2- (2-heptadec-8-enyl-2-imidazolin-1-yl) ethanol

Structural formula
	Figure of the ( Z ) -isomer
General
Surname	2- (2-heptadec-8-enyl-2-imidazolin-1-yl) ethanol
other names	2- (8-heptadecenyl) -4,5-dihydro-1H-imidazole-1-ethanol; 1- (2-Hydroxyethyl) -2- (8-heptadecenyl) -2-imidazoline; 2- (8-heptadecenyl) -1- (β-hydroxyethyl) -2-imidazoline; N -β-hydroxyethyl-oleyl-imidazoline; Amines O;
Molecular formula	C 22 H 42 N 2 O
Brief description	colorless or yellow to brown liquid
External identifiers / databases
EC number	202-414-9
ECHA InfoCard	100.002.196
PubChem	7233
Wikidata	Q27256294
properties
Molar mass	350.58 g mol −1
Physical state	liquid
density	0.94 g cm −3 at 20 ° C
Melting point	<−15 ° C
boiling point	> 218 ° C ; 230-240 ° C at 1 mmHg; > 250 ° C ;
solubility	very slightly soluble in water (> 0.01 g · l −1 at 20 ° C ), soluble in organic solvents and in mineral oil
safety instructions
H and P phrases	H: 302-314-373-410
	P: 273-280-303 + 361 + 353-301 + 330 + 331-305 + 351 + 338
Toxicological data	1000 mg kg −1 ( LD 50 , rat , oral ) ; 88 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2- (2-Heptadec-8-enyl-2-imidazolin-1-yl) ethanol (Amine O) is an amphiphilic oleic acid derivative with an imidazoline head group, which is more widely used as a water-in-oil emulsifier and corrosion inhibitor Has.

Occurrence and representation

2- (2-Heptadec-8-enyl-2-imidazolin-1-yl) ethanol is formed when oleic acid is heated for five hours with 2- (2-aminoethylamino) ethanol [ N - (2-hydroxyethyl) ethylenediamine] up to 270 ° C with elimination of water first to the amide and then to the imidazoline. The removal of the water of reaction by azeotropic distillation with xylene creates gentler reaction conditions that result in a clear, slightly colored liquid.

properties

1- (2-Hydroxyethyl) -2- (8-heptadecenyl) -2-imidazoline is a colorless or yellow to brown, viscous, amine-like odor liquid that is sparingly soluble in water and has an alkaline reaction. In acidic conditions, the compound dissolves as an amine salt in water with foam formation.

Applications

The surfactant properties of 2- (2-heptadec-8-enyl-2-imidazolin-1-yl) -ethanol are used in drainage aids, engl. dewatering agents , with the help of which colloidal particles can aggregate and thus be removed from drilling fluids .

Especially in acidic aqueous solution, i.e. H. in protonated form, the imidazoline derivative is an excellent foaming agent.

Amine O as an additive for finishes improves the properties of fibers, yarns and textiles, such as, for example, by amphiphilic interactions with fiber surfaces. B. their colorability, handle or antistatic .

N -β-Hydroxyethyl-oleyl-imidazoline increases the binding of asphalt to sand and gravel and increases the strength of road surfaces even with a small addition (<0.25 percent by weight) to the asphalt .

As an oil-in-water emulsifier, Amine O creates stable dispersions of mineral oil in water and is used as a fuel and lubricant additive, as well as an emulsifier in cooling lubricants for metalworking. The strong anti-corrosive effect of the imidazoline derivative also comes into play in both applications . Particularly in combination with the emulsifying and anti-corrosive N-acyl sarcosine N- oleoyl sarcosine ( Sarkosyl O ), very good rust protection is achieved even at low concentrations (<0.5 weight percent).

Reaction of 2- (2-heptadec-8-enyl-2-imidazolin-1-yl) ethanol with z. B. Dimethyl sulfate on the N ¹ nitrogen of the imidazoline ring produces the neutral and readily water-soluble quaternary ammonium salt ,

which can be used as an antistatic in conditioners , textiles and paints, as well as a wetting agent or flotation agent .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Evonik Industries AG, Technical Information Varine® O
↑ ^a ^b ^c ^d BASF SE: Safety Data Sheet Amine O
↑ ^a ^b ^c ^d ^e patent US2267965 : Hydroxyalkyl glyoxalidines. Applied July 18, 1939 , published December 30, 1941 , Applicant: Carbide and Carbon Chemicals Corp., Inventor: AL Wilson. ‌
↑ Entry on 2- (2-heptadec-8-enyl-2-imidazolin-1-yl) ethanol in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Data sheet Nb-hydroxyethyl oleyl imidazoline from Sigma-Aldrich , accessed on May 15, 2016 ( PDF ).
↑ BASF SE, Lubricant Solutions, Corrosion Inhibitor amines O.
↑ ^a ^b ^c Ciba Specialty Chemicals, Ciba® Amine O: Oil soluble corrosion inhibitor .

[Evonik-1] ↑ ^a ^b ^c ^d ^e ^f Evonik Industries AG, Technical Information Varine® O

[BASF-2] BASF SE: Safety Data Sheet Amine O

[Wilson-3] ↑ ^a ^b ^c ^d ^e patent US2267965 : Hydroxyalkyl glyoxalidines. Applied July 18, 1939 , published December 30, 1941 , Applicant: Carbide and Carbon Chemicals Corp., Inventor: AL Wilson. ‌

[GESTIS-4] Entry on 2- (2-heptadec-8-enyl-2-imidazolin-1-yl) ethanol in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[Sigma-5] Data sheet Nb-hydroxyethyl oleyl imidazoline from Sigma-Aldrich , accessed on May 15, 2016 ( PDF ).

[6] BASF SE, Lubricant Solutions, Corrosion Inhibitor amines O.

[Ciba-7] Ciba Specialty Chemicals, Ciba® Amine O: Oil soluble corrosion inhibitor .