103-24-2

Basic information

• Product Name: AZELAIC ACID DI(2-ETHYLHEXYL) ESTER
• Synonyms: BIS(2-ETHYLHEXYL) AZELATE;BIS(2-ETHYLHEXYL) NONANEDIOATE;AZELAIC ACID DIOCTYL ESTER;AZELAIC ACID BIS(2-ETHYLHEXYL) ESTER;AZELAIC ACID DI(2-ETHYLHEXYL) ESTER;DI(2-ETHYLHEXYL) AZELATE;DIOCTYL AZELATE;DIISOOCYL AZELATE
• CAS NO: 103-24-2
• Molecular Formula: C₂₅H₄₈O₄
• Molecular Weight: 412.65
• EINECS: 203-091-7
• Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
• Mol File: 103-24-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: -67°C
• Boiling Point: >282°C
• Flash Point: 211 °C
• Appearance: /
• Density: 0,92 g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4460 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: 0.1mg/L(25 oC)
• CAS DataBase Reference: AZELAIC ACID DI(2-ETHYLHEXYL) ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: AZELAIC ACID DI(2-ETHYLHEXYL) ESTER(103-24-2)
• EPA Substance Registry System: AZELAIC ACID DI(2-ETHYLHEXYL) ESTER(103-24-2)

Safety Data

• RTECS: CM2000000
• Hazardous Substances Data: 103-24-2(Hazardous Substances Data)

Usage

Chemical Properties

It is a high-boiling point liquid (237°C at 5 mmHg) that is soluble in alcohol, acetone, and benzene and insoluble in water.

Uses

It is used as a plasticizer.

Production Methods

Di(2-ethylhexyl) azelate is manufactured by reacting 2- ethylhexanol with azelaic acid in the presence of an acid catalyst.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C25H48O4/c1-5-9-15-21(7-3)19-25(24(28)29,20-22(8-4)16-10-6-2)18-14-12-11-13-17-23(26)27/h21-22H,5-20H2,1-4H3,(H,26,27)(H,28,29)/p-2

Synthetic route

azelaic acid (123-99-9) + 2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl) azelaate (103-24-2)

Conditions	Yield
With [HSO3-pmim]+[HSO4]-catalyst for 0.333333h; Reagent/catalyst; Microwave irradiation;	99.1%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h;	94%

Upstream product

• 123-99-9 azelaic acid 
• 104-76-7 2-Ethylhexyl alcohol 

Relevant articles and documents

Lubricity, tribological and rheological properties of green ester oil prepared from bio-based azelaic acid

Plant oil derived compounds have been used as the raw material for the synthesis of green biolubricant. Azelaic acid derived from oleic acid is one of the interesting compounds. The synthesis of azelate esters oil based synthetic green biolubricants was carried out. The esterification process of azelaic acid with variety type of alcohols was catalyzed by concentrated H2SO4. The yields percentages of azelate esters oil produced were varied depending their overall molecular structure. The azelate esters oil properties were evaluated for their suitability as a biolubricant. The results showed that the linear azelate esters oil showed high pour point values in a range of 15 to 5°C for di-decyl azelate, di-octyl azelate and di-hexyl azelate respectively. On the other hands, the branch azelate esters oil showed very low pour point of -70, -58 and -50°C for di-2-butyloctyl azelate, di-2-ethylhexanol azelate and di-2-ethylbutyl azelate, respectively. Moreover, the linear azelate esters oil gave high values of flash point, viscosity index and oxidative stability, and they were slightly affected by branching molecule structure. The tribological and rheological properties of high molecular azelate esters oil were also performed. Subsequently, most of them were classified as non-Newtonian fluids and having boundary lubrication properties with low friction coefficient. The branch azelate esters oil is plausible to be used as green biolubricants in many applications including automotive, marine engine oils, compressor oils, hydraulic fluids, gear oils and industrial biolubricants.

Nano-SO42-/TiO2catalyzed eco-friendly esterification of dicarboxylic acids

Nano-SO42-/TiO2 was prepared by wet impregnation method. The structure and properties of the prepared nano-SO42-/TiO2catalyst was characterized by XRD, SEM, TEM and BET analysis. The catalytic activities of the catalysts were tested by the esterification of sebacic acid with 2-ethyl hexanol and a series of other dicarboxylic acid. The influence factors on the reaction, such as the catalyst calcination temperature, reaction temperature/time and the molar ratio of acid to alcohol were extensively explored. Nano-SO42-/TiO2prepared exhibited much higher catalytic activity in esterification reactions. By applying the optimized reaction condition, i.e. 160 C, 2 h, 5 wt % nano-SO42-/TiO2with a 1:3 molar ratio of sebacic acid to 2-ethyl hexanol, higher than 99 % isolated of the desired ester could be obtained.