diethylamine
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 407845259
|Reference = Merck Index, 12th Edition, 3160
|ImageFile = Et2NH.svg
|ImageClass = skin-invert
|ImageFile_Ref = {{chemboximage|correct|??}}
|ImageSize = 230
|ImageAlt = Skeletal formula of diethylamine
|ImageFile2 = Diethylamine 3D ball.png
|ImageClass2 = bg-transparent
|ImageFile2_Ref = {{chemboximage|correct|??}}
|ImageSize2 = 160
|ImageAlt2 = Ball and stick model of the diethylamine molecule
|PIN = N-Ethylethanamine
|OtherNames = (Diethyl)amine
Diethylamine (deprecated{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 671 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}})
|Section1={{Chembox Identifiers
|CASNo = 109-89-7
|CASNo_Ref = {{cascite|correct|CAS}}
|PubChem = 8021
|ChemSpiderID = 7730
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|UNII = B035PIS86W
|UNII_Ref = {{fdacite|correct|FDA}}
|EINECS = 203-716-3
|UNNumber = 1154
|MeSHName = diethylamine
|ChEMBL = 1189
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 85259
|RTECS = HZ8750000
|Beilstein = 605268
|SMILES = CCNCC
|StdInChI = 1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = HPNMFZURTQLUMO-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
|C=4 | H=11 | N=1
|Appearance = Colourless liquid
|Odor = fishy, ammonical
|Density = 0.7074 g mL−1
|MeltingPtK = 223.35
|BoilingPtK = 327.9 to 329.5
|Solubility = Miscible
|LogP = 0.657
|VaporPressure = 24.2–97.5 kPa
|HenryConstant = 150 μmol Pa−1 kg−1
|pKa = 10.98 (of ammonium form)
|RefractIndex = 1.385
|MagSus = −56.8·10−6 cm3/mol
}}
|Section3={{Chembox Thermochemistry
|DeltaHf = −131 kJ mol−1
|DeltaHc = −3.035 MJ mol−1
|HeatCapacity = 178.1 J K−1 mol−1
}}
|Section4={{Chembox Hazards
|ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/d3056.htm hazard.com]
|GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}}
|GHSSignalWord = DANGER
|HPhrases = {{h-phrases|225|302|312|314|332}}
|PPhrases = {{p-phrases|210|280|305+351+338|310}}
|NFPA-H = 3
|NFPA-F = 3
|NFPA-R = 1
|FlashPtC = -23
|AutoignitionPtC = 312
|ExploLimits = 1.8–10.1%
|PEL = TWA 25 ppm (75 mg/m3){{PGCH|0209}}
|REL = TWA 10 ppm (30 mg/m3) ST 25 ppm (75 mg/m3)
|LC50 = 4000 ppm (rat, 4 hr){{IDLH|109897|Diethylamine}}
|LD50 = 540 mg/kg (rat, oral)
500 mg/kg (mouse, oral)
}}
|Section5={{Chembox Related
|OtherFunction_label = amines
|OtherFunction = {{unbulleted list|Ethylamine|Dimethylamine|Trimethylamine||Triethylamine|Diisopropylamine}}
|OtherCompounds =
}}
}}
Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is classified as a secondary amine. It is a flammable, volatile weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.
Production and uses
The alumina-catalyzed reaction makes diethylamine from ethanol and ammonia. Diethylamine is obtained together with ethylamine and triethylamine. Annual production of the three ethylamines was estimated in 2000 to be 80,000,000 kg.{{Ullmann|author=Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke|title=Amines, Aliphatic|year=2005|DOI=10.1002/14356007.a02_001}}
Diethylamine is used in the production of corrosion inhibitor N,N-diethylaminoethanol, by reaction with ethylene oxide. It is also a precursor to a wide variety of other commercial products. It is also sometimes used in the illicit production of LSD.{{cite web |last1=Shulgin |first1=Alexander |title=Erowid Online Books:"TIHKAL" - #26 LSD-25 |url=https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml |website=www.erowid.org |access-date=12 August 2019}}
Organic chemistry
As the most abundantly available secondary amine that is liquid at room temperature, diethylamine has been extensively deployed in chemical synthesis. Its reactions illustrate the pattern seen for many other dialkylamines. It participates in Mannich reactions involving the installation of diethylaminomethyl substituents.{{cite journal |doi=10.15227/orgsyn.023.0030 |author=Charles E. Maxwell|title=β-Diethylaminomethylacetophenone Hydrochloride |journal=Organic Syntheses |date=1943 |volume=23 |page=30 }}{{cite journal |doi=10.15227/orgsyn.027.0020 |author=C. F. H. Allen and J. A. VanAllan
|title=Diethylaminoacetonitrile |journal=Organic Syntheses |date=1947 |volume=27 |page=20 }}{{cite journal |doi=10.15227/orgsyn.037.0018 |author=Alfred L. Wilds, Robert M. Nowak, Kirtland E. McCaleb|title=1-Diethylamino-3-Butanone |journal=Organic Syntheses |date=1957 |volume=37 |page=18 }} Alkylation gives the tertiary amine.{{cite journal |author=W. W. Hartman|doi=10.15227/orgsyn.014.0028 |title=β-Diethylaminoethyl Alcohol |journal=Organic Syntheses |date=1934 |volume=14 |page=28 }} With trimethylsilyl chloride, it reacts to give the silylamide.{{cite journal |author=W. J. Middleton, E. M. Bingham|doi=10.15227/orgsyn.057.0050 |title=Diethylaminosulfur Trifluoride |journal=Organic Syntheses |date=1977 |volume=57 |page=50 }}
Supramolecular structure
Diethylamine is the smallest and simplest molecule that features a supramolecular helix as its lowest energy aggregate. Other similarly sized hydrogen-bonding molecules favor cyclic structures.{{cite journal |author1=Felix Hanke |author2=Chloe J. Pugh |author3=Ellis F. Kay |author4=Joshua B. Taylor |author5=Stephen M. Todd |author6=Craig M. Robertson |author7=Benjamin J. Slater |author8=Alexander Steiner | title = The simplest supramolecular helix | journal = Chemical Communications | year = 2018 | volume = 54 |issue=47 |pages=6012–6015 | doi = 10.1039/C8CC03295E|pmid=29796532 }}
Safety
References
{{Reflist}}
External links
- [http://nj.gov/health/eoh/rtkweb/documents/fs/0690.pdf Hazardous Substance Fact Sheet]
- [https://www.cdc.gov/niosh/npg/npgd0209.html CDC - NIOSH Pocket Guide to Chemical Hazards]