93-83-4

Basic information

• Product Name: N,N-DIETHANOLOLEAMIDE
• Synonyms: N,N-DIETHANOLOLEAMIDE;OLEIC DIETHANOLAMIDE;OLEIC ACID DIETHANOLAMIDE;(9Z)-N,N-Bis(2-hydroxyethyl)-9-octadecenamide;(z)-n,n-bis(2-hydroxyethyl)-9-octadecenamide;9-Octadecenamide, N,N-bis(2-hydroxyethyl)-, (Z)-;Alkamide DO-280;Alkamide WRS 1-66
• CAS NO: 93-83-4
• Molecular Formula: C₂₂H₄₃NO₃
• Molecular Weight: 369.58
• EINECS: 202-281-7
• Mol File: 93-83-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 525.6 °C at 760 mmHg
• Flash Point: 271.7 °C
• Appearance: /
• Density: 0.96 g/cm³
• Vapor Pressure: 3.04E-13mmHg at 25°C
• Refractive Index: 1.488
• PKA: 14.13±0.10(Predicted)
• CAS DataBase Reference: N,N-DIETHANOLOLEAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHANOLOLEAMIDE(93-83-4)
• EPA Substance Registry System: N,N-DIETHANOLOLEAMIDE(93-83-4)

Safety Data

• Hazardous Substances Data: 93-83-4(Hazardous Substances Data)

Usage

Safety Profile

A poison by ingestion. Amoderate skin irritant. When heated to decomposition itemits toxic vapors of NOx.

InChI:InChI=1/C22H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(26)23(18-20-24)19-21-25/h9-10,24-25H,2-8,11-21H2,1H3/b10-9+

Synthetic route

(Z)-9-octadecenoyl chloride (112-77-6) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(2-hydroxyethyl)-oleamide (93-83-4)

Conditions	Yield
In methanol; diethyl ether; water	75%
In dichloromethane at -40 - -10℃; Inert atmosphere;	75.5%
With dmap; triethylamine In dichloromethane at 0 - 20℃;

cis-Octadecenoic acid (112-80-1) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(2-hydroxyethyl)-oleamide (93-83-4)

Conditions	Yield
Stage #1: cis-Octadecenoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: 2,2'-iminobis[ethanol] In dichloromethane at 20℃; for 18h;	58.2%
With Candida antarctica lipase In acetonitrile at 60℃; for 24h;	23%
With Candida antarctica lipase In acetonitrile at 50℃; for 24h; Kinetics;	12.1%

cis-Octadecenoic acid (112-80-1) → N,N-bis(2-hydroxyethyl)-oleamide (93-83-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 21 °C / Inert atmosphere 2: dichloromethane / -40 - -10 °C / Inert atmosphere View Scheme

C40H75NO4 + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(2-hydroxyethyl)-oleamide (93-83-4)

Conditions	Yield
With potassium hydroxide at 160℃; for 4h; Temperature;

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) + acryloyl chloride (814-68-6) → C28H47NO5 (883743-08-6)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	81%

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) + 3,4,5-tribenzyloxybenzoic acid (1486-48-2) → N,N-bis[3,4,5-tris(benzyloxy)benzoyloxyethyl]oleoylamide

Conditions	Yield
Stage #1: 3,4,5-tribenzyloxybenzoic acid With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Stage #2: N,N-bis(2-hydroxyethyl)-oleamide In dichloromethane at 20℃;	66%

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) → cis-Octadecenoic acid (112-80-1) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 50℃; for 24h; Kinetics;

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) + pivaloyl chloride (3282-30-2) → N,n-bis(2-trimethylacetoxyethyl)oleamide (63056-97-3)

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) + epichlorohydrin (106-89-8) → C28H51NO5 (1421857-93-3)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In water at 0 - 20℃; for 12.5h;

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) + salicylic acid (69-72-7) + molybdenum(VI) oxide → 2C22H41NO3(2-)*2C7H5O3(1-)*Mo(6+)

Conditions	Yield
In water at 95℃; for 1h; Inert atmosphere;

N-lauroyl-N-methyl-beta-alanine + N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) → oleic acid diethanolamide-O,O'-bis(N-lauroyl-N-methyl-beta-alanine)ester

Conditions	Yield
at 120℃; under 15.0015 Torr; for 7h;	905 g

N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) + 3,4,5-tribenzyloxybenzoic acid (1486-48-2) → N,N-bis(3,4,5-trihydroxybenzoyloxyethyl)octadecanoylamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dmap / dichloromethane / 0.5 h / 20 °C 1.2: 20 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 30 °C View Scheme

N-(2-bromoethyl)morpholine (89583-07-3) + N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) → C34H65N3O5

Conditions	Yield
Stage #1: N,N-bis(2-hydroxyethyl)-oleamide With sodium hydride In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: N-(2-bromoethyl)morpholine In tetrahydrofuran at 60℃; for 16h; Inert atmosphere;

N-(2-bromoethyl)morpholine (89583-07-3) + N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) → C34H67N3O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 60 °C / Inert atmosphere 1.2: 16 h / 60 °C / Inert atmosphere 2.1: hydrogen; palladium on activated charcoal / methanol / 18 h / 20 °C View Scheme

pyridine-4-methanol (586-95-8) + N,N-bis(2-hydroxyethyl)-oleamide (93-83-4) → C34H53N3O3

Conditions	Yield
Stage #1: pyridine-4-methanol With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: N,N-bis(2-hydroxyethyl)-oleamide With sodium hydride In tetrahydrofuran at 0 - 60℃; Inert atmosphere;

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 111-42-2 2,2'-iminobis[ethanol] 
• 112-77-6 (Z)-9-octadecenoyl chloride 

Downstream Products

• 63056-97-3 N,n-bis(2-trimethylacetoxyethyl)oleamide 
• 112-80-1 cis-Octadecenoic acid 
• 111-42-2 2,2'-iminobis[ethanol] 

Relevant articles and documents

METHOD FOR PREPARING FATTY ACID DIALKANOL AMIDES

The present invention relates to a method for manufacturing fatty acid dialkanol amides which comprises reaction of a fatty acid, diethanol amine, and a basic catalyst. An object of the present invention is to provide the method for manufacturing fatty acid dialkanol amides, which can be converted into fatty acid dialkanol amides in a high yield due to low production of by-products.

Methods for production of fatty acid alkanolamides (FAAAs) from microalgae biomass

Provided herein are methods for fatty acid alkanolamide (FAAA) synthesis and isolation from lipid-containing algal biomass, and the products of such methods.

Nonionic diethanolamide amphiphiles with unsaturated C18 hydrocarbon chains: Thermotropic and lyotropic liquid crystalline phase behavior

The neat and lyotropic liquid crystalline phase behavior of three nonionic diethanolamide amphiphiles with C18 hydrocarbon chains containing one, two or three unsaturated bonds has been examined. This has allowed the effect of degree of unsaturation on the phase behavior of diethanolamide amphiphiles to be investigated. Neat linoleoyl and linolenoyl diethanolamide undergo a transition from a glassy liquid crystal to a liquid crystal at ～-85 °C, while neat oleoyl diethanolamide undergoes a transition at ～-60 °C to a liquid crystalline material before re-crystallizing at -34 °C. Oleoyl diethanolamide then undergoes a third transition from a crystalline phase to a smectic liquid crystalline phase at ～5 °C. In the absence of water, the transition temperature from a smectic liquid crystal to an isotropic liquid decreases with increasing unsaturation. The addition of water results in the formation of a lamellar phase (Lα) for all three amphiphiles. The lamellar phase is stable under excess water conditions up to temperatures of at least 70 °C. Approximate partial binary amphiphile-water phase diagrams generated for the three unsaturated C18 amphiphiles indicate that the excess water point for each amphiphile occurs at ～60% (w/w) amphiphile. the Owner Societies 2011.