Description
2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6FAP,83558-87-6) is white
crystal. Its boiling point and density are expected to be 411.3±45.0 °C and 1.545±0.06 g/cm3, respectively. It is slightly soluble in DMSO and methanol.The product is non-toxic and can be stored at room temperature
away from light and air.
Synthesis
30 g two (3-nitro-4-hydroxyphenyl) hexafluoropropanes are dropped into
the 1000 mL autoclave, add 300 g DMF and 1.5 g palladium/carbon (the
mass fraction of palladium in the palladium/carbon is 5%), press
hydrogen to 1MPa, open stirring and be warmed up to 70 ℃, stop reaction
after two (3-nitro-4-hydroxyphenyl) hexafluoropropane content＜0.1%,
target product two (3-amino-4-hydroxyphenyl) hexafluoropropane
Fluoropropane gas phase content is 98%, and the system is black, and the
temperature of the still is lowered to room temperature, filtered, and
the filtrate is de-dried under reduced pressure at 70-80°C to obtain
bis(3-amino-4-hydroxyphenyl) hexafluoropropane crude product , the crude
product is recrystallized, the recrystallization solvent is water and
DMF, and the mass ratio of
bis(3-amino-4-hydroxyphenyl)hexafluoropropane, water and DMF is 1:4:2.
First, the bis(3-nitro-4-hydroxyphenyl) hexafluoropropane crude product
is mixed with the recrystallization solvent to increase the still
temperature to 60 °C and stir, and then the still temperature is reduced
to 10-20 °C for crystallization, filtered, After drying, 25.4 g of pure
bis(3-nitro-4-hydroxyphenyl)hexafluoropropane was obtained. The yield
of bis(3-amino-4-hydroxyphenyl)hexafluoropropane was 98.3% and the
purity was 99.6%. 1H-NMR (400MHz, D6-DMSO) δ (ppm): 4.64 (s, 4H), 6.42 (d, 2H), 7.57 (s, 2H), 6.65 (d, 2H), 9.36 (s, 2H). 19F-NMR (400MHz, D6-DMSO) δ (ppm): -62.78. [1].
Physical properties
White powder
Uses
2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane（BisAPAF） is a polyimide monomer.It is mairly used in the aynthesis of the heat resisting polymers,especially in the manufacture of specialty polymeoric electronic material-fluorinated polyimides.
Application
2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (Bis-AP-AF/6FAP) consists of two aminophenols bridged with a hexafluoropropane. The reaction of Bis-AP-AF and BTDA can be used to synthesise polyimide (PI) films. The tensile strength, tensile modulus and elongation at break of the PI films were significantly improved by 60Co irradiation with an optimum irradiation dose of 50 kGy. The maximum increments in tensile strength, tensile modulus and elongation at break of the irradiated PI films were 37.8%, 45.0% and 95.2%, respectively. The high proton conductivity and good chemical and thermal stability of these fluorinated films make them most suitable for use in fuel cell systems. In addition, Bis-AP-AF can be used to synthesise polybenzoxazole (TR-PBO) membranes for use as semiconductor fabrication materials.
General Description
2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane, also referred to as 4,4′-(1,1,1,3,3,3-hexafluoro-2,2-propanediyl)bis(2-aminophenol), is an aromatic diamine.
