CN112321474A - Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide - Google Patents
Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide Download PDFInfo
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- CN112321474A CN112321474A CN202011484356.9A CN202011484356A CN112321474A CN 112321474 A CN112321474 A CN 112321474A CN 202011484356 A CN202011484356 A CN 202011484356A CN 112321474 A CN112321474 A CN 112321474A
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- China
- Prior art keywords
- reactor
- liquid mixing
- tricyclazole
- mixing pipe
- burette
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- 238000000034 method Methods 0.000 title claims abstract description 23
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 8
- YRABENKRWXQGMK-UHFFFAOYSA-N (2-methylanilino)thiourea Chemical compound CC1=CC=CC=C1NNC(N)=S YRABENKRWXQGMK-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 35
- 238000002156 mixing Methods 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 8
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 5
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 230000002194 synthesizing effect Effects 0.000 claims abstract 6
- ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 claims description 8
- 210000001503 joint Anatomy 0.000 claims description 3
- 238000005192 partition Methods 0.000 claims description 3
- SFMWWKUSCXABIB-UHFFFAOYSA-N (2-methylsulfanylphenyl)thiourea Chemical compound CSC1=CC=CC=C1NC(N)=S SFMWWKUSCXABIB-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- YDAKEVOYUPFWFX-UHFFFAOYSA-N (2-methylphenyl)methylthiourea Chemical compound CC1=CC=CC=C1CNC(N)=S YDAKEVOYUPFWFX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide. Adopting o-toluidine and ammonium thiocyanate as raw materials, and synthesizing the tricyclazole intermediate o-methylbenzylthiourea by adopting a continuous ratio dropwise adding method in the presence of sulfuric acid; the device is structurally realized by adopting a device which comprises a plurality of burettes for dripping materials, wherein the burettes are annularly arranged and are arranged in an inverted frustum structure form, the lower parts of the burettes are provided with liquid mixing pipes communicated with the burettes, liquid inlets at the top and liquid outlets at the bottom of the liquid mixing pipes form horn mouths, and a main body of the liquid mixing pipe is spiral and is provided with a driving device for driving the liquid mixing pipe to rotate; the lower part of the liquid mixing pipe is provided with a reactor communicated with the liquid mixing pipe, the reactor is driven by a driving device to rotate, and a stirring device is arranged in the reactor. The invention adopts a continuous proportioning dropwise adding process, so that each reaction material reacts more uniformly in the reaction process, the reaction quality is improved, and the product yield is improved.
Description
Technical Field
The invention relates to a synthesis process of tricyclazole intermediate o-methylphenylthiourea, belonging to the technical field of pesticides.
Background
The tricyclazole is a protective bactericide with systemic property, has no chronic toxicity, is safe to aquatic organisms and non-toxic to bees, and is one of the main pesticide bactericides for rice blast commonly used at home and abroad at present.
With the progress of human society and the attention of human beings on ecological environment, the internal product structure of the pesticide industry is correspondingly adjusted, high-height and high-residue pesticide varieties are gradually eliminated, and high-efficiency, low-toxicity and low-residue pesticide varieties are replaced; the proportion of the pesticide to the total pesticide product is gradually decreasing, and the proportion of the bactericide to the total pesticide product is gradually increasing.
Therefore, it is significant how to further improve the production quality of the tricyclazole and further improve the utilization rate of the tricyclazole.
Disclosure of Invention
The invention provides a synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide, which can further improve the production quality of tricyclazole.
The technical scheme adopted by the invention is as follows: the synthesis process of the tricyclazole intermediate o-methylphenyl thiourea adopts o-toluidine and ammonium thiocyanate as raw materials, and adopts a continuous proportion dropwise adding method to synthesize the tricyclazole intermediate o-methylphenyl thiourea in the presence of sulfuric acid;
the continuous proportioning and dripping method is realized by adopting a device structure, the device comprises a plurality of burettes for dripping materials, the burettes are annularly arranged and are arranged in an inverted frustum structure, a liquid mixing pipe communicated with the burettes is arranged at the lower part of each burette, a liquid inlet at the top part and a liquid outlet at the bottom part of the liquid mixing pipe form bell mouths, and a main body of the liquid mixing pipe is spiral and is provided with a driving device for driving the liquid mixing pipe to rotate;
the lower part of the liquid mixing pipe is provided with a reactor communicated with the liquid mixing pipe, the reactor is driven by a driving device to rotate, and a stirring device is arranged in the reactor.
Furthermore, each burette is provided with a flow regulating valve.
Further, a return pipeline is arranged at the bottom of the reactor, extends to the upper part of the reactor and is communicated with the upper part of the reactor.
Further, a cover plate is arranged at the joint of the bottom of the reactor and the return pipe, and the cover plate can move to form two states: namely, the bottom of the reactor is communicated or separated with the return pipe.
Further, the device also comprises the following structure: the burette is characterized in that a vibration ring connected with each burette is arranged outside each burette, a sleeve pipe in butt joint is arranged on the side part of each vibration ring and each burette, and a flexible connecting piece is arranged in each sleeve pipe.
Furthermore, the flexible connecting piece is of a piston structure and comprises a sleeve arranged in the sleeve, the sleeve is divided into two isolated parts by a partition plate in the sleeve, air holes are formed in the two sides of the sleeve, and pressure of the two parts of the sleeve is adjusted through the air holes.
The invention has the advantages that: the invention adopts a continuous proportioning dropwise adding process, so that each reaction material reacts more uniformly in the reaction process, the reaction quality is improved, and the product yield is improved.
Drawings
FIG. 1 is a schematic structural diagram of the present invention.
Fig. 2 is an enlarged view of a portion a in fig. 1.
In the figure, 1 is a burette, 2 is a liquid mixing pipe, 3 is a reactor, 4 is a stirring device, 5 is a cover plate, 6 is a return pipeline, 7 is a vibration ring, 8 is a sleeve, 9 is a piston and 10 is an air hole.
Detailed Description
The synthesis process of the tricyclazole intermediate o-methylphenyl thiourea adopts o-toluidine and ammonium thiocyanate as raw materials, and adopts a continuous proportion dropwise adding method to synthesize the tricyclazole intermediate o-methylphenyl thiourea in the presence of sulfuric acid;
the continuous proportioning and dripping method is realized by adopting a device structure, the device comprises a plurality of burettes for dripping materials, the burettes are annularly arranged and are arranged in an inverted frustum structure, a liquid mixing pipe communicated with the burettes is arranged at the lower part of each burette, a liquid inlet at the top part and a liquid outlet at the bottom part of the liquid mixing pipe form bell mouths, and a main body of the liquid mixing pipe is spiral and is provided with a driving device for driving the liquid mixing pipe to rotate;
the lower part of the liquid mixing pipe is provided with a reactor communicated with the liquid mixing pipe, the reactor is driven by a driving device to rotate, and a stirring device is arranged in the reactor.
Furthermore, each burette is provided with a flow regulating valve.
Further, a return pipeline is arranged at the bottom of the reactor, extends to the upper part of the reactor and is communicated with the upper part of the reactor.
Further, a cover plate is arranged at the joint of the bottom of the reactor and the return pipe, and the cover plate can move to form two states: namely, the bottom of the reactor is communicated or separated with the return pipe.
Further, the device also comprises the following structure: the burette is characterized in that a vibration ring connected with each burette is arranged outside each burette, a sleeve pipe in butt joint is arranged on the side part of each vibration ring and each burette, and a flexible connecting piece is arranged in each sleeve pipe.
Furthermore, the flexible connecting piece is of a piston structure and comprises a sleeve arranged in the sleeve, the sleeve is divided into two isolated parts by a partition plate in the sleeve, air holes are formed in the two sides of the sleeve, and pressure of the two parts of the sleeve is adjusted through the air holes.
The invention will be further explained below for a better understanding of the invention: the invention adopts a continuous proportioning dropping process, each reaction material is added through a respective burette, and under the action of the gravity of the burette, each reaction material enters the liquid mixing pipe at a certain speed for mixing.
The reactor is arranged in a mode that the reflux pipeline is arranged to enable materials to form a circular flow mode in the reactor, and surface-surface mixing is achieved.
The structure of the vibration ring outside the burette of the invention enables the vibration ring to drive each burette to vibrate in small amplitude, so that materials entering the burette can smoothly enter the liquid mixing pipe through each burette, and meanwhile, the burette and the vibration ring are connected by adopting a piston structure form, thus realizing the adjustment of the vibration amplitude of the burette by the adjustment of the piston damping, and further improving the reaction quality and efficiency.
Claims (6)
1. The synthesis process of the tricyclazole intermediate o-methylphenyl thiourea is characterized in that o-toluidine and ammonium thiocyanate are used as raw materials, and the tricyclazole intermediate o-methylphenyl thiourea is synthesized by adopting a continuous proportioning dropwise adding method in the presence of sulfuric acid;
the continuous proportioning and dripping method is realized by adopting a device structure, the device comprises a plurality of burettes for dripping materials, the burettes are annularly arranged and are arranged in an inverted frustum structure, a liquid mixing pipe communicated with the burettes is arranged at the lower part of each burette, a liquid inlet at the top part and a liquid outlet at the bottom part of the liquid mixing pipe form bell mouths, and a main body of the liquid mixing pipe is spiral and is provided with a driving device for driving the liquid mixing pipe to rotate;
the lower part of the liquid mixing pipe is provided with a reactor communicated with the liquid mixing pipe, the reactor is driven by a driving device to rotate, and a stirring device is arranged in the reactor.
2. The process for synthesizing tricyclazole intermediate o-methylphenylthiourea as claimed in claim 1, wherein each burette is provided with a flow control valve.
3. The process for synthesizing tricyclazole intermediate o-methylthiophenyl thiourea according to claim 1, wherein a return line is provided at the bottom of the reactor, and the return line extends to and communicates with the upper part of the reactor.
4. The process for synthesizing tricyclazole intermediate o-methylthiophenyl thiourea as claimed in claim 3, wherein a cover plate is arranged at the joint of the bottom of the reactor and the return pipe, and the cover plate can move to form two states: namely, the bottom of the reactor is communicated or separated with the return pipe.
5. The process for synthesizing tricyclazole intermediate o-methylthiophenyl thiourea as claimed in claim 3, wherein said apparatus further comprises the following structure: the burette is characterized in that a vibration ring connected with each burette is arranged outside each burette, a sleeve pipe in butt joint is arranged on the side part of each vibration ring and each burette, and a flexible connecting piece is arranged in each sleeve pipe.
6. The process for synthesizing tricyclazole intermediate o-methylthiourea according to claim 5, wherein the flexible connecting member is a piston structure comprising a sleeve disposed in the sleeve, the sleeve is divided into two parts by a partition, the two sides of the sleeve are provided with air holes, and the pressure in the two parts of the sleeve is adjusted through the air holes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011484356.9A CN112321474A (en) | 2020-12-16 | 2020-12-16 | Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011484356.9A CN112321474A (en) | 2020-12-16 | 2020-12-16 | Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112321474A true CN112321474A (en) | 2021-02-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011484356.9A Pending CN112321474A (en) | 2020-12-16 | 2020-12-16 | Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide |
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| CN (1) | CN112321474A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993074A (en) * | 2012-11-29 | 2013-03-27 | 江苏长青农化股份有限公司 | Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole |
| CN107827912A (en) * | 2017-11-03 | 2018-03-23 | 江苏恒隆作物保护有限公司 | A kind of production method of Mensurating Tricyclazole Technical |
| CN107935897A (en) * | 2017-11-02 | 2018-04-20 | 南京工业大学连云港工业技术研究院 | The synthesis technique of o-tolyl thiocarbamide |
| CN210279095U (en) * | 2019-05-28 | 2020-04-10 | 无锡海特圣大光电材料科技有限公司 | Spiral stirring and feeding device for producing dimethomorph |
-
2020
- 2020-12-16 CN CN202011484356.9A patent/CN112321474A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993074A (en) * | 2012-11-29 | 2013-03-27 | 江苏长青农化股份有限公司 | Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole |
| CN107935897A (en) * | 2017-11-02 | 2018-04-20 | 南京工业大学连云港工业技术研究院 | The synthesis technique of o-tolyl thiocarbamide |
| CN107827912A (en) * | 2017-11-03 | 2018-03-23 | 江苏恒隆作物保护有限公司 | A kind of production method of Mensurating Tricyclazole Technical |
| CN210279095U (en) * | 2019-05-28 | 2020-04-10 | 无锡海特圣大光电材料科技有限公司 | Spiral stirring and feeding device for producing dimethomorph |
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Application publication date: 20210205 |