CN102491955A

CN102491955A - Process method for synthesizing 1, 2-benzisothiazdin-3-ketone

Info

Publication number: CN102491955A
Application number: CN201110405814XA
Authority: CN
Inventors: 张静
Original assignee: SHANGHAI YIMO BIOTECHNOLOGY CO Ltd
Current assignee: SHANGHAI YIMO BIOTECHNOLOGY CO Ltd
Priority date: 2011-12-08
Filing date: 2011-12-08
Publication date: 2012-06-13

Abstract

The invention relates to a process method for synthesizing 1, 2-benzisothiazdin-3-ketone, which includes the steps: 1 enabling 2-chlorobenzonitrile and anhydrous sodium sulfide to react, and then performing acidification to obtain o-mercaptobenzonitrile; and 2 enabling the o-mercaptobenzonitrile to react with chlorine and water, cooling, crystallizing and obtaining target products. The process method adopts a 1, 2-benzisothiazdin-3-ketone synthesis method which is completely different from a traditional way, thereby greatly simplifying synthesis steps, lowering cost and reducing environment pollution simultaneously.

Description

A kind of synthetic 1, the process method of 2-benzisothiazole-3-ketone

[technical field]

The invention belongs to the field of chemical synthesis, specifically a kind of synthetic 1, the process method of 2-benzisothiazole-3-ketone.

[background technology]

Sterilant be used to various Application Areass with control or prevent microbial growth, thereby guarantee the preservation of product and material.With 1; 2-benzisothiazole-3-ketone (CAS NR.2634-33-5; Hereinafter to be referred as BIT) for having very widely, uses the industrial bactericide of main raw material, for example in building material industry, textile industry, leather industry, paper industry, electronic industry and foodstuffs industry and makeup and agricultural, be widely used.

At present main with dithio-salicylic acid (DTSA) for raw material prepares 1, the 2-benzisothiazole-3-ketone is referring to Fig. 1.In actual production, can find out from following reaction formula: the chloride meeting of dithio-salicylic acid produces a large amount of form waste gas of sulfur dioxide, can cause the pollution of environment, increases burden to environmental improvement.Can produce a large amount of brine wastes with this route is synthetic simultaneously, and synthesis step is long, cost is high.

Hope to have a kind of novel synthetic 1, the process method of 2-benzisothiazole-3-ketone can overcome the above-mentioned defective that exists in the prior art.

[summary of the invention]

Technical problem to be solved by this invention provides a kind of novel synthetic 1, and the process method of 2-benzisothiazole-3-ketone is to overcome long, the defect of high cost of generation large quantity of exhaust gas, operational path that exists in the prior art.

Technical problem to be solved by this invention can be able to solve through following technological method:

A kind of synthetic 1, the process method of 2-benzisothiazole-3-ketone is characterized in that it comprises the steps:

1) makes the reaction of o-chloro benzonitrile and Sodium sulphate anhydrous, 99min, carry out acidifying then and obtain adjacent sulfydryl benzene nitrile; With

2) adjacent sulfydryl benzene nitrile and chlorine G&W are reacted, crystallisation by cooling obtains target product.

In step 1), the reaction of equation (I) and equation (II) is able to carry out:

equation (I)

equation (II)

In step 2), the reaction of equation (III) is able to carry out:

equation (III)

In one embodiment, being reflected in the N of equation (I) carried out.

In a preferred embodiment, the mol ratio of o-chloro benzonitrile and Sodium sulphate anhydrous, 99min is 1: 1.1, and temperature of reaction is 90 ℃, and the reaction times is 3 hours.

In one embodiment, acidifying adopts hydrochloric acid to carry out in the step 1), makes PH=2.

Being reflected under 10 ℃-20 ℃ step 2 in one embodiment) carried out.

In one embodiment, said method also comprises step 2) title product be further purified.

In one embodiment, said purifying is through handling with alkali lye earlier, and acidifying is followed in decolouring then, separates then and carries out.

In the purge process, for example adopt NaOH solution to handle, below reaction is able to carry out:

equation (IV)

In the purge process, for example adopt that hydrochloric acid carries out acidifying, below reaction is able to carry out:

equation formula V

In one embodiment, said decolouring is carried out under 60 ℃-70 ℃.

In one embodiment, the acidifying in the said purge process is carried out under 30 ℃-40 ℃, keeps the pH value between 3-4.

In one embodiment, the alkali lye in the said purge process is handled and is kept the pH value at about 9-about 10.

The present invention has adopted and has been different from 1 of traditional route fully, and 2-benzisothiazole-3-ketone compound method has been simplified synthesis step greatly, has reduced cost, has reduced environmental pollution simultaneously.

[description of drawings]

Fig. 1 is that prior art is used DTSA preparation 1, the route of 2-benzisothiazole-3-ketone;

Fig. 2 is liquid chromatogram and the data that adopt the finished product of the inventive method preparation;

Fig. 3 is the transmitted light spectrogram that adopts the finished product of the inventive method preparation.

[embodiment]

Through embodiment the present invention is elaborated below, so that the feature and advantage of compound method of the present invention are clearer, but the present invention is not limited to the embodiment that lists among this paper.

In the embodiment of the invention, through liquid chromatography (instrument: FL-2200, post: Hypersil COS2, UV-detector: 254nm) confirm product yield, confirm the structure of end product through ir spectra.

Embodiment 1

In the 1000ml four-hole bottle, add 46.7 gram o-chloro benzonitriles, the logical nitrogen protection of 30 gram Sodium sulphate anhydrous, 99mins and 550ml DMF, reaction is 3 hours under 90 ℃, and reaction finishes; Cooling, with the solvent DMF underpressure distillation, distillation back resistates adds water 500ml, suction filtration; Filtrating is as in the ice-water bath, and to PH=2, yellow oily liquid appears in lower floor, uses ethyl acetate extraction with 10% hcl acidifying; Merge organism, boil off solvent ethyl acetate, obtain product yellow liquid 32 grams.

In the 1000mL four-hole bottle, drop into adjacent sulfydryl benzene nitrile 200 grams, Benzene Chloride 680 grams, water 72 grams are opened and are stirred, cooling, controlled temperature approximately feeds 100 grams at 10 ℃ of-20 ℃ of logical chlorine, and sampling liquid phase analysis raw material peak＜1% o'clock stops logical chlorine; If raw material peak＞1% continues logical chlorine, until raw material peak＜1%.Slowly be warming up to 60 ℃ then, be incubated 1 hour, be cooled to 25 ℃-30 ℃ again, suction filtration obtains bullion BIT, reclaims Benzene Chloride simultaneously.

A collection of bullion is dropped in the 1000mL four-hole bottle, add water 200 grams, open and stir; Heating up adds liquid caustic soda, regulates the pH value about 9-10, stirs 30 minutes; Static layering then, lower floor's feed liquid add gac decolours, and controlled temperature is between 60 ℃-70 ℃ degrees centigrade; The upper strata chlorobenzene layer reclaims.

The feed liquid that decolouring is good is carried out acidifying with the filtering hydrochloric acid of process, and controlled temperature is between 30 ℃-40 ℃, and the pH value is between 3-4; After acidifying is good, suction filtration, oven dry; Get target product 1; 2-benzisothiazole-3-ketone, its liquid chromatography and data are seen Fig. 2 (yield is 99.49%), and infrared spectrogram is seen Fig. 3.

More than through embodiment the inventive method is illustrated, can find out that the present invention has overcome prior art and produced large quantity of exhaust gas, long, the defect of high cost of operational path.

Claims

1. one kind is synthesized 1, and the process method of 2-benzisothiazole-3-ketone is characterized in that it comprises the steps:

2. method according to claim 1 is characterized in that said method also comprises step 2) title product be further purified.

3. method according to claim 1 and 2 is characterized in that, being reflected in the N of o-chloro benzonitrile and Sodium sulphate anhydrous, 99min carried out.

4. method according to claim 1 and 2 is characterized in that, the mol ratio of o-chloro benzonitrile and Sodium sulphate anhydrous, 99min is 1: 1.1, and temperature of reaction is 90 ℃, and the reaction times is 3 hours.

5. method according to claim 1 and 2 is characterized in that, acidifying adopts hydrochloric acid to carry out in step 1), makes PH=2.

6. method according to claim 1 and 2 is characterized in that, according to step 2) in be reflected under 10 ℃-20 ℃ and carry out.

7. method according to claim 2 is characterized in that, said purifying is through handling with alkali lye earlier, and acidifying is followed in decolouring then, separates then and carries out.

8. method according to claim 7 is characterized in that, said decolouring is carried out under 60 ℃-70 ℃.

9. according to claim 7 or 8 described methods, it is characterized in that the acidifying in the said purge process is carried out under 30 ℃-40 ℃, keep the pH value between 3-4.

10. according to claim 7 or 8 described methods, it is characterized in that the alkali lye in the said purge process is handled and kept the pH value at about 9-about 10.