CN105753805A - Method for purifying 1,2-benzisothiazole-3-ketone - Google Patents
Method for purifying 1,2-benzisothiazole-3-ketone Download PDFInfo
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- 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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- ketone
- benzisothiazole
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- 238000000034 method Methods 0.000 title claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 claims description 19
- 238000000746 purification Methods 0.000 claims description 18
- 239000008187 granular material Substances 0.000 claims description 13
- 238000010792 warming Methods 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 238000010583 slow cooling Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 6
- -1 o-dichlorohenzene Chemical compound 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 5
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000012454 non-polar solvent Substances 0.000 abstract 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 2
- 238000003889 chemical engineering Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229940078552 o-xylene Drugs 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 5
- 238000012805 post-processing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical group ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- GNHQSAUHXKRQMC-UHFFFAOYSA-N benzene;chlorine Chemical compound [Cl].C1=CC=CC=C1 GNHQSAUHXKRQMC-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
Landscapes
- 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
[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.
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Cited By (3)
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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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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