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

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

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

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