ZA200601864B - Process for purifying mesotrione - Google Patents
Process for purifying mesotrione Download PDFInfo
- Publication number
- ZA200601864B ZA200601864B ZA200601864A ZA200601864A ZA200601864B ZA 200601864 B ZA200601864 B ZA 200601864B ZA 200601864 A ZA200601864 A ZA 200601864A ZA 200601864 A ZA200601864 A ZA 200601864A ZA 200601864 B ZA200601864 B ZA 200601864B
- Authority
- ZA
- South Africa
- Prior art keywords
- mesotrione
- enolate
- solution
- nmsba
- purification
- Prior art date
Links
- 239000005578 Mesotrione Substances 0.000 title claims description 151
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 title claims description 151
- 238000000034 method Methods 0.000 title claims description 146
- 239000000243 solution Substances 0.000 claims description 82
- 239000012535 impurity Substances 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 50
- 238000011282 treatment Methods 0.000 claims description 49
- 238000000746 purification Methods 0.000 claims description 44
- 238000004821 distillation Methods 0.000 claims description 38
- 238000002425 crystallisation Methods 0.000 claims description 23
- 238000001179 sorption measurement Methods 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 claims description 13
- 238000010908 decantation Methods 0.000 claims description 13
- -1 enol ester Chemical class 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- 230000008707 rearrangement Effects 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 239000011591 potassium Substances 0.000 claims description 11
- SKDDBIWRHFHMKM-UHFFFAOYSA-N 4-methylsulfonyl-2-nitrobenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C([N+]([O-])=O)=C1 SKDDBIWRHFHMKM-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 111
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000010561 standard procedure Methods 0.000 description 15
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000011045 prefiltration Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000003021 water soluble solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OXBDLEXAVKAJFD-UHFFFAOYSA-N 1-methyl-4-methylsulfonyl-2-nitrobenzene Chemical compound CC1=CC=C(S(C)(=O)=O)C=C1[N+]([O-])=O OXBDLEXAVKAJFD-UHFFFAOYSA-N 0.000 description 1
- QNOUABMNRMROSL-UHFFFAOYSA-N 110964-79-9 Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QNOUABMNRMROSL-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0323090A GB0323090D0 (en) | 2003-10-02 | 2003-10-02 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200601864B true ZA200601864B (en) | 2007-07-25 |
Family
ID=29415377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200601864A ZA200601864B (en) | 2003-10-02 | 2006-03-03 | Process for purifying mesotrione |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN100378071C (ru) |
| GB (1) | GB0323090D0 (ru) |
| GT (1) | GT200400195A (ru) |
| UA (1) | UA82722C2 (ru) |
| ZA (1) | ZA200601864B (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100537530C (zh) * | 2007-06-08 | 2009-09-09 | 浙江工业大学 | 一种磺草酮的合成方法 |
| CN102649774A (zh) * | 2012-02-02 | 2012-08-29 | 北京颖泰嘉和生物科技有限公司 | 一种降低磺草酮中氰化物的方法 |
| CN103373946B (zh) * | 2012-04-23 | 2015-04-29 | 中国中化股份有限公司 | 一种制备稳定晶型硝磺草酮的方法 |
| CN103588685B (zh) * | 2013-10-18 | 2016-01-13 | 浙江省诸暨合力化学对外贸易有限公司 | 三酮类铵盐化合物及其制备方法及应用 |
| CN103910659B (zh) * | 2013-11-04 | 2016-05-11 | 迈克斯(如东)化工有限公司 | 2-硝基-4-甲磺酰基苯甲酸的精制方法及其中间体 |
| CN105712912B (zh) * | 2014-12-02 | 2017-09-01 | 浙江省诸暨合力化学对外贸易有限公司 | 一种三酮类化合物及其中间体的制备方法 |
| GB2530838B (en) * | 2015-06-08 | 2020-01-22 | Rotam Agrochem Int Co Ltd | Process for purifying mesotrione |
| CN106699616A (zh) * | 2016-11-17 | 2017-05-24 | 北京颖泰嘉和生物科技股份有限公司 | 一种新的2‑硝基‑4‑甲磺酰基苯甲酸的纯化方法 |
| CN110078647B (zh) * | 2019-05-15 | 2021-04-13 | 北京颖泰嘉和生物科技股份有限公司 | 一种硝磺草酮反应产物的后处理方法 |
| CN111440099B (zh) * | 2020-04-09 | 2022-01-04 | 利民化学有限责任公司 | 一种环磺酮产品的纯化方法 |
| CN111909066B (zh) * | 2020-06-24 | 2022-05-31 | 天津大学 | 一种提高硝磺草酮产品质量的结晶处理方法 |
| CN114671789B (zh) * | 2021-10-25 | 2023-11-03 | 上虞颖泰精细化工有限公司 | 一种硝磺草酮连续结晶的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9725135D0 (en) * | 1997-11-27 | 1998-01-28 | Zeneca Ltd | Chemical process |
| AU2002249384B2 (en) * | 2001-03-26 | 2007-06-07 | Syngenta Limited | Purification of 2-nitro-4-methylsulphonylbenzoic acid |
-
2003
- 2003-10-02 GB GB0323090A patent/GB0323090D0/en not_active Ceased
-
2004
- 2004-01-10 UA UAA200604618A patent/UA82722C2/ru unknown
- 2004-09-30 GT GT200400195A patent/GT200400195A/es unknown
- 2004-10-01 CN CNB2004800281851A patent/CN100378071C/zh active Active
-
2006
- 2006-03-03 ZA ZA200601864A patent/ZA200601864B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB0323090D0 (en) | 2003-11-05 |
| CN1860102A (zh) | 2006-11-08 |
| CN100378071C (zh) | 2008-04-02 |
| GT200400195A (es) | 2005-05-02 |
| UA82722C2 (ru) | 2008-05-12 |
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