CN106810476A - Synthesize the method and its system of N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide - Google Patents
Synthesize the method and its system of N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide Download PDFInfo
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- CN106810476A CN106810476A CN201710082831.1A CN201710082831A CN106810476A CN 106810476 A CN106810476 A CN 106810476A CN 201710082831 A CN201710082831 A CN 201710082831A CN 106810476 A CN106810476 A CN 106810476A
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- sulfur trioxide
- sulfonating agent
- chloride
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- acetylsulfanilyl
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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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- 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
Method and its system the present invention relates to synthesize N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide, it is comprised the following steps：（a）To antifebrin and thionyl chloride is sequentially added in reactor, stirring is warming up to 40 ~ 70 DEG C；（b）To sulfur trioxide gas are passed through in reactor, reacted 3 ~ 15 hours at 40 ~ 70 DEG C, make the antifebrin conversion complete, stop being passed through sulfur trioxide gas；（c）Reactor temperature is risen to 65 ~ 80 DEG C, the thionyl chloride is recovered under reduced pressure, cool down.Use sulfur trioxide to synthesize N-acetylsulfanilyl chloride for sulfonating agent, so both can guarantee that the quality of N-acetylsulfanilyl chloride, avoid producing waste water and spent acid again, saved processing cost, be conducive to environmental protection.
Description
Technical field
The invention belongs to chemical intermediate preparation field, and in particular to a kind of to synthesize to acetyl by sulfonating agent of sulfur trioxide
The method and its system of amino phenyl sulfonyl acyl chlorides.
Background technology
N-acetylsulfanilyl chloride is medicine intermediate, is to prepare the sulfamidos such as sulfalene Ben isoxazoles and sulphathiazole
The primary raw material of medicine, current country is all based on using by oneself, to prepare wet product and feed intake at once and use, and will otherwise be occurred point
It is solution, rotten, reach time limit of stabilization of guaranteeing the quality at most also just just three days, really as commodity, commercially at present or blank.State
Outer production is main to be had an impact come finished product, but additive using cryodrying technical equipment and spray granulating and drying to reaction.
Development trend is the stability for being conducive to being obtained product using cryodrying, but is invested larger.In addition, current synthetic method is led to
Often with chlorosulfonic acid as sulfonating agent, antifebrin is dividedly in some parts in chlorosulfonic acid at 40 ~ 60 DEG C, reacts 2 ~ 4h, diluted by frozen water,
Product is filtrated to get, chlorosulfonic acid consumption is big in the technique, and the spent acid of generation is more, and processing cost is high.
The content of the invention
There is provided a kind of right as sulfonating agent synthesis with sulfur trioxide the invention aims to overcome the deficiencies in the prior art
The method of ASC.
To reach above-mentioned purpose, the technical solution adopted by the present invention is：It is a kind of to synthesize to second by sulfonating agent of sulfur trioxide
The method of acylamino- benzene sulfonyl chloride, it is comprised the following steps：
（a）To antifebrin and thionyl chloride is sequentially added in reactor, stirring is warming up to 40 ~ 70 DEG C；
（b）To sulfur trioxide gas are passed through in reactor, reacted 3 ~ 15 hours at 40 ~ 70 DEG C, converted the antifebrin
Entirely, stop being passed through sulfur trioxide gas；
（c）Reactor temperature is risen to 65 ~ 80 DEG C, the thionyl chloride is recovered under reduced pressure, cool down.
Optimally, the step（b）In, the tail gas in course of reaction is with alkali liquor absorption；And when close to reaction end, often
5 ~ 15min sampling analyses are determining reaction end.
Optimally, step（a）In, the mass ratio of the antifebrin and thionyl chloride is 13.5：30~60；Step（b）
In, the speed that is passed through of the sulfur trioxide gas is 2.5 ~ 13.0L/min.
A further object of the present invention is that offer one kind is that sulfonating agent synthesizes N-acetylsulfanilyl chloride with sulfur trioxide
System, it include Mix and dosing tank, using pump and the storage tank that the Mix and dosing pot bottom is connected, using pump with it is described
Sulfur trioxide air accumulator that the film reactor that storage tank is connected is connected with the film reactor, using pump with it is described
Film reactor is connected and be connected with the film reactor for accepting gas phase product for accepting the ageing can of liquid product
Continuous evaporating crystallizer that first knockout tower of thing is connected with the ageing can and it is connected with first knockout tower
Thionyl chloride storage tank.
Optimally, demister, the demister are connected between the sulfur trioxide air accumulator and the film reactor
Also it is connected with blower fan by triple valve.
Optimally, the continuous evaporating crystallizer is also connected with heat exchanger.
Optimally, it also include the second knockout tower for being connected with first knockout tower and with second knockout tower
The sulfur dioxide storage tank being connected.
Because above-mentioned technical proposal is used, the present invention has following advantages compared with prior art：The present invention is with three oxidations
Sulphur is the method that sulfonating agent synthesizes N-acetylsulfanilyl chloride, uses sulfur trioxide to synthesize acetylaminobenzene sulphur for sulfonating agent
Acyl chlorides, so both can guarantee that the quality of N-acetylsulfanilyl chloride, avoid producing waste water and spent acid again, has saved and has been processed into
This, is conducive to environmental protection.
Brief description of the drawings
Structural representation of the accompanying drawing 1 for the present invention with sulfur trioxide as the system of sulfonating agent synthesis N-acetylsulfanilyl chloride
Figure.
Specific embodiment
The preferred embodiment of the invention is described in detail below in conjunction with accompanying drawing：
Embodiment 1
The present embodiment provides a kind of system for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide, as shown in figure 1,
It mainly includes Mix and dosing tank 1, pump 2, storage tank 3 and film reactor 6 etc..
Wherein, Mix and dosing tank 1 is used to for reaction mass to be stirred mixing；Storage tank 3 passes through pipeline and Mix and dosing
The bottom of tank 1 is connected, and is provided with pump 2 on pipeline between them, can be by the thing in Mix and dosing tank 1 using pump 2
Material is pumped into storage tank 3.Film reactor 6 is connected also by pipeline with storage tank 3, is provided with the pipeline between them another
One pump 2, the reaction mass of storage in storage tank 3 can be imported reacted in film reactor 6 with pump 2.Sulfur trioxide
Air accumulator 14 is connected with film reactor 6, for importing sulfur trioxide gas in it as sulfonating agent；In the present embodiment
In, demister 5 is connected between sulfur trioxide air accumulator 14 and film reactor 6, and demister 5 also passes through triple valve and blower fan
4 are connected, such that it is able to the air that is blasted by the use of blower fan as carrier gas to introducing sulfur trioxide gas in film reactor 6, from
And the severity of reaction can be reduced.Ageing can 11 is connected by pipeline with the bottom of film reactor 6（Installed on pipeline
There is another pump 2）, for accepting the liquid product in film reactor 6.First knockout tower 7 is also connected with film reactor 6
Connect, it is used to accept the gas-phase product in film reactor 6, and separates the thionyl chloride wherein carried secretly and recycle and reuse.
Continuous evaporating crystallizer 12 is connected with ageing can 11, for the thionyl chloride evaporated in reclaim liquid phase product and obtains product.
Thionyl chloride storage tank 10 is connected with the first knockout tower 7, the thionyl chloride isolated for storing the first knockout tower 7.
In the present embodiment, continuous evaporating crystallizer 12 is also connected with heat exchanger 13, so as to evaporate the dichloro for obtaining
Sulfoxide is cooled to liquid reuse.Second knockout tower 8 is connected with the first knockout tower 7, so as to by from the first knockout tower 7 import
Product is separated into hydrogen chloride gas（With alkali liquor absorption）And sulfur dioxide gas；The knockout tower 8 of sulfur dioxide storage tank 9 and second
It is connected, for storing its isolated sulfur dioxide gas, can be used for preparing thionyl chloride.
Embodiment 2
The present embodiment provides a kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide, and it includes following
Step：
（a）To 13.5kg antifebrins and 30kg thionyl chlorides is sequentially added in reactor, stirring is warming up to 40 DEG C；
（b）To being slowly introducing sulfur trioxide gas in reactor（The flow of ventilation is 2.5L/min）, reacted 15 hours at 40 DEG C
（Tail gas is absorbed with the sodium carbonate liquor of 1mol/L）；During close to reaction end, per 15min sampling analyses（Use liquid chromatograph
HPLC is analyzed）, complete to antifebrin conversion, stopping is passed through sulfur trioxide gas；
（c）Reactor temperature is risen to 70 DEG C, the thionyl chloride is recovered under reduced pressure（Recovery quality is 17.5kg）, cooling
Obtain N-acetylsulfanilyl chloride crude product（Purity is 98%, and yield is 97%）.
Embodiment 3
The present embodiment provides a kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide, and it includes following
Step：
（a）To 13.5kg antifebrins and 60kg thionyl chlorides is sequentially added in reactor, stirring is warming up to 70 DEG C；
（b）To being slowly introducing sulfur trioxide gas in reactor（The flow of ventilation is 13.0L/min）, reacted 3 hours at 70 DEG C
（Tail gas is absorbed with the sodium carbonate liquor of 1mol/L）；During close to reaction end, per 5min sampling analyses（Use liquid chromatograph
HPLC is analyzed）, complete to antifebrin conversion, stopping is passed through sulfur trioxide gas；
（c）Reactor temperature is risen to 80 DEG C, the thionyl chloride is recovered under reduced pressure（Recovery quality is 17.1kg）, cooling
Obtain N-acetylsulfanilyl chloride crude product（Purity is 96%, and yield is 98%）.
Embodiment 4
The present embodiment provides a kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide, and it includes following
Step：
（a）To 13.5kg antifebrins and 45kg thionyl chlorides is sequentially added in reactor, stirring is warming up to 60 DEG C；
（b）To being slowly introducing sulfur trioxide gas in reactor（The flow of ventilation is 8.0L/min）, reacted 5 hours at 60 DEG C
（Tail gas is absorbed with the sodium carbonate liquor of 1mol/L）；During close to reaction end, per 10min sampling analyses（Use liquid chromatograph
HPLC is analyzed）, complete to antifebrin conversion, stopping is passed through sulfur trioxide gas；
（c）Reactor temperature is risen to 70 DEG C, the thionyl chloride is recovered under reduced pressure（Recovery quality is 17.3kg）, cooling
Obtain N-acetylsulfanilyl chloride crude product（Purity is 97%, and yield is 98.5%）.
Embodiment 5
The present embodiment provides a kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide, and it includes following
Step：
（a）To 13.5kg antifebrins and 45kg thionyl chlorides is sequentially added in reactor, stirring is warming up to 60 DEG C；
（b）To being slowly introducing sulfur trioxide gas in reactor（The flow of ventilation is 15.0L/min）, reacted 5 hours at 60 DEG C
（Tail gas is absorbed with the sodium carbonate liquor of 1mol/L）；During close to reaction end, per 10min sampling analyses（Use liquid chromatograph
HPLC is analyzed）, complete to antifebrin conversion, stopping is passed through sulfur trioxide gas；
（c）Reactor temperature is risen to 70 DEG C, the thionyl chloride is recovered under reduced pressure（Recovery quality is 17.3kg）, cooling
Obtain N-acetylsulfanilyl chloride crude product（Purity is 95%, and yield is 94.5%）.
The above embodiments merely illustrate the technical concept and features of the present invention, its object is to allow person skilled in the art
Scholar will appreciate that present disclosure and implement according to this that it is not intended to limit the scope of the present invention, all according to the present invention
The equivalent change or modification that Spirit Essence is made, should all be included within the scope of the present invention.
Claims (7)
1. it is a kind of with sulfur trioxide as sulfonating agent synthesize N-acetylsulfanilyl chloride method, it is characterised in that it include with
Lower step：
（a）To antifebrin and thionyl chloride is sequentially added in reactor, stirring is warming up to 40 ~ 70 DEG C；
（b）To sulfur trioxide gas are passed through in reactor, reacted 3 ~ 15 hours at 40 ~ 70 DEG C, converted the antifebrin
Entirely, stop being passed through sulfur trioxide gas；
（c）Reactor temperature is risen to 65 ~ 80 DEG C, the thionyl chloride is recovered under reduced pressure, cool down.
2. the method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide according to claim 1, its feature
It is：The step（b）In, the tail gas in course of reaction is with alkali liquor absorption；And when close to reaction end, every 5 ~ 15min takes
Sample is analyzed to determine reaction end.
3. the method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide according to claim 1, its feature
It is：Step（a）In, the mass ratio of the antifebrin and thionyl chloride is 13.5：30~60；Step（b）In, three oxygen
That changes sulphur gas is passed through speed for 2.5 ~ 13.0L/min.
4. it is a kind of with sulfur trioxide as sulfonating agent synthesize N-acetylsulfanilyl chloride system, it is characterised in that：It includes stirring
Mix material-compound tank（1）, using pump（2）With the Mix and dosing tank（1）The storage tank that bottom is connected（3）, using pump（2）With it is described
Storage tank（3）The film reactor being connected（6）With the film reactor（6）The sulfur trioxide air accumulator being connected（14）、
Using pump（2）With the film reactor（6）It is connected for the ageing can for accepting liquid product（11）With the film type reaction
Device（6）It is connected for the first knockout tower for accepting gas-phase product（7）With the ageing can（11）The continuous evaporation knot being connected
Brilliant device（12）And with first knockout tower（7）The thionyl chloride storage tank being connected（10）.
5. the system for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide according to claim 4, its feature
It is：The sulfur trioxide air accumulator（14）With the film reactor（6）Between be connected with demister（5）, the demister
（5）Also pass through triple valve and blower fan（4）It is connected.
6. the system for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide according to claim 4, its feature
It is：The continuous evaporating crystallizer（12）Also with heat exchanger（13）It is connected.
7. the system for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide according to claim 4, its feature
It is：It also includes and first knockout tower（7）The second knockout tower being connected（8）And with second knockout tower（8）
The sulfur dioxide storage tank being connected（9）.
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| CN201710082831.1A CN106810476B (en) | 2017-02-16 | 2017-02-16 | The method and its system of N-acetylsulfanilyl chloride are synthesized using sulfur trioxide as sulfonating agent |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108640860A (en) * | 2018-06-12 | 2018-10-12 | 新乡市锦源化工有限公司 | The preparation method and N-acetylsulfanilyl chloride of the N-acetylsulfanilyl chloride of green energy conservation |
| CN111377837A (en) * | 2020-03-18 | 2020-07-07 | 湖南吴赣药业有限公司 | Green synthesis method of p-acetamido-benzenesulfonyl chloride |
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2017
- 2017-02-16 CN CN201710082831.1A patent/CN106810476B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108640860A (en) * | 2018-06-12 | 2018-10-12 | 新乡市锦源化工有限公司 | The preparation method and N-acetylsulfanilyl chloride of the N-acetylsulfanilyl chloride of green energy conservation |
| CN111377837A (en) * | 2020-03-18 | 2020-07-07 | 湖南吴赣药业有限公司 | Green synthesis method of p-acetamido-benzenesulfonyl chloride |
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Denomination of invention: Method and system for synthesizing p-acetylaminobenzene sulfonyl chloride with sulfur trioxide as sulfonating agent Effective date of registration: 20210831 Granted publication date: 20181204 Pledgee: Bank of China Limited Suzhou Yangtze River Delta integration Demonstration Zone Branch Pledgor: WUGAN PHARMACEUTICAL (SUZHOU) Co.,Ltd. Registration number: Y2021980008614 |