93-82-3

Basic information

• Product Name: N,N-bis(2-hydroxyethyl)stearamide
• Synonyms: N,N-bis(2-hydroxyethyl)stearamide;STEARAMIDE DEA;Octadecanamide, N,N-bis(2-hydroxyethyl)-;N,N-Bis(2-hydroxyethyl)stearamid;N,N-BIS(2-HYDROXYETHYL)OCTADECANAMIDE);stearic diethanolamide;N,N-Bis(2-hydroxyethyl)stearic amide;Diethanolamine stearic acid amide
• CAS NO: 93-82-3
• Molecular Formula: C₂₂H₄₅NO₃
• Molecular Weight: 371.5976
• EINECS: 202-280-1
• Product Categories: Home Care
• Mol File: 93-82-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 516.3 °C at 760 mmHg
• Flash Point: 266 °C
• Appearance: /
• Density: 0.95 g/cm³
• Vapor Pressure: 8.98E-16mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.13±0.10(Predicted)
• CAS DataBase Reference: N,N-bis(2-hydroxyethyl)stearamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-bis(2-hydroxyethyl)stearamide(93-82-3)
• EPA Substance Registry System: N,N-bis(2-hydroxyethyl)stearamide(93-82-3)

Safety Data

• Hazardous Substances Data: 93-82-3(Hazardous Substances Data)

Usage

Uses

stearamide DEA (stearic acid diethanolamide) is a thickener and a wax emulsifier used in soaps, creams, and lotions.

InChI:InChI=1/C18H37NO.C4H11NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;6-3-1-5-2-4-7/h2-17H2,1H3,(H2,19,20);5-7H,1-4H2

Synthetic route

Methyl stearate (112-61-8) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(2-hydroxyethyl)stearamide (93-82-3)

Conditions	Yield
With sodium hydroxide at 110℃; for 5h;	82.58%

2,2'-iminobis[ethanol] (111-42-2) + stearic acid (57-11-4) → N,N-bis(2-hydroxyethyl)stearamide (93-82-3)

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 50℃; for 24h; Kinetics;
Stage #1: 2,2'-iminobis[ethanol]; stearic acid With benzotriazol-1-ol; triethylamine In dichloromethane for 0.25h; Cooling with ice; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice;
Stage #1: 2,2'-iminobis[ethanol]; stearic acid at 145℃; for 5h; Inert atmosphere; Stage #2: With sodium methylate at 80℃; for 3h; Temperature; Inert atmosphere;

2,2'-iminobis[ethanol] (111-42-2) + Stearoyl chloride (112-76-5) → N,N-bis(2-hydroxyethyl)stearamide (93-82-3)

Conditions	Yield
With tert.-butylhydroperoxide; ammonia In dichloromethane at -5℃; pH=10;

stearic acid (57-11-4) → N,N-bis(2-hydroxyethyl)stearamide (93-82-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: caprolactam; thionyl chloride / ethanol / -5 °C 2: ammonia; tert.-butylhydroperoxide / dichloromethane / -5 °C / pH 10 View Scheme

1,3-propanesultone (1120-71-4) + N,N-bis(2-hydroxyethyl)stearamide (93-82-3) → C28H55NO9S2(2-)*2Na(1+)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 16h; Reflux;	56.12%

N,N-bis(2-hydroxyethyl)stearamide (93-82-3) → 2,2'-iminobis[ethanol] (111-42-2) + stearic acid (57-11-4)

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

oxirane (75-21-8) + N,N-bis(2-hydroxyethyl)stearamide (93-82-3) → stearyl diethanolamide18EO adduct

Conditions	Yield
Stage #1: N,N-bis(2-hydroxyethyl)stearamide; sodium hydroxide; tetramethyl ammoniumhydroxide In water at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane In water at 80 - 90℃; for 3h; Product distribution / selectivity;
Stage #1: N,N-bis(2-hydroxyethyl)stearamide; sodium methylate at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane at 80 - 90℃; for 3h; Product distribution / selectivity;

N,N-bis(2-hydroxyethyl)stearamide (93-82-3) + epichlorohydrin (106-89-8) → C28H53NO5 (1421857-92-2)

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

N,N-bis(2-hydroxyethyl)stearamide (93-82-3) + molybdenum(VI) oxide → C22H43MoNO5

Conditions	Yield
In toluene at 110℃; Inert atmosphere;

Upstream product

• 57-11-4 stearic acid 
• 111-42-2 2,2'-iminobis[ethanol] 
• 112-76-5 Stearoyl chloride 
• 112-61-8 Methyl stearate 

Downstream Products

• 111-42-2 2,2'-iminobis[ethanol] 
• 57-11-4 stearic acid 

Relevant articles and documents

Synthetic method of coconut diethanol amide

The invention particularly relates to a synthetic method of coconut diethanol amide. The synthetic method comprises the following steps that 1, raw materials fatty acid and diethanol amine (DEA) are pretreated and purified; 2, under N2 airflow protection, and the fatty acid and the diethanol amine (DEA) perform amidate and ammonolysis reaction; 3, finally adsorption treatment is performed by using activated carbon, and filtration is performed to obtain the coconut diethanol amide. The 1: 1 coconut diethanol amide prepared by adopting the method has the advantages of being high in purity, light in color and luster, light in smell, low in amine value and the like.

Sulfonate type biomass surface active agent and synthetic method

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