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

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

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

Downstream Products

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

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.

Exceptionally active and reusable nanobiocatalyst comprising lipase non-covalently immobilized on multi-wall carbon nanotubes for the synthesis of diester plasticizers

A new method for the synthesis of dicarboxylic acid esters in the presence of a new heterogeneous nanobiocatalyst consisting of Candida antarctica lipase B immobilized on multi-walled carbon nanotubes (MWCNTs) has been developed. Selection and characterization of the support for Candida antarctica lipase B (CALB) was initially performed. Pristine and modified MWCNTs of different geometries, morphologies and surface/core modifications were tested as a lipase carrier and determining that the CheapTubes MWCNTs nanobiocatalyst with a 15.7 wt.% CALB loading was the most active nanobiocatalyst. The model reaction of succinic acid with n-butanol was carried out with a 4-molar excess of alcohol and 150 mg of nanobiocatalyst per 1 mmol of succinic acid at 45 °C in cyclohexane. The di-n-butyl succinate was obtained with 95% yield after 3 h. The activities of the new nanobiocatalysts were compared with the benchmark Novozyme-435 and other acidic catalysts. Recycling studies demonstrated the possibility of utilizing the most active MWCNTs-lipase biocatalyst six times without any significant loss of activity. The main advantage of this study is the superior activity of the new nanobiocatalyst, which resulted in a significant reduction of reaction times as compared to those reported in the literature.

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.

Preparation method for cold-resistant plasticizer dioctyl sebacate

The invention relates to a preparation method for a cold-resistant plasticizer dioctyl sebacate, and belongs to the field of PVC auxiliary agents. The preparation method comprises the following steps: esterification, dealcoholysis, neutralization, distillation, adsorption and press filtration. The technical scheme employs 2-ethylhexanol and sebacic acid as raw materials and employs one or more titanates as a catalyst for esterificatoin, and then excessive 2-ethylhexanol is removed; then neutralization is performed, and a dioctyl sebacate crude product is prepared; and then the dioctyl sebacate crude product is subjected to reduced-pressure distillation, adsorption and press filtration, the high-quality high-yield high-purity cold-resistant plasticizer dioctyl sebacate product is prepared. The product quality reaches super grade standard.

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.

Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives

Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.

Liquid-liquid biphasic synthesis of long chain wax esters using the Lewis acidic ionic liquid choline chloride·2ZnCl2

The first liquid-liquid biphasic synthesis of wax esters in a Lewis acidic ionic liquid, choline chloride·2ZnCl2 by the esterification of long chain carboxylic acids with long chain alcohols is described. The reported reaction system has the advantages of both homogeneous and heterogeneous catalysis with high product yield and the ease of product as well as catalyst separation without the use of an organic solvent. The ionic liquid studied plays the dual role of solvent as well as catalyst and is recycled up to six times without any significant loss of activity.