WO2018039843A1 - Process for preparing glyphosate - Google Patents
Process for preparing glyphosate Download PDFInfo
- Publication number
- WO2018039843A1 WO2018039843A1 PCT/CN2016/097094 CN2016097094W WO2018039843A1 WO 2018039843 A1 WO2018039843 A1 WO 2018039843A1 CN 2016097094 W CN2016097094 W CN 2016097094W WO 2018039843 A1 WO2018039843 A1 WO 2018039843A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- added
- solution
- stirring
- catalyst
- glyphosate
- Prior art date
Links
- 239000005562 Glyphosate Substances 0.000 title claims abstract description 10
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229940097068 glyphosate Drugs 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000003756 stirring Methods 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229950009195 phenylpropanol Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Definitions
- the invention relates to a preparation process of glyphosate, and belongs to the field of chemical processing.
- Phenylpropanol is an important pharmaceutical and chemical intermediate. It is the backbone of many natural products and drugs. It is the core structure of many medicines and many new drugs currently under development.
- the preparation of the prior art 1% glyphosate has the following disadvantages: (1) the preparation of raw materials is expensive and the required cost is high; (2) the preparation process is complicated and the work efficiency is low; (3) the preparation of raw materials is difficult, the separation is difficult, and the production is difficult. The rate is lowered; therefore, there is an urgent need to develop a low-cost and high-efficiency 1% glyphosate preparation process, and no technical solutions identical or similar to the present invention have been found by searching.
- the technical problem to be solved by the present invention is to provide a process for preparing 1% glyphosate which is low in cost and high in production efficiency.
- the technical solution of the present invention is: a preparation process of glyphosate, and the innovation is as follows: the preparation process is as follows:
- the 2-halogen substitute and the o-hydroxyl are used as raw materials for preparation, and the raw material is cheap and easy to obtain, and the reaction time is short, the operation is simple, the product is easy to be purified, the noble catalyst is not used, the yield is high, and the pollution is small.
- the invention discloses a preparation process of glyphosate, and the preparation process is as follows:
- the 2-halogen substituent and the o-hydroxyl group are sequentially added to the solvent while stirring, and after stirring uniformly, potassium carbonate is added and placed at a temperature of 150 ° C for 2 h; wherein the 2-halogen substituent and the o-hydroxy group are present.
- the ratio of solvent and potassium carbonate is 1:1:10:10.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
Abstract
Provided is a process for preparing glyphosate. Firstly, a 2-halogen substituted compound and an ortho-hydroxy compound are successively added to a solvent with stirring, and after uniformly stirring, an alkaline solution is then added, and the mixture is placed at a temperature of 200ºC and reacted for 1 hour; the solution is cooled to room temperature and a catalyst is added, and a catalytic reaction is carried out for 30 minutes; and finally, hydrochloric acid is then added to the solution and stirred at a high speed to carry out acidification decarboxylation for 0.5 h, and the stirring speed is controlled at 500 r/min. The advantages lie in that the 2-halogen substituted compound and the ortho-hydroxy compound are used as preparation raw materials, the raw materials are cheap and easily obtained; meanwhile, the reaction time is short, the operation is simple, the product is easily purified, no precious catalyst is used, the yield is high and pollution is low.
Description
技术领域Technical field
本发明涉及草甘膦的制备工艺，属于化学物品加工领域。The invention relates to a preparation process of glyphosate, and belongs to the field of chemical processing.
背景技术Background technique
苯丙呋喃是一种重要的医药化工中间体，是许多天然产物，药物的结构主体骨架，是多种医药以及许多目前正在开发新药的核心结构。Phenylpropanol is an important pharmaceutical and chemical intermediate. It is the backbone of many natural products and drugs. It is the core structure of many medicines and many new drugs currently under development.
现有技术的1%草甘膦的制备存在以下缺点：（1）制备原料价格昂贵，所需成本高；（2）制备过程繁杂，工作效率低；（3）原料制备困难，分离困难，产率下降；因此急需研制一种成本低且生产效率高的1%草甘膦的制备工艺，经检索，未发现与本发明相同或相似的技术方案。The preparation of the prior art 1% glyphosate has the following disadvantages: (1) the preparation of raw materials is expensive and the required cost is high; (2) the preparation process is complicated and the work efficiency is low; (3) the preparation of raw materials is difficult, the separation is difficult, and the production is difficult. The rate is lowered; therefore, there is an urgent need to develop a low-cost and high-efficiency 1% glyphosate preparation process, and no technical solutions identical or similar to the present invention have been found by searching.
发明内容Summary of the invention
本发明要解决的技术问题是提供一种成本低且生产效率高的1%草甘膦的制备工艺。The technical problem to be solved by the present invention is to provide a process for preparing 1% glyphosate which is low in cost and high in production efficiency.
为解决上述技术问题，本发明的技术方案为：一种草甘膦的制备工艺，其创新点在于：所述制备工艺具体如下：In order to solve the above technical problem, the technical solution of the present invention is: a preparation process of glyphosate, and the innovation is as follows: the preparation process is as follows:
（1）将2-卤素取代物及邻羟基物依次边搅拌边加入溶剂中，搅拌均匀后再加入碱溶液并放置在200℃的温度下反应1h；(1) The 2-halogen substituent and the o-hydroxyl group are added to the solvent while stirring, and after stirring uniformly, the alkali solution is added and placed at a temperature of 200 ° C for 1 h;
（2）将溶液降至室温并加入催化剂，催化反应30min；(2) reducing the solution to room temperature and adding a catalyst, catalyzing the reaction for 30 min;
（3）再向溶液中加入盐酸并高速搅拌，使其酸化脱羧0.5h，搅拌速度控制为500r/min。(3) Hydrochloric acid was further added to the solution and stirred at a high speed to acidify and decarboxylate for 0.5 h, and the stirring speed was controlled to 500 r/min.
本发明的优点在于：The advantages of the invention are:
（1）采用2-卤素取代物及邻羟基物作为制备原料，该原料便宜易得，同时反应时间短，操作简单，产品容易纯化，不用贵重催化剂，产率高，污染小。(1) The 2-halogen substitute and the o-hydroxyl are used as raw materials for preparation, and the raw material is cheap and easy to obtain, and the reaction time is short, the operation is simple, the product is easy to be purified, the noble catalyst is not used, the yield is high, and the pollution is small.
（2）反应过程中加入二氧化锰催化剂，加快反应速度，提高生产效率。(2) Adding manganese dioxide catalyst during the reaction to accelerate the reaction rate and improve production efficiency.
具体实施方式detailed description
实施例1 Example 1
本发明公开了一种草甘膦的制备工艺，该制备工艺具体如下：The invention discloses a preparation process of glyphosate, and the preparation process is as follows:
（1）将2-卤素取代物及邻羟基物依次边搅拌边加入溶剂中，其搅拌均匀后再加入碳酸钾并放置在150℃的温度下反应2h；其中2-卤素取代物、邻羟基物、溶剂及碳酸钾的配置比例为1:1:10:10。(1) The 2-halogen substituent and the o-hydroxyl group are sequentially added to the solvent while stirring, and after stirring uniformly, potassium carbonate is added and placed at a temperature of 150 ° C for 2 h; wherein the 2-halogen substituent and the o-hydroxy group are present. The ratio of solvent and potassium carbonate is 1:1:10:10.
（2）将溶液降至室温并加入二氧化锰，催化反应45min；(2) reducing the solution to room temperature and adding manganese dioxide, catalyzing the reaction for 45 min;
（3）再向溶液中加入盐酸并高速搅拌，使其酸化脱羧0.5h，搅拌速度控制为500r/min。(3) Hydrochloric acid was further added to the solution and stirred at a high speed to acidify and decarboxylate for 0.5 h, and the stirring speed was controlled to 500 r/min.
以上显示和描述了本发明的基本原理和主要特征。本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明精神和范围的前提下，本发明还会有各种变化和改进，这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。
The basic principles and main features of the present invention have been shown and described above. It should be understood by those skilled in the art that the present invention is not limited by the foregoing embodiments, and that the present invention is only described in the foregoing description and the description of the present invention, without departing from the spirit and scope of the invention. Various changes and modifications are intended to be included within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and their equivalents.
Claims (1)
- 一种草甘膦的制备工艺，其特征在于：所述制备工艺具体如下：A preparation process of glyphosate, characterized in that the preparation process is as follows:（1）将2-卤素取代物及邻羟基物依次边搅拌边加入溶剂中，搅拌均匀后再加入碱溶液并放置在200℃的温度下反应1h；(1) The 2-halogen substituent and the o-hydroxyl group are added to the solvent while stirring, and after stirring uniformly, the alkali solution is added and placed at a temperature of 200 ° C for 1 h;（2）将溶液降至室温并加入催化剂，催化反应30min；(2) reducing the solution to room temperature and adding a catalyst, catalyzing the reaction for 30 min;（3）再向溶液中加入盐酸并高速搅拌，使其酸化脱羧0.5h，搅拌速度控制为500r/min。(3) Hydrochloric acid was further added to the solution and stirred at a high speed to acidify and decarboxylate for 0.5 h, and the stirring speed was controlled to 500 r/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2016/097094 WO2018039843A1 (en) | 2016-08-29 | 2016-08-29 | Process for preparing glyphosate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2016/097094 WO2018039843A1 (en) | 2016-08-29 | 2016-08-29 | Process for preparing glyphosate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2018039843A1 true WO2018039843A1 (en) | 2018-03-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2016/097094 WO2018039843A1 (en) | 2016-08-29 | 2016-08-29 | Process for preparing glyphosate |
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| Country | Link |
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| WO (1) | WO2018039843A1 (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364880A (en) * | 1993-06-16 | 1994-11-15 | Advanced Therapies, Inc. | Compound for treatment of cardiac arrhythmia, synthesis, and methods of use |
| CN1858042A (en) * | 2006-06-09 | 2006-11-08 | 赵金浩 | Synthetic process for 2-butyl-3(hydroxy 3,5-diiodo-benzoyl) benzofuran |
| CN101830872A (en) * | 2010-04-14 | 2010-09-15 | 南方医科大学 | Synthetic method of 3-hydroxyl benzofuran derivatives |
| CN102653529A (en) * | 2011-10-25 | 2012-09-05 | 广东医学院 | Preparation process of benzofuran |
| CN104628686A (en) * | 2015-01-27 | 2015-05-20 | 南通恒盛精细化工有限公司 | Preparation process of benzofuran with amide side chain |
-
2016
- 2016-08-29 WO PCT/CN2016/097094 patent/WO2018039843A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364880A (en) * | 1993-06-16 | 1994-11-15 | Advanced Therapies, Inc. | Compound for treatment of cardiac arrhythmia, synthesis, and methods of use |
| CN1858042A (en) * | 2006-06-09 | 2006-11-08 | 赵金浩 | Synthetic process for 2-butyl-3(hydroxy 3,5-diiodo-benzoyl) benzofuran |
| CN101830872A (en) * | 2010-04-14 | 2010-09-15 | 南方医科大学 | Synthetic method of 3-hydroxyl benzofuran derivatives |
| CN102653529A (en) * | 2011-10-25 | 2012-09-05 | 广东医学院 | Preparation process of benzofuran |
| CN104628686A (en) * | 2015-01-27 | 2015-05-20 | 南通恒盛精细化工有限公司 | Preparation process of benzofuran with amide side chain |
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