Diethanolamine oleate is a versatile chemical compound derived from oleic acid and diethanolamine, widely used as a surfactant and emulsifier in various industrial and commercial applications.

In the industrial sector, Diethanolamine oleate enhances the performance and stability of products such as paints, coatings, and adhesives by improving ingredient dispersion, ensuring a more homogeneous mixture.

In personal care products, Diethanolamine oleate acts as a key ingredient that helps blend oils and water effectively, resulting in a smooth, stable formulation and enhancing the quality of shampoos, lotions, and creams.

CAS Number: 111-42-2

EC Number: 203-868-0

Chemical formula: C4H11NO2

Molar mass: 105.137 g·mol−1

Synonyms: Diethanolamine oleate, OLEIC ACID DIETHANOLAMINE SALT, 13961-86-9, RF675SKV94, Oleic acid diethanolamine condensate (1:1), Diethanolamine compound with sulfurized oleic acid, 68130-87-0, 2-(2-hydroxyethylamino)ethanol;(Z)-octadec-9-enoic acid, 68855-44-7, Diethanolammonium oleate, Oleic acid, compound with 2,2'-iminodiethanol (1:1), 68439-43-0, CCRIS 4691, HSDB 4190, Oleic acid diethanolamine (1:1), NCI-C55334, EINECS 237-740-0, UNII-RF675SKV94, Ethanol, 2,2'-iminodi-, oleate (salt), Oleic acid, compound with diethanolamine (1:1), EINECS 272-485-9, Oleic acid, compd with 2,2'-iminodiethanol (1:1), Ethanol, 2,2'-imino-, (9Z)-9-octadecenoate (salt), Ethanol, 2,2'-iminobis-, (Z)-9-octadecenoate (salt), SCHEMBL242878, DTXSID9023831, KQHZEKNQJJSVDN-KVVVOXFISA-N, EINECS 270-404-1, OLEIC ACID, DIETHANOLAMINE SALT, NS00084646, Q27288086, (9Z)-9-Octadecenoic acid - 2,2′-iminodiethanol (1:1), (9Z)-9-Octadecensäure --2,2′-iminodiethanol (1:1), 13961-86-9, 237-740-0, 9-Octadecenoic acid, (9Z)-, compd. with 2,2′-iminobis[ethanol] (1:1), Acide (9Z)-9-octadécénoïque - 2,2′-iminodiéthanol (1:1), Diethanolamine oleate, RF675SKV94, (Z)-Octadec-9-enoic acid, 2-(2-Hydroxyethylamino)ethanol, 272-485-9, 9-Octadecenoic acid (9Z)-, compd. with 2,2′-iminobis(ethanol) (1:1), 9-Octadecenoic acid (Z)-, compd. with 2,2′-iminobis(ethanol) (1:1), 9-Octadecenoic acid(9Z)-, compd. with 2,2′-iminobis[ethanol] (1:1), Diethanolammonium oleate, EINECS 237-740-0, EINECS 272-485-9, Ethanol, 2,2′-imino-, (9Z)-9-octadecenoate (salt), Ethanol, 2,2′-iminobis-, (Z)-9-octadecenoate (salt), Ethanol, 2,2′-iminodi-, oleate (salt), Oleic acid diethanolamine, Oleic acid diethanolamine (1:1), Oleic acid diethanolamine condensate (1:1), Oleic acid diethanolamine salt, Oleic acid, compd with 2,2′-iminodiethanol (1:1), Oleic acid, compound with 2,2′-iminodiethanol (1:1), Oleic acid, compound with diethanolamine (1:1)

Diethanolamine oleate is a chemical compound derived from oleic acid and diethanolamine.

Diethanolamine oleate is commonly used as a surfactant and emulsifier in various industrial applications.

Diethanolamine oleate is clear golden-brown viscous liquid, that used as a surfactant and a corrosion inhibitor.

Diethanolamine oleate prolonged mean survival time of mice with Ehrlich exudative carcinoma.

The increase in mean survival time after administration of Diethanolamine oleate was 8.3%.

Diethanolamine oleate, chemical formula C22H43NO3, usually mixed in a ratio of 1:1.

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2.

Pure diethanolamine is a white solid at room temperature, but Diethanolamine oleate's tendencies to absorb water and to supercool often results in it being found in a colorless, viscous liquid state.

Diethanolamine is polyfunctional, being a secondary amine and a diol.

Like other organic amines, diethanolamine acts as a weak base.

Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, Diethanolamine oleate is soluble in water.

Amides prepared from Diethanolamine oleate are often also hydrophilic.

In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

Amine with alcohol and amine characteristics used in detergents, urethane foams, cement grinding aids, and in the manufacture of various amine compounds.

Building block in the manufacture of triazine based corrosion inhibitors.

Diethanolamine oleate is a nonionic surfactant derived from oleic acid and diethanolamine.

Diethanolamine oleate is widely used as an emulsifier, stabilizer, and surfactant in various industries such as personal care, textiles, paints, and more.

Diethanolamine oleate is a versatile chemical compound recognized for its effectiveness as a surfactant and emulsifier across a wide range of industrial and commercial applications.

Chemically, Diethanolamine oleate is a derivative of oleic acid and diethanolamine, combining these components to create a compound with superior emulsifying and stabilizing properties.

In the industrial sector, Diethanolamine oleate is commonly employed to enhance the performance and stability of products such as paints, coatings, and adhesives.

By improving the dispersion of ingredients, Diethanolamine oleate ensures a more homogeneous mixture, which is crucial for achieving consistent product quality.

In personal care products, including shampoos, lotions, and creams, Diethanolamine oleate acts as a key ingredient that helps to blend oils and water effectively, resulting in a smooth and stable formulation.

This emulsifying action also extends to Diethanolamine oleate's use in lubricants for metalworking, where it reduces friction and enhances the performance of machinery, thereby increasing tool life and productivity.

Furthermore, Diethanolamine oleate's role in detergents and cleaners is significant, as it facilitates the emulsification and removal of grease and oils, leading to more efficient cleaning processes.

Beyond these applications, Diethanolamine oleate is utilized in pharmaceutical formulations, where it assists in the emulsification of active ingredients.

In the agricultural sector, Diethanolamine oleate improves the distribution and effectiveness of pesticides and herbicides.

Additionally, in the textile industry, Diethanolamine oleate is used in dyeing and finishing processes to achieve better color uptake and fabric uniformity.

Diethanolamine oleate's broad range of uses highlights its importance as a functional ingredient in numerous products and processes.

Commonly used ingredients that may contain Diethanolamine oleate:

Diethanolamine oleate is used in the production of diethanolamides, which are common ingredients in cosmetics and shampoos added to confer a creamy texture and foaming action.

Consequently, some cosmetics that include diethanolamides as ingredients contain Diethanolamine oleate.

Some of the most commonly used diethanolamides include:

Cocamide DEA

DEA-Cetyl Phosphate

DEA Oleth-3 Phosphate

Lauramide DEA

Myristamide DEA

Oleamide DEA

Uses of Diethanolamine Oleate:

Diethanolamine oleate is widely used across several industries due to its effectiveness as a surfactant and emulsifier.

In industrial formulations, Diethanolamine oleate stabilizes and enhances the performance of products such as paints, coatings, and adhesives by improving ingredient dispersion.

Diethanolamine oleate's emulsifying properties are also valuable in personal care products, including shampoos, lotions, and creams, where it ensures a smooth, stable mixture of oils and water.

In the metalworking industry, Diethanolamine oleate is used in lubricants to reduce friction and improve machinery performance.

Diethanolamine oleate is incorporated into detergents and cleaners to aid in emulsifying and removing grease and oils, enhancing cleaning efficacy.

Additionally, Diethanolamine oleate finds applications in pharmaceuticals, agricultural products, and textile processing, demonstrating its versatility in various sectors.

Diethanolamine oleate is used as a surfactant and a corrosion inhibitor.

Diethanolamine oleate is used to remove hydrogen sulfide and carbon dioxide from natural gas.

Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos and hair conditioners.

In oil refineries, a Diethanolamine oleate in water solution is commonly used to remove hydrogen sulfide from sour gas.

Diethanolamine oleate has an advantage over a similar amine, ethanolamine, in that a higher concentration may be used for the same corrosion potential.

This allows refiners to scrub hydrogen sulfide at a lower circulating amine rate with less overall energy usage.

Diethanolamine oleate is a chemical feedstock used in the production of morpholine.

Amides derived from Diethanolamine oleate and fatty acids, known as diethanolamides, are amphiphilic.

The reaction of 2-chloro-4,5-diphenyloxazole with Diethanolamine oleate gave rise to ditazole.

The reaction of Diethanolamine oleate and isobutyraldehyde with water removed produces an oxazolidine.

Surfactant:

Diethanolamine oleate can be used as surfactants, making them widely used in detergents, emulsifiers and lubricants.

Cosmetics:

Due to its characteristics of adjustable viscosity and increased skin moisture, Diethanolamine oleate is also often used as an ingredient in cosmetics.

Pharmaceutical industry:

Diethanolamine oleate is used to prepare some pharmaceutical formulations.

Industry Uses:

Surfactant (surface active agent)

Paint additives and coating additives not described by other categories

Other Uses:

Gas sweetening

Detergents

Cleaners

Concrete admixtures

Urethane foam catalysts

Pharmaceuticals

Agricultural chemicals

Photographic emulsions

Applications of Diethanolamine Oleate:

Industrial cleaning field:

Diethanolamine oleate has excellent decontamination, emulsification, foaming, foam stabilization, dispersion, solubilization, antistatic, lubrication, anti-rust and anti-wear properties.

Household washing field:

Suitable for detergents in textile, chemical fiber, leather, personal care products and other fields.

Metal working fluid (oil) field:

Diethanolamine oleate can be used as lubricant, anti-rust agent, and anti-wear agent.

Resin, fiber and other fields:

Diethanolamine oleate can be used as lubricant and antistatic agent.

Other applications:

Diethanolamine oleate can be used as thickener, emulsifier, foaming agent, foam stabilizer, etc.

Benefits of Diethanolamine Oleate:

Unique reactions

Versatile

Broad spectrum of applications

Act as amines or alcohols

Nature of Diethanolamine Oleate:

Appearance:

Diethanolamine oleate is colorless to light yellow liquids.

Solubility:

Diethanolamine oleate can be dissolved in many organic solvents, such as ethanol, chloroform and benzene.

Density:

The density of Diethanolamine oleate is slightly higher than water.

Melting point and boiling point:

The specific value depends on the ratio and purity of the two compounds.

General Manufacturing Information of Diethanolamine Oleate:

Industry Processing Sectors:

Oil and Gas Drilling, Extraction, and Support activities

Paint and Coating Manufacturing

Preparation Method of Diethanolamine Oleate:

Diethanolamine oleate is generally prepared by mixing and reacting appropriate amounts of oleic acid and 2,2'-iminodiethanol.

The specific preparation depends on the purity and proportion of the desired product.

Production of Diethanolamine Oleate:

The reaction of ethylene oxide with aqueous ammonia first produces ethanolamine:

C2H4O + NH3 → H2NCH2CH2OH

which reacts with a second and third equivalent of ethylene oxide to give Diethanolamine oleate and triethanolamine:

C2H4O + H2NCH2CH2OH → HN(CH2CH2OH)2

C2H4O + HN(CH2CH2OH)2 → N(CH2CH2OH)3

About 300M kg are produced annually in this way.

The ratio of the products can be controlled by changing the stoichiometry of the reactants.

Handling and Storage of Diethanolamine Oleate:

Handling:

Use in a well-ventilated area to avoid inhalation of vapors.

Avoid contact with skin, eyes, and clothing.

Use appropriate personal protective equipment (PPE) such as gloves and safety goggles.

Handle with care to avoid spills and leaks.

Storage:

Store in a cool, dry place away from heat sources and direct sunlight.

Keep containers tightly closed and away from incompatible materials such as strong acids and oxidizing agents.

Stability and Reactivity of Diethanolamine Oleate:

Stability:

Diethanolamine oleate is generally stable under normal conditions.

Avoid exposure to high temperatures and open flames.

Reactivity:

Reacts with strong acids and oxidizing agents.

May decompose under extreme conditions, releasing hazardous fumes.

First Aid Measures of Diethanolamine Oleate:

Inhalation:

Move the affected person to fresh air immediately.

Seek medical attention if symptoms persist or if there is difficulty breathing.

Skin Contact:

Wash affected skin with plenty of soap and water.

Remove contaminated clothing.

Seek medical attention if irritation persists.

Eye Contact:

Rinse eyes immediately with plenty of water for at least 15 minutes, holding the eyelids open.

Seek medical attention if irritation persists.

Ingestion:

Rinse mouth with water.

Do not induce vomiting.

Seek medical attention immediately.

Firefighting Measures of Diethanolamine Oleate:

Fire Fighting:

Use foam, dry chemical, or carbon dioxide (CO2) to extinguish fires involving Diethanolamine oleate.

Water can be used to cool containers and prevent the spread of fire.

Wear self-contained breathing apparatus (SCBA) and full protective clothing when fighting fires.

Fire and Explosion Hazards:

Diethanolamine oleate may produce hazardous fumes such as carbon monoxide and carbon dioxide when burned.

Accidental Release Measures of Diethanolamine Oleate:

Personal Precautions:

Wear appropriate PPE, including gloves, goggles, and a respirator if needed.

Evacuate non-essential personnel from the area.

Environmental Precautions:

Prevent the chemical from entering drains, waterways, or soil.

Spill Cleanup:

Absorb spills with inert materials such as sand or vermiculite.

Collect the absorbed material in a suitable container for disposal.

Clean the area with soap and water.

Ensure proper disposal of waste in accordance with local regulations.

Exposure Controls/Personal Protective Equipment of Diethanolamine Oleate:

Exposure Limits:

Follow occupational exposure limits established by regulatory agencies.

Engineering Controls:

Ensure adequate ventilation in areas where Diethanolamine oleate is used.

Use local exhaust ventilation if necessary.

Personal Protective Equipment:

Skin Protection:

Wear chemical-resistant gloves and protective clothing.

Eye Protection:

Use safety goggles or face shields to protect against splashes.

Respiratory Protection:

Use a suitable respirator if ventilation is insufficient or if there is a risk of inhalation.

Hygiene Practices:

Wash hands and face thoroughly after handling.

Remove contaminated clothing and wash before reuse.

Identifiers of Diethanolamine Oleate:

Molecular formula: C22H45NO4

Average mass: 387.605

Monoisotopic mass: 387.334859

ChemSpider ID: 4938714

Catalog Number: ACMA00016919

Product Name: Diethanolamine oleate

Category: Polymers

Description: Oleic acid diethanolamine condensate (1/1) is a clear golden-brown viscous liquid. (NTP, 1992);Liquid

IUPAC Name: 2-(2-hydroxyethylamino)ethanol;(Z)-octadec-9-enoic acid

Molecular Weigh: t387.6g/mol

Molecular Formula: C22H45NO4

Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)O.C(CO)NCCO

InChI: InChI=1S/C18H34O2.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/h9-10H,2-8,11-17H2,1H3,(H,19,20);5-7H,1-4H2/b10-9-;

InChI Key: KQHZEKNQJJSVDN-KVVVOXFISA-N

Boiling Point: 469 to 473 °F at 760 mm Hg (NTP, 1992)

Flash Point: greater than 200 °F (NTP, 1992)

Solubility: less than 1 mg/mL at 77° F (NTP, 1992)

Complexity: 262

Covalently-Bonded Unit Count: 2

EC Number: 237-740-0;272-485-9;270-404-1

Exact Mass: 387.334859g/mol

Heavy Atom Count: 27

MeSH Entry Terms: Diethanolamine oleate

Monoisotopic Mass: 387.334859g/mol

Rotatable Bond Count: 19

UNI: IRF675SKV94

CAS Number: 111-42-2

3DMet: B01050

Beilstein Reference: 605315

ChEBI: CHEBI:28123

ChEMBL: ChEMBL119604

ChemSpider: 13835604

ECHA InfoCard: 100.003.517

EC Number: 203-868-0

KEGG: D02337

MeSH: diethanolaminePubChem CID: 8113

RTECS number: KL2975000

UNII: AZE05TDV2V

CompTox Dashboard (EPA): DTXSID3021932

Properties of Diethanolamine Oleate:

Chemical formula: C4H11NO2

Molar mass: 105.137 g·mol−1

Appearance: Colourless crystals

Odor: Ammonia odor

Density: 1.097 g·mL−1

Melting point: 28.00 °C; 82.40 °F; 301.15 K

Boiling point: 271.1 °C; 519.9 °F; 544.2 K

Solubility in water: Miscible

log P: -1.761

Vapor pressure: <1 Pa (at 20 °C)

UV-vis (λmax): 260 nm

Refractive index (nD): 1.477

Stereochemistry: ACHIRAL

Molecular Formula: C18H34O2.C4H11NO2

Molecular Weight: 387.597

Molecular Weight: 387.6 g/mol

Hydrogen Bond Donor Count: 4

Hydrogen Bond Acceptor Count: 5

Rotatable Bond Count: 19

Exact Mass: 387.33485892 g/mol

Monoisotopic Mass: 387.33485892 g/mol

Topological Polar Surface Area: 89.8Ų

Heavy Atom Count: 27

Complexity: 262

Isotope Atom Count: 0

Defined Atom Stereocenter Count: 0

Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 1

Undefined Bond Stereocenter Count: 0

Covalently-Bonded Unit Count: 2

Compound Is Canonicalized: Yes

Thermochemistry of Diethanolamine Oleate:

Heat capacity (C): 137 J·K−1·mol−1

Std enthalpy of formation (ΔfH⦵298): −496.4 – −491.2 kJ·mol−1

Std enthalpy of combustion (ΔcH⦵298): −26.548 – −26.498 MJ·kmol−1

Related compounds of Diethanolamine Oleate:

Diethylhydroxylamine

Related alkanols: 

N-Methylethanolamine

Dimethylethanolamine

Diethylethanolamine

N,N-Diisopropylaminoethanol

Methyl diethanolamine

Triethanolamine

Bis-tris methane

Meglumine

Names of Diethanolamine Oleate:

Preferred IUPAC name:

2,2′-Azanediyldi(ethan-1-ol)

Other names:

Bis(hydroxyethyl)amine

N,N-Bis(2-hydroxyethyl)amine

2,2'-Dihydroxydiethylamine

β,β'-Dihydroxydiethylamine

Diolamine

2-[(2-Hydroxyethyl)amino]ethanol

2,2'-Iminobisethanol

Iminodiethanol

Di(2-hydroxyethyl)amine

bis(2-Hydroxyethyl)amine

2,2'-Iminodiethanol