CN102304070A - Process for producing p-acetamidobenzene sulfonyl chloride - Google Patents
Process for producing p-acetamidobenzene sulfonyl chloride Download PDFInfo
- Publication number
- CN102304070A CN102304070A CN201110110232A CN201110110232A CN102304070A CN 102304070 A CN102304070 A CN 102304070A CN 201110110232 A CN201110110232 A CN 201110110232A CN 201110110232 A CN201110110232 A CN 201110110232A CN 102304070 A CN102304070 A CN 102304070A
- Authority
- CN
- China
- Prior art keywords
- acetanilide
- finished product
- product
- ethylene dichloride
- production technique
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 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 25
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229960001413 acetanilide Drugs 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000004090 dissolution Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000007789 gas Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- 238000005119 centrifugation Methods 0.000 abstract 1
- 238000003828 vacuum filtration Methods 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- BLSVPYKVWQSXKY-UHFFFAOYSA-N O1N=CC=C1.CC1=CC=CC=C1 Chemical compound O1N=CC=C1.CC1=CC=CC=C1 BLSVPYKVWQSXKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
- 229960001544 sulfathiazole Drugs 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for producing p-acetamidobenzene sulfonyl chloride. The process comprises: adding chlorosulfonic acid and antifebrine into acetanilide serving as a raw material to perform chlorosulfonation to obtain sulfonated oil; adding water into the obtained sulfonated oil to perform a hydrolysis reaction; subjecting the product of the hydrolysis of sulfonated oil to vacuum filtration; circularly absorbing one hydrogen chloride gas product to prepare diluted hydrochloric acid; and dissolving the other p-acetamidobenzene sulfonyl chloride product in a dissolving kettle, crystallizing, centrifuging and drying to obtain finished p-acetamidobenzene sulfonyl chloride. The process is characterized in that: dichloroethane is added in the dissolution process as a solvent, the finished product obtained after centrifugation is dried by air flow and then packed under vacuum, and thus, the finished product is obtained. In the production process disclosed by the invention, the mass ratio of the added dichloroethane solvent and the acetanilide raw material is (4-8):1, air flow is used for drying, the quality guarantee period of the prepared finished product is as long as 180 days, and the finished product is more stable.
Description
Technical field
The present invention relates to a kind of production technique for preparing p-acetaminobenzenesulfonyl chloride by sulphonated oil.
Background technology
P-acetaminobenzenesulfonyl chloride is a medicine intermediate, is the main raw materials of sulfamidos medicine such as preparation sulfanilamide (SN) toluene isoxazole and Sulphathiazole, and at present domestic all is to be main to use by oneself; Prepare uses that feed intake at once of wet article, otherwise will decompose, rotten, reach the stable time limit of guaranteeing the quality at most also with regard to just three days; Really as commodity; Still blank at present on market, main cryodrying technical equipment and the spray granulating and drying of adopting of external production makes finished product, but additive is to reacting influential.Development trend is to adopt cryodrying to help making the stability of product, but invests bigger.
Summary of the invention
Technical problem to be solved by this invention provides a kind of raising product stability, the production technique of the p-acetaminobenzenesulfonyl chloride that extends the shelf life.
The present invention solves the technical scheme that its technical problem takes: a kind of production technique of p-acetaminobenzenesulfonyl chloride, its production technique are raw material with the Acetanilide, add chlorsulfonic acid and pass through chlorosulfonation with the acetanilide and make sulphonated oil; The sulphonated oil that makes adds water, the reaction that is hydrolyzed, and the sulphonated oil after the hydrolysis is through the suction filtration process; The a hydrogen chloride gas that produces; Hydrogen chloride gas absorbs through circulation and makes Hydrogen chloride, and the product p-acetaminobenzenesulfonyl chloride that another part makes dissolves in dissolution kettle, after crystallization, centrifugal, dry; Make the p-acetaminobenzenesulfonyl chloride finished product; It is characterized in that: add the ethylene dichloride solvent in the said dissolution process, the finished product that makes after centrifugal adopts air stream drying, vacuum-packed finished product.
In order to obtain prolonged period quality guaranteed period of better effect, the employing amount mass ratio of said ethylene dichloride solvent and raw material Acetanilide, Acetanilide: ethylene dichloride=1:4～8.
In the specific embodiment, the quality proportioning that reaches beneficial effect is: said Acetanilide: the mass ratio of ethylene dichloride is 1:5.
In the specific embodiment, the quality proportioning that reaches beneficial effect is: said Acetanilide: the mass ratio of ethylene dichloride is 1:6.
The invention has the beneficial effects as follows: the ethylene dichloride solvent of adding; Use guarantees the stability of p-acetaminobenzenesulfonyl chloride solution in the dissolution process process, the p-acetaminobenzenesulfonyl chloride finished product of processing can be guaranteed the quality about 180 days; Fill up the market vacancy, improved economic benefit.
Description of drawings:
Fig. 1 is a production technique synoptic diagram of the present invention.
Embodiment
With reference to process flow sheet shown in Figure 1, a kind of production technique of p-acetaminobenzenesulfonyl chloride, its production technique are raw material with the Acetanilide; Add chlorsulfonic acid and acetanilide and make sulphonated oil through chlorosulfonation, the sulphonated oil that makes adds water, and reaction is hydrolyzed; Sulphonated oil after the hydrolysis is through the suction filtration process, and a hydrogen chloride gas that produces, hydrogen chloride gas absorb through circulation and make Hydrogen chloride; The product p-acetaminobenzenesulfonyl chloride that another part makes dissolves in dissolution kettle; After crystallization, centrifugal, dry makes the p-acetaminobenzenesulfonyl chloride finished product, it is characterized in that: add the ethylene dichloride solvent in the said dissolution process; The finished product that makes after centrifugal adopts air stream drying, vacuum-packed finished product.The employing amount mass ratio of said ethylene dichloride solvent and raw material Acetanilide, Acetanilide: ethylene dichloride=1:4～8.
In the specific embodiment 1, the quality proportioning that reaches beneficial effect is: said Acetanilide: the mass ratio of ethylene dichloride is 1:5.
In the specific embodiment 2, the quality proportioning that reaches beneficial effect is: said Acetanilide: the mass ratio of ethylene dichloride is 1:6.
The ethylene dichloride solvent that adds uses in the dissolution process process, guarantees the stability of p-acetaminobenzenesulfonyl chloride solution, and the p-acetaminobenzenesulfonyl chloride finished product of processing can be guaranteed the quality about 180 days, had filled up the market vacancy, had improved economic benefit.
The major technique quality index of p-acetaminobenzenesulfonyl chloride:
| Sequence number | Title | Desired value |
| 1 | Outward appearance | White to off-white color, crystalline powder |
| 2 | Content | ≥98% |
| 3 | Moisture | ≤0.5% |
| 4 | Acidity | ≤1.0ml/0.1mol-NaOH/g |
| 5 | Fusing point | 143-147℃ |
| 6 | Quality guaranteed period | 180 days |
| 7 | Store and transportation | Temperature<=25 ℃; Humidity<=50% |
Claims (4)
1. the production technique of a p-acetaminobenzenesulfonyl chloride, its production technique is raw material with the Acetanilide, adds chlorsulfonic acid and passes through chlorosulfonation with the acetanilide and make sulphonated oil; The sulphonated oil that makes adds water, the reaction that is hydrolyzed, and the sulphonated oil after the hydrolysis is through the suction filtration process; The a hydrogen chloride gas that produces, hydrogen chloride gas absorb through circulation and make Hydrogen chloride, and the product p-acetaminobenzenesulfonyl chloride that another part makes dissolves in dissolution kettle; After crystallization, centrifugal, dry; Make the p-acetaminobenzenesulfonyl chloride finished product, it is characterized in that: add the ethylene dichloride solvent in the said dissolution process, the finished product that makes after centrifugal adopts air stream drying.
2. the production technique of p-acetaminobenzenesulfonyl chloride according to claim 1 is characterized in that: the employing amount mass ratio of said ethylene dichloride solvent and raw material Acetanilide, Acetanilide: ethylene dichloride=1:4～8.
3. the production technique of p-acetaminobenzenesulfonyl chloride according to claim 2, it is characterized in that: said Acetanilide: the mass ratio of ethylene dichloride is 1:5.
4. the production technique of p-acetaminobenzenesulfonyl chloride according to claim 2, it is characterized in that: said Acetanilide: the mass ratio of ethylene dichloride is 1:6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110110232A CN102304070A (en) | 2011-04-29 | 2011-04-29 | Process for producing p-acetamidobenzene sulfonyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110110232A CN102304070A (en) | 2011-04-29 | 2011-04-29 | Process for producing p-acetamidobenzene sulfonyl chloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102304070A true CN102304070A (en) | 2012-01-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110110232A Pending CN102304070A (en) | 2011-04-29 | 2011-04-29 | Process for producing p-acetamidobenzene sulfonyl chloride |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103694151A (en) * | 2013-11-22 | 2014-04-02 | 浙江海昇化学有限公司 | Method for direct synthesis of p-acetamidobenzene sulfonyl chloride dried product by solvent extraction |
| CN106866466A (en) * | 2017-02-16 | 2017-06-20 | 吴赣药业（苏州）有限公司 | A kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide |
| CN108530324A (en) * | 2018-06-12 | 2018-09-14 | 新乡市锦源化工有限公司 | The production technology and N-acetylsulfanilyl chloride of high-purity N-acetylsulfanilyl chloride |
| CN108640859A (en) * | 2018-06-12 | 2018-10-12 | 新乡市锦源化工有限公司 | The high-efficiency synthesis method and N-acetylsulfanilyl chloride of N-acetylsulfanilyl chloride |
| CN113563234A (en) * | 2021-07-05 | 2021-10-29 | 佛山市南海北沙制药有限公司 | Production process of p-acetamido-benzenesulfonyl chloride |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996541A (en) * | 1958-10-03 | 1961-08-15 | Berkeley Chemical Corp | Purification of p (nu-acetyl amino) benzene sulfonyl chloride |
| US3595913A (en) * | 1969-05-12 | 1971-07-27 | American Cyanamid Co | Crystallization of acetylsulfanilyl chloride |
| US3649686A (en) * | 1969-05-12 | 1972-03-14 | American Cyanamid Co | Continuous process for the preparation of acylsulfanilyl chloride |
| CN1683331A (en) * | 2004-04-16 | 2005-10-19 | 黄升 | Process for producing sulfanilic amide medicine mother substance p-acetamido benzene sulfonyl chloride |
-
2011
- 2011-04-29 CN CN201110110232A patent/CN102304070A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996541A (en) * | 1958-10-03 | 1961-08-15 | Berkeley Chemical Corp | Purification of p (nu-acetyl amino) benzene sulfonyl chloride |
| US3595913A (en) * | 1969-05-12 | 1971-07-27 | American Cyanamid Co | Crystallization of acetylsulfanilyl chloride |
| US3649686A (en) * | 1969-05-12 | 1972-03-14 | American Cyanamid Co | Continuous process for the preparation of acylsulfanilyl chloride |
| CN1683331A (en) * | 2004-04-16 | 2005-10-19 | 黄升 | Process for producing sulfanilic amide medicine mother substance p-acetamido benzene sulfonyl chloride |
Non-Patent Citations (2)
| Title |
|---|
| 孟歌: "对乙酰氨基苯磺酰氯合成工艺改进", 《开封医专学报》 * |
| 顾林建: "制备对-乙酰胺基苯磺酰氯干品工艺的研究", 《上海化工》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103694151A (en) * | 2013-11-22 | 2014-04-02 | 浙江海昇化学有限公司 | Method for direct synthesis of p-acetamidobenzene sulfonyl chloride dried product by solvent extraction |
| CN103694151B (en) * | 2013-11-22 | 2016-01-20 | 浙江海昇化学有限公司 | The method of p-acetaminobenzenesulfonyl chloride dry product is directly synthesized in a kind of solvent extraction |
| CN106866466A (en) * | 2017-02-16 | 2017-06-20 | 吴赣药业（苏州）有限公司 | A kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide |
| CN108530324A (en) * | 2018-06-12 | 2018-09-14 | 新乡市锦源化工有限公司 | The production technology and N-acetylsulfanilyl chloride of high-purity N-acetylsulfanilyl chloride |
| CN108640859A (en) * | 2018-06-12 | 2018-10-12 | 新乡市锦源化工有限公司 | The high-efficiency synthesis method and N-acetylsulfanilyl chloride of N-acetylsulfanilyl chloride |
| CN113563234A (en) * | 2021-07-05 | 2021-10-29 | 佛山市南海北沙制药有限公司 | Production process of p-acetamido-benzenesulfonyl chloride |
| CN113563234B (en) * | 2021-07-05 | 2023-06-23 | 佛山市南海北沙制药有限公司 | Production process of acetamido benzene sulfonyl chloride |
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Application publication date: 20120104 |