CN114456106B - Method for recycling nicotinic acid in industrial wastewater - Google Patents
Method for recycling nicotinic acid in industrial wastewater Download PDFInfo
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- CN114456106B CN114456106B CN202011244214.5A CN202011244214A CN114456106B CN 114456106 B CN114456106 B CN 114456106B CN 202011244214 A CN202011244214 A CN 202011244214A CN 114456106 B CN114456106 B CN 114456106B
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- nicotinic acid
- industrial wastewater
- wastewater
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title claims abstract description 147
- 235000001968 nicotinic acid Nutrition 0.000 title claims abstract description 78
- 239000011664 nicotinic acid Substances 0.000 title claims abstract description 78
- 229960003512 nicotinic acid Drugs 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000010842 industrial wastewater Substances 0.000 title claims abstract description 11
- 238000004064 recycling Methods 0.000 title claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002351 wastewater Substances 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 14
- 239000000706 filtrate Substances 0.000 claims abstract description 13
- 239000012065 filter cake Substances 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 238000004090 dissolution Methods 0.000 claims abstract description 6
- 230000001105 regulatory effect Effects 0.000 claims abstract description 5
- 238000001291 vacuum drying Methods 0.000 claims abstract description 5
- 238000009835 boiling Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000000967 suction filtration Methods 0.000 claims description 6
- 239000008213 purified water Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 abstract description 4
- 238000004065 wastewater treatment Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- KFLRWGSAMLBHBV-UHFFFAOYSA-M sodium;pyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CN=C1 KFLRWGSAMLBHBV-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- BOHCMQZJWOGWTA-UHFFFAOYSA-N 3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1 BOHCMQZJWOGWTA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D213/78—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
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a method for recycling nicotinic acid in industrial wastewater, which comprises the steps of concentrating the nicotinic acid wastewater until the content of the nicotinic acid is 100-250g/L, then directly regulating the pH value to 3.0-4.0, directly adding active carbon, adding a certain amount of solvent for dissolution, heating and boiling, filtering while the solution is hot, standing the filtrate to room temperature, filtering the filtrate again, washing a filter cake to obtain a wet product, and vacuum drying at 70-100 ℃ and 0.08-0.10 mpa to obtain high-purity nicotinic acid. The method solves the problems of complex process conditions, low quality of recovered nicotinic acid, low recovery rate, high wastewater treatment cost and the like in the prior art.
Description
Technical Field
The invention belongs to the technical field of wastewater treatment, and particularly relates to a method for recycling nicotinic acid in industrial wastewater.
Background
At present, the recovery methods of nicotinic acid in nicotinic acid wastewater in the prior art mainly comprise a concentration method, a resin adsorption method, a membrane treatment method, a metal ion complexation method, a biochemical treatment method and the like, wherein the more important methods are as follows:
the method comprises the following steps: respectively taking ammonia water and wastewater containing 3-cyanopyridine, wherein the mol ratio of the 3-cyanopyridine to the ammonia water in the wastewater is 1:2-8; pouring the wastewater and ammonia water into a reaction kettle for reaction for 1 to 6 hours under mild pressure; concentrating the reaction solution under reduced pressure to obtain a dry solid; adding water into the dried solid, cleaning and drying, and recycling the filtered aqueous solution; and sublimating the dried solid at 220-230 ℃ to obtain nicotinic acid. In the method, 3-cyanopyridine and nicotinamide in wastewater are hydrolyzed to generate nicotinic acid in the presence of ammonia, and nicotinic acid mother liquor is dried and sublimated to obtain finished product nicotinic acid, which has the defects that the needed raw material ammonia water is toxic, has irritation and corrosiveness to eyes, nose and skin, can suffocate people, has complex whole generation process, and has strict requirements on production conditions and high cost.
The second method is as follows: regulating pH of nicotinic acid wastewater to 5-7, cooling to below 20 ℃, dropwise adding a saturated solution of metal salt into the wastewater, stirring at low temperature, and suction-filtering to obtain a nicotinic acid complex filter cake, and sequentially washing the nicotinic acid complex filter cake with an organic solvent and water; adding water into a nicotinic acid complex filter cake to form slurry, heating, then dropwise adding 30% liquid alkali, regulating the pH value to be more than 10.0, carrying out reflux reaction, cooling to room temperature, and carrying out suction filtration to obtain a sodium nicotinate aqueous solution; adding concentrated sulfuric acid into sodium nicotinate aqueous solution to regulate pH to 3.5, slowly stirring, naturally crystallizing, suction filtering, recrystallizing with methanol, drying to obtain nicotinic acid, which has the defects of complicated production process, high cost and unfavorable mass production operation.
Disclosure of Invention
Aiming at solving the problems of complex process and strict production condition requirements in the prior art, the method aims at providing a method for recovering nicotinic acid in industrial wastewater, and solves the problems of low quality, low recovery rate, high wastewater treatment cost and the like of the recovered nicotinic acid in the prior art.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a method for recovering nicotinic acid in industrial wastewater, which comprises the following steps:
(1) Concentrating: concentrating the nicotinic acid wastewater until the nicotinic acid content is 100-250g/L;
(2) One-step acidification and decoloration: directly regulating the pH value of the nicotinic acid wastewater concentrated in the step (1) to 3.0-4.0, directly adding active carbon, adding a certain amount of solvent for dissolution, heating and boiling, filtering while the solution is hot, and standing the filtrate to room temperature;
(3) Washing: filtering the filtrate in the step (2) again, and washing the filter cake with water to obtain a wet product;
(4) Vacuum drying: and (3) drying the wet product obtained in the step (3) at 70-100 ℃ in vacuum at-0.08 mpa to-0.10 mpa to obtain the high-purity nicotinic acid.
In some embodiments, the method used for concentration in step (1) of the present invention is vacuum heat concentration.
In some embodiments, the agent used to adjust the pH in step (2) of the present invention is hydrochloric acid, and in some more specific embodiments, the hydrochloric acid is used in a mass fraction of 36% -38%. The use of other acids can increase the interference of other elements, have uncontrollable influence on experiments, use hydrochloric acid and increase Cl ions, and can remove the influence of Cl by a water washing method. Hydrochloric acid concentration is low, more water is introduced, so that nicotinic acid is dissolved in water, and the yield of nicotinic acid is affected.
In some embodiments, the mass of the activated carbon added in the step (2) of the present invention accounts for 3-5% of the total mass of the concentrated nicotinic acid, and the total amount of the activated carbon in the present invention must be controlled within the range, if the amount of the activated carbon is small, the decolorizing effect is poor, and the purity of the nicotinic acid is affected. If the amount of activated carbon is large, the amount of nicotinic acid adsorbed on the activated carbon increases, and the yield of nicotinic acid decreases.
In some embodiments, the solvent dissolved in step (2) of the present invention is purified water, and in some more specific embodiments, the amount of solvent used is 10-14 times the mass of niacin. The solvent must be purified water and other solvents introduce impurities into the experiment, interfering with the overall experiment. If the amount of the solvent is small, nicotinic acid cannot be completely dissolved, and the yield of the nicotinic acid is reduced when the nicotinic acid is treated together with the activated carbon during suction filtration. If the amount of the solvent is large, nicotinic acid is excessively dissolved in the filtrate and cannot be extracted, resulting in a decrease in the yield of nicotinic acid.
In some embodiments, the heating to boil in step (2) of the present invention is controlled to boil for 25 to 35 minutes. The heating time is short, the decoloring effect of the activated carbon is poor, and the purity of the nicotinic acid can be influenced. The heating time is long, nicotinic acid is lost, and the yield of the nicotinic acid is reduced.
In some embodiments, the hot suction filtration in step (2) of the present invention means suction filtration while maintaining the temperature at a temperature of not less than 90 ℃.
In some embodiments, the washing with water of step (3) of the present invention is specifically carried out 2-5 times with 3-6 times the mass of the filter cake.
In some embodiments, the vacuum drying conditions in step (4) of the present invention are 70-100 ℃, 0.08mpa to 0.10mpa. The purity of the nicotinic acid can be influenced by the reduction of the temperature and the vacuum degree, the volatilization of a small amount of nicotinic acid can be caused by the increase of the temperature and the vacuum degree, and the yield of the nicotinic acid is reduced.
The invention has the beneficial effects that:
(1) The method of the invention is that after the concentrated wastewater is acidified, active carbon is directly added, and solvent is added for dissolution, uniform mixing and heating, the method reduces the nicotinic acid loss, improves the recovery rate of nicotinic acid, and improves the previous 40% yield to about 60%.
(2) The method improves the color and luster degree of the nicotinic acid by using a one-step acidification decoloration and water washing combination method, improves the purity of the nicotinic acid, and can reach more than 99.6 percent of the purity of the obtained nicotinic acid.
(3) The method disclosed by the invention is simple to operate, does not involve toxic and harmful gas, greatly improves the safety, and is very suitable for industrial treatment.
Drawings
FIG. 1 is a graph of HPLC detection data for purity of niacin product obtained in example 1 of the present invention;
FIG. 2 is a graph of HPLC detection data for purity of niacin product obtained in example 2 of the present invention.
Detailed Description
The following examples facilitate a better understanding of the present invention, but are not intended to limit the same. The experimental methods in the following examples are conventional methods unless otherwise specified. The test materials used in the examples described below, unless otherwise specified, were purchased from conventional biochemical reagent stores.
The nicotinic acid wastewater used in the following examples is generated in the production process of tricyanopyridine, and the essential components thereof include: the nicotinic acid content is about 12000-18000ppm, the nicotinamide content is below 100ppm, and other impurities such as 3-CN, toluene, 3-A, etc. are below 1000 ppm.
Example 1
a. Firstly, 10L of nicotinic acid wastewater is placed in a reaction kettle, and vacuum heating is performed to concentrate until the nicotinic acid content reaches 200g/L.
b. 150g of concentrated wastewater is directly acidified to pH 3.7, active carbon accounting for 5% of the total mass of the concentrated nicotinic acid is directly added, 360g of purified water is added for dissolution, and the mixture is uniformly mixed and heated and boiled for 30min.
c. And (5) filtering while the filtrate is hot to obtain filtrate.
d. The filtrate is stood to room temperature and is filtered by suction.
e. And d, washing the filter cake in the step twice, wherein the water quantity is 4 times of that of the filter cake, and obtaining a wet product E1.
f. The wet product E1 obtained in the step E is dried in vacuum (90 ℃ C., -0.09 mpa) to obtain a high-purity nicotinic acid finished product E2:18.2g.
As shown in table 1 and fig. 1, this example finally obtained high purity niacin with a niacin content of 99.73% with a niacin yield of 60.7%.
[ Table 1 ]
Example 2
a. Firstly, 10L of nicotinic acid wastewater is placed in a reaction kettle, and vacuum heating is performed to concentrate until the nicotinic acid content is 120g/L.
b. Taking 150g of concentrated wastewater, directly acidifying to pH 3.7, directly adding active carbon accounting for 5% of the total mass of the concentrated nicotinic acid, adding 300g of purified water for dissolution, uniformly mixing, and heating and boiling for 30min.
c. And (5) filtering while the filtrate is hot to obtain filtrate.
d. The filtrate is stood to room temperature and is filtered by suction.
e. And d, washing the filter cake in the step twice, wherein the water quantity is 4 times of that of the filter cake, and obtaining a wet product E1.
f. And E, carrying out vacuum drying (90 ℃ C., -0.09 mpa) on the wet product E1 obtained in the step E to obtain a high-purity nicotinic acid finished product E2:11.3g.
As shown in table 2 and fig. 2, this example finally obtained high purity niacin with a niacin content of 99.67% and niacin yield of 62.8%.
[ Table 2 ]
Claims (5)
1. The method for recycling the nicotinic acid in the industrial wastewater is characterized by comprising the following steps of:
(1) Concentrating: concentrating the nicotinic acid wastewater until the nicotinic acid content is 100-250g/L;
(2) One-step acidification and decoloration: directly regulating the pH value of the nicotinic acid wastewater concentrated in the step (1) to 3.0-4.0, directly adding active carbon, adding a certain amount of purified water for dissolution, heating and boiling for 25-35 min, filtering while the solution is hot, and standing the filtrate to room temperature; the reagent used for adjusting the pH is hydrochloric acid; 36-38% of hydrochloric acid; the added active carbon accounts for 3-5% of the total mass of the concentrated nicotinic acid;
(3) Washing: filtering the filtrate in the step (2) again, and washing the filter cake with water to obtain a wet product;
(4) Vacuum drying: and (3) drying the wet product obtained in the step (3) at 70-100 ℃ under the vacuum of-0.08 MPa to-0.10 MPa to obtain the high-purity nicotinic acid.
2. The method for recovering nicotinic acid from industrial wastewater according to claim 1, wherein the concentration in the step (1) is vacuum heating concentration.
3. The method for recovering nicotinic acid from industrial wastewater according to claim 1, wherein the amount of the solvent dissolved in the step (2) is 10 to 14 times the mass of nicotinic acid.
4. The method for recovering nicotinic acid from industrial wastewater according to claim 1, wherein the hot suction filtration in the step (2) means suction filtration while maintaining the temperature at not lower than 90 ℃.
5. The method for recovering nicotinic acid from industrial wastewater according to claim 1, wherein the washing with water in step (3) is specifically carried out 2 to 5 times with 3 to 6 times the mass of the filter cake.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011244214.5A CN114456106B (en) | 2020-11-10 | 2020-11-10 | Method for recycling nicotinic acid in industrial wastewater |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011244214.5A CN114456106B (en) | 2020-11-10 | 2020-11-10 | Method for recycling nicotinic acid in industrial wastewater |
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| CN114456106B true CN114456106B (en) | 2024-01-16 |
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|---|---|---|---|---|
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