EP0906264A1 - Verfahren zur herstellung von alkalimetallsalzen und erdalkalimetallsalzen von aryloxy-c1-c4-alkancarbonsäuren - Google Patents

Verfahren zur herstellung von alkalimetallsalzen und erdalkalimetallsalzen von aryloxy-c1-c4-alkancarbonsäuren

Info

Publication number
EP0906264A1
EP0906264A1 EP97925047A EP97925047A EP0906264A1 EP 0906264 A1 EP0906264 A1 EP 0906264A1 EP 97925047 A EP97925047 A EP 97925047A EP 97925047 A EP97925047 A EP 97925047A EP 0906264 A1 EP0906264 A1 EP 0906264A1
Authority
EP
European Patent Office
Prior art keywords
aryloxy
alkali metal
alkaline earth
metal salts
earth metal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97925047A
Other languages
German (de)
English (en)
French (fr)
Inventor
Hans Rupert Merkle
Erich Fretschner
Jürgen Hofmann
Karl-Friedrich Jäger
Ralph Diener
Axel Paul HÄRTL
Michael SCHÖNHERR
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0906264A1 publication Critical patent/EP0906264A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids

Definitions

  • the present invention relates to a process for the preparation of alkali metal salts and alkaline earth metal salts of aryloxy-C 1 -C 4 -alkanecarboxylic acids by reacting the underlying aryloxy-C 1 -C 4 -alkanecarboxylic acids with alkali metal bases or alkaline earth metal bases in the melt.
  • the invention further relates to the salts obtainable by this process and to the use of those salts which contain a herbicidal crop protection active substance as aryloxy-C 1 -C 4 -alkanecarboxylic acid for combating undesired plant growth
  • a process is known from EP-A 238 240 in which the acidic form of crop protection active ingredients is continuously reacted with a Bronste ⁇ base in an extruder to form salts of the active ingredients.
  • Suitable bases are alkali metal hydroxides, alkaline earth metal hydroxides, ammonia and amines
  • the present invention was therefore based on a process for the preparation of alkali metal salts and alkaline earth metal salts of aryloxy-Ci C 4 alkane carboxylic acids, which leads to products which do not have these disadvantageous properties
  • a process for the preparation of alkali metal salts and alkaline earth metal salts of aryloxy Ci C 4 alkane carboxylic acid by reacting the underlying 1-1 aryloxy Ci C 4 alkane carbon acid with Al ⁇ a ⁇ metallbasen or ⁇ er Er ⁇ alkal_.metalxDasen in the Found melt, which is characterized in that a mixture of the aryloxy-Ci-C 4 -alkanecarboxylic acid and a at least stoichiometric amount of an alkali metal base or an alkaline earth metal base, which are partially or completely converted to volatile substances under the reaction conditions, extruded.
  • salts obtainable by this process and the use of those salts which contain a herbicidal crop protection active substance as aryloxy-C 1 -C 4 -alkane-carboxylic acid have been found to combat undesirable plant growth.
  • Aryloxy-Ca-C 4 -carboxylic acids which are preferred are those having an action against undesired plant growth, IUPAC name and common name, cf. "The Pesticide Manual", The British Crop Protection Council, 9th Edition, London, 1991), for example: (RS) -2- (2, 4-dichlorophenoxy) propionic acid (dichloroprop), R-2- (2, 4 -Dichlorophenoxy) propionic acid (dichloroprop-P, D-2,4-DP), 2,4-dichlorophenoxyacetic acid (2,4-D), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB) , 4- (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid (MCPB) and (R) -2- (4-chloro-o-tolyloxy) propionic acid (Mecoprop-P, D-CMPP).
  • D-2,4-DP, MCPA and in particular D-CMPP can preferably be converted into extrudates of their alkali metal or alkaline earth metal salts by the process according to the invention.
  • Granules which have been produced from hygroscopic aryloxy-C ⁇ -C 4 -alkanecarboxylic acids, for example mecoprop-P, using the process according to the invention have particularly advantageous handling properties.
  • Mixtures of two or three aryloxy-C 1 -C 4 -carboxylic acids can also be used, for example: dichloroprop-P and 2,4-D; Dichlorprop-P and MCPA; Mecoprop-P and 2,4-D; Mecoprop-P and MCPA; MCPA and 2,4-D; Mecoprop-P, Dichlorprop-P and MCPA.
  • alkali metal bases and alkaline earth metal bases which are partially or completely converted to volatile substances under the reaction conditions are acetates which, when reacted, acetic acid and formates which provide formic acid and, above all, carbonates and hydrogen carbonates (formation of carbon dioxide).
  • alkaline earth metals and in particular of alkali metals such as sodium acetate, potassium acetate, sodium formate, potassium formate, preferably sodium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, very particularly preferably potassium carbonate.
  • Al potassium metal bases Mixtures of the abovementioned Al potassium metal bases and alkaline earth metal bases are also suitable.
  • the bases according to the invention are used at least in a stoichiometric amount, preferably in excess, and above all in an excess of 1 to 40 and very particularly preferably 2 to 30 mol%, based on the aryloxy-C 1 -C 4 -carboxylic acids.
  • Volatile substances such as water, carbon dioxide, acetic acid etc. contained in the starting materials and / or formed during the reaction generally escape from the product during the reaction or, if the product leaves the extruder at a sufficiently high temperature, also after that.
  • the reaction in the extruder can take place in the presence of an entrainer which assists in the evaporation of the water escaping.
  • Suitable entraining agents are cyclohexane, toluene and petroleum ether.
  • Low molecular weight alcohols are preferred, in particular Ci-C 7 alkanols and C ⁇ -C 7 alkanediols.
  • Primary, secondary and tertiary alcohols such as methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert are particularly preferred.
  • -B-.tanol pentanols, hexanols, heptanols and mixtures thereof.
  • the molten aryloxy-C 1 -C 4 -alkanecarboxylic acid is reacted in the extruder by intimate mixing with the solid base according to the invention.
  • the solid aryl-C 4 -C 4 -alkanecarboxylic acid is added to the extruder, where it is melted and reacted with the solid base according to the invention.
  • the bases according to the invention can also be used dissolved or suspended in the entrainer.
  • Solid starting materials can be made into a paste as such or in a solvent- ⁇ 5 tel dissolved or suspended the extruder are fed.
  • the solvents are to be selected in such a way that their largely volatilization is ensured during the production of the extrudates according to the invention.
  • one or more of the above 20 entraining agents are used as the solvent.
  • all starting materials can be premixed before the reaction.
  • a premixing of liquid and solid products for example
  • pouring aids or antiblocking agents e.g. Calcium carbonate, tricalcium phosphate, colloidal silica gel and talc are used.
  • mechanical aids such as vibrators and stirrers can be used when handling the premix.
  • extruder is not important in the method according to the invention.
  • Single-screw machines, counter-rotating and intermeshing screw machines and multi-shaft extruders are suitable. These devices are familiar to the person skilled in the art and therefore do not require any further explanation (cf., for example, EP-A 238 240).
  • Preferred extruders in the process according to the invention are 45 co-rotating, intermeshing twin-screw machines.
  • the extruder is advantageously merged with nitrogen or carbon dioxide before the reaction.
  • the reaction is often completed after less than 3 minutes of the reaction mixture in the reaction zone of the extruder.
  • the reaction in the extruder and the subsequent drying of the extrudate can be carried out under normal pressure, under or overpressure at and temperatures from 0 to 250, in particular from 80 DIS 150 ° C.
  • the product is obtained in the form of particles or as a plastic mass, depending on the control of the reaction temperature, which can be shaped in a manner known per se.
  • the procedure is preferably such that particles with a mean diameter of 0.1 to 5, preferably 0.1 to 3 cm are obtained
  • the extrudates produced according to the invention can, to the extent that volatile substances still adhere to them, can be freed from them by conventional (drying) processes.
  • extrudates produced by the process according to the invention which are based on a herbicidal crop protection active ingredient from the chemical class of aryloxy Cx-C 4 -carboxylic acid, are used in the control of undesired plant growth.
  • the method according to the invention is particularly suitable for the preparation of comparatively large particles of aryloxy C 4 -C 4 a -car carboxylic acids Manufacturing examples
  • D + L stands for the total D- + L isomer content of the respective compound.
  • D: L denotes the ratio of these isomers.
  • Zone 1 was cooled with water (temperature of the running water: 38 ° C).
  • Zone 2 was operated at 80 ° C for the entire test period, zones 3 and 4 at 138 ° C.
  • Zone 4 was also open at the top so that volatile substances and water vapor formed during the reaction could outgas.
  • Zones 5, 6, 7 and 8 were cooled with water, with cooling water outlet temperatures of 28 (zone 5), 21 (zone 6), 21 (zone 7) and 20 ° C. (zone 8).
  • the active substance contents of the products were dependent, inter alia, on the quality of the aryl-C 4 -C 4 -alkanecarboxylic acids used, the base amounts and the residual water content.
  • the rubble weight after tamping (method CIPAC MT 169) was 614 g / 1.
  • the water content was 2.6% by weight.
  • the grain size of the water-soluble granules was between 0.25 cm and 2 cm.
  • the product was almost dust-free. When water was put in at 20 ° C, it was immediately wetted completely. With stirring, the product completely dissolved in water into a solution with 1% by weight of active ingredient within 2 minutes (method CIPAC MT 174).
  • the water-soluble granules were ground to prepare a comparison sample, and after sieving, the sieve fraction ⁇ 0.02 mm (powder) was used for testing.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP97925047A 1996-06-20 1997-06-05 Verfahren zur herstellung von alkalimetallsalzen und erdalkalimetallsalzen von aryloxy-c1-c4-alkancarbonsäuren Withdrawn EP0906264A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19624608 1996-06-20
DE19624608 1996-06-20
PCT/EP1997/002914 WO1997048670A1 (de) 1996-06-20 1997-06-05 Verfahren zur herstellung von alkalimetallsalzen und erdalkalimetallsalzen von aryloxy-c1-c4-alkancarbonsäuren

Publications (1)

Publication Number Publication Date
EP0906264A1 true EP0906264A1 (de) 1999-04-07

Family

ID=7797476

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97925047A Withdrawn EP0906264A1 (de) 1996-06-20 1997-06-05 Verfahren zur herstellung von alkalimetallsalzen und erdalkalimetallsalzen von aryloxy-c1-c4-alkancarbonsäuren

Country Status (10)

Country Link
EP (1) EP0906264A1 (cs)
JP (1) JP2000515126A (cs)
KR (1) KR20000022046A (cs)
AR (1) AR007408A1 (cs)
AU (1) AU3032497A (cs)
CA (1) CA2257854A1 (cs)
CZ (1) CZ420298A3 (cs)
EA (1) EA199900023A1 (cs)
TW (1) TW341497B (cs)
WO (1) WO1997048670A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410783B1 (en) * 2000-10-19 2002-06-25 Basf Corporation Method of producing carboxylic acid salts
JP2023043669A (ja) * 2021-09-16 2023-03-29 三菱瓦斯化学株式会社 非炭酸塩の製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1074093A (en) * 1963-03-01 1967-06-28 Unilever Ltd Improvements in or relating to the manufacture of dry metallic soaps
DE2847457C2 (de) * 1978-11-02 1990-05-31 Fried. Krupp Gmbh, 4300 Essen Verfahren zur Herstellung von Alkalisalzen der Fettsäuren in kontinuierlicher Arbeitsweise
DE3728811A1 (de) * 1987-08-28 1989-03-09 Henkel Kgaa Verfahren zur kontinuierlichen herstellung von fettsaeureseifen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9748670A1 *

Also Published As

Publication number Publication date
KR20000022046A (ko) 2000-04-25
TW341497B (en) 1998-10-01
WO1997048670A1 (de) 1997-12-24
AR007408A1 (es) 1999-10-27
JP2000515126A (ja) 2000-11-14
CA2257854A1 (en) 1997-12-24
CZ420298A3 (cs) 1999-03-17
EA199900023A1 (ru) 1999-06-24
AU3032497A (en) 1998-01-07

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