CN102532102A - 一种灭草烟的制备方法 - Google Patents
一种灭草烟的制备方法 Download PDFInfo
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- CN102532102A CN102532102A CN2011104555458A CN201110455545A CN102532102A CN 102532102 A CN102532102 A CN 102532102A CN 2011104555458 A CN2011104555458 A CN 2011104555458A CN 201110455545 A CN201110455545 A CN 201110455545A CN 102532102 A CN102532102 A CN 102532102A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000006482 condensation reaction Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000003377 acid catalyst Substances 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 15
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 14
- 230000020477 pH reduction Effects 0.000 claims abstract description 12
- -1 dimethyl butyrate Chemical compound 0.000 claims description 37
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
- 241000196324 Embryophyta Species 0.000 claims description 17
- 235000019504 cigarettes Nutrition 0.000 claims description 15
- 230000008029 eradication Effects 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000007942 carboxylates Chemical class 0.000 abstract 2
- YCPQUHCGFDFLSI-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanamide Chemical compound CC(C)C(C)(N)C(N)=O YCPQUHCGFDFLSI-UHFFFAOYSA-N 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 33
- 239000007787 solid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003570 biosynthesizing effect Effects 0.000 description 1
- 150000005693 branched-chain amino acids Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
实施例编号 | 异构体含量(wt%) | 收率(wt%) |
实施例1 | 2 | 92.6 |
实施例2 | 4 | 90.1 |
实施例3 | 3 | 90.1 |
对比例1 | 10 | 71.3 |
实施例4 | 8 | 80.7 |
实施例5 | 8 | 80.7 |
实施例6 | 8 | 80.7 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201110455545.8A CN102532102B (zh) | 2011-12-30 | 2011-12-30 | 一种灭草烟的制备方法 |
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CN201110455545.8A CN102532102B (zh) | 2011-12-30 | 2011-12-30 | 一种灭草烟的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN102532102A true CN102532102A (zh) | 2012-07-04 |
CN102532102B CN102532102B (zh) | 2014-01-08 |
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CN201110455545.8A Active CN102532102B (zh) | 2011-12-30 | 2011-12-30 | 一种灭草烟的制备方法 |
Country Status (1)
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CN (1) | CN102532102B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017071414A1 (en) * | 2015-10-29 | 2017-05-04 | Rotam Agrochem International Company Limited | Novel crystalline form of imazapyr, its preparation and use |
CN112142714A (zh) * | 2019-06-27 | 2020-12-29 | 山东润博生物科技有限公司 | 一种灭草烟的合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0095105A2 (en) * | 1982-05-25 | 1983-11-30 | American Cyanamid Company | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)-nicotinic acids, quinoline-3-carboxylic acids, and benzoic acids |
EP0133310A1 (en) * | 1983-08-02 | 1985-02-20 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
US4758667A (en) * | 1986-02-10 | 1988-07-19 | Ciba-Geigy Corporation | Process for the preparation of 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids |
-
2011
- 2011-12-30 CN CN201110455545.8A patent/CN102532102B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0095105A2 (en) * | 1982-05-25 | 1983-11-30 | American Cyanamid Company | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)-nicotinic acids, quinoline-3-carboxylic acids, and benzoic acids |
EP0133310A1 (en) * | 1983-08-02 | 1985-02-20 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
US4758667A (en) * | 1986-02-10 | 1988-07-19 | Ciba-Geigy Corporation | Process for the preparation of 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids |
Non-Patent Citations (1)
Title |
---|
程志明: "咪唑啉酮类除草剂的工业化合成方法", 《上海化工》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017071414A1 (en) * | 2015-10-29 | 2017-05-04 | Rotam Agrochem International Company Limited | Novel crystalline form of imazapyr, its preparation and use |
GB2554842A (en) * | 2015-10-29 | 2018-04-11 | Rotam Agrochem Int Co Ltd | Novel crystalline form of imazapyr, its preparation and use |
US10077248B2 (en) | 2015-10-29 | 2018-09-18 | Rotam Agrochem International Company Limited | Form of imazapyr, a process for its preparation and use the same |
GB2554842B (en) * | 2015-10-29 | 2021-04-14 | Rotam Agrochem Int Co Ltd | Novel crystalline form of imazapyr, its preparation and use |
CN112142714A (zh) * | 2019-06-27 | 2020-12-29 | 山东润博生物科技有限公司 | 一种灭草烟的合成方法 |
Also Published As
Publication number | Publication date |
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CN102532102B (zh) | 2014-01-08 |
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C06 | Publication | ||
PB01 | Publication | ||
C53 | Correction of patent of invention or patent application | ||
CB02 | Change of applicant information |
Address after: 100192 Beijing city Haidian District West Road No. 66 small Zhongguancun Dongsheng Technology Park building D-1, Northern Territory Applicant after: Nutrichem Co., Ltd. Address before: 100192 Beijing city Haidian District West Road No. 66 small Zhongguancun Dongsheng Technology Park building D-1, Northern Territory Applicant before: Nutrichem International Co., Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: BEIJING NUTRICHEM INTERNATIONAL CO.,LTD. TO: BEIJING NUTRICHEM BIOTECHNOLOGY CO., LTD. |
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C14 | Grant of patent or utility model | ||
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C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 100192 Beijing city Haidian District West Road No. 66 small Zhongguancun Dongsheng Technology Park building D-1, Northern Territory Patentee after: BEIJING NUTRICHEM COMPANY LIMITED Address before: 100192 Beijing city Haidian District West Road No. 66 small Zhongguancun Dongsheng Technology Park building D-1, Northern Territory Patentee before: Nutrichem Co., Ltd. |
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C41 | Transfer of patent application or patent right or utility model | ||
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Effective date of registration: 20160328 Address after: 224600 Jiangsu province Yancheng City Xiangshui Chenjiagang chemical industry zone Patentee after: Yancheng South Chemical Co., Ltd. Address before: 100192 Beijing city Haidian District West Road No. 66 small Zhongguancun Dongsheng Technology Park building D-1, Northern Territory Patentee before: BEIJING NUTRICHEM COMPANY LIMITED |
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Effective date of registration: 20210730 Address after: 310000 No. 9777, Hongshi 5th Road, Hangzhou Xiaoshan Linjiang Industrial Park, Xiaoshan District, Hangzhou, Zhejiang Province Patentee after: HANGZHOU YINGTAI BIOTECHNOLOGY Co.,Ltd. Address before: 224600 Chenjiagang chemical industry zone, Xiangshui County, Yancheng City, Jiangsu Province Patentee before: YANCHENG SOUTH CHEMICALS Co.,Ltd. |