CN1663948A - Process for preparing anhydrous p-cetylsulphanilyl chloride - Google Patents
Process for preparing anhydrous p-cetylsulphanilyl chloride Download PDFInfo
- Publication number
- CN1663948A CN1663948A CN 200410082350 CN200410082350A CN1663948A CN 1663948 A CN1663948 A CN 1663948A CN 200410082350 CN200410082350 CN 200410082350 CN 200410082350 A CN200410082350 A CN 200410082350A CN 1663948 A CN1663948 A CN 1663948A
- Authority
- CN
- China
- Prior art keywords
- stirring
- mixture
- crystallization
- stirring velocity
- rev
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing anhydrous p-acetamido-sulfonyl chloride, which includes: (1) adding a 8:1~16:1 in mass mixture of tri-chloromethane or the mixture of tri-chloromethane and water and hydrous p-acetamido-sulfonyl chloride, keeping stirring and heating until dissolved, the temperature is 35-60 DEG C, the stirring velocity 100-300 rotes per minute, and for 1-2 hours; (2) removing the water layer, stirring and cooling the organic layer in the tank of crystallization, the temperature is 0-20 DEG C, the stirring velocity 5-70 rotes per minute, and for 1-6 hours, filtering the crystalline mixed liquid, and vacuum drying the crystallization. The invention is characterized by low price of the used dissolvent and slight quantity; the filtrate (dissolvent) can be reused without refining, which has no effect on the product quality, and by the high yield with the purity more than 99.9%.
Description
Technical field
The present invention relates to a kind of preparation method of anhydrous p-acetaminobenzenesulfonyl chloride.
Background technology
P-acetaminobenzenesulfonyl chloride is a kind of important medicine, dyestuff, industrial chemicals.It is the intermediate of industrial sulfanilamide (SN) and sulfa drugs, also is the intermediates of reactive dyestuffs to chloro-beta-hydroxyethyl sulfone sulfate, also can be used as the raw material of polysulfones engineering moulding mixture, and purposes is extremely extensive.Patent CN1384099A (2002) has reported the synthetic method of high yield p-acetaminobenzenesulfonyl chloride.Because the character of p-acetaminobenzenesulfonyl chloride is not really stable, meets water and easily decompose.Therefore, the method for utilizing production limit, limit to use usually satisfies the production demand.
Anhydrous p-acetaminobenzenesulfonyl chloride stable in properties, but standing storage never degenerate, for the long-distance transport of product and storage etc. provide very big convenience.Preparation for anhydrous p-acetaminobenzenesulfonyl chloride is made solvent just like patent HU57715 (1991) with isopropylcarbinol; JP6378 (60) makes methods such as solvent with ethyl acetate, its shortcoming is that yield is low, the solvent valency is expensive, cost is high.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of anhydrous p-acetaminobenzenesulfonyl chloride.
The step of method is as follows:
1) adding mass ratio in reactor is: 8: 1-16: the mixture of 1 trichloromethane or trichloromethane and water and moisture p-acetaminobenzenesulfonyl chloride, warming while stirring is until dissolving, temperature is 35 ℃-60 ℃, and stirring velocity is 100-300 rev/min, and churning time is 1-2 hour;
2) branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 0-20 ℃, and stirring velocity is 5-70 rev/min, and churning time is 1-6 hour, and crystallization mixture is filtered, and crystallization gets final product through vacuum-drying.
Advantage of the present invention is: the solvent for use price is low, and consumption is few, and filtrate (solvent) need not made with extra care promptly reusable, does not influence quality product simultaneously, the product yield height, and purity is greater than 99.9%.
Embodiment
The preparation method's of anhydrous p-acetaminobenzenesulfonyl chloride step is as follows:
1) adding mass ratio in reactor is: 10: 1-14: the mixture of 1 trichloromethane or trichloromethane and water and moisture p-acetaminobenzenesulfonyl chloride, warming while stirring is until dissolving, temperature is 50 ℃-60 ℃, and stirring velocity is 100-300 rev/min, and churning time is 1-2 hour;
2) branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 5-10 ℃, stirring velocity is 5-15 rev/min, and churning time is 2-4 hour, and crystallization mixture is filtered, crystallization gets final product through vacuum-drying, and filtrate (solvent) need not made with extra care promptly reusable.
(purity: 61.13%, moisture 38.87%) method according to CN1384099A (2002) patent working example 1 prepares p-acetaminobenzenesulfonyl chloride.Its preparation method is: 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; inject the frozen water of 1500 parts of trash ices and 1000 parts of water then lentamente, hydrolysis; crystallization; suction filtration; washing; vacuum filtration gets 225.3 parts of products.
Embodiment 1
Adding mass ratio in reactor is: 8: 1 trichloromethane and p-acetaminobenzenesulfonyl chloride, warming while stirring are until dissolving, and temperature is 35 ℃, and stirring velocity is 100 rev/mins, churning time 1 hour; Branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 0 ℃, and stirring velocity is 5 rev/mins, and churning time 4 hours is filtered crystallization mixture, drains, and crystallization gets final product through vacuum-drying.
Embodiment 2
Adding mass ratio in reactor is: 16: 1 trichloromethane and p-acetaminobenzenesulfonyl chloride, warming while stirring are until dissolving, and temperature is 60 ℃, and stirring velocity is 3Q0 rev/min, churning time 2 hours; Branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 20 ℃, and stirring velocity is 70 rev/mins, and churning time 6 hours is filtered crystallization mixture, drains, and crystallization gets final product through vacuum-drying.
Embodiment 3
Adding mass ratio in reactor is: 14: 1 trichloromethane and p-acetaminobenzenesulfonyl chloride, warming while stirring are until dissolving, and temperature of reaction is 55 ℃, and stirring velocity is 150 rev/mins, churning time 1.5 hours; Branch vibration layer, organic layer stirs crystallisation by cooling in crystallizer tank, Tc is 5 ℃, and stirring velocity is 10 rev/mins, churning time 3 hours, crystallization mixture is filtered, drain, crystallization is through vacuum-drying, purity 99.99%, yield is 87.70%, and filtrate (solvent) need not made with extra care promptly reusable.
Embodiment 4
Adding mass ratio in reactor is: 8: 1 trichloromethane and the mixture of water and p-acetaminobenzenesulfonyl chloride, warming while stirring are until dissolving, and temperature is 35 ℃, and stirring velocity is 100 rev/mins, churning time 1 hour; Branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 0 ℃, and stirring velocity is 5 rev/mins, and churning time 4 hours is filtered crystallization mixture, drains, and crystallization gets final product through vacuum-drying.
Embodiment 5
Adding mass ratio in reactor is: 16: 1 trichloromethane and the mixture of water and p-acetaminobenzenesulfonyl chloride, warming while stirring are until dissolving, and temperature is 60 ℃, and stirring velocity is 300 rev/mins, churning time 2 hours; Branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 20 ℃, and stirring velocity is 70 rev/mins, and churning time 6 hours is filtered crystallization mixture, drains, and crystallization gets final product through vacuum-drying.
Embodiment 6
Adding mass ratio in reactor is: 13: 1 trichloromethane and the mixture of water and p-acetaminobenzenesulfonyl chloride, warming while stirring are until dissolving, and temperature of reaction is 55 ℃, and stirring velocity is 150 rev/mins, churning time 1.5 hours; Branch vibration layer, organic layer stirs crystallisation by cooling in crystallizer tank, Tc is 5 ℃, and stirring velocity is 10 rev/mins, churning time 3 hours, crystallization mixture is filtered, drain, crystallization is through vacuum-drying, purity 99.99%, yield is 81.30%, and filtrate (solvent) need not made with extra care promptly reusable.
Claims (3)
1. the preparation method of an anhydrous p-acetaminobenzenesulfonyl chloride is characterized in that, the step of method is as follows:
1) adding mass ratio in reactor is: 8: 1-16: the mixture of 1 trichloromethane or trichloromethane and water and moisture p-acetaminobenzenesulfonyl chloride, warming while stirring is until dissolving, temperature of reaction is 35 ℃-60 ℃, and stirring velocity is 100-300 rev/min, and churning time is 1-2 hour;
2) branch vibration layer, organic layer stir crystallisation by cooling in crystallizer tank, Tc is 0-20 ℃, and stirring velocity is 5-70 rev/min, and churning time is 1-6 hour, and crystallization mixture is filtered, and crystallization gets final product through vacuum-drying.
2. the preparation method of a kind of anhydrous p-acetaminobenzenesulfonyl chloride according to claim 1, it is characterized in that, it is characterized in that, the mass ratio of the mixture of trichloromethane or trichloromethane and water and p-acetaminobenzenesulfonyl chloride is in the described step 1): 10: 1-14: 1, and temperature of reaction is 50 ℃-60 ℃.
3. the preparation method of a kind of anhydrous p-acetaminobenzenesulfonyl chloride according to claim 1 is characterized in that, described step 2) in Tc be 5-10 ℃, stirring velocity is 5-15 rev/min, churning time is 2-4 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410082350 CN1277815C (en) | 2004-12-31 | 2004-12-31 | Process for preparing anhydrous p-cetylsulphanilyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410082350 CN1277815C (en) | 2004-12-31 | 2004-12-31 | Process for preparing anhydrous p-cetylsulphanilyl chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1663948A true CN1663948A (en) | 2005-09-07 |
| CN1277815C CN1277815C (en) | 2006-10-04 |
Family
ID=35035283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410082350 Expired - Fee Related CN1277815C (en) | 2004-12-31 | 2004-12-31 | Process for preparing anhydrous p-cetylsulphanilyl chloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1277815C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101613308B (en) * | 2009-07-24 | 2013-08-14 | 重庆大学 | Method for synthesizing p-acetamido benzene sulfonyl chloride by phosphorus pentachloride |
-
2004
- 2004-12-31 CN CN 200410082350 patent/CN1277815C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101613308B (en) * | 2009-07-24 | 2013-08-14 | 重庆大学 | Method for synthesizing p-acetamido benzene sulfonyl chloride by phosphorus pentachloride |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1277815C (en) | 2006-10-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102329212A (en) | Refining method for long-chain binary acid | |
| CN102268016A (en) | Method for preparing amoxicillin sodium | |
| CN102408364B (en) | Method for preparing paratoluensulfonyl chloride | |
| CN1277815C (en) | Process for preparing anhydrous p-cetylsulphanilyl chloride | |
| CN1304684C (en) | Synthesis technology of polyester dying modifier SIPM | |
| CN110713441A (en) | Synthesis method of oxadiazon intermediate 2, 4-dichloro-5-nitrophenol | |
| CN106316921B (en) | A kind of preparation method of acemetacin | |
| CN1214989C (en) | New cleaning technology of chromic acid anhydride and nitric acid anhydride joint production | |
| CN104230764A (en) | Preparation method of 2-acrylamide-2-methyl propanesulfonic acid | |
| CN111574459B (en) | Preparation method of metronidazole | |
| CN1037428C (en) | Method for producing potassium sulfate by double decomposition of sodium sulfate and potassium chloride | |
| CN102010345A (en) | Method for preparing D-phenylalanine through dynamic kinetic resolution | |
| CN101161636B (en) | Method for purifying capsicine | |
| CN1106391A (en) | Preparation of 5-acetoactylaminobenzimidazolon-2 | |
| CN1143845C (en) | Prepn of amidobenzene sulfonyl chloride | |
| CN104370734B (en) | The synthetic method of the menbutone improved | |
| CN107827821B (en) | Continuous flow clean production process of pyrazolone series products | |
| CN1143844C (en) | Prepn of nitrobenzene sulfonyl chloride | |
| CN101066929A (en) | Process of preparing 4-amino-3-nitro phenol | |
| CN109438270B (en) | Preparation method of di (p-N, N-dialkyl aminobenzoic acid) -N-alkyl diethanol amine ester | |
| CN104086406A (en) | Method for separating and recycling sodium oxalate from waste water containing oxalic acid | |
| CN114149403B (en) | Mixed crystal form glycolide and preparation method and application thereof | |
| CN1436773A (en) | Synthesis process of tolylsulfonyl chloride | |
| CN1100041C (en) | Preparation of magnesium [(1,5-dimethyl-2-phenyl-3-oxy-2,3-dioxy-1H-pyrazol-4-yl)methylamino] methane sulfonate hexahydrate | |
| TWI535659B (en) | The purification method of alkali-metal sulfate compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |