Antioxidant 245

DryPowder; OtherSolid

Triethyleneglycol-bis-{3-(3-tert.butyl-4-hydroxy-5-methylphenyl)propionate} 15 grams of triethyleneglycol (0.10 moles), and 0.48 grams of lithium amide were heated together with 55.5 grams of ethyl 3-{(3-tert.-butyl-5-methyl) propionate} at 125C when ethanol began to evolve. The reaction mixture was then heated at 130 to 135C for 105 hours and at 155 to 157 for 3.75 hours during which 11.4 ml of ethanol was distilled. Finally, the melt was heated at 155 to 157C at 15 mm Hg for 1.5 hours. 1.6 grams of glacial acetic acid was added to the melt at 50C the color changing from purple to yellow. The product was dissolved in 150 ml of benzene and the turbid solution successively washed with water, 6N aqueous hydrochloric acid, 2N aqueous sodium hydroxide and finally water until neutral. After drying over anhydrous sodium sulfate, the benzene was removed by distillation at reduced pressures. The isolated residue was triturated with heptane, and cyclohexane during which crystallization occured. The crystals were filtered and recrystallized from a solvent mixture of 150 ml isopropanol and 60 ml of water and finally recrystallized from nitromethane. White crystals were obtained melting at 76 to 78C.(2) Into a 1-liter four-necked flask equipped with a stirrer, a condenser, a thermometer, and a nitrogen introducing tube were introduced 327.9 g (1.31 moles) of methyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, 85.6 g (0.57 mole) of triethylene glycol, and 0.9 g (0.00431 mole) of monobutyltin oxide. The mixture was allowed to react at 170 C. for 1 hour, and the resulting methanol was distilled off. The reaction was continued for further 8 hours under a reduced pressure of 60-70 mmHg while bubbling nitrogen gas into the solution and thus completed. Excess methyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate was distilled off in an amount of 40.5 g at 150-185 C. under 0.5 -0.2 mmHg by thin film distillation. This distillate can be reused, as it is, for the next reaction. Then, the reaction mixture was cooled to 115 C. and returned to atmospheric pressure by the introduction of nitrogen gas, and dissolved homogeneously by adding 260 g of toluene. The solution was washed with 200 g (0.11 mole) of 5% oxalic acid water at 80 C. and then with 200 g of water twice for partitioning to two layers. The toluene layer was concentrated at 120 C. under 30 mmHg to give a pale yellow tacky substance. The pale yellow tacky substance so obtained was recrystallized from methanol-water to Yield 317.8 g of white crystals of triethylene glycol bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate] as intended. Yield: 95%, residual tin content: 2 ppm.(1) A 1-liter four-necked flask fitted with a stirrer, a fractionating tube with condenser, a dropping funnel and a thermometer were charged with 300 g (1.2 moles) of methyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, 85.6 g (0.57 mole) of triethylene glycol and 0.9 g (0.00431 mole) of monobutyltin oxide, and the mixture was subjected to reaction at 170 C. for 14 hours while dropwise adding toluene. The resulting methanol was distilled off, together with the added mixture was cooled to 115 C., 260 g of toluene was added to dissolve it homogeneously. The solution was washed with 200 g (0.11 mole) of 5% oxalic acid water at 80 C. and then with 200 g of water twice to partition the solution. The toluene layer was concentrated at 120 C. under 30 mmHg to result in a pale yellow sticky substance. The pale yellow sticky substance thus obtained was recrystallized from methanol-water to afford 315 g of white crystals of triethylene glycol bis-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate] as intended. Yield: 94%, residual tin content: 2 ppm, transmittance: 99% (by spectrophotometry at 425 nm).

This product is used as an antioxidant for the processing of styrene polymers such as HIPS, MBS, ABS, engineering plastics such as POM, PA, and polyurethane such as spandex and the improvement of long-term thermal stability. It is also an effective chain terminator in the PVC polymerization process. This product has no effect on polymer reaction. When used in high impact polystyrene and polyvinyl chloride, it can be added to the monomer before polymerization.

Oxidizing/reducing agents

Adhesives and sealants

Molecular Weight:586.8
XLogP3:6.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:19
Exact Mass:586.35056855
Monoisotopic Mass:586.35056855
Topological Polar Surface Area:112
Heavy Atom Count:42
Complexity:734
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes