CN108164422A - The production method of o-sec-butyl -4,6- dinitrophenol - Google Patents
The production method of o-sec-butyl -4,6- dinitrophenol Download PDFInfo
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- CN108164422A CN108164422A CN201711459632.4A CN201711459632A CN108164422A CN 108164422 A CN108164422 A CN 108164422A CN 201711459632 A CN201711459632 A CN 201711459632A CN 108164422 A CN108164422 A CN 108164422A
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- sec
- butyl
- sulfuric acid
- acid
- dinitrophenol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of production method of 4,6 dinitrophenol of o-sec-butyl, including step：Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, the composition of half sulfonated liquid is sulfuric acid and o-sec-butyl phenol, and the molar ratio of both sulfuric acid and o-sec-butyl phenol is less than 1, between 0.1 ~ 0.95；Half sulfonated liquid is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid composition again and carries out a step nitration reaction, isolates after waste acid water through neutralizing washing, distillation, obtains 4,6 dinitrophenol of o-sec-butyl.The production method of the present invention increases using waste acid water, reduces spent acid, waste liquid discharging amount and water consumption, reduction production cost.
Description
Technical field
The present invention relates to a kind of production methods of o-sec-butyl -4,6- dinitrophenol, especially a kind of to utilize waste acid water
Life that is more, reducing spent acid wastewater discharge and sulfuric acid dosage, the o-sec-butyl -4,6- dinitrophenol for reducing production cost
Production method.
Background technology
At present, o-sec-butyl -4,6- dinitrophenol（DNBP）Production method be with o-sec-butyl phenol, excessive sulphur
Acid for raw material carry out sulfonating reaction generate sulfonated liquid, by sulfonated liquid be added drop-wise in prepared nitration mixture solution into
One step of row nitrify, after obtained nitrification liquid finally is isolated waste acid water, it is neutralized, washing and distillation obtain o-sec-butyl-
4,6- dinitrophenol.Now using the technology of the complete sulfonation of o-sec-butyl phenol, sulfuric acid and o-sec-butyl in production
The molar ratio of phenol is 1.2-1.4:1.The purpose of sulfonation is that disproportionated reaction occurs in order to protect o-sec-butyl phenol not oxidized.
The spent acid water section separated returns to configuration mixed acid solution, and to maintain the sulfuric acid content in nitration mixture, another part removes spent acid
Processing.In even running, the sulfuric acid that sulfonation adds in will all go spent acid to handle, and the treating capacity for leading to waste acid water in this way is big, processing
Cost increases, and the spent acid water returned is few, and the material taken away is more.
Invention content
Present invention aim to address the deficiencies of above-mentioned technology, provide a kind of reduction waste acid water treating capacity, reduce waste acid water
Discharge capacity and water consumption, reduce production cost o-sec-butyl -4,6- dinitrophenol production method.
In order to solve the above technical problems, the present invention provides a kind of production method of o-sec-butyl -4,6- dinitrophenol,
Including step：
Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, the composition of half sulfonated liquid is
The molar ratio of both sulfuric acid and o-sec-butyl phenol, sulfuric acid and o-sec-butyl phenol is less than 1, between 0.1 ~ 0.95；
Half sulfonated liquid is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid composition again and carries out a step nitration reaction, is isolated useless
Through neutralizing washing, distillation after sour water, o-sec-butyl -4,6- dinitrophenol is obtained.
Preferably, the water that mass ratio is 5 ~ 15% is added in half sulfonated liquid.
Preferably, sulfuric acid mass fraction is 20% in the nitration mixture.
The production method of the present invention increases using waste acid water, reduces spent acid, waste liquid discharging amount and water consumption, reduction product
Production cost.
Compared with prior art, the production method of o-sec-butyl -4,6- dinitrophenol of the present invention, reached as
Lower effect：
Half sulfonation technology of maximum difference of the present invention and the prior art, are to be less than o-sec-butyl phenol molal quantity using molal quantity
Sulfuric acid carries out sulfonating reaction with o-sec-butyl phenol and prepares half sulfonated liquid, has the following advantages that：
1. reducing the inventory of sulfuric acid in sulfonation process, accordingly reduce the production quantity for generating waste acid water, while reduce useless
The processing cost of sour water, realizes energy-saving and emission-reduction；
2. returning to the spent acid water with nitration mixture to increase, reduce the dosage of water, also reduce cost for wastewater treatment due to returning to
Spent acid water increase, the material that corresponding waste acid water is taken home also increases, yield slightly improve, about 1%；
3. using half sulfonation technology on o-sec-butyl -4,6- dinitrophenol product qualities without influence；
4. half sulfonation reduces the addition of sulfuric acid, make sulfonating reaction therein mild, operation is safer.
Specific embodiment
Some vocabulary has such as been used to censure specific components in specification and claim.Those skilled in the art should
It is understood that hardware manufacturer may call same component with different nouns.This specification and claims are not with name
The difference of title is used as the mode for distinguishing component, but is used as the criterion of differentiation with the difference of component functionally.Such as logical
The "comprising" of piece specification and claim mentioned in is an open language, therefore should be construed to " include but do not limit
In "." substantially " refer in receivable error range, those skilled in the art can be described within a certain error range solution
Technical problem basically reaches the technique effect.Specification subsequent descriptions are to implement the better embodiment of the present invention, so described
Description is for the purpose of illustrating the rule of the present invention, is not limited to the scope of the present invention.Protection scope of the present invention
When subject to appended claims institute defender.
Embodiment 1：
The production method of o-sec-butyl -4,6- dinitrophenol of the present invention is divided into two steps：
Step 1）：Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, half sulfonated liquid
It forms as sulfuric acid and o-sec-butyl phenol, the molar ratio of both sulfuric acid and o-sec-butyl phenol is less than 1, the molar ratio of the present embodiment
It is 0.1；
5 ~ 15% water can also be added in the sulfonated liquid（Mass ratio）.
Half sulfonation process first can add sulfuric acid to add o-sec-butyl phenol again, also first o-sec-butyl phenol can be added to add sulfuric acid again,
Also the two can be added in reactor simultaneously, the speed added can quickly, and moment can also.
Step 2）：Half sulfonated liquid obtained in step 1 is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid and carries out a step nitre
Change reaction, isolate after spent acid through washing, distilling to obtain o-sec-butyl -4,6- dinitrophenol.
Preferably, sulfuric acid mass fraction is 20% in the nitration mixture.
Step 2）The processes such as middle nitration reaction, separation, washing, distillation use the technique of the prior art, do not do have here
Body limits.
The present invention adds a step nitrification technology the same with present sulfonation, using quantitative o-sec-butyl phenol, sulfuric acid as raw material
It carries out sulfonating reaction and generates half sulfonated liquid, can also suitably add water in half sulfonated liquid；Half sulfonated liquid is added drop-wise to sulfuric acid and nitric acid
Mixed acid solution in carry out a step nitration reaction, isolate after waste acid water through neutralizing, washing and distillation obtains o-sec-butyl -4,6-
Dinitrophenol.With the prior art except that proportion scale in sulfonation process, since the addition of sulfuric acid does not reach
The amount of o-sec-butyl phenol whole sulfonation, o-sec-butyl phenol are partly sulfonated, therefore referred to as half sulfonation, and the ratio of sulfonation is 10
~ 95%, other processes are identical.
Embodiment 2：
The production method of o-sec-butyl -4,6- dinitrophenol of the present invention is divided into two steps：
Step 1）：Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, half sulfonated liquid
It forms as sulfuric acid and o-sec-butyl phenol, the molar ratio of both sulfuric acid and o-sec-butyl phenol is less than 1, molar ratio in the present embodiment
It is 0.95；
5 ~ 15% water can also be added in the sulfonated liquid（Mass ratio）.
Half sulfonation process first can add sulfuric acid to add o-sec-butyl phenol again, also first o-sec-butyl phenol can be added to add sulfuric acid again,
Also the two can be added in reactor simultaneously, the speed added can quickly, and moment can also.
Step 2）：Half sulfonated liquid obtained in step 1 is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid and carries out a step nitre
Change reaction, isolate after spent acid through washing, distilling to obtain o-sec-butyl -4,6- dinitrophenol.
Preferably, sulfuric acid mass fraction is 20% in the nitration mixture.
Step 2）The processes such as middle nitration reaction, separation, washing, distillation use the technique of the prior art, do not do have here
Body limits.
Embodiment 3：
The production method of o-sec-butyl -4,6- dinitrophenol of the present invention is divided into two steps：
Step 1）：Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, half sulfonated liquid
It forms as sulfuric acid and o-sec-butyl phenol, the molar ratio of both sulfuric acid and o-sec-butyl phenol is less than 1, molar ratio in the present embodiment
It is 0.5；
The water that mass fraction is 5 ~ 15% can also be added in the sulfonated liquid.
Half sulfonation process first can add sulfuric acid to add o-sec-butyl phenol again, also first o-sec-butyl phenol can be added to add sulfuric acid again,
Also the two can be added in reactor simultaneously, the speed added can quickly, and moment can also.
Step 2）：Half sulfonated liquid obtained in step 1 is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid and carries out a step nitre
Change reaction, isolate after spent acid through washing, distilling to obtain o-sec-butyl -4,6- dinitrophenol.
Preferably, sulfuric acid mass fraction is 20% in the nitration mixture.
Step 2）The processes such as middle nitration reaction, separation, washing, distillation use the technique of the prior art, do not do have here
Body limits.
Embodiment 4：
The production method of o-sec-butyl -4,6- dinitrophenol of the present invention is divided into two steps：
Step 1）：Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, half sulfonated liquid
It forms as sulfuric acid and o-sec-butyl phenol, the molar ratio of both sulfuric acid and o-sec-butyl phenol is in the present embodiment less than 1
0.72；
5 ~ 15% water can also be added in the sulfonated liquid（Mass ratio）.
Half sulfonation process first can add sulfuric acid to add o-sec-butyl phenol again, also first o-sec-butyl phenol can be added to add sulfuric acid again,
Also the two can be added in reactor simultaneously, the speed added can quickly, and moment can also.
Step 2）：Half sulfonated liquid obtained in step 1 is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid and carries out a step nitre
Change reaction, isolate after spent acid through washing, distilling to obtain o-sec-butyl -4,6- dinitrophenol.
Sulfuric acid mass fraction is 20% in the nitration mixture.
Step 2）The processes such as middle nitration reaction, separation, washing, distillation use the technique of the prior art, do not do have here
Body limits.
O-sec-butyl -4,6- dinitrophenol the product contents of technological process production in embodiment 2 are more than or equal to
98.5%, while greatly reduce the processing cost of waste acid water and waste water.
Several preferred embodiments of the present invention have shown and described in above description, but as previously described, it should be understood that the present invention
Be not limited to form disclosed herein, be not to be taken as the exclusion to other embodiment, and available for various other combinations,
Modification and environment, and the above teachings or related fields of technology or knowledge can be passed through in the scope of the invention is set forth herein
It is modified.And changes and modifications made by those skilled in the art do not depart from the spirit and scope of the present invention, then it all should be in this hair
In the protection domain of bright appended claims.
Claims (3)
1. a kind of production method of o-sec-butyl -4,6- dinitrophenol, which is characterized in that including step：
Half sulfonating reaction is carried out as raw material using o-sec-butyl phenol, sulfuric acid and generates half sulfonated liquid, the composition of half sulfonated liquid is
The molar ratio of both sulfuric acid and o-sec-butyl phenol, sulfuric acid and o-sec-butyl phenol is less than 1, between 0.1 ~ 0.95；
Half sulfonated liquid is added drop-wise in the mixed acid solution of sulfuric acid and nitric acid composition again and carries out a step nitration reaction, is isolated useless
Through neutralizing washing, distillation after sour water, o-sec-butyl -4,6- dinitrophenol is obtained.
2. the production method of o-sec-butyl -4,6- dinitrophenol according to claim 1, which is characterized in that described half
The water that mass ratio is 5 ~ 15% is added in sulfonated liquid.
3. the production method of o-sec-butyl -4,6- dinitrophenol according to claim 1, which is characterized in that described mixed
Sulfuric acid mass fraction is 20% in acid.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711459632.4A CN108164422A (en) | 2017-12-28 | 2017-12-28 | The production method of o-sec-butyl -4,6- dinitrophenol |
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| CN201711459632.4A CN108164422A (en) | 2017-12-28 | 2017-12-28 | The production method of o-sec-butyl -4,6- dinitrophenol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110015961A (en) * | 2019-04-19 | 2019-07-16 | 大连理工大学 | A method of preparation 2,4- dinitro -6- sec-butyl phenol is nitrified using waste nitric acid |
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| US4439374A (en) * | 1982-06-28 | 1984-03-27 | Ethyl Corporation | Process for sulfonating impure ortho alkylphenol |
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Cited By (1)
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|---|---|---|---|---|
| CN110015961A (en) * | 2019-04-19 | 2019-07-16 | 大连理工大学 | A method of preparation 2,4- dinitro -6- sec-butyl phenol is nitrified using waste nitric acid |
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