CN104988531A - 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 - Google Patents
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 Download PDFInfo
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- CN104988531A CN104988531A CN201510401434.7A CN201510401434A CN104988531A CN 104988531 A CN104988531 A CN 104988531A CN 201510401434 A CN201510401434 A CN 201510401434A CN 104988531 A CN104988531 A CN 104988531A
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- 238000000034 method Methods 0.000 title claims abstract description 36
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title claims abstract description 33
- NNMYRMGMVLMQAY-UHFFFAOYSA-N 4-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=N1 NNMYRMGMVLMQAY-UHFFFAOYSA-N 0.000 title abstract 5
- 229940081066 picolinic acid Drugs 0.000 title abstract 5
- 238000006555 catalytic reaction Methods 0.000 title abstract 2
- 239000004020 conductor Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 12
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- 239000000203 mixture Substances 0.000 claims abstract description 7
- 239000010970 precious metal Substances 0.000 claims abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 60
- DIIMYURFOKYFTB-UHFFFAOYSA-N C(=O)O.ClC1=NC=CC=C1 Chemical compound C(=O)O.ClC1=NC=CC=C1 DIIMYURFOKYFTB-UHFFFAOYSA-N 0.000 claims description 36
- 238000006298 dechlorination reaction Methods 0.000 claims description 31
- 229910052763 palladium Inorganic materials 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- -1 4-amino-3-chloropyridine formic acid Chemical compound 0.000 claims description 13
- 239000003115 supporting electrolyte Substances 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 229910002804 graphite Inorganic materials 0.000 claims description 8
- 239000010439 graphite Substances 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- NBSITWJPOCDKDQ-UHFFFAOYSA-N C(=O)O.ClC=1C=NC=CC1 Chemical compound C(=O)O.ClC=1C=NC=CC1 NBSITWJPOCDKDQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004744 fabric Substances 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
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- 239000004917 carbon fiber Substances 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001940 conductive polymer Polymers 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000008151 electrolyte solution Substances 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- 229920000128 polypyrrole Polymers 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 239000002322 conducting polymer Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 235000010338 boric acid Nutrition 0.000 claims 1
- 235000011167 hydrochloric acid Nutrition 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000005500 Clopyralid Substances 0.000 abstract 2
- 239000003792 electrolyte Substances 0.000 abstract 2
- JRZBTJVSAANBEV-UHFFFAOYSA-N 4-aminopyridine-2-carboxylic acid Chemical compound NC1=CC=NC(C(O)=O)=C1 JRZBTJVSAANBEV-UHFFFAOYSA-N 0.000 abstract 1
- 238000005868 electrolysis reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 239000012528 membrane Substances 0.000 description 7
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- 238000002474 experimental method Methods 0.000 description 6
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- 229910021607 Silver chloride Inorganic materials 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- UUWCBFKLGFQDME-UHFFFAOYSA-N platinum titanium Chemical compound [Ti].[Pt] UUWCBFKLGFQDME-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- OZDBLSXEJXYHPV-UHFFFAOYSA-N formic acid pyridin-4-amine Chemical compound C(=O)O.NC1=CC=NC=C1 OZDBLSXEJXYHPV-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000004904 shortening Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 229910052697 platinum Inorganic materials 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical group OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 1
- ZNMCIIPJPRILQT-UHFFFAOYSA-N 3,5,6-trichloro-4-methylpyridine-2-carboxylic acid Chemical compound CC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl ZNMCIIPJPRILQT-UHFFFAOYSA-N 0.000 description 1
- BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 1
- AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 description 1
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- JOSDQWPRIVOTIM-UHFFFAOYSA-N pyridine;pyridine-2-carboxylic acid Chemical group C1=CC=NC=C1.OC(=O)C1=CC=CC=N1 JOSDQWPRIVOTIM-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Pyridine Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
Description
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Cited By (12)
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CN105461621A (zh) * | 2015-12-24 | 2016-04-06 | 浙江埃森化学有限公司 | 多氯代吡啶-2-甲酸混合物加氢还原制备吡啶-2-甲酸的方法 |
CN105671588A (zh) * | 2016-03-22 | 2016-06-15 | 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 |
CN105803481A (zh) * | 2016-03-22 | 2016-07-27 | 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 |
CN105887129A (zh) * | 2016-05-16 | 2016-08-24 | 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 |
CN105887127A (zh) * | 2016-05-16 | 2016-08-24 | 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 |
CN110656345A (zh) * | 2019-08-23 | 2020-01-07 | 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 |
CN111647906A (zh) * | 2020-04-03 | 2020-09-11 | 杭州师范大学 | 一种银或银镍合金催化的电化学脱氯处理二氯甲烷的方法 |
CN112824563A (zh) * | 2019-11-19 | 2021-05-21 | 万华化学集团股份有限公司 | 一种成对电解同时制备吡啶甲酸和芳香氯化物脱氯还原产物的方法 |
CN113030334A (zh) * | 2021-03-25 | 2021-06-25 | 哈尔滨工业大学(深圳) | 一种使用高效液相色谱仪(hplc)对四氯吡啶甲酸含量检测的方法 |
CN113846342A (zh) * | 2021-10-13 | 2021-12-28 | 浙江工业大学 | 以无机-有机核壳骨架负载低剂量贵金属钯材料及其制备与在电催化脱氯加氢反应中的应用 |
CN114075675A (zh) * | 2021-11-18 | 2022-02-22 | 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 |
CN116288430A (zh) * | 2023-02-01 | 2023-06-23 | 浙江工业大学 | 一种提高4-氨基-3,6-二氯吡啶甲酸电解合成效率的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1394241A (zh) * | 2000-01-14 | 2003-01-29 | 美国陶氏益农公司 | 卤代的4-氨基吡啶甲酸的选择性电化学还原 |
CN102409354A (zh) * | 2011-04-20 | 2012-04-11 | 横店集团东阳英洛华绿色电化学有限公司 | 一种2-吡啶甲酸的电解合成方法 |
CN104087968A (zh) * | 2014-06-13 | 2014-10-08 | 浙江工业大学 | 卤代吡啶甲酸或其盐类化合物的选择性电化学还原方法 |
-
2015
- 2015-07-07 CN CN201510401434.7A patent/CN104988531B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1394241A (zh) * | 2000-01-14 | 2003-01-29 | 美国陶氏益农公司 | 卤代的4-氨基吡啶甲酸的选择性电化学还原 |
CN102409354A (zh) * | 2011-04-20 | 2012-04-11 | 横店集团东阳英洛华绿色电化学有限公司 | 一种2-吡啶甲酸的电解合成方法 |
CN104087968A (zh) * | 2014-06-13 | 2014-10-08 | 浙江工业大学 | 卤代吡啶甲酸或其盐类化合物的选择性电化学还原方法 |
Non-Patent Citations (1)
Title |
---|
HONGXING MA等: "Electrocatalytic dechlorination of chloropicolinic acid mixtures by using palladium-modified metal cathodes in aqueous solutions", 《ELECTROCHIMICA ACTA》 * |
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