CN112645930B - 烟嘧磺隆水相法合成工艺 - Google Patents
烟嘧磺隆水相法合成工艺 Download PDFInfo
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract
本发明涉及农药技术领域，提出了烟嘧磺隆水相法合成工艺，包括以下步骤，S1、投料：向反应釜中加入2‑乙氧羰基氨基磺酰基‑N,N‑二甲基烟酰胺，2‑氨基‑4,6‑二甲氧基嘧啶，相转移催化剂，溶剂，启动搅拌；S2、反应：温度60～100℃，反应5～7小时；S3、出料：离心，烘干干燥，得到烟嘧磺隆。通过上述技术方案，解决了现有技术中的工艺复杂，产品品质差问题。
Description
技术领域
本发明涉及农药技术领域，具体的，涉及烟嘧磺隆水相法合成工艺。
背景技术
烟嘧磺隆(商品名玉农乐)是新一代广谱、高效、低毒、低残留磺酰脲类除草剂，是迄今为止最好的玉米田除草剂品种之一。其主要通过抑制乙酰乳酸酶来防除杂草，是侧链氨基酸合成抑制剂。玉米田芽后施用，可防除一年生和多年生禾本科杂草和某些阔叶杂草，土壤中降解迅速，对下茬作物没有影响。
采用氨酯与氨基嘧啶反应制得烟嘧磺隆的现有工艺是甲苯做溶剂的条件下生产，甲苯边回流边脱水，边反应，但是由于前期反应温度高二甲氧基嘧啶易变色，生产的产品呈浅棕色，要得到品质好的产品，就得重结晶处理，该工艺反应温度高，时间长，需要溶剂回收等后处理步骤，生产安全性差，污染高。
发明内容
本发明提出烟嘧磺隆水相法合成工艺，解决了相关技术中的工艺复杂，产品品质差的问题。
本发明的技术方案如下：
烟嘧磺隆水相法合成工艺，包括以下步骤，
S1、投料：向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺，2-氨基-4,6-二甲氧基嘧啶，相转移催化剂，溶剂，启动搅拌；
S2、反应：温度60～100℃，反应5～7小时；
S3、出料：离心，烘干干燥，得到烟嘧磺隆。
作为进一步的技术方案，所述相转移催化剂为四丁基溴化铵、磷钼钒杂多酸季铵盐、链烷醇聚醚-12，质量比为1:(0.05～0.1):(0.1～0.2)；或者为四丁基溴化膦、磷钼钒杂多酸季铵盐、链烷醇聚醚-12，质量比为1:(0.05～0.1):(0.1～0.2)。
作为进一步的技术方案，所述磷钼钒杂多酸季铵盐是[(C4H9)4N]3PMo12O40、[(C4H9)4N]2HPMo12O40、[(C4H9)4N]H2PMo12O40中的一种。
作为进一步的技术方案，所述2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺与所述2-氨基-4,6-二甲氧基嘧啶的摩尔比为1:(1～1.1)。
作为进一步的技术方案，所述相转移催化剂的量为2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺质量的2％～5％。
作为进一步的技术方案，所述溶剂为乙腈质量含量为50％～60％的乙腈水溶液。
作为进一步的技术方案，所述溶剂的质量为2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺的质量的2～3倍。
本发明的工作原理及有益效果为：
1、本发明以2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺，2-氨基-4,6-二甲氧基嘧啶为原料，在相转移催化剂的作用下，使其在水相中反应，可得到收率高，质量好的烟嘧磺隆，反应条件温和，反应温度低，时间短，后处理简单，取消了重结晶等过程，直接离心就能得到烟嘧磺隆产品。
2、本发明将磷钼钒杂多酸季铵盐、链烷醇聚醚-12与四丁基溴化铵/膦复配，得到的复配催化剂具有高效的催化活性，将所需离子带入水相中迅速反应，使得反应所需条件变得温和，由于反应充分，得到的产品收率和纯度都较高。
具体实施方式
下面将结合本发明实施例，对本发明实施例中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作出创造性劳动前提下所获得的所有其他实施例，都涉及本发明保护的范围。
实施例1
向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺301.68g，2-氨基-4,6-二甲氧基嘧啶155.64g，四丁基溴化铵5.25g，0.3g[(C4H9)4N]3PMo12O40，0.6g链烷醇聚醚-12，乙腈质量含量为50％的乙腈水溶液603.93g，温度控制在60～100℃之间，反应约7小时；离心，烘干干燥，得到烟嘧磺隆398.14g，收率96.89％，纯度98.81％。
实施例2
向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺301.31g，2-氨基-4,6-二甲氧基嘧啶160.21g，四丁基溴化铵7.1g，0.7g[(C4H9)4N]2HPMo12O40，1.39g链烷醇聚醚-12，乙腈质量含量为55％的乙腈水溶液750.13g，温度控制在60～100℃之间，反应约6小时；离心，烘干干燥，得到烟嘧磺隆398.58g，收率97.12％，纯度98.96％。
实施例3
向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺301.57g，2-氨基-4,6-二甲氧基嘧啶170.65g，四丁基溴化膦11.59g，1.12g[(C4H9)4N]H2PMo12O40，2.31g链烷醇聚醚-12，乙腈质量含量为60％的乙腈水溶液900.64g，温度控制在60～100℃之间，反应约5小时；离心，烘干干燥，得到烟嘧磺隆398.64g，收率97.13％，纯度99.01％。
对比例1
向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺301.55g，2-氨基-4,6-二甲氧基嘧啶170.98g，四丁基溴化铵11.60g，3.43g链烷醇聚醚-12，乙腈质量含量为60％的乙腈水溶液900.35g，温度控制在60～100℃之间，反应约7小时；离心，烘干干燥，得到烟嘧磺隆378.67g，收率92.27％，纯度95.16％。
对比例2
向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺301.46g，2-氨基-4,6-二甲氧基嘧啶170.67g，1.13g[(C4H9)4N]H2PMo12O40，13.88g链烷醇聚醚-12，乙腈质量含量为60％的乙腈水溶液900.19g，温度控制在60～100℃之间，反应约7小时；离心，烘干干燥，得到烟嘧磺隆356.44g，收率86.85％，纯度90.62％。
对比例3
向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺301.33g，2-氨基-4,6-二甲氧基嘧啶170.64g，15.01g四丁基溴化铵，乙腈质量含量为60％的乙腈水溶液900.11g，温度控制在60～100℃之间，反应约7小时；离心，烘干干燥，得到烟嘧磺隆352.83g，收率85.97％，纯度90.13％。
从实施例和对比例中可以发现，当只使用四丁基溴化铵作为催化剂时，相同的实验条件下产量和收率较低。当只使用四丁基溴化铵，链烷醇聚醚-12或者只使用链烷醇聚醚-12，磷钼钒杂多酸季铵盐两组分作为催化剂时，相同的反应时间和温度不能使得反应完全，产量和收率较低。可见，只有当使用磷钼钒杂多酸季铵盐和链烷醇聚醚-12与四丁基溴化铵/膦复配时，催化活性最高，所得产品收率高，在97％以上，纯度在99％左右。
以上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 (5)
1.烟嘧磺隆水相法合成工艺，其特征在于，包括以下步骤，
S1、投料：向反应釜中加入2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺，2-氨基-4,6-二甲氧基嘧啶，相转移催化剂，溶剂，启动搅拌；
S2、反应：温度60～100℃，反应5～7小时；
S3、出料：离心，烘干干燥，得到烟嘧磺隆；
所述相转移催化剂为四丁基溴化铵、磷钼钒杂多酸季铵盐和链烷醇聚醚-12的混合物，所述四丁基溴化铵、磷钼钒杂多酸季铵盐和链烷醇聚醚-12的质量比为1:(0.05～0.1):(0.1～0.2)；
或者所述相转移催化剂为四丁基溴化膦、磷钼钒杂多酸季铵盐和链烷醇聚醚-12，所述四丁基溴化膦、磷钼钒杂多酸季铵盐和链烷醇聚醚-12质量比为1:(0.05～0.1):(0.1～0.2)；
所述溶剂为乙腈质量含量为50％～60％的乙腈水溶液。
2.根据权利要求1所述的烟嘧磺隆水相法合成工艺，其特征在于，所述磷钼钒杂多酸季铵盐是[(C4H9)4N]3PMo12O40、[(C4H9)4N]2HPMo12O40、[(C4H9)4N]H2PMo12O40中的一种。
3.根据权利要求1所述的烟嘧磺隆水相法合成工艺，其特征在于，所述2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺与所述2-氨基-4,6-二甲氧基嘧啶的摩尔比为1:(1～1.1)。
4.根据权利要求1所述的烟嘧磺隆水相法合成工艺，其特征在于，所述相转移催化剂的量为2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺质量的2％～5％。
5.根据权利要求1所述的烟嘧磺隆水相法合成工艺，其特征在于，所述溶剂的质量为2-乙氧羰基氨基磺酰基-N,N-二甲基烟酰胺的质量的2～3倍。
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