CN105439912A - Preparation method of N-phenyl-1- naphthylamino-8-sulfonic acid - Google Patents
Preparation method of N-phenyl-1- naphthylamino-8-sulfonic acid Download PDFInfo
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- CN105439912A CN105439912A CN201510985284.9A CN201510985284A CN105439912A CN 105439912 A CN105439912 A CN 105439912A CN 201510985284 A CN201510985284 A CN 201510985284A CN 105439912 A CN105439912 A CN 105439912A
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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
- C07C303/22—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 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl 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
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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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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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
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of N-phenyl-1- naphthylamino-8-sulfonic acid, which comprises the following steps: 1. condensation: adding aniline into a pot, starting stirring, adding concentrated sulfuric acid, adding 1-naphthylamino-8-sulfonic acid, dehydrating, and condensing at 155+/-2 DEG C; 2. neutralization: adding a soda ash solution to perform neutralization, transferring into a neutralization pot, and regulating the material of the material to 9-11; 3. vapor distillation: regulating the volume of the material with aniline water, adding vat powder to perform vapor distillation, and carrying out extraction when the aniline content in the solution is less than 3+/-0.5%, wherein the aniline content of 2-4% in the solution is used as the switch point; 4. decolorization: starting stirring, regulating the pH value of the liquid to 6.5-7.0, adding activated carbon, and heating to 94-95 DEG C; and 5. acid precipitation: adding dilute sulfuric acid until the residual acid content of the acid precipitation solution is 1.8-2.0%, cooling, discharging to obtain the N-phenyl-1- naphthylamino-8-sulfonic acid, and washing with 1.0-2.0% acid water twice.
Description
Technical field
The present invention relates to a kind of preparation method of N-phenyl-peri acid, belong to the compounds process for production thereof technical field in organic synthesis.
Background technology
N-phenyl-peri acid is a kind of important industrial chemicals for the synthesis of silk goods and cotton products dyestuff, is mainly used in the intermediate as matching stain, is specifically used for producing Weakly Acid Black BR, Weakly Acid Blue 5R and thioxine dyes and azoic dyestuff.
The preparation method of N-phenyl-peri acid is primarily of the condensation and obtaining in sulphuric acid soln of aniline and naphthalidine-8-sulfonic acid, and the underpressure distillation of condensation reaction thing is refined, and can obtain N-phenyl-peri acid; And then N-phenyl-peri acid and soda ash are reacted, wet distillation, activated carbon decolorizing, obtain N-phenyl-peri acid product.
But in the prior art, only just describe the preparation method path of N-phenyl-peri acid, in actual industrial production, still have many processing parameters to need refinement and perfect, otherwise the N-phenyl-peri acid purity prepared is difficult to meet market demands, the method without Optimizing Process Parameters prepares the yield of N-phenyl-peri acid and cost is also difficult to possess competitive power.
Summary of the invention
The present invention is just for the deficiency that prior art exists, a kind of preparation method of N-phenyl-peri acid is provided, can prepare by suitability for industrialized production the N-phenyl-peri acid product meeting market demands, and the preparation of industrialization cost of N-phenyl-peri acid is low.
For solving the problem, the technical solution used in the present invention is as follows:
A preparation method for N-phenyl-peri acid, comprises the following steps:
Step one, condensation: add in pot by the aniline of 78 ~ 80 mass parts, add the vitriol oil that 145 ~ 150 mass parts concentration are greater than 98%, then add the naphthalidine-8-sulfonic acid of 100 mass parts, be then warming up to 120 ~ 130 DEG C, carry out normal pressure dehydration after starting stirring; Then continue to be warming up to 155 ± 2 DEG C, maintain 10 ~ 12 hours, sampling analysis, when naphthalidine-8-sulfonic acid mass concentration is less than or equal to 0.6%, condensation reaction terminates, obtained condensation material;
Step 2, neutralization: in the condensation material that step one is obtained, add soda ash solution neutralize, then go in neutralization pot, adjust material pH value to be 9 ~ 11, in obtained and material;
Step 3, steam distillation: by aniline water adjustment volume of material, the powder that takes a policy carries out steam distillation, and in solution, aniline content is switching point 2 ~ 4%, and less than 3 ± 0.5% extract, obtained thick mother liquor; Until distillation aniline content is lower than 0.3%; In still-process, pH value will remain on more than 9.0;
Step 4, decolouring: start and stir, dilute sulphuric acid is added in the thick mother liquor that step 3 is obtained, adjustment material liquid pH to 6.5 ~ 7.0, add gac afterwards and be warming up to 94 ~ 95 DEG C, be incubated and within 1 ~ 2 hour, do the test of profit circle, make color and luster to green, otherwise add gac, decolour qualified after, by feed liquid filtered while hot, obtained decolouring mother liquor;
Step 5, acid out: the decolouring mother liquor that step 4 is obtained is squeezed in acid out pot, is controlled by temperature of charge at 48 ~ 52 DEG C, adds the dilute sulphuric acid that mass concentration is 28 ~ 32%; The remaining acid content of acid out liquid is made to be 1.8 ~ 2.0%; When being then cooled to below 35 DEG C, discharging obtains N-phenyl-peri acid; After discharging terminates, preparation mass concentration be 1.0 ~ 2.0% sour water N-phenyl-peri acid is washed twice.
As the improvement of technique scheme, in described step one, after dehydration terminates, volume of material in pot is measured, if lower than normal volume, then adds aniline.Normal volume of the present invention refers to the aniline of 78 ~ 80 mass parts, 145 ~ 150 mass parts concentration are greater than the vitriol oil of 98% and the naphthalidine-8-sulfonic acid of 100 mass parts, rejects wherein contained water, the theoretical volume under measuring tempeature.
In actual production, even find under the condition of fixed feeding area ratio, also there is larger fluctuating range in the yield of N-phenyl-peri acid and purity, known by long-term observation and summary, the loss of aniline when major influence factors is that normal pressure dewaters, therefore above-mentioned improvement makes the yield of the preparation method of N-phenyl-peri acid and purity more stable.
As the improvement of technique scheme, after described step one terminates, and also comprised vacuum distilling step before described step 2: start and stir, open vacuum and carry out underpressure distillation, recovery part aniline.Above-mentioned improvement is mainly used in N-phenyl-peri acid preparation process, reduces the cost depletions of aniline.
Compared with prior art, implementation result of the present invention is as follows in the present invention:
The preparation method of N-phenyl-peri acid of the present invention, the N-phenyl-peri acid product meeting market demands can be prepared by suitability for industrialized production, and the preparation of industrialization cost of N-phenyl-peri acid is low, the N-phenyl-peri acid yield prepared is 93 ~ 95%, and purity is 96 ~ 98%; And preparation method's product yield of N-phenyl-peri acid of the present invention and purity are stablized, and fluctuate little, are easy to Mass Control.
Accompanying drawing explanation
The reaction formula of the main chemical reactions of Fig. 1 involved by condensation step of the present invention;
The reaction formula of the main chemical reactions of Fig. 2 involved by neutralization procedure of the present invention;
The reaction formula of the main chemical reactions of Fig. 3 involved by acid out step of the present invention.
Embodiment
Below in conjunction with specific embodiments content of the present invention is described.
specific embodiment 1
The preparation method of the N-phenyl-peri acid described in the present embodiment, comprises the following steps:
(1) condensation: the reaction formula of involved main chemical reactions as shown in Figure 1.
Add in pot by the aniline of the 234kg got ready in scale tank, startup agitator adds the vitriol oil that 450kg concentration is greater than 98%, and when without hydrojet, the naphthalidine-8-sulfonic acid adding 300kg continues to heat up, and carries out normal pressure dehydration.
When material temperature reaches 120 ~ 130 DEG C, dehydration terminates, and measures, if lower than normal volume, then add aniline to volume of material in pot.
Continue to be warming up to 155 ± 2 DEG C, then maintain 10 ~ 12 hours, sampling analysis, naphthalidine-8-sulfonic acid content≤0.6% is qualified, and qualified rear discharging is to vacuum still, otherwise prolongation is held time.
(2) vacuum distilling:
After vacuum distilling charging terminates, start and stir, open vacuum and carry out underpressure distillation, recovery part aniline.
(3) neutralize: the reaction formula of involved main chemical reactions as shown in Figure 2.
After vacuum distilling terminates, add soda ash solution and neutralize, then go in neutralization pot, adjust material pH value to be 9 ~ 11.
(4) steam distillation:
By aniline water adjustment volume of material, the powder that takes a policy carries out steam distillation, and in solution, aniline content is switching point 2 ~ 4%, and less than 3 ± 0.5% extract.
Until distillation aniline content is lower than 0.3%.
In still-process, pH value will remain on more than 9.0.
If the steam distillation time more than 16 hours, then will add vat powder.
(5) decolour:
Start stir, add dilute sulphuric acid, adjustment material liquid pH to 6.5 ~ 7.0, add gac afterwards and be warming up to 94 ~ 95 DEG C, be incubated within 1 ~ 2 hour, do profit circle test, make color and luster to green, otherwise add gac, decolour qualified after, by feed liquid filtered while hot.
(6) acid out: the reaction formula of involved main chemical reactions as shown in Figure 3.
Destainer is evenly squeezed in two acid out pots, temperature of charge is controlled at 48 ~ 52 DEG C, add the dilute sulphuric acid that mass concentration is 28 ~ 32%.
Make the remaining acid content of acid out liquid 1.8 ~ 2.0% for qualified, otherwise add dilute sulphuric acid, until qualified.
Discharging when being cooled to after acid out is qualified below 35 DEG C, prepares the sour water of about the 3000L of 1.0 ~ 2.0% respectively in two acid out pots after discharging terminates, put into suction filter wash-in material.
After acid out discharging, take out mother liquor, drain rear use 1% diluted acid water washing finished product twice, after washing terminates, centrifugal dress bag.
The N-phenyl-peri acid that the present embodiment prepares, its yield is 95%, and purity is 96%.
specific embodiment 2
The preparation method of the N-phenyl-peri acid described in the present embodiment, comprises the following steps:
(1) condensation: the reaction formula of involved main chemical reactions as shown in Figure 1.
Add in pot by the aniline of the 240kg got ready in scale tank, startup agitator adds the vitriol oil that 435kg concentration is greater than 98%, and when without hydrojet, the naphthalidine-8-sulfonic acid adding 300kg continues to heat up, and carries out normal pressure dehydration.
When material temperature reaches 120 ~ 130 DEG C, dehydration terminates, and measures, if lower than normal volume, then add aniline to volume of material in pot.
Continue to be warming up to 155 ± 2 DEG C, then maintain 10 ~ 12 hours, sampling analysis, naphthalidine-8-sulfonic acid content≤0.6% is qualified, and qualified rear discharging is to vacuum still, otherwise prolongation is held time.
The subsequent step of the present embodiment is identical with specific embodiment 1.
The N-phenyl-peri acid that the present embodiment prepares, its yield is 93%, and purity is 98%.
specific embodiment 3
The preparation method of the N-phenyl-peri acid described in the present embodiment, comprises the following steps:
(1) condensation: the reaction formula of involved main chemical reactions as shown in Figure 1.
Add in pot by the aniline of the 237kg got ready in scale tank, startup agitator adds the vitriol oil that 441kg concentration is greater than 98%, and when without hydrojet, the naphthalidine-8-sulfonic acid adding 300kg continues to heat up, and carries out normal pressure dehydration.
When material temperature reaches 120 ~ 130 DEG C, dehydration terminates, and measures, if lower than normal volume, then add aniline to volume of material in pot.
Continue to be warming up to 155 ± 2 DEG C, then maintain 10 ~ 12 hours, sampling analysis, naphthalidine-8-sulfonic acid content≤0.6% is qualified, and qualified rear discharging is to vacuum still, otherwise prolongation is held time.
The subsequent step of the present embodiment is identical with specific embodiment 1.
The N-phenyl-peri acid that the present embodiment prepares, its yield is 94%, and purity is 98%.
Above content is detailed description made for the present invention in conjunction with specific embodiments, can not assert that the present invention specifically implements to be only limitted to these explanations.For those skilled in the art, without departing from the inventive concept of the premise, some simple deduction or replace can also be made, all should be considered as belonging to the scope of protection of the invention.
Claims (3)
1. a preparation method for N-phenyl-peri acid, is characterized in that, comprises the following steps:
Step one, condensation: add in pot by the aniline of 78 ~ 80 mass parts, add the vitriol oil that 145 ~ 150 mass parts concentration are greater than 98%, then add the naphthalidine-8-sulfonic acid of 100 mass parts, be then warming up to 120 ~ 130 DEG C, carry out normal pressure dehydration after starting stirring; Then continue to be warming up to 155 ± 2 DEG C, maintain 10 ~ 12 hours, sampling analysis, when naphthalidine-8-sulfonic acid mass concentration is less than or equal to 0.6%, condensation reaction terminates, obtained condensation material;
Step 2, neutralization: in the condensation material that step one is obtained, add soda ash solution neutralize, then go in neutralization pot, adjust material pH value to be 9 ~ 11, in obtained and material;
Step 3, steam distillation: by aniline water adjustment volume of material, the powder that takes a policy carries out steam distillation, and in solution, aniline content is switching point 2 ~ 4%, and less than 3 ± 0.5% extract, obtained thick mother liquor; Until distillation aniline content is lower than 0.3%; In still-process, pH value will remain on more than 9.0;
Step 4, decolouring: start and stir, dilute sulphuric acid is added in the thick mother liquor that step 3 is obtained, adjustment material liquid pH to 6.5 ~ 7.0, add gac afterwards and be warming up to 94 ~ 95 DEG C, be incubated and within 1 ~ 2 hour, do the test of profit circle, make color and luster to green, otherwise add gac, decolour qualified after, by feed liquid filtered while hot, obtained decolouring mother liquor;
Step 5, acid out: the decolouring mother liquor that step 4 is obtained is squeezed in acid out pot, is controlled by temperature of charge at 48 ~ 52 DEG C, adds the dilute sulphuric acid that mass concentration is 28 ~ 32%; The remaining acid content of acid out liquid is made to be 1.8 ~ 2.0%; When being then cooled to below 35 DEG C, discharging obtains N-phenyl-peri acid; After discharging terminates, preparation mass concentration be 1.0 ~ 2.0% sour water N-phenyl-peri acid is washed twice.
2. the preparation method of N-phenyl-peri acid as claimed in claim 1, is characterized in that, in described step one, after dehydration terminates, measures, if lower than normal volume, then add aniline to volume of material in pot.
3. the preparation method of N-phenyl-peri acid as claimed in claim 1, it is characterized in that, after described step one terminates, and also comprised vacuum distilling step before described step 2: start and stir, open vacuum and carry out underpressure distillation, recovery part aniline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201510985284.9A CN105439912A (en) | 2015-12-25 | 2015-12-25 | Preparation method of N-phenyl-1- naphthylamino-8-sulfonic acid |
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| CN201510985284.9A CN105439912A (en) | 2015-12-25 | 2015-12-25 | Preparation method of N-phenyl-1- naphthylamino-8-sulfonic acid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114634428A (en) * | 2022-03-29 | 2022-06-17 | 仁景(苏州)生物科技有限公司 | Microwave condition preparation method of 6-anilino/p-toluidino-2-naphthalenesulfonic acid |
-
2015
- 2015-12-25 CN CN201510985284.9A patent/CN105439912A/en active Pending
Non-Patent Citations (3)
| Title |
|---|
| 上海市有机化学工业公司: "《染料生产工艺汇编》", 31 December 1976 * |
| 刘冲等: "《石油化工手册 第三分册 基本有机原料篇》", 30 September 1987 * |
| 谢筱娟等: "精制苯基周位酸新方法", 《安徽化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114634428A (en) * | 2022-03-29 | 2022-06-17 | 仁景(苏州)生物科技有限公司 | Microwave condition preparation method of 6-anilino/p-toluidino-2-naphthalenesulfonic acid |
| CN114634428B (en) * | 2022-03-29 | 2024-05-10 | 仁景(苏州)生物科技有限公司 | Microwave condition preparation method of 6-anilino/p-toluidinyl-2-naphthalene sulfonic acid |
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Application publication date: 20160330 |