CN102391126A - Method for producing 2, 4-dinitrobenzene methyl ether and 2, 4- dinitrophenol simultaneously - Google Patents

Method for producing 2, 4-dinitrobenzene methyl ether and 2, 4- dinitrophenol simultaneously Download PDF

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Publication number
CN102391126A
CN102391126A CN2011103146270A CN201110314627A CN102391126A CN 102391126 A CN102391126 A CN 102391126A CN 2011103146270 A CN2011103146270 A CN 2011103146270A CN 201110314627 A CN201110314627 A CN 201110314627A CN 102391126 A CN102391126 A CN 102391126A
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China
Prior art keywords
methyl ether
dinitrophenol
dinitrobenzene
dinitrobenzene methyl
reaction
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CN2011103146270A
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Chinese (zh)
Inventor
付忠东
高建伟
解德水
万克玲
梁足培
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SHANDONG CHANGYI ZAOHU YANHUA Co Ltd
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SHANDONG CHANGYI ZAOHU YANHUA Co Ltd
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Priority to CN2011103146270A priority Critical patent/CN102391126A/en
Publication of CN102391126A publication Critical patent/CN102391126A/en
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Abstract

The invention discloses a method for producing 2, 4- dinitrobenzene methyl ether and 2, 4-dinitrophenol simultaneously, which is characterized by comprising the following steps: feeding and reacting stage: adding methanol and 2, 4- dinitro chloro benzene into a reaction device, heating until the 2, 4- dinitro chloro benzene is complately dissolved, and dripping sodium hydroxide water solution for reaction, so as to obtain the mixture of 2, 4- dinitrobenzene methyl ether and 2, 4- dinitrophenol; extracting 2, 4- dinitrobenzene methyl ether; obtaining methanol through steaming after reaction, adding water, regulating pH, lowering the temperature and suction filtering, washing a filter cake through water, and then drying, so as to obtain 2, 4- dinitrobenzene methyl ether; and extracting 2, 4- dinitrophenol; regulating the pH value of obtained filter liquor, cooling and crystallizing, washing through water, filtering, and drying so as to obtain 2, 4- dinitrophenol. The process is simple, the reaction time is short, the efficiency is high, the use level of the methanol can be effectively reduced, and the toxicity is lowered.

Description

A kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol
Technical field
The present invention relates to chemical technology field, relate in particular to and a kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol.
Background technology
2,4-dinitrobenzene methyl ether and 2,2, 4-dinitrophenol are the midbodys of preparation dyestuff and medicine etc., present Synthetic 2, and there is inferior position in 4-dinitrobenzene methyl ether: the consumption of solvent methanol is big, generally is 2,15~20 times of 4-DNCB molar weight; Reaction times reaches 10 hours; Processing condition are harsh, and operation easier is big.
Summary of the invention
Technical problem to be solved by this invention provides that a kind of technology is simple, the solvent methanol consumption is few, produce 2 when the reaction times is short, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol.
For solving the problems of the technologies described above, technical scheme of the present invention is: a kind ofly produce 2 simultaneously, and 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol comprises step:
1) the charging reaction stage:
With methyl alcohol and 2, the 4-DNCB adds reaction unit, is heated to 2, and the 4-DNCB dissolves entirely, and behind the dropping sodium aqueous solution, reaction obtains 2,4-dinitrobenzene methyl ether and 2, the mixture of 2, 4-dinitrophenol;
2) extract 2,4-dinitrobenzene methyl ether:
Steam methyl alcohol after reaction finishes, add entry, regulate pH, cooling, suction filtration, filter cake is used water washing, and drying gets 2,4-dinitrobenzene methyl ether;
3) extract 2,2, 4-dinitrophenol:
Above-mentioned suction filtration gained filtrating is regulated the pH value, cooling, water washing is used in crystallization, filters, and drying gets 2,2, 4-dinitrophenol.
As optimized technical scheme, in the said charging reaction stage step, 2; The mol ratio of 4-DNCB, methyl alcohol and sodium hydroxide is 1:3 ~ 8:1.05; The mass concentration of aqueous sodium hydroxide solution is 10 ~ 40%, and temperature of reaction is 56 ~ 70 ℃, and the reaction times is 2 ~ 5 hours.
As optimized technical scheme, said extraction 2, in the 4-dinitrobenzene methyl ether step, functional quality concentration is that 30% sodium hydroxide solution adjusting pH is 8~10.
As improvement to above-mentioned technology, said extraction 2, using pH in the 4-dinitrobenzene methyl ether step behind the suction filtration is that 8~10 aqueous sodium hydroxide washes is washed 2~3 times, and then to be washed with water to pH be 7.
As the improvement to technique scheme, said extraction 2 steams Methanol Recovery described in the 4-dinitrobenzene methyl ether step and applies mechanically, and economizes in raw materials, and has reduced cost.
Said extraction 2,4-dinitrobenzene methyl ether step obtain 2,4-dinitrobenzene methyl ether yield is 45~80%.
As optimized technical scheme, said extraction 2, adjusting pH value functional quality concentration is that 10~35% hydrochloric acid adjusting pH is 2.5~4.5 in the 2, 4-dinitrophenol step, and 5 ~ 30 ℃ of coolings down, crystallization 1 ~ 3 hour is filtered, and it is 7 that filter cake is washed with water to pH.
Said extraction 2, obtain in the 2, 4-dinitrophenol step 2, the 2, 4-dinitrophenol yield is 17~53%.
Owing to adopted technique scheme, a kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol; It is characterized in that, comprise step: the charging reaction stage: with methyl alcohol and 2, the 4-DNCB adds reaction unit, is heated to 2; The 4-DNCB dissolves entirely, behind the dropping sodium aqueous solution, and reaction; Obtain 2,4-dinitrobenzene methyl ether and 2, the mixture of 2, 4-dinitrophenol; Extract 2,4-dinitrobenzene methyl ether: steam methyl alcohol after reaction finishes, add entry, regulate pH, cooling, suction filtration, filter cake is used water washing, and drying gets 2,4-dinitrobenzene methyl ether; Extraction 2,2, 4-dinitrophenol: above-mentioned gained filtrating is regulated the pH value, cooling, water washing is used in crystallization, filters, and drying gets 2,2, 4-dinitrophenol, technology is simple, the reaction times is short, and efficient is high, and has reduced the consumption of methyl alcohol effectively, has reduced toxicity.
Embodiment
Below in conjunction with embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in the restriction scope of the present invention.Should be understood that in addition those skilled in the art can do various changes or modification to the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment one:
In reaction flask, add methyl alcohol 9.6g (0.3 mol) successively, 2,4-DNCB 20.3 g (0.1 mol) are heated to 2, and the 4-DNCB dissolves entirely; Open and stir, the dropping mass concentration is 10% sodium hydroxide solution 14 g (molar weight of sodium hydroxide is 0.105 mol) in 5~10 min, continues to be heated to backflow, under 70 ℃; React after 2 hours, steam methyl alcohol, add 6 mL water then, using mass concentration is that to transfer pH be 8~10 for 10% sodium hydroxide solution; Reduce to room temperature, filter, using pH is that 8~10 aqueous sodium hydroxide washes is washed merging filtrate and washing lotion 2 times; It is 7 to pH that filter cake uses cold water washing again, and drying gets 2,4-dinitrobenzene methyl ether 8.9g; With 2,4-DNCB meter, yield are 45%, and fusing point is 93~95 ℃.
Above-mentioned filtrating use mass concentration be 10% hydrochloric acid to transfer pH be 2.5~4.5, be cooled to 20 ℃, crystallization 1 hour is filtered; Cold water washing is 7 to pH, and drying gets 2,2, 4-dinitrophenol 9.6 g; With 2,4-DNCB meter, yield are 53%, and fusing point is 112~114 ℃.
Embodiment two:
In reaction flask, add methyl alcohol 16g (0.5 mol) successively, 2,4-DNCB 20.3 g (0.1 mol) are heated to 2, and the 4-DNCB dissolves entirely; Open and stir, the dropping mass concentration is 30% sodium hydroxide solution 42 g (molar weight of sodium hydroxide is 0.105 mol) in 5~10 min, continues to be heated to backflow, under 62 ℃; React after 3 hours, steam methyl alcohol, add 20 mL water then, using 30% sodium hydroxide solution to transfer pH is 8~10; Reduce to room temperature, filter, using pH is that 8~10 aqueous sodium hydroxide washes is washed merging filtrate and washing lotion 2 times; It is 7 to pH that filter cake uses cold water washing again, and drying gets 2,4-dinitrobenzene methyl ether 8.9g; With 2,4-DNCB meter, yield are 60.6%, and fusing point is 93~95 ℃.
Above-mentioned filtrating use mass concentration be 20% hydrochloric acid to transfer pH be 2.5~3.5, be cooled to 5 ℃, crystallization 1 hour is filtered; Cold water washing is 7 to pH, and drying gets 2,2, 4-dinitrophenol 6.7 g; With 2,4-DNCB meter, yield are 36.4%, and fusing point is 112~114 ℃.
Embodiment three:
In reaction flask, add methyl alcohol 25.6g (0.8 mol) successively, 2,4-DNCB 20.3 g (0.1 mol) are heated to 2, and the 4-DNCB dissolves entirely; Open and stir, drip 40% sodium hydroxide solution, 10.5 g (molar weight of sodium hydroxide is 0.105 mol) in 5~10 min, continue to be heated to backflow, under 56 ℃; React after 5 hours, steam methyl alcohol, add 24 mL water then, using 30% sodium hydroxide solution to transfer pH is 8~10; Reduce to room temperature, filter, using pH is that 8~10 aqueous sodium hydroxide washes is washed merging filtrate and washing lotion 3 times; It is 7 to pH that filter cake uses cold water washing again, and drying gets 2,4-dinitrobenzene methyl ether 15.8 g; With 2,4-DNCB meter, yield are 80%, and fusing point is 93~95 ℃.
Above-mentioned filtrating use mass concentration be 35% hydrochloric acid to transfer pH be 2.5~4.5, be cooled to 10 ℃, crystallization 1 hour is filtered; Cold water washing is 7 to pH, and drying gets 2,2, 4-dinitrophenol 3.2g; With 2,4-DNCB meter, yield are 17%, and fusing point is 112~114 ℃.
More than show and described ultimate principle of the present invention, principal character and advantage of the present invention.The technician of the industry should understand; The present invention is not restricted to the described embodiments; That describes in the foregoing description and the specification sheets just explains principle of the present invention; Under the prerequisite that does not break away from spirit and scope of the invention, the present invention also has various changes and modifications, and these variations and improvement all fall in the scope of the invention that requires protection.The present invention requires protection domain to be defined by appending claims and equivalent thereof.
All are from design of the present invention, and the structural transformation of having done without creative work all drops within protection scope of the present invention.

Claims (8)

1. produce 2 simultaneously for one kind, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol is characterized in that, comprises step:
1) the charging reaction stage:
With methyl alcohol and 2, the 4-DNCB adds reaction unit, is heated to 2, and the 4-DNCB dissolves entirely, and behind the dropping sodium aqueous solution, reaction obtains 2,4-dinitrobenzene methyl ether and 2, the mixture of 2, 4-dinitrophenol;
2) extract 2,4-dinitrobenzene methyl ether:
Steam methyl alcohol after reaction finishes, add entry, regulate pH, cooling, suction filtration, filter cake is used water washing, and drying gets 2,4-dinitrobenzene methyl ether;
3) extract 2,2, 4-dinitrophenol:
Above-mentioned suction filtration gained filtrating is regulated the pH value, cooling, water washing is used in crystallization, filters, and drying gets 2,2, 4-dinitrophenol.
2. as claimed in claim 1ly a kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol; It is characterized in that: in the said charging reaction stage step; 2, the mol ratio of 4-DNCB, methyl alcohol and sodium hydroxide is 1:3 ~ 8:1.05, and the mass concentration of aqueous sodium hydroxide solution is 10 ~ 40%; Temperature of reaction is 56 ~ 70 ℃, and the reaction times is 2 ~ 5 hours.
3. as claimed in claim 1ly a kind ofly produce 2 simultaneously; 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol is characterized in that: said extraction 2; In the 4-dinitrobenzene methyl ether step, functional quality concentration is that 10 ~ 40% sodium hydroxide solutions adjusting pH is 8~10.
4. as claimed in claim 1ly a kind ofly produce 2 simultaneously; 4-dinitrobenzene methyl ether and 2; The method of 2, 4-dinitrophenol; It is characterized in that: said extraction 2, using pH in the 4-dinitrobenzene methyl ether step behind the suction filtration is that 8~10 aqueous sodium hydroxide washes is washed 2~3 times, and then to be washed with water to pH be 7.
5. describedly a kind ofly produce 2 simultaneously like claim 3 or 4,4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol is characterized in that: said extraction 2,4-dinitrobenzene methyl ether step obtain 2,4-dinitrobenzene methyl ether yield is 45~80%.
6. as claimed in claim 1ly a kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol is characterized in that: said extraction 2 steams Methanol Recovery described in the 4-dinitrobenzene methyl ether step and applies mechanically.
7. as claimed in claim 1ly a kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol; It is characterized in that: said extraction 2; Functional quality concentration is that 10~35% hydrochloric acid adjusting pH is 2.5~4.5 in the 2, 4-dinitrophenol step, in 5 ~ 30 ℃ of coolings down, crystallization 1 ~ 3 hour; Filter, it is 7 that the gained filter cake is washed with water to pH.
8. as claimed in claim 7ly a kind ofly produce 2 simultaneously, 4-dinitrobenzene methyl ether and 2, the method for 2, 4-dinitrophenol is characterized in that: said extraction 2, obtain in the 2, 4-dinitrophenol step 2, the 2, 4-dinitrophenol yield is 17~53%.
CN2011103146270A 2011-10-17 2011-10-17 Method for producing 2, 4-dinitrobenzene methyl ether and 2, 4- dinitrophenol simultaneously Pending CN102391126A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103396318A (en) * 2013-07-30 2013-11-20 浙江迪邦化工有限公司 Synthetic process for 2,4-dinitroanisole
CN105777550A (en) * 2016-05-13 2016-07-20 湖北东方化工有限公司 Method for continuously synthesizing 2,4-dimitroanisole
CN108947845A (en) * 2018-08-28 2018-12-07 山西津津化工有限公司 A kind of production method of 2,4-dinitrophenol sodium

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CN1146450A (en) * 1995-09-29 1997-04-02 陈陆武 Technological process for preparation of 2-amino-4- acetaminoanisole by 2,4-dinitro chlorobenzene
CN1354167A (en) * 2000-11-17 2002-06-19 中国石油天然气股份有限公司 Method for preparing ortho-(p-) nitrobenzenealkyl ether
CN1583713A (en) * 2004-06-14 2005-02-23 上海市合成树脂研究所 Producing procedure of 3,4'-diamino diphenyl ether

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US3283011A (en) * 1962-02-21 1966-11-01 Universal Oil Prod Co Preparation of nitrophenols
CN1146450A (en) * 1995-09-29 1997-04-02 陈陆武 Technological process for preparation of 2-amino-4- acetaminoanisole by 2,4-dinitro chlorobenzene
CN1354167A (en) * 2000-11-17 2002-06-19 中国石油天然气股份有限公司 Method for preparing ortho-(p-) nitrobenzenealkyl ether
CN1583713A (en) * 2004-06-14 2005-02-23 上海市合成树脂研究所 Producing procedure of 3,4'-diamino diphenyl ether

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Title
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103396318A (en) * 2013-07-30 2013-11-20 浙江迪邦化工有限公司 Synthetic process for 2,4-dinitroanisole
CN105777550A (en) * 2016-05-13 2016-07-20 湖北东方化工有限公司 Method for continuously synthesizing 2,4-dimitroanisole
CN105777550B (en) * 2016-05-13 2019-01-15 湖北东方化工有限公司 The method that one kind being continuously synthesizing to 2,4- dinitroanisol
CN108947845A (en) * 2018-08-28 2018-12-07 山西津津化工有限公司 A kind of production method of 2,4-dinitrophenol sodium

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