Synthesis method of 2,2'-diaryl-4,4',5,5'-biphenyl tetraacid dianhydride monomer

A technology of biphenyltetracarboxylic dianhydride and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of low yield and difficult separation of products, and achieve the reduction of dielectric constant, improvement of solubility and light transmittance, and excellent thermal conductivity. The effect of stability

Inactive Publication Date: 2011-06-08
NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The synthetic route reported in this article is different from this patent, but there is oxidation of the methyl group on the benzene ring, the yield is not high and the product is difficult to separate

Method used

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  • Synthesis method of 2,2'-diaryl-4,4',5,5'-biphenyl tetraacid dianhydride monomer
  • Synthesis method of 2,2'-diaryl-4,4',5,5'-biphenyl tetraacid dianhydride monomer
  • Synthesis method of 2,2'-diaryl-4,4',5,5'-biphenyl tetraacid dianhydride monomer

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Embodiment 1

[0032] Synthesis of 2,2'-diphenyl-4,4',5,5'-biphenyltetraacid dianhydride

[0033] 2,2'-Diiodo-4,4',5,5'-biphenyl tetraethyl ester (40.0 g, 0.058 mol), phenylboronic acid (21.08 g, 0.17 mol), Pd (PPh 3 ) 4 (1.60 g), Na 2 CO 3 (18.29 g), toluene (287 mL), H 2 O (154 mL) on N 2 Under protection, heat to 70 °C. After reacting for 4 h, the toluene layer was dark red, filtered and separated. The toluene layer was evaporated to dryness to obtain dark red viscous liquid, which solidified after cooling. Recrystallized with ethanol to obtain 25.04 g of white solid, yield: 73.2%. Measured melting point: 159.5-162.6 °C. FI-TR (KBr, cm -1 ): 1724 (C=O), 1242 (C–O–C), 1136 (C–O–C), 697 (Ar–H). 1 H NMR (300 MHz, DMSO-d 6 , ppm) 7.84 (s, 1H, Ar–H), 7.46 (s, 1H, Ar–H), 7.22 (t, 1H, J =14.72 Hz, Ar-H), 7.11 (t, 2H, J =14.92 Hz, Ar-H), 6.56 (d, 2H, J =8.43 Hz, Ar-H), 4.25-4.34 (m, 4H, CH 2 ), 1.25-1.32 (m, 6H, CH 3 ). Elemental Analysis: C 36 h 34 o 8 (594.65). Theoretical ...

Embodiment 2

[0037] Synthesis of 2,2'-bis(4''-phenyl)phenyl-4,4',5,5'-biphenyltetraacid dianhydride

[0038] 2,2'-Diiodo-4,4',5,5'-biphenyl tetraethyl ester (40.0 g, 0.058 mol), 4'-biphenylboronic acid (31.68 g, 0.16 mol), Pd(PPh 3 ) 4 (1.60 g), Na 2 CO 3 (18.29 g), toluene (287 mL), H 2 O (154 mL) on N 2 Under protection, heat to 70 °C. After reacting for 4 h, the toluene layer was dark red, filtered and separated. The toluene layer was evaporated to dryness to obtain dark red viscous liquid, which solidified after cooling. Recrystallized with ethanol to obtain 30.95 g of white solid, yield: 71.6%. Measured melting point: 172-173 °C. FI-TR (KBr, cm -1 ): 1724 (C=O), 1243 (C–O–C), 1136 (C–O–C, 765), 697 (Ar–H). 1 H NMR (300 MHz, DMSO-d 6 , ppm) 7.90 (s, 1H, Ar–H), 7.65 (d, 2H, J =7.26 Hz, Ar-H), 7.53 (s, 1H, Ar–H), 7.37-7.49 (m, 5H, Ar–H), 7.66 (d, 2H, J =8.24Hz, Ar-H), 4.25-4.35 (m, 4H, CH 2 ), 1.25-1.33 (m, 6H, CH 3 ). Elemental Analysis: C 48 h 42 o 8 (746.84). Theor...

Embodiment 3

[0042] Synthesis of 2,2'-bis(4''-(α-naphthyl)phenyl)-4,4',5,5'-biphenyltetraacid dianhydride

[0043] 2,2'-Diiodo-4,4',5,5'-biphenyl tetraethyl ester (40.0 g, 0.058 mol), 4'-(α-naphthyl)phenylboronic acid (32.25 g, 0.13 mol) , Pd(PPh 3 ) 4 (1.60g), K 2 CO 3 (23.81 g), toluene (250 mL), H 2 O (150 mL), on N 2 Under protection, heat to 110 ℃. After reacting for 4 h, the toluene layer was dark red, filtered and separated. The toluene layer was evaporated to dryness to obtain dark red viscous liquid, which solidified after cooling. Recrystallized with ethanol to obtain 25.04 g of white solid, yield: 69.5%. Measured melting point: 179-180°C. FT-IR (KBr, cm -1 ): 1726 (C=O), 1292 (C–O–C), 1136 (C–O–C), 780 (Ar–H). 1 HNMR (300 MHz, DMSO-d 6 , ppm) 7.99 (s, 1H, Ar–H), 1.83-7.94 (m, 3H, Ar–H), 7.68 (s, 1H, Ar–H), 7.35-7.53 (m, 4H, Ar–H) , 7.26 (d, 2H, J =7.89 Hz, Ar–H), 6.79 (d, 2H, J =8.13 Hz, Ar–H), 4.36-4.48 (m, 4H, CH 2 ), 1.36-1.48 (m, 6H, CH 3 ). Elemental Analy...

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Abstract

The invention relates to a synthesis method of 2,2'-diaryl-4,4',5,5'-biphenyl tetraacid dianhydride monomer, which comprises the following steps of: firstly reacting 3,3',4,4'-biphenyl tetraacid dianhydride as a raw material with aliphatic amine to generate 3,3',4,4'-biphenyl diimide; then reacting the 3,3',4,4'-biphenyl diimide with I2 / KIO3 under concentrated acid conditions to generate 2,2'-diiodo-4,4',5,5'-biphenyl diimide; furthermore, converting the biphenyl diimide to 2,2'-diiodo-4,4',5,5'-biphenyl tetraester; then carrying out Suzuki reaction on the 2,2'-diiodo-4,4',5,5'-biphenyl tetraester and large conjugated arylboronic acid to obtain 2,2'-diaryl-4,4',5,5'-biphenyl tetraester containing the large conjugated arylboronic acid; and finally hydrolyzing, acidifying and dehydrating the 2,2'-diaryl-4,4',5,5'-biphenyl tetraester to obtain the 2,2'-diaryl-4,4',5,5'-biphenyl tetraacid dianhydride.

Description

technical field [0001] The invention belongs to the field of organic aromatic acid anhydrides, and in particular relates to a synthesis method of a 2,2'-diaryl-4,4',5,5'-biphenyltetraacid dianhydride monomer. [0002] Background technique [0003] Polyimide (PI) is a class of high-performance polymer materials with excellent mechanical properties, electrical properties, radiation resistance and heat resistance. It is widely used in high-tech fields such as aerospace, microelectronics and communications, and has become a very One of the promising materials. However, most polyimides are insoluble and infusible, and it is very difficult to process and shape, which limits their application scope to a certain extent. [0004] Ordinary polyimides are difficult to melt and dissolve, which makes them difficult to process and shape, which seriously affects their application value. The introduction of large conjugated side groups not only improves the solubility of the polyimide ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/89C07D405/14
Inventor 沈应中李月琴
Owner NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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