CN103204823B - Method for purifying 1, 2-benzisothiazole-3-ketone - Google Patents

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

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CN103204823B
CN103204823B CN201310084775.7A CN201310084775A CN103204823B CN 103204823 B CN103204823 B CN 103204823B CN 201310084775 A CN201310084775 A CN 201310084775A CN 103204823 B CN103204823 B CN 103204823B
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water
benzisothiazol
resulting
bit
solvent
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CN201310084775.7A
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CN103204823A (en
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戴明本
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寿光新泰精细化工有限公司
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Abstract

本发明属于精细化工领域,涉及一种1,2-苯并异噻唑-3-酮(BIT)的提纯方法,通过采用水溶性极性质子溶剂与水混合作溶剂重结晶,以得到雪白颗粒状的1,2-苯并异噻唑-3-酮,具体步骤为,将水溶性极性质子溶剂与水混合作溶剂,将所得溶剂与1,2-苯并异噻唑-3-酮混合,升温至全溶,脱色过滤,得滤液,将所得滤液冷却降温,过滤得1,2-苯并异噻唑-3-酮晶体,并干燥所得晶体;本发明避免了使用酸碱及大量水,极大减少了污染,所得产品不仅质量好,含量高,杂质少,而且所得产品为颗粒状,可以防止BIT粉层被人体吸入,因为BIT对人的呼吸道有严重刺激作用,极大改善了操作条件;同时颗粒状产品容易干燥,不带结晶水后,对需要无水状态的BIT的生产工艺将会有很大的好处。 The present invention belongs to the field of fine chemicals, relates to a method for the purification of 1,2-benzisothiazol-3-one (BIT), and mixed solvents cooperation recrystallized by using water-soluble polar protic solvent and water, to give a white granular 1,2-benzisothiazol-3-one, specific steps, the water-soluble polar protic solvent and water mixed solvent cooperation, the resultant mixed solvent of 1,2-benzisothiazol-3-one was heated to the whole solution, bleaching filtered to obtain the filtrate, and the resulting cooled filtrate was cooled and filtered to give 1,2-benzisothiazol-3-one crystals, and drying the resulting crystals; the present invention avoids the use of large amounts of water and acid, greatly reducing pollution, the resulting product not only of good quality, high content, fewer impurities, and the resulting product is a granular powder layer can prevent the BIT is inhaled, because there are serious BIT stimulating effect on the human respiratory tract, greatly improving the operating conditions; At the same time easy to dry granular product, without the water of crystallization, the BIT anhydrous state required for the production process will be a great advantage.

Description

一种1,2-苯并异噻唑-3-酮的提纯方法 One kind of 1,2-benzisothiazol-3-one purification method

[技术领域] [Technical Field]

[0001] 本发明属于精细化工领域,涉及化合物的提纯方法,具体地说是一种1,2-苯并异噻唑-3-酮的提纯方法。 [0001] The present invention belongs to the field of fine chemicals, relates to a method for purifying compounds, in particular a 1,2-benzisothiazol-3-one purification method.

[背景技术] [Background technique]

[0002] 1,2-苯并异噻唑-3-酮(BIT,式I )广泛应用于杀菌剂、防腐剂,其传统的提纯方法是采用酸碱法,以大量水为溶剂,先用液碱溶解,而后用盐酸析出,得到1. 2-苯并异噻唑-3-酮粉末。 [0002] 1,2-benzisothiazol-3-one (the BIT, Formula I) is widely used fungicides, preservatives, its traditional purification method is the use of acid-base method, a large amount of water as a solvent, first with liquid alkali dissolution, followed by precipitation with hydrochloric acid, to give 1. 2-benzo isothiazolin-3-one powder. 然而,该提纯方法存在以下不足之处:不仅会产生大量的含盐废水,产品质量低,而且粉尘多,操作条件差。 However, the presence of this purification method the following shortcomings: not only will produce large amounts of saline wastewater, low product quality, and dust, poor operating conditions.

[0003] [0003]

Figure CN103204823BD00031

[0004] 因此,若能提供一种避免使用酸碱及大量水,减少污染,且产品质量好,含量高,极大改善操作条件的1,2-苯并异噻唑-3-酮提纯方法,将具有非常重要的意义。 [0004] Thus, if there is provided a large amount of acid-base and avoid the use of water, reduce pollution, and good quality, high content, greatly improve the operating conditions of the 1,2-benzisothiazol-3-one purification process oxazole, It will have a very important significance.

[发明内容] [SUMMARY]

[0005] 本发明的目的就是要解决上述的不足而提供一种1,2-苯并异噻唑-3-酮的提纯方法,不仅避免了使用酸碱及大量水,极大减少了污染,而且所得产品质量好,含量高,杂质少,极大改善了条件。 [0005] The object of the present invention is to solve the above deficiencies and to provide a method of purifying 1,2-benzisothiazol-3-one, not only avoids the use of large amounts of water and acid, greatly reduce pollution, and the resulting product is good quality, high content, fewer impurities, which greatly improved the conditions.

[0006] 为实现上述目的设计一种1,2_苯并异噻唑-3-酮的提纯方法,包括以下步骤: [0006] design a method for purifying 1,2_-benzisothiazol-3-one To achieve the above object, comprising the steps of:

[0007] 1)将水溶性极性质子溶剂与水混合作溶剂,将所得溶剂与1,2_苯并异噻唑-3-酮混合,升温至全溶,脱色过滤,得滤液,所述水溶性极性质子溶剂为甲醇、乙醇中的一种或者两种的组合,其中,1,2-苯并异噻唑-3-酮与水溶性极性质子溶剂质量比为1. 5-4. 5,水与1,2-苯并异噻唑-3-酮质量比为0-2 ;显然该水溶性极性质子溶剂也可以为醋酸、丙酮、丙醇、丁醇、乙腈、甲酸中的一种或者多种的组合; [0007] 1) a water-soluble polar protic solvent and water mixed solvent cooperation, 1,2_ mixed with the resulting solvent-benzisothiazol-3-one, the whole solution was warmed to decolorization filtered to obtain the filtrate, the aqueous polar protic solvent is methanol, ethanol, one kind or a combination of the two, wherein the 1,2-benzisothiazol-3-one and water-soluble polar protic solvent mass ratio of 1. 5-4. 5 of water to a ketone by mass of 1,2-benzisothiazol-3 ratio is 0-2; apparently the water-soluble polar protic solvents may be used as acetate, acetone, propanol, butanol An acetonitrile, formic acid or more thereof;

[0008] 2)将所得滤液冷却降温,过滤得1,2_苯并异噻唑-3-酮晶体,并干燥所得晶体。 [0008] 2) cooling the resulting filtrate was cooled and filtered to give 1,2_-benzisothiazol-3-one crystals, and drying the resulting crystals.

[0009] 在本发明的一些优选实施方案中,步骤1)中1,2-苯并异噻唑-3-酮与溶剂溶解温度为40_120°C。 [0009] In some preferred embodiments of the present invention, in step 1) 1,2-benzisothiazol-3-one and the dissolution temperature of the solvent 40_120 ° C.

[0010] 在本发明的一些优选实施方案中,步骤2)中冷却温度为0_35°C。 [0010] In some preferred embodiments of the invention, step 2) cooling temperature 0_35 ° C.

[0011] 在本发明的一些优选实施方案中,步骤2)中冷却降温时间为I. 5_8h。 [0011] In some preferred embodiments of the invention, step 2) in the cool-down time I. 5_8h.

[0012] 在本发明的一些实施方案中,步骤2)中冷却降温时,对滤液进行搅拌,搅拌速度为25-55RPM。 [0012] In some embodiments of the present invention, step 2) cooling down the filtrate was stirred, the stirring speed was 25-55RPM.

[0013] 本发明同现有技术相比,具有如下有益效果:由于采用水溶性极性质子溶剂与水混合作溶剂重结晶,得到了雪白颗粒状1,2-苯并异噻唑-3-酮,避免了使用酸碱及大量水, 极大减少了污染;而且,一方面,所得产品质量好,含量高,杂质少,可以满足一些特殊用途; 另一方面,所得产品为颗粒状,可以防止BIT粉层被人体吸入,因为BIT对人的呼吸道有严重的刺激作用,从而极大地改善了操作条件;此外,颗粒状产品容易干燥,不带结晶水后,对需要无水状态的BIT的生产工艺将会有很大的好处。 [0013] Compared with the prior art the present invention has the following advantages: Since a water-soluble polar protic solvent and water mixed solvent cooperation recrystallized a white particulate 1,2-benzisothiazol-3-one , avoiding the use of acid-base and plenty of water, greatly reducing pollution; and, on the one hand, the resulting product is good quality, high content, fewer impurities, to meet some special purpose; on the other hand, the resulting product is granular, can be prevented are inhaled powder layer BIT, BIT severe because stimulation of the human respiratory tract, thereby greatly improving the operating conditions; in addition, the granular product is easily dried, without crystallization water, the need for the production of anhydrous state BIT technology will be a great benefit.

[附图说明] [BRIEF DESCRIPTION]

[0014] 图1是1,2-苯并异噻唑-3-酮标准品的HPLC检测数据; [0014] FIG. 1 is a 1,2-benzisothiazol-3-one HPLC detection data of the standard;

[0015] 图2是实施例1所得产物的HPLC检测数据。 [0015] FIG 2 is a HPLC detection data of the product of Example 1 obtained.

[具体实施方式] [Detailed ways]

[0016] 下面结合实施例对本发明作以下进一步说明: [0016] The following embodiments in conjunction with embodiments of the present invention will be further explained below:

[0017] 实验例1 [0017] Experimental Example 1

[0018] 投1,2-苯并异噻挫-3-酮160g,甲醇450g,水130g,升温至65°C全溶,加入I. 5g 活性炭,保温30min,过滤,所得滤液,调慢搅拌,缓慢降温至20°C,约需要lh,过滤,100g冷水洗涤,晾干得145g雪白颗粒1,2_苯并异噻唑-3-酮(HPLC>99. 85% ),收率90. 6%。 [0018] The administration of 1,2-benzisothiazol-3-one setback 160g, 450 g of methanol, water, 130g, was heated to 65 ° C the whole solution, I. 5g of activated carbon was added, incubated 30min, filtered, the resultant filtrate, stirred slow the , slowly cooled to 20 ° C, it takes about LH, filtered, washed with 100g of cold water, air dried to give 145g white particles 1,2_-benzisothiazol-3-one (HPLC> 99. 85%), yield 90.6 %.

[0019] 实验例2 [0019] Experimental Example 2

[0020] 投90%固含量1,2_苯并异噻唑-3-酮178g,甲醇450g,水110g,升温至66°C全溶,加入I. 5g活性炭,保温30min,过滤,所得滤液,调慢搅拌,缓慢降温至20°C,约需要lh, 过滤,100g冷水洗绦,晾干得143g雪白颗粒1,2-苯并异噻唑-3-酮(HPLC>99. 85 % ),收率89. 3%〇 [0020] 90% solids content cast 1,2_-benzisothiazol-3-one 178 g, 450 g of methanol, 110g of water, warmed to 66 ° C the whole solution, I. 5g of activated carbon was added, incubated 30min, filtered, the resulting filtrate, slow the stirring, slowly cooled to 20 ° C, it takes about LH, filtered, washed with cold water 100g sash, air dried to give 143g white particles 1,2-benzisothiazol-3-one (HPLC> 99. 85%), close rate of 89.3% billion

[0021] 实验例3 [0021] Experimental Example 3

[0022] 投1,2_苯并异噻唑-3-酮160g,乙醇420g,水135g,升温至70°C全溶,加入I. 5g 活性炭,保温30min,过滤,所得滤液,调慢搅拌,缓慢降温至20°C,约需要lh,过滤,100g冷水洗涤,晾干得140g雪白颗粒1,2_苯并异噻唑-3-酮(HPLC>99. 85% ),收率87. 5%。 [0022] administered 1,2_-benzisothiazol-3-one 160g, 420 g of ethanol, water, 135g, was heated to 70 ° C the whole solution, I. 5g of activated carbon was added, incubated 30min, filtered, the resulting filtrate, slow the stirring, slowly cooled to 20 ° C, it takes about LH, filtered, washed with 100g of cold water, air dried to give 140g white particles 1,2_-benzisothiazol-3-one (HPLC> 99. 85%), 87. 5% yield .

[0023] 应当理解的是,本发明并不受上述实施方式的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。 [0023] It should be appreciated that the present invention is not limited to the above embodiments, changes made to any other without departing from the spirit and principle of the present invention, modifications, substitutions, combinations, simplification of equivalent effect replacement pattern, are included within the scope of the present invention.

Claims (5)

1. 一种1,2-苯并异噻唑-3-酮的提纯方法,其特征在于,包括以下步骤: 1) 将水溶性极性质子溶剂与水混合作溶剂,将所得溶剂与1,2-苯并异噻唑-3-酮混合,升温至全溶,脱色过滤,得滤液,所述水溶性极性质子溶剂为甲醇、乙醇中的一种或者两种的组合,其中,1,2-苯并异噻唑-3-酮与水溶性极性质子溶剂质量比为1. 5-4. 5,水与1,2-苯并异噻唑-3-酮质量比为0. 5-1. 5 ; 2) 将所得滤液冷却降温,过滤得1,2-苯并异噻唑-3-酮晶体,并干燥所得晶体。 CLAIMS 1. A method for purifying 1,2-benzisothiazol-3-one, characterized by comprising the steps of: 1) a water-soluble polar protic solvent and water mixed solvent cooperation, and the resulting solvent 1,2 - benzo -3- isothiazolone mixture, the whole solution was warmed to decolorization filtered to obtain the filtrate, the water-soluble polar protic solvent is methanol, ethanol, one kind or a combination of the two, wherein the 1,2 benzisothiazol-3-one and water-soluble polar protic solvent mass ratio of 1. 5-4. 5, water and 1,2-benzisothiazol-3-one mass ratio of 0. 5-1. 5 ; 2) cooling the resulting filtrate was cooled and filtered to give 1,2-benzisothiazol-3-one crystals, and drying the resulting crystals.
2. 如权利要求1所述的方法,其特征在于:步骤1)中1,2-苯并异噻唑-3-酮与溶剂溶解温度为40-120°C。 2. The method according to claim 1, wherein: step 1) 1,2-benzisothiazol-3-one dissolved in a solvent temperature of 40-120 ° C.
3. 如权利要求1或2所述的方法,其特征在于:步骤2)中冷却温度为0-35 °C。 The method of claim 1 or claim 2, wherein: in step 2) the cooling temperature is 0-35 ° C.
4. 如权利要求3所述的方法,其特征在于:步骤2)中冷却降温时间为I. 5-8h。 4. The method according to claim 3, characterized in that: in step 2) cooling down time I. 5-8h.
5. 如权利要求4所述的方法,其特征在于:步骤2)中冷却降温时,对滤液进行搅拌,搅拌速度为25-55RPM。 5. The method according to claim 4, wherein: step 2) cooling down the filtrate was stirred, the stirring speed was 25-55RPM.
CN201310084775.7A 2013-03-18 2013-03-18 Method for purifying 1, 2-benzisothiazole-3-ketone CN103204823B (en)

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CN105753805A (en) * 2016-03-31 2016-07-13 寿光新泰精细化工有限公司 Method for purifying 1,2-benzisothiazole-3-ketone
CN105801516B (en) * 2016-04-28 2018-05-04 大丰跃龙化学有限公司 One kind of 1,2-isothiazolin-3-one Purification Process

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US4590196A (en) * 1984-08-23 1986-05-20 Bristol-Myers Company Analgesic 1,2-benzisothiazol-3-ylpiperazine derivatives
CA2151074C (en) * 1994-07-05 2005-08-02 Hirokazu Kagano Method for producing 1,2-benzisothiazol-3-ones
JP3777800B2 (en) * 1998-06-24 2006-05-24 新日本理化株式会社 Method for producing a 1,2-benzisothiazol-3-one compounds
US7585980B2 (en) * 2006-05-25 2009-09-08 Troy Corporation Immobilized 1,2-benzisothiazolin-3-one
JP2012214405A (en) * 2011-03-31 2012-11-08 Sumitomo Seika Chem Co Ltd N,n'-methylenebis(1,2-benzisothiazolin-3-one) compound and method for producing the same
CN102491955A (en) * 2011-12-08 2012-06-13 上海易摩生物科技有限公司 Process method for synthesizing 1, 2-benzisothiazdin-3-ketone

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