122-62-3

Basic information

• Product Name: Dioctyl sebacate
• Synonyms: DIOCTYL SEBACATE;'DIOCTYL' SEBACATE;DI(2-ETHYLHEXYL) SEBACATE;BIS(2-ETHYLHEXYL)DECANEDIOATE;BIS(2-ETHYLHEXYL) SEBACATE;SEBACIC ACID DIOCTYL ESTER;SEBACIC ACID DI(2-ETHYLHEXYL) ESTER;SEBACIC ACID BIS(2-ETHYLHEXYL) ESTER
• CAS NO: 122-62-3
• Molecular Formula: C₂₆H₅₀O₄
• Molecular Weight: 426.67
• EINECS: 204-558-8
• Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer;organic chemical;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 122-62-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: -55 °C
• Boiling Point: 212 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 0.914 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.29E-13mmHg at 25°C
• Refractive Index: n20/D 1.450(lit.)
• Storage Temp.: 2-8°C
• Solubility: <1g/l
• Water Solubility: <0.1 g/L (20℃)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,1251
• BRN: 1806504
• CAS DataBase Reference: Dioctyl sebacate(CAS DataBase Reference)
• NIST Chemistry Reference: Dioctyl sebacate(122-62-3)
• EPA Substance Registry System: Dioctyl sebacate(122-62-3)

Safety Data

• Safety Statements: 24/25
• RTECS: VS1000000
• TSCA: Yes
• Hazardous Substances Data: 122-62-3(Hazardous Substances Data)

Usage

Chemical Properties

viscous colourless liquid

Uses

Different sources of media describe the Uses of 122-62-3 differently. You can refer to the following data:
1. In vacuum pumps.
2. Bis(2-ethylhexyl) sebacate is used as a plasticizer. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.
3. BEHS was used in preparing PVC-membrane anionic-surfactants-selective electrodes.

Production Methods

Di(2-ethylhexyl) sebacate is manufactured by esterifying 2-ethylhexanol with sebacic acid in the presence of an acid catalyst.

General Description

Clear pale yellow liquid with a mild odor. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Dioctyl sebacate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Dioctyl sebacate can react with oxidizing materials. Dioctyl sebacate will hydrolyze under acidic or basic conditions.

Fire Hazard

Dioctyl sebacate is probably combustible.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C26H50O4/c1-5-9-16-22(7-3)20-26(25(29)30,21-23(8-4)17-10-6-2)19-15-13-11-12-14-18-24(27)28/h22-23H,5-21H2,1-4H3,(H,27,28)(H,29,30)/p-2

Synthetic route

1,10-decanedioic acid (111-20-6) + 2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl)sebacate (122-62-3)

Conditions	Yield
With choline chloride; zinc(II) chloride at 110℃; for 16h;	99%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h; Time; Temperature; Concentration;	99%
With titanium(IV) isopropylate at 150 - 215℃; for 3.5h; Reagent/catalyst; Temperature; Large scale;	97.23%

decanedioic acid mono-(2-ethyl-hexyl ester) (7327-98-2) → 1,10-decanedioic acid (111-20-6) + bis(2-ethylhexyl)sebacate (122-62-3)

Conditions	Yield
at 175 - 200℃; Equilibrium constant; Disproportionierung;

bis(2-ethylhexyl)sebacate (122-62-3) → 1,10-decanedioic acid (111-20-6) + 2-ethyl-1-hexene (1632-16-2) + decanedioic acid mono-(2-ethyl-hexyl ester) (7327-98-2)

Conditions	Yield
at 260 - 310℃; Rate constant; Pyrolysis;

bis(2-ethylhexyl)sebacate (122-62-3) → acetaldehyde (75-07-0) + propionaldehyde (123-38-6) + butyraldehyde (123-72-8)

Conditions	Yield
at 297 - 333℃;

bis(2-ethylhexyl)sebacate (122-62-3) → heptan-3-one (106-35-4)

Conditions	Yield
at 160 - 190℃;

bis(2-ethylhexyl)sebacate (122-62-3) → Decanedioic acid 2-ethyl-hexyl ester 2-ethyl-2-hydroperoxy-hexyl ester

Conditions	Yield
With oxygen at 200℃; for 1h; Kinetics; study of the high-temperature oxidation of esters, synthetic hydrocarbons and their mixtures;

bis(2-ethylhexyl)sebacate (122-62-3) + oxygen → methane (34557-54-5) + ethane (74-84-0) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + hydrogen

Conditions	Yield
at 143℃; Zeitlicher Verlauf der Autoxydation des fluessigen Esters;

Upstream product

• 7327-98-2 decanedioic acid mono-(2-ethyl-hexyl ester) 
• 111-20-6 1,10-decanedioic acid 
• 104-76-7 2-Ethylhexyl alcohol 

Downstream Products

• 106-35-4 heptan-3-one 
• 75-07-0 acetaldehyde 
• 123-38-6 propionaldehyde 
• 123-72-8 butyraldehyde 
• 111-20-6 1,10-decanedioic acid 
• 1632-16-2 2-ethyl-1-hexene 
• 7327-98-2 decanedioic acid mono-(2-ethyl-hexyl ester) 

Related news

Technical noteCharge distributions of aerosol Dioctyl sebacate (cas 122-62-3) particles charged in a dielectric barrier discharger09/07/2019

The collection efficiencies of submicron aerosol particles using a two-stage, dielectric barrier discharge (DBD) type electrostatic precipitator have been reported previously [Byeon et al. (2006). Collection of submicron particles by an electrostatic precipitator using a dielectric barrier disch...detailed

Formation of an adsorption film of MoS2 nanoparticles and Dioctyl sebacate (cas 122-62-3) on a steel surface for alleviating friction and wear09/06/2019

Solid sphere-like nano-MoS2 particles were synthesized via a modified chemical method. The as-synthesized nano-MoS2 could improve the tribological properties of dioctyl sebacate (DOS) more compared with a commercial 2H micro-MoS2. The lubrication of micro-MoS2 in DOS was ascribed to the tribofil...detailed

Relevant articles and documents

Preparation of nano-SO4 2- /TiO2 catalyst and its application in esterification of sebacic acid with 2-ethyl hexanol

A pure anatase phase nano-SO 4 2- /TiO2 catalysts were synthesized and their catalytic activities were tested. Nano-SO 4 2- /TiO2 shows high activity and effective re-usable when used as basic catalysts for the synthesis of dioctyl sebacate.

Micro-flow nanocatalysis: synergic effect of TfOH@SPIONs and micro-flow technology as an efficient and robust catalytic system for the synthesis of plasticizers

The combination of continuous flow technology with immobilizing of only 0.13?mol% of triflic acid (TfOH) on silica-encapsulated superparamagnetic iron oxide nanoparticles (SPIONs) under solvent-free conditions successfully provided a powerful, efficient, and eco-friendly route for the synthesis of plasticizers. The turnover frequency value in micro-flow conditions varied in the range of 948.7 to 7384.6 h?1 compared to 403.8 to 3099 h?1 for in-flask. This technique works efficiently, encouraging future applications of micro-flow nano-catalysis in green chemistry.

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.