Diethylhydroxylamine

{{chembox

| Watchedfields = changed

| verifiedrevid = 443638453

| Name =

| ImageFileL1 = N,N-Diethyl hydroxylamine V1.svg

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 180

| ImageAltL1 = Skeletal formula of diethylhydroxylamine

| ImageFileR1 = Diethylhydroxylamine 3D ball.png

| ImageSizeR1 = 145

| ImageAltR1 = Ball-and-stick model of the diethylhydroxylamine molecule

| PIN = N-Ethyl-N-hydroxyethanamine

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo = 3710-84-7

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 19463

| ChemSpiderID = 18340

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 314I05EDVH

| UNII_Ref = {{fdacite|correct|FDA}}

| EINECS = 223-055-4

| UNNumber = 1993

| MeSHName = N,N-diethylhydroxylamine

| RTECS = NC3500000

| Beilstein = 1731349

| SMILES = CCN(O)CC

| StdInChI = 1S/C4H11NO/c1-3-5(6)4-2/h6H,3-4H2,1-2H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FVCOIAYSJZGECG-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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| Section2 = {{Chembox Properties

| C=4 | H=11 | N=1 | O=1

| Appearance = Colorless liquid

| Odor = Ammoniacal

| Density = 867 mg mL−1

| MeltingPtC = -26 to -25

| BoilingPtK = 400.7

| Solubility = Miscible

| VaporPressure = 500 Pa (at 0 °C)

| pKa = 5.67 (est) Hilal SH et al; pp. 291-353 in Quantitative Treatments of Solute/Solvent Interactions: Theoretical and Computational Chemistry Vol. 1 NY, NY: Elsevier (1994). SPARC (Software Process Automation Reaction Chemistry) Available from, as of Dec 7, 2007: http://ibmlc2.chem.uga.edu/sparc/

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| Section3 = {{Chembox Thermochemistry

| DeltaHf = −175.47–−174.03 kJ mol−1

| DeltaHc = −2.97201–−2.97069 MJ mol−1

| HeatCapacity = 370.8 J K−1 mol−1

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| Section4 = {{Chembox Hazards

| GHSPictograms = {{gHS flame}} {{gHS exclamation mark}}

| GHSSignalWord = WARNING

| HPhrases = {{h-phrases|226|312|315|319|332}}

| PPhrases = {{p-phrases|280|305+351+338}}

| ExploLimits = 1.9–10%

| LD50 = {{unbulleted list|1.3 g kg−1 (dermal, rabbit)|2.19 g kg−1 (oral, rat)}}

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| Section5 = {{Chembox Related

| OtherFunction_label = alkanols

| OtherFunction = {{unbulleted list|N-Methylethanolamine|Dimethylethanolamine|Diethylethanolamine|Diethanolamine|N,N-Diisopropylaminoethanol|Methyl diethanolamine|Triethanolamine|Bis-tris methane|Meglumine}}

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| Section6 =

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Diethylhydroxylamine (DEHA) is an organic compound with the formula (C2H5)2NOH. Strictly, this is N,N-diethylhydroxylamine. It has an isomer, N,O-diethylhydroxylamine with the formula EtNHOEt. Pure N,N-diethylhydroxylamine is a colorless liquid, although it is usually encountered as a colourless-to-yellow solution in water with an amine-like odor.

DEHA can be synthesised from a reaction between triethylamine and a peroxide.

Applications

DEHA is largely used as an oxygen scavenger in water treatment.

It is a volatile oxygen scavenger{{cite journal |last1=Cáceres |first1=T. |last2=Lissi |first2=E. A. |last3=Sanhueza |first3=E. |title=Autooxidation of diethyl hydroxylamine |journal=International Journal of Chemical Kinetics |date=November 1978 |volume=10 |issue=11 |pages=1167–1182 |doi=10.1002/kin.550101107}}{{cite journal |last1=Shaffer |first1=Dean |last2=Heicklen |first2=Julian |title=Oxidation of diethylhydroxylamine in water solution at 25-80.degree. |journal=The Journal of Physical Chemistry |date=August 1986 |volume=90 |issue=18 |pages=4408–4413 |doi=10.1021/j100409a039}} and reacts in a ratio of 2.8/1 DEHA/O2. It is employed in high pressure (>70 bar) boiler systems due to a very low rate of reaction at low temperatures and pressures. Due to its volatility, it acts as an oxygen scavenger throughout the entire boiler system due to steam carryover.

DEHA also reacts with ferrous metals to form a passivized film of magnetite throughout the boiler system. The reduction of toxic heavy metals, such as hexavalent chromium to their more environmentally-friendly counterparts like trivalent chromium, is also performed using aqueous solutions containing DEHA.

Several other applications include its use as:

  1. Polymerisation inhibitor
  2. Color stabilizer (photographics)
  3. Corrosion inhibitor
  4. Discoloration inhibitor (phenolics)
  5. Antiozonant
  6. Radical scavenger{{cite journal |last1=Abuin |first1=E. |last2=Encina |first2=M. V. |last3=Diaz |first3=S. |last4=Lissi |first4=E. A. |title=On the reactivity of diethyl hydroxyl amine toward free radicals |journal=International Journal of Chemical Kinetics |date=July 1978 |volume=10 |issue=7 |pages=677–686 |doi=10.1002/kin.550100704}}

References