Ethylenediamine

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Names
Preferred IUPAC name

Ethane-1,2-diamine[2]

Other names

Edamine,[1] 1,2-Diaminoethane, 'en' when a ligand

Identifiers

CAS Number

* 107-15-3 Y

3D model (JSmol)

* Interactive image

Abbreviations  | en

Beilstein Reference

| 605263
ChEBI |

* CHEBI:30347 Y

ChEMBL |

* ChEMBL816 Y

ChemSpider |

* 13835550 Y

EC Number |

* 203-468-6

Gmelin Reference

| 1098
KEGG |

* D01114 Y

MeSH | ethylenediamine

PubChem CID

* 3301

RTECS number |

* KH8575000

UNII |

* 60V9STC53F Y

UN number | 1604

InChI

* InChI=1S/C2H8N2/c3-1-2-4/h1-4H2 Y

Key: PIICEJLVQHRZGT-UHFFFAOYSA-N Y

SMILES

* NCCN

Properties

Chemical formula

| C2H8N2
Molar mass | 60.100 g·mol−1
Appearance  | Colorless liquid[3]
Odor | Ammoniacal[3]
Density | 0.90 g/cm3[3]
Melting point |  8 °C (46 °F; 281 K)[3]
Boiling point |  116 °C (241 °F; 389 K)[3]

Solubility in water

| miscible
log P | −2.057
Vapor pressure | 1.3 kPa (at 20 °C)

Henry's law
constant (kH)

| 5.8 mol Pa−1 kg−1

Magnetic susceptibility (χ)

* −46.26×10−6 cm3 mol−1
* −76.2×10−6 cm3 mol−1 (HCl salt)

Refractive index (nD)

| 1.4565
Thermochemistry

Heat capacity (C)

| 172.59 J K−1 mol−1

Std molar
entropy (S ~~o~~ 298)

| 202.42 J K−1 mol−1

Std enthalpy of
formation (ΔfH⦵298)

| −63.55 to −62.47 kJ mol−1

Std enthalpy of
combustion (ΔcH⦵298)

| −1.8678 to −1.8668 MJ mol−1
Hazards
GHS pictograms |
GHS Signal word | DANGER

GHS hazard statements

| H226, H311, H302, H332, H314, H334, H317, H412

GHS precautionary statements

| P405, P102, P260, P280, P305+351+338, P101, P308+313, P273, P501
NFPA 704 (fire diamond)  |

Flash point |  34 °C (93 °F; 307 K)[3]

Autoignition
temperature

|  385 °C (725 °F; 658 K)[3]
Explosive limits | 2.7–16%
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 500 mg/kg (oral, rat)
470 mg/kg (oral, guinea pig)
1160 mg/kg (oral, rat)[5]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 10 ppm (25 mg/m3)[4]

REL (Recommended)

| TWA 10 ppm (25 mg/m3)[4]

IDLH (Immediate danger)

| 1000 ppm[4]
Related compounds

Related alkanamines

| 1,2-Diaminopropane, 1,3-Diaminopropane

Related compounds

| Ethylamine, Ethylenedinitramine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998.[6] Ethylenediamine is the first member of the so-called polyethylene amines.

## Contents

* 1 Synthesis
* 2 Applications
* 2.1 Precursor to chelation agents, drugs, and agrochemicals
* 2.2 Pharmaceutical ingredient
* 2.3 Role in polymers
* 2.4 Tetraacetylethylenediamine
* 2.5 Other applications
* 3 Coordination chemistry
* 3.1 Related ligands
* 4 Safety
* 5 References
* 6 External links

## Synthesis

See also: ethyleneamines

Ethylenediamine is produced industrially by treating 1,2-dichloroethane with ammonia under pressure at 180 °C in an aqueous medium:[6][7]

In this reaction hydrogen chloride is generated, which forms a salt with the amine. The amine is liberated by addition of sodium hydroxide and can then be recovered by Rectification (chemical/process engineering) (de). Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-products.

Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:[8]

This process involves passing the gaseous reactants over a bed of nickel heterogeneous catalysts.

It can be produced in the lab by the reaction of ethylene glycol and urea.[citation needed]

Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation.[9]

## Applications

Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with carboxylic acids (including fatty acids), nitriles, alcohols (at elevated temperatures), alkylating agents, carbon disulfide, and aldehydes and ketones. Because of its bifunctional nature, having two amino groups, it readily forms heterocycles such as imidazolidines.

### Precursor to chelation agents, drugs, and agrochemicals

A most prominent derivative of ethylenediamine is the chelating agent EDTA, which is derived from ethylenediamine via a Strecker synthesis involving cyanide and formaldehyde. Hydroxyethylethylenediamine is another commercially significant chelating agent.[6] Numerous bio-active compounds and drugs contain the N–CH2–CH2–N linkage, including some antihistamines.[10] Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram. Some imidazoline-containing fungicides are derived from ethylenediamine.[6]

### Pharmaceutical ingredient

Ethylenediamine is an ingredient in the common bronchodilator drug aminophylline, where it serves to solubilize the active ingredient theophylline. Ethylenediamine has also been used in dermatologic preparations, but has been removed from some because of causing contact dermatitis.[11] When used as a pharmaceutical excipient, after oral administration its bioavailability is about 0.34, due to a substantial first-pass effect. Less than 20% is eliminated by renal excretion.[12]

Ethylenediamine-derived antihistamines are the oldest of the five classes of first-generation antihistamines, beginning with piperoxan aka benodain, discovered in 1933 at the Pasteur Institute in France, and also including mepyramine, tripelennamine, and antazoline. The other classes are derivatives of ethanolamine, alkylamine, piperazine, and others (primarily tricyclic and tetracyclic compounds related to phenothiazines, tricyclic antidepressants, as well as the cyproheptadine-phenindamine family)

### Role in polymers

Ethylenediamine, because it contains two amine groups, is a widely used precursor to various polymers. Condensates derived from formaldehyde are plasticizers. It is widely used in the production of polyurethane fibers. The PAMAM class of dendrimers are derived from ethylenediamine.[6]

### Tetraacetylethylenediamine

The bleaching activator tetraacetylethylenediamine is generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and a surfactant in gasoline and motor oil.

### Other applications

* as a solvent, it is miscible with polar solvents and is used to solubilize proteins such as albumins and casein. It is also used in certain electroplating baths.
* as a corrosion inhibitor in paints and coolants.
* ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.
* chemicals for color photography developing, binders, adhesives, fabric softeners, curing agents for epoxies, and dyes.
* as a compound to sensitize nitromethane into an explosive. This mixture was used at Picatinny Arsenal during World War II, giving the nitromethane and ethylenediamine mixture the nickname PLX, or Picatinny Liquid Explosive.

## Coordination chemistry

Ethylenediamine is a well-known bidentate chelating ligand for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand. It is often abbreviated "en" in inorganic chemistry. The complex [Co(en)3]3+ is an archetypical chiral tris-chelate complex. The salen ligands, some of which are used in catalysis, are derived from the condensation of salicylaldehydes and ethylenediamine.

### Related ligands

Related derivatives of ethylenediamine include ethylenediaminetetraacetic acid (EDTA), tetramethylethylenediamine (TMEDA), and tetraethylethylenediamine (TEEDA). Chiral analogs of ethylenediamine include 1,2-diaminopropane and trans-diaminocyclohexane.

## Safety

Ethylenediamine, like ammonia and other low-molecular weight amines, is a skin and respiratory irritant. Unless tightly contained, liquid ethylenediamine will release toxic and irritating vapors into its surroundings, especially on heating. The vapors absorb moisture from humid air to form a characteristic white mist, which is extremely irritating to skin, eyes, lungs and mucus membranes.

## References

1. ↑ "32007R0129". European Union. 12 February 2007. Annex II. http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:32007R0129:EN:NOT.
2. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 676. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 Record  in the GESTIS Substance Database of the Institute for Occupational Safety and Health
4. ↑ 4.0 4.1 4.2 NIOSH Pocket Guide to Chemical Hazards. "#0269". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0269.html.
5. ↑ "Ethylenediamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/107153.html.
6. ↑ 6.0 6.1 6.2 6.3 6.4 Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH Verlag. doi:10.1002/14356007.a02_001. ISBN 3-527-30673-0.
7. ↑ Arpe, Hans-Jürgen (2007). Industrielle Organische Chemie (6th ed.). Wiley VCH. p. 245.
8. ↑ Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH
9. ↑ Rollinson, Carl L.; Bailar, John C. Jr. (1946). "Tris(ethylenediamine)chromium(III) Salts". Inorganic Syntheses. 2. pp. 196–200. doi:10.1002/9780470132333.ch60. ISBN 978-0-470-13233-3.
10. ↑ Kotti, S. R. S. S.; Timmons, C.; Li, G. (2006). "Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry". Chemical Biology & Drug Design 67 (2): 101–114. doi:10.1111/j.1747-0285.2006.00347.x. PMID 16492158.
11. ↑ Hogan DJ (January 1990). "Allergic contact dermatitis to ethylenediamine. A continuing problem.". Dermatol Clin 8 (1): 133–6. doi:10.1016/S0733-8635(18)30536-9. PMID 2137392.
12. ↑ Zuidema, J. (1985-08-23). "Ethylenediamine, profile of a sensitizing excipient". Pharmacy World & Science 7 (4): 134–140. doi:10.1007/BF02097249. PMID 3900925.

## External links

* IRIS EPA Ethylenediamine
* CDC - NIOSH Pocket Guide to Chemical Hazards
* Chemical data

* v
* t
* e

Motor fuels

Fuel types|

* Gasoline/petrol
* Diesel
* Biodiesel
* Lead Replacement Petrol
* Kerosene
* Compressed natural gas
* Hydrogen
* Ethanol
* Butanol fuel
* Racing fuel (Tetraethyllead)

Fuel additives|

* Butyl rubber
* Butylated hydroxytoluene
* 1,2-Dibromoethane
* 1,2-Dichloroethane
* Dimethyl methylphosphonate
* 2,4-Dimethyl-6-tert-butylphenol
* Dinonylnaphthylsulfonic acid
* 2,6-Di-tert-butylphenol
* Ecalene
* Ethylenediamine
* Metal deactivator
* Methyl tert-butyl ether
* Nitromethane
* Tetraethyllead
* Tetranitromethane

Fluids|

* Motor oil
* Antifreeze
* Automatic transmission fluid
* Brake fluid
* Gear oil
* Windshield washer fluid

Retail|

* Fuel card
* Full service
* MTBE controversy
* Pay at the pump

* v
* t
* e

Antioxidants

Food antioxidants|

* 6-Hydroxymelatonin
* Acetyl-L-carnitine (ALCAR)
* Alpha-lipoic acid (ALA)
* Ascorbic acid (vitamin C)
* Carotenoids (vitamin A)
* Curcumin
* Edaravone
* Polyphenols
* Glutathione
* Hydroxytyrosol
* L-carnitine
* Ladostigil
* Melatonin
* Mofegiline
* N-Acetylcysteine (NAC)
* N-Acetylserotonin (NAS)
* Oleocanthal
* Oleuropein
* Rasagiline
* Resveratrol
* Selegiline
* Selenium
* Tocopherols (vitamin E)
* Tocotrienols (vitamin E)
* Tyrosol
* Ubiquinone (coenzyme Q)
* Uric acid

Fuel antioxidants|

* Butylated hydroxytoluene
* 2,6-Di-tert-butylphenol
* 1,2-Diaminopropane
* 2,4-Dimethyl-6-tert-butylphenol
* Ethylenediamine

Measurements|

* Folin method
* ORAC
* TEAC
* FRAP

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Ethylenediamine&oldid=3719586"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H311]: Toxic in contact with skin
*[H302]: Harmful if swallowed
*[H332]: Harmful if inhaled
*[H314]: Causes severe skin burns and eye damage
*[H334]: May cause allergy or asthma symptoms of breathing difficulties if inhaled
*[H317]: May cause an allergic skin reaction
*[H412]: Harmful to aquatic life with long lasting effects
*[P405]: Store locked up
*[P102]: Keep out of reach of children
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P101]: If medical advice is needed, have product container or label at hand
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P273]: Avoid release to the environment
*[P501]: Dispose of contents/container to …
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