DD152366A5 - Verfahren zur elektrolytischen reduktion eines chlorsubstituenten von polychlorpicolinsaeuren - Google Patents
Verfahren zur elektrolytischen reduktion eines chlorsubstituenten von polychlorpicolinsaeuren Download PDFInfo
- Publication number
- DD152366A5 DD152366A5 DD80222307A DD22230780A DD152366A5 DD 152366 A5 DD152366 A5 DD 152366A5 DD 80222307 A DD80222307 A DD 80222307A DD 22230780 A DD22230780 A DD 22230780A DD 152366 A5 DD152366 A5 DD 152366A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acid
- cathode
- picolinic acid
- tetrachloro
- solution
- Prior art date
Links
- 230000009467 reduction Effects 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 45
- 239000000460 chlorine Substances 0.000 title claims description 24
- 229910052801 chlorine Inorganic materials 0.000 title claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 title 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 claims abstract description 53
- 230000008569 process Effects 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 56
- 239000000243 solution Substances 0.000 claims description 39
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 38
- 229910052709 silver Inorganic materials 0.000 claims description 37
- 239000004332 silver Substances 0.000 claims description 37
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000002245 particle Substances 0.000 claims description 19
- SKURPVMALGSJSE-UHFFFAOYSA-N 3,4,5-trichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(Cl)C(Cl)=C1Cl SKURPVMALGSJSE-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 16
- 239000004020 conductor Substances 0.000 claims description 15
- 238000005868 electrolysis reaction Methods 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 14
- -1 hydroxyl ions Chemical class 0.000 claims description 12
- 150000002500 ions Chemical class 0.000 claims description 12
- 239000010410 layer Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910001923 silver oxide Inorganic materials 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 239000013081 microcrystal Substances 0.000 claims description 7
- 239000010953 base metal Substances 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229940081066 picolinic acid Drugs 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000002344 surface layer Substances 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- TVMKSGXYTVKNRK-UHFFFAOYSA-N 3,5,6-trichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(Cl)=C(Cl)C=C1Cl TVMKSGXYTVKNRK-UHFFFAOYSA-N 0.000 abstract description 16
- GTYZPIAEJJABMS-UHFFFAOYSA-N 3,4,6-trichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(Cl)=CC(Cl)=C1Cl GTYZPIAEJJABMS-UHFFFAOYSA-N 0.000 abstract description 12
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 138
- 210000004027 cell Anatomy 0.000 description 45
- 238000006722 reduction reaction Methods 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 229910002804 graphite Inorganic materials 0.000 description 11
- 239000010439 graphite Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- VXHRMDQLQCJZDH-UHFFFAOYSA-N C1(C(=C(C(C(C1(Cl)Cl)[N+](=O)[O-])(Cl)Cl)[N+](=O)[O-])O)[N+](=O)[O-] Chemical class C1(C(=C(C(C(C1(Cl)Cl)[N+](=O)[O-])(Cl)Cl)[N+](=O)[O-])O)[N+](=O)[O-] VXHRMDQLQCJZDH-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000013459 approach Methods 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- WAXYNGRWFLQXTD-UHFFFAOYSA-N ClC1([N+](=O)[O-])CC([N+](=O)[O-])=C(C([N+](=O)[O-])=C1O)Cl Chemical compound ClC1([N+](=O)[O-])CC([N+](=O)[O-])=C(C([N+](=O)[O-])=C1O)Cl WAXYNGRWFLQXTD-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XTMUXJBJCMRWPG-UHFFFAOYSA-N 3-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=C1Cl XTMUXJBJCMRWPG-UHFFFAOYSA-N 0.000 description 3
- ZLKMOIHCHCMSFW-UHFFFAOYSA-N 6-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(Cl)=N1 ZLKMOIHCHCMSFW-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- AFZMKBLOQNTBOT-UHFFFAOYSA-N 3,4-dichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(Cl)=C1Cl AFZMKBLOQNTBOT-UHFFFAOYSA-N 0.000 description 2
- FGHSIAVNLWSGBY-UHFFFAOYSA-N 3,5,6-trichloro-4-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(Cl)=C(Cl)C(O)=C1Cl FGHSIAVNLWSGBY-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- LHGPMHVLPPBBDY-UHFFFAOYSA-N C1(C(=C(C(=C(C1([N+](=O)[O-])Cl)O)[N+](=O)[O-])Cl)[N+](=O)[O-])Cl Chemical compound C1(C(=C(C(=C(C1([N+](=O)[O-])Cl)O)[N+](=O)[O-])Cl)[N+](=O)[O-])Cl LHGPMHVLPPBBDY-UHFFFAOYSA-N 0.000 description 2
- FVKYZGYFCQMRHA-UHFFFAOYSA-N C1C(C(C(=C(C1([N+](=O)[O-])Cl)O)[N+](=O)[O-])Cl)([N+](=O)[O-])Cl Chemical compound C1C(C(C(=C(C1([N+](=O)[O-])Cl)O)[N+](=O)[O-])Cl)([N+](=O)[O-])Cl FVKYZGYFCQMRHA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000012876 topography Methods 0.000 description 2
- DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 description 1
- VMHZXXPDUOVTHD-UHFFFAOYSA-N 2,3,4-trichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1Cl VMHZXXPDUOVTHD-UHFFFAOYSA-N 0.000 description 1
- FATBKZJZAHWCSL-UHFFFAOYSA-N 2,3,5,6-tetrachloropyridine Chemical compound ClC1=CC(Cl)=C(Cl)N=C1Cl FATBKZJZAHWCSL-UHFFFAOYSA-N 0.000 description 1
- KFPBGJYBKSQIAI-UHFFFAOYSA-N 3,4,5,6-tetrachloropyridine-2-carbonitrile Chemical compound ClC1=NC(C#N)=C(Cl)C(Cl)=C1Cl KFPBGJYBKSQIAI-UHFFFAOYSA-N 0.000 description 1
- NNMYRMGMVLMQAY-UHFFFAOYSA-N 4-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=N1 NNMYRMGMVLMQAY-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920005479 Lucite® Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 238000009825 accumulation Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012611 container material Substances 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 210000001787 dendrite Anatomy 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003411 electrode reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- RECVMTHOQWMYFX-UHFFFAOYSA-N oxygen(1+) dihydride Chemical compound [OH2+] RECVMTHOQWMYFX-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- HAAYBYDROVFKPU-UHFFFAOYSA-N silver;azane;nitrate Chemical compound N.N.[Ag+].[O-][N+]([O-])=O HAAYBYDROVFKPU-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000036228 toxication Effects 0.000 description 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
- C25B11/075—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound
- C25B11/081—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound the element being a noble metal
Landscapes
- 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)
- Electrodes For Compound Or Non-Metal Manufacture (AREA)
- Pyridine Compounds (AREA)
- Electrolytic Production Of Metals (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/054,130 US4217185A (en) | 1979-07-02 | 1979-07-02 | Electrolytic production of certain trichloropicolinic acids and/or 3,6-dichloropicolinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD152366A5 true DD152366A5 (de) | 1981-11-25 |
Family
ID=21988973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80222307A DD152366A5 (de) | 1979-07-02 | 1980-07-01 | Verfahren zur elektrolytischen reduktion eines chlorsubstituenten von polychlorpicolinsaeuren |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4217185A (cs) |
| EP (1) | EP0023077B1 (cs) |
| JP (1) | JPS569382A (cs) |
| KR (1) | KR840000447B1 (cs) |
| AR (1) | AR225441A1 (cs) |
| AU (1) | AU529604B2 (cs) |
| BR (1) | BR8004103A (cs) |
| CA (1) | CA1142877A (cs) |
| CS (1) | CS222175B2 (cs) |
| DD (1) | DD152366A5 (cs) |
| DE (1) | DE3068297D1 (cs) |
| DK (1) | DK152591C (cs) |
| ES (1) | ES8106564A1 (cs) |
| GB (1) | GB2056492B (cs) |
| HU (1) | HU182150B (cs) |
| IL (1) | IL59928A (cs) |
| IN (1) | IN152627B (cs) |
| MY (1) | MY8500086A (cs) |
| NZ (1) | NZ193544A (cs) |
| SU (1) | SU1077568A3 (cs) |
| UA (1) | UA6322A1 (cs) |
| ZA (1) | ZA802659B (cs) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334074A (en) * | 1981-02-02 | 1982-06-08 | The Dow Chemical Company | Method of recovering 3,6-dichloropicolinic acid from basic aqueous solutions of salts thereof |
| US4592811A (en) * | 1981-09-28 | 1986-06-03 | The Dow Chemical Company | Electrolytic cell comprising stainless steel anode, basic aqueous electrolyte and a cathode at which tetrachloro-2-picolinate ions can be selectively reduced in high yield to 3,6-dichloropicolinate ions _ |
| EP0209611A1 (en) * | 1985-07-18 | 1987-01-28 | The Dow Chemical Company | Electrolytic cell comprising stainless steel anode and a process for preparing polychloropicolinate anions |
| US4533454A (en) * | 1981-09-28 | 1985-08-06 | The Dow Chemical Company | Electrolytic cell comprising stainless steel anode, basic aqueous electrolyte and a cathode at which tetrachloro-2-picolinate ions can be selectively reduced in high yield to 3,6-dichloropicolinate ions |
| US4460441A (en) * | 1982-08-31 | 1984-07-17 | The Dow Chemical Company | Expanded metal as more efficient form of silver cathode for electrolytic reduction of polychloropicolinate anions |
| JPS60187355A (ja) * | 1983-12-05 | 1985-09-24 | Tipton Mfg Corp | 水中選別方法および装置 |
| US4497697A (en) * | 1984-03-02 | 1985-02-05 | The Dow Chemical Company | Electrolytic preparation of 3,6-dichloropicolinic acid |
| JPH0670277B2 (ja) * | 1984-06-14 | 1994-09-07 | ザ・ダウ・ケミカル・カンパニー | ポリクロロピコリネートアニオンの電解還元用エキスパンデッドメタル銀電極 |
| US4755266A (en) * | 1986-07-11 | 1988-07-05 | The Dow Chemical Company | Process for silver cathode activation |
| US4778576A (en) * | 1986-07-31 | 1988-10-18 | The Dow Chemical Company | Nickel alloy anodes for electrochemical dechlorination |
| GB8712989D0 (en) * | 1987-06-03 | 1987-07-08 | Ici Plc | Electrochemical process |
| DE19620861A1 (de) * | 1996-05-23 | 1997-11-27 | Basf Ag | Verfahren zur elektrochemischen Reduktion organischer Verbindungen |
| CA2302769A1 (en) * | 1997-09-05 | 1999-03-18 | Basf Aktiengesellschaft | Electrochemical reduction of organic compounds |
| KR100727279B1 (ko) * | 2000-01-14 | 2007-06-13 | 다우 아그로사이언시즈 엘엘씨 | 할로겐화 4-아미노피콜린산의 선택적 전기화학적 환원 방법 |
| DE10234285B4 (de) * | 2002-07-26 | 2006-12-07 | Heraeus Kulzer Gmbh | Vorrichtung zur galvanischen Abscheidung prothetischer, metallischer Dentalformteile |
| US7842178B2 (en) * | 2005-04-18 | 2010-11-30 | University Of Iowa Research Foundation | Magnet incorporated electrically conductive electrodes |
| CN100436648C (zh) * | 2005-12-16 | 2008-11-26 | 浙江工业大学 | 3,6-二氯吡啶甲酸的电解合成方法及设备 |
| DE202006008329U1 (de) * | 2006-03-30 | 2006-08-10 | Leica Microsystems Nussloch Gmbh | Mikrotom |
| US7666293B2 (en) * | 2007-10-04 | 2010-02-23 | Dow Agrosciences Llc | Electrochemical reduction of halogenated 4-aminopicolinic acids |
| CN101235515B (zh) * | 2008-02-27 | 2010-06-23 | 浙江工业大学 | 一种活性银电极的制备方法 |
| EP2494095B1 (en) * | 2009-10-27 | 2014-04-23 | Dow AgroSciences LLC | Improved silver cathode activation |
| CN102732911B (zh) * | 2012-06-18 | 2016-01-13 | 北京颖泰嘉和生物科技股份有限公司 | 用于电解合成3,6-二氯吡啶甲酸的电极、电解设备和方法 |
| KR20170038818A (ko) * | 2014-08-06 | 2017-04-07 | 다우 아그로사이언시즈 엘엘씨 | 4,5,6-트리클로로피콜린산의 제조 방법 |
| CN105671588B (zh) * | 2016-03-22 | 2018-03-27 | 浙江埃森化学有限公司 | 3,4,5,6‑四氯吡啶‑2‑甲酸催化电解制备3,6‑二氯吡啶‑2‑甲酸的方法 |
| 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 |
| CN107382843A (zh) * | 2017-07-24 | 2017-11-24 | 连云港埃森化学有限公司 | 一种3,6‑二氯吡啶甲酸钾的合成工艺 |
| CN110656345B (zh) * | 2019-08-23 | 2021-06-08 | 浙江工业大学 | 一种4-氨基-3,6-二氯吡啶甲酸的电解合成方法 |
| CN119592966B (zh) * | 2024-12-24 | 2025-10-10 | 浙江工业大学 | 高选择性脱氯电催化合成酯类化合物的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3377160A (en) * | 1964-12-31 | 1968-04-09 | Allis Chalmers Mfg Co | Process of making a high surface area silver catalyst |
| DE1567689A1 (de) * | 1965-10-09 | 1970-06-11 | Barthel Dipl Chem Guenter | Elektrode fuer die elektrolytische Zerlegung von Salzsaeure und Verfahren zu ihrer Herstellung |
| US3687826A (en) * | 1971-01-25 | 1972-08-29 | Dow Chemical Co | Electrolytic reduction of polyhaloquinoline and polyhaloisoquinoline |
| US3694332A (en) * | 1971-03-05 | 1972-09-26 | Dow Chemical Co | Electrolytic reduction of halogenated pyridines |
| US3677916A (en) * | 1971-03-11 | 1972-07-18 | Dow Chemical Co | Electrolytic reduction of 1,2,3,4-tetrachlorobenzene to obtain 1,2,4-trichlorobenzene |
| US3971799A (en) * | 1974-12-27 | 1976-07-27 | The Dow Chemical Company | Preparation of 3,5,6-trichloropicolinic acid |
-
1979
- 1979-07-02 US US06/054,130 patent/US4217185A/en not_active Expired - Lifetime
-
1980
- 1980-04-22 CA CA000350346A patent/CA1142877A/en not_active Expired
- 1980-04-25 IL IL59928A patent/IL59928A/xx unknown
- 1980-04-28 NZ NZ193544A patent/NZ193544A/xx unknown
- 1980-05-01 AU AU57990/80A patent/AU529604B2/en not_active Ceased
- 1980-05-02 ZA ZA00802659A patent/ZA802659B/xx unknown
- 1980-05-05 IN IN520/CAL/80A patent/IN152627B/en unknown
- 1980-05-21 EP EP80301684A patent/EP0023077B1/en not_active Expired
- 1980-05-21 DE DE8080301684T patent/DE3068297D1/de not_active Expired
- 1980-05-21 GB GB8016731A patent/GB2056492B/en not_active Expired
- 1980-05-23 ES ES491777A patent/ES8106564A1/es not_active Expired
- 1980-05-28 DK DK229680A patent/DK152591C/da active
- 1980-05-29 AR AR281229A patent/AR225441A1/es active
- 1980-06-23 JP JP8503680A patent/JPS569382A/ja active Granted
- 1980-06-26 KR KR1019800002517A patent/KR840000447B1/ko not_active Expired
- 1980-06-30 BR BR8004103A patent/BR8004103A/pt not_active IP Right Cessation
- 1980-07-01 UA UA2940707A patent/UA6322A1/uk unknown
- 1980-07-01 CS CS804694A patent/CS222175B2/cs unknown
- 1980-07-01 DD DD80222307A patent/DD152366A5/de unknown
- 1980-07-01 SU SU802940707A patent/SU1077568A3/ru active
- 1980-07-02 HU HU801644A patent/HU182150B/hu unknown
-
1985
- 1985-12-30 MY MY86/85A patent/MY8500086A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2056492A (en) | 1981-03-18 |
| BR8004103A (pt) | 1981-01-27 |
| IL59928A (en) | 1984-02-29 |
| JPS6249357B2 (cs) | 1987-10-19 |
| EP0023077A3 (en) | 1981-06-03 |
| ZA802659B (en) | 1981-07-29 |
| CA1142877A (en) | 1983-03-15 |
| DK229680A (da) | 1981-01-03 |
| ES491777A0 (es) | 1981-07-01 |
| GB2056492B (en) | 1983-04-27 |
| NZ193544A (en) | 1983-06-14 |
| ES8106564A1 (es) | 1981-07-01 |
| DK152591C (da) | 1988-09-12 |
| AU5799080A (en) | 1981-01-15 |
| EP0023077A2 (en) | 1981-01-28 |
| AU529604B2 (en) | 1983-06-16 |
| DK152591B (da) | 1988-03-21 |
| JPS569382A (en) | 1981-01-30 |
| HU182150B (en) | 1983-12-28 |
| UA6322A1 (uk) | 1994-12-29 |
| IN152627B (cs) | 1984-02-25 |
| DE3068297D1 (en) | 1984-07-26 |
| EP0023077B1 (en) | 1984-06-20 |
| KR830002711A (ko) | 1983-05-30 |
| KR840000447B1 (ko) | 1984-04-07 |
| SU1077568A3 (ru) | 1984-02-29 |
| AR225441A1 (es) | 1982-03-31 |
| CS222175B2 (en) | 1983-05-27 |
| IL59928A0 (en) | 1980-06-30 |
| US4217185A (en) | 1980-08-12 |
| MY8500086A (en) | 1985-12-31 |
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