KR100727279B1 - 할로겐화 4-아미노피콜린산의 선택적 전기화학적 환원 방법 - Google Patents
할로겐화 4-아미노피콜린산의 선택적 전기화학적 환원 방법 Download PDFInfo
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- KR100727279B1 KR100727279B1 KR1020027009048A KR20027009048A KR100727279B1 KR 100727279 B1 KR100727279 B1 KR 100727279B1 KR 1020027009048 A KR1020027009048 A KR 1020027009048A KR 20027009048 A KR20027009048 A KR 20027009048A KR 100727279 B1 KR100727279 B1 KR 100727279B1
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- JRZBTJVSAANBEV-UHFFFAOYSA-N 4-aminopyridine-2-carboxylic acid Chemical class NC1=CC=NC(C(O)=O)=C1 JRZBTJVSAANBEV-UHFFFAOYSA-N 0.000 title abstract description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- 229910052709 silver Inorganic materials 0.000 claims description 18
- 239000004332 silver Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003518 caustics Substances 0.000 claims description 4
- 238000002048 anodisation reaction Methods 0.000 claims description 3
- 230000010287 polarization Effects 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229940081066 picolinic acid Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000005868 electrolysis reaction Methods 0.000 abstract description 15
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 16
- 239000003792 electrolyte Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- -1 for example Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003378 silver Chemical class 0.000 description 3
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WRJXSSVEFKALHX-UHFFFAOYSA-N 4-amino-3,6-dibromopyridine-2-carboxylic acid Chemical compound NC1=CC(Br)=NC(C(O)=O)=C1Br WRJXSSVEFKALHX-UHFFFAOYSA-N 0.000 description 2
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 238000007743 anodising Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DLOOKZXVYJHDIY-UHFFFAOYSA-N 2,3,4,5-tetrachloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1Cl DLOOKZXVYJHDIY-UHFFFAOYSA-N 0.000 description 1
- CNLIIAKAAMFCJG-UHFFFAOYSA-N 2,3,5-trichloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1 CNLIIAKAAMFCJG-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical class N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- GXFRQLQUKBSYQL-UHFFFAOYSA-N 3,4,5,6-tetrachloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(Cl)=C(Cl)C(Cl)=C1Cl GXFRQLQUKBSYQL-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000005595 Picloram Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000002001 electrolyte material Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UZOHFGRJSNVQNA-UHFFFAOYSA-N methyl 4-amino-3,5,6-tribromopyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=C(Br)C(N)=C1Br UZOHFGRJSNVQNA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- IHOBBYHEOBWAPZ-UHFFFAOYSA-L steroid c Chemical compound [Na+].[Na+].C1CC2CC(OS([O-])(=O)=O)C(OS([O-])(=O)=O)CC2(C)C(CCC23C)C1C3CC(O1)C2C2(C)OC1OC2CC(C(C)C)=C(C)C IHOBBYHEOBWAPZ-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims (9)
- Ag/AgCl(3.0M Cl-) 기준 전극에 대한 캐소드 전위 -0.4 내지 -1.7V에서 화학식 II의 4-아미노-3,5-디할로피콜린산의 용액을 통해 아노드로부터 캐소드로 직류 또는 교류 전류를 통과시키고, 생성물을 회수함을 포함하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.화학식 I화학식 II위의 화학식 I 및 II에서,X는 화학식 I에 대해서는 Cl 또는 Br이고, 화학식 II에 대해서는 두 개의 X가 동시에 Cl이거나 Br이고,Y는 H, F, Cl, Br 또는 C1-C4 알킬이고,R은 독립적으로 H 또는 C1-C4 알킬이고,단, 화학식 I에서, X가 Cl이면 Y는 Br이 아니다.
- 제1항 또는 제2항에 있어서, 4-아미노-3,5-디할로피콜린산의 용액이 염기성 수용액임을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
- 제1항 또는 제2항에 있어서, X가 Cl이고, 캐소드 전위가 -0.8 내지 -1.7V임을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
- 제1항 또는 제2항에 있어서, Y가 Cl임을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
- 제1항 또는 제2항에 있어서, X가 Br이고, 캐소드 전위가 -0.4 내지 -1.1V임을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
- 제6항에 있어서, Y가 Br임을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
- 제1항 또는 제2항에 있어서, 캐소드가 은임을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
- 제1항 또는 제2항에 있어서, 은 캐소드가 +0.3 내지 +0.7V의 전위에서 가성 수용액 속에서 양극산화(anodization)된 다음, 역분극화(reverse polarization)됨으로써 활성화됨을 특징으로 하는, 화학식 I의 4-아미노-3-할로피콜린산의 제조방법.
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DE10259362A1 (de) * | 2002-12-18 | 2004-07-08 | Siemens Ag | Verfahren zum Abscheiden einer Legierung auf ein Substrat |
UA82358C2 (uk) * | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкіл або алкеніл-4-амінопіколінати гербіцидна композиція, спосіб боротьби з небажаною рослинністю |
UA81177C2 (uk) * | 2003-08-04 | 2007-12-10 | Дау Агросайєнсіз Ллс | 6-(1,1-дифторалкіл)-4-амінопіколінати та їх використання як гербіцидів |
EP1526192A1 (de) * | 2003-10-24 | 2005-04-27 | Siemens Aktiengesellschaft | Elektrolytisches Verfahren zum Abscheiden einer gradierten Schicht auf ein Substrat und Bauteil |
TWI406849B (zh) * | 2006-10-04 | 2013-09-01 | Dow Agrosciences Llc | 鹵化4-胺基吡啶甲酸之經改良的電化學還原反應 |
US7666293B2 (en) * | 2007-10-04 | 2010-02-23 | Dow Agrosciences Llc | Electrochemical reduction of halogenated 4-aminopicolinic acids |
ITMI20081282A1 (it) * | 2008-07-15 | 2010-01-16 | Industrie De Nora Spa | Processo di trattamento di reflui industriali |
CN101603179B (zh) * | 2009-06-29 | 2013-11-06 | 浙江工业大学 | 3,5,6-三氯吡啶甲酸的电解合成方法 |
JP5818803B2 (ja) * | 2009-10-27 | 2015-11-18 | ダウ アグロサイエンシィズ エルエルシー | 銀陰極活性化の改良 |
TWI529163B (zh) * | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備4-胺基-5-氟-3-鹵素-6-(經取代之)吡啶甲酸酯的方法 |
CN102358944A (zh) * | 2011-08-23 | 2012-02-22 | 哈尔滨理工大学 | 一种氨基吡啶氯化物的制备方法 |
WO2013114404A1 (en) * | 2012-01-31 | 2013-08-08 | Council Of Scientific & Industrial Research | Nano-structured silver oxide film based aqueous voltammetric pesticide sensor and a process of preparing said sensor |
CN104988531B (zh) * | 2015-07-07 | 2017-11-07 | 浙江工业大学 | 一种氯代吡啶甲酸电催化选择性脱氯制备吡啶甲酸的方法 |
CN105803481B (zh) * | 2016-03-22 | 2018-03-27 | 浙江埃森化学有限公司 | 一种催化电解制备4‑氨基‑3,6‑二氯吡啶‑2‑甲酸的方法 |
CN105887129B (zh) * | 2016-05-16 | 2017-12-29 | 浙江工业大学 | 一种三氯甲基吡啶衍生物电化学选择性脱氯制备甲基吡啶衍生物的方法 |
CN105887127B (zh) * | 2016-05-16 | 2017-12-29 | 浙江工业大学 | 一种电化学选择性脱氯制备氯甲基吡啶衍生物的方法 |
CN105887128B (zh) * | 2016-05-16 | 2018-01-12 | 浙江工业大学 | 一种五氯吡啶电催化选择性氢化脱氯的方法 |
CN107778226B (zh) * | 2016-08-26 | 2019-07-02 | 利尔化学股份有限公司 | 一种4-氨基-3,6-二氯吡啶-2-甲酸的纯化方法 |
CN108611656B (zh) * | 2016-12-12 | 2019-07-30 | 利尔化学股份有限公司 | 一种4-氨基-3,6-二氯吡啶-2-甲酸的合成方法 |
CN109763138A (zh) * | 2017-11-09 | 2019-05-17 | 山东润博生物科技有限公司 | 一种3,6-二氯水杨酸的制备方法 |
CN114075675B (zh) * | 2021-11-18 | 2023-09-29 | 永农生物科学有限公司 | 电解脱氯合成4-氨基-3,6-二氯吡啶甲酸的方法及产品和应用 |
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CN1394241A (zh) | 2003-01-29 |
JP2003519726A (ja) | 2003-06-24 |
PT1248867E (pt) | 2003-12-31 |
TW548347B (en) | 2003-08-21 |
MXPA02006890A (es) | 2003-01-28 |
DE60100620T2 (de) | 2004-03-11 |
PL355993A1 (en) | 2004-05-31 |
HU225146B1 (en) | 2006-07-28 |
PL195415B1 (pl) | 2007-09-28 |
NZ519768A (en) | 2002-11-26 |
UA70405C2 (uk) | 2004-10-15 |
HUP0204185A3 (en) | 2003-04-28 |
RU2254401C2 (ru) | 2005-06-20 |
CZ296504B6 (cs) | 2006-03-15 |
EP1248867B1 (en) | 2003-08-20 |
ES2204866T3 (es) | 2004-05-01 |
DK1248867T3 (da) | 2003-12-08 |
TR200301395T4 (tr) | 2004-04-21 |
DE60100620D1 (de) | 2003-09-25 |
RU2002121773A (ru) | 2004-01-10 |
AU2001229457A1 (en) | 2001-07-24 |
CA2396253C (en) | 2009-05-26 |
US6352635B2 (en) | 2002-03-05 |
IL150703A (en) | 2005-09-25 |
JP4615809B2 (ja) | 2011-01-19 |
EP1248867A1 (en) | 2002-10-16 |
CA2396253A1 (en) | 2001-07-19 |
US20010054559A1 (en) | 2001-12-27 |
ATE247726T1 (de) | 2003-09-15 |
HUP0204185A2 (hu) | 2003-03-28 |
CN1238565C (zh) | 2006-01-25 |
KR20020063624A (ko) | 2002-08-03 |
WO2001051684A1 (en) | 2001-07-19 |
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