LU84295A1 - Procede de preparation d'acides phenoxybenzoiques - Google Patents
Procede de preparation d'acides phenoxybenzoiques Download PDFInfo
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- LU84295A1 LU84295A1 LU84295A LU84295A LU84295A1 LU 84295 A1 LU84295 A1 LU 84295A1 LU 84295 A LU84295 A LU 84295A LU 84295 A LU84295 A LU 84295A LU 84295 A1 LU84295 A1 LU 84295A1
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- LU
- Luxembourg
- Prior art keywords
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- 239000002253 acid Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000007513 acids Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 150000001721 carbon Chemical class 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000001804 chlorine Chemical class 0.000 claims 2
- 240000008570 Digitaria exilis Species 0.000 claims 1
- 235000019715 Fonio Nutrition 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical group [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 cyclcpentane Chemical compound 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000002515 guano Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical group [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- A01N1/00—Preservation of bodies of humans or animals, or parts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
-
- 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
- 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
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C301/00—Esters of sulfurous acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
- C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
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Description
La présente invention concerne un procécé perfectionné ce préparation ce certains cérivés c'acices phénoxy-benzoïques à croupe sulfcnamic.e ayant ces propriétés herbi-cices.
5 Des cérivés hercicices c'acïres phéncxybenzoioues è groupe sulfonsmioe sont connus es ns les cernantes ce brevets européens 3£it et 23352.
Ces cemances ce brevets civuiguent ces produits ce formule : lu
C ,B R
y-/ _/ 0 Vy s (I)
E ' X F
13 et leurs sels, dans laquelle : A est 1’hycroçère, le fluor, le chlore, le brome, l'ioce, un groupe nitre; -K-NCF, ; PCLH et <ses esters c'sl-
S Z
2C kyle ce 1 à A atomes de carbone ; N FU, NHOH, N* ; un -groupe csrbcxyle ou l'un ce ses cérivés fonctionnels ; un groupe monoou cislkylaminc ; un groupe NH-CD-R·*" dans le- l quel R est ur, radical alkyle ou alkoxyle ou moncslkyls-mino ou cialkyiamino ; un groupe alkyle ; trialkylammonio, 25 NHS0,.Rz où r. est un racical alkyle ou phényle ; L· r r* NHCLkt-.Sü^n , où h*· a la signification céjà indiquée, sikylthio, alkylsulfinyie, alkyisuifenyie, cielkylsul-fonio, cyancsulfonyle, hycroxy, alkanoyloxy, alkoxy, alkoxy substitué pai un slkoxycerbcnyle, SH, nitrcsc, -SCN, szide, 3u CF-., -N=!«-P- ( CCH-. ), scyle ;
Iu· 4, n z
O
c est i ' hycrccèr.e, le fluci, le chlcre, le trcr.e, l'ioce, ou un çrcupe alkyle, aikcxy, alkylsuifinyle, ai- / kylsuifcnyie, C.*·-, LL,,, CL, Nh0, LHCCr.“ eu F- est si/ 35 céfini ccrr.re ci-cessus eu CGNH, ; /j// I ' f 2 C est l'hydrogène ou un halogène ou un groupe al-kyle ou dialkylami.no D est le fluor, le chlore, le brome, l'iode ; ou un groupe CF^, alkylthio, alkylsulfinyle, alkylsulfonyle, 5 halogenoalkyle, sulfamoyle, formyle, alkylcarbonyle, CN ou diméthylamino ; E est l'hydrogène ou un groupe halogenoalkyle, al- koxy, alkylsulfinyle, alkylsulfonyle, CN, CF,, NH0,
Il -5 ^ C0NH2, NH-CO-R , R ayant la signification déjà in- 10 diquée ;
F a l'une des significations données pour B
R est un groupe -C0N(R^)S09R3 dans lequel , 4 x * R est l'hydrogene ou un groupe alkyle de 1 à 4 I atomes de carbone E 3 15 R est un groupe phényle, pyridyle ou thiényle éventuellement substitué par un ou plusieurs atomes d'halogène, ou groupes alkyle, ou groupes nitro ; ou un radical alkényle ou alkynyle ayant 2 à 4 atomes de carbone ou un radical alkyle de 1 à 4 atomes de carbone éventuellement * > 20 substitue par un ou plusieurs atomes de fluor, chlore, brome ou iode, de préférence CF^, ou par un ou plusieurs des substituants suivants : carboxyle, alkoxycarbonyle de 2 à 5 atomes de carbone, alkylcarbonyle de 2 à 5 atomes de „ carbone, mono ou dialkylcarbamoyle dans lequel les groupes 25 alkyle ont de 1 à 4 atomes de carbone, alkylthio, alkylsulfinyle, alkylsulfonyle, chacun ayant de 1 à 4 atomes de carbone, alkylcarbonyloxyle de 2 à 5 atomes de carbone, al-kylcarbonylamino de 2 à 5 atomes de carbone, ou cyano.
Selon les procéoés connus, les produits de formule 30 (I) peuvent être préparés par réaction entre 25 et 140°C
d'un halogènure d'scioe intermédiaire de formule : c_ys> _^COX / d-: fVow fr~A (II) Π/ 35 yJ -V (f E F / » 3 dans laquelle X est le chlore, le brome ou l'iode, et A, B, C, D, E, F ont les significations déjà indiquées, avec un sulfonamide de formule : 5 R3Sû2NH2 (III) où R3 a la signification déjà indiquée, en présence d'un accepteur d'acide, notamment une amine tertiaire telle que la Ni,h-diméthylaniline ou la pyridine, ou un carbonate de métal alcalin tel que le carbonate de potassium anhydre, ou 10 un fluorure de métal alcalin tel que le fluorure de césium.
Les composés de formule (I) dans laquelle R^ est l'atome d'hydrogène peuvent être alkylés de manière connue, par exemple par réaction d'un diazoalcane de 1 à 4 atomes de carbone, de manière à fournir les produits correspon-15 dants dans lesquels est un groupe alkyle de 1 à 4 atomes de carbone.
Ce procédé de condensation des produits de formule (II) et (III) a de nombreux inconvénients : les rendements sont médiocres (par exemple on peut calculer un rendement A 20 de 27% pour l'exemple 14 de la demande de brevet européen 23392 et 9,5 % pour l'exemple 34). On pense aue c'est la présence d'accepteur d'acide qui abaisse le rendement par le fait qu'il favorise la réaction de diacylation. De plus l'utilisation d'un accepteur d'acide rend l'isolement et la 25 purification des produits finaux plus difficile et plus coûteuse.
Un but de l'invention est de remédier à ces incon-! ’ vénients.
i Le procédé selon l'invention comprend la réaction 30 d'un halogènure d'acide (de préférence un chlorure, un bromure ou un iodure) avec un sulfonamide de formule (III) en l'absence d'accepteur d'acioe et à une température à laquelle l'acide halohycriaue (HCl, HBr, ΗΊ) est éliminé sous forme gazeuse du milieu réactionnel au fur et à mesure de 35 sa fcrmaticn mais sans décomposition appréciable ou proouit / de réaction de formule (I). / i/ h
Grâce eu prccécé selon l'invention, oes rendements notablement plus élevés en cérivés sulfonamides c'acides phénoxybenzoiQues peuvent être ootenus, par exemple des rencE-ments c'au moins environ 3UL et fréouemment c'su moins 5 environ 50¾ et avec un mode ce récupération et de purification ou produit final beaucoup plus simple eue ceux des procéüés connus.
Comme halogénure d'acice mis en oeuvre dans l'invention, on utilise en pratioue un halogénure d'acide de lu formule (II) ; ce préférence en utilise un halogénure dans la formule duquel A est le groupe N02 ou un atome de fluor, de chlore, oe brome ou d'iode ; B est un atome d'ha-loçène ; C, E et F sont l'atome d'hydrogène ; D est le groupe CF_.. On préfère également mettre en oeuvre des I -5 3 15 sulfonamioes oe formule (III) dans laauelle R est un groupe alkyle, spécialement CH^, ou un groupe CF_. f . La température à laquelle le procédé oe l'invention peut être mis en oeuvre cépeno notamment de ce que l'halo-génure d'acide de formule (II) ou le sulfonamide de formule 20 (III) sont l'un ou l'autre en large excès ou de ce aue l'on, utilise, ou non, un solvant ayant des propriétés catalytiques.
Ainsi iGrsoue l'halocénure d'acice (II) est en large excès, c'est à dire que le rapport mdaire (11)/(111) 25 est compris entre environ 1,5 et 5, l'halGgénure d'acide (II) peut servir ce solvant pour la réaction et la température oe réaction peut être comprise entre 6G et 200°C, mais elle est alors oe préférence comprise entre 90 et 16GCC.
3u L'halocénure d'acice (II) n'ayant cas réagi peut être récupéré du milieu réactionnel par lavage avec un solvant inerte tel qu'un hydrocarbure, notamment le pentane, l'hexane, l'heptane, le cyclcpentane, le cyclohexane, le cycloneotane, le benzène, le toluène, le xylèr.e, un hydre-35 carbure halogène notamment les chlcrobenzènes, CS^, le _ / tetrahyGrofurar.ne, le dicxsnne et c'autres. /// f- 5
Guano on utilise un excès ce sulfonamice, c’est à aire auanc le rapport mclaire ces composés (111)/(11) est compris entre 1,5 et 5, la température réactionelle est alors généralement comprise entre 9ü et 2Q0°C et de préfé-5 rence comprise entre 140 et 160°C. En tout état de cause elle coit être au moins suffisante pour faire fondre le milieu réactionnel. L'excès ce Sulfonamide (III) peut être récupéré gu milieu réactionnel par lavage à l'eau ou un autre solvant inerte ce ce réactif (III). lu Les réactifs peuvent aussi être clssous dans un solvant inerte ayant un point c'ébullition supérieur à la température ce réaction par exemple un hydrocarbure liquide, chloré ou non tel que le benzène, le toluène, les xylènes, les mélanges oe xylènes, le cumène, auquel cas la 15 température maximale de réaction est avantageusement légèrement inférieure au point c'ébullition du solvant. Ainsi aans le cas ou cumène qui bout à environ 153°C, la réaction est mise en oeuvre ce préférence entre 13ü et 150°C. L'usage d'un solvant inerte a l'avantage pratique de permettre 20 un meilleur transfert de chaleur dans un procédé à l'échel-*, le industrielle ; il permet aussi d'éviter les surchauffes locales eu milieu réactionnel.
Selon une autre variante de l'invention, on utilise , un solvant ayant une action catalytique à l'égard de la 25 réaction entre l'halogénure d'ecice (II) et le sulfonamide (III) pour fournir le phéncxybenzcylsulfonsmice (I). Le diméthylfcrmamice (=UMF ; cui bout à environ 154°C) et le diméthyiacétamioe (= DMAC ; qui oout à environ 164°C) sont particulièrement avantageux c cet écarc et leur usage per-3u met la mise en oeuvre oe température relativement basses par exemple comprises entre 6U et 12ü°C, ce préférence entre 50 et 11G°C eu encore des températures plus élevées, légèrement inférieures aux points c'ébullition de ces solvants ; la vitesse et réaction est alors plus rspice.
35 Les exemples suivants oennes a titre non limitatif , illustrent l'invention et rentrent comment elle neut être / i !' =: 6 1 mise en oeuvre.
Î Exemple I
Gr mélange 2 c (u, C21 rr-clt) ce méthane sulfonsmice avec 3,6 c (u,ul mole) ce chlorure ce l'acide 5- 2'-chlc- ! 5 rc-t ' - (tri f lucrométhyl ) rhéncxy -2-nitrcbenzc-ïcue. On chauffe le mélange 2U minutes à 15G°C. L'acice chlorhy- cricue se cépage eu milieu réactionnel au fur et à mesure de sa formation, ün refroidit ; en a une huile noire αυ'οπ dissout cans ce la scuce soueuse ; on filtre, acidifie le l IG filtrat à l'aide d'hCl dilué, ce qui précipite le produit :j oe formule (IV). Cn a ainsi obtenu, avec un rendement ce 71 i /6, 3,1 g oe procuit fonçant à 195-197°C et ayant une bande -1 i: ‘ d’absorption infrarouge à 1652 cm (croupe C=Q).
• Ce preauit a pour formule : :j 15
Cl CO-NH-SO^-CH., _ · _/ 2 3 GF γ —O— r NO„ (IV) ! \_, _ 2 t:- : 2 u p Exemple 2 f On reprocuit l'exemple I mais en utilisant 250 g oe i| chlorure c'scioe et 13G ç de méthane sulfonamide. Le pro- ! ^ cuit ce réaction est isolé directement après refroidisse- | 25 ment gu mélange par recristillisation Gans 1'iscpropancl.
ün a un rendement ce u 2 (165 c) en produit ce formule (IV). La structure ce ce produit est confirmée par infrarouge (bande o'abserptior à 1692 ern'^) et par résonance magnétïcue nucléaire (sirculet à 3,5 ppr? ; multiplet à c,C7 3G ppm).
I En appiigu&nt re procédé ce l'exemple oe la cernanee
Si ce brevet européen 23352 en utilisant la pyricine comme accepteur d'acice, r£ renrenent n'a été eue ce 25 2 / i S/
Claims (5)
- 7
- 5 REVChuICATIGhS i) - Procécé ce préparation ce dérivés phénoxybenzoïques à groupe sulfcnamice ce formule lü C ,B H \ / y D—/TV 0 \Λ il) / N E F 15 et ses sels, cans laquelle A est l'hyoroçène, le fluor, le chlore, le brome, l'iode, un groupe nitro; -N=NCF^ ; Pü^l-L et ses esters d'al-2G kyle de 1 à 4 atomes de carbone ; NH2, NHGH, N* ; un croupe carbGxyie ou l'un de ses cérivés fonctionnels ; un groupe mono ou dialkylamino ; un groupe NH-CO-R^ cans lequel R^ est un racical alkyle ou alkoxyle ou mcncalkyla- minc ou aialkylaminc ; un groupe alkyle ; trialkylammonio, * 2
- 25 UHSG^R où R^ est ur. racical alkyle ou phényie ; NHüubHSG^r , cl a la signification Géjs inciouée/ alkylthic, aluyisulfinyle, aikyisuifonyle, oislkylsui- fonio, cyanosclfonyle, hycroxy, alkancyicxy, alkoxy, alkoxy suostiiué par _r. aikoyycartcr.\ le, $h, nitrcsc, -SCb·, azioe, 3>u —l\=K-P-(lwη-· ;^ , scyie ; O E est 1'hycroçènt, le fluor, le chlore, le brome, l'îcoe, ou ur croupe alkyle, sikcxy, slkyisulfinyle, ai- / kylsuïf cnyle, ,, î'.Üv, CI», Ni-,.., NhÜCn“ eu r.~ est y~,/ 55 céfini comme ci-cessus ou CONR^ ; /1/ l // / 1 >- C est i'hycrcgène eu un halogène ou un groupe al-kyle ou Gialkylaminc L· est le fluor, le chlore, le crcme, l'iooe ; ou un groupe CF,, aikyithic, slkylsulfinyle, alkylsulfonyle, Î3 rsiccencalkyie, sulfamcyie, fcrrr.yie, slkylcsrbonyle, CK ou ciméthylsmino ; E est l'nycrcçène eu un croupe halccéncai.kyie, sl- koxy, alkylsulfinyle, slkylsulfonyle, CN, CF,, Nh0, 11 % 1 CüNH^, NH-LC-k , R ayant la siçnificeticn oéjà inoi- lu quée ; F a l'une ces significations connées pour B R est un groupe -COk(RA JSCvR"5 oans lequel k est I'hycrcgène ou un croupe alkyie oe 1 à A | atorr.es oe c a roc ne j 13 h' est un groupe pr.ényie, pyridyle eu thiényle ! éventuellement substitué par un ou plusieurs atomes ti'halo- [: gène, ou groupes aiKyle, ou groupes nitre ; ou un racical I alkényle ou alkynyie ayant 1 a u atomes oe carbone ou un racical alkyie ce 1 à A atomes ce carbone éventuellement ! 2U substitué par un ou plusieurs atomes ce fluor, chlore, i brome uu ioce, ce préférence CF,, eu par un ou plusieurs j ces substituants suivants : carboxyle, alkcxycarbonyle oe 2 | à 3 atomes ce carrent, alkyicarbonyle ce 2 s 5 atomes ce j carbcne, m.onc eu cialkylcarbamoyle dans lecuel les groupes i 21 alkyie cm ce 1 à u atomes ce carbone, aikyithic, alkyisul- ! finyie, alkylsulfonyle, chacun ayant ce 1 à A atomes ce j caroone, alkylcaiccryicx\le ce 2 à 3 atomes ce carbone, | _ aikylcarbonylsmino ce 2 à 3 atomes ce carbcne, ou cyano, le : cit prccécé consistant à faire réagir un baJcgérure c'acice i 3u oe formule / I C B COM / i \ / (_/ A4 ; & / t )-û~ f—h di) (j? i 1'/ v F / j " **' j i c. ** cens iacuelle X est un atcrne ce chlore, ce brome eu c’ioce et a, Γ-, u, \j, E, F ent les significations inciouées cens la formule (1), avec un sulfcnam.ice Ge fcrrr.ule h3 SG0 {-.h (iii), r/ ayant également 1b signif icaticr-3 céjà incicuée, le Gît prccécé étant caractérise en ce que la réaction est effectuée en i'acsence c'accepteur a'acide et s une température à laquelle i'hycrscioe gazeux sous-procuit est éliminé eu milieu réactionnel au fur et à mesure ce sa formatier,, cette température étant inférieure à lu la température ce cécompositicn eu procuit ce formule (I). 2) - Procéoe selon la revencication 1 caractérisé en ce qu'en opère en présence c'un excès c'halcçénure c'acioe de formule (II). 3) - Prccécé seien le revendication 2 caractérisé en ce eue 15 le rapport molaire halcçénure c'scice Ge formule (II)/sul- fonamice ce fermuie (III) est compris entre 1,5 et 5 4) - Procédé selon l'une ces revencications 2 ou 3 caractérisé en ce eue la température réactionnelle est comprise entre 6ü et 2ûû°C, ce préférence entre Su et 16Q°C ja. 2ü 5) - Procécé' selon la revencication 1 caractérisé en ce - , au'on opère en présence c'un excès ce sulfonamioe. e) - Procécé selon la revencication 5 caractérisé en ce eue le rapport molaire sulfonamioe oe formule (III)/haicgènure , c'acioe ce formule (II) est compris entre 1,5 et 5 ^3 7) - Procécé selon l'une ces revencications 5 ou C caracté rise en ce eue la température réactionnelle est comprise entre Sü et 2U0°C, ce préférence entre iau et i£ü°C. b) - Prccécé seien ;'une ces revencicaticns 1 à 7 caractérisé en ce cLt i'cr cqère en présence c'ur solvant ayant cr ^ peint c'ébuliitiPT. supérieur à la température réactionnelle. 5) - Procécé selon la revencicaticn 6 caractérisé en ce eue le solvant est un n\ crccarcure. iu) - Prccécé sels” i£ revencication 9 caractérisé en ce que _e st-’.arc est *e cl·”tre et eue la température est cc~- J 35 prise entre et i5oDt. /y if i i i i i s i u £ 1-0 - Prccécé selon l'une ces revencicetions 1 a 8 caracté- E risé en ce eu'on opère en présence c'ur, solvant ayant aes propriétés cstalyticues ε l'éparc ce le réecticn. 12) - Prccécé selon la revencicaticn II caractérisé en ce 3 eue le solvant est le cin.éthylforrr.amice ou le diméthylacé- tamice et eue la température est comprise entre êü°C et la température c ' étulliticn eu servant. 13) - nrccécé selon la revencication 12 caractérisé en ce que la température est supérieure a fu0L. I iu 14) - Procécé selon l'une ces revencications 1 è 13 carac- I térisé en ce eue, caris les fcrrrules (I) et (II), B et X Isont l'atome ce chlore, A est l'atcme Ge chlore ou NO„. 2’
- 5 L, ii, F sont l'atcme c'hycroçène, L est CF^. S 15) - Prccécé selon i'ure ces revencications 6 eu 7 carac- 15 térisé en ce eue le suifcnar.ice est tel eue h-5 est un 1 croupe slkyie ou UF_, ce préférence méthyle. Ί W O '! 16) - Procécé selon I'ure ces levencicaticns 1 à 15 carac- iij térisé en ce eue l'on effectue la réaction entre $
- 1 Cl CO-C1 1 ._/ _/ Icf3 —y r o— t y N02 Dessins :.............pianenes pages dont .....Ol....... page de garde __________é.......pages de description * __________H....... pages de revendications % ________abrégé descriptif J Luxembourg, le Z6 jy|i4982 J Lem^^ataire : i' Charles München i f i* [. i
Applications Claiming Priority (2)
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US28693881A | 1981-07-27 | 1981-07-27 | |
US28693881 | 1981-07-27 |
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LU84295A LU84295A1 (fr) | 1981-07-27 | 1982-07-26 | Procede de preparation d'acides phenoxybenzoiques |
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JP (1) | JPS5826860A (fr) |
KR (1) | KR880002591B1 (fr) |
AT (1) | AT385985B (fr) |
BE (1) | BE893940A (fr) |
BR (1) | BR8204357A (fr) |
CA (1) | CA1194472A (fr) |
CH (1) | CH652384A5 (fr) |
DD (1) | DD203716A5 (fr) |
DE (1) | DE3227847A1 (fr) |
DK (1) | DK333282A (fr) |
ES (1) | ES8306108A1 (fr) |
FR (1) | FR2510105A1 (fr) |
GB (1) | GB2103611B (fr) |
HU (1) | HU191186B (fr) |
IE (1) | IE53978B1 (fr) |
IL (1) | IL66197A (fr) |
IT (1) | IT1198399B (fr) |
LU (1) | LU84295A1 (fr) |
NL (1) | NL8202994A (fr) |
PL (1) | PL136683B1 (fr) |
PT (1) | PT75322B (fr) |
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GB8628109D0 (en) * | 1986-11-25 | 1986-12-31 | Ici Plc | Chemical process |
US11834714B2 (en) | 2021-12-20 | 2023-12-05 | Enumerix, Inc. | Detection and digital quantitation of multiple targets |
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DE2960664D1 (en) * | 1978-01-19 | 1981-11-19 | Ici Plc | Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them |
DE3068101D1 (en) * | 1979-07-18 | 1984-07-12 | Ici Plc | Diphenyl ether compounds, and herbicidal compositions and processes utilising them |
-
1982
- 1982-06-25 FR FR8211332A patent/FR2510105A1/fr active Granted
- 1982-07-01 IL IL66197A patent/IL66197A/xx unknown
- 1982-07-20 DD DD82241801A patent/DD203716A5/de unknown
- 1982-07-23 IT IT22545/82A patent/IT1198399B/it active
- 1982-07-23 PL PL1982237639A patent/PL136683B1/pl unknown
- 1982-07-23 CH CH4523/82A patent/CH652384A5/fr not_active IP Right Cessation
- 1982-07-26 BR BR8204357A patent/BR8204357A/pt unknown
- 1982-07-26 IE IE1786/82A patent/IE53978B1/en unknown
- 1982-07-26 CA CA000408056A patent/CA1194472A/fr not_active Expired
- 1982-07-26 BE BE0/208676A patent/BE893940A/fr not_active IP Right Cessation
- 1982-07-26 NL NL8202994A patent/NL8202994A/nl not_active Application Discontinuation
- 1982-07-26 GB GB08221574A patent/GB2103611B/en not_active Expired
- 1982-07-26 ES ES514352A patent/ES8306108A1/es not_active Expired
- 1982-07-26 DK DK333282A patent/DK333282A/da not_active Application Discontinuation
- 1982-07-26 HU HU822401A patent/HU191186B/hu not_active IP Right Cessation
- 1982-07-26 JP JP57130216A patent/JPS5826860A/ja active Granted
- 1982-07-26 DE DE19823227847 patent/DE3227847A1/de not_active Withdrawn
- 1982-07-26 SU SU823467843A patent/SU1215620A3/ru active
- 1982-07-26 LU LU84295A patent/LU84295A1/fr unknown
- 1982-07-26 PT PT75322A patent/PT75322B/fr unknown
- 1982-07-27 AT AT0290082A patent/AT385985B/de not_active IP Right Cessation
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- 1982-07-27 KR KR8203344A patent/KR880002591B1/ko active
Also Published As
Publication number | Publication date |
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RO85388B (ro) | 1984-11-30 |
IL66197A0 (en) | 1982-11-30 |
FR2510105A1 (fr) | 1983-01-28 |
DD203716A5 (de) | 1983-11-02 |
KR880002591B1 (ko) | 1988-12-03 |
GB2103611B (en) | 1985-04-03 |
CH652384A5 (fr) | 1985-11-15 |
PL136683B1 (en) | 1986-03-31 |
IL66197A (en) | 1985-11-29 |
IE53978B1 (en) | 1989-05-10 |
DK333282A (da) | 1983-01-28 |
HU191186B (en) | 1987-01-28 |
DE3227847A1 (de) | 1983-02-10 |
ATA290082A (de) | 1987-11-15 |
GB2103611A (en) | 1983-02-23 |
IT8222545A0 (it) | 1982-07-23 |
BR8204357A (pt) | 1983-07-19 |
IT8222545A1 (it) | 1984-01-23 |
BE893940A (fr) | 1983-01-26 |
JPH0149262B2 (fr) | 1989-10-24 |
PT75322B (fr) | 1985-11-29 |
JPS5826860A (ja) | 1983-02-17 |
ES514352A0 (es) | 1983-05-01 |
SU1215620A3 (ru) | 1986-02-28 |
FR2510105B1 (fr) | 1984-09-07 |
KR840000466A (ko) | 1984-02-22 |
AT385985B (de) | 1988-06-10 |
PL237639A1 (en) | 1983-05-23 |
CA1194472A (fr) | 1985-10-01 |
PT75322A (fr) | 1982-08-01 |
IE821786L (en) | 1983-01-27 |
IT1198399B (it) | 1988-12-21 |
ES8306108A1 (es) | 1983-05-01 |
NL8202994A (nl) | 1983-02-16 |
RO85388A (fr) | 1984-11-25 |
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