CN113200937B - 一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法 - Google Patents

一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法 Download PDF

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CN113200937B
CN113200937B CN202110526254.7A CN202110526254A CN113200937B CN 113200937 B CN113200937 B CN 113200937B CN 202110526254 A CN202110526254 A CN 202110526254A CN 113200937 B CN113200937 B CN 113200937B
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杨贯羽
何攀
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Abstract

本发明提供了一种催化氧化制备1,2‑苯并异噻唑啉‑3‑酮的方法，以金属锰盐或者锰配合物为催化剂，在氧气或空气环境中，使胺类化合物发生氧化环合反应生成1,2‑苯并异噻唑啉‑3‑酮。本发明反应在使用氧气或空气作氧化剂；催化剂简单便宜，催化活性高，反应效率高；制备工艺简捷，产物选择性高，副产物少；废物少，环境友好，具有较强的工业应用前景。

Description

一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法
技术领域
本发明涉及苯并[d]异噻唑啉-3(2H)-酮的制备领域，具体涉及一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法。
背景技术
1,2-苯并异噻唑啉-3-酮(简称BIT)，是一种重要、常用的杀菌剂和防腐剂。具有杀菌能力强、应用剂量小、相容性好、耐温性和耐酸碱能力强、对环境安全等优良性能。广泛用于日化产品、高分子制品、粘合剂、纺织、涂料、造纸、建材、制革、轻工、油品、油墨、工业循环冷却水、农林环保等领域。
1,2-苯并异噻唑啉-3-酮的合成方法有很多，而经2-巯基苯甲酰胺或者2,2’-二硫代二苯甲酰胺的环合反应为主流工业生产方法(图式1)。
Figure GDA0003886310340000011
文献报道的环合剂有：(1)氯气[中国发明专利申请号：111253335；110467584；110483438；103172588；103130738；102002015；102491955；104529932]；(2)Br2[S.Chen etal.PCT Int.Appl.,2019174279]；(3)SOCl2或者SO2Cl2[中国发明专利申请号：108239038；J.Su et al.Bioorganic Chemistry,2019,84,192-201；应用化工,2014,43(9),1637-1639；M.Pietka-Ottlik et al Molecules,2010,15,8214-8228；]；(4)H2O2[Jin etal.Synlett,2003,(13),1967；C.Berg et al.U.S.Pat.Appl.0130109864；R.Baum.PCTInt.Appl.,2015055293；张可青等.应用化工,2014,43,09]。(5)分子氧：T.Li等报道了一种在DMSO溶液中催化分子氧氧化环合制备1,2-苯并异噻唑啉-3-酮的方法，使用的催化剂为CuBr，配体(S)-Proline[T.Li et al.Organic&Biomolecular Chemistry,2016,14(26),6297]。本发明人曾报道了水相中催化分子氧氧化环合制备1,2-苯并异噻唑啉-3-酮的方法，使用的催化剂为水溶性过渡金属酞菁化合物[中国专利公开号CN111072587A]。
上述专利采用的氯气、液溴、SOCl2、SO2Cl2等化学品强腐蚀性，安全隐患大，使用伴生大量含盐废水，不利于其应用。
发明内容
本发明提出了一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法，该方法以锰盐催化剂，以简单的胺类化合物为配体，使用分子氧(氧气或空气)作为氧化剂。锰元素在自然界储量多，锰盐价格低廉。所用胺类化合物便宜易得。因此，本发明具有绿色、成本低、催化效率高、产品选择性高、不使用其它添加剂、后处理简单等优点，具有优异的应用前景。
实现本发明的技术方案是：
一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法，以金属锰盐或者锰配合物为催化剂，在氧气或空气环境中，使胺类化合物发生氧化环合反应生成1,2-苯并异噻唑啉-3-酮(以下简称BIT)。
所述金属锰盐为Mn2SO4、MnS2O6、Mn2CO3、Mn(NO3)2、MnCl2、MnBr2、MnI2、Mn(OAc)2、Mn(OAc)3、Mn(OH)2、Mn(OH)3、KMnO4、Mn3(PO4)2或者其水合物的任意一种。
所述锰配合物为金属锰盐与配体形成的锰配合物。
所述配体为乙二胺、2-二甲氨基乙胺、四甲基乙二胺、二乙胺、三乙胺、吡啶、2,2’-联吡啶、2-氨甲基吡啶、2-[(二甲氨基)甲基]吡啶、乙醇胺、二乙醇胺或三乙醇胺的任意一种。
所述胺类化合物为2-巯基苯甲酰胺或者2,2’-二硫代二苯甲酰胺，也可为二者的混合物，其比例没有特殊要求。
所述氧化环合反应的溶剂为水、甲醇、乙醇或DMF的任意一种或一种以上混合。
所述锰配合物可分别将金属锰盐与配体投入到反应中使用，或者将金属锰盐与配体制备成锰配合物再投入到反应中使用。
所述金属锰盐或者锰配合物的用量为胺类化合物的0.01-5mol％。
所述氧化环合反应的反应压力0.1-1.00MPa、温度40-120℃、反应时间为1-40h。
本发明中，用于催化剂的锰盐、配体和锰配合物可以直接购买相应的化工产品，也可以合成后使用。
本发明在使用过程中，反应效果随催化剂用量增加而提高，但催化剂用量增加生产成本也随之增加，过量的催化剂会带来分离困难。
本发明的方法在溶液中进行，溶剂的用量增加会溶解更多的催化剂而提高反应速度，会降低反应液粘稠度而提高搅拌效果，进而提高反应效果，但溶剂的用量过大会降低反应效率，增加能源消耗。
本发明中制备反应结束后，后处理工艺过程没有特别限定，产物分离提纯可以通过以下方法进行：氧化环合反应结束后，直接蒸馏除去溶剂，水洗除去催化剂，再经重结晶、烘干，得到产物。
本发明的有益效果是：本发明反应在使用氧气或空气作氧化剂；催化剂简单便宜，催化活性高，反应效率高；制备工艺简捷，产物选择性高，副产物少；废物少，环境友好，具有较强的工业应用前景。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1为本发明实施例1制备的BIT的1HNMR谱图。
图2是实施例1制备的BIT的13C NMR谱图。
具体实施方式
下面将结合本发明实施例，对本发明的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1
在250mL的反应釜中，投入15.28g 2-巯基苯甲酰胺与2,2’-二硫代二苯甲酰胺的混合物(摩尔比3:1)、0.42g Mn(OH)3、0.60g三乙醇胺和160mL乙醇；搅拌下加热升温至120℃，通入氧气，保持反应釜内压强为0.2MPa，反应10小时后停止反应，旋蒸除去乙醇，加100mL水搅拌20min，过滤，滤饼烘干得白色固体BIT 12.23g，收率为90％，熔点154-156℃，液相色谱分析产物纯度为98％。
实施例2
在250mL的反应釜中，投入30.6g 2-巯基苯甲酰胺、0.11g碳酸锰一水合物、0.28g2-二甲氨基乙胺、100mL水和50mL甲醇；搅拌下加热升温至40℃，压入空气，保持反应釜内压强为1.0MPa，反应40小时后停止反应，旋蒸除去甲醇，冷却，过滤，水洗涤，烘干得产品29.6gBIT，收率为98％，液相色谱仪分析产物纯度为99％。
实施例3
在250mL的反应釜中，投入45.95g 2,2’-二硫代二苯甲酰胺、0.02g 2,2’-联吡啶锰(Ⅱ)配合物和130mL DMF；搅拌下加热升温至80℃，通入氧气，保持反应釜内压强为0.4MPa，反应7小时后停止反应，减压蒸馏除去大部分DMF，加100mL水搅拌40min，过滤，滤饼烘干得白色固体BIT 44.85g，收率为99％，熔点154-156℃，液相色谱分析产物纯度为98％。
实施例4
在250mL的反应釜中，投入18.26g 2,2’-二硫代二苯甲酰胺、0.2402g磷酸锰三水合物、50mL水和100mL乙醇；搅拌下加热升温至95℃，通入空气，保持反应釜内压强为0.3MPa，反应5小时后停止反应，旋蒸除去乙醇，加50mL水搅拌40min，过滤，滤饼烘干得白色固体BIT 14.49g，收率为80％，熔点154-156℃，液相色谱分析产物纯度为97％。
按实施例1相同的方法制备BIT，其各种反应条件和反应结果见下表。
Figure GDA0003886310340000041
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (6)

1.一种催化氧化制备1,2-苯并异噻唑啉-3-酮的方法，其特征在于：以锰配合物为催化剂，在氧气或空气环境中，使胺类化合物发生氧化环合反应生成1,2-苯并异噻唑啉-3-酮；
所述锰配合物为金属锰盐与配体形成的锰配合物；
所述金属锰盐为Mn2SO4、MnS2O6、Mn2CO3、Mn(NO3)2、MnCl2、MnBr2、MnI2、Mn(OAc)2、Mn(OAc)3、Mn(OH)2、Mn(OH)3、KMnO4、Mn3(PO4)2或者其水合物的任意一种；
所述配体为乙二胺、2-二甲氨基乙胺、四甲基乙二胺、二乙胺、三乙胺、吡啶、2,2’-联吡啶、2-氨甲基吡啶、2-[(二甲氨基)甲基]吡啶、乙醇胺、二乙醇胺或三乙醇胺的任意一种；
所述胺类化合物为2-巯基苯甲酰胺或者2,2’-二硫代二苯甲酰胺。
2.根据权利要求1所述的方法，其特征在于：所述氧化环合反应的溶剂为水、甲醇、乙醇或DMF的任意一种或一种以上混合。
3.根据权利要求1所述的方法，其特征在于：所述锰配合物可分别将金属锰盐与配体投入到反应中使用，或者将金属锰盐与配体制备成锰配合物再投入到反应中使用。
4.根据权利要求1所述的方法，其特征在于：所述金属锰盐或者锰配合物的用量为胺类化合物的0.01-5 mol%。
5.根据权利要求1所述的方法，其特征在于：所述氧化环合反应的反应压力0.1-1.00MPa、温度40-120℃、反应时间为1-40h。
6.根据权利要求1-5任一项所述的方法，其特征在于：氧化环合反应结束后，直接蒸馏除去溶剂，水洗除去催化剂，再经重结晶、烘干，得到产物。
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