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Method for preparing high-purity methylbenzenecarbonitrile and derivatives thereof

A technology of o-toluonitrile and o-methyl bromobenzene is applied in the field of preparation of high-purity o-toluonitrile and derivatives thereof, and can solve the problems of long reaction time, low product yield and purity, pollution of three wastes and the like

Inactive Publication Date: 2015-12-09
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, the existing technology mainly has a long reaction time, generally more than 24 hours, troublesome post-treatment, and alkaline sodium hypochlorite is required to treat the waste liquid, the three wastes are seriously polluted, and the yield and purity of the obtained product are low.

Method used

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  • Method for preparing high-purity methylbenzenecarbonitrile and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 3g of sodium carbonate and 0.0025g of palladium acetate into 11mL of anhydrous N-methylpyrrolidone (NMP), stir, add 0.003g of dppf (1,1 diphenylphosphinoferrocene), heat up to 100°C, and Add the grams of 2-bromo-5-fluorotoluene and the same molar amount of sodium carbonate, add potassium ferrocyanide (K 4 [Fe(CN) 6 ]) 2g, reacted under nitrogen protection for 13 hours, quenched with 35mL water, extracted with 30mL×3 n-hexane, washed with 30mL×3 saturated brine, dried over anhydrous sodium sulfate for 12h, and spin-dried the solvent under reduced pressure to obtain the crude product. Take 2g of the crude product In a three-necked flask, add ethers (petroleum ether) or a mixture of petroleum ether and methyl tert-butyl ether 5mL, heat up and stir to 40°C, dissolve the crude product, cool to 20°C, stir for 2h, then stir in an ice bath for 0.5h , filtered, washed the filter cake with cold petroleum ether, and dried the filter cake under reduced pressure to obtain 1.7g ...

Embodiment 2

[0032] Add 5g of sodium carbonate and 0.004g of palladium acetate into 20mL of anhydrous N,N-dimethylacetamide (DMAC), stir, add 0.005g of dppf (1,1 diphenylphosphinoferrocene) and heat up to 130 ℃, add 2-bromo-5-fluorotoluene and sodium carbonate in the same molar amount 9g at one time, add potassium ferrocyanide (K 4 [Fe(CN) 6 ]) 3.75g, heat preservation reaction for 11 hours, quenched with 30mL water, extracted with 50mL×3 n-hexane, washed with 50mL×3 saturated brine, dried over anhydrous magnesium sulfate for 12h, and spin-dried the solvent under reduced pressure to obtain a crude product, 5.8g Put the crude product in a three-necked flask, add 15 mL of ether (petroleum ether) or a mixture of petroleum ether and methyl tert-butyl ether, heat up and stir to 40°C, dissolve the crude product, cool to 20°C, stir for 2h, and then stir in an ice bath for 1h. Filter, wash the filter cake with cold petroleum ether, and dry the filter cake under reduced pressure to obtain 4.8 g of...

Embodiment 3

[0035] Add 2.5g of sodium carbonate and 0.002g of palladium acetate into 10mL of anhydrous N,N-dimethylacetamide (DMAC), stir, add 0.0025g of dppf (1,1 diphenylphosphinoferrocene), and heat up to 130°C, add 4.5g of 2-bromo-5-fluorotoluene and sodium carbonate at one time, add potassium ferrocyanide (K 4 [Fe(CN) 6 ]) 1.88g, heat preservation reaction for 11 hours, quenched with 15mL water, extracted with 30mL×3 n-hexane, washed with 30mL×3 saturated saline, dried over anhydrous magnesium sulfate for 12h, and spin-dried under reduced pressure to obtain a crude product, 2.9g Put the crude product in a three-necked flask, add ethers (petroleum ether) or 8 mL of a mixture of petroleum ether and methyl tert-butyl ether, heat up and stir to 40°C, dissolve the crude product, cool to 20°C, stir for 2h, then stir in an ice bath for 1h, Filter, wash the filter cake with cold petroleum ether, and dry the filter cake under reduced pressure to obtain 2.6 g of the product.

[0036] The rea...

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Abstract

The invention relates to a method for preparing high-purity methylbenzenecarbonitrile and derivatives thereof. The method comprises the following steps of firstly, catalytically coupling cyanogen radicals to the methylbenzenecarbonitrile and the derivatives thereof by adopting a nontoxic low-price cyanide reagent under the protection of nitrogen gas to obtain a product; secondly, recrystallizing the product by using an organic solvent, and purifying to prepare the higher-purity methylbenzenecarbonitrile and derivatives thereof. The method has the advantages of fewer side reactions, simple post treatment, no toxicity and no harm; according to the method, the purity of the product can reach over 99.75 percent; the method is suitable for scale industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation of high-purity o-methyl benzonitrile and derivatives thereof, more specifically, relate to the method for the nitrile group and purification of medium halogenated benzene. Background technique [0002] O-methylbenzonitrile and its derivatives are important organic synthesis intermediates, which are widely used in the preparation of pesticides, medicines, dyes and other fine chemical products. In recent years, with the widespread use of polyester fluorescent whitening agents in China, The demand for o-tolunitrile and its derivatives as its important raw material is also increasing. At the same time, o-tolunitrile and its derivatives are important intermediates of gliptin diabetes drugs. With the broad market demand for diabetes drugs, the demand for o-tolunitrile and its derivatives is also increasing. [0003] At present, the preparation methods of o-methylbenzonitrile and derivatives thereof main...

Claims

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Application Information

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IPC IPC(8): C07C255/50C07C253/14
Inventor 游莉江洁滢邓俊丰刘瑜张晓杨力鑫卫金强
Owner CHENGDU UNIV
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