Dioctyl sebacate

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: