CN100509737C - 2,6-二氯苯酚化合物的生产方法 - Google Patents
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- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
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Abstract
一种高产率地生产式(1)表示的2,6-二氯苯酚化合物的方法:其中,R表示3,3-二卤代-2-丙烯基或任选地被卤素原子取代的苯甲基,该方法是在仲胺存在下使式(2)表示的苯酚化合物与磺酰氯反应:其中,R的定义同上。得到的式(1)表示的2,6-二氯苯酚化合物是制备具有杀虫/杀螨活性的二卤代丙烯化合物的有用中间体。
Description
发明领域
本发明涉及2,6-二氯苯酚化合物的生产方法。
背景技术
美国专利5872137和5922880中描述了一种2,6-二氯苯酚化合物,该化合物是制备具有杀虫/杀螨活性的二卤代丙烯化合物的有用中间体。根据这两篇专利的描述,所述2,6-二氯苯酚化合物可以通过苯酚化合物与叔丁基次氯酸盐反应而制备(参见美国专利5872137,第4栏的80和126:美国专利5922880,第83-84栏的90和106)。
但是,这样的制备方法产率不高,因此不足以制备目的物2,6-二氯苯酚化合物。
另一方面,JP昭55-40613A和JP昭52-27734A中描述了用氯气对4-烷基酚的2,6-二氯化。甲氧基苯酚的氯化还描述在Chemosphere,第17卷,1821-1829页(1988)和Ann.Rept.Takeda Res.Lab.,第26卷,138-148页(1967)中。
本发明的目的是提供一种制备具有杀虫/杀螨活性的二卤代丙烯化合物的有用中间体2,6-二氯苯酚化合物的生产方法。
发明概述
本发明提供一种式(1)表示的2,6-二氯苯酚化合物的生产方法:
其中,R表示3,3-二卤代-2-丙烯基或任选地被卤素原子取代的苯甲基,该方法包括在仲胺存在下使式(2)表示的苯酚化合物与磺酰氯反应:
其中,R的定义同上,该方法的产品产率很高。
发明详述
在本发明中,用R表示的3,3-二卤代-2-丙烯基的例子是3,3-二氯-2-丙烯基和3,3-二溴-2-丙烯基。另外,任选地被卤素原子取代的苯甲基的例子是其苯环上的氢原子可以被至少一个卤素原子取代的苯甲基,其典型的例子是苯甲基和4-氯苯甲基。
本发明方法的特征在于在仲胺存在下使式(2)表示的苯酚化合物与磺酰氯反应。
该反应通常在溶剂中进行。该反应使用的溶剂的例子包括芳香烃如苯、甲苯、二甲苯、1,3,5-三甲基苯、乙苯等;脂肪烃如己烷、庚烷、辛烷等;卤代芳香烃如氯苯、二氯苯、三氟甲苯等;及其混合物。
该反应使用的仲胺的例子包括二烷基胺如二(C2-C6)烷基胺;二烯基胺如二(C3-C6)烯基胺;烷基烯基胺如(C2-C6)烷基(C3-C6)烯基胺;和二环烷基胺如二(C3-C6)环烷基胺。典型的二烷基胺是二乙基胺、二丙基胺、二丁基胺、二戊基胺、二己基胺、二异丙基胺、二仲丁基胺、乙基丙基胺等。典型的二烯基胺是二烯丙基胺、二(3-丁烯基)胺等。典型的烷基烯基胺是烯丙基丙基胺等。典型的二环烷基胺是二环丙基胺、二环丁基胺、二环戊基胺、二环己基胺等。
该反应中仲胺的用量通常,基于1摩尔式(2)表示的苯酚化合物,为0.001-1摩尔,为了在反应后更好地进行处理,优选为0.001-0.1摩尔。
该反应中磺酰氯的用量通常,基于1摩尔式(2)表示的苯酚化合物,为1.5-3.0摩尔,为了提高产率,优选为2.0-2.5摩尔。
反应温度通常为0-100℃,反应时间通常为1-24小时。
例如,可以用下述方法进行反应:1)将式(2)表示的苯酚化合物、仲胺和磺酰氯溶解在溶剂中并进行搅拌的方法。2)将式(2)表示的苯酚化合物和仲胺溶解在溶剂中,并在搅拌的同时将磺酰氯滴加到溶液中的方法。3)将仲胺溶解在溶剂中,并在搅拌的同时将式(2)表示的苯酚化合物和磺酰氯滴加到溶液中的方法。
用诸如高性能液相色谱、气相色谱、薄层色谱等分析手段分析反应混合物,可以确认反应状态。
反应后,例如用下述方法能够将式(1)表示的2,6-二氯苯酚化合物分离出来:
1)将反应混合物倾入酸性水(如:盐酸、含水硫酸),将有机溶剂与水分离,并浓缩得到的有机层。
2)将反应混合物倾入弱碱性水(如:碳酸氢钠水溶液),将有机溶剂与水分离,并浓缩得到的有机层。
3)将还原剂(如:亚硫酸钠、亚硫酸氢钠、硫代硫酸钠)的水溶液加入反应混合物,在0-100℃下搅拌0.1-24小时,将有机溶剂与水分离,浓缩得到的有机层。
可以用柱色谱法、再结晶法等进一步纯化分离出的式(1)表示的2,6-二氯苯酚化合物。
实施例
下面用实施例说明本发明,但本发明并不限于这些实施例。
实施例1
将5.05g式(3)表示的4-(3,3-二氯-2-丙烯基氧)苯酚(纯度:99%)和0.08g二环己基胺溶解在23.7g甲苯中,
在搅拌的同时在65-70℃下在5小时内滴加6.41g磺酰氯。加入磺酰氯后,将混合物在65-70℃下搅拌3小时。然后在反应混合物中加入20克10%的亚硫酸钠水溶液并在65-70℃下再搅拌1小时。将反应混合物冷却到室温后分离出有机层,依次用5%的盐酸、饱和盐水和水洗涤有机层,在无水硫酸钠上干燥并减压浓缩,得到6.6g式(4)表示的2,6-二氯-4-(3,3-二氯-2-丙烯基氧)苯酚的粗产品:
用液相色谱分析该粗产品,分析结果显示其含量为96%(产率:96%)。2,6-二氯-4-(3,3-二氯-2-丙烯基氧)苯酚
1H-NMR(CDCl3/TMS)δ(ppm):
4.57(2H,d),5.50(1H,brs),6.11(1H,t),6.85(2H,s)
实施例2
将4.38克4-(3,3-二氯-2-丙烯基氧)苯酚(纯度:100%)和0.03g二乙基胺溶解在26.3g甲苯中,在搅拌的同时在65-70℃下在3小时内向其中滴加5.61g磺酰氯。加入磺酰氯后,将混合物在65-70℃下搅拌1小时。将反应混合物冷却到室温后在反应混合物中加入20克碳酸氢钠的饱和水溶液。分离出有机层,依次用10克5%的盐酸和10g水洗涤有机层,然后减压浓缩,得到5.76克2,6-二氯-4-(3,3-二氯-2-丙烯基氧)苯酚的粗产品。用液相色谱分析该粗产品,分析结果显示其含量为95%(产率:95%)。
实施例3
将4.38克4-(3,3-二氯-2-丙烯基氧)苯酚(纯度:100%)和0.04g二异丙基胺溶解在26.3g甲苯中,在搅拌的同时在65-70℃下在3小时内向其中滴加5.61g磺酰氯。加入磺酰氯后,将混合物在65-70℃下搅拌1小时。将反应混合物冷却到室温后在反应混合物中加入20克碳酸氢钠的饱和水溶液。分离出有机层,依次用10克5%的盐酸和10g水洗涤有机层,然后减压浓缩,得到5.76克2,6-二氯-4-(3,3-二氯-2-丙烯基氧)苯酚的粗产品,用液相色谱分析该粗产品,分析结果显示其含量为96%(产率:96%)。
实施例4
将10克4-苯甲基氧苯酚(纯度:100%)和0.18g二环己基胺溶解在43.25g甲苯中,在搅拌的同时在65-70℃下在8小时内滴加13.48g磺酰氯。加入磺酰氯后,将混合物在65-70℃下搅拌1小时。然后在反应混合物中加入50克10%的亚硫酸钠水溶液并在65-70℃下再搅拌1小时。依次用5%的盐酸、饱和盐水和水洗涤有机层,在无水硫酸钠上干燥并减压浓缩,得到13.1g式(5)表示的2,6-二氯-4-苯甲基氧苯酚的粗产品:
用液相色谱分析该粗产品,分析结果显示其含量为96%(产率:94%)。2,6-二氯-4-苯甲基氧苯酚
1H-NMR(CDCl3/TMS)δ(ppm):
4.98(2H,s),5.47(1H,s),6.92(2H,s),7.39(5H,s)
在上述实施例中,粗产品的含量是用下述以邻苯二甲酸二苯酯作为内标的分析条件测定的。
仪器:Shimadzu GC-14A气相色谱仪
柱:J & W Scientific DB-1(0.53mmφ×30m,膜厚:1.5μm)
流动相:氦气5ml/min
检测器:FID
注射温度:300℃
检测器温度:300℃
柱温:80℃(5分钟)→10℃/min→300℃(20分钟)
用本发明的生产方法可以高产率地生产式(1)表示的2,6-二氯苯酚化合物,该化合物是制备具有杀虫/杀螨活性的二卤代丙烯化合物的有用中间体。
Claims (8)
2、根据权利要求1的生产方法,其中,R表示3,3-二卤代-2-丙烯基。
3、根据权利要求2的生产方法,其中,R表示3,3-二氯-2-丙烯基。
4、根据权利要求1的生产方法,其中,R表示苯甲基。
5、根据权利要求1的生产方法,其中,所述二烷基胺或二环烷基胺是二乙基胺、二丙基胺、二丁基胺、二戊基胺、二己基胺、二异丙基胺、二仲丁基胺、乙基丙基胺、二环丙基胺、二环丁基胺、二环戊基胺或二环己基胺。
6、根据权利要求1的生产方法,其中,反应温度是0-100℃。
7、根据权利要求1的生产方法,其中,用于反应的二烷基胺或二环烷基胺与式(2)表示的苯酚化合物的用量摩尔比是0.001:1到1:1。
8、根据权利要求1的生产方法,其中,用于反应的磺酰氯与式(2)表示的苯酚化合物的用量摩尔比是1.5:1到3.0:1。
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JP2001387259A JP4045795B2 (ja) | 2001-12-20 | 2001-12-20 | 2,6−ジクロロフェノール化合物の製造法 |
JP2001387259 | 2001-12-20 |
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CN1426989A CN1426989A (zh) | 2003-07-02 |
CN100509737C true CN100509737C (zh) | 2009-07-08 |
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US (1) | US6635787B2 (zh) |
EP (1) | EP1321449B1 (zh) |
JP (1) | JP4045795B2 (zh) |
CN (1) | CN100509737C (zh) |
AT (1) | ATE366719T1 (zh) |
BR (1) | BR0205408B1 (zh) |
DE (1) | DE60221090T2 (zh) |
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CN105272829A (zh) * | 2014-11-14 | 2016-01-27 | 连云港致诚化工有限公司 | 一种2,6-二氯苯酚的合成方法 |
CN107285344B (zh) * | 2017-07-26 | 2023-07-21 | 沈阳化工研究院有限公司 | 一种苯酚生产过程中副产物混合废盐的处理工艺和装置 |
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JPS5227734A (en) | 1975-08-27 | 1977-03-02 | Sumitomo Chem Co Ltd | Process for preparation of 2,6-dichloro- 4-methylphenol |
JPS5540613A (en) | 1978-09-14 | 1980-03-22 | Sumitomo Chem Co Ltd | Preparation of 2, 6-dichloro-4-alkylphenol |
JPH0625063A (ja) | 1992-03-25 | 1994-02-01 | Fuji Kagaku Kogyo Kk | フェノキシベンゼン誘導体及びその製造法 |
IL111252A0 (en) * | 1993-10-19 | 1994-12-29 | Sumitomo Chemical Co | Dihalopropene compound, insecticide/acaricide containing said dihalopropene compound as active ingredient,and intermediate compound for use in production of said dihalopropene compound |
DK0722430T3 (da) * | 1994-08-04 | 1999-06-28 | Sumitomo Chemical Co | Dihalogenpropenforbindelser, insekticide/acaricide midler indeholdende samme og mellemprodukter til fremstilling deraf |
TW307746B (zh) * | 1994-10-14 | 1997-06-11 | Sumitomo Chemical Co | |
US5952386A (en) * | 1995-04-18 | 1999-09-14 | Sumitomo Chemical Company, Limited | Dihalopropene compounds, insecticides containing them as active ingredients, and intermediates for their production |
US6140274A (en) * | 1996-01-30 | 2000-10-31 | Sumitomo Chemical Company, Limited | Dihalopropene compounds, their use as insecticides/acaricides and intermediates for their production |
DE69827939T2 (de) * | 1997-04-08 | 2005-12-08 | Sumitomo Chemical Co. Ltd. | Oxim-verbindungen, ihre anwendung und zwischenprodukte zu ihrer herstellung |
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EP1321449A1 (en) | 2003-06-25 |
BR0205408B1 (pt) | 2012-05-15 |
HUP0204401A3 (en) | 2004-01-28 |
EP1321449B1 (en) | 2007-07-11 |
JP4045795B2 (ja) | 2008-02-13 |
HU0204401D0 (en) | 2003-02-28 |
BR0205408A (pt) | 2004-07-20 |
IL153128A0 (en) | 2003-06-24 |
DE60221090D1 (de) | 2007-08-23 |
JP2003183207A (ja) | 2003-07-03 |
CN1426989A (zh) | 2003-07-02 |
ATE366719T1 (de) | 2007-08-15 |
IL153128A (en) | 2008-11-26 |
HUP0204401A2 (hu) | 2003-08-28 |
HU224406B1 (hu) | 2005-08-29 |
US20030120119A1 (en) | 2003-06-26 |
DE60221090T2 (de) | 2008-03-20 |
US6635787B2 (en) | 2003-10-21 |
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