62%

N,N'-diacetylethylenediamine (871-78-3) → tetra-acetylethylenediamine

Conditions	Yield
With acetic anhydride	98%
With acetic anhydride
With acetic anhydride
With acetic anhydride

N,N'-diacetylethylenediamine (871-78-3) + acetic anhydride (108-24-7) → ethylenediamine tetraacetic acid (117659-76-4)

Conditions	Yield
With lithium chloride supported solid acid catalyst at 130 - 140℃; for 3h; Temperature; Large scale;	93.41%

Glyoxal (131543-46-9) + N,N'-diacetylethylenediamine (871-78-3) → 1,4-diacetylpiperazine-2,3-diol (960507-67-9)

Conditions	Yield
With sodium carbonate In water at 20℃; pH=8 - 9;	90%

cobalt(II) bromide hydrate + N,N'-diacetylethylenediamine (871-78-3) → Co(2+)*2CH3CONH(CH2)2NHCOCH3*2Br(1-)*2H2O=[Co(CH3CONH(CH2)2NHCOCH3)2(H2O)2]Br2

Conditions	Yield
With 2,2-dimethoxypropane In acetonitrile 2 equiv. of ligand, 10 vol % dimethoxypropane in MeCN; slow concn.; elem. anal.;	83%

N,N'-diacetylethylenediamine (871-78-3) + acetic anhydride (108-24-7) → N,N,N',N'-tetraacetylethylenediamine (10543-57-4)

Conditions	Yield
With solid acid SO4(2-)/Al2O3 at 110 - 160℃; for 4.5h; Reagent/catalyst; Temperature;	81.9%

manganese(II) bromide tetrahydrate + N,N'-diacetylethylenediamine (871-78-3) → Mn(2+)*3CH3CONH(CH2)2NHCOCH3*2Br(1-)*H2O=Mn(CH3CONH(CH2)2NHCOCH3)3Br2*H2O

Conditions	Yield
With 2,2-dimethoxypropane In acetonitrile 2 equiv. of ligand, 10 vol % dimethoxypropane in MeCN; slow concn.; elem. anal.;	79%

nickel(II) nitrate hydrate + N,N'-diacetylethylenediamine (871-78-3) → Ni(2+)*2CH3CONH(CH2)2NHCOCH3*2NO3(1-)*3H2O=Ni(CH3CONH(CH2)2NHCOCH3)2(NO3)2*3H2O

Conditions	Yield
In methanol; acetonitrile mixing hot solns. of metal nitrate (in MeOH) with 2 equiv. ligand (in MeCN); sepn. of oil; trituration with Et2O; elem. anal.;	79%

cobalt(II) nitrate hexahydrate + N,N'-diacetylethylenediamine (871-78-3) → Co(2+)*2CH3CONH(CH2)2NHCOCH3*2NO3(1-)*2H2O=Co(CH3CONH(CH2)2NHCOCH3)2(NO3)2*2H2O

Conditions	Yield
In methanol; acetonitrile mixing hot solns. of metal nitrate (in MeOH) with 2 equiv. ligand (in MeCN); sepn. of oil; trituration with Et2O; elem. anal.;	76%

N,N'-diacetylethylenediamine (871-78-3) + nickel dibromide → Ni(2+)*2CH3CONH(CH2)2NHCOCH3*2Br(1-)*2H2O=Ni(CH3CONH(CH2)2NHCOCH3)2Br2*2H2O

Conditions	Yield
With 2,2-dimethoxypropane In acetonitrile 2 equiv. of ligand, 10 vol % dimethoxypropane in MeCN; slow concn.; elem. anal.;	66%

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate (787-07-5) + N,N'-diacetylethylenediamine (871-78-3) → 2,5-bis-(2-acetylamino-ethylamino)-terephthalic acid diethyl ester (102314-88-5)

Conditions	Yield
anschliessend Behandeln mit Jod in Aethanol;

N,N'-diacetylethylenediamine (871-78-3) → lysidine (534-26-9)

Conditions	Yield
With magnesium
With calcium oxide at 220 - 265℃; for 2h; Yield given;
With calcium oxide at 210 - 220℃; for 2h;

N,N'-diacetylethylenediamine (871-78-3) → N,N'-diethylethylenediamine (111-74-0)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

N,N'-diacetylethylenediamine (871-78-3) → but-3-ene-1,2-diamine (73314-67-7)

Conditions	Yield
bei der Destillation, teilweise;

N,N'-diacetylethylenediamine (871-78-3) → N',N'''-diphenyl-N,N''-ethanediyl-bis-acetamidine

Conditions	Yield
With phosphorus pentachloride; benzene beim Erwaermen anschliessend mit Anilin;

N,N'-diacetylethylenediamine (871-78-3) → N',N'''-bis-(4-ethoxy-phenyl)-N,N''-ethanediyl-bis-acetamidine

Conditions	Yield
aufeinanderfolgenden Umsetzen mit PCl5 und mit p-Phenetidin;

Upstream product

• 108-24-7 acetic anhydride 
• 107-15-3 ethylenediamine 
• 141-78-6 ethyl acetate 
• 137706-80-0 N,Ν,Ν'-triacetylenediamine 
• 10543-57-4 N,N,N',N'-tetraacetylethylenediamine 
• 108-22-5 Isopropenyl acetate 
• 64-17-5 ethanol 
• 124-38-9 carbon dioxide 
• 75-05-8 acetonitrile 
• 64-19-7 acetic acid 
• 13483-16-4 2,4,6-triacetyloxy-1,3,5-triazine 
• 321746-35-4 C₄H₉ClN₂O 
• 1001-53-2 monoacetylaminoethylamine 
• 603-69-0 ethyl 2-acetylacetoacetate 

Downstream Products

• 534-26-9 lysidine 
• 111-74-0 N,N'-diethylethylenediamine 
• 137706-80-0 N,Ν,Ν'-triacetylenediamine 
• 64-19-7 acetic acid 
• 79-21-0 peracetic acid 
• 1001-53-2 monoacetylaminoethylamine 
• 144697-33-6 N-ethylideneethane-1,2-diamine 
• 64-17-5 ethanol 
• 107-15-3 ethylenediamine 
• 10543-57-4 N,N,N',N'-tetraacetylethylenediamine 

Relevant articles and documents

Near-Ambient-Temperature Dehydrogenative Synthesis of the Amide Bond: Mechanistic Insight and Applications

The current existing methods for the amide bond synthesis via acceptorless dehydrogenative coupling of amines and alcohols all require high reaction temperatures for effective catalysis, typically involving reflux in toluene, limiting their potential practical applications. Herein, we report a system for this reaction that proceeds under mild conditions (reflux in diethyl ether, boiling point 34.6 °C) using ruthenium PNNH complexes. The low-temperature activity stems from the ability of Ru-PNNH complexes to activate alcohol and hemiaminals at near-ambient temperatures through the assistance of the terminal N-H proton. Mechanistic studies reveal the presence of an unexpected aldehyde-bound ruthenium species during the reaction, which is also the catalytic resting state. We further utilize the low-temperature activity to synthesize several simple amide bond-containing commercially available pharmaceutical drugs from the corresponding amines and alcohols via the dehydrogenative coupling method.

Method for catalytic synthesis of tetraacetylethylenediamine by utilizing supported lithium chloride

The invention provides a method for catalytic synthesis of tetraacetylethylenediamine by utilizing supported lithium chloride. Specifically, the method comprises the following steps: (1) sufficientlymixing a lithium chloride solution, a grinding aid dispersant and a carrier under stirring at room temperature, performing high-temperature drying, and performing grinding to obtain the supported lithium chloride solid acid catalyst; (2) quickly adding anhydrous acetic acid dropwise into ethylenediamine and a conventional catalyst; performing heating, performing a heat preservation reaction, and separating water; and adding acetic anhydride and the lithium chloride catalyst, continuing heating, and performing a reaction; and (3) performing cooling, performing crystallization, performing washing, and performing drying to obtain the tetraacetylethylenediamine. The method provided by the invention utilizes the supported lithium chloride solid acid to catalyze the synthesis of the tetraacetylethylenediamine by the ethylenediamine and an acylating reagent, and the catalyst is beneficial for recovering and can be recycled and has less pollution to the environment; the catalytic efficiency ishigh, the reaction time is effectively shortened, and the product yield can reach 90% or more; and the preparation method of the catalyst is simple, has low costs, and facilitates realizing industrial production and application of the tetraacetylethylenediamine.

Preparation of Polydopamine Sulfamic Acid-Functionalized Silica Gel as Heterogeneous and Recyclable Nanocatalyst for Acetylation of Alcohols and Amines Under Solvent-Free Conditions

To fabricate SiO2/PDA–SO3H nanocatalyst, a suitable method is designed for the loading of sulfonic acid groups on the surface of polydopamine (PDA)-encapsulated SiO2 nanoparticles. To bridge the gap between heterogeneous and homogeneous catalysis, surface functionalization of silica gel is an elegant procedure. The morphology, structure, and physicochemical features were specified using different analytical techniques including field emission scanning electron microscopy (FESEM), Fourier transformed infrared spectroscopy (FT-IR), high resolution-transmission electron microscopy (HR-TEM), energy dispersive X-ray spectroscopy (EDS), wavelength-dispersive X-ray spectroscopy (WDX), X-ray photoelectron spectroscopy (XPS), and back titration. The SiO2/PDA–SO3H nanoparticles are efficient nanocatalysts for the acetylation of many alcohols, phenols, and amines with acetic anhydride under solvent-free conditions in good to excellent yields. Moreover, the reuse and recovery of the catalyst was shown seven times without detectible loss in activity. Graphical Abstract: [Figure not available: see fulltext.]