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

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 111-42-2 2,2'-iminobis[ethanol] 
• 112-80-1 cis-Octadecenoic acid 

Downstream Products

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

Relevant articles and documents

METHOD FOR PREPARING FATTY ACID DIALKANOL AMIDES

The present invention relates to a method for manufacturing fatty acid dialkanol amides which comprises reaction of a fatty acid, diethanol amine, and a basic catalyst. An object of the present invention is to provide the method for manufacturing fatty acid dialkanol amides, which can be converted into fatty acid dialkanol amides in a high yield due to low production of by-products.

Cationic lipid molecule, and application thereof in nucleic acid delivery

The present invention discloses a cationic lipid molecule, and an application thereof in nucleic acid delivery. The structural formula of the cationic lipid molecule is represented by formula i. The invention further provides a cationic liposome, a lipid compound, a reagent, a kit, a preparation and a medicinal composition based on the cationic lipid molecule. The cationic lipid molecule has the advantages of simple synthesis process and good stability, and the cationic liposome has a high efficiency (characterized by high transfection efficiency) and a low toxicity, is stable and uniform, is easy to prepare, and can be used for transferring various cell lines. The cationic lipid molecule has excellent transitivity, and can efficiently deliver active substances (such as exemplary siRNA) omto cells (such as exemplary lung cancer cells), tissues and organs to achieve efficient regulation of the active substances. The problem that the toxicity and the transfer efficiency of cationic liposome existing in the prior art are low is solved.

Methods for production of fatty acid alkanolamides (FAAAs) from microalgae biomass

Provided herein are methods for fatty acid alkanolamide (FAAA) synthesis and isolation from lipid-containing algal biomass, and the products of such methods.

Low molecular weight PEI-based biodegradable lipopolymers as gene delivery vectors

Non-viral gene vectors play an important role in the development of gene therapy. In this report, different hydrophobic chains were introduced into low molecular weight (LMW) PEI-based biodegradable oligomers to form a series of lipopolymers (LPs), and their structure-activity relationships were studied. Results revealed that the nine polymers can condense plasmid DNA well to form nanoparticles with appropriate sizes (120-250 nm) and positive zeta-potentials (+25-40 V). In vitro experiments were carried out and it was found that LP2 showed much higher transfection efficiency both in the presence and in the absence of serum under the polymer/DNA weight ratio of 0.8 in A549 cells.

Nonionic diethanolamide amphiphiles with unsaturated C18 hydrocarbon chains: Thermotropic and lyotropic liquid crystalline phase behavior

The neat and lyotropic liquid crystalline phase behavior of three nonionic diethanolamide amphiphiles with C18 hydrocarbon chains containing one, two or three unsaturated bonds has been examined. This has allowed the effect of degree of unsaturation on the phase behavior of diethanolamide amphiphiles to be investigated. Neat linoleoyl and linolenoyl diethanolamide undergo a transition from a glassy liquid crystal to a liquid crystal at ～-85 °C, while neat oleoyl diethanolamide undergoes a transition at ～-60 °C to a liquid crystalline material before re-crystallizing at -34 °C. Oleoyl diethanolamide then undergoes a third transition from a crystalline phase to a smectic liquid crystalline phase at ～5 °C. In the absence of water, the transition temperature from a smectic liquid crystal to an isotropic liquid decreases with increasing unsaturation. The addition of water results in the formation of a lamellar phase (Lα) for all three amphiphiles. The lamellar phase is stable under excess water conditions up to temperatures of at least 70 °C. Approximate partial binary amphiphile-water phase diagrams generated for the three unsaturated C18 amphiphiles indicate that the excess water point for each amphiphile occurs at ～60% (w/w) amphiphile. the Owner Societies 2011.

BIODEGRADABLE CATIONIC POLYMERS

Polymers comprising a polyethylenimine having a molecular weight less than 600 Daltons, a biodegradable group, and a relatively hydrophobic group that are useful for the delivery of bioactive agents to cells.

Lipase-catalyzed synthesis of fatty acid diethanolamides.

Diethanolamides are nonionic emulsifiers widely used in industries such as cosmetics and as corrosion inhibitors. Candida antarctica lipase (Novozym 435) was used to catalyze the amidation of various fatty acids with diethanolamine. Contents of fatty acid

Use of N-acyl derivatives of aminoalcohols for the manufacture of a medicament for the treatment of pathologies involving mast cells

N-acyl-derivatives of amino alcohols suitable for the therapeutic treatment of pathologies characterized by degranulation of mast cells caused by a neurogen and/or immunogenic hyperstimulation.

Nitro-meta-phenylenediamines halogenated in the 6th position and their use in dyeing keratinic substances

The invention relates to compounds of formula STR1 in which X denotes a halogen atom, and R and R' denote a hydrogen atom, an alkyl, polyhydroxyalkyl, hydroxyalkoxyalkyl or alkoxyalkyl radical or an aminoalkyl radical optionally substituted on the nitrogen atom provided that at least one of the groups R and R' is a polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical, and to dye compositions for keratinic fibres in which they are employed, to the preparation process and to intermediates.

Nitrogen-containing products of phosphosulfurized amides and lubricants containing same

The invention herein is concerned with new compositions of matter made by (1) reacting phosphorus pentasulfide with an amide and (2) reacting this product with a nitrogen-containing compound, and lubricant compositions containing same. The compositions reduce friction to a greater extent than lubricants containing no additive and, when placed in lubricating oils and used in an internal combustion engine, fuel consumption is reduced.