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Preparation method of 1-bromine naphthalene

A technology of bromonaphthalene and bromine water, which is applied in the field of catalytic synthesis of 1-bromonaphthalene, can solve the problems of environmental pollution, high cost of raw materials, difficulty in recycling, etc., and achieve an environmentally friendly effect

Inactive Publication Date: 2007-03-07
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Badri, Rashid et al reported in "Phosphorus, Sulfur Silicon Relat.Elem" (2005) No. 180, No. 2, pp. 533-536, under the acidic environment provided by acetic acid, the use of potassium dichromate to oxidize copper bromide to obtain bromine source makes It reacts with naphthalene to synthesize 1-bromonaphthalene, the yield of its product can reach 88%, the reaction conditions are mild, the reaction temperature is 20 ℃, and the reaction time is 1.5 hours, but there are also some disadvantages at the same time: the cost of raw materials is high; the discharge contains chromium Waste liquid, difficult to recycle and pollute the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The first step, put 0.4mmol naphthalene and 0.2560g OMImBr ionic liquid into a closed reactor, add 0.5120g glacial acetic acid and stir and mix evenly, then add saturated bromine water containing 0.2mmol bromine simple substance;

[0020] The second step is to seal the airtight reactor treated in the first step and place it in a water bath with a temperature of 20°C for constant temperature reaction for 3 hours, take out the airtight reactor, open it after natural cooling, and extract it with benzene;

[0021] The third step is to add toluene reference substance in the solution obtained after benzene treatment, and carry out gas chromatographic analysis. The yield can reach more than 95% (calculated by naphthalene).

[0022] In the fourth step, the bottom liquid left after the extraction is taken and reused, and the yield of the target product can reach more than 80% (calculated by naphthalene).

Embodiment 2

[0024] The first step, put 0.4mmol naphthalene and 0.5120gBMImPF6 ionic liquid into a closed reactor, add 0.5120g glacial acetic acid and stir and mix evenly, then add saturated bromine water containing 0.3mmol elemental bromine;

[0025] The second step is to seal the airtight reactor treated in the first step and place it in a water bath with a temperature of 40°C for constant temperature reaction for 6 hours, take out the airtight reactor, open it after natural cooling, and extract it with acetone;

[0026] The 3rd step, in the solution gained after acetone treatment, add toluene standard substance, carry out gas chromatographic analysis. The yield can reach more than 95% (calculated by naphthalene).

[0027] In the fourth step, the bottom liquid left after the extraction is taken and reused, and the yield of the target product can reach more than 80% (calculated by naphthalene).

Embodiment 3

[0029] The first step, 0.4mmol naphthalene and 0.7680g OMImPF6 ionic liquid are put into airtight reactor, add 2.5600g glacial acetic acid simultaneously and mix well, then add the saturated bromine water of 0.4mmol elemental bromine;

[0030] The second step is to seal the airtight reactor treated in the first step and place it in a water bath with a temperature of 50°C for a constant temperature reaction for 24 hours, take out the airtight reactor, open it after natural cooling, and extract it with petroleum ether;

[0031] The third step, adding toluene reference substance in the solution obtained after petroleum ether treatment, carries out gas chromatographic analysis. The yield can reach more than 95% (calculated by naphthalene).

[0032] In the fourth step, the bottom liquid left after the extraction is taken and reused, and the yield of the target product can reach more than 80% (calculated by naphthalene).

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Abstract

The invention discloses a synthesizing method of 1-bromonaph in the organic chemical synthetic technological domain, which is characterized by the following: adopting naphthalene as raw material and saturated bromine water as bromine source; making glacial acetic acid and ion liquid with imidazole ring cation as solvent; reacting in the sealed reactor to produce 1-bromonaph; recycling the base liquid by over 80%.

Description

technical field [0001] The invention relates to a method for catalytically synthesizing 1-bromonaphthalene, specifically, a method for catalytically synthesizing 1-bromonaphthalene from naphthalene and bromine water, and belongs to the technical field of organic chemical synthesis. Background technique [0002] 1-bromonaphthalene is also called α-bromonaphthalene. 1-bromonaphthalene is a raw material for organic synthesis, and the dried product can be used as a heat carrier and for the determination of refractive index. The traditional method of synthesizing 1-bromonaphthalene is prepared by using naphthalene as raw material, carbon tetrachloride as solvent, and adding liquid bromine. The yield of this method is low, only 72%~75%. Simultaneously this method has used toxic solvent carbon tetrachloride, is harmful to environment. A kind of method for producing 1-bromonaphthalene is disclosed in "Collect.Czech.Chem.Commun" (2000) No. 65, No. 11, 1791-1804...

Claims

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Application Information

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IPC IPC(8): C07C17/12C07C25/22
CPCY02P20/582
Inventor 单永奎赵新华顾颖颖
Owner EAST CHINA NORMAL UNIVERSITY
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