Low-cost and environment-friendly synthesis method of biphenyl derivatives

A technology for green synthesis and derivatives, which is applied in the field of low-cost green synthesis of biphenyl derivatives, can solve problems such as low boiling point, unfavorable industrial production, and difficult recycling, so as to simplify the process operation steps, facilitate recycling and reuse, and realize the preparation cost Effect

Inactive Publication Date: 2015-02-11
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 eas

Method used

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  • Low-cost and environment-friendly synthesis method of biphenyl derivatives
  • Low-cost and environment-friendly synthesis method of biphenyl derivatives
  • Low-cost and environment-friendly synthesis method of biphenyl derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 4-Bromo-o-xylene (36.6 g, 0.2 moL), zinc powder (13 g, 0.2 moL), anhydrous cyclopentyl methyl ether (60 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, cool down, filter off the inorganic matter, and the filtrate recovered 49 g of 2-methyltetrahydrofuran solvent through distillation, and collected 145 ~ 155 g by distillation under reduced pressure. o Fraction C (pressure 1~3 mmHg), obtained 19.1 g of 3, 3’, 4, 4’-tetramethylbiphenyl, yield 90%, melting point 74~75 o c.

Embodiment 2

[0042] 3-Chloro-o-xylene (28 g, 0.2 moL), manganese (1.1 g, 0.2 moL), anhydrous cyclopentyl methyl ether (50 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 145 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

[0044] Dimethyl 4-chlorophthalate (22.8 g, 0.1 moL), zinc powder (6.5 g, 0.1 moL), anhydrous cyclopentyl methyl ether (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, and the obtained crude product of tetramethyl biphenyl tetracarboxylate 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 sulfuric acid, heat to reflux for 24 hours, cool and filter, collect the precipitate, and o The C program divided the temperature into three stages and raised the temperature 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 low-cost and environment-friendly synthesis method of biphenyl derivatives. According to the method, a water-insoluble environment-friendly solvent cycloalkyl methyl ether is used as a solvent system of the reaction, halogenated o-xylene, halogenated alkyl phthalate ester or halogenated phthalimide is used as raw material and is subjected to coupling reaction in the presence of manganese or aluminum, or zinc as a reducing agent and a nickel salt, cobalt salt, palladium salt, iron salt or copper salt of transition metal or a complex prepared from the salt and a ligand such as organic phosphorus phosphine and organic amine as a catalyst to obtain the biphenyl derivatives.

Description

technical field [0001] The invention relates to the field of organic synthetic chemistry, in particular to a low-cost and green method for synthesizing 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 asymmetric structure of 2,3',3,4'-biphenyltetraacid dianhydride synthesized polymers has an order of magnitude lower melt viscosity than its isomer polymers, and this property is expected to revolutionize resins for decades. The contradiction between the properties of matrix composites and the difficulty of processing. At present, there are few reports on the synthesis methods of 2,3',3,4'-biphenyl ...

Claims

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Application Information

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IPC IPC(8): C07C1/26C07C15/14C07D307/89
Inventor 高昌录孙秀花
Owner HARBIN INST OF TECH AT WEIHAI
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