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Oleic acid diethanolamide
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Name

Oleic acid diethanolamide

 EINECS 202-281-7
CAS No. 93-83-4 Density 0.96 g/cm3
PSA 60.77000 LogP 4.83710
Solubility N/A Melting Point -18oC
Formula C22H43NO3 Boiling Point 525.6 °C at 760 mmHg
Molecular Weight 369.588 Flash Point 271.7 °C
Transport Information N/A Appearance clear liquid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 93-83-4 (N,N-DIETHANOLOLEAMIDE) Hazard Symbols N/A
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;

Article Data 12

Oleic acid diethanolamide 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
ConditionsYield
In methanol; diethyl ether; water75%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In water at 95℃; for 1h; Inert atmosphere;

Oleic acid diethanolamide Consensus Reports

Reported in EPA TSCA Inventory.

Oleic acid diethanolamide Specification

The Oleic acid diethanolamide, with the CAS registry number 93-83-4 and EINECS registry number 202-281-7, has the systematic name of (9Z)-N,N-bis(2-hydroxyethyl)octadec-9-enamide. It is a kind of yellow transparent viscous liquid, and the molecular formula of this chemical is C22H43NO3.

The physical properties of Oleic acid diethanolamide are as following: (1)ACD/LogP: 6.61; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 4; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 21; (6)Polar Surface Area: 38.77 Å2; (7)Index of Refraction: 1.488; (8)Molar Refractivity: 110.85 cm3; (9)Molar Volume: 384.6 cm3; (10)Polarizability: 43.94×10-24cm3; (11)Surface Tension: 38.5 dyne/cm; (12)Density: 0.96 g/cm3; (13)Flash Point: 271.7 °C; (14)Enthalpy of Vaporization: 92.02 kJ/mol; (15)Boiling Point: 525.6 °C at 760 mmHg; (16)Vapour Pressure: 3.04E-13 mmHg at 25°C.

Preparation and uses of Oleic acid diethanolamide: It can be prepared by the condensation reaction of coconut fatty acid with diethanolameine. As a nonionic surfactant, it is often used as thickening agent in shampoo and antistatic agent. What's more, it can improve the stability of foam, and increase the detergency of shampoo.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N(CCO)CCO)CCCCCCC\C=C/CCCCCCCC
(2)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-
(3)InChIKey: LPMBTLLQQJBUOO-KTKRTIGZBW

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 10gm/kg (10000mg/kg)   Journal of the American College of Toxicology. Vol. 5(5), Pg. 415, 1986.
rat LD50 oral 12400uL/kg (12.4mL/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-481, Pg. 1999,

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