N-Oleyl-1,3-propanediamine

Last updated
N-Oleyl-1,3-propanediamine
N-Oleyl-1,3-propanediamine.svg
Names
Preferred IUPAC name
N1-[(9Z)-Octadec-9-en-1-yl]propane-1,3-diamine
Other names
(Z)-N-9-octadecenylpropane-1,3-diamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.754 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C21H44N2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-23-21-18-19-22/h9-10,23H,2-8,11-22H2,1H3/b10-9-
    Key: TUFJPPAQOXUHRI-KTKRTIGZSA-N
  • CCCCCCCC/C=C\CCCCCCCCNCCCN
Properties
C21H44N2
Molar mass 324.597 g·mol−1
AppearanceColourless or yellow liquid
Odor Ammoniacal
Density 0.841 g/cm3
Melting point 12 °C (54 °F; 285 K)
Boiling point 300 °C (572 °F; 573 K)
insoluble (at 20 °C)
Solubility Soluble in acetone, methanol
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H290, H301, H302, H315, H318, H372, H410
P234, P260, P264, P270, P273, P280, P301+P330+P331, P302+P352, P304+P340, P321, P330, P362+P364, P363, P390, P391, P405, P406, P501
NFPA 704 (fire diamond)
3
1
0
Flash point 54 °C (129 °F; 327 K)
Safety data sheet (SDS) [1]
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Oleyl-1,3-propanediamine is an organic compound and a diamine with the formula C21H44N2. [2] [3] It has found use in numerous industries. The main producer of commercial N-Oleyl-1,3-propanediamine is AkzoNobel, who sells it under the name Duomeen OL. [4]

Uses

N-Oleyl-1,3-propanediamine is used as a catalyst in the production of urethanes and epoxies. It is used as a emulsifier in the making of asphalt, an ore flotation agent, and a dispersant for some paints. It has also found use as a lubricant due to its unreactivity with cations, which are present in some adhesive manufacturing.

Related Research Articles

<span class="mw-page-title-main">Imperial Chemical Industries</span> Former British chemicals, paints and pharmaceuticals company

Imperial Chemical Industries (ICI) was a British chemical company. It was, for much of its history, the largest manufacturer in Britain. It was formed by the merger of four leading British chemical companies in 1926. Its headquarters were at Millbank in London. ICI was a constituent of the FT 30 and later the FTSE 100 indices.

<span class="mw-page-title-main">William Lipscomb</span> American chemist (1919–2011)

William Nunn Lipscomb Jr. was a Nobel Prize-winning American inorganic and organic chemist working in nuclear magnetic resonance, theoretical chemistry, boron chemistry, and biochemistry.

<span class="mw-page-title-main">Rayon</span> Cellulose-based semi-synthetic fiber

Rayon is a semi-synthetic fiber, made from natural sources of regenerated cellulose, such as wood and related agricultural products. It has the same molecular structure as cellulose. It is also called viscose. Many types and grades of viscose fibers and films exist. Some imitate the feel and texture of natural fibers such as silk, wool, cotton, and linen. The types that resemble silk are often called artificial silk.

Twaron is a para-aramid. It is a heat-resistant and strong synthetic fibre developed in the early 1970s by the Dutch company Akzo Nobel's division Enka BV, later Akzo Industrial Fibers. The research name of the para-aramid fibre was originally Fiber X, but it was soon called Arenka. Although the Dutch para-aramid fiber was developed only a little later than DuPont's Kevlar, the introduction of Twaron as a commercial product came much later than Kevlar due to financial problems at the AKZO company in the 1970s.

<span class="mw-page-title-main">AkzoNobel</span> Dutch multinational company which creates paints and performance coating

Akzo Nobel N.V., stylized as AkzoNobel, is a Dutch multinational company which creates paints and performance coatings for both industry and consumers worldwide. Headquartered in Amsterdam, the company has activities in more than 80 countries, and employs over 32,000 people. Sales in 2020 were €8.5 billion.

<span class="mw-page-title-main">Schiff base</span> Organic compound containing the group >C=N–

In organic chemistry, a Schiff base is a compound with the general structure R1R2C=NR3. They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimines depending on their structure. The term is often synonymous with azomethine which refers specifically to secondary aldimines.

<span class="mw-page-title-main">PPG Industries</span> Global supplier of glass and chemical products

PPG Industries, Inc. is an American Fortune 500 company and global supplier of paints, coatings, and specialty materials. With headquarters in Pittsburgh, Pennsylvania, PPG operates in more than 70 countries around the globe. By revenue it is the largest coatings company in the world followed by AkzoNobel. It is headquartered in PPG Place, an office and retail complex in downtown Pittsburgh, and is known for its glass facade designed by Postmodern architect Philip Johnson.

<span class="mw-page-title-main">Safranin</span> Chemical compound

Safranin is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospore staining. It can also be used for the detection of cartilage, mucin and mast cell granules.

<span class="mw-page-title-main">Cucurbituril</span>

Cucurbiturils are macrocyclic molecules made of glycoluril monomers linked by methylene bridges. The oxygen atoms are located along the edges of the band and are tilted inwards, forming a partly enclosed cavity. The name is derived from the resemblance of this molecule with a pumpkin of the family of Cucurbitaceae.

<span class="mw-page-title-main">Henry reaction</span>

The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-nitro alcohols. This type of reaction is also referred to as a nitroaldol reaction. It is nearly analogous to the aldol reaction that had been discovered 23 years prior that couples two carbonyl compounds to form β-hydroxy carbonyl compounds known as "aldols". The Henry reaction is a useful technique in the area of organic chemistry due to the synthetic utility of its corresponding products, as they can be easily converted to other useful synthetic intermediates. These conversions include subsequent dehydration to yield nitroalkenes, oxidation of the secondary alcohol to yield α-nitro ketones, or reduction of the nitro group to yield β-amino alcohols.

<span class="mw-page-title-main">Diisobutylaluminium hydride</span> Chemical compound

Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). This organoaluminium compound is a reagent in organic synthesis.

Trypan blue is an azo dye. It is a direct dye for cotton textiles. In biosciences, it is used as a vital stain to selectively colour dead tissues or cells blue.

A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term diamine refers mostly to primary diamines, as those are the most reactive.

In chemistry, the Noyori asymmetric hydrogenation refers to methodology for enantioselective reduction of ketones and related functional groups. This methodology was introduced by Ryoji Noyori, who shared the Nobel Prize in Chemistry in 2001 for contributions to asymmetric hydrogenation. These hydrogenations are used in the production of several drugs, such as the antibacterial levofloxin, the antibiotic carbapenem, and the antipsychotic agent BMS181100.

Organon & Co. is an American pharmaceutical company headquartered in Jersey City, New Jersey. Organon specializes in the following core therapeutic fields: reproductive medicine, contraception, psychiatry, hormone replacement therapy (HRT), and anesthesia. Organon sells to international markets.

<span class="mw-page-title-main">Hexamethylenediamine</span> Chemical compound

Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.

<span class="mw-page-title-main">Jacobsen's catalyst</span> Chemical compound

Jacobsen's catalyst is the common name for N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane­diaminomanganese(III) chloride, a coordination compound of manganese and a salen-type ligand. It is used as an asymmetric catalyst in the Jacobsen epoxidation, which is renowned for its ability to enantioselectively transform prochiral alkenes into epoxides. Before its development, catalysts for the asymmetric epoxidation of alkenes required the substrate to have a directing functional group, such as an alcohol as seen in the Sharpless epoxidation. This compound has two enantiomers, which give the appropriate epoxide product from the alkene starting material.

<span class="mw-page-title-main">1,2-Diaminopropane</span> Chemical compound

1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CH3CH(NH2)CH2NH2. A colorless liquid, it is the simplest chiral diamine. It is used as a bidentate ligand in coordination chemistry.

The Bargellini reaction is a chemical reaction discovered in 1906 by Italian chemist Guido Bargellini. The original reaction was a mixture of the reagents phenol, chloroform, and acetone in the presence of a sodium hydroxide solution. Prior to Bargellini's research, the product attributed to this multi-component reaction (MCR) had been described as a phenol derivative in chemistry texts at the time. However, Bargellini demonstrated that a carboxylic acid derivative was actually the correct structure.

<span class="mw-page-title-main">Nitro-Mannich reaction</span>

The nitro-Mannich reaction is the nucleophilic addition of a nitroalkane to an imine, resulting in the formation of a beta-nitroamine. With the reaction involving the addition of an acidic carbon nucleophile to a carbon-heteroatom double bond, the nitro-Mannich reaction is related to some of the most fundamental carbon-carbon bond forming reactions in organic chemistry, including the aldol reaction, Henry reaction and Mannich reaction.

References

  1. http://chem-international.com/wp-content/uploads/2013/08/Oleyl-Diamine.pdf [ bare URL PDF ]
  2. "(Z)-N-9-octadecenylpropane-1,3-diamine | 7173-62-8". Chemicalbook.com. Retrieved 2022-05-02.
  3. National Center for Biotechnology Information. PubChem Compound Database; CID=40764. https://pubchem.ncbi.nlm.nih.gov/compound/40764 (accessed 2016-12-24).
  4. "Duomeen OL - AkzoNobel Functional Applications". Archived from the original on 2017-11-27. Retrieved 2016-12-24.