CN106496215A - 噻虫嗪的高收率绿色环保合成方法 - Google Patents
噻虫嗪的高收率绿色环保合成方法 Download PDFInfo
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- CN106496215A CN106496215A CN201610979438.8A CN201610979438A CN106496215A CN 106496215 A CN106496215 A CN 106496215A CN 201610979438 A CN201610979438 A CN 201610979438A CN 106496215 A CN106496215 A CN 106496215A
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- diacloden
- environmental protection
- high yield
- synthetic method
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- NWWZPOKUUAIXIW-DHZHZOJOSA-N (E)-thiamethoxam Chemical compound [O-][N+](=O)/N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-DHZHZOJOSA-N 0.000 title claims abstract description 23
- 230000007613 environmental effect Effects 0.000 title claims abstract description 15
- 238000010189 synthetic method Methods 0.000 title claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 32
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000000047 product Substances 0.000 claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000003287 bathing Methods 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 9
- 230000008025 crystallization Effects 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000006227 byproduct Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 7
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 230000008014 freezing Effects 0.000 claims abstract description 5
- 238000007710 freezing Methods 0.000 claims abstract description 5
- 239000012452 mother liquor Substances 0.000 claims abstract description 5
- 238000011084 recovery Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 239000006228 supernatant Substances 0.000 claims abstract description 5
- 238000013461 design Methods 0.000 claims abstract description 3
- 239000002920 hazardous waste Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000012805 post-processing Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- -1 potassium halide Chemical class 0.000 claims description 4
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- UZAOOCPKYMGRHG-UHFFFAOYSA-N 5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=CS1 UZAOOCPKYMGRHG-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000002351 wastewater Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002893 slag Substances 0.000 description 3
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical compound N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 229930014345 anabasine Natural products 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFNQLYDPNAZRCH-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O.OC(O)=O HFNQLYDPNAZRCH-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- NHSCRWJPZDNMBU-UHFFFAOYSA-L dipotassium carbonic acid carbonate Chemical compound [K+].[K+].OC([O-])=O.OC([O-])=O NHSCRWJPZDNMBU-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 239000003992 organochlorine insecticide Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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CN201610979438.8A CN106496215B (zh) | 2016-11-08 | 2016-11-08 | 噻虫嗪的高收率绿色环保合成方法 |
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CN201610979438.8A CN106496215B (zh) | 2016-11-08 | 2016-11-08 | 噻虫嗪的高收率绿色环保合成方法 |
Publications (2)
Publication Number | Publication Date |
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CN106496215A true CN106496215A (zh) | 2017-03-15 |
CN106496215B CN106496215B (zh) | 2020-04-07 |
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CN201610979438.8A Active CN106496215B (zh) | 2016-11-08 | 2016-11-08 | 噻虫嗪的高收率绿色环保合成方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108822098A (zh) * | 2018-06-29 | 2018-11-16 | 湖北犇星农化有限责任公司 | 一种噻虫嗪的制备方法 |
CN111036158A (zh) * | 2019-12-28 | 2020-04-21 | 邯郸市瑞田农药有限公司 | 一种2氯-5氯甲基噻唑合成反应*** |
CN115286624A (zh) * | 2022-08-04 | 2022-11-04 | 内蒙古犇星化学有限公司 | 一种噻虫嗪的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1084171A (zh) * | 1992-07-22 | 1994-03-23 | 希巴-盖吉股份公司 | 噁二嗪衍生物 |
WO1997010226A1 (en) * | 1995-09-11 | 1997-03-20 | Novartis Ag | Process for preparing a 2-chloro-5-chloromethyl-thiazole compound |
CN102372702A (zh) * | 2011-11-17 | 2012-03-14 | 安徽省化工研究院 | 噻虫嗪的制备方法 |
CN105175407A (zh) * | 2014-05-28 | 2015-12-23 | 龙灯农业化工国际有限公司 | 噻虫嗪及其用途 |
-
2016
- 2016-11-08 CN CN201610979438.8A patent/CN106496215B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1084171A (zh) * | 1992-07-22 | 1994-03-23 | 希巴-盖吉股份公司 | 噁二嗪衍生物 |
WO1997010226A1 (en) * | 1995-09-11 | 1997-03-20 | Novartis Ag | Process for preparing a 2-chloro-5-chloromethyl-thiazole compound |
CN102372702A (zh) * | 2011-11-17 | 2012-03-14 | 安徽省化工研究院 | 噻虫嗪的制备方法 |
CN105175407A (zh) * | 2014-05-28 | 2015-12-23 | 龙灯农业化工国际有限公司 | 噻虫嗪及其用途 |
Non-Patent Citations (1)
Title |
---|
MAIENFISCH,等: "Synthesis and Properties of Thiamethoxam and Related Compounds", 《ZEITSCHRIFT FUER NATURFORSCHUNG, B: CHEMICAL SCIENCES》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108822098A (zh) * | 2018-06-29 | 2018-11-16 | 湖北犇星农化有限责任公司 | 一种噻虫嗪的制备方法 |
CN111036158A (zh) * | 2019-12-28 | 2020-04-21 | 邯郸市瑞田农药有限公司 | 一种2氯-5氯甲基噻唑合成反应*** |
CN115286624A (zh) * | 2022-08-04 | 2022-11-04 | 内蒙古犇星化学有限公司 | 一种噻虫嗪的制备方法 |
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CN106496215B (zh) | 2020-04-07 |
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C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: High yield green synthesis method of thiamethoxam Effective date of registration: 20230105 Granted publication date: 20200407 Pledgee: Bank of China Limited by Share Ltd. Handan branch Pledgor: Handan Ruitian Pesticide Co.,Ltd. Registration number: Y2023130000005 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20200407 Pledgee: Bank of China Limited by Share Ltd. Handan branch Pledgor: Handan Ruitian Pesticide Co.,Ltd. Registration number: Y2023130000005 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: High yield green and environmentally friendly synthesis method of thiamethoxam Granted publication date: 20200407 Pledgee: Bank of China Limited by Share Ltd. Handan branch Pledgor: Handan Ruitian Pesticide Co.,Ltd. Registration number: Y2024980002341 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20200407 Pledgee: Bank of China Limited by Share Ltd. Handan branch Pledgor: Handan Ruitian Pesticide Co.,Ltd. Registration number: Y2024980002341 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: High yield green and environmentally friendly synthesis method of thiamethoxam Granted publication date: 20200407 Pledgee: Bank of China Limited by Share Ltd. Handan branch Pledgor: Handan Ruitian Pesticide Co.,Ltd. Registration number: Y2024980005890 |