CN109336831B - Method for recovering triazine ring from triazine ring wastewater - Google Patents
Method for recovering triazine ring from triazine ring wastewater Download PDFInfo
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- CN109336831B CN109336831B CN201811405704.1A CN201811405704A CN109336831B CN 109336831 B CN109336831 B CN 109336831B CN 201811405704 A CN201811405704 A CN 201811405704A CN 109336831 B CN109336831 B CN 109336831B
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- triazine ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
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- Removal Of Specific Substances (AREA)
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Abstract
The invention relates to a method for recovering triazine ring from triazine ring wastewater, in the presence of a catalyst, the wastewater is subjected to reduced pressure distillation to remove redundant moisture, a crude triazine ring product is obtained after suction filtration, and the crude triazine ring product is subjected to reverse regulation treatment to obtain a finished product of triazine ring, wherein the catalyst used in the distillation process is β -diketone, and can effectively inhibit the decomposition of triazine ring.
Description
Technical Field
The invention relates to the technical field of chemical intermediate product recovery, in particular to a method for recovering triazine ring from triazine ring wastewater.
Background
Ceftriaxone is the first semi-synthetic broad-spectrum long-acting cephalosporin, has been listed in medical insurance lists due to its broad-spectrum, high-efficiency and low-toxicity characteristics, is the antibiotic with the largest consumption in China at present, and plays a very important role in the national health industry. The production of the cephalosporin depends on a high-quality cephalosporin medical intermediate, and the triazine ring is a key medical intermediate for synthesizing the ceftriaxone, so the improvement of the production technology and the product quality of the triazine ring is an important driving force for promoting the development of the ceftriaxone.
At present, the existing triazine ring production technology in China has complex process, more side reactions and small production scale, so the yield is generally low. Meanwhile, along with the production of triazine ring, a large amount of refined wastewater containing triazine ring is generated, the wastewater contains non-recovered triazine ring products, and meanwhile, the triazine ring wastewater is strong in acidity and has obvious corrosion effect on equipment, and the wastewater can be treated by MVR only by adjusting the wastewater to be neutral. In addition, since these waste waters contain non-recovered triazine ring products, if they are directly treated as waste waters, they will also cause waste of resources.
Disclosure of Invention
The invention aims to provide a method for recovering triazine ring from triazine ring wastewater, which has low requirement on equipment, high recovery rate of triazine ring and reduced environmental pollution.
The technical scheme adopted by the invention for solving the technical problems is as follows: a method for recovering triazine ring from triazine ring wastewater, comprising the following steps:
(1) and (3) reduced pressure distillation: adding caustic soda flakes into the triazine ring wastewater to adjust the pH value of the solution, then adding a catalyst, and starting reduced pressure distillation;
(2) and (3) suction filtration: after the reduced pressure distillation is finished, carrying out suction filtration to obtain a crude triazine ring product;
(3) activated carbon decolorization: dissolving the crude triazine ring product with water, adding liquid alkali to adjust the pH value of the solution, heating, adding activated carbon to decolor, and keeping the temperature;
(4) and (3) hot suction filtration: carrying out hot suction filtration after heat preservation;
(5) adjusting the pH value: adjusting the pH value of the filtrate by using hydrochloric acid;
(6) cooling and suction filtration: cooling to 10-20 deg.C, and vacuum filtering;
(7) drying: drying for 1-2h to obtain the finished triazine ring product.
Specifically, in the step (1), the pH value of the solution is adjusted to 4-6 by using the caustic soda flakes, the catalyst is β -diketone, the using amount of the catalyst is 0.1% of the mass of the triazine ring wastewater, and the vacuum degree of reduced pressure distillation is-0.08 MPa.
Specifically, the suction filtration temperature in the step (2) is 55-65 ℃.
Specifically, the pH value of the solution is adjusted to 3-4 by adding liquid alkali in the step (3), the adding amount of the activated carbon is 5% of the mass of the crude triazine ring product, the heat preservation temperature of the activated carbon is 70-90 ℃, and the heat preservation time is 1-3 h.
Specifically, the hot suction filtration temperature in the step (4) is 60-70 ℃.
Specifically, in the step (5), hydrochloric acid is used for adjusting the pH value of the solution to 0.5-1.0.
The invention has the following beneficial effects: according to the invention, by selecting a proper catalyst, the decomposition of the triazine ring can be effectively inhibited, and the triazine ring is recovered from the triazine ring wastewater, so that the yield of the triazine ring can be improved, a higher economic value is created for enterprises, the pressure of the treatment of the triazine ring wastewater on the environment can be relieved, and the environmental pollution is reduced.
Detailed Description
The following are specific examples of the present invention and further describe the technical solutions of the present invention, but the scope of the present invention is not limited to these examples. All changes, modifications and equivalents that do not depart from the spirit of the invention are intended to be included within the scope thereof.
Example 1
A method for recovering triazine ring from triazine ring wastewater, comprising the following steps:
(1) vacuum distillation, namely adding caustic soda flakes into the triazine ring wastewater to adjust the pH value of the solution to be 5, then adding β -diketone which accounts for 0.1 percent of the mass of the triazine ring wastewater, and starting vacuum distillation at the vacuum degree of-0.08 MPa;
(2) and (3) suction filtration: after the reduced pressure distillation is finished, carrying out suction filtration at 60 ℃ to obtain a crude triazine ring product;
(3) activated carbon decolorization: dissolving the crude triazine ring product with water, adding liquid alkali to adjust the pH value of the solution to 3.5, heating to 70-90 ℃, adding active carbon accounting for 5% of the mass of the crude triazine ring product to decolor, and keeping the temperature for 3 hours;
(4) and (3) hot suction filtration: carrying out hot suction filtration at 70 ℃ after heat preservation;
(5) adjusting the pH value: adjusting the pH value of the filtrate to 1.0 by hydrochloric acid;
(6) cooling and suction filtration: cooling to 10 ℃ and filtering;
(7) drying: and drying for 2h to obtain a finished triazine ring product. The recovery rate is 0.72%, the product purity is 99.7234%, the content is 98.92%, and the melting point is 248.2-248.4 ℃.
Example 2
A method for recovering triazine ring from triazine ring wastewater, comprising the following steps:
(1) vacuum distillation, namely adding caustic soda flakes into the triazine ring wastewater to adjust the pH value of the solution to be 4, then adding β -diketone which accounts for 0.1 percent of the mass of the triazine ring wastewater, and starting vacuum distillation at the vacuum degree of-0.08 MPa;
(2) and (3) suction filtration: after the reduced pressure distillation is finished, carrying out suction filtration at 55 ℃ to obtain a crude triazine ring product;
(3) activated carbon decolorization: dissolving the crude triazine ring product with water, adding liquid alkali to adjust the pH value of the solution to 4, heating to 70-90 ℃, adding active carbon accounting for 5% of the mass of the crude triazine ring product to decolor, and keeping the temperature for 2 hours;
(4) and (3) hot suction filtration: carrying out hot suction filtration at 60 ℃ after heat preservation;
(5) adjusting the pH value: adjusting the pH value of the filtrate to 0.5 by hydrochloric acid;
(6) cooling and suction filtration: cooling to 20 ℃ and filtering;
(7) drying: and drying for 1.5h to obtain a finished triazine ring product. The recovery rate is 0.79%, the product purity is 99.7615%, the content is 99.13%, and the melting point is 249.3-249.5 ℃.
Example 3
A method for recovering triazine ring from triazine ring wastewater, comprising the following steps:
(1) vacuum distillation, namely adding caustic soda flakes into the triazine ring wastewater to adjust the pH value of the solution to be 6, then adding β -diketone which accounts for 0.1 percent of the mass of the triazine ring wastewater, and starting vacuum distillation at the vacuum degree of-0.08 MPa;
(2) and (3) suction filtration: after the reduced pressure distillation is finished, carrying out suction filtration at 65 ℃ to obtain a crude triazine ring product;
(3) activated carbon decolorization: dissolving the crude triazine ring product with water, adding liquid alkali to adjust the pH value of the solution to 3.5, heating to 70-90 ℃, adding active carbon accounting for 5% of the mass of the crude triazine ring product to decolor, and keeping the temperature for 1 h;
(4) and (3) hot suction filtration: carrying out hot suction filtration at 65 ℃ after heat preservation;
(5) adjusting the pH value: adjusting the pH value of the filtrate to 0.8 by hydrochloric acid;
(6) cooling and suction filtration: cooling to 15 ℃ and carrying out suction filtration;
(7) drying: and drying for 1h to obtain a finished triazine ring product. The recovery rate is 0.77%, the product purity is 99.7458%, the content is 99.25%, and the melting point is 248.9-249.1 ℃.
Example 4
A method for recovering triazine ring from triazine ring wastewater, comprising the following steps:
(1) vacuum distillation, namely adding caustic soda flakes into the triazine ring wastewater to adjust the pH value of the solution to 5.5, then adding β -diketone which accounts for 0.1 percent of the mass of the triazine ring wastewater, and starting vacuum distillation at the vacuum degree of-0.08 MPa;
(2) and (3) suction filtration: after the reduced pressure distillation is finished, carrying out suction filtration at 60 ℃ to obtain a crude triazine ring product;
(3) activated carbon decolorization: dissolving the crude triazine ring product with water, adding liquid alkali to adjust the pH value of the solution to 3, heating to 70-90 ℃, adding active carbon accounting for 5% of the mass of the crude triazine ring product to decolor, and keeping the temperature for 3 hours;
(4) and (3) hot suction filtration: carrying out hot suction filtration at 67 ℃ after heat preservation;
(5) adjusting the pH value: adjusting the pH value of the filtrate to 0.7 by hydrochloric acid;
(6) cooling and suction filtration: cooling to 15 ℃ and carrying out suction filtration;
(7) drying: and drying for 2h to obtain a finished triazine ring product. The recovery rate is 0.76%, the product purity is 99.7563%, the content is 99.07%, and the melting point is 249.2-249.4 ℃.
Claims (3)
1. A method for recovering triazine ring from triazine ring wastewater is characterized by comprising the following steps:
(1) vacuum distillation, namely adding caustic soda flakes into the triazine ring wastewater to adjust the pH value of the solution, then adding a catalyst to start vacuum distillation, wherein the pH value of the caustic soda flakes is adjusted to be 4-6, the catalyst is β -diketone, the dosage of the catalyst is 0.1 percent of the mass of the triazine ring wastewater, and the vacuum degree of the vacuum distillation is-0.08 Mpa;
(2) and (3) suction filtration: after the reduced pressure distillation is finished, carrying out suction filtration to obtain a crude triazine ring product;
(3) activated carbon decolorization: dissolving the crude triazine ring product with water, adding liquid alkali to adjust the pH value of the solution to 3-4, then heating, adding activated carbon to decolor, and keeping the temperature; the adding amount of the activated carbon is 5 percent of the mass of the crude triazine ring product, the heat preservation temperature of the activated carbon is 70-90 ℃, and the heat preservation time is 1-3 hours;
(4) and (3) hot suction filtration: carrying out hot suction filtration after heat preservation;
(5) adjusting the pH value: adjusting the pH value of the filtrate to 0.5-1.0 by hydrochloric acid;
(6) cooling and suction filtration: cooling to 10-20 deg.C, and vacuum filtering;
(7) drying: drying for 1-2h to obtain the finished triazine ring product.
2. The method for recovering triazine ring from triazine ring-containing wastewater as claimed in claim 1, wherein the suction filtration temperature in the step (2) is 55 to 65 ℃.
3. The method for recovering triazine ring from triazine ring-containing wastewater as claimed in claim 1, wherein the temperature of the hot suction filtration in the step (4) is 60 to 70 ℃.
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| CN201811405704.1A CN109336831B (en) | 2018-11-23 | 2018-11-23 | Method for recovering triazine ring from triazine ring wastewater |
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| CN109336831B true CN109336831B (en) | 2020-07-28 |
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| CN110950814A (en) * | 2019-12-11 | 2020-04-03 | 山东汇海医药化工有限公司 | Method for recovering 3-mercapto-5-methyl-1, 2, 4-triazole from triazine ring refining wastewater |
| CN110981823B (en) * | 2019-12-27 | 2021-08-03 | 山东汇海医药化工有限公司 | Method for preparing 3-mercapto-5-methyl-1, 2, 4-triazole from triazine ring |
| CN111057017B (en) * | 2019-12-27 | 2021-07-30 | 山东汇海医药化工有限公司 | Method for recovering 3-mercapto-5-methyl-1, 2, 4-triazole from triazine ring cyclization mother liquor |
| CN112209892A (en) * | 2020-10-20 | 2021-01-12 | 山东汇海医药化工有限公司 | Preparation method of high-melting-point triazine ring product |
| CN113735790B (en) * | 2021-09-24 | 2023-03-14 | 山东汇海医药化工有限公司 | Method for recovering triazine ring from triazine ring cyclization mother solution |
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| CN101701012A (en) * | 2009-11-20 | 2010-05-05 | 南通市纳百园化工有限公司 | Method for synthesizing triazine ring |
| CN103224473B (en) * | 2013-05-16 | 2015-04-15 | 黑龙江大学 | Preparation method of triazine ring |
| CN103664812B (en) * | 2013-12-16 | 2015-07-15 | 山东汇海医药化工有限公司 | Preparation method of TTZ (thiotriazinone) |
| CN104177305B (en) * | 2014-08-07 | 2017-09-15 | 山东汇海医药化工有限公司 | The new method of triazine ring is synthesized using mixed solvent |
| CN104387334A (en) * | 2014-10-27 | 2015-03-04 | 河南师范大学 | Synthetic process of 2-amino-4-methoxy-6-methyl s-triazine |
| CN106749063A (en) * | 2016-11-14 | 2017-05-31 | 山东汇海医药化工有限公司 | The method that a kind of self-control organic alkali catalyst of use with Graphene as carrier synthesizes triazine ring |
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Denomination of invention: A method for recovering triazine ring from triazine ring waste water Effective date of registration: 20211130 Granted publication date: 20200728 Pledgee: Dongying Hekou District sub branch of China Post Savings Bank Co.,Ltd. Pledgor: SHANDONG HUIHAI PHARMACEUTICAL& CHEMICAL Co.,Ltd. Registration number: Y2021980013568 |