CN108863802B - Preparation method of 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl - Google Patents
Preparation method of 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl Download PDFInfo
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- CN108863802B CN108863802B CN201810878699.XA CN201810878699A CN108863802B CN 108863802 B CN108863802 B CN 108863802B CN 201810878699 A CN201810878699 A CN 201810878699A CN 108863802 B CN108863802 B CN 108863802B
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- C07—ORGANIC CHEMISTRY
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- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
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- C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups
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Abstract
The invention provides a preparation method of 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl, which comprises the following steps: dissolving 2,2 ' -bis (trifluoromethyl) biphenyl serving as a raw material in N-methylpyrrolidone, dropwise adding sulfonyl chloride at room temperature, heating after dropwise adding, adding a nitration reagent in batches, slowly adding ice water into a reaction solution to cool to room temperature after the raw material completely reacts, adjusting the pH to be neutral by using an alkaline buffer solution, taking an oil layer, adding methanol for refluxing, slowly cooling, stirring, and filtering to obtain 2,2 ' -bis (trifluoromethyl) -4,4 ' -dinitrobiphenyl yellow solid. The method for nitrating by adopting ammonium nitrate has the advantages of higher reaction yield, mild reaction condition, simple post-treatment, good product quality and the like.
Description
Technical Field
The invention relates to a preparation method of diamine monomer 2,2 '-bis (trifluoromethyl) -4, 4' -diaminobiphenyl which can be used as a synthetic polyimide liquid crystal material.
Background
2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl is an important raw material for preparing liquid crystal material 2,2 '-bis (trifluoromethyl) -4, 4' -diaminobiphenyl. The 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl can be used for preparing the 2,2 '-bis (trifluoromethyl) -4, 4' -diaminobiphenyl after the nitro is reduced by palladium-carbon hydrogenation or iron powder reduction and other methods. The 2,2 '-bis (trifluoromethyl) -4, 4' -diaminobiphenyl is an important polyimide monomer material, is mainly used for manufacturing flexible liquid crystal display screens, transparent touch films of electronic equipment, flexible solar cell lining plates and flexible LED (light-emitting diode) lighting equipment, is a new chemical material called 'problem solving ability in the field of materials' in the industry, has excellent comprehensive properties of high temperature resistance, high strength, high insulation, low dielectric constant, low dielectric loss and the like, is widely applied to the high and new technical field, and is an irreplaceable key basic material in the industries of microelectronic devices, electric wires and cables, computers, digital electrical appliances and the like.
At present, the 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl prepared by a nitration method is reported in documents:
1) patent WO2008059724 adopts nitric acid and concentrated sulfuric acid to react for 10 hours in dichloromethane at 25-30 ℃ to carry out nitration reaction, the conversion rate of the generated 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl is 95.5%, and the yield is 77%.
2) Patent JP2008255037 also adopts mixed acid as a nitrating reagent, and reacts for 6 hours at 35 ℃ in dichloromethane, so that the conversion rate of the generated 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl is 87%, and the yield is 76%.
3) In patent JP2005126331, a mixed acid is used as a nitrating reagent, and the mixed acid is reacted in toluene at 40 ℃ or lower for 8 hours to generate 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl with the yield of 91.5%.
4) JP03044355 discloses nitration with mixed acids in 86% yield.
5) In patent CN104211944, the reaction is carried out under the condition of using water as solvent at room temperature by using mixed acid to obtain 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl, and the yield is 66%.
The nitration reagents used in the prior art for preparing the product by a nitration method are all as follows: mixed acid, namely: nitric acid/concentrated sulfuric acid. The product prepared by the nitration method has low yield, is easy to generate polynitro compounds, causes difficult product separation, and has high risk of using mixed acid.
Disclosure of Invention
In view of the above, the present invention is directed to a method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl.
In order to achieve the purpose, the technical scheme of the invention is realized as follows: a preparation method of 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl is characterized by comprising the following steps: the method comprises the following steps: dissolving 2,2 ' -bis (trifluoromethyl) biphenyl serving as a raw material in N-methylpyrrolidone, dropwise adding sulfonyl chloride at room temperature, heating after dropwise adding, adding a nitration reagent in batches, slowly adding ice water into a reaction solution to cool to room temperature after the raw material completely reacts, adjusting the pH to be neutral by using an alkaline buffer solution, taking an oil layer, adding methanol for refluxing, slowly cooling, stirring, and filtering to obtain 2,2 ' -bis (trifluoromethyl) -4,4 ' -dinitrobiphenyl yellow solid.
The reaction structure formula is as follows:
preferably, the nitrating agent is one of potassium nitrate, sodium nitrite, cupric nitrate or ammonium nitrate.
Preferably, the nitrating agent is ammonium nitrate.
Preferably, the molar ratio of the 2, 2' -bis (trifluoromethyl) biphenyl to the sulfonyl chloride to the N-methyl pyrrolidone to the nitrating reagent is 1: (1.4-2.2): (5-9): (2.5-3.5).
Preferably, the molar ratio of the 2, 2' -bis (trifluoromethyl) biphenyl to the sulfonyl chloride to the N-methyl pyrrolidone to the nitrating reagent is 1: 1.8:7:3.
Preferably, the alkaline buffer solution is one of a sodium carbonate solution, a sodium bicarbonate solution or a potassium carbonate solution.
Preferably, the alkaline buffer solution is a sodium carbonate solution.
Preferably, the temperature is raised to 35-55 ℃ after the sulfonyl chloride is added.
Preferably, the temperature is raised to 45 ℃ after the sulfonyl chloride is added.
Preferably, the method for adding the nitrating agent in batches at the increased temperature is to add the nitrating agent in 3-5 batches during the increased temperature.
Preferably, the method for adding the nitrating agent in batches at the increased temperature is to add the nitrating agent in 4 batches during the increased temperature.
Preferably, the reflux time of the methanol addition is 0.5-2 hours.
Preferably, the reflux time for adding methanol is 1 hour.
Preferably, the temperature is reduced to-10 ℃ to 0 ℃ after the methanol is added for refluxing.
Preferably, the temperature is reduced to-5 ℃ after the methanol is added for refluxing.
Preferably, the stirring time after adding methanol, refluxing and cooling is 0.5-2 hours.
Preferably, the stirring time after adding methanol for refluxing and cooling is 1 hour.
Compared with the prior art, the preparation method of the 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl has the following advantages: the method for nitrating by adopting ammonium nitrate has the advantages of higher reaction yield, mild reaction conditions, simple post-treatment, good product quality and the like.
Detailed Description
Unless defined otherwise, technical terms used in the following examples have the same meanings as commonly understood by one of ordinary skill in the art to which the present invention belongs. The test reagents used in the following examples, unless otherwise specified, are all conventional biochemical reagents; the experimental methods are conventional methods unless otherwise specified.
The present invention will be described in detail with reference to examples.
Example 1
Adding 14.5g of 2,2 '-bistrifluoromethylbiphenyl and 34.5g N-methylpyrrolidone into a reaction bottle, stirring and dissolving, then dropwise adding 12.1g of sulfonyl chloride, after dropwise adding, heating to about 45 ℃, adding 12g of ammonium nitrate (the molar ratio is 2, 2' -bistrifluoromethylbiphenyl: sulfonyl chloride: N-methylpyrrolidone: ammonium nitrate is 1: 1.8:7: 3) in batches, keeping the temperature for reaction, monitoring the reaction of the raw materials by TLC, slowly adding ice water into the reaction liquid, adjusting the pH to be neutral by using a 5% sodium carbonate solution, taking an oil layer, adding 20 ml of methanol, refluxing for 1 hour, slowly cooling to-5 ℃, stirring for 1 hour, and filtering to obtain 18.7g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid, wherein the yield is 98.42%.
Example 2
Adding 14.5g of 2,2 '-bistrifluoromethylbiphenyl and 25g N-methylpyrrolidone into a reaction bottle, stirring and dissolving, then dropwise adding 9.4g of sulfonyl chloride, heating to about 35 ℃ after dropwise adding is finished, adding 9.6g of ammonium nitrate (the molar ratio is 2, 2' -bistrifluoromethylbiphenyl: sulfonyl chloride: N-methylpyrrolidone: ammonium nitrate is 1: 1.4: 5: 2.5) in batches, keeping the temperature for reaction, monitoring the reaction of the raw materials by TLC, slowly adding ice water into the reaction liquid, adjusting the pH to be neutral by using 5% sodium carbonate solution, taking an oil layer, adding 20 ml of methanol, refluxing for 1 hour, slowly cooling to-5 ℃, stirring for 1 hour, and filtering to obtain 17.3g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid with the yield of 91.05%.
Example 3
Adding 14.5g of 2,2 '-bistrifluoromethylbiphenyl and 44.6g N-methylpyrrolidone into a reaction bottle, stirring and dissolving, then dropwise adding 14.8g of sulfonyl chloride, after dropwise adding, heating to about 50 ℃, adding 14g of ammonium nitrate (the molar ratio is 2, 2' -bistrifluoromethylbiphenyl: sulfonyl chloride: N-methylpyrrolidone: ammonium nitrate is 1: 2.2: 9: 3.5) in batches, keeping the temperature for reaction, after TLC monitors that the raw materials are completely reacted, slowly adding ice water into the reaction liquid, adjusting the pH to be neutral by using 5% sodium carbonate solution, taking an oil layer, adding 20 ml of methanol, refluxing for 1 hour, slowly cooling to-5 ℃, stirring for 1 hour, and filtering to obtain 18.8g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid, wherein the yield is 98.94%.
Example 4
Adding 14.5g of 2,2 '-bistrifluoromethylbiphenyl and 39.6g N-methylpyrrolidone into a reaction bottle, stirring and dissolving, then dropwise adding 10.8g of sulfonyl chloride, heating to about 40 ℃ after dropwise adding, adding 10.8g of ammonium nitrate (the molar ratio is 2, 2' -bistrifluoromethylbiphenyl: sulfonyl chloride: N-methylpyrrolidone: ammonium nitrate is 1: 1.6: 6: 2.7) in batches, keeping the temperature for reaction, monitoring the reaction of the raw materials by TLC, slowly adding ice water into the reaction liquid, adjusting the pH to be neutral by using a 5% sodium carbonate solution, taking an oil layer, adding 20 ml of methanol for refluxing for 1 hour, slowly cooling to-5 ℃, stirring for 1 hour, and filtering to obtain 18.2g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid, wherein the yield is 95.78%.
Example 5
Adding 14.5g of 2,2 '-bistrifluoromethylbiphenyl and 40g N-methylpyrrolidone into a reaction bottle, stirring and dissolving, then dropwise adding 10.8g of sulfonyl chloride, heating to about 40 ℃ after dropwise adding, adding 12.6g of ammonium nitrate (the molar ratio of the 2, 2' -bistrifluoromethylbiphenyl to the sulfonyl chloride to the N-methylpyrrolidone to the potassium nitrate is 1: 1.6: 6: 2.5) in batches, keeping the temperature for reaction, monitoring the reaction of the raw materials by TLC, slowly adding ice water into the reaction liquid, adjusting the pH to be neutral by using a 5% potassium carbonate solution, taking an oil layer, adding 20 ml of methanol, refluxing for 1 hour, slowly cooling to-5 ℃, stirring for 1 hour, and filtering to obtain 15.6g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid with the yield of 82.11%.
Example 6
Adding 14.5g of 2,2 '-bistrifluoromethylbiphenyl and 40g N-methylpyrrolidone into a reaction bottle, stirring and dissolving, then dropwise adding 10.8g of sulfonyl chloride, heating to about 40 ℃ after dropwise adding, adding 10.4g of sodium nitrite (the molar ratio is 2, 2' -bistrifluoromethylbiphenyl: sulfonyl chloride: N-methylpyrrolidone: sodium nitrite is 1: 1.6: 6: 3) in batches, keeping the temperature for reaction, monitoring the reaction completion of raw materials by TLC, slowly adding ice water into a reaction liquid, adjusting the pH to be neutral by using a 5% sodium carbonate solution, taking an oil layer, adding 20 ml of methanol, refluxing for 1 hour, slowly cooling to-5 ℃, stirring for 1 hour, and filtering to obtain 12.9g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid with the yield of 67.89%.
Example 7
14.5g of 2,2 '-bistrifluoromethylbiphenyl and 65g N-methylpyrrolidone are added into a reaction bottle, 10.8g of sulfonyl chloride is dropwise added after stirring and dissolving, after dropwise addition is finished, the temperature is raised to about 40 ℃, 23.3g of copper nitrate (the molar ratio is 2, 2' -bistrifluoromethylbiphenyl: sulfonyl chloride: N-methylpyrrolidone: copper nitrate is 1: 1.6: 13: 2.5) is added in batches, the reaction is kept at the temperature, ice water is slowly added into a reaction liquid after the raw materials are completely reacted by TLC monitoring, 10% sodium bicarbonate solution is used for adjusting the pH to be neutral, an oil layer is taken, 20 ml of methanol is added for refluxing for 1 hour, the temperature is slowly reduced to-5 ℃, stirring is carried out for 1 hour, and then 14.7g of 2,2 '-bistrifluoromethyl-4, 4' -dinitrobiphenyl yellow solid is obtained by filtering, wherein the yield is 77.37%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (14)
1. A preparation method of 2,2 '-bis (trifluoromethyl) -4, 4' -dinitrobiphenyl is characterized by comprising the following steps: the method comprises the following steps: dissolving 2,2 ' -bis (trifluoromethyl) biphenyl serving as a raw material in N-methyl pyrrolidone, dropwise adding sulfonyl chloride at room temperature, heating and adding a nitration reagent in batches after dropwise adding is finished, slowly adding ice water into a reaction liquid to cool to room temperature after the raw material completely reacts, adjusting the pH to be neutral by using an alkaline buffer solution, taking an oil layer, adding methanol for refluxing, slowly cooling, stirring and filtering to obtain 2,2 ' -bis (trifluoromethyl) -4,4 ' -dinitrobiphenyl yellow solid; the nitrating agent is ammonium nitrate; the molar ratio of the 2, 2' -bis (trifluoromethyl) biphenyl, the sulfonyl chloride, the N-methyl pyrrolidone and the nitration reagent is 1: (1.4-2.2): (5-9): (2.5-3.5).
2. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the molar ratio of the 2, 2' -bis (trifluoromethyl) biphenyl, the sulfonyl chloride, the N-methyl pyrrolidone and the nitration reagent is 1: 1.8:7:3.
3. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the alkaline buffer solution is one of a sodium carbonate solution, a sodium bicarbonate solution or a potassium carbonate solution.
4. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the alkaline buffer solution is a sodium carbonate solution.
5. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: and after adding sulfonyl chloride, heating to 35-55 ℃.
6. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: and after adding sulfonyl chloride, heating to 45 ℃.
7. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the method for adding the nitrating reagent in batches by heating comprises the step of adding the nitrating reagent in 3-5 batches in the heating process.
8. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the method for adding the nitrating reagent in batches by heating comprises the step of adding the nitrating reagent in 4 batches in the heating process.
9. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the reflux time of the added methanol is 0.5 to 2 hours.
10. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the reflux time for the addition of methanol was 1 hour.
11. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: adding methanol, refluxing and cooling to-10-0 ℃.
12. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: and adding methanol, refluxing and cooling to the temperature of-5 ℃.
13. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the stirring time after adding methanol for reflux and cooling is 0.5-2 hours.
14. The method for preparing 2,2 '-bis-trifluoromethyl-4, 4' -dinitrobiphenyl according to claim 1, wherein: the stirring time after adding methanol for reflux and cooling is 1 hour.
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