CN103613536A - Industrialized preparation method of 2-copper picolinate - Google Patents
Industrialized preparation method of 2-copper picolinate Download PDFInfo
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- CN103613536A CN103613536A CN201310676592.4A CN201310676592A CN103613536A CN 103613536 A CN103613536 A CN 103613536A CN 201310676592 A CN201310676592 A CN 201310676592A CN 103613536 A CN103613536 A CN 103613536A
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- carboxylic acid
- pyridine carboxylic
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- acid copper
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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
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Abstract
The invention discloses an industrialized preparation method of 2-copper picolinate. The method comprises the following steps: (1) charging and warming: adding 123.5-494kg of 2-picolinic acid into a 2000L reaction kettle, adding 175-600kg of water, and warming to 90 DEG C to stir and dissolve; (2) dissolving, cooling, adjusting pH and stirring: after fully dissolving 2-picolinic acid, cooling to 70-78 DEG C, adjusting the pH to 6-7 by liquid caustic soda, and then stirring for 1-2 hours; (3) a reaction step: adding 125-500kg of copper sulfate pentahydrate, and reacting for 1.7-3 hours at 90-98 DEG C; and (4) product separation: cooling to room temperature, centrifugalizing and drying at 90 DEG C to obtain 2-copper picolinate blue powder. Compared with the prior art, the industrialized preparation method of 2-copper picolinate protected by the invention is simple in synthetic line, safe and reliable in process, short in reaction period, high in yield, good in product quality and free from pollutants.
Description
Technical field
The present invention relates to a kind of industrialized process for preparing of 2-pyridine carboxylic acid copper.
Background technology
2-pyridine carboxylic acid has special physiologically active, belong to organic formic acid, also be the very important bio-ligand of a class simultaneously, in molecule, contain can with group carboxyl and the heterocycle of different metal coordination, 2-pyridine carboxylic acid and derivative thereof are the intermediates of multi-medicament, all widespread uses in medicine, agricultural and household chemicals.Copper is teleorganic trace element, is prevalent in animal and plant body, in vital process, plays an important role.Cupric ion because of the diversity of its good coordination ability and structure be the important ion that synthetic compound is selected always. select to have the synthetic new copper complex of part of biological function, all significant to biology, inorganic chemistry, medicine, feedstuff industry and application.
2-pyridine carboxylic acid copper is the super molecular complex of 2-pyridine carboxylic acid and cupric ion, remarkable specific absorption and bioavailability aspect Animal nutrition, it not only can avoid the excessive interpolation of Inorganic Copper element to use, and has brought a series of environmental pollution, has eaten the problems such as poisoning and nutritive substance waste.Meanwhile, as a kind of important organic copper sources, can effectively improve governing speed, metabolic process, the antigen effect of body.
Along with people deepen continuously to the understanding of metallo-chelate, its utilization ratio, range of application are also constantly expanding, and explore a kind of Technology of applicable suitability for industrialized production, also just become the bottleneck of the sector development.
Up to now, the product that still there is no 2-pyridine carboxylic acid copper on market.
Summary of the invention
Object of the present invention is just to provide a kind of industrialized process for preparing of 2-pyridine carboxylic acid copper, and the industrialized process for preparing synthetic route of this 2-pyridine carboxylic acid copper is simple, and process safety is reliable, and reaction time is short, yield is high, good product quality, and contamination-free produces.
Technical scheme of the present invention is: a kind of industrialized process for preparing of 2-pyridine carboxylic acid copper, comprises the following steps:
1. reinforced intensification: add 2-pyridine carboxylic acid 123.5kg-494kg in the reactor of 2000L, add water 175kg-600kg, be warming up to 90 ℃ of stirring and dissolving;
2. dissolve, lower the temperature, adjust PH and stirring: after 2-pyridine carboxylic acid fully dissolves, cool the temperature to 70 ℃-78 ℃, with liquid caustic soda, be adjusted to PH=6-7, then stir 1-2h;
3. reactions steps: add cupric sulfate pentahydrate 125kg-500kg, at 90-98 ℃ of reaction 1.7-3h;
4. product separation: be down to room temperature, centrifugal, 90 ℃ dry, obtains 2-pyridine carboxylic acid copper blue powder.
As preferably, described step 3. in, cupric sulfate pentahydrate is incorporated as in batches and adds, and within 15 minutes, adds once, each 25kg-100kg.
As preferably, described 2-pyridine carboxylic acid Chun Du≤99%, cupric sulfate pentahydrate Chun Du≤98%.
Inventive principle:
When temperature of reaction is during lower than optimum temps, reaction can not fully be carried out, and causes product content on the low side, and yield reduces.When excess Temperature, can generate a certain amount of cupric oxide, cause product content too high, shape is unstable.In the time of between pH value is higher than reaction optimal zone, in reaction, has copper hydroxide and produce, cause product content to raise, when ph value of reaction is low, can affect product yield.
Beneficial effect:
The present invention proposes the scheme that a kind of applicable 2-pyridine carboxylic acid Copper Processing Industryization is produced, the series of problems of not only having avoided lengthy and tedious operating process to bring, also for scale operation, reduction provide corresponding reference frame, to promoting the application of 2-pyridine carboxylic acid copper, play active effect.
Synthetic route of the present invention is simple, and process safety is reliable, and reaction time is short, yield is high, good product quality, and contamination-free produces.
The 2-pyridine carboxylic acid copper products that the present invention makes is blue crystalline powder, 2-pyridine carboxylic acid Tong Han Liang≤99.0%, and yield is 93.6%.
The 2-pyridine carboxylic acid copper that the present invention makes is as new copper nutritious supplementary.
Embodiment
The present invention is further illustrated for structure specific embodiment below.
Embodiment 1
In the reactor of 1000L, add 2-pyridine carboxylic acid 123.5kg, add water 175kg, be warming up to 90 ℃ of stirring and dissolving; After 2-pyridine carboxylic acid fully dissolves, temperature is down to 72 ℃, with liquid caustic soda, is adjusted to PH=6.4, then stirs 1.5h; Add in batches cupric sulfate pentahydrate 125kg, within 15 minutes, add once, each 25kg.Finish, at 94 ℃ of reaction 2.5h; Be down to room temperature, centrifugal, 90 ℃ are dry, obtain 2-pyridine carboxylic acid copper 144.61kg, are blue crystalline powder, 2-pyridine carboxylic acid copper content Wei≤99.27%, and yield is 94.11%.
Embodiment 2
In the reactor of 2000L, add 2-pyridine carboxylic acid 247kg, add water 350kg, be warming up to 90 ℃ of stirring and dissolving; After 2-pyridine carboxylic acid fully dissolves, temperature is down to 78 ℃, with liquid caustic soda, is adjusted to PH=6, then stirs 1.5h; Add in batches cupric sulfate pentahydrate 250kg, within 15 minutes, add once, each 50kg.Finish, at 98 ℃ of reaction 1.7h; Be down to room temperature, centrifugal, 90 ℃ are dry, obtain 2-pyridine carboxylic acid copper 288.73kg, are blue crystalline powder, 2-pyridine carboxylic acid copper content Wei≤99.64%, and yield is 94.31%.
Embodiment 3
In the reactor of 4000L, add 2-pyridine carboxylic acid 494kg, add water 600kg, be warming up to 90 ℃ of stirring and dissolving; After 2-pyridine carboxylic acid fully dissolves, temperature is down to 76 ℃, with liquid caustic soda, is adjusted to PH=6.5, then stirs 2h; Add in batches cupric sulfate pentahydrate 500kg, within 15 minutes, add once, each 100kg.Finish, at 96 ℃ of reaction 3h; Be down to room temperature, centrifugal, 90 ℃ are dry, obtain 2-pyridine carboxylic acid copper 577.24kg, are blue crystalline powder, 2-pyridine carboxylic acid copper content Wei≤99.28%, and yield is 94.07%.
Embodiment 4
In the reactor of 2000L, add 2-pyridine carboxylic acid 164.6kg, add 234kg, be warming up to 90 ℃ of stirring and dissolving; After 2-pyridine carboxylic acid fully dissolves, temperature is down to 70 ℃, with liquid caustic soda, is adjusted to PH=7, then stirs 1h; Add in batches cupric sulfate pentahydrate 166.6kg, within 15 minutes, add once, each 33.32kg.Finish, at 90 ℃ of reaction 2h; Be down to room temperature, centrifugal, 90 ℃ are dry, obtain 2-pyridine carboxylic acid copper 198.35kg, are blue crystalline powder, 2-pyridine carboxylic acid copper content Wei≤99.72%, and yield is 96.14%.
In above-described embodiment, 2-pyridine carboxylic acid copper content testing method is as follows:
At Silver Nitrate, do under catalyzer and phosphoric acid medium condition, 2-pyridine carboxylic acid copper is cleared up into Cu2+ by Sodium Persulfate oxidation, so, by the content of indirect iodometric determination copper.In mensuration 2-pyridine carboxylic acid copper, cu content contributes to judge the proportioning of 2-pyridine carboxylic acid copper, and the purity of pyridine carboxylic acid copper is recently determined in available cooperation.
Use 2-pyridine carboxylic acid copper standard substance (being accurate to 0.0001g) to carry out standardized solution preparation.
HPLC method chromatographic condition:
Chromatographic column: ODS-C18 (5um), long 250mm, internal diameter 4.6mm
Moving phase: methyl alcohol: water=30:70
Flow velocity 0.8mlmin-1
UV-detector detects wavelength: 265nm
Sample size: 10ul
Retention time: 3.62min.
Claims (3)
1. an industrialized process for preparing for 2-pyridine carboxylic acid copper, comprises the following steps:
1. reinforced intensification: add 2-pyridine carboxylic acid 123.5kg-494kg in the reactor of 2000L, add water 175kg-600kg, be warming up to 90 ℃ of stirring and dissolving;
2. dissolve, lower the temperature, adjust PH and stirring: after 2-pyridine carboxylic acid fully dissolves, cool the temperature to 70 ℃-78 ℃, with liquid caustic soda, be adjusted to PH=6-7, then stir 1-2h;
3. reactions steps: add cupric sulfate pentahydrate 125kg-500kg, at 90-98 ℃ of reaction 1.7-3h;
4. product separation: be down to room temperature, centrifugal, 90 ℃ dry, obtains 2-pyridine carboxylic acid copper blue powder.
2. the industrialized process for preparing of 2-pyridine carboxylic acid copper according to claim 1, is characterized in that: described step 3. in, cupric sulfate pentahydrate is incorporated as in batches and adds, and within 15 minutes, adds once, each 25kg-100kg.
3. according to the industrialized process for preparing of the 2-pyridine carboxylic acid copper described in the arbitrary claim of claim 1-3, it is characterized in that: described 2-pyridine carboxylic acid Chun Du≤99%, cupric sulfate pentahydrate Chun Du≤98%.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113016944A (en) * | 2021-04-29 | 2021-06-25 | 正百生物科技(江门)有限公司 | Feed additive containing composite organic trace elements and preparation method thereof |
| CN114591511A (en) * | 2022-03-28 | 2022-06-07 | 陕西科技大学 | Copper-based coordination polymer for simulating natural superoxide dismutase and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007277106A (en) * | 2006-04-03 | 2007-10-25 | Nissan Motor Co Ltd | Porous metal complex, method for producing the same, adsorbent, separating agent, gas adsorbent, and hydrogen adsorbent |
| CN102232472A (en) * | 2010-04-21 | 2011-11-09 | 四川尚元精细化工有限责任公司 | Water-soluble compound used as feed additive and preparation method thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007277106A (en) * | 2006-04-03 | 2007-10-25 | Nissan Motor Co Ltd | Porous metal complex, method for producing the same, adsorbent, separating agent, gas adsorbent, and hydrogen adsorbent |
| CN102232472A (en) * | 2010-04-21 | 2011-11-09 | 四川尚元精细化工有限责任公司 | Water-soluble compound used as feed additive and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| 东梅: "2- 吡啶甲酸铜(II)配合物的合成及晶体结构", 《重庆科技学院学报( 自然科学版)》 * |
| 李清禄，等: "吡啶羧酸与铜( Ⅱ)螯合物的合成及结构表征", 《福建农林大学学报(自然科学版)》 * |
| 蒋云霞，等: "α-吡啶甲酸铜( Ⅱ) 配合物的室温固相合成", 《精细化工》 * |
| 陈强，等: "Relationship between Coordination Structure and Biological Activity of Copper(II) Nicotinate", 《结构化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113016944A (en) * | 2021-04-29 | 2021-06-25 | 正百生物科技(江门)有限公司 | Feed additive containing composite organic trace elements and preparation method thereof |
| CN114591511A (en) * | 2022-03-28 | 2022-06-07 | 陕西科技大学 | Copper-based coordination polymer for simulating natural superoxide dismutase and preparation method and application thereof |
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| CN103613536B (en) | 2015-11-04 |
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Granted publication date: 20151104 Termination date: 20161213 |