RU2654464C1 - Method for obtaining coordination compound of copper(ii) with picolinic acid - Google Patents
Method for obtaining coordination compound of copper(ii) with picolinic acid Download PDFInfo
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- RU2654464C1 RU2654464C1 RU2017146530A RU2017146530A RU2654464C1 RU 2654464 C1 RU2654464 C1 RU 2654464C1 RU 2017146530 A RU2017146530 A RU 2017146530A RU 2017146530 A RU2017146530 A RU 2017146530A RU 2654464 C1 RU2654464 C1 RU 2654464C1
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- picolinic acid
- copper
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- picolinate
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- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 229940081066 picolinic acid Drugs 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title description 8
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000010949 copper Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000003792 electrolyte Substances 0.000 claims abstract description 8
- 239000003446 ligand Substances 0.000 claims abstract description 8
- 229910052802 copper Inorganic materials 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- GNWVUSJJFONIKF-UHFFFAOYSA-L copper;pyridine-2-carboxylate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 GNWVUSJJFONIKF-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 239000002244 precipitate Substances 0.000 claims abstract description 6
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 5
- 235000011164 potassium chloride Nutrition 0.000 claims abstract description 4
- 239000001103 potassium chloride Substances 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- -1 chromium picolinate derivatives Chemical class 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LJIHMNONXSBZCU-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)pyridine Chemical compound CCOP(=O)(OCC)CC1=CC=CC=N1 LJIHMNONXSBZCU-UHFFFAOYSA-N 0.000 description 1
- IGHVSFVDNSDRCK-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)quinoline Chemical compound C1=CC=CC2=NC(CP(=O)(OCC)OCC)=CC=C21 IGHVSFVDNSDRCK-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- BOOMHTFCWOJWFO-UHFFFAOYSA-N 3-aminopyridine-2-carboxylic acid Chemical compound NC1=CC=CN=C1C(O)=O BOOMHTFCWOJWFO-UHFFFAOYSA-N 0.000 description 1
- LTUUGSGSUZRPRV-UHFFFAOYSA-N 6-methylpyridine-2-carboxylic acid Chemical compound CC1=CC=CC(C(O)=O)=N1 LTUUGSGSUZRPRV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- LJYRLGOJYKPILZ-UHFFFAOYSA-N murexide Chemical compound [NH4+].N1C(=O)NC(=O)C(N=C2C(NC(=O)NC2=O)=O)=C1[O-] LJYRLGOJYKPILZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- WVWCWWLEFNGDBC-UHFFFAOYSA-N pyridin-2-ylmethylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=N1 WVWCWWLEFNGDBC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Изобретение относится к синтезу химических веществ, а именно к синтезу пиколинатов металлов, которые находят применение в качестве биологически активных добавок в медицине.The invention relates to the synthesis of chemicals, namely the synthesis of metal picolinates, which are used as dietary supplements in medicine.
Известен способ получения координационных соединения хрома с производными пиколиновой кислоты (6-метилпиколиновой кислотой и 3-аминопиколиновой кислотой), заключающийся в постепенном прибавлении водного раствора лиганда с добавкой триэтиламина к раствору нитрата хрома при температуре 100°C и перемешивании в течение часа (Liu В., Liu Y., Chai J., Hu X. et al. Chemical properties and biotoxicity of several chromium picolinate derivatives / Journal of Inorganic Biochemistry. 2016. - Vol. 164. - P. 110-118). Недостатками данного метода являются длительность выделения продукта из раствора (медленное упаривание раствора при комнатной температуре) и невысокий выход (47-53%).A known method for producing coordination compounds of chromium with derivatives of picolinic acid (6-methylpicolinic acid and 3-aminopicolinic acid), which consists in the gradual addition of an aqueous solution of a ligand with the addition of triethylamine to a solution of chromium nitrate at a temperature of 100 ° C and stirring for an hour (Liu B. , Liu Y., Chai J., Hu X. et al. Chemical properties and biotoxicity of several chromium picolinate derivatives / Journal of Inorganic Biochemistry. 2016. - Vol. 164. - P. 110-118). The disadvantages of this method are the duration of the isolation of the product from the solution (slow evaporation of the solution at room temperature) and low yield (47-53%).
Известен способ получения пиколината меди, заключающийся в добавлении метанольного раствора ацетата меди(II) к этанольному раствору 2-пиридилметилфосфоната (2-pmpe) (
Наиболее близким аналогом предлагаемого способа является способ получения пиколината меди, заключающийся в прибавлении нитрила пиколиновой кислоты к водному раствору хлорида меди, содержащему добавку 2-амино-1,3-пропандиола; кристаллы продукта были выделены после кипячения реакционной смеси с обратным холодильником в течение 32 ч. (
Техническим результатом является получение комплексного соединения меди с пиколиновой кислотой (HPic) с меньшими временными затратами.The technical result is to obtain a complex compound of copper with picolinic acid (HPic) with less time.
Технический результат достигается за счет проведения электролиза раствора пиколиновой кислоты с медными электродами при постоянном токе, отделения осадка, промывки осадка и его сушки. В качестве растворителя применяют систему диметилформамид:вода с объемным соотношением компонентов 90:10, в качестве фонового электролита используют хлорид калия. Массовое соотношение ДМФА:вода:пиколиновая кислота:электролит составляет 85,00:10,00:2,50:0,05, плотность тока - 5-8 мА/см2.The technical result is achieved by conducting electrolysis of a solution of picolinic acid with copper electrodes at constant current, separating the precipitate, washing the precipitate and drying it. The solvent used is the dimethylformamide: water system with a volume ratio of components of 90:10, and potassium chloride is used as the background electrolyte. The mass ratio of DMF: water: picolinic acid: electrolyte is 85.00: 10.00: 2.50: 0.05, the current density is 5-8 mA / cm 2 .
Общими с прототипом признаками являются:Common features with the prototype are:
- взаимодействие металла с лигандом (пиколиновой кислотой или ее производным);- the interaction of a metal with a ligand (picolinic acid or its derivative);
- присутствие органического растворителя;- the presence of an organic solvent;
- отделение осадка.- separation of sediment.
Отличительные признаки заявляемого изобретения:Distinctive features of the claimed invention:
- электролиз раствора;- electrolysis of the solution;
- применение в качестве растворителя системы ДМФА:вода в объемном соотношении 90:10;- use as a solvent system DMF: water in a volume ratio of 90:10;
- использование в качестве фонового электролита хлорида калия;- the use of potassium chloride as a background electrolyte;
- массовое соотношение ДМФА:вода:пиколиновая кислота:электролит, составляющее 85,00:10,00:2,50:0,05;- mass ratio of DMF: water: picolinic acid: electrolyte, comprising 85.00: 10.00: 2.50: 0.05;
- плотность тока - 5-8 мА/см2.- current density - 5-8 mA / cm 2 .
На фигуре 1 представлен ИК-спектр синтезированного комплексного соединения; на фигуре 2 - ИК-спектр пиколиновой кислоты.The figure 1 presents the IR spectrum of the synthesized complex compounds; figure 2 - IR spectrum of picolinic acid.
Состав растворителя был подобран экспериментально на основе максимального выхода целевого продукта.The solvent composition was experimentally selected based on the maximum yield of the target product.
Корректность выбора условий синтеза может быть подтверждена данными, приведенными в таблицах 1, 2.The correctness of the choice of synthesis conditions can be confirmed by the data given in tables 1, 2.
Экспериментально установлено, что при плотности тока менее 5 мА/см2 синтез практически не протекает, а при значениях выше 8 мА/см2 наблюдается заметная эрозия электрода, что вызывает загрязнение полученного целевого продукта порошком меди. Это было установлено путем измерения оптической плотности раствора через 30 минут после начала синтеза (оптическая плотность пропорциональна количеству комплексного соединения, накопившегося в растворе). Соответствующие данные приводятся в таблице 1.It was experimentally established that, at a current density of less than 5 mA / cm 2, synthesis does not proceed, and at values above 8 mA / cm 2 , noticeable erosion of the electrode is observed, which causes the obtained product to become contaminated with copper powder. This was established by measuring the optical density of the solution 30 minutes after the start of synthesis (optical density is proportional to the amount of complex compound accumulated in the solution). The relevant data are given in table 1.
Состав растворителя подобран экспериментально, исходя из максимальной растворимости пиколиновой кислоты и минимальной растворимости целевого продукта. Соответствующие данные приведены в таблице 2.The solvent composition is selected experimentally, based on the maximum solubility of picolinic acid and the minimum solubility of the target product. The relevant data are given in table 2.
Пример конкретного выполнения: В двухэлектродную бездиафрагменную ячейку, снабженную двумя медными электродами (объем ячейки 200 мл), помещали 100 мл раствора, содержащего 2,5 г пиколиновой кислоты (состав растворителя - 90 мл ДМФА : 10 мл воды) и 0,05 г хлорида калия, через ячейку пропускали постоянный электрический ток; плотность тока - 8 мА/см2.An example of a specific implementation: In a two-electrode diaphragmless cell equipped with two copper electrodes (cell volume 200 ml), 100 ml of a solution containing 2.5 g of picolinic acid (solvent composition - 90 ml of DMF: 10 ml of water) and 0.05 g of chloride were placed potassium, a constant electric current was passed through the cell; current density - 8 mA / cm 2 .
Через 2 часа выпавший на дно ячейки осадок отфильтровали, высушили на воздухе и анализировали: на содержание металла - методом трилонометрического титрования с мурексидом, на содержание пиколиновой кислоты - методом термического анализа. Данным методом также показано отсутствие сольватной и координированной воды в составе синтезированного соединения. Выход - 76%, результаты анализа на содержание меди и лиганда приведены в таблице 3:After 2 hours, the precipitate deposited at the bottom of the cell was filtered, dried in air and analyzed: for the metal content - by the method of trilonometric titration with murexide, for the content of picolinic acid - by the method of thermal analysis. This method also shows the absence of solvate and coordinated water in the composition of the synthesized compound. The yield is 76%, the results of the analysis for the content of copper and ligand are shown in table 3:
ωCu - массовая доля меди, ωPic - массовая доля пиколиновой кислотыω Cu - mass fraction of copper, ω Pic - mass fraction of picolinic acid
В ИК-спектре синтезированного соединения (Фиг. 1) исчезает полоса поглощения в области 1700 см-1, характерная для валентных колебаний карбоксильной группы в ИК-спектре пиколиновой кислоты (Фиг. 2), и появляются полосы при 1650 и 1350 см-1, характерные для валентных колебаний пиколинат-иона. Разность симметричных и асимметричных колебаний карбоксильной группы, превышающая 160 см-1, свидетельствует о моно-дентатной координации лиганда по карбоксильной группе. Кроме того, в ИК-спектре полученного продукта наблюдается смещение полос в области 1400-1600 см-1, относящихся к колебаниям связей С-N и С-С ароматического цикла, что служит свидетельством координации пиколиновой кислоты также по атому азота пиридинового кольца.In the IR spectrum of the synthesized compound (Fig. 1), the absorption band in the region of 1700 cm -1 characteristic of stretching vibrations of the carboxyl group in the IR spectrum of picolinic acid disappears (Fig. 2), and bands appear at 1650 and 1350 cm -1 , characteristic of stretching vibrations of the picolinate ion. The difference in symmetric and asymmetric vibrations of the carboxyl group, exceeding 160 cm -1 , indicates monodentate coordination of the ligand with the carboxyl group. In addition, in the IR spectrum of the obtained product, a shift of bands is observed in the region of 1400-1600 cm -1 related to vibrations of the С-N and С-С bonds of the aromatic cycle, which serves as evidence of the coordination of picolinic acid also at the nitrogen atom of the pyridine ring.
На основании представленных данных можно сделать вывод о том, что технический результат - уменьшение временных затрат - достигается. Время синтеза необходимое для получения целевого продукта уменьшилось в 16 раз. Такой результат обеспечили отличительные признаки предлагаемого способа. Таким образом, заявляемый способ удовлетворяет критериям охраноспособости, т.е. является изобретением.Based on the data presented, we can conclude that the technical result - reducing time costs - is achieved. The synthesis time required to obtain the target product decreased by 16 times. This result was provided by the distinctive features of the proposed method. Thus, the claimed method meets the eligibility criteria, i.e. is an invention.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2711449C1 (en) * | 2019-09-27 | 2020-01-17 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный университет" (ФГБОУ ВО "КубГУ") | Method of producing a zinc-picolinic acid coordination compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1529775B1 (en) * | 2001-12-17 | 2006-04-19 | JH Biotech, Inc. | Method for preparation of metal organic acid chelates |
| RU2415860C1 (en) * | 2009-08-18 | 2011-04-10 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный университет" (ГОУ ВПО КубГУ) | Method of producing complex compound of copper and pyridoxine |
| CN103450231A (en) * | 2013-09-14 | 2013-12-18 | 罗梅 | Synthesis method of biso-copper picolinate dihydrate complex |
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2017
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| EP1529775B1 (en) * | 2001-12-17 | 2006-04-19 | JH Biotech, Inc. | Method for preparation of metal organic acid chelates |
| RU2415860C1 (en) * | 2009-08-18 | 2011-04-10 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный университет" (ГОУ ВПО КубГУ) | Method of producing complex compound of copper and pyridoxine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2711449C1 (en) * | 2019-09-27 | 2020-01-17 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный университет" (ФГБОУ ВО "КубГУ") | Method of producing a zinc-picolinic acid coordination compound |
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