Diethanolamine

Structural formula
General
Surname	Diethanolamine
other names	2 - [(2-Hydroxyethyl) amino] ethan-1-ol ( IUPAC ); Dihydroxydiethylamine; 2,2'-iminodiethanol; 2,2'-iminobisethanol; Aminodiethanol; Bis-hydroxyethylamine; DEA; DOLA;
Molecular formula	C 4 H 11 NO 2
Brief description	colorless, hygroscopic solid with an ammonia-like odor
External identifiers / databases
EC number	203-868-0
ECHA InfoCard	100.003.517
PubChem	8113
ChemSpider	13835604
Wikidata	Q418437
properties
Molar mass	105.14 g · mol -1
Physical state	solid (also liquid due to low melting point)
density	1.1 g cm −3
Melting point	28 ° C
boiling point	269 ° C
Vapor pressure	<0.01 h Pa (20 ° C); 0.6 hPa (100 ° C);
pK s value	8.88 (25 ° C)
solubility	easily in water (954 g l −1 at 20 ° C); miscible with acetone and ethanol ; little in hydrocarbons and diethyl ether ;
safety instructions
H and P phrases	H: 302-373-315-318
	P: 273-280-301 + 312-330-305 + 351 + 338-310
MAK	DFG / Switzerland: 1 mg m −3 (measured as inhalable dust )
Toxicological data	1000–3000 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 .

Diethanolamine (according to IUPAC nomenclature: 2 - [(2-hydroxyethyl) amino] ethan-1-ol , also referred to as DEA for short ) is an organic-chemical compound from the group of amino alcohols . It is used as a raw material in the chemical industry and is used in solvents , emulsifiers and detergents and cleaning agents .

Extraction and presentation

Diethanolamine is produced on an industrial scale by reacting ethylene oxide with ammonia at temperatures of 80-140 ° C. and pressures of 70-160 bar in the presence of water and an acidic catalyst . Acidic zeolites (for example aluminosilicates ) or organic ion exchange resins in the H form (protons) are particularly preferably used.

Monoethanolamine and triethanolamine are produced as by-products . The proportion of diethanolamine and triethanolamine can be greatly increased by an excess of ethylene oxide. The molar ratio of ammonia to ethylene oxide is therefore preferably 7: 2. The complete reaction takes place preferably in stirred tank or tubular reactors. The reaction mixture is purified and worked up by multi-stage distillation in rectification columns . Separated monoethanolamine can be returned to the reactor in order to increase the overall yield of diethanolamine again.

In 1990 around 20,500 tons of diethanolamine were produced in the Federal Republic of Germany .

properties

Physical Properties

Diethanolamine is a colorless, hygroscopic solid with an ammonia-like odor. The dynamic viscosity of diethanolamine is 352 mPa · s at 30 ° C.

Chemical properties

By dehydration (elimination of water) of diethanolamine with sulfuric acid can morpholine are generated.

Safety-related parameters

Diethanolamine is considered a flammable substance. Flammable vapor-air mixtures can form above the flash point. The compound has a flash point of 176 ° C. The explosion range is between 2.1 vol.% As the lower explosion limit (LEL) and 10.6 vol.% As the upper explosion limit (UEL). The ignition temperature is 355 ° C. The substance therefore falls into temperature class T2.

use

Diethanolamine is stored industrially in temperature-controlled tanks and used as an oily liquid:

as hardener for epoxy resins , water-soluble epoxy-amine adducts for KTL resins.
as an intermediate product for the production of washing raw materials, cement additives, pesticides and drilling and cutting oils ( cooling lubricants )
as a catalyst in the production of polyurethanes
as a grinding aid for cement
as an absorbent for hydrogen sulfide (H ₂ S) and carbon dioxide (CO ₂ ) in chemical processes such as amine scrubbing and in the direct air capture process
in pharmaceutical products or in household products (shoe polishes, floor care products) as plasticizers and humectants
in cosmetics it occurs to adjust the pH value or as an impurity

Risk assessment

The International Agency for Research on Cancer (IARC) classified diethanolamine as a possible carcinogen in 2013. Diethanolamine is classified as harmful and can cause allergies . Carcinogenic nitrosamines (e.g. N- nitrosodiethanolamine ) can be formed through nitrosation of diethanolamine (with nitrites ) .

Researchers at the University of North Carolina have found that diethanolamine affects brain development in fetuses. In an animal experiment, they smeared DEA on the skin of pregnant mice and found that the newborn mice were born with brain damage. In the area of the hippocampus , brain cells grow more slowly under the influence of DEA and at the same time the death rate of the cells was increased. Cosmetics only contain a much lower dose of the substance, so that a health hazard from shampoos, for example, is unlikely.

The risk posed by DEA-containing cosmetics could even be significantly lower than the researchers stated. According to a statement from the Cosmetic, Toiletry, and Fragrance Association (CTFA), DEA has hardly ever been used in cosmetics itself. DEA is typically formed as a breakdown product of alkanolamides (reaction products of fatty acids with DEA) or can still be present in small amounts as an unreacted starting material. For the use of shampoo with a very high but realistic content of DEA-containing ingredients (and correspondingly DEA), the CTFA calculated that the dose of DEA on the skin of the mice was even a thousand times higher than the dose in shampoos. Furthermore, the CTFA points out that the biological cause of the brain change in the experiment with mice was a choline deficiency , to which mice are more sensitive than humans.

In 2012, diethanolamine was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of diethanolamine were concerns regarding high (aggregated) tonnage and widespread use as well as the dangers arising from a possible assignment to the group of CMR substances. The re-evaluation has been running since 2012 and is carried out by Germany . In order to be able to reach a final assessment, further information was requested.

Web links

Entry on Diethanolamine in the Consumer Product Information Database

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on diethanolamine in the GESTIS substance database of the IFA , accessed on April 25, 2018(JavaScript required) .
↑ Sigma-Aldrich , SDB.
↑ ^a ^b ^c ^d Toxicological assessment of diethanolamine (PDF) from the trade association for raw materials and chemical industry (BG RCI), accessed on May 1, 2018.
↑ Entry on 2,2′-iminodiethanol 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 (search for 111-42-2 or diethanolamine ), accessed on November 2, 2015.
↑ ^a ^b Patent EP1289927B1 : Process for the production of ethanolamines. Published on May 14, 2014 , applicant: BASF SE, inventor: Matthias Frauenkron, Ulrich Müller, Wolfgang Harder, Jörg Unger, Johann-Peter Melder, Anton Meier, Walter Himmel. ‌
↑ Data sheet Diethanolamine Rotipuran ^® ≥ 99% (PDF) from Carl Roth , accessed on December 14, 2010.
↑ Klaus Weissermel , Hans-Jürgen Arpe , Charlet R. Lindley, Stephen Hawkins: Chap. 7. Oxidation Products of Ethylene . In: Industrial Organic Chemistry . Wiley-VCH , 2003, ISBN 3-527-30578-5 , pp. 159-161.
↑ ^a ^b ^c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ ^a ^b Data sheet diethanolamine (laboratory) (PDF; 183 kB) at GisChem.
↑ Hautstadt.de: Information on contact allergens
↑ Official Journal of the European Union: Council Directive 76/768 / EEC on the harmonization of the legal provisions of the member states on cosmetic products (see keyword fatty acid dialkylamides and dialkanolamides) (PDF)
↑ Chemical and Veterinary Investigation Office Karlsruhe: Nitrosamines - also undesirable in cosmetic products! ( Memento from February 12, 2013 in the web archive archive.today ).
↑ IARC Monograph 101 - Diethanolamine, 2013
↑ Dermaviduals: Nitrosamines in Cosmetics - Skin at Risk?
↑ University of North Carolina: News release UNC study shows ingredient commonly found in shampoos may inhibit brain development (Engl.)
↑ fasebj.org: DEA in consumer products is safe
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 2,2'-Iminodiethanol Template: link text check / apostrophe , accessed on March 26, 2019.Template: CoRAP status / 2012

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on diethanolamine in the GESTIS substance database of the IFA , accessed on April 25, 2018(JavaScript required) .

[2] Sigma-Aldrich , SDB.

[bg-3] Toxicological assessment of diethanolamine (PDF) from the trade association for raw materials and chemical industry (BG RCI), accessed on May 1, 2018.

[CLP_100.003.517-4] Entry on 2,2′-iminodiethanol 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 .

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 111-42-2 or diethanolamine ), accessed on November 2, 2015.

[VERFAHREN-6] Patent EP1289927B1 : Process for the production of ethanolamines. Published on May 14, 2014 , applicant: BASF SE, inventor: Matthias Frauenkron, Ulrich Müller, Wolfgang Harder, Jörg Unger, Johann-Peter Melder, Anton Meier, Walter Himmel. ‌

[CARL_ROTH-7] Data sheet Diethanolamine Rotipuran ^® ≥ 99% (PDF) from Carl Roth , accessed on December 14, 2010.

[weissermel-8] Klaus Weissermel , Hans-Jürgen Arpe , Charlet R. Lindley, Stephen Hawkins: Chap. 7. Oxidation Products of Ethylene . In: Industrial Organic Chemistry . Wiley-VCH , 2003, ISBN 3-527-30578-5 , pp. 159-161.

[Brandes-9] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[bgc-10] Data sheet diethanolamine (laboratory) (PDF; 183 kB) at GisChem.

[11] Hautstadt.de: Information on contact allergens

[12] Official Journal of the European Union: Council Directive 76/768 / EEC on the harmonization of the legal provisions of the member states on cosmetic products (see keyword fatty acid dialkylamides and dialkanolamides) (PDF)

[13] Chemical and Veterinary Investigation Office Karlsruhe: Nitrosamines - also undesirable in cosmetic products! ( Memento from February 12, 2013 in the web archive archive.today ).

[14] IARC Monograph 101 - Diethanolamine, 2013

[15] Dermaviduals: Nitrosamines in Cosmetics - Skin at Risk?

[16] University of North Carolina: News release UNC study shows ingredient commonly found in shampoos may inhibit brain development (Engl.)

[17] sebj.org: DEA in consumer products is safe

[18] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 2,2'-Iminodiethanol Template: link text check / apostrophe , accessed on March 26, 2019.Template: CoRAP status / 2012