CN108640859A - The high-efficiency synthesis method and N-acetylsulfanilyl chloride of N-acetylsulfanilyl chloride - Google Patents
The high-efficiency synthesis method and N-acetylsulfanilyl chloride of N-acetylsulfanilyl chloride Download PDFInfo
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- CN108640859A CN108640859A CN201810601015.1A CN201810601015A CN108640859A CN 108640859 A CN108640859 A CN 108640859A CN 201810601015 A CN201810601015 A CN 201810601015A CN 108640859 A CN108640859 A CN 108640859A
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- blown
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- antifebrin
- liquid level
- chlorosulfonic acid
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- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000001308 synthesis method Methods 0.000 title claims abstract description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 104
- 238000006243 chemical reaction Methods 0.000 claims abstract description 93
- 239000007788 liquid Substances 0.000 claims abstract description 77
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 64
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 64
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 38
- 238000003756 stirring Methods 0.000 claims abstract description 31
- 239000000843 powder Substances 0.000 claims abstract description 16
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 12
- 239000012320 chlorinating reagent Substances 0.000 claims abstract description 12
- 230000009471 action Effects 0.000 claims abstract description 7
- 230000002045 lasting effect Effects 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims description 36
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 14
- 235000019270 ammonium chloride Nutrition 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 24
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 17
- 239000007789 gas Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 12
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical group ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000011344 liquid material Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000007664 blowing Methods 0.000 description 5
- 230000036632 reaction speed Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000013517 stratification Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- 238000009423 ventilation Methods 0.000 description 4
- 238000000889 atomisation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003595 mist Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VKPQLZPZPYQFOK-UHFFFAOYSA-N 2-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=CC=C1S(Cl)(=O)=O VKPQLZPZPYQFOK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 1
- MTERSQYMYBGZTP-UHFFFAOYSA-N 4-amino-n-(5-methyl-2-phenylpyrazol-3-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1N1N=C(C)C=C1NS(=O)(=O)C1=CC=C(N)C=C1 MTERSQYMYBGZTP-UHFFFAOYSA-N 0.000 description 1
- ANSIGNWRQRYZTC-UHFFFAOYSA-N C(C)(=O)NC1=CC=CC=C1.[S] Chemical compound C(C)(=O)NC1=CC=CC=C1.[S] ANSIGNWRQRYZTC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229950003013 sulfapyrazole Drugs 0.000 description 1
- YZMCKZRAOLZXAZ-UHFFFAOYSA-N sulfisomidine Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 YZMCKZRAOLZXAZ-UHFFFAOYSA-N 0.000 description 1
- -1 sulfonamidoxazole Chemical compound 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C303/08—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 halogenosulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/88—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The high-efficiency synthesis method and N-acetylsulfanilyl chloride of N-acetylsulfanilyl chloride, belong to chemical field.Synthetic method is included under lasting stirring action：Under conditions of 10 20 DEG C of temperature, the atomized drop of the powder of the antifebrin of 1/4 1/3 weight and the chlorosulfonic acid of 1/3 1/2 weight is blown by air pressure in chloroform to reaction kettle using extraneous air respectively and reaches 0.3 0.4MPa, the powder of remaining antifebrin and remaining atomized drop are blown into chloroform and obtain reaction solution respectively using inner air.Continue under conditions of reaction solution is blown into inner air, reaction solution, which is heated to 50 55 DEG C of 20 40min of sulfonating reaction, obtains sulfonated liquid, and sulfonated liquid is heated to 70 75 DEG C and adds 80 100min of chlorinating agent and chlorination auxiliary agent chlorination reaction.Aggregate velocity is fast, raw material reaction is thorough, chlorosulfonic acid dosage is few, product yield is high.Obtained N-acetylsulfanilyl chloride production is fast, at low cost, quality is high.
Description
Technical field
The present invention relates to chemical fields, and the high-efficiency synthesis method of more particularly to a kind of N-acetylsulfanilyl chloride and right
Acetamidobenzenesulfonyl chloride.
Background technology
N-acetylsulfanilyl chloride is to prepare sulfamido sterilization to press down the phonetic azoles of mould drug such as sulfanilamide (SN), sulfonamidoxazole, sulfanilamide (SN)
The intermediate of methyl-isoxazole, sulfapyrazole and domian etc., is also used for synthetic dyestuffs, is widely used in curing
The fields such as medicine, coating, plastics and pesticide.
Currently, the production of N-acetylsulfanilyl chloride mostly uses greatly excess chlorine sulfonic acid carries out chlorosulfonation to antifebrin
Traditional handicraft.But in synthesis technology, antifebrin is solid, and the viscosity of chlorosulfonic acid is larger, and reaction system stirring is difficult, leads to chlorine
The problems such as sulfonic acid and antifebrin are insufficient contact, the reaction time is longer, reaction is not thorough enough.
In view of this, special propose the application.
Invention content
The purpose of the present invention is to provide a kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, aggregate velocities
Soon, raw material reaction is thoroughly, chlorosulfonic acid dosage is few, product yield is high.
Another object of the present invention is to provide a kind of N-acetylsulfanilyl chlorides, produce fast, at low cost, quality
It is high.
The present invention solves its technical problem using following technical scheme to realize.
The present invention proposes a kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, including：
Under lasting stirring action：Under conditions of 10-20 DEG C of temperature, using extraneous air by the second of 1/4-1/3 weight
The atomized drop of the powder of anilide and the chlorosulfonic acid of 1/3-1/2 weight is blown into air pressure in chloroform to reaction kettle and reaches 0.3- respectively
The powder of remaining antifebrin and remaining atomized drop are blown into chloroform and obtain reaction solution by 0.4MPa respectively using inner air；After
Continuing under conditions of reaction solution is blown into inner air, reaction solution, which is heated to 50-55 DEG C of sulfonating reaction 20-40min, obtains sulfonated liquid,
Sulfonated liquid is heated to 70-75 DEG C and adds chlorinating agent and chlorination auxiliary agent chlorination reaction 80-100min.
Preferably, the molar ratio of antifebrin, chlorosulfonic acid, chlorinating agent and chlorination auxiliary agent is followed successively by 1:2.1-2.5:1.2-
1.5:0.1-0.2。
The present invention proposes a kind of N-acetylsulfanilyl chloride, is made according to above-mentioned synthetic method.
The advantageous effect of the embodiment of the present invention is：
Antifebrin and chlorosulfonic acid are dissolved in chlorine by the high-efficiency synthesis method of N-acetylsulfanilyl chloride provided by the invention
Reaction in imitative, raw material contact is abundant, quick and high efficient reaction.Sulfonating reaction, the dosage of chlorosulfonic acid are carried out using chlorosulfonic acid in reaction
It substantially reduces；Chlorination reaction is carried out using chlorinating agent and chlorination auxiliary agent, increases chlorination collision opportunity, is conducive to the forward direction of reaction
Carry out raising reaction speed.
In mixing process, antifebrin and chlorosulfonic acid are blown by gas in chloroform respectively, raw material is in the process being blown into
In constantly dissolve, avoid the excessive influence dissolved efficiency of local concentration；Mechanical agitation and gas, which are blown into, generates dual batch mixing effect, mixes
It closes more rapidly, fully.Through inventor the study found that the air pressure in reaction kettle can be increased by first introducing extraneous gas, be conducive to increase
The perturbation action of atmospheric；With in chloroform solutes content gradually increase its to the rate of dissolution of antifebrin and chlorosulfonic acid by
Gradually reduce, and there is chloroform great volatility to make to contain a large amount of chloroform in the inner air of reaction kettle, the later stage is using internal
Air is blown into raw material and can carry out pre-wrapped to raw material first with the chloroform in inner air and be pre-dissolved, and is conducive to improve raw material and chlorine
Imitative compatibility and to the rate of dissolution in chloroform.Batch mixing is carried out using the method that gas is blown into, after the completion of raw material is filled with
Sulfonating reaction is carried out, the time that raw material is mixed is saved.Simultaneously as raw material mix stages antifebrin and chlorosulfonic acid are abundant
Dispersing contact makes the speed of sulfonating reaction greatly speed up.In addition, gas be blown into convenient for chlorination stage reduce mixing speed it is normally anti-
It answers, enables solution Fast-Balance layering after reaction, reaction speed further speeds up.
N-acetylsulfanilyl chloride provided by the invention is made according to above-mentioned high-efficiency synthesis method, correspondingly has
It is standby to produce the advantages that fast, at low cost, quality is high.
Specific implementation mode
It in order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below will be in the embodiment of the present invention
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, builds according to normal condition or manufacturer
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
High-efficiency synthesis method to the N-acetylsulfanilyl chloride of the embodiment of the present invention and acetylaminobenzene sulphur below
Acyl chlorides is specifically described.
The present invention provides a kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, including N-acetylsulfanilyl chloride
Synthesis, crystallisation by cooling, filtering and washing.
The synthesis of N-acetylsulfanilyl chloride mixes antifebrin and chlorosulfonic acid in chloroform, is carried out after the completion of batch mixing
Sulfonating reaction, sulfonating reaction adds chlorinating agent after the completion and chlorination auxiliary agent carries out chlorination reaction.
Antifebrin and chlorosulfonic acid are dissolved in chloroform and reacting by the above method, keep raw material contact abundant, quick and high efficient reaction.
Chlorosulfonic acid is only used for carrying out sulfonating reaction to antifebrin in reaction, and the dosage of chlorosulfonic acid substantially reduces；Using chlorinating agent and chlorine
Change auxiliary agent and carry out chlorination reaction, increase chlorination collision opportunity, is conducive to the positive of reaction and carries out and then improve reaction speed.
In some optional embodiment modes of the invention, chlorinating agent is phosphorus pentachloride, and chlorination auxiliary agent is ammonium chloride.Pentachloro-
Change phosphorus and contains the chance for considerably increasing chlorination collision there are five chlorine atom；The possibility of Cl- attack S-O keys is higher than O-H keys, sulphur
The electron cloud of S is thinned out by the absorption of three O on acidic group, increases the chance by Cl- attacks；Phosphorus pentachloride has power
The phosphorus oxychloride of advantage, generation is more stable, while hydrogen chloride is constantly detached from reaction system, be conducive to reaction it is positive into
Row.The by-product sulfuric acid reaction of ammonium chloride and sulfonating reaction promotes the positive of reaction to carry out, improves reaction speed, improves chlorination
The yield of N-acetylsulfanilyl chloride after reaction.
Further, the molar ratio of antifebrin and chloroform is 1:3-4, such as 1:3、1:3.2、1:3.4、1:3.6、1:
3.8、1:4 etc..Antifebrin, chlorosulfonic acid, chlorinating agent and chlorination auxiliary agent molar ratio be followed successively by 1:2.1-2.5:1.2-1.5:
0.1-0.2, it is therefore preferable to 1:2.1-2.3:1.2-1.3:0.1, such as can be 1:2.1:1.2:0.1、1:2.2:1.2:0.1、
1:2.3:1.3:0.1 etc..Input is low, output is high for it.
Batch mixing operation carries out under conditions of normal pressure, 10-20 DEG C of temperature, for example, temperature be about 10 DEG C, 12 DEG C, 14 DEG C,
It is carried out under conditions of 16 DEG C, 18 DEG C, 20 DEG C.Ensure stability of the raw material in mixing process, is conducive to the purity for improving product.
Specifically：
Batch mixing operation is carried out with mechanical agitation in a kettle, after chloroform is put into reaction kettle, by the powder of antifebrin
Body is blown by gas in the chloroform of reaction kettle, while the atomized drop of chlorosulfonic acid being blown into the chloroform of reaction kettle.Chlorosulfonic acid
It is atomized using atomizer, nebulization efficiency is high.
The operation extraneous air that raw material is blown into using air is blown into and is blown into two stages with inner air.It is provided using air pump
Power, using sequencing valve control valve open and close control inlet channel：Use extraneous air by the powder of part antifebrin first
It is blown into the chloroform of reaction kettle by two charge pipes with the atomized drop of part chlorosulfonic acid, blowing time blows when reaching 4-6min
The antifebrin entered accounts for the 1/4-1/3 of antifebrin gross mass, the chlorosulfonic acid being blown into accounts for the 1/3-1/2 of chlorosulfonic acid gross mass, this
When reaction kettle in air pressure reach 0.3-0.4MPa.Secondly, it is switched to and is continued remaining acetyl using the inner air of reaction kettle
The powder of aniline and the atomized drop of part chlorosulfonic acid are blown into the chloroform of reaction kettle, blowing time 12-15min.It obtains anti-
Answer liquid.
In the operation of above-mentioned batch mixing, antifebrin and chlorosulfonic acid are blown by gas in chloroform respectively, raw material is being blown into
Constantly dissolving in the process, avoids the excessive influence dissolved efficiency of local concentration；Mechanical agitation and gas, which are blown into, generates dual batch mixing work
With the interlayer that upset is formed by mechanical agitation, mixing is more rapidly, fully.Through inventor the study found that first introducing extraneous gas
The air pressure in reaction kettle can be increased, be conducive to the perturbation action for increasing gas；With the gradual increase of solutes content in chloroform
It continuously decreases the rate of dissolution of antifebrin and chlorosulfonic acid, and the inside that there is chloroform great volatility to make reaction kettle is empty
Contain a large amount of chloroform in gas, the later stage is blown into raw material using inner air and can be carried out to raw material first with the chloroform in inner air
It pre-wrapped and is pre-dissolved, is conducive to the compatibility for improving raw material and chloroform and to the rate of dissolution in chloroform.
It is blown into speed according to what aforesaid operations condition controlled extraneous air and inner air, raw material has faster in chloroform
Dissolved efficiency can carry out adequately dissolving mixing during raw material adds, and 20min or so can be completed, and charging is completed
It is to carry out sulfonating reaction at once to be not necessarily to individually stirring afterwards, saves the time that raw material is mixed.
In some optional embodiments of the invention, antifebrin and chlorosulfonic acid are blown into chlorine along the tangential of reaction kettle respectively
It is imitative, the rotation direction for being blown into direction and stirring of antifebrin on the contrary, chlorosulfonic acid the rotation direction phase for being blown into direction and stirring
Together.
Control it is above-mentioned be blown into direction, in antifebrin and chlorosulfonic acid one fair current be blown into another one adverse current and be blown into so that second
Anilide and chlorosulfonic acid can be sufficiently mixed.Since antifebrin is powder, the solution rate in chlorosulfonic acid is compared with chlorosulfonic acid
Solution rate it is slow, control antifebrin countercurrent direction is blown into, and so that liquid material in stirring is had to impulse force with antifebrin, is helped
In the dissolving for accelerating antifebrin.
Further, stirring liquid level is less than the liquid level that is blown into of antifebrin and chlorosulfonic acid, i.e. antifebrin and chlorosulfonic acid point
It is not blown into above paddle.Paddle is mixed in the bottom of reaction solution, and the stirring action in lower section can disturb top
Liquid material keeps stirring more abundant, while preventing liquid splash and raw material is made to be attached to reaction kettle inner wall.
In preferred embodiments of the present invention, antifebrin is blown into that liquid level is located at stirring liquid level and chlorosulfonic acid is blown into liquid
Between position.Through inventor the study found that due to that can float when antifebrin is blown into chloroform, when chlorosulfonic acid is blown into chloroform can under
It is heavy, antifebrin is blown into below chlorosulfonic acid, chlorosulfonic acid and antifebrin are the relative motion with concurrent-countercurrent the case where
Under, while there is the relative motion of floating and sinking, so that the mixing of antifebrin and chlorosulfonic acid is more homogenized.
Optionally, for stirring liquid level at away from liquid level 2/3-3/4, the liquid level that is blown into of antifebrin is being not less than 1/2 away from liquid level
Place, chlorosulfonic acid are blown into liquid level at away from liquid level 1/4-1/3.Such as stirring liquid level, at away from liquid level 2/3, antifebrin is blown into
For liquid level at away from liquid level 1/2, chlorosulfonic acid is blown into liquid level at away from liquid level 1/3.
In sulfonating reaction and chlorination reaction process, continues with air pump and power is provided, the inner air of reaction kettle is extracted out
After be blown into liquid material.Constantly inner air is blown into solution, cooperative mechanical stirring solution is sufficiently mixed, upset by
Mechanical agitation and the interlayer formed promote the positive of reaction to carry out.In addition, gas is blown into reduces mixing speed convenient for chlorination stage
Normal reaction enables solution Fast-Balance layering after reaction, and layering is quick, effect is good.
Kettle jacket steam is opened when sulfonating reaction, liquid material in reaction kettle is heated to 50-55 DEG C, coordinate under stirring action logical
Gas carries out sulfonating reaction.Mixing speed is optionally 400-600r/min, such as can be 400r/min, 450r/min, 500r/
Min, 550r/min, 600r/min etc.；Inner air is blown into identical draft speed when holding and batch mixing operation.Due to batch mixing
Stage antifebrin and chlorosulfonic acid fully dispersed contact when operation, stirring cooperation ventilation in reaction process are pressed in simultaneous reactions kettle
Power is maintained at 0.3-0.4MPa, and sulfonating reaction 20-40min is made to can be completed to obtain sulfonated liquid.
Chlorination reaction time sulfonated liquid continues to be heated to 70-75 DEG C, opens reaction kettle charge door, adds chlorinating agent in proportion
And chlorination auxiliary agent chlorination reaction 80-100min, obtain the chlorated liquid of the product containing N-acetylsulfanilyl chloride.
In preferably embodiment of the invention, chlorination reaction includes the first stage carried out successively, second stage and the
Three stages.
The ratio between the used time of first stage, second stage and phase III are followed successively by 1:5-7:2-3.Such as：First stage
10min, second stage 50min and phase III 20min；First stage 10min, second stage 60min and phase III
30min；First stage 10min, second stage 70min and phase III 20min etc..
, the mixing speed 350- equal with during sulfonating reaction that be blown into speed of inner air in first stage
400r/min.Inner air is blown into be blown into speed 2/ that speed is about inner air during sulfonating reaction in second stage
3, mixing speed 250-300r/min.The speed that is blown into of inner air is about inside during sulfonating reaction in phase III
Be blown into speed 1/2 of air, mixing speed 150-200r/min.
Chlorination reaction is operated according to above-mentioned each stage, and mixing speed is gradual according to certain speed since the first stage
Reducing, the speed that is blown into of inner air coordinates the reduction situation of rotating speed to be gradually reduced according to appropriate speed since second stage,
Ensure that reaction is from second stage later stage to phase III while capable of carrying out the forward reaction of sufficient chlorination reaction in liquid material
The layering that sulfonated oil and solvent are gradually proceeded by during abundant reaction, is on the one hand conducive to solution energy after chlorination reaction
Enough Fast-Balance layerings, make that layering is quick, effect is good；On the other hand since the concentration of chlorination reaction late phase reaction raw material drops significantly
Low to be unfavorable for quick and sufficient reaction, the state being gradually layered is conducive to the aggregation of raw material, convenient for the abundant anti-of surplus stock
The purity for answering, and then accelerating reaction speed, improving product.
In the operating process for carrying out crystallisation by cooling to the sulfonated oil that chlorated liquid is layered, sulfonated oil is placed in crystallization kettle
In, and chilled brine is passed through into crystallization kettle chuck, keep feed temperature in crystallisation by cooling kettle to be no more than 25 DEG C.By given pace
Ice water is added, being stirred continuously makes N-acetylsulfanilyl chloride crystallize precipitation in diluted acid.
Filtering and washing operation in, the acid solution containing N-acetylsulfanilyl chloride is passed through filter centrifugal, make acid solution with
N-acetylsulfanilyl chloride crystal detaches.Acid solution places the recovery processing of acid solution storage tank, and N-acetylsulfanilyl chloride crystal is logical
It is washed to sink.
The present invention provides a kind of N-acetylsulfanilyl chloride, is made according to above-mentioned high-efficiency synthesis method, has production
Soon, at low cost, the advantages that quality is high.
The feature and performance of the present invention are described in further detail with reference to embodiments.
Embodiment 1
A kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, including：
S1, it is followed successively by 1 according to molar ratio:2.2:1.2:0.1:3.5 are on the waiting list antifebrin, chlorosulfonic acid, phosphorus pentachloride, chlorination
Ammonium and chloroform.
Under conditions of S2,12-18 DEG C of temperature, chloroform is added in reaction kettle, is stirred with the rotating speed of 500r/min.It adopts
It is blown into chloroform 6min with extraneous air, respectively by the powder of the antifebrin of 1/3 weight and the chlorosulfonic acid of 1/2 weight through mist
Atomized drop after change nozzle atomization, which is blown into chloroform, makes air pressure in reaction kettle reach 0.35MPa.Using extraneous air to chloroform
The atomized drop of the powder of remaining antifebrin and chlorosulfonic acid after atomizer is atomized is blown into chloroform by middle air blowing 15min
In.Obtain reaction solution.
Wherein, stirring liquid level is at away from liquid level 2/3；Antifebrin is blown into liquid level at away from liquid level 1/2, along turn with stirring
Dynamic side is blown into the opposite direction；Chlorosulfonic acid is blown into liquid level at away from liquid level 1/3, along direction identical with the rotation direction of stirring
It is blown into.
S3, reaction solution is heated to 50-55 DEG C, is stirred with the rotating speed of 500r/min, and according to being passed through inside in S2
The speed of the method for air continues to be passed through inner air into liquid material, reacts 30min, obtains sulfonated liquid.
S4, sulfonated liquid is heated to 70-75 DEG C, phosphorus pentachloride and ammonium chloride is added, stirred and according to the ventilation side in S3
Method recycles inner air.10min is reacted under the conditions of 400r/min mixing speeds and draft speed identical with S3；In 300r/
50min is reacted under conditions of the 2/3 of min mixing speeds and S3 draft speed；In 200r/min mixing speeds and S3 draft speed
1/2 under conditions of react 20min.Obtain chlorated liquid.
S5, by chlorated liquid stratification 80min, obtain the solvent on upper layer and the sulfonated oil of lower layer.Detach the sulfonation of lower layer
Oil carries out crystallisation by cooling, centrifugal filtration, washing, drying, obtains N-acetylsulfanilyl chloride.
Embodiment 2
A kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, including：
S1, it is followed successively by 1 according to molar ratio:2.1:1.5:0.1:3.5 are on the waiting list antifebrin, chlorosulfonic acid, phosphorus pentachloride, chlorination
Ammonium and chloroform.
Under conditions of S2,15-18 DEG C of temperature, chloroform is added in reaction kettle, is stirred with the rotating speed of 600r/min.It adopts
It is blown into chloroform 6min with extraneous air, respectively by the powder of the antifebrin of 1/4 weight and the chlorosulfonic acid of 1/3 weight through mist
Atomized drop after change nozzle atomization, which is blown into chloroform, makes air pressure in reaction kettle reach 0.4MPa.Using extraneous air into chloroform
The atomized drop of the powder of remaining antifebrin and chlorosulfonic acid after atomizer is atomized is blown into chloroform by air blowing 15min.
Obtain reaction solution.
Wherein, stirring liquid level is at away from liquid level 2/3；Antifebrin is blown into liquid level at away from liquid level 1/2, along turn with stirring
Dynamic side is blown into the opposite direction；Chlorosulfonic acid is blown into liquid level at away from liquid level 1/3, along direction identical with the rotation direction of stirring
It is blown into.
S3, reaction solution is heated to 50-55 DEG C, is stirred with the rotating speed of 600r/min, and according to being passed through inside in S2
The speed of the method for air continues to be passed through inner air into liquid material, reacts 20min, obtains sulfonated liquid.
S4, sulfonated liquid is heated to 70-75 DEG C, phosphorus pentachloride and ammonium chloride is added, stirred and according to the ventilation side in S3
Method recycles inner air.10min is reacted under the conditions of 400r/min mixing speeds and draft speed identical with S3；In 300r/
70min is reacted under conditions of the 2/3 of min mixing speeds and S3 draft speed；In 150r/min mixing speeds and S3 draft speed
1/2 under conditions of react 20min.Obtain chlorated liquid.
S5, by chlorated liquid stratification 80min, obtain the solvent on upper layer and the sulfonated oil of lower layer.Detach the sulfonation of lower layer
Oil carries out crystallisation by cooling, centrifugal filtration, washing, drying, obtains N-acetylsulfanilyl chloride.
Embodiment 3
A kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, including：
S1, it is followed successively by 1 according to molar ratio:2.3:1.3:0.1:3.5 are on the waiting list antifebrin, chlorosulfonic acid, phosphorus pentachloride, chlorination
Ammonium and chloroform.
Under conditions of S2,12-18 DEG C of temperature, chloroform is added in reaction kettle, is stirred with the rotating speed of 400r/min.It adopts
It is blown into chloroform 5min with extraneous air, respectively by the powder of the antifebrin of 1/3 weight and the chlorosulfonic acid of 1/3 weight through mist
Atomized drop after change nozzle atomization, which is blown into chloroform, makes air pressure in reaction kettle reach 0.3MPa.Using extraneous air into chloroform
The atomized drop of the powder of remaining antifebrin and chlorosulfonic acid after atomizer is atomized is blown into chloroform by air blowing 15min.
Obtain reaction solution.
Wherein, stirring liquid level is at away from liquid level 2/3；Antifebrin is blown into liquid level at away from liquid level 1/2, along turn with stirring
Dynamic side is blown into the opposite direction；Chlorosulfonic acid is blown into liquid level at away from liquid level 1/3, along direction identical with the rotation direction of stirring
It is blown into.
S3, reaction solution is heated to 50-55 DEG C, is stirred with the rotating speed of 400r/min, and according to being passed through inside in S2
The speed of the method for air continues to be passed through inner air into liquid material, reacts 40min, obtains sulfonated liquid.
S4, sulfonated liquid is heated to 70-75 DEG C, phosphorus pentachloride and ammonium chloride is added, stirred and according to the ventilation side in S3
Method recycles inner air.10min is reacted under the conditions of 350r/min mixing speeds and draft speed identical with S3；In 300r/
60min is reacted under conditions of the 2/3 of min mixing speeds and S3 draft speed；In 150r/min mixing speeds and S3 draft speed
1/2 under conditions of react 30min.Obtain chlorated liquid.
S5, by chlorated liquid stratification 80min, obtain the solvent on upper layer and the sulfonated oil of lower layer.Detach the sulfonation of lower layer
Oil carries out crystallisation by cooling, centrifugal filtration, washing, drying, obtains N-acetylsulfanilyl chloride.
Embodiment 4
A kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, difference from example 1 is that：S2 steps
In, antifebrin and chlorosulfonic acid are blown into liquid level at away from liquid level 1/2, and along direction identical with the rotation direction of stirring
It is blown into.
Embodiment 5
A kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, difference from example 1 is that：Chlorine in S4
The mixing speed and draft speed for changing reaction remain unchanged, and identical as the condition of sulfonating reaction in S3 respectively.Chlorated liquid in S5
The time of stratification is 120min.
Comparative example 1
A kind of synthetic method of N-acetylsulfanilyl chloride, including：
S1, it is followed successively by 1 according to molar ratio:2.2:1.2:0.1:3.5 are on the waiting list antifebrin, chlorosulfonic acid, phosphorus pentachloride, chlorination
Ammonium and chloroform.
Under conditions of S2,12-18 DEG C of temperature, chloroform is added in reaction kettle, chloroform is added in antifebrin and chlorosulfonic acid
In, 20min is stirred with the rotating speed of 500r/min, obtains reaction solution.
S3, reaction solution is heated to 50-55 DEG C, 30min is stirred with the rotating speed of 500r/min, obtains sulfonated liquid.
S4, sulfonated liquid is heated to 70-75 DEG C, phosphorus pentachloride and ammonium chloride is added, stirred with the rotating speed of 500r/min
80min obtains chlorated liquid.
S5, by chlorated liquid stratification 80min, obtain the solvent on upper layer and the sulfonated oil of lower layer.Detach the sulfonation of lower layer
Oil carries out crystallisation by cooling, centrifugal filtration, washing, drying, obtains N-acetylsulfanilyl chloride.
Test example
The yield of N-acetylsulfanilyl chloride is according to mass balance made from method to embodiment 1-5 and comparative example 1
Calculate and be measured purity, the results are shown in Table 1.
1 acetamidobenzenesulfonyl chloride yield of table and purity data table
According to table 1 it is found that embodiment 1-5 is compared with the method that comparative example 1 provides, in the case of identical material ratio,
Embodiment 1-5 is provided in the identical reaction time the obtained product yield of method is high, purity is high.
To sum up, the high-efficiency synthesis method of N-acetylsulfanilyl chloride provided in an embodiment of the present invention, aggregate velocity is fast,
Raw material reaction is thoroughly, chlorosulfonic acid dosage is few, product yield is high.N-acetylsulfanilyl chloride obtained, which has, produces fast, cost
Low, the advantages that quality is high.
Embodiments described above is a part of the embodiment of the present invention, instead of all the embodiments.The reality of the present invention
The detailed description for applying example is not intended to limit the range of claimed invention, but is merely representative of the selected implementation of the present invention
Example.Based on the embodiments of the present invention, those of ordinary skill in the art are obtained without creative efforts
Every other embodiment, shall fall within the protection scope of the present invention.
Claims (10)
1. a kind of high-efficiency synthesis method of N-acetylsulfanilyl chloride, which is characterized in that including：
Under lasting stirring action：Under conditions of 10-20 DEG C of temperature, using extraneous air by the acetophenone of 1/4-1/3 weight
The atomized drop of the powder of amine and the chlorosulfonic acid of 1/3-1/2 weight is blown into air pressure in chloroform to reaction kettle and reaches 0.3- respectively
The powder of the remaining antifebrin and the remaining atomized drop are blown into the chloroform by 0.4MPa respectively using inner air
Obtain reaction solution；Continue under conditions of the reaction solution is blown into the inner air, the reaction solution is heated to 50-55 DEG C of sulphur
Change reaction 20-40min and obtain sulfonated liquid, the sulfonated liquid is heated to 70-75 DEG C and adds chlorinating agent and chlorination auxiliary agent chlorination is anti-
Answer 80-100min；
Preferably, the molar ratio of the antifebrin, the chlorosulfonic acid, the chlorinating agent and the chlorination auxiliary agent is followed successively by 1:
2.1-2.5:1.2-1.5:0.1-0.2。
2. high-efficiency synthesis method according to claim 1, which is characterized in that the antifebrin and chlorosulfonic acid difference
It is tangentially blown into the chloroform along the reaction kettle, the rotation direction for being blown into direction and stirring of the antifebrin is on the contrary, institute
State chlorosulfonic acid to be blown into direction identical as the rotation direction of stirring.
3. high-efficiency synthesis method according to claim 1, which is characterized in that stirring liquid level is less than the antifebrin and institute
That states chlorosulfonic acid is blown into liquid level.
4. high-efficiency synthesis method according to claim 3, which is characterized in that the antifebrin be blown into liquid level be located at stir
Mix being blown between liquid level of liquid level and the chlorosulfonic acid.
5. high-efficiency synthesis method according to claim 3, which is characterized in that stirring liquid level is at away from liquid level 2/3-3/4, institute
That states antifebrin is blown into liquid level at away from liquid level not less than 1/2, and the chlorosulfonic acid is blown into liquid level away from liquid level 1/4-1/3
Place.
6. high-efficiency synthesis method according to claim 1, which is characterized in that the mixing speed before chlorination reaction is 400-
600r/min, mixing speed is gradually reduced in chlorination reaction.
7. high-efficiency synthesis method according to claim 6, which is characterized in that chlorination reaction includes the first rank carried out successively
The mixing speed of section, second stage and phase III, first stage are 350-400r/min, and the mixing speed of second stage is
The mixing speed of 250-300r/min, phase III are 150-200r/min.
8. high-efficiency synthesis method according to claim 7, which is characterized in that first stage, second stage and phase III
The ratio between used time be followed successively by 1:5-7:2-3.
9. according to claim 1-8 any one of them high-efficiency synthesis methods, which is characterized in that the chlorinating agent is phosphoric
Phosphorus, the chlorination auxiliary agent are ammonium chloride.
10. a kind of N-acetylsulfanilyl chloride as made from claim 1-9 any one of them high-efficiency synthesis methods.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110156643A (en) * | 2019-06-24 | 2019-08-23 | 新乡市锦源化工有限公司 | A kind of N-acetylsulfanilyl chloride efficient catalytic preparation method |
| CN110724073A (en) * | 2019-10-28 | 2020-01-24 | 新乡市锦源化工有限公司 | Production process of p-acetamido-benzenesulfonyl chloride |
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| CN110156643A (en) * | 2019-06-24 | 2019-08-23 | 新乡市锦源化工有限公司 | A kind of N-acetylsulfanilyl chloride efficient catalytic preparation method |
| CN110724073A (en) * | 2019-10-28 | 2020-01-24 | 新乡市锦源化工有限公司 | Production process of p-acetamido-benzenesulfonyl chloride |
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