RU2016120999A - Способ приготовления солей карбоновой кислоты, обладающих гербицидным действием - Google Patents
Способ приготовления солей карбоновой кислоты, обладающих гербицидным действием Download PDFInfo
- Publication number
- RU2016120999A RU2016120999A RU2016120999A RU2016120999A RU2016120999A RU 2016120999 A RU2016120999 A RU 2016120999A RU 2016120999 A RU2016120999 A RU 2016120999A RU 2016120999 A RU2016120999 A RU 2016120999A RU 2016120999 A RU2016120999 A RU 2016120999A
- Authority
- RU
- Russia
- Prior art keywords
- carboxylic acid
- base
- solvent
- dicamba
- alkali metal
- Prior art date
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- 238000000034 method Methods 0.000 title claims 24
- 150000004649 carbonic acid derivatives Chemical class 0.000 title 1
- 230000002363 herbicidal effect Effects 0.000 title 1
- 239000002585 base Substances 0.000 claims 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 10
- 239000002904 solvent Substances 0.000 claims 9
- 238000009835 boiling Methods 0.000 claims 5
- HLZCHRAMVPCKDU-UHFFFAOYSA-M dicamba-sodium Chemical compound [Na+].COC1=C(Cl)C=CC(Cl)=C1C([O-])=O HLZCHRAMVPCKDU-UHFFFAOYSA-M 0.000 claims 5
- 239000005504 Dicamba Substances 0.000 claims 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000000725 suspension Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- -1 alkali metal hydrogen carbonates Chemical class 0.000 claims 3
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000005500 Clopyralid Substances 0.000 claims 1
- 239000005574 MCPA Substances 0.000 claims 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000005595 Picloram Substances 0.000 claims 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000001559 benzoic acids Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
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- C07C51/41—Preparation of salts of carboxylic acids
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (32)
1. Способ приготовления гербицидно активной соли карбоновой кислоты, который включает стадии:
i) объединения карбоновой кислоты с высококипящим, не смешивающимся с водой органическим растворителем для получения раствора или суспензии;
ii) обработки полученного на стадии (i) раствора или суспензии основанием для образования соли карбоновой кислоты;
iii) удаления растворителя из полученной на стадии (ii) смеси для получения кека соли карбоновой кислоты; и
iv) высушивания полученного на стадии (iii) кека.
2. Способ по п. 1, в котором карбоновую кислоту выбирают из бензойных кислот, феноксикарбоновых кислот, пиридинкарбоновых кислот и хинолинкарбоновых кислот.
3. Способ по п. 2, в котором карбоновую кислоту выбирают из группы, состоящей из дикамбы, трикамбы, 2,4-D, МСРА, пиклорама, клопиралида и хинклорака.
4. Способ по п. 3, в котором карбоновая кислота представляет собой дикамбу.
5. Способ по любому из пп. 1-4, в котором растворитель имеет низкую или, по существу, отсутствующую склонность к сольватации соли карбоновой кислоты.
6. Способ по п. 1, в котором карбоновая кислота является растворимой в растворителе.
7. Способ по п. 1, в котором растворитель имеет точку кипения по меньшей мере 70°C.
8. Способ по п. 1, в котором растворитель выбирают из толуола, ксилола, н-бутанола, пентанолов, гексанолов, гептанолов и их смесей.
9. Способ по п. 1, в котором растворитель образует азеотроп с водой.
10. Способ по п. 9, в котором на стадии (iii) растворитель удаляют вместе с водой во время протекания реакции между карбоновой кислотой и основанием на стадии (ii).
11. Способ по п. 10, в котором растворитель и воду удаляют азеотропной перегонкой.
12. Способ по любому из пп. 9-11, в котором точка кипения азеотропа ниже температуры реакции стадии (ii).
13. Способ по любому из пп. 9-11, в котором точка кипения азеотропа близка или, по существу, является такой же, как и температура реакции стадии (ii).
14. Способ по п. 1, в котором основание является неорганическим основанием.
15. Способ по п. 14, в котором основание является соединением металла группы I или группы II или соединением аммония.
16. Способ по п. 15, в котором основание выбирают из гидроксидов щелочных металлов, оксидов щелочных металлов, карбонатов щелочных металлов, гидрокарбонатов щелочных металлов, ацетатов щелочных металлов, формиатов щелочных металлов и аммиака.
17. Способ по п. 1, в котором основание является органическим основанием.
18. Способ по п. 17, в котором основание является алкилзамещенным первичным, вторичным и третичным амином, имеющим от 1 до 4 атомов углерода.
19. Способ по п. 1, в котором основание подают на стадии (ii) в виде водной смеси или раствора.
20. Способ по п. 1, в котором реакцию на стадии (ii) проводят при температуре от 50 до 200°C.
21. Способ по п. 1, в котором на стадии (ii) обеспечивают от 97 до 100% стехиометрического количества основания, требующегося для реакции с карбоновой кислотой.
22. Способ по п. 1, в котором растворитель удаляют на стадии (iii) центрифугированием.
23. Способ изготовления дикамба-натрия, включающей стадии:
(1) растворения карбоновой кислоты, состоящей, по существу, из дикамбы, в высококипящем, не смешивающемся с водой инертном органическом растворителе для получения раствора или суспензии;
(2) обработки раствора или суспензии дикамбы со стадии (1) основанием, выбранным из гидроксида натрия, бикарбоната натрия и их смесей, в мольном соотношении 1:0,97±0,6% для образования дикамба-натрия;
(3) центрифугирования реакционной смеси со стадии (2) для получения кека соли дикамба-натрия; и
(4) высушивания кека дикамба-натрия, приготовленного на стадии (3), для получения сухого дикамба-натрия, устойчиво демонстрирующего при растворении в воде показатель рН между около 7 и 10.
24. Гербицидно активная соль карбоновой кислоты, приготовленная способом по любому из пп. 1-22.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1319166.3 | 2013-10-30 | ||
| GB1319166.3A GB2519787B (en) | 2013-10-30 | 2013-10-30 | Process for the preparation of herbicidal carboxylic acid salts |
| PCT/CN2014/080265 WO2015062286A1 (en) | 2013-10-30 | 2014-06-19 | Process for preparation of herbicidal carboxylic acid salts |
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| Publication Number | Publication Date |
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| RU2016120999A true RU2016120999A (ru) | 2017-12-05 |
| RU2016120999A3 RU2016120999A3 (ru) | 2018-04-28 |
| RU2664642C2 RU2664642C2 (ru) | 2018-08-21 |
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| RU2016120999A RU2664642C2 (ru) | 2013-10-30 | 2014-06-19 | Способ приготовления солей карбоновой кислоты, обладающих гербицидным действием |
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| Country | Link |
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| US (1) | US10011552B2 (ru) |
| EP (1) | EP3063120A4 (ru) |
| CN (1) | CN105705481B (ru) |
| AR (1) | AR096917A1 (ru) |
| BR (1) | BR112016009593B1 (ru) |
| FR (1) | FR3012290B1 (ru) |
| GB (1) | GB2519787B (ru) |
| MA (1) | MA38997A1 (ru) |
| RU (1) | RU2664642C2 (ru) |
| TW (1) | TWI695826B (ru) |
| UA (1) | UA119447C2 (ru) |
| WO (1) | WO2015062286A1 (ru) |
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| NL2017545B1 (en) * | 2016-09-28 | 2018-04-06 | Eucaryo Beheer B V | Composition comprising a bioactive molecule |
| US12215074B2 (en) | 2019-06-12 | 2025-02-04 | Nouryon Chemicals International B.V. | Process for the production of peroxyesters |
| ES2961184T3 (es) | 2019-06-12 | 2024-03-08 | Nouryon Chemicals Int Bv | Proceso para la producción de peróxidos de diacilo |
| EP3983370B1 (en) | 2019-06-12 | 2023-08-02 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| CN113924282B (zh) * | 2019-06-12 | 2023-09-12 | 诺力昂化学品国际有限公司 | 用于从含水侧流中分离羧酸的方法 |
| EP3983368B1 (en) | 2019-06-12 | 2023-08-02 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| CN111548264A (zh) * | 2020-04-10 | 2020-08-18 | 岳晟 | 一种除草剂二甲胺盐及其制备方法 |
| CN114478234B (zh) * | 2022-02-09 | 2023-03-31 | 河北海力恒远新材料股份有限公司 | 一种4-氯代邻苯二甲酸单钠盐粗品的精制方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB780642A (en) | 1954-12-28 | 1957-08-07 | Bataafsche Petroleum | Process for preparing basic polyvalent metal salts of organic acids |
| US3013054A (en) * | 1958-08-04 | 1961-12-12 | Velsicol Chemical Corp | 2-methoxy-3, 6-dichlorobenzoates |
| GB1011506A (en) * | 1963-10-08 | 1965-12-01 | Distillers Co Yeast Ltd | Salts of carboxylic acids |
| GB1301197A (en) * | 1970-03-17 | 1972-12-29 | Spolana Nat Corp | A method of preparing amine salts of 2.4-dichlorophenoxyacetic acid |
| US4022610A (en) * | 1973-10-15 | 1977-05-10 | Velsicol Chemical Corporation | Herbicidal mixed salts of magnesium |
| FR2588863B1 (fr) | 1985-10-18 | 1987-12-11 | Rhone Poulenc Spec Chim | Procede de preparation de sels alcalins de l'acide trifluoroacetique a l'etat anhydre et cristallise |
| US5266553A (en) * | 1991-10-21 | 1993-11-30 | Riverdale Chemical Company | Method of manufacturing a dry water-soluble herbicidal salt composition |
| US5336806A (en) | 1993-09-20 | 1994-08-09 | Occidental Chemical Corporation | Purification of 2,4,5-trifluorobenzoic acid |
| DE4446387A1 (de) * | 1994-12-23 | 1996-06-27 | Basf Ag | Verfahren zur Herstellung fester, freifließender wasserlöslicher Salze von Aryloxi-C¶1¶-C¶4¶-alkancarbonsäuren |
| RO115685B1 (ro) * | 1996-07-25 | 2000-05-30 | Sc Oltchim Sa | Procedeu de obtinere a unor saruri erbicide, solide, anhidre, solubile in apa |
| GB0017617D0 (en) | 2000-07-18 | 2000-09-06 | Zeneca Ltd | Chemical process |
| CN1165541C (zh) | 2000-08-31 | 2004-09-08 | 浙江新安化工集团股份有限公司 | 草甘膦酸铵合成工艺 |
| US6410783B1 (en) * | 2000-10-19 | 2002-06-25 | Basf Corporation | Method of producing carboxylic acid salts |
| JP2004161640A (ja) | 2002-11-11 | 2004-06-10 | Nippon Jiyouriyuu Kogyo Kk | アクリル酸亜鉛およびその製造方法 |
| CN103025701B (zh) | 2010-05-17 | 2016-01-20 | 澳大利亚纽法姆有限公司 | 除草性盐的制备方法 |
-
2013
- 2013-10-30 GB GB1319166.3A patent/GB2519787B/en not_active Expired - Fee Related
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2014
- 2014-06-19 BR BR112016009593-6A patent/BR112016009593B1/pt not_active IP Right Cessation
- 2014-06-19 MA MA38997A patent/MA38997A1/fr unknown
- 2014-06-19 EP EP14859233.0A patent/EP3063120A4/en not_active Ceased
- 2014-06-19 RU RU2016120999A patent/RU2664642C2/ru active
- 2014-06-19 US US15/032,298 patent/US10011552B2/en active Active
- 2014-06-19 WO PCT/CN2014/080265 patent/WO2015062286A1/en not_active Ceased
- 2014-06-19 CN CN201480060871.0A patent/CN105705481B/zh not_active Expired - Fee Related
- 2014-06-19 UA UAA201604712A patent/UA119447C2/uk unknown
- 2014-07-15 AR ARP140102604A patent/AR096917A1/es unknown
- 2014-07-28 FR FR1457298A patent/FR3012290B1/fr not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| CN105705481A (zh) | 2016-06-22 |
| EP3063120A4 (en) | 2017-07-05 |
| EP3063120A1 (en) | 2016-09-07 |
| UA119447C2 (uk) | 2019-06-25 |
| TWI695826B (zh) | 2020-06-11 |
| WO2015062286A1 (en) | 2015-05-07 |
| GB2519787B (en) | 2018-08-29 |
| US10011552B2 (en) | 2018-07-03 |
| FR3012290A1 (fr) | 2015-05-01 |
| MA38997A1 (fr) | 2019-03-29 |
| RU2664642C2 (ru) | 2018-08-21 |
| FR3012290B1 (fr) | 2018-03-23 |
| BR112016009593B1 (pt) | 2020-12-15 |
| GB2519787A (en) | 2015-05-06 |
| RU2016120999A3 (ru) | 2018-04-28 |
| CN105705481B (zh) | 2018-08-31 |
| AR096917A1 (es) | 2016-02-03 |
| TW201516028A (zh) | 2015-05-01 |
| US20160251295A1 (en) | 2016-09-01 |
| GB201319166D0 (en) | 2013-12-11 |
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