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Simple synthesis method of benzophenanthrene

A triphenylene and simple technology, which is applied in the field of preparation of 9,10-triphenylene, can solve the problems of high requirements, high energy consumption, large production investment, etc., and achieves low investment in reaction equipment, low energy consumption and economical efficiency. good effect

Active Publication Date: 2013-04-03
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has high requirements on equipment, large production investment, high energy consumption, and separation and purification also need to be improved.

Method used

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  • Simple synthesis method of benzophenanthrene
  • Simple synthesis method of benzophenanthrene
  • Simple synthesis method of benzophenanthrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 17.5g (0.72mol) of magnesium chips, 105g (0.6mol) of o-fluorobromobenzene, and 500ml of tetrahydrofuran into a 1L reaction flask equipped with a stirrer, a thermometer, a drying tube, and a reflux condenser, and heat to reflux for 0.5 hours while stirring. , then dropwise add a solution of 110g (0.63mol) o-fluorobromobenzene in 200ml tetrahydrofuran, drop it in 1.5 hours, finish the dropwise, keep warm for 4 hours, cool, filter with suction, distill off the organic phase tetrahydrofuran to obtain a yellow oil, Recrystallized with petroleum ether and ethyl acetate (volume ratio: 5:1) to obtain colorless needle-like crystals, which emit blue fluorescence under ultraviolet irradiation, with a yield of 91%. The carbon spectrum identified it as 9,10-triphenylene. The recovered tetrahydrofuran, petroleum ether and ethyl acetate can be recycled.

Embodiment 2

[0021] In a 1L reaction flask equipped with a stirrer, a thermometer, a drying tube, and a reflux condenser, add 17.5g (0.72mol) of magnesium chips, 105g (0.6mol) of o-fluorobromobenzene, 400ml of anhydrous tetrahydrofuran and 100ml of anhydrous 2 - Methylfuran, heated to reflux under stirring for 0.5 hours, then dropwise added a solution of 110g (0.63mol) o-fluorobromobenzene in 200ml tetrahydrofuran, dripped in 1.5 hours, the dropwise addition was completed, kept the reaction for 5.5 hours, cooled, suction filtered, Evaporate the organic phase tetrahydrofuran and 2-methylfuran to obtain a yellow oil, which is recrystallized from petroleum ether and ethyl acetate (volume ratio: 5:1) to obtain colorless needle-like crystals that radiate blue under ultraviolet light. Fluorescence, the yield was 85%, and it was determined to be 9,10-triphenylene by proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum. The recovered furan, petroleum ether and ...

Embodiment 3

[0023] Add 17.5g (0.72mol) of magnesium chips, 105g (0.6mol) of o-fluorobromobenzene, and 800ml of anhydrous diethyl ether in sequence to a 1L reaction flask equipped with a stirrer, a thermometer, a drying tube, and a reflux condenser, and heat to reflux under stirring. 0.5 hours, then dropwise add the solution of 110g (0.63mol) o-fluorobromobenzene in 50ml of anhydrous ether, drop it in 1.5 hours, end the dropwise addition, keep warm for 12 hours, cool, filter with suction, distill off the organic phase ether to get The yellow oil was recrystallized with petroleum ether and ethyl acetate (volume ratio: 5:1) to obtain colorless needle-like crystals, which emitted blue fluorescence under ultraviolet irradiation, and the yield was 87%. , and C-NMR spectrum identified as 9,10-triphenylene. The recovered ether, petroleum ether and ethyl acetate can be recycled.

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Abstract

The invention relates to a simple preparation method of 9,10-benzophenanthrene, which comprises the following steps: sequentially adding magnesium chips, ortho-dihalogenated benzene and solvent furan or aether into a reaction bulb, refluxing at 30-80 DEG C for 0.5 hour, and dropwisely adding ortho-dihalogenated benzene, wherein the ortho-dihalogenated benzene in the reaction bulb / magnesium chips / dropwisely added ortho-dihalogenated benzene mol ratio is 1:(1.0-1.8):(1.0-1.5), the dropwise addition speed is controlled so that the dropwise addition is finished within 1-2 hours, and the temperature is kept for 2-12 hours after the dropwise addition is finished; and carrying out vacuum filtration, distilling the filtrate to remove the solvent to obtain a yellow oil substance, and recrystallizing to obtain the 9,10-benzophenanthrene. The total yield of the optimized technique is higher than 85%. The synthesis method has the advantages of simple technique, low energy consumption, low reaction temperature, fewer byproducts, simple after-treatment and high product purity, is easy to control, and has favorable industrialization prospects.

Description

technical field [0001] The invention relates to a preparation method of 9,10-triphenylene. Background technique [0002] 9,10-benzophenanthrene (9,10-benzophenanthrene) is a polycyclic aromatic hydrocarbon compound, also known as 1,2,3,4-dibenzonaphthalene (l,2,3,4-dibenznaphthalene or isochrysene). In 1907, Mannich reported the synthesis method of the symmetrical aromatic compound triphenylene, and determined its chemical structure. In 1924, Schultz extracted this compound from aromatic hydrocarbon cracking products and named it triphenylene for the first time. 9,10-Triphenylene is a colorless needle-like crystal that emits blue fluorescence under ultraviolet light. It is a disc-shaped molecule with liquid crystallinity and can be used in discotic liquid crystal materials, optical and electronic devices . Triphenylene-like discotic liquid crystal derivatives have many types of liquid crystal phases and their efficient one-dimensional charge transport and energy transfer ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/38C07C1/32
Inventor 张秀芹王凯陈强
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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