• Name

  N,N-DIETHANOLOLEAMIDE

• EINECS 202-281-7
• CAS No. 93-83-4
• Article Data12
• CAS DataBase
• Density 0.96 g/cm³
• Solubility
• Melting Point -18oC
• Formula C₂₂H₄₃NO₃
• Boiling Point 525.6 °C at 760 mmHg
• Molecular Weight 369.588
• Flash Point 271.7 °C
• Transport Information
• Appearance clear liquid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 9-Octadecenamide,N,N-bis(2-hydroxyethyl)-, (Z)-;Oleamide, N,N-bis(2-hydroxyethyl)-(6CI,7CI,8CI);Alkamide DO 280S;Alkamide DO-280;Alrosol O;Amisol ODE;Blaunon OL 05;Clindrol 200O;Clindrol 202O;Comperlan OD;Diethanolamine-oleicacid copolymer;Diethanololeamide;Emid 6545;Emulsifier WHC;Lauridit OD;Mackamide FTOA;Mackamide MO;Mackamide O;Marlamid D 1885;N,N-Bis(2-hydroxyethyl)oleamide;N,N-Diethanololeamide;Ninol 90201;NitreneNO;Oleamide DEA;Oleic diethanolamide;OleylamideDEA;Pamsurf;Romamid DT;Schercomid ODA;Stafoam DO;Stafoam DOS;Steinamid DO280SE;Varamide A 7;Vicamid 825;Witcamide 511C;Witcamide 511H;
• PSA 60.77000
• LogP 4.83710

Synthetic route

112-77-6

(Z)-9-octadecenoyl chloride

111-42-2

2,2'-iminobis[ethanol]

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

Conditions

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℃;

112-80-1

cis-Octadecenoic acid

111-42-2

2,2'-iminobis[ethanol]

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

Conditions

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%

112-80-1

cis-Octadecenoic acid

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

Conditions

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

111-42-2

2,2'-iminobis[ethanol]

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

Conditions

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

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

814-68-6

acryloyl chloride

883743-08-6

C28H47NO5

Conditions

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

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

1486-48-2

3,4,5-tribenzyloxybenzoic acid

N,N-bis[3,4,5-tris(benzyloxy)benzoyloxyethyl]oleoylamide

Conditions

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%

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

A

112-80-1

cis-Octadecenoic acid

B

111-42-2

2,2'-iminobis[ethanol]

Conditions

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

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

3282-30-2

pivaloyl chloride

63056-97-3

N,n-bis(2-trimethylacetoxyethyl)oleamide

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

106-89-8

epichlorohydrin

1421857-93-3

C28H51NO5

Conditions

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

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

69-72-7

salicylic acid

molybdenum(VI) oxide

2C22H41NO3(2-)*2C7H5O3(1-)*Mo(6+)

Conditions

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

...Expand

N-lauroyl-N-methyl-beta-alanine

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

oleic acid diethanolamide-O,O'-bis(N-lauroyl-N-methyl-beta-alanine)ester

Conditions

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

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

1486-48-2

3,4,5-tribenzyloxybenzoic acid

N,N-bis(3,4,5-trihydroxybenzoyloxyethyl)octadecanoylamide

Conditions

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

89583-07-3

N-(2-bromoethyl)morpholine

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

C34H65N3O5

Conditions

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;

89583-07-3

N-(2-bromoethyl)morpholine

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

C34H67N3O5

Conditions

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

586-95-8

pyridine-4-methanol

93-83-4

N,N-bis(2-hydroxyethyl)-oleamide

C34H53N3O3

Conditions

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;

Oleic acid diethanolamide Consensus Reports

Oleic acid diethanolamide Specification