Diethylamine

Structural formula
General
Surname	Diethylamine
other names	DEA; N -ethylethanamine;
Molecular formula	C 4 H 11 N
Brief description	colorless, highly flammable liquid with an amine-like odor
External identifiers / databases
EC number	203-716-3
ECHA InfoCard	100.003.380
PubChem	8021
Wikidata	Q414196
properties
Molar mass	73.14 g mol −1
Physical state	liquid
density	0.71 g cm −3
Melting point	−50 ° C
boiling point	56 ° C
Vapor pressure	256 h Pa (20 ° C); 392 hPa (30 ° C); 581 hPa (40 ° C); 838 hPa (50 ° C);
pK s value	10.98 (protonated)
solubility	completely miscible with water
Refractive index	1.3864
safety instructions
H and P phrases	H: 225-302 + 332-311-314-335
	P: 210-240-280-301 + 330 + 331-302 + 352-305 + 351 + 338-308 + 310-403 + 233
MAK	DFG / Switzerland: 5 ml m −3 or 15 mg m −3
Toxicological data	540 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Diethylamine is a chemical compound from the group of aliphatic secondary amines .

Extraction and presentation

Diethylamine can be obtained by reacting ethanol with ammonia , which also results in ethylamine and triethylamine .

properties

The aqueous solution of diethylamine has a strongly alkaline reaction . Diethylamine decomposes from around 500 ° C. It has a dynamic viscosity of 0.34 mPas at 25 ° C.

Safety characteristics

Diethylamine forms highly flammable vapor-air mixtures with air. The compound has a flash point below −20 ° C. The explosion range lies between 1.7% by volume (50 g / m ³ ) as the lower explosion limit (LEL) and 10.1% by volume (305 g / m ³ ) as the upper explosion limit (UEL). The limit gap width was determined to be 1.15 mm (50 ° C). This results in an assignment to explosion group IIA. The ignition temperature is 305 ° C. The substance therefore falls into temperature class T2.

use

Diethylamine is used in the production of rubber , textile and flotation chemicals , synthetic resins, dyes and pharmaceuticals, insecticides , galvanic baths and polymerization retarders, and as a pH value regulator and buffer substance. It can also be used to make the neurotoxin tabun .

Supramolecular structure

Supramolecular helix

Diethylamine is the smallest and simplest molecule that has a supramolecular helix as an aggregate with the lowest energy. Other similarly small hydrogen-bonded molecules prefer cyclic structures.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r Entry on diethylamine in the GESTIS substance database of the IFA , accessed on March 26, 2018(JavaScript required) .
↑ HK Hall: Correlation of the Base Strengths of Amines. In: Journal of the American Chemical Society. 79, 1957, p. 5441, doi : 10.1021 / ja01577a030 .
↑ Steven Pedersen: Understanding the Principles of Organic Chemistry: A Laboratory Course. Cengage Learning, 2010, ISBN 978-0-495-82993-5 , p. 23 ( limited preview in Google Book Search).
↑ ^a ^b ^c data sheet diethylamine (PDF) from Merck , accessed on January 21, 2011.
↑ Entry on Diethylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values , accessed on August 28, 2019.
↑ ^a ^b ^c Sorbe - Safety-related characteristics of chemical substances, 131. Supplementary delivery 8/2009, ecomed-Verlag.
^ Robert Turkington: Chemicals Used for Illegal Purposes . John Wiley & Sons, 2009, ISBN 978-0-470-18780-7 , pp. 324 ( books.google.de ).
↑ Felix Hanke, Chloe J. Pugh, Ellis F. Kay, Joshua B. Taylor, Stephen M. Todd, Craig M. Robertson, Benjamin J. Slater, Alexander Steiner: The simplest supramolecular helix . In: Chemical Communications . tape 54 , 2018, doi : 10.1039 / C8CC03295E .
↑ External identifiers or database links for diethylammonium bromide: CAS number: 6274-12-0, EC number: 228-466-2, ECHA InfoCard: 100.025.879 , Wikidata : Q82860734 .
↑ External identifiers of or database links to N- (trimethylsilyl) diethylamine : CAS number: 996-50-9, EC number: 213-637-6, ECHA InfoCard: 100.012.397 , PubChem : 70454 , ChemSpider : 63633 , Wikidata : Q3869305 .
↑ External identifiers or database links to diethylamine salicylate: CAS number: 4419-92-5, EC number: 224-586-4, ECHA InfoCard: 100.022.353 , PubChem : 9837223 , ChemSpider : 19278 , Wikidata : Q27262917 .
↑ External identifiers or database links for diethylammonium acetate: CAS number: 20726-63-0, EC number: 243-990-1, ECHA InfoCard: 100.039.976 , Wikidata : Q81993222 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r Entry on diethylamine in the GESTIS substance database of the IFA , accessed on March 26, 2018(JavaScript required) .

[2] HK Hall: Correlation of the Base Strengths of Amines. In: Journal of the American Chemical Society. 79, 1957, p. 5441, doi : 10.1021 / ja01577a030 .

[orgchemistry-3] Steven Pedersen: Understanding the Principles of Organic Chemistry: A Laboratory Course. Cengage Learning, 2010, ISBN 978-0-495-82993-5 , p. 23 ( limited preview in Google Book Search).

[Merck-4] ta sheet diethylamine (PDF) from Merck , accessed on January 21, 2011.

[CLP_100.003.380-5] Entry on Diethylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values , accessed on August 28, 2019.

[Sorbe-7] Sorbe - Safety-related characteristics of chemical substances, 131. Supplementary delivery 8/2009, ecomed-Verlag.

[8] Robert Turkington: Chemicals Used for Illegal Purposes . John Wiley & Sons, 2009, ISBN 978-0-470-18780-7 , pp. 324 ( books.google.de ).

[9] Felix Hanke, Chloe J. Pugh, Ellis F. Kay, Joshua B. Taylor, Stephen M. Todd, Craig M. Robertson, Benjamin J. Slater, Alexander Steiner: The simplest supramolecular helix . In: Chemical Communications . tape 54 , 2018, doi : 10.1039 / C8CC03295E .

[10] External identifiers or database links for diethylammonium bromide: CAS number: 6274-12-0, EC number: 228-466-2, ECHA InfoCard: 100.025.879 , Wikidata : Q82860734 .

[11] External identifiers of or database links to N- (trimethylsilyl) diethylamine : CAS number: 996-50-9, EC number: 213-637-6, ECHA InfoCard: 100.012.397 , PubChem : 70454 , ChemSpider : 63633 , Wikidata : Q3869305 .

[12] External identifiers or database links to diethylamine salicylate: CAS number: 4419-92-5, EC number: 224-586-4, ECHA InfoCard: 100.022.353 , PubChem : 9837223 , ChemSpider : 19278 , Wikidata : Q27262917 .

[13] External identifiers or database links for diethylammonium acetate: CAS number: 20726-63-0, EC number: 243-990-1, ECHA InfoCard: 100.039.976 , Wikidata : Q81993222 .