Preparation method of biphenyl derivatives

A derivative and biphenyl technology, applied in the field of preparation of biphenyl derivatives, can solve problems such as difficult recovery, unfavorable industrial production, safety accidents, etc., and achieve the effects of avoiding operation process, realizing production cost, and reducing energy consumption.

Inactive Publication Date: 2015-01-07
HARBIN INST OF TECH AT WEIHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As we all know, tetrahydrofuran or ether has a low boiling point, high toxicity and is not ...

Method used

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  • Preparation method of biphenyl derivatives
  • Preparation method of biphenyl derivatives

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Experimental program
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Effect test

Embodiment 1

[0035] 4-Bromo-o-xylene (36.6 g, 0.2 moL), zinc powder (13 g, 0.2 moL), anhydrous 2-methyltetrahydrofuran (52 g, 0.6 moL), anhydrous NiCl 2 (0.51 g, 4 mmoL) and triphenylphosphine (2 g, 8 mmoL), mixed in a nitrogen atmosphere, 85 o After C reacted for 8 hours, cooled, filtered off the inorganic matter, and the filtrate recovered 49 g of 2-methyltetrahydrofuran solvent through distillation, and collected 145 ~ 165 by distillation under reduced pressure. o C fraction (pressure 1~3 mmHg). 19.1 g of 3, 3’, 4, 4’-tetramethylbiphenyl was obtained with a yield of 90% and a melting point of 74-75 o c.

Embodiment 2

[0037] 3-Chloro-o-xylene (28 g, 0.2 moL), manganese (1.1 g, 0.2 moL), anhydrous 2-methyl-substituted tetrahydrofuran (43 g, 0.5 moL), anhydrous NiCl 2 (0.51 g, 4 mmoL), bipyridine (1.25 g, 8 mmoL) were mixed in a nitrogen atmosphere, 80 o C reacted for 8 hours, cooled, filtered off inorganic matter, and the filtrate recovered 40 g of 2-methyltetrahydrofuran solvent through distillation, and collected 135 to 155 by distillation under reduced pressure. o Fraction C (pressure 1~3 mmHg), obtained 17.9 g of 2, 2’, 3, 3’-tetramethylbiphenyl with a yield of 85% and a melting point of 115~116 o c.

Embodiment 3

[0039] Dimethyl 4-chlorophthalate (22.8 g, 0.1 moL), zinc powder (6.5 g, 0.1 moL), anhydrous 2,5-dimethyltetrahydrofuran (50 g, 0.5 moL), anhydrous NiBr 2 (0.65 g, 3 mmoL), triphenylphosphine (2.6 g, 10 mmoL), 75 o C reaction for 10 hours, then cooled and filtered to remove inorganic matter, and the filtrate was distilled to recover 46 g of 2,5-dimethyltetrahydrofuran solvent to obtain the crude product of tetramethyl biphenyl tetracarboxylate, which was recrystallized from methanol to obtain 17 g of pure product, with a yield of 88 %. Add the obtained tetramethyl biphenyl tetracarboxylate into a mixture of 100 mL of water and 10 mL of concentrated sulfuric acid, heat to reflux for 24 hours, cool and filter, collect the precipitate, and o C was heated in three stages for 15 hours to obtain 12.5 g of 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride, with a yield of 96%.

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Abstract

The invention discloses a preparation method of biphenyl derivatives. According to the method, the biphenyl derivatives are generated by carrying out coupling reaction by taking non-water-soluble alkyl-substituted tetrahydrofuran as a solvent, halogenated O-xylene, halogenated alkyl phthalate and halogenated phthalimide as raw materials, manganese, aluminum or zinc as a reducing agent and nickel salt, cobalt salt, palladium salt, iron salt, copper salt or a complex compound composed of the salts, organic phosphorus and organic amine as a catalyst.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a preparation method of biphenyl derivatives. Background technique [0002] Biphenyltetraacid dianhydride, referred to as BPDA, is one of the important dianhydride monomers for the synthesis of polyimide materials. There are three main isomers of biphenyltetracarboxylic dianhydride, namely 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride, 2,3',3,4'-biphenyltetracarboxylic dianhydride and 2, 2', 3,3'-Biphenyltetracarboxylic dianhydride. Among them, the polymer synthesized by the asymmetric structure of 2,3',3,4'-biphenyltetraacid dianhydride has an order of magnitude lower melt viscosity than its isomer polymer, and this property is expected to completely change the decades-old polymers. Contradictions between properties and difficult processing of imide resin matrix composites. At present, the output of 2,3’,3,4’-biphenyl dianhydride is limited and very expensive. Th...

Claims

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Application Information

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IPC IPC(8): C07D209/48B01J31/22
CPCC07D307/89C07C1/26C07C2531/22C07D209/48C07C15/14
Inventor 高昌录周建超孙秀花
Owner HARBIN INST OF TECH AT WEIHAI
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