15520-05-5

Basic information

• Product Name: 2,2'-(octylimino)bisethanol
• Synonyms: 2,2'-(octylimino)bisethanol;bis-(2-hydroxy-ethyl)-octyl-amine;3-Octyl-3-azapentane-1,5-diol;Einecs 239-555-0;Ethanol, 2,2'-(octylimino)bis-;2,2'-(Octylazanediyl)diethanol;2,2-(OCTYLAZANEDIYL)BIS(ETHAN-1-OL)
• CAS NO: 15520-05-5
• Molecular Formula: C₁₂H₂₇NO₂
• Molecular Weight: 217.34828
• EINECS: 239-555-0
• Mol File: 15520-05-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 342.4°Cat760mmHg
• Flash Point: 150.5°C
• Appearance: /
• Density: 0.949g/cm³
• Vapor Pressure: 0.008Pa at 20℃
• Storage Temp.: 2-8°C
• PKA: 14.41±0.10(Predicted)
• Water Solubility: 1.4g/L at 20℃
• CAS DataBase Reference: 2,2'-(octylimino)bisethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-(octylimino)bisethanol(15520-05-5)
• EPA Substance Registry System: 2,2'-(octylimino)bisethanol(15520-05-5)

Safety Data

• Hazardous Substances Data: 15520-05-5(Hazardous Substances Data)

Usage

General Description

2,2'-(octylimino)bisethanol is a chemical compound with the molecular formula C18H37NO2. It is commonly referred to as octylimino-bisethanol and is used as a surfactant and emulsifier in various industrial and commercial applications. This chemical is a pale yellow viscous liquid with a mild odor and is soluble in water and organic solvents. It is commonly used in the production of cleaning products, personal care items, and in the formulation of emulsions and suspensions in the pharmaceutical and cosmetic industries. Additionally, it is also employed as a wetting agent in agricultural formulations and as a dispersant in the production of polymers and resins. However, potential health hazards associated with exposure to this chemical include skin and eye irritation, and it should be handled and disposed of according to proper safety protocols and regulations.

Synthetic route

1-bromo-octane (111-83-1) + 2,2'-iminobis[ethanol] (111-42-2) → n-octyl dihydroxyethyl tertiary amine (15520-05-5)

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Inert atmosphere; Reflux;	91%
In ethanol Heating; E. Wilson and M. Tishler, J. Am. Chem. Soc., 73, 3635 (1951);	78%
With potassium carbonate; potassium iodide In acetonitrile for 12h; Inert atmosphere; Reflux;	76.7%

1-Chlorooctane (111-85-3) + 2,2'-iminobis[ethanol] (111-42-2) → n-octyl dihydroxyethyl tertiary amine (15520-05-5)

Conditions	Yield
With sodium carbonate In acetonitrile for 9h; Heating;	65%
In isopropyl alcohol at 140℃;

oxirane (75-21-8) + n-Octylamine (111-86-4) → n-octyl dihydroxyethyl tertiary amine (15520-05-5)

Conditions	Yield
With water at 100 - 190℃;

2,2'-iminobis[ethanol] (111-42-2) + CH3(CH2)5CH2CH2X → n-octyl dihydroxyethyl tertiary amine (15520-05-5)

Conditions	Yield
With potassium carbonate In chloroform at 20℃;

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + C28H34O9S2 → N-octyl-8-benzyloxymethyl-4,7,10,13-tetraoxa-1-azacyclopentadecane

Conditions	Yield
With sodium t-butanolate In 1,4-dioxane; tert-butyl alcohol at 40℃; for 12h;	56%

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + diethylene glycol ditosylate (7460-82-4) → 10-octyl-1,4,7-trioxa-10-azacyclododecane (120547-32-2)

Conditions	Yield
With lithium; tert-butyl alcohol In 1,4-dioxane for 25h; Heating;	38%

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + iron(III) chloride (7705-08-0) → Fe6Cl6((OC2H4)2N(CH2)7CH3)6 (730959-69-0)

Conditions	Yield
With calcium hydride In tetrahydrofuran to a suspn. of CaH2 in anhydrous THF was added dihydroxyamine, stirred for 1 h at 20°C, a soln. of FeCl3 in anhydrous THF was added, the mixt. was stirred at 20°C for 72 h (N2); solvent was removed under vac., ppt. was dissolved in CH2Cl2, the residue was filtered off, evapd., recrystd. from CHCl3/n-pentane; elem. anal.;	18%

bis(o-phenylene)glycol ditosylate (54535-06-7) + n-octyl dihydroxyethyl tertiary amine (15520-05-5) → N-octylbenzoaza-15-crown-5

Conditions	Yield
With sodium hydride In tetrahydrofuran for 45h; Heating;	9%

n-octyl dihydroxyethyl tertiary amine (15520-05-5) → Bis-(2-chloro-ethyl)-octyl-amine (52419-79-1)

Conditions	Yield
With thionyl chloride In chloroform Heating;

n-octyl dihydroxyethyl tertiary amine (15520-05-5) → Bis-(2-chloro-ethyl)-octyl-amine; hydrochloride

Conditions	Yield
With thionyl chloride In chloroform E. Wilson and M. Tishler, J. Am. Chem. Soc., 73, 3635 (1951);
With thionyl chloride

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + benzyl chloride (100-44-7) → Octyldihydroxyethylbenzylammonium chloride (94816-71-4)

Conditions	Yield
In water at 60 - 65℃;

n-octyl dihydroxyethyl tertiary amine (15520-05-5) → C24H37N3S2

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: K2CO3; TBAHSO4 / dimethylformamide View Scheme

n-octyl dihydroxyethyl tertiary amine (15520-05-5) → N-n-Octyl-N'-(4-pentyloxyphenyl)-piperazine (129992-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / CHCl3 / E. Wilson and M. Tishler, J. Am. Chem. Soc., 73, 3635 (1951) 2: 2.) sodium carbonate / 1.) methanol, reflux, 6 h, 2.) reflux, 2-4 h View Scheme

oxirane (75-21-8) + methane sulfonic acid + n-octyl dihydroxyethyl tertiary amine (15520-05-5) → n-octyl tris(hydroxyethyl) ammonium methane sulfonate (129684-40-8)

Conditions	Yield
In water

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + N-Methylolacrylamid (924-42-5) → C16H31BN2O4 (1207858-70-5)

Conditions	Yield
Stage #1: n-octyl dihydroxyethyl tertiary amine With boric acid Stage #2: N-Methylolacrylamid

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + propargyl bromide (106-96-7) → C15H30NO2(1+)*Br(1-)

Conditions	Yield
In ethanol for 12h; Reflux;	7.36 g

n-octyl dihydroxyethyl tertiary amine (15520-05-5) + 1,3-dibromo-propane (109-64-8) → propanediyl-1,4-bis(octyl dihydroxyethyl ammonium bromide)

Conditions	Yield
for 48h; Reflux;

1,4-dibromo-butane (110-52-1) + n-octyl dihydroxyethyl tertiary amine (15520-05-5) → butanediyl-1,4-bis(octyl dihydroxyethyl ammonium bromide)

Conditions	Yield
for 48h; Reflux;

Upstream product

• 111-83-1 1-bromo-octane 
• 111-42-2 2,2'-iminobis[ethanol] 
• 111-85-3 n-chlorooctane 
• 75-21-8 oxirane 
• 111-86-4 n-Octylamine 

Downstream Products

• 94816-71-4 Octyldihydroxyethylbenzylammonium chloride 
• 129992-49-0 N-n-Octyl-N'-(4-pentyloxyphenyl)-piperazine 

Relevant articles and documents

Synthesis and Properties of Quaternary Ammonium Gemini Surfactants with Hydroxyethyl at Head Groups

A series of cationic gemini surfactants CmH2m + 1N+(CH2CH2OH)2?(CH2)s?N+(CH2CH2OH)2CmH2m + 1 2Br?, referred to as m-s-m (OH) (m = 8,10,12, s = 3,4), were prepared by quaternization of dihydroxyethyl tertiary amines with dibromoalkane. The dihydroxyethyl tertiary amines were synthesized by nucleophilic substitution of diethanolamine with bromoalkane. The characterization of the m-s-m (OH) surfactants was performed using 1H NMR and MS. The surface activities and aggregation behavior in aqueous solution of the m-s-m (OH) surfactants were studied using surface tension measurements, dynamic light scattering (DLS), and transmission electron microscopy (TEM). The surface tension and critical micellar concentration of these surfactants in aqueous solution decreased dramatically due to the introduction of hydroxyethyl at the head group. The micelles and/or vesicles formed in the aqueous solution of m-s-m (OH) surfactants were strongly dependent upon the lengths of spacer chains and carbon chains. The number of vesicles increases and that of micelles decreases when the lengths of spacer chains and carbon chains increase.

Alkynyl quaternary ammonium salt multifunctional surfactants and preparation method thereof

The invention discloses a series of alkynyl quaternary ammonium salt multifunctional surfactants and a preparation method thereof. A structural formula of quaternary ammonium salt is shown in the description, wherein R represents a C4-C22 linear, branched or cycloalkyl, aryl or alkenyl group. The preparation method comprises the following steps: (1) carrying out alkylation on ethanol amine under alkaline and acetonitrile reflux conditions by virtue of bromo-hydrocarbon; and (2) carrying out further alkylation on tertiary amine under an ethanol reflux condition by virtue of propargyl bromide, so as to obtain alkynyl quaternary ammonium salt, namely reddish brown semitransparent viscous liquid or solid. The alkynyl quaternary ammonium salt multifunctional surfactants have very high surface activity, good corrosion resistance and excellent viscoelasticity, the preparation method is simple and feasible, the raw material cost is low, the operation is easy, the yield is high, and the surfactants are environmentally friendly.

Substitution effect, absorption, and fluorescence behaviors of 11,12-benzo-1,7,10,13-tetraoxa-4-azacyclopentadec-11-ene (Benzoaza-15-crown-5) derivatives upon cation complexation in solvent extraction

Substitution effect, absorption, and fluorescence behaviors of some benzoaza-15-crown-5 derivatives upon cation complexation in solvent extraction were studied. The introduction of a substituent on the nitrogen atom in benzoaza-15-crown-5 enhanced extractabilities in the solvent extraction of aqueous alkali metal picrates. The nondonating substituents raised the cation selectivity for Na+ over K+, but the donating substituents reduced the cation selectivity. The absorption and fluorescence spectral behavior was different with the alkali metal cations.