CN102372739A - 一种草铵膦的合成方法 - Google Patents
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- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 title abstract 5
- 239000005561 Glufosinate Substances 0.000 title abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 16
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- 239000001099 ammonium carbonate Substances 0.000 abstract 2
- WPEAFCGWTBGVNU-UHFFFAOYSA-N methyl(propoxy)phosphinic acid Chemical compound CCCOP(C)(O)=O WPEAFCGWTBGVNU-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 238000007059 Strecker synthesis reaction Methods 0.000 abstract 1
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- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 17
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Abstract
本发明涉及一种农药草铵膦((D，L)一2-氨基-4－（羟基(甲基)氧膦基）丁酸)及其与酸或碱的盐的合成方法，是一种通过施特雷克（strecker）反应制备农药草铵膦的合成方法，将中间体化合物（3－腈基－3－羟基）丙基甲基膦酸与二氧化碳和氨气在水溶液中直接反应合成农药草铵膦及其与酸或碱的盐的方法。将中间体化合物（3－腈基－3－羟基）丙基甲基膦酸加入到高压釜中，然后加入二氧化碳和氨气和水，也可用碳酸氢铵或碳酸铵等来代替二氧化碳和氨气，其中中间体和二氧化碳的摩尔比在1－12之间，氨气和二氧化碳的比例在0.5－5之间，再向其中加入15－75倍摩尔比的水，加热到120℃到180℃之间，反应时间约4－20小时，反应完成后降温取出反应液浓缩完成后就直接得到草铵膦的铵盐。收率在80%以上。
Description
技术领域
本发明涉及一种农药草铵膦参见式(Ⅰ)及其与酸或碱的盐的合成方法，是一种通过施特雷克（strecker）反应制备农药草铵膦的合成方法，将式(Ⅱ)的中间体化合物（3－腈基－3－羟基）丙基甲基膦酸与二氧化碳和氨气在水溶液中直接反应合成农药草铵膦及其与酸或碱的盐的方法。
(Ⅰ)
(Ⅱ)
背景技术
草铵膦(参见式(Ⅰ))是活性化合物(D，L)一2-氨基-4－（羟基(甲基)氧膦基）丁酸的俗名，市售产品为单铵盐类的形式，并可作为喷洒在叶面上的除草剂(参见DE - A - 2717440, US -A-4168963)。草铵膦是内吸传导型除草剂，具有广谱杀草活性，广泛用于油菜、玉米、棉花、大豆和水稻的除草。草铵膦的分子结构有L型和D型两种光学立体结构，其中L-型为生物活性结构；D-型无生物活性，国际市场上销售的草铵膦为消旋体。对未出土的幼芽和种子无害。受害植物失绿后呈黄白色，2~5天后开始枯黄死去。接触土壤后失去活性，只宜作苗后茎叶喷雾。
对草铵膦的合成方法已经有大量的研究和实验结果，其中最有代表性的是CN1267305A中，赫彻斯特一舍林农业发展有限公司公布的一种草铵膦及其中间体的合成方法。草铵膦可用多步骤合成，由甲基膦化合物，例如甲基亚膦酸二乙酯等与不饱和的酮或醛类化合物比如丙烯醛，反应产生加合物， 经后续的施特雷克（strecker）反应及最终的氨基腈水解， 在合成氨基腈的过程中需要用到原料是NH3、NaCN、NH4Cl，然后将氨基腈化合物，使用盐酸或氢氧化钠来水解产生草铵膦。
在化学法合成农药草铵膦的生产过程中，在目前已知的合成文献当中，最具代表性的是将氨基腈化合物使用盐酸或氢氧化钠来水解产生草铵膦，该方法有一个明显的缺点，就是会产生大量的盐，其中主要是氯化钠，导致在工业生产当中存在着氯化钠和产品的分离这一步骤，而由于草铵膦和氯化钠溶解性能有一定的相似之处，比如都溶解于水等，使这一步物理过程变的并不容易，目前都是用甲醇来离析产品当中的氯化钠，这样的一个操作会占用大量的设备，添加进去了合成工艺当中原来没有的原料甲醇，并带来较高的操作成本。本发明就是针对这一问题，发明了一条新的工艺路线来避免了产品和氯化钠的分离。
发明内容
将式(Ⅱ)的中间体化合物加入到高压釜中，然后加入二氧化碳和氨气和水，也可用碳酸氢铵或碳酸铵等来代替二氧化碳和氨气，其中式(Ⅱ)的中间体和二氧化碳的摩尔比在1－12之间，氨气和二氧化碳的比例在0.5－5之间，再向其中加入15－75倍摩尔比的水，加热到120℃到180℃之间，反应时间约4－20小时，反应完成后降温取出反应液浓缩完成后就直接得到草铵膦的单铵盐，一般这样的产品就可以直接销售，如果再通过一根阳离子树脂柱就可以得到草铵膦。收率在80%以上。
实施实例一 取式（Ⅱ）的中间体45.6克，碳酸氢铵132克，水227克。加料完毕后，在150℃反应6小时，取出在旋转蒸发仪内旋干，结晶得到40.2克草铵膦单铵盐，纯度92%。
实施实例二 取式（Ⅱ）的中间体52.3克，碳酸铵160克，水260克。加料完毕后，在150℃反应6小时，取出在旋转蒸发仪内旋干，结晶得到45.2克草铵膦单铵盐，纯度93%。
Claims (2)
1.一种从式(Ⅱ)的化合物制备式(Ⅰ)化合物或其与酸或碱的盐类的方法，
(Ⅱ)
将式(Ⅱ)的中间体在二氧化碳、氨、和水存在下120－180度共同反应4－20小时，反应完成后降温取出反应液浓缩完成后就直接得到式(Ⅰ)化合物的铵盐。
2.其中式(Ⅱ)的中间体和二氧化碳的摩尔比在1－12之间，氨气和二氧化碳的比例在0.5－5之间，式(Ⅱ)的中间体与水的摩尔比在15－75倍之间。
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483379A (zh) * | 2013-09-26 | 2014-01-01 | 江苏辉丰农化股份有限公司 | 一种草铵膦酸的制备方法 |
| WO2015173146A1 (de) | 2014-05-13 | 2015-11-19 | Bayer Cropscience Ag | Verfahren zur herstellung von phosphorhaltigen cyanhydrinen |
| EP3392237A1 (de) | 2017-04-21 | 2018-10-24 | Evonik Degussa GmbH | Verfahren zur herstellung von acroleincyanhydrinen |
| US10912301B2 (en) | 2015-05-11 | 2021-02-09 | Basf Se | Herbicide combinations comprising L-glufosinate and indaziflam |
| CN113072579A (zh) * | 2021-04-13 | 2021-07-06 | 河北威远生物化工有限公司 | 一种草铵膦的制备方法 |
| WO2024175643A1 (en) | 2023-02-23 | 2024-08-29 | Basf Se | A process for preparing l-glufosinate from cyanhydrine or cyanhydrine derivatives |
| WO2024256370A1 (en) | 2023-06-13 | 2024-12-19 | Basf Se | Synthesis of glufosinate using an amidase-based process |
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| CN1267305A (zh) * | 1997-08-20 | 2000-09-20 | 赫彻斯特-舍林农业发展有限公司 | 用于制备草胺膦的方法以及中间体 |
| WO2007034066A1 (fr) * | 2005-09-21 | 2007-03-29 | Adisseo France S.A.S. | Synthese de la methionine a partir de 2-hydroxy-4- (methylthio)butyronitrile, co2, nh3 et h2o en continu et sans isoler de produits intermediaires |
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| CN1267305A (zh) * | 1997-08-20 | 2000-09-20 | 赫彻斯特-舍林农业发展有限公司 | 用于制备草胺膦的方法以及中间体 |
| WO2007034066A1 (fr) * | 2005-09-21 | 2007-03-29 | Adisseo France S.A.S. | Synthese de la methionine a partir de 2-hydroxy-4- (methylthio)butyronitrile, co2, nh3 et h2o en continu et sans isoler de produits intermediaires |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483379A (zh) * | 2013-09-26 | 2014-01-01 | 江苏辉丰农化股份有限公司 | 一种草铵膦酸的制备方法 |
| WO2015173146A1 (de) | 2014-05-13 | 2015-11-19 | Bayer Cropscience Ag | Verfahren zur herstellung von phosphorhaltigen cyanhydrinen |
| US9850263B2 (en) | 2014-05-13 | 2017-12-26 | Bayer Cropscience Aktiengesellschaft | Process for preparing phosphorus containing cyanohydrins |
| US10961265B2 (en) | 2014-05-13 | 2021-03-30 | Basf Se | Process for preparing phosphorus containing cyanohydrins |
| US10912301B2 (en) | 2015-05-11 | 2021-02-09 | Basf Se | Herbicide combinations comprising L-glufosinate and indaziflam |
| TWI728974B (zh) * | 2015-05-11 | 2021-06-01 | 德商拜耳作物科學股份有限公司 | 包含ｌ-固殺草及茚嗪氟草胺之殺草劑組合 |
| EP3392237A1 (de) | 2017-04-21 | 2018-10-24 | Evonik Degussa GmbH | Verfahren zur herstellung von acroleincyanhydrinen |
| US10214484B2 (en) | 2017-04-21 | 2019-02-26 | Evonik Degussa Gmbh | Method for preparing acrolein cyanohydrins |
| CN113072579A (zh) * | 2021-04-13 | 2021-07-06 | 河北威远生物化工有限公司 | 一种草铵膦的制备方法 |
| WO2024175643A1 (en) | 2023-02-23 | 2024-08-29 | Basf Se | A process for preparing l-glufosinate from cyanhydrine or cyanhydrine derivatives |
| WO2024256370A1 (en) | 2023-06-13 | 2024-12-19 | Basf Se | Synthesis of glufosinate using an amidase-based process |
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