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122-62-3

Basic Information
CAS No.: 122-62-3
Name: Dioctyl sebacate
Article Data: 11
Molecular Structure:
Molecular Structure of 122-62-3 (Dioctyl sebacate)
Formula: C26H50O4
Molecular Weight: 426.681
Synonyms: Dioctyl Sebacate;Bis(2-ethylhexyl) Sebacate;Dioctyl sebacate;‘Dioctyl’ sebacate;Sebacic Acid Dioctyl Ester;Sebacic acid di(2-ethylhexyl) ester;Sebacic Acid Bis(2-ethylhexyl) Ester;Bis(2-ethylhexyl)sebacate;Di(2-ethylhexyl) Sebacate;
EINECS: 204-558-8
Density: 0.914 g/cm3
Melting Point: -55 °C
Boiling Point: 435.51 °C at 760 mmHg
Flash Point: 189.655 °C
Solubility: <0.1 g/L (20 °C) in water
Appearance: colourless or light yellow oily liquid
Safety: 24/25
PSA: 52.60000
LogP: 7.62640
Synthetic route
111-20-6

1,10-decanedioic acid

104-76-7

2-Ethylhexyl alcohol

122-62-3

bis(2-ethylhexyl)sebacate

Conditions
ConditionsYield
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%
7327-98-2

decanedioic acid mono-(2-ethyl-hexyl ester)

A

111-20-6

1,10-decanedioic acid

B

122-62-3

bis(2-ethylhexyl)sebacate

Conditions
ConditionsYield
at 175 - 200℃; Equilibrium constant; Disproportionierung;
122-62-3

bis(2-ethylhexyl)sebacate

A

111-20-6

1,10-decanedioic acid

B

1632-16-2

2-ethyl-1-hexene

C

7327-98-2

decanedioic acid mono-(2-ethyl-hexyl ester)

Conditions
ConditionsYield
at 260 - 310℃; Rate constant; Pyrolysis;
122-62-3

bis(2-ethylhexyl)sebacate

A

75-07-0

acetaldehyde

B

123-38-6

propionaldehyde

C

123-72-8

butyraldehyde

Conditions
ConditionsYield
at 297 - 333℃;
122-62-3

bis(2-ethylhexyl)sebacate

106-35-4

heptan-3-one

Conditions
ConditionsYield
at 160 - 190℃;
122-62-3

bis(2-ethylhexyl)sebacate

Decanedioic acid 2-ethyl-hexyl ester 2-ethyl-2-hydroperoxy-hexyl ester

Conditions
ConditionsYield
With oxygen at 200℃; for 1h; Kinetics; study of the high-temperature oxidation of esters, synthetic hydrocarbons and their mixtures;
122-62-3

bis(2-ethylhexyl)sebacate

oxygen

oxygen

A

34557-54-5

methane

B

74-84-0

ethane

C

15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

D

hydrogen

hydrogen

Conditions
ConditionsYield
at 143℃; Zeitlicher Verlauf der Autoxydation des fluessigen Esters;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Dioctyl sebacate is bis(2-ethylhexyl) decanedioate. With the CAS registry number 122-62-3, it is also named as 1-Hexanol, 2-ethyl-, sebacate. The product's categories are Fatty Acid Esters (Plasticizer); Functional Materials; Plasticizer. It is colourless or light yellow oily liquid which is soluble in hydrocarbons, alcohols, ketones, esters, chlorine hydrocarbons, insoluble in glycol. Additionally, Bis(2-ethylhexyl) sebacate is flammable by fire, heat and oxidants. It will produce irritative fumes when buring. The storage environment should be ventilate, low-temperature and dry. Keep it separate from fire, heat and oxidants.

The other characteristics of Dioctyl sebacate can be summarized as: 
(1)ACD/LogP: 9.72; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.722; (4)ACD/LogD (pH 7.4): 9.722; (5)#H bond acceptors: 4; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 23; (8)Index of Refraction: 1.454; (9)Molar Refractivity: 125.97 cm3; (10)Molar Volume: 465.428 cm3; (11)Polarizability: 49.939×10-24 cm3; (12)Surface Tension: 32.442 dyne/cm; (13)Enthalpy of Vaporization: 69.181 kJ/mol; (14)Vapour Pressure: 0 mmHg at 25°C; (15)Rotatable Bond Count: 23; (16)Exact Mass: 426.37091; (17)MonoIsotopic Mass: 426.37091; (18)Topological Polar Surface Area: 52.6; (19)Heavy Atom Count: 30.

Preparation of Dioctyl sebacate:
The esterification of sebacic acid and octanol (mass ratio 1:1.6) in the catalysis of sulfuric acid (0.25% of the total mass of sebacic acid and octanol) to get monooctylester, this step esterification is easier. The second step generates double-ester that is more difficult. It must control the higher temperature, about 130 ~ 140 °C and then carry on dehydration under 0.093MPa vacuum, the reaction time is 3 ~ 5h, so it can achieve high yield. Crude ester is neutralized with 2% to 5% soda ash solution, washed under 70 ~ 80 °C, then took off the alcohol under 0.096 ~ 0.097MPa vacuum. When the flash point of crude reaches 205 °C, it is the end. Refined method is vacuum distillation.


Uses of Dioctyl sebacate: 
It is an excellent cold-resistant plasticizer and mainly used to make PVC cables, cold-resistant film, eatheroid, etc. And it also can be applicable to lubricating oils of jet engine and stationary liquid of gas chromatography.

People can use the following data to convert to the molecule structure.
1. SMILES:CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC
2. InChI:InChI=1/C26H50O4/c1-5-9-17-23(7-3)21-29-25(27)19-15-13-11-12-14-16-20-26(28)30-22-24(8-4)18-10-6-2/h23-24H,5-22H2,1-4H3.

The following are the toxicity data of Dioctyl sebacate:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 9500mg/kg (9500mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 62, 1982.
rabbit LD50 intravenous 540mg/kg (540mg/kg)   U.S. Army, Chemical Corps Medical Laboratories Research Reports. Vol. #256, Pg. 1954,
rat LD50 intravenous 900mg/kg (900mg/kg)   U.S. Army, Chemical Corps Medical Laboratories Research Reports. Vol. #256, Pg. 1954,