CN116573990A - Method for recovering resorcinol from waste activated carbon generated in 2, 6-dihydroxybenzoic acid production - Google Patents
Method for recovering resorcinol from waste activated carbon generated in 2, 6-dihydroxybenzoic acid production Download PDFInfo
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- CN116573990A CN116573990A CN202310550554.8A CN202310550554A CN116573990A CN 116573990 A CN116573990 A CN 116573990A CN 202310550554 A CN202310550554 A CN 202310550554A CN 116573990 A CN116573990 A CN 116573990A
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- China
- Prior art keywords
- activated carbon
- resorcinol
- waste activated
- dihydroxybenzoic acid
- filtrate
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims abstract description 86
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 71
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 239000002699 waste material Substances 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000000706 filtrate Substances 0.000 claims abstract description 32
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 22
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 22
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000010992 reflux Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 238000005406 washing Methods 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 26
- 238000001816 cooling Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VJNRJWRPWLZCIG-UHFFFAOYSA-N [K].OC1=CC(O)=CC=C1 Chemical compound [K].OC1=CC(O)=CC=C1 VJNRJWRPWLZCIG-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- GDQLHKHFHWLXES-UHFFFAOYSA-N 1,5-dichlorocyclohexa-2,4-diene-1-carbaldehyde Chemical compound ClC1=CC=CC(Cl)(C=O)C1 GDQLHKHFHWLXES-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000005588 Oxadiazon Substances 0.000 description 1
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of resorcinol recovery, and provides a method for recovering resorcinol from waste activated carbon generated in the production of 2, 6-dihydroxybenzoic acid, which comprises the following steps: s1, mixing waste activated carbon with water, heating and refluxing, and collecting filtrate; s2, extracting the filtrate to obtain resorcinol; the extractant includes butyl acetate and/or di (2-ethylhexyl) phosphate. By the technical scheme, the problems that the residual resorcinol in the waste activated carbon generated in the process of producing the 2, 6-dihydroxybenzoic acid by using the resorcinol method in the prior art pollutes the environment and the raw material utilization rate is low are solved.
Description
Technical Field
The invention relates to the technical field of resorcinol recovery, in particular to a method for recovering resorcinol from waste activated carbon generated in the production of 2, 6-dihydroxybenzoic acid.
Background
2, 6-dihydroxybenzoic acid is an important intermediate for organic synthesis, and is widely used in the fields of agricultural chemistry, industrial chemistry and the like because of the nature of phenol and aromatic acid. The 2, 6-dihydroxybenzoic acid can be used as a raw material to synthesize a plurality of pesticides, medicines and dyes, such as oxadiazon, pyrimethanil salicylic acid, dipyr and other novel efficient herbicides.
At present, the synthesis method of 2, 6-dihydroxybenzoic acid mainly comprises a resorcinol method, a m-dichlorobenzaldehyde oxidation method, an aromatic acetic acid degradation oxidation method and an aryl beta-diketone terpyridyl ruthenium chloride-visible light double catalytic oxidation method and an enzyme catalytic carboxylation method. The most widely used is the resorcinol method, which is specifically: solid resorcinol and solid potassium carbonate are used as raw materials to form resorcinol potassium salt as a reaction intermediate, and then the resorcinol potassium salt is subjected to gas-solid two-phase reaction under intense stirring and carbon dioxide gas pressure to prepare the 2, 6-dihydroxybenzoic acid.
In the process of producing 2, 6-dihydroxybenzoic acid by a resorcinol method, in order to improve the product yield, activated carbon is added, and after the reaction is finished, resorcinol as a reaction raw material is remained in waste activated carbon, so that the environment is seriously polluted, and the utilization rate of the raw material is low.
Disclosure of Invention
The invention provides a method for recycling resorcinol from waste activated carbon generated in the production of 2, 6-dihydroxybenzoic acid, which solves the problems of environmental pollution and low raw material utilization rate caused by residual resorcinol in the waste activated carbon generated in the production of 2, 6-dihydroxybenzoic acid by a resorcinol method in the related art.
The technical scheme of the invention is as follows:
a method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid comprising the steps of:
s1, mixing waste activated carbon with water, heating and refluxing, and collecting filtrate;
s2, extracting the filtrate to obtain resorcinol;
the extractant includes butyl acetate and/or di (2-ethylhexyl) phosphate.
As a further embodiment, the extractant includes butyl acetate and di (2-ethylhexyl) phosphate.
As a further technical scheme, the mass ratio of the butyl acetate to the di (2-ethylhexyl) phosphate is 2-4:1-3.
As a further technical scheme, the mass ratio of the butyl acetate to the di (2-ethylhexyl) phosphate is 3:2.
As a further technical scheme, the temperature in the S1 is raised to 102-108 ℃ and the mixture is refluxed for 30-50 min.
As a further technical scheme, the mass ratio of the waste activated carbon to the water in the S1 is 1:2-4.
As a further technical scheme, the mass ratio of the filtrate to the extractant in the S2 is 1:0.2-0.3.
As a further technical scheme, the mass ratio of the filtrate to the extractant in the step S2 is 1:0.25.
As a further technical scheme, the method further comprises distillation, washing and drying after the extraction.
As a further technical scheme, the washing is benzene washing.
The working principle and the beneficial effects of the invention are as follows:
1. the invention provides a method for recovering resorcinol from waste active carbon generated in the production of 2, 6-dihydroxybenzoic acid, which comprises the steps of mixing the waste active carbon with water, heating and refluxing to dissolve resorcinol in the waste active carbon and other impurities in the water to form a water phase, and extracting filtrate by butyl acetate and/or di (2-ethylhexyl) phosphate to obtain resorcinol. The resorcinol recovered by the method provided by the invention has high purity and high yield.
2. The invention limits the extractant to butyl acetate and di (2-ethylhexyl) phosphate with the mass ratio of 2-4:1-3, and further improves the purity and yield of the recovered resorcinol.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by one of ordinary skill in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The waste activated carbon of the following example contained resorcinol in an amount of 5.8wt%.
Example 1
Adding 10g of waste activated carbon into 30g of water, refluxing at 102 ℃ for 40min, cooling, filtering, and collecting filtrate; adding butyl acetate into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the butyl acetate is 1:0.25.
Example 2
Adding 10g of waste activated carbon into 30g of water, refluxing at 102 ℃ for 40min, cooling, filtering, and collecting filtrate; adding di (2-ethylhexyl) phosphate into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the di (2-ethylhexyl) phosphate was 1:0.25.
Example 3
Adding 10g of waste activated carbon into 30g of water, refluxing at 102 ℃ for 40min, cooling, filtering, and collecting filtrate; adding an extractant into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the extractant is 1:0.25; the extractant consists of butyl acetate and di (2-ethylhexyl) phosphate in a mass ratio of 3:2.
Example 4
Adding 10g of waste activated carbon into 30g of water, refluxing at 102 ℃ for 40min, cooling, filtering, and collecting filtrate; adding an extractant into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the extractant is 1:0.25; the extractant consists of butyl acetate and di (2-ethylhexyl) phosphate in a mass ratio of 4:1.
Example 5
Adding 10g of waste activated carbon into 30g of water, refluxing at 102 ℃ for 40min, cooling, filtering, and collecting filtrate; adding an extractant into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the extractant is 1:0.25; the extractant consists of butyl acetate and di (2-ethylhexyl) phosphate in a mass ratio of 2:3.
Example 6
Adding 10g of waste activated carbon into 20g of water, refluxing for 50min at 105 ℃, cooling, filtering, and collecting filtrate; adding an extractant into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the extractant is 1:0.3; the extractant consists of butyl acetate and di (2-ethylhexyl) phosphate in a mass ratio of 3:2.
Example 7
Adding 10g of waste activated carbon into 40g of water, refluxing for 30min at 108 ℃, cooling, filtering, and collecting filtrate; adding an extractant into the filtrate, extracting at 40 ℃, collecting an organic phase layer, distilling and collecting fractions at 280 ℃, cooling to obtain a solid, washing the solid with benzene for 2 times, and drying to obtain the solid; the mass ratio of the filtrate to the extractant is 1:0.2; the extractant consists of butyl acetate and di (2-ethylhexyl) phosphate in a mass ratio of 3:2.
The solids obtained in examples 1 to 7 were analyzed for resorcinol content by HPLC, and the yield was calculated according to the following formula.
Yield (%) = (actual mass of solid obtained x resorcinol content)/(theoretical yield of resorcinol x 100)
The results are recorded in table 1.
TABLE 1 resorcinol content and yield
As can be seen from Table 1, the method for recovering resorcinol from waste activated carbon generated in the production of 2, 6-dihydroxybenzoic acid provided by the invention has the purity of over 94.4% and the yield of over 85.6%.
In examples 1 to 2, compared with examples 3 to 5, the extractant in example 1 was butyl acetate, the extractant in example 2 was di (2-ethylhexyl) phosphate, the extractants in examples 3 to 5 were butyl acetate and (2-ethylhexyl) phosphate, and the purity and yield of resorcinol recovered in examples 3 to 5 were higher than those in examples 1 to 2. It is demonstrated that the extraction of resorcinol using butyl acetate and (2-ethylhexyl) phosphate is better than the extraction using either butyl acetate or (2-ethylhexyl) phosphate alone.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (10)
1. A process for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid comprising the steps of:
s1, mixing waste activated carbon with water, heating and refluxing, and collecting filtrate;
s2, extracting the filtrate to obtain resorcinol;
the extractant includes butyl acetate and/or di (2-ethylhexyl) phosphate.
2. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 1 wherein the extractant comprises butyl acetate and di (2-ethylhexyl) phosphate.
3. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 2, wherein the mass ratio of butyl acetate to di (2-ethylhexyl) phosphate is 2 to 4:1 to 3.
4. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 3, wherein the mass ratio of butyl acetate to di (2-ethylhexyl) phosphate is 3:2.
5. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 1, wherein the temperature is raised to 102-108 ℃ in S1 and the reflux is performed for 30-50 min.
6. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as defined in claim 1 wherein the mass ratio of waste activated carbon to water in S1 is 1:2-4.
7. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 1, wherein the mass ratio of filtrate to extractant in S2 is 1:0.2-0.3.
8. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 7 wherein the mass ratio of filtrate to extractant in S2 is 1:0.25.
9. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 1, wherein the extraction is followed by distillation, washing and drying.
10. The method for recovering resorcinol from waste activated carbon produced in the production of 2, 6-dihydroxybenzoic acid as claimed in claim 9 wherein the washing is with benzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310550554.8A CN116573990B (en) | 2023-05-16 | 2023-05-16 | Method for recovering resorcinol from waste activated carbon generated in 2, 6-dihydroxybenzoic acid production |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310550554.8A CN116573990B (en) | 2023-05-16 | 2023-05-16 | Method for recovering resorcinol from waste activated carbon generated in 2, 6-dihydroxybenzoic acid production |
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| CN116573990B CN116573990B (en) | 2024-10-29 |
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