CN1384099A - Prepn of amidobenzene sulfonyl chloride - Google Patents
Prepn of amidobenzene sulfonyl chloride Download PDFInfo
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- CN1384099A CN1384099A CN 01117742 CN01117742A CN1384099A CN 1384099 A CN1384099 A CN 1384099A CN 01117742 CN01117742 CN 01117742 CN 01117742 A CN01117742 A CN 01117742A CN 1384099 A CN1384099 A CN 1384099A
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Abstract
Amidobenzene sulfonyl chloride is prepared through the reaction of acetanilide or formanilide in 1 mol as raw material, chlorosulfonic acid in 2.0-5.5 mol as sulfonating agent, acidylating agent P2O5 in 0.04-0.70 mol and sulfonating assistant in 0.001-0.35 mol at normal pressure and 10-60 deg.c for 2-6 hr and subsequet cooling, hydrolysis, crystallization, suction filtering, water washing and drying. The advantages of the present invention are low chlorosulfonic acid consumption high product yield and purity, less sulfonating assistant and acidylating agent consumption, low cost and less environmental pollution.
Description
The present invention relates to aromatic hydrocarbon and derivative compound thereof, relate in particular to a kind of preparation method of amidobenzene sulfonyl chloride.
P-acetaminobenzenesulfonyl chloride is a kind of important medicine, dyestuff, industrial chemicals, it is the intermediate of industrial sulfanilamide (SN) and sulfa drugs, also be the intermediates of reactive dyestuffs to amino-beta--hydroxyethyl sulfone, the raw material that also can be used as the polysulfones engineering plastics, purposes is extremely extensive, generally adopts the method for Acetanilide and excess chlorine sulfonic acid reaction and obtains but long reaction time, yield is low, and is seriously polluted.In order to improve above-mentioned shortcoming, carried out big quantity research both at home and abroad, adopt Acetanilide and the reaction of excess chlorine sulfonic acid as US 3.108.137 (1963), use the method for dichloromethane extraction then, yield is low, solvent recuperation cost height, be unfavorable for realizing industrialization, US 3,649 686 (1972) adopts the pipeline reactor method, Acetanilide and chlorsulfonic acid quantitatively drop into reactor respectively, and add proper amount of surfactant, quantitatively take out behind the stop certain hour in pipeline reactor, but yield low (80%) cost height also is unsuitable for industrialization; EP 403.947 (1990) adopts sulfur oxychloride to make acylating agent; because the mol ratio height of Acetanilide and sulfur oxychloride; the acylating agent valency is expensive etc., so the cost height, industrialization is restricted; in sum; their common drawback is that yield is low, and the acylating agent valency is expensive, the cost height; the chlorsulfonic acid consumption is big, and the spent acid after the superfluous chlorsulfonic acid hydrolysis causes serious environmental to pollute.
The purpose of this invention is to provide a kind of high yield, high purity, low cost, reduce the preparation method of the amidobenzene sulfonyl chloride of environmental pollution.
In order to achieve the above object, the present invention takes following measures:
The preparation method of amidobenzene sulfonyl chloride; with Acetanilide or formylaniline is raw material for 1 mole; 2.0～5.5 moles of sulphonating agent chlorsulfonic acids; react under 0.04～0.70 mole of acylating agent Vanadium Pentoxide in FLAKES, 0.00 1～0.35 mole of effect of sulfonation auxiliary agent; reaction pressure is a normal pressure, and temperature of reaction is 10～60 ℃, and the reaction times is 2～6 hours; after reaction finishes, through cooling, hydrolysis, crystallization, suction filtration, washing, dry getting final product.
Advantage of the present invention is: the chlorsulfonic acid consumption is few, product yield and purity height, and acylating agent and sulfonation auxiliary dosage are low, inexpensive, reduce cost, and reduce environmental pollution.
Below in conjunction with embodiment the present invention is elaborated.
The preparation method of amidobenzene sulfonyl chloride is being raw material for 1 mole to Acetanilide or formylaniline; 2.5～4.5 moles of sulphonating agent chlorsulfonic acids; through 0.15～0.55 mole of acylating agent Vanadium Pentoxide in FLAKES, 0.01～0.2 mole of effect of sulfonation auxiliary agent reaction down; reaction pressure is a normal pressure; temperature of reaction is 10～60 ℃; reaction times is 2～5 hours, after reaction finishes, through cooling, hydrolysis, crystallization, suction filtration, washing, dry getting final product.
The sulfonation auxiliary agent is a kind of in ammonium sulfate, ammonium chloride, the thionamic acid or their mixture, and its consumption is 0.01～0.2 mole.
Embodiment 1
Having agitator; thermometer; in 500 milliliters the four-hole boiling flask of outlet port and charging opening; add 446.3 parts of chlorsulfonic acids; be added dropwise to 135.6 parts of Acetanilides while stirring; temperature≤35 ℃; add sulfonation auxiliary agent (ammonium sulfate; ammonium chloride; a kind of in the thionamic acid or their mixture; as follows) 1.8 parts; 80 parts of acylating agent Vanadium Pentoxide in FLAKESs; behind reinforced the end; 35 ℃ of following constant temperature stirring reactions 30 minutes; be warmed up to again under 55～60 ℃ of stirrings and reacted 2 hours; reaction progressively is cooled to sulfonated liquid about 20 ℃ after finishing, and injects the frozen water of 1500 parts of trash ices and 1000 parts of water then lentamente, hydrolysis; crystallization; suction filtration; washing; get 225.3 parts of products after the drying; yield 96.4%, purity 97.5%.
Comparative Examples 1: add 574.8 parts of chlorsulfonic acids in 500 milliliters of four-hole boiling flasks, 135.6 parts of Acetanilides do not add acylating agent Vanadium Pentoxide in FLAKES and sulfonation auxiliary agent, and other operation conditions get 184.3 parts of products, yield 78.5%, purity 92.3% with embodiment 1.
Embodiment 2
Having agitator; thermometer; in 500 milliliters the four-hole boiling flask of outlet port and charging opening; add 446.3 parts of chlorsulfonic acids; under 20 ℃, slowly add 121.2 parts of formylanilines while stirring; add 2 parts of sulfonation auxiliary agents; 78.4 parts of acylating agent Vanadium Pentoxide in FLAKESs; reinforced finishing; 30 ℃ of following stirring reactions 30 minutes; be warmed up to 55～60 ℃ of constant temperature then and stir reaction down 2 hours; reaction progressively is cooled to sulfonated liquid about 20 ℃ after finishing, and then sulfonated liquid is injected lentamente 2500 parts of mixture of ice and water, hydrolysis; crystallization; suction filtration; washing; get 214.2 parts of products after the drying; yield 97.5%, purity 95.1%.
Comparative Examples 2: in 500 milliliters of four-hole boiling flasks, add 574.8 parts of chlorsulfonic acids, add 121.2 parts of formylanilines lentamente, do not add acylating agent Vanadium Pentoxide in FLAKES and sulfonation auxiliary agent; other operation conditions are with embodiment 2; get 174.7 parts of products, yield 79.5%, purity 91.3% at last.
Embodiment 3
To the preparation method of amidobenzene sulfonyl chloride is to be raw material with 1 mole of Acetanilide; 2.0 moles of chlorsulfonic acids is sulphonating agent; react under 0.70 mole of acylating agent, 0.001 mole of effect of sulfonation auxiliary agent; reaction pressure is a normal pressure; temperature of reaction is 60 ℃; reaction times is 2 hours, after reaction finishes, through cooling, hydrolysis, crystallization, suction filtration, washing, dry getting final product.
Embodiment 4
To the preparation method of amidobenzene sulfonyl chloride is to be raw material with 1 mole of formylaniline; 5.0 moles of sulphonating agent chlorsulfonic acids; react under 0.04 mole of acylating agent, 0.35 mole of effect of sulfonation auxiliary agent; reaction pressure is a normal pressure; temperature of reaction is 60 ℃; reaction times is 6 hours, after reaction finishes, through cooling, hydrolysis, crystallization, suction filtration, washing, dry getting final product.
Claims (5)
1. the preparation method of an amidobenzene sulfonyl chloride; it is characterized in that: with Acetanilide or formylaniline is raw material for 1 mole; 2.0～5.5 moles of sulphonating agent chlorsulfonic acids; react under 0.04～0.70 mole of acylating agent Vanadium Pentoxide in FLAKES, 0.001～0.35 mole of effect of sulfonation auxiliary agent; reaction pressure is a normal pressure, and temperature of reaction is 10～60 ℃, and the reaction times is 2～6 hours; after reaction finishes, through cooling, hydrolysis, crystallization, suction filtration, washing, dry getting final product.
2. the preparation method of a kind of amidobenzene sulfonyl chloride according to claim 1 is characterized in that said chlorsulfonic acid is 2.5～4.5 moles, and the sulfonation auxiliary agent is 0.01～0.2 mole.
3. the preparation method of a kind of amidobenzene sulfonyl chloride according to claim 1 and 2 is characterized in that the said reaction times is 2～5 hours.
4. the preparation method of a kind of amidobenzene sulfonyl chloride according to claim 1 and 2 is characterized in that said sulfonation auxiliary agent is a kind of in ammonium sulfate, ammonium chloride, the thionamic acid or their mixture, and its consumption is 0.01～0.20 mole.
5. the preparation method of a kind of amidobenzene sulfonyl chloride according to claim 1 and 2 is characterized in that said acylating agent is a Vanadium Pentoxide in FLAKES, 0.15～0.55 mole of acylating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB01117742XA CN1143845C (en) | 2001-04-30 | 2001-04-30 | Prepn of amidobenzene sulfonyl chloride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB01117742XA CN1143845C (en) | 2001-04-30 | 2001-04-30 | Prepn of amidobenzene sulfonyl chloride |
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| Publication Number | Publication Date |
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| CN1384099A true CN1384099A (en) | 2002-12-11 |
| CN1143845C CN1143845C (en) | 2004-03-31 |
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| CNB01117742XA Expired - Fee Related CN1143845C (en) | 2001-04-30 | 2001-04-30 | Prepn of amidobenzene sulfonyl chloride |
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Cited By (4)
| 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 |
| CN107556221A (en) * | 2017-10-09 | 2018-01-09 | 新乡市锦源化工有限公司 | The preparation method of para-ester |
| CN109796376A (en) * | 2019-01-24 | 2019-05-24 | 南通远航医药化工有限公司 | A kind of production technology of sulfanilamide (SN) intermediate amidobenzene sulfonyl chloride |
| CN113636961A (en) * | 2021-07-09 | 2021-11-12 | 重庆康乐制药有限公司 | Preparation method of p-acetamidobenzenesulfonyl chloride |
-
2001
- 2001-04-30 CN CNB01117742XA patent/CN1143845C/en not_active Expired - Fee Related
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 |
| 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 |
| CN107556221A (en) * | 2017-10-09 | 2018-01-09 | 新乡市锦源化工有限公司 | The preparation method of para-ester |
| CN109796376A (en) * | 2019-01-24 | 2019-05-24 | 南通远航医药化工有限公司 | A kind of production technology of sulfanilamide (SN) intermediate amidobenzene sulfonyl chloride |
| CN113636961A (en) * | 2021-07-09 | 2021-11-12 | 重庆康乐制药有限公司 | Preparation method of p-acetamidobenzenesulfonyl chloride |
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| Publication number | Publication date |
|---|---|
| CN1143845C (en) | 2004-03-31 |
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