CN113979948B - Method for recovering AABI from AABI reduction process mother liquor - Google Patents
Method for recovering AABI from AABI reduction process mother liquor Download PDFInfo
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- CN113979948B CN113979948B CN202111534607.4A CN202111534607A CN113979948B CN 113979948 B CN113979948 B CN 113979948B CN 202111534607 A CN202111534607 A CN 202111534607A CN 113979948 B CN113979948 B CN 113979948B
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- aabi
- mother liquor
- reduction process
- filtering
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- 239000012452 mother liquor Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000011946 reduction process Methods 0.000 title claims abstract description 16
- 238000001914 filtration Methods 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000047 product Substances 0.000 claims abstract description 16
- 239000012535 impurity Substances 0.000 claims abstract description 13
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000000706 filtrate Substances 0.000 claims description 25
- 238000003756 stirring Methods 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 230000001276 controlling effect Effects 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 7
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 239000010413 mother solution Substances 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 abstract description 8
- QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002351 wastewater Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 238000007792 addition Methods 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000004042 decolorization Methods 0.000 abstract 1
- 238000010612 desalination reaction Methods 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000000049 pigment Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of fine chemical engineering, and relates to a method for recovering AABI from AABI reduction process mother liquor, which comprises the steps of mother liquor acid regulation, filtration, decolorization, reduction, dropwise addition, cooling and filtration, wherein waste water is directly subjected to impurity removal and desalination through acid regulation, then a crystallization process is skipped, a small amount of reducing agent is added to reduce oxidized 5-aminobenzimidazolone, then activated carbon is added to decolorize and further remove impurities, then diketene is dropwise added, and the AABI product with low solubility is generated by reaction to precipitate. The process is simple, and can be completed by using AABI normal production equipment without newly adding equipment, so that the cost is reduced; the method can reduce the material loss, improve the yield of the AABI, create higher economic value for enterprises, relieve the pressure caused by treating the waste water in the AABI reduction step to the environment, and reduce the environmental pollution.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a method for recovering AABI from AABI reduction process mother liquor.
Background
AABI (5-acetoacetamino benzimidazolone), white-like powder, molecular weight 233, melting point > 350 ℃, and is mainly used for synthesizing raw materials of pigment yellow and pigment orange, and the like.
The current production flow for producing AABI in a domestic scale mainly comprises four steps of cyclization, nitration, reduction and acylation, wherein the product of the reduction step is 5-aminobenzimidazolone, a large amount of water is needed to be used as a solvent in the step, the 5-aminobenzimidazolone has larger water solubility, and more 5-aminobenzimidazolone is inevitably dissolved in mother liquor (waste liquor) after the reaction is finished, so that the yield of the product is low and the cost is high. At present, loss is generally reduced through a mode of mother liquor application, but as the reaction flow needs to repeatedly perform acid-base neutralization, salt and other impurities in the mother liquor are increased more and more along with the increase of application batches, the purity of products is also lower and more, the application times are limited in order to ensure the quality of the products, and the dissolved 5-aminobenzimidazolone in the mother liquor reaching the application times is often recovered by using a traditional recovery method due to the fact that the salt and the impurities are high in content, the purity is low, the oxidation phenomenon is serious, the production and the use cannot be directly performed, the refining cost is high, and the waste is not avoided, so that the mother liquor can only be treated as waste water, and the cost is wasted.
Disclosure of Invention
The invention aims to provide a method for recovering AABI from AABI reduction process mother liquor.
The technical scheme adopted for solving the technical problems is as follows: a method for recovering AABI from an AABI reduction process mother liquor, comprising the steps of:
1) Acid regulation of mother solution: adding phosphoric acid into AABI reduction process mother liquor at normal temperature, regulating pH value to 4-4.5, stirring at normal temperature, maintaining the temperature to separate out impurities and salt sufficiently, and maintaining the temperature at 35 ℃ for 15-20min;
2) And (3) filtering: filtering at normal temperature to remove impurities and salt, wherein the filtering temperature is not higher than 35 ℃;
3) Decoloring and reducing: adding reducing agent, antioxidant and active carbon into the filtered filtrate, heating to 90-95deg.C under stirring, maintaining the temperature for 25-30min, filtering to remove active carbon, and collecting filtrate;
4) Dropwise adding: controlling the temperature of the filtrate in the step 3) to be 80-85 ℃, dropwise adding diketene at a constant speed under stirring, and stirring and preserving heat for 30min after the dropwise adding is finished;
5) Cooling and filtering: cooling to a temperature less than 45 ℃, filtering to obtain an AABI wet product, and drying to obtain an AABI dry product.
Further, the phosphoric acid in the step 1) is 85% phosphoric acid.
Further, the reducing agent added in the step 3) is sodium hydrosulfite, and the antioxidant is sodium hydrosulfite.
Further, the addition amount of the reducing agent, the antioxidant and the activated carbon in the step 3) is as follows: every 1m 3 1.6kg of reducing agent, 5kg of antioxidant and 4kg of active carbon are added into the mother liquor of the reduction process.
Further, the amount of diketene added in the step 4) is 1m 3 43kg of diketene is added into the mother liquor of the reduction process.
The invention has the following beneficial effects: according to the invention, acid is regulated to directly remove impurities and salts from wastewater, then a crystallization process is skipped, a small amount of reducing agent is added to reduce oxidized 5-aminobenzimidazolone, activated carbon is added to decolorize and further remove impurities, then diketene is dripped to react to generate AABI product with low solubility to precipitate. The invention has simple process, can be completed by using AABI normal production equipment, does not need newly added equipment, and reduces the cost; the method can reduce the material loss, improve the yield of the AABI, create higher economic value for enterprises, relieve the pressure caused by treating the waste water in the AABI reduction step to the environment, and reduce the environmental pollution.
Detailed Description
The following are specific examples of the present invention, and the technical solutions of the present invention are further described, but the scope of the present invention is not limited to these examples. All changes and equivalents that do not depart from the gist of the invention are intended to be within the scope of the invention.
Example 1
600ml of AABI reduction step mother liquor was added to a 1000ml flask, followed by 5.5g of 85% strength phosphoric acid, and the pH was adjusted to 4.5; stirring at 33deg.C for about 15min to separate out impurities and salt, filtering with rapid filter paper, and collecting filtrate.
Transferring the filtrate into another 1000ml flask, adding 1.02g sodium hydrosulfite and 3.01g sodium bisulphite, stirring, changing the color of the filtrate from red to yellow, adding 2.5g active carbon, maintaining stirring and heating to 90-95 ℃, preserving heat for 25min, and performing hot filtration by using quick filter paper to obtain pale yellow filtrate; transferring the filtrate into another 1000ml flask, controlling the temperature of the filtrate to be 80-85 ℃, and dropwise adding 26g of diketene at a constant speed under stirring for about 20min; after the dripping is finished, controlling the temperature to be 80-85 ℃ and preserving the heat for 30min; cooling to 44 ℃, filtering by using quick filter paper to obtain AABI wet products, drying to obtain 40.25g dry products, and detecting the purity to be 99.08%.
Example 2
600ml of AABI reduction step mother liquor was added to a 1000ml flask, followed by 5.5g of 85% strength phosphoric acid, and the pH was adjusted to 4.2; stirring at 30deg.C for about 20min to separate out impurities and salt, filtering with rapid filter paper, and collecting filtrate.
Transferring the filtrate into another 1000ml flask, adding 1.01g sodium hydrosulfite and 2.98g sodium bisulphite, stirring, changing the color of the filtrate from red to yellow, adding 2.5g active carbon, maintaining stirring and heating to 90-95 ℃, preserving heat for 30min, and performing hot filtration by using quick filter paper to obtain pale yellow filtrate; transferring the filtrate into another 1000ml flask, controlling the temperature of the filtrate to be 80-85 ℃, and dropwise adding 26g of diketene at a constant speed under stirring for about 22min; after the dripping is finished, controlling the temperature to be 80-85 ℃ and preserving the heat for 30min; cooling to 45deg.C, filtering with rapid filter paper to obtain AABI wet product, oven drying to obtain 41.21g dry product, and detecting purity of 99.12%.
Example 3
600ml of AABI reduction step mother liquor was added to a 1000ml flask, followed by 5.5g of 85% strength phosphoric acid, and the pH was adjusted to 4; stirring at 32deg.C for 18min to separate out impurities and salt, filtering with rapid filter paper, and collecting filtrate.
Transferring the filtrate into another 1000ml flask, adding 1.02g sodium hydrosulfite and 2.99g sodium bisulphite, stirring, changing the color of the filtrate from red to yellow, adding 2.5g active carbon, maintaining stirring and heating to 90-95 ℃, preserving heat for 28min, and performing hot filtration by using quick filter paper to obtain pale yellow filtrate; transferring the filtrate into another 1000ml flask, controlling the temperature of the filtrate to be 80-85 ℃, and dropwise adding 26g of diketene at a constant speed under stirring for about 21min; after the dripping is finished, controlling the temperature to be 80-85 ℃ and preserving the heat for 30min; cooling to 43 ℃ and filtering with a quick filter paper to obtain an AABI wet product, drying to obtain 42.01g of a dry product, and detecting the purity to be 99.11%.
The present invention is not limited to the above embodiments, and any person who can learn the structural changes made under the teaching of the present invention can fall within the scope of the present invention if the present invention has the same or similar technical solutions.
The technology, shape, and construction parts of the present invention, which are not described in detail, are known in the art.
Claims (4)
1. A method for recovering AABI from an AABI reduction process mother liquor, comprising the steps of:
1) Acid regulation of mother solution: adding phosphoric acid into AABI reduction process mother liquor at normal temperature, regulating pH value to 4-4.5, stirring at normal temperature, maintaining the temperature to separate out impurities and salt sufficiently, and maintaining the temperature at 35 ℃ for 15-20min;
2) And (3) filtering: filtering at normal temperature to remove impurities and salt, wherein the filtering temperature is not higher than 35 ℃;
3) Decoloring and reducing: adding sodium hydrosulfite as a reducing agent and sodium hydrosulfite as an antioxidant into the filtered filtrate, stirring, changing the color of the filtrate from red to yellow, adding active carbon, heating to 90-95 ℃ under stirring, preserving heat for 25-30min, filtering the active carbon, and taking the filtrate;
4) Dropwise adding: controlling the temperature of the filtrate in the step 3) to be 80-85 ℃, dropwise adding diketene at a constant speed under stirring, and stirring and preserving heat for 30min after the dropwise adding is finished;
5) Cooling and filtering: cooling to a temperature less than 45 ℃, filtering to obtain an AABI wet product, and drying to obtain an AABI dry product.
2. The method for recovering AABI from an AABI reduction process mother liquor of claim 1, wherein said phosphoric acid in step 1) is 85% phosphoric acid.
3. The method for recovering AABI from an AABI reduction process mother liquor according to claim 1, wherein the reducing agent, antioxidant and activated carbon are added in the step 3) in the following amounts: 1.6kg of reducing agent, 5kg of antioxidant and 4kg of active carbon are added into each 1m of mother liquor of the reduction process.
4. The method for recovering AABI from an AABI reduction process mother liquor of claim 1, wherein said amount of diketene added in step 4) is 43kg per 1m of reduction process mother liquor.
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| CN202111534607.4A CN113979948B (en) | 2021-12-15 | 2021-12-15 | Method for recovering AABI from AABI reduction process mother liquor |
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| CN101307023A (en) * | 2008-05-23 | 2008-11-19 | 东营市天正化工有限公司 | Production process of 5-acetyl acetamino benzimidazolone |
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| CN110845424A (en) * | 2019-12-11 | 2020-02-28 | 山东汇海医药化工有限公司 | Preparation method of 5-acetoacetylaminobenzimidazolone |
| CN113277983A (en) * | 2021-04-13 | 2021-08-20 | 东营市天正化工有限公司 | Treatment method of 5-aminobenzimidazole ketone mother liquor |
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2021
- 2021-12-15 CN CN202111534607.4A patent/CN113979948B/en active Active
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