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CN105753805A - Method for purifying 1,2-benzisothiazole-3-ketone - Google Patents

Method for purifying 1,2-benzisothiazole-3-ketone Download PDF

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Publication number
CN105753805A
CN105753805A CN201610196128.9A CN201610196128A CN105753805A CN 105753805 A CN105753805 A CN 105753805A CN 201610196128 A CN201610196128 A CN 201610196128A CN 105753805 A CN105753805 A CN 105753805A
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China
Prior art keywords
ketone
benzisothiazole
purification
polar solven
snow
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CN201610196128.9A
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Chinese (zh)
Inventor
戴明本
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SHOUGUANG XINTAI FINE CHEMICAL CO Ltd
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SHOUGUANG XINTAI FINE CHEMICAL CO Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D275/00Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

The invention relates to the field of fine chemical engineering, in particular to a method for purifying 1,2-benzisothiazole-3-ketone.The method includes the following steps that 1, a non-polar solvent and 1,2-benzisothiazole-3-ketone are mixed, and the temperature is increased till the mixture is completely dissolved, wherein the non-polar solvent is preferably toluene or chlorobenzene or o-xylene or o-dichlorobenzene, and the mass ratio of the 1,2-benzisothiazole-3-ketone to the non-polar solvent is 1.5-20; 2, cooling is carried out, the temperature is reduced to 20 DEG C-25 DEG C, heat preservation is carried out for 30 min, filtering is carried out, a 1,2-benzisothiazole-3-ketone crystal is obtained, washed with cold water and dried, and the snow-white particles 1,2-benzisothiazole-3-ketone are obtained.Compared with the prior art, acid, base and a large amount of water can be avoided, pollution is reduced, the quality of the product is good, the content and the yield are high, post-treatment of the solvent is simple, the operating condition is greatly improved, and the method is worthy of application and popularization.

Description

A kind of method of purification of 1,2-benzisothiazole-3-ketone
[technical field]
The invention belongs to field of fine chemical, specifically a kind of 1, the purification side of 2-benzisothiazole-3-ketone Method.
[background technology]
1,2-benzisothiazole-3-ketone (BIT, formula I) is widely used in antibacterial, preservative, its tradition Method of purification be use acid-base method, with a large amount of water as solvent, first with liquid caustic soda dissolve, then with hydrochloric acid separate out, Finally giving 1,2-benzisothiazole-3-ketone powder, this method yield is high.But, this method of purification is deposited In following weak point: not only can produce substantial amounts of brine waste, product quality is low, and dust is many, behaviour Make condition poor.
Patent No. CN201310084775.7 provides a kind of 1, the method for purification of 2-benzisothiazole-3-ketone, Watersoluble polar proton solvent is mixed by it with water makees solvent, and recrystallization is dried gained crystal, although avoid The drawback of traditional handicraft, but yield or relatively low, the most only 90%, it is often more important that, BIT product or Person's crude product is general all with water, or in order to improve recrystallization yield, adds water, and solvent for use is water-soluble Property polar aprotic solvent, then add solvent post-processing difficulty.
Therefore, if being provided that, one is avoided using soda acid and a large amount of water, reduces and pollutes, and good product quality, Content is high, and yield is high, and solvent post processing is simple, greatly improves the 1 of operating condition, 2-benzisothiazole-3- The method of purification of ketone, will have very important significance.
[summary of the invention]
Present invention aim to solve above-mentioned deficiency and a kind of 1,2-benzisothiazole-3-ketone is provided Method of purification, can not only avoid using soda acid and a large amount of water, reduce and pollute, and good product quality, contain Amount height, yield is high.
Design a kind of 1 for achieving the above object, the method for purification of 2-benzisothiazole-3-ketone, including following step Rapid:
1) by non-polar solven and 1,2-benzisothiazole-3-ketone mixes, and is warming up to the most molten;
2) cool, filter 1,2-benzisothiazole-3-ketone crystal, cold water washing after, be dried Gained crystal, obtains snow-white granule 1,2-benzisothiazole-3-ketone.
Step 1) in, described non-polar solven is toluene, chlorobenzene, o-dichlorohenzene, benzene, m-dichlorobenzene, neighbour Dimethylbenzene, meta-xylene, xylol, sym-trimethylbenzene., pseudocumene, amylalcohol, hexanol, enanthol, pungent Alcohol, propyl ether, butyl ether, dichloroethanes, chlorobutane, n-butyl bromide, dimethyl carbonate, diethyl carbonate, carbon One or more combination in acid dipropyl.
Step 1) in, 1,2-benzisothiazole-3-ketone and non-polar solven mass ratio are 1.5-20.
Step 1) in, 1,2-benzisothiazole-3-ketone and non-polar solven mass ratio are 3-6.
Step 1) in, 1,2-benzisothiazole-3-ketone and non-polar solven solution temperature are 40-150 DEG C.
Step 1) in, 1,2-benzisothiazole-3-ketone and non-polar solven solution temperature are 60-120 DEG C.
Step 2) in, cool to 20-25 DEG C, and be incubated 30min.
Step 2) after, also comprising the steps: step 2) gained filtrate divides aqueous phase, decompression distillation Reclaim non-polar solven, input 1,2-benzisothiazole-3-ketone, be warming up to 90-95 DEG C, Quan Rong, slowly drops Temperature, to 20-25 DEG C, is incubated 30min, cold water washing, the snow-white granule of drying 1,2-benzisothia after filtration Azoles-3-ketone.
Compared with the existing technology, by by non-polar solven and 1,2-benzisothiazole-3-ketone mixes the present invention, It is warming up to the most molten, cools, filter, after cold water washing, the snow-white granule of drying 1,2-benzisothia Azoles-3-ketone, the method, it can be avoided that use soda acid and a large amount of water, reduces and pollutes, and good product quality, content Height, yield is high;Additionally, method of the present invention, solvent post processing is simple, significantly improves operation Condition, is worthy of popularization.
[detailed description of the invention]
The invention provides one 1, the method for purification of 2-benzisothiazole-3-ketone, comprise the following steps:
1) by non-polar solven and 1,2-benzisothiazole-3-ketone mixes, and is warming up to the most molten;
2) cool, filter 1,2-benzisothiazole-3-ketone crystal, cold water washing after, be dried Gained crystal, obtains snow-white granule 1,2-benzisothiazole-3-ketone.
Wherein, step 1) in, non-polar solven be toluene, chlorobenzene, o-dichlorohenzene, benzene, m-dichlorobenzene, O-Dimethylbenzene, meta-xylene, xylol, sym-trimethylbenzene., pseudocumene, amylalcohol, hexanol, enanthol, Capryl alcohol, propyl ether, butyl ether, dichloroethanes, chlorobutane, n-butyl bromide, dimethyl carbonate, diethyl carbonate, One or more combination in dipropyl carbonate, preferably toluene, chlorobenzene, o-Dimethylbenzene or adjacent dichloro Benzene;1,2-benzisothiazole-3-ketone and non-polar solven mass ratio are 1.5-20, preferably 3-6;1,2-benzene And isothiazole-3-ketone is 40-150 DEG C with non-polar solven solution temperature, preferably 60-120 DEG C.Step 2) In, cool to 20-25 DEG C, and be incubated 30min.Step 2) after, also comprise the steps: by Step 2) gained filtrate divides aqueous phase, and reduce pressure Distillation recovery non-polar solven, puts into 1,2-benzisothiazole -3-ketone, is warming up to 90-95 DEG C, Quan Rong, and slow cooling, to 20-25 DEG C, is incubated 30min, cold water after filtration Washing, the snow-white granule of drying 1,2-benzisothiazole-3-ketone.Visible, method of purification of the present invention, Its solvent post processing is simple, thus significantly improves operating condition.
The present invention is made further explained below below in conjunction with specific embodiment:
Embodiment 1
Put into BIT 120g, chlorobenzene 420g, be warming up to 95 DEG C, Quan Rong, slow cooling, T=20-25 DEG C, Insulation 30min.Filtering, 100g cold water washs, and dries to obtain the snow-white granule of 114.5g 1,2-benzisothiazole -3-ketone, yield 95.4%.
Filtrate divides aqueous phase, and reduce pressure Distillation recovery chlorobenzene, puts into BIT 100g, reclaims chlorobenzene 350g, heats up To 90-95 DEG C, Quan Rong, slow cooling, T=20-25 DEG C, it is incubated 30min.Filtering, 100g cold water washs, Dry to obtain the snow-white granule of 95.5g 1,2-benzisothiazole-3-ketone, yield 95.5%.
Embodiment 2
Put into 85% solid content BIT 141.2g (rolling over hundred BIT120g, water about 21.2g), chlorobenzene 420g, rise Warm to 90-95 DEG C, Quan Rong, slow cooling, T=20-25 DEG C, it is incubated 30min.Filtering, 100g cold water is washed Wash, dry to obtain the snow-white granule of 114g 1,2-benzisothiazole-3-ketone, yield 95%.
Filtrate divides aqueous phase, and reduce pressure Distillation recovery chlorobenzene, puts into 85% solid content BIT 117.6g, reclaims chlorine Benzene 350g, is warming up to 90-95 DEG C, Quan Rong, slow cooling, T=20-25 DEG C, is incubated 30min.Filter, 100g cold water washs, and dries to obtain the snow-white granule of 95g 1,2-benzisothiazole-3-ketone, yield 95%.
Embodiment 3
Put into 85% solid content BIT 141.2g (rolling over hundred BIT120g, water about 21.2g), o-dichlorohenzene 360g, It is warming up to 95 DEG C, Quan Rong, slow cooling, T=20-25 DEG C, it is incubated 30min.Filtering, 100g cold water washs, Dry to obtain the snow-white granule of 115.2g 1,2-benzisothiazole-3-ketone, yield 96%.
Filtrate divides aqueous phase, and reduce pressure Distillation recovery o-dichlorohenzene, puts into 85% solid content BIT 117.6g, returns Receive o-dichlorohenzene 300g, be warming up to 95 DEG C, Quan Rong, slow cooling, T=20-25 DEG C, it is incubated 30min.Cross Filter, 100g cold water washs, dries to obtain the snow-white granule of 95.4g 1,2-benzisothiazole-3-ketone, yield 95.4%.
The present invention is not limited by above-mentioned embodiment, other any spirit without departing from the present invention With the change made under principle, modify, substitute, combine, simplify, all should be the substitute mode of equivalence, all Within being included in protection scope of the present invention.

Claims (8)

1. one kind 1, the method for purification of 2-benzisothiazole-3-ketone, it is characterised in that comprise the following steps:
1) by non-polar solven and 1,2-benzisothiazole-3-ketone mixes, and is warming up to the most molten;
2) cool, filter 1,2-benzisothiazole-3-ketone crystal, cold water washing after, be dried Gained crystal, obtains snow-white granule 1,2-benzisothiazole-3-ketone.
The method of purification of the most as claimed in claim 11,2-benzisothiazole-3-ketone, it is characterised in that: step 1) In, described non-polar solven be toluene, chlorobenzene, o-dichlorohenzene, benzene, m-dichlorobenzene, o-Dimethylbenzene, Meta-xylene, xylol, sym-trimethylbenzene., pseudocumene, amylalcohol, hexanol, enanthol, capryl alcohol, third Ether, butyl ether, dichloroethanes, chlorobutane, n-butyl bromide, dimethyl carbonate, diethyl carbonate, carbonic acid two One or more combination in propyl ester.
The method of purification of the most as claimed in claim 21,2-benzisothiazole-3-ketone, it is characterised in that: step 1) In, 1,2-benzisothiazole-3-ketone and non-polar solven mass ratio are 1.5-20.
The method of purification of the most as claimed in claim 21,2-benzisothiazole-3-ketone, it is characterised in that: step 1) In, 1,2-benzisothiazole-3-ketone and non-polar solven mass ratio are 3-6.
5. 1 as according to any one of Claims 1-4, the method for purification of 2-benzisothiazole-3-ketone, it is special Levy and be: step 1) in, 1,2-benzisothiazole-3-ketone and non-polar solven solution temperature are 40-150 ℃。
6. 1 as according to any one of Claims 1-4, the method for purification of 2-benzisothiazole-3-ketone, it is special Levy and be: step 1) in, 1,2-benzisothiazole-3-ketone and non-polar solven solution temperature are 60-120 ℃。
The method of purification of the most as claimed in claim 61,2-benzisothiazole-3-ketone, it is characterised in that: step 2) In, cool to 20-25 DEG C, and be incubated 30min.
The method of purification of the most as claimed in claim 71,2-benzisothiazole-3-ketone, it is characterised in that: step 2) Afterwards, also comprising the steps: step 2) gained filtrate divides aqueous phase, the non-pole of Distillation recovery of reducing pressure Property solvent, put into 1,2-benzisothiazole-3-ketone, be warming up to 90-95 DEG C, Quan Rong, slow cooling is extremely 20-25 DEG C, it is incubated 30min, cold water washing, the snow-white granule of drying 1,2-benzisothiazole after filtration -3-ketone.
CN201610196128.9A 2016-03-31 2016-03-31 Method for purifying 1,2-benzisothiazole-3-ketone Pending CN105753805A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108794424A (en) * 2018-07-16 2018-11-13 连云港市三联化工有限公司 A kind of method for refining solvent of BIT
CN111559986A (en) * 2020-06-22 2020-08-21 大连百傲化学股份有限公司 Purification method of 1, 2-benzisothiazolin-3-ketone
CN116283820A (en) * 2023-03-23 2023-06-23 寿光新泰精细化工有限公司 Preparation method of 3-halogeno-1, 2-benzisothiazole

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1107837A (en) * 1993-11-24 1995-09-06 住友精化株式会社 Method for producing alkylsulfinylbenzamides and 1,2-benzisothiazol-3-ones
CN1119645A (en) * 1994-07-05 1996-04-03 住友精化株式会社 Method for producing 1,2-benzisothiazol-3-ones 21678/01
CN1422155A (en) * 2000-03-07 2003-06-04 大塚制药株式会社 Urease inhibitors
CN103204823A (en) * 2013-03-18 2013-07-17 寿光新泰精细化工有限公司 Method for purifying 1, 2-benzisothiazole-3-ketone
CN103443088A (en) * 2011-03-18 2013-12-11 住友精化株式会社 Method for producing 1,2-enzisothiazol-3-one compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1107837A (en) * 1993-11-24 1995-09-06 住友精化株式会社 Method for producing alkylsulfinylbenzamides and 1,2-benzisothiazol-3-ones
CN1119645A (en) * 1994-07-05 1996-04-03 住友精化株式会社 Method for producing 1,2-benzisothiazol-3-ones 21678/01
CN1422155A (en) * 2000-03-07 2003-06-04 大塚制药株式会社 Urease inhibitors
CN103443088A (en) * 2011-03-18 2013-12-11 住友精化株式会社 Method for producing 1,2-enzisothiazol-3-one compound
CN103204823A (en) * 2013-03-18 2013-07-17 寿光新泰精细化工有限公司 Method for purifying 1, 2-benzisothiazole-3-ketone

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108794424A (en) * 2018-07-16 2018-11-13 连云港市三联化工有限公司 A kind of method for refining solvent of BIT
CN111559986A (en) * 2020-06-22 2020-08-21 大连百傲化学股份有限公司 Purification method of 1, 2-benzisothiazolin-3-ketone
CN116283820A (en) * 2023-03-23 2023-06-23 寿光新泰精细化工有限公司 Preparation method of 3-halogeno-1, 2-benzisothiazole

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