CN106810476B - The method and its system of N-acetylsulfanilyl chloride are synthesized using sulfur trioxide as sulfonating agent - Google Patents
The method and its system of N-acetylsulfanilyl chloride are synthesized using sulfur trioxide as sulfonating agent Download PDFInfo
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- CN106810476B CN106810476B CN201710082831.1A CN201710082831A CN106810476B CN 106810476 B CN106810476 B CN 106810476B CN 201710082831 A CN201710082831 A CN 201710082831A CN 106810476 B CN106810476 B CN 106810476B
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- sulfur trioxide
- chloride
- sulfonating agent
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- thionyl chloride
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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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Abstract
The present invention relates to methods and its system that N-acetylsulfanilyl chloride is synthesized using sulfur trioxide as sulfonating agent, and, the following steps are included: (a) sequentially adds antifebrin and thionyl chloride into reaction kettle, stirring is warming up to 40 ~ 70 DEG C for it；(b) it is passed through sulfur trioxide gas into reaction kettle, is reacted 3 ~ 15 hours at 40 ~ 70 DEG C, makes the antifebrin conversion completely, stopping is passed through sulfur trioxide gas；(c) so that reactor temperature is risen to 65 ~ 80 DEG C, the thionyl chloride is recovered under reduced pressure, it is cooling.It uses sulfur trioxide to synthesize N-acetylsulfanilyl chloride for sulfonating agent, not only can guarantee the quality of N-acetylsulfanilyl chloride in this way, but also avoid generating waste water and spent acid, saved processing cost, be conducive to protect environment.
Description
Technical field
The invention belongs to chemical intermediate preparation fields, and in particular to a kind of to synthesize by sulfonating agent of sulfur trioxide to acetyl
The method and its system of amino phenyl sulfonyl acyl chlorides.
Background technique
N-acetylsulfanilyl chloride is medicine intermediate, is to prepare the sulfamidos such as sulfalene benzisoxazole and sulphathiazole
The primary raw material of medicine, current country are all to prepare wet product based on using by oneself and feed intake at once use, otherwise will be occurred point
It is solution, rotten, reach and guarantee the quality the stable time limit at most also just just three days, be really used as commodity, on the market at present or blank.State
Outer production is mainly using cryodrying technical equipment and spray granulating and drying come finished product, but additive has an impact to reaction.
Development trend is the stability for being conducive to be made product using cryodrying, but is invested larger.In addition, current synthetic method is logical
Often using chlorosulfonic acid as sulfonating agent, antifebrin is added portionwise in chlorosulfonic acid at 40 ~ 60 DEG C, 2 ~ 4h is reacted, is diluted by ice water,
Product is obtained by filtration, chlorosulfonic acid dosage is big in the technique, and the spent acid of generation is more, and processing cost is high.
Summary of the invention
It is provided the invention aims to overcome the deficiencies in the prior art a kind of using sulfur trioxide as sulfonating agent synthesis pair
The method of acetamidobenzenesulfonyl chloride.
In order to achieve the above objectives, the technical solution adopted by the present invention is that: a kind of using sulfur trioxide is sulfonating agent synthesis to second
The method of acylamino- benzene sulfonyl chloride, it the following steps are included:
(a) antifebrin and thionyl chloride are sequentially added into reaction kettle, stirring is warming up to 40 ~ 70 DEG C；
(b) it is passed through sulfur trioxide gas into reaction kettle, is reacted 3 ~ 15 hours at 40 ~ 70 DEG C, turns the antifebrin
Change completely, stopping is passed through sulfur trioxide gas；
(c) so that reactor temperature is risen to 65 ~ 80 DEG C, the thionyl chloride is recovered under reduced pressure, it is cooling.
Optimally, in the step (b), the tail gas in reaction process is absorbed with lye；And when close to reaction end, often
5 ~ 15min sampling analysis is to determine reaction end.
Optimally, in step (a), 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.
It is a kind of using sulfur trioxide as sulfonating agent synthesis N-acetylsulfanilyl chloride another object of the present invention is to provide
System, it include Mix and dosing tank, using pump be connected with the Mix and dosing pot bottom storage tank, using pump with it is described
Film reactor that storage tank is connected, the sulfur trioxide air accumulator being connected with the film reactor, using pump with it is described
Film reactor, which is connected, to be produced for accepting the ageing can of liquid product, being connected with the film reactor for accepting gas phase
First knockout tower of object, the continuous evaporating crystallizer being 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 by triple valve with blower.
Optimally, the continuous evaporating crystallizer is also connected with heat exchanger.
Optimally, it further include the second knockout tower being connected with first knockout tower and with second knockout tower
The sulfur dioxide storage tank being connected.
Due to the above technical solutions, the present invention has the following advantages over the prior art: the present invention is with three oxidations
Sulphur is the method that sulfonating agent synthesizes N-acetylsulfanilyl chloride, and sulfur trioxide is used to synthesize acetylaminobenzene sulphur for sulfonating agent
Acyl chlorides, not only can guarantee the quality of N-acetylsulfanilyl chloride in this way, but also avoid generating waste water and spent acid, has saved and has been processed into
This, is conducive to protect environment.
Detailed description of the invention
Attached drawing 1 is the structural representation for the system that the present invention synthesizes N-acetylsulfanilyl chloride by sulfonating agent of sulfur trioxide
Figure.
Specific embodiment
The preferred embodiment of the invention is described in detail below in conjunction with attached drawing:
Embodiment 1
The present embodiment provides a kind of system for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide, such as Fig. 1
Shown, 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 reaction mass being stirred mixing；Storage tank 3 passes through pipeline and Mix and dosing
The bottom of tank 1 is connected, and pump 2 is equipped on the pipeline between them, can be by the object 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 equipped on the pipeline between them another
The reaction mass stored in storage tank 3 can be imported in film reactor 6 with pump 2 and be reacted by one pump 2.Sulfur trioxide
Air accumulator 14 is connected with film reactor 6, for importing sulfur trioxide gas into 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
4 are connected, and the air so as to be blasted using blower introduces sulfur trioxide gas into film reactor 6 as carrier gas, from
And it can reduce the severity of reaction.Ageing can 11 is connected by pipeline with the bottom of film reactor 6 (to be 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
It connects, 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 evaporating the thionyl chloride in reclaim liquid phase product and obtaining product.
Thionyl chloride storage tank 10 is connected with the first knockout tower 7, for storing the isolated thionyl chloride of the first knockout tower 7.
In the present embodiment, continuous evaporating crystallizer 12 is also connected with heat exchanger 13, thus the dichloro that evaporation is obtained
Sulfoxide is cooled to liquid reuse.Second knockout tower 8 is connected with the first knockout tower 7, to will import from the first knockout tower 7
Product is separated into hydrogen chloride gas (being absorbed with lye) and sulfur dioxide gas；Sulfur dioxide storage tank 9 and the second knockout tower 8
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 methods for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide, it includes
Following steps:
(a) 13.5kg antifebrin and 30kg thionyl chloride are sequentially added into reaction kettle, stirring is warming up to 40 DEG C；
(b) it is slowly introducing sulfur trioxide gas (flow of ventilation is 2.5L/min) into reaction kettle, reacts 15 at 40 DEG C
Hour (tail gas is absorbed with the sodium carbonate liquor of 1mol/L)；When close to reaction end, every 15min sampling analysis (uses liquid phase color
Spectrometer HPLC is analyzed), until antifebrin conversion is completely, stopping is passed through sulfur trioxide gas；
(c) so that reactor temperature is risen to 70 DEG C, be recovered under reduced pressure the thionyl chloride (recycling quality is 17.5kg), it is cooling
N-acetylsulfanilyl chloride crude product (purity 98%, yield 97%) can be obtained.
Embodiment 3
The present embodiment provides a kind of methods for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide, it includes
Following steps:
(a) 13.5kg antifebrin and 60kg thionyl chloride are sequentially added into reaction kettle, stirring is warming up to 70 DEG C；
(b) it is slowly introducing sulfur trioxide gas (flow of ventilation is 13.0L/min) into reaction kettle, reacts 3 at 70 DEG C
Hour (tail gas is absorbed with the sodium carbonate liquor of 1mol/L)；When close to reaction end, every 5min sampling analysis (uses liquid chromatogram
Instrument HPLC is analyzed), until antifebrin conversion is completely, stopping is passed through sulfur trioxide gas；
(c) so that reactor temperature is risen to 80 DEG C, be recovered under reduced pressure the thionyl chloride (recycling quality is 17.1kg), it is cooling
N-acetylsulfanilyl chloride crude product (purity 96%, yield 98%) can be obtained.
Embodiment 4
The present embodiment provides a kind of methods for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide, it includes
Following steps:
(a) 13.5kg antifebrin and 45kg thionyl chloride are sequentially added into reaction kettle, stirring is warming up to 60 DEG C；
(b) it is slowly introducing into reaction kettle sulfur trioxide gas (flow of ventilation is 8.0L/min), it is small in 60 DEG C of reactions 5
When (tail gas is absorbed with the sodium carbonate liquor of 1mol/L)；When close to reaction end, every 10min sampling analysis (uses liquid chromatogram
Instrument HPLC is analyzed), until antifebrin conversion is completely, stopping is passed through sulfur trioxide gas；
(c) so that reactor temperature is risen to 70 DEG C, be recovered under reduced pressure the thionyl chloride (recycling quality is 17.3kg), it is cooling
N-acetylsulfanilyl chloride crude product (purity 97%, yield 98.5%) can be obtained.
Embodiment 5
The present embodiment provides a kind of methods for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide, it includes
Following steps:
(a) 13.5kg antifebrin and 45kg thionyl chloride are sequentially added into reaction kettle, stirring is warming up to 60 DEG C；
(b) it is slowly introducing sulfur trioxide gas (flow of ventilation is 15.0L/min) into reaction kettle, reacts 5 at 60 DEG C
Hour (tail gas is absorbed with the sodium carbonate liquor of 1mol/L)；When close to reaction end, every 10min sampling analysis (uses liquid phase color
Spectrometer HPLC is analyzed), until antifebrin conversion is completely, stopping is passed through sulfur trioxide gas；
(c) so that reactor temperature is risen to 70 DEG C, be recovered under reduced pressure the thionyl chloride (recycling quality is 17.3kg), it is cooling
N-acetylsulfanilyl chloride crude product (purity 95%, yield 94.5%) can be obtained.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention, it is all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (3)
1. it is a kind of using sulfur trioxide as sulfonating agent synthesize N-acetylsulfanilyl chloride method, which is characterized in that it include with
Lower step:
(a) sequentially add antifebrin and thionyl chloride into reaction kettle, stirring is warming up to 40 ~ 70 DEG C, the antifebrin and
The mass ratio of thionyl chloride is 13.5:30 ~ 60；
(b) it is passed through sulfur trioxide gas into reaction kettle, is reacted 3 ~ 15 hours at 40 ~ 70 DEG C, the sulfur trioxide gas leads to
Entering speed is 2.5 ~ 13.0L/min, and when close to reaction end, every 5 ~ 15min sampling analysis is to determine reaction end to described
Completely, stopping is passed through sulfur trioxide gas, and the tail gas in reaction process is absorbed with lye for antifebrin conversion；
(c) so that reactor temperature is risen to 65 ~ 80 DEG C, the thionyl chloride is recovered under reduced pressure, it is cooling.
2. a kind of equipment for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide, it is characterised in that: it includes stirring
Mix material-compound tank (1), the storage tank (3) being connected with Mix and dosing tank (1) bottom using pump (2), using pump (2) with it is described
Film reactor (6) that storage tank (3) is connected, the sulfur trioxide air accumulator (14) being connected with the film reactor (6),
The ageing can (11) and the film type reaction being connected with the film reactor (6) for accepting liquid product using pump (2)
Device (6) is connected for accepting the first knockout tower (7) of gas-phase product, the continuous evaporation knot being connected with the ageing can (11)
Brilliant device (12) and the thionyl chloride storage tank (10) being connected with first knockout tower (7)；The sulfur trioxide air accumulator
(14) it is connected between the film reactor (6) demister (5), the demister (5) also passes through triple valve and blower (4)
It is connected；The continuous evaporating crystallizer (12) is also connected with heat exchanger (13).
3. the equipment for synthesizing N-acetylsulfanilyl chloride as sulfonating agent using sulfur trioxide according to claim 2, feature
Be: it further include the second knockout tower (8) being connected with first knockout tower (7) and with second knockout tower (8)
The sulfur dioxide storage tank (9) being connected.
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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 |