110-30-5

Basic information

• Product Name: N,N'-Ethylenebis(stearamide)
• Synonyms: N,N'-ETHYLENEBISSTEARAMIDE;N,N'-ETHYLENEBISOCTADECANAMIDE;1,2-bis(octadecanamido)ethane;abrilwax10ds;acrawaxc;acrawaxct;acrowaxc;advawachs280
• CAS NO: 110-30-5
• Molecular Formula: C₃₈H₇₆N₂O₂
• Molecular Weight: 593.02
• EINECS: 203-755-6
• Product Categories: Intermediates & Fine Chemicals;Isotope Labeled Compounds;Neurochemicals;Pharmaceuticals;Engineering Polymers;Polymer Science;Waxes and Oils
• Mol File: 110-30-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 144-146 °C(lit.)
• Boiling Point: 646.41°C (rough estimate)
• Flash Point: 280℃
• Appearance: /beads
• Density: 1 g/cm3 (20℃)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4670 (estimate)
• Storage Temp.: Storage temperature: no restrictions.
• Solubility: ketones, alcohols and aromatic solvents at their boiling points:
• PKA: 15.53±0.46(Predicted)
• Water Solubility: 0ng/L at 25℃
• CAS DataBase Reference: N,N'-Ethylenebis(stearamide)(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Ethylenebis(stearamide)(110-30-5)
• EPA Substance Registry System: N,N'-Ethylenebis(stearamide)(110-30-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 110-30-5(Hazardous Substances Data)

Usage

Description

N,N'-Ethylenebis(stearamide), also known as Ethylene Bis Stearamide (EBS), is a synthetic wax with fatty amide groups that can interact with the surface of various nanoparticles. It is an oily liquid that serves as a bis-amide polymer additive, offering a wide range of applications such as lubricants, activators, and dispersing agents to reduce friction and increase processing rates.

Uses

Used in Asphalt Industry:
N,N'-Ethylenebis(stearamide) is used as a Glyco Asphalt Modifier for lowering the temperature at which the asphalt softens, improving its workability and performance.
Used in Resin and Polymer Industry:
N,N'-Ethylenebis(stearamide) is used as a processing aid for resins and polymers, enhancing their processability and performance. It is also used as a defoaming agent to control foam formation during processing.
Used in Powdered Metal Industry:
Acrawax(R) C, a form of N,N'-Ethylenebis(stearamide), is traditionally used as a lubricant and binder for cold compaction of powdered metal parts, improving the efficiency and quality of the compaction process.
Used in Polymer Processing:
Acrawax(R) C, in its atomized, beaded, and prilled forms, is used as a processing aid, defoaming agent, lubricant, slip additive, and pigment dispersant aid for most polymers, enhancing their processing and performance characteristics.
Used in Paper Pulp and Textile Industry:
Glycowax(R) 765, an ethylenebisstearamide specifically developed for low and consistent viscosities, is used as a defoamer in paper pulp and textile processing, improving the efficiency and quality of these processes.

InChI:InChI=1/C38H76N2O2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(37(39)41)33-34-36(38(40)42)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36H,3-34H2,1-2H3,(H2,39,41)(H2,40,42)

Synthetic route

ethylenediamine (107-15-3) + stearic acid (57-11-4) → N-(2-octadecanamidoethyl)octadecanamide (110-30-5)

Conditions	Yield
Stage #1: stearic acid at 100℃; for 0.166667h; Inert atmosphere; Stage #2: ethylenediamine for 6h; Temperature; Reagent/catalyst; Inert atmosphere;	94.3%

N-(2-aminoethyl)octadecanamide (871-79-4) + Stearoyl chloride (112-76-5) → N-(2-octadecanamidoethyl)octadecanamide (110-30-5)

Conditions	Yield
Stage #1: N-(2-aminoethyl)octadecanamide; Stearoyl chloride In N,N-dimethyl-formamide at 5 - 20℃; for 11h; Stage #2: In N,N-dimethyl-formamide	95%

stearic acid (57-11-4) → N-(2-octadecanamidoethyl)octadecanamide (110-30-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride 2.1: pyridine / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 11 h / 5 - 20 °C 3.1: N,N-dimethyl-formamide / 11 h / 5 - 20 °C View Scheme

Stearoyl chloride (112-76-5) → N-(2-octadecanamidoethyl)octadecanamide (110-30-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 11 h / 5 - 20 °C 2.1: N,N-dimethyl-formamide / 11 h / 5 - 20 °C View Scheme

1,2-ethanediamine monohydrate (6780-13-8) + stearic acid (57-11-4) → N-(2-aminoethyl)octadecanamide (871-79-4) + N-(2-octadecanamidoethyl)octadecanamide (110-30-5)

Conditions	Yield
at 200℃;

N-(2-octadecanamidoethyl)octadecanamide (110-30-5) + ethylenediamine (107-15-3) → 2-heptadecyl-2-imidazoline (105-28-2)

Conditions	Yield
With phenyl diamidophosphate 1.) 235-250 deg C, 8 min, 2.) 80 deg C, 20 min; Yield given. Multistep reaction;

N-(2-octadecanamidoethyl)octadecanamide (110-30-5) + Trimethylenediamine (109-76-2) → 2-heptadecyl-1,4,5,6-tetrahydropyrimidine (88097-26-1)

Conditions	Yield
With phenyl diamidophosphate 1.) 235-250 deg C, 8 min, 2.) reflux, 10 min; Yield given. Multistep reaction;

N-(2-octadecanamidoethyl)octadecanamide (110-30-5) → 2-heptadecyl-2-imidazoline (105-28-2) + N-butyl-stearoyl amide (4219-50-5)

Conditions	Yield
With N-butylamine; phenyl diamidophosphate 1.) 235-250 deg C, 8 min, 2.) reflux, 5-10 min; Yield given. Multistep reaction. Yields of byproduct given;

N-(2-octadecanamidoethyl)octadecanamide (110-30-5) + N-butylamine (109-73-9) → 2-heptadecyl-2-imidazoline (105-28-2) + N-butyl-stearoyl amide (4219-50-5)

Conditions	Yield
With phenyl diamidophosphate 1.) 235-250 deg C, 8 min, 2.) reflux, 5-10 min; Yield given. Multistep reaction. Yields of byproduct given;

Upstream product

• 112-76-5 Stearoyl chloride 
• 57-11-4 stearic acid 
• 871-79-4 N-(2-aminoethyl)octadecanamide 
• 107-15-3 ethylenediamine 
• 6780-13-8 1,2-ethanediamine monohydrate 

Downstream Products

• 105-28-2 2-heptadecyl-2-imidazoline 
• 4219-50-5 N-butyl-stearoyl amide 

Relevant articles and documents

Fabrication of nanotubules and microspheres from the self-assembly of amphiphilic monochain stearic acid derivatives

A series of amphiphilic monochain derivatives of stearic acid, CH 3(CH2)16CONH(CH2)nNH 2 (n = 2, 3, 4, 6), CH3(CH2) 16CONH(CH2)2S2(CH2) 2NH2, and [CH3(CH2) 16CONH]2(CH2)2, are synthesized, and their self-assembly behaviors have been investigated in 1,2-dichloroethane (DCE). In addition to the concentration of the compound in DCE, the number of methylene units in hydrophilic segments play a crucial role in determining the final morphology of self-assembling structures from nanotubules with 20 nm inner diameter to microspheres with an average diameter of 20 μm. The external texture of the microsphere is also influenced by the number of methylene units in the hydrophilic segment. The microspheres formed by highly ordered aggregattion of nanobelts show high thermal stability. The particular processes and causations have been expatiated.

Method for synthesizing ethylene bisstearamide under catalysis of phosphotungstic acid quaternary ammonium titanium salt

The invention relates to a method for synthesizing ethylene bisstearamide under the catalysis of a phosphotungstic acid quaternary ammonium titanium salt. The method is characterized in that the ethylene bisstearamide is synthesized from stearic acid and ethylenediamine under the catalysis of the phosphotungstic acid quaternary ammonium titanium salt used as a catalyst, and the structural formulaof the phosphotungstic acid quaternary ammonium titanium salt is shown in the description; and in the formula, R is -C16H33, x = 0.4-0.6, and y = 0.4-0.6. The molecular structure of the phosphotungstic acid quaternary ammonium titanium salt catalyst contains lipophilic groups, so the catalyst has the advantages of good affinity to the raw material stearic acid, high specific surface area, suitableacid intensity, high surface acid amount, and excellent catalytic performance on the ethylene bisstearamide synthesis reaction, and the product has the advantages of high yield, light color and highpurity.

Method for catalytic synthesis of ethylene bis stearamide with phosphotungstate

The invention relates to a method for catalytic synthesis of ethylene bis stearamide with a phosphotungstate. The method is characterized in that the phosphotungstate is used as a catalyst to catalyzestearic acid and ethylenediamine to synthesize ethylene bis stearamide, the structural formula of the phosphotungstate is (NH)TiHPWO, x= 0.4-0.6, and y=0.4-0.6. The phosphotungstate catalyst provided by the invention has the advantages of relatively high specific surface area, proper acid strength, relatively high surface acid amount, excellent catalytic performance on the reaction for synthesizing ethylene bis stearamide; and an obtained product is high in yield, light in color and luster, and high in purity.