CN103224449A - Method for recovering benzoic acid from mother liquor or waste liquid - Google Patents
Method for recovering benzoic acid from mother liquor or waste liquid Download PDFInfo
- Publication number
- CN103224449A CN103224449A CN2013101532148A CN201310153214A CN103224449A CN 103224449 A CN103224449 A CN 103224449A CN 2013101532148 A CN2013101532148 A CN 2013101532148A CN 201310153214 A CN201310153214 A CN 201310153214A CN 103224449 A CN103224449 A CN 103224449A
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- CN
- China
- Prior art keywords
- liquid
- mother liquor
- trichloromethane
- lower floor
- methylene dichloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000007788 liquid Substances 0.000 title claims abstract description 57
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000002699 waste material Substances 0.000 title claims abstract description 22
- 239000012452 mother liquor Substances 0.000 title claims abstract description 21
- 239000005711 Benzoic acid Substances 0.000 title abstract 8
- 235000010233 benzoic acid Nutrition 0.000 title abstract 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000013078 crystal Substances 0.000 claims abstract description 27
- 229960001701 chloroform Drugs 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 20
- 238000002425 crystallisation Methods 0.000 claims abstract description 18
- 230000008025 crystallization Effects 0.000 claims abstract description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 8
- 238000001704 evaporation Methods 0.000 claims abstract description 4
- 230000008020 evaporation Effects 0.000 claims abstract description 4
- 238000000605 extraction Methods 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 12
- 239000006228 supernatant Substances 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 241001473877 Biserrula isolate Species 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 abstract description 8
- 239000002351 wastewater Substances 0.000 abstract description 8
- 238000011282 treatment Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 239000002912 waste gas Substances 0.000 abstract description 2
- 238000004065 wastewater treatment Methods 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 10
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Abstract
The invention relates to the technical field of wastewater treatments in industrial production, and provides a method for recovering benzoic acid from mother liquor or waste liquid. The method comprises: adding dichloromethane or trichloromethane to a benzoic acid-containing mother liquor or a benzoic acid-containing waste liquid, stirring, and carrying out standing layering; separating to obtain the lower layer liquid, adding dichloromethane or trichloromethane to the upper layer liquid to extract, separating to obtain the lower layer liquid, repeating the steps for a plurality of times, and carrying out evaporation crystallization and drying on all the lower layer liquids to obtain a crude crystal; and dissolving the crude crystal into dichloromethane, trichloromethane, ethanol or ethyl acetate, stirring, separating to obtain the lower layer liquid, and carrying out evaporation crystallization and drying to obtain the benzoic acid crystal. With the method, organic acid content in the mother liquor or the waste liquid is reduced so as to reduce difficulty of the next waste liquid treatment; the pure benzoic acid is recovered from the mother liquor or the waste liquid so as to change waste into treasure; wastewater and waste gas are not generated, and dichloromethane and ethanol can be completely recycled; and purity of the obtained benzoic acid is more than 95%, and a benzoic acid recovery rate in the mother liquor or the waste liquid can be more than 85%.
Description
?
Technical field
The present invention relates to technical field of waste water processing in the industrial production, particularly a kind ofly from mother liquor or waste liquid, reclaim benzoic method.
Background technology
Phenylformic acid is industries such as chemical industry, medicine organic monoacids commonly used, and its derivative is used for industries such as medical treatment, food.No matter phenylformic acid is used for reactant or catalyzer, can there be the part phenylformic acid in the waste water after the use.Cause waste water to utilize again.Moreover the phenylformic acid price comparison is expensive, causes waste to a certain extent.
The patent No. is 200810019660.9, name is called the Chinese patent of " phenol in the P-hydroxybenzoic acid processing wastewater and the recovery and treatment method of P-hydroxybenzoic acid ", disclose and a kind ofly the P-hydroxybenzoic acid processing wastewater has been extracted, reclaimed wherein phenol and P-hydroxybenzoic acid simultaneously with extraction agent; Described extraction agent is: trioctylamine, tbp, dimethylbenzene or n-Octanol, or two or more mixture wherein; Extraction liquid is stripped with alkaline substance solution, and described alkaline matter is selected from: potassium hydroxide, sodium hydroxide or aqua ammonia; Strip liquor returns production technique and carries out carboxylation reaction.In the waste water rate of recovery of P-hydroxybenzoic acid and phenol all near 100%, the COD clearance reaches 98.9%.But the extraction agent component complexity of using, volatile, the smell is awful, toxicity is bigger, in the removal process loss big, the operator is also easily caused damage.
Summary of the invention
For solve above phenylformic acid reclaim in extraction agent select complexity for use and the problem of certain harm arranged, the invention provides a kind of use healthy extraction agent, the rate of recovery high from mother liquor or waste liquid, reclaim benzoic method.
The present invention is achieved by the following measures:
A kind ofly from mother liquor or waste liquid, reclaim benzoic method, may further comprise the steps:
A. in containing benzoic mother liquor or waste liquid, add methylene dichloride or trichloromethane, stir standing demix;
B. isolate lower floor's liquid, add methylene dichloride or chloroform extraction in the supernatant liquid, isolate lower floor's liquid, repeat this process several times, collect all lower floor's liquid, evaporative crystallization, drying obtains coarse crystal;
C. the coarse crystal that step b is obtained is dissolved in methylene dichloride, trichloromethane, ethanol or the ethyl acetate, stirs, and isolates lower floor's liquid, and with isolated liquid evaporation crystallization, drying obtains the phenylformic acid crystal.
Described method, the volume ratio of methylene dichloride or trichloromethane and mother liquor or waste liquid is 1-1.5:1 among the step a.
Described method, the mass ratio of coarse crystal and methylene dichloride, trichloromethane, ethanol or ethyl acetate is 1:5-10 among the step c.
Described method is filtered earlier after stirring among described step a and the step c.
Described method adds methylene dichloride or chloroform extraction in the supernatant liquid among the step b, methylene dichloride or trichloromethane are 1-1.5 times of supernatant liquid volume.
Described method, the evaporative crystallization temperature among step b and the step c is 20-100 ℃.
Described method, drying conditions is 20 ℃-25 ℃ among step b and the step c ,-0.1MPa.
Described method, the methylene dichloride of evaporative crystallization among recycling step b and the step c.
Beneficial effect of the present invention:
The inventive method has reduced organic acid content in mother liquor or the waste liquid, has reduced the difficulty of next step liquid waste disposal; Be recovered to pure phenylformic acid in from mother liquor or waste liquid, turn waste into wealth; Do not produce waste water and waste gas, the recycling fully of methylene dichloride and ethanol; The phenylformic acid purity that obtains is more than 95%, and the benzoic rate of recovery reaches 85%-99% in mother liquor or the waste liquid.
Embodiment
For a better understanding of the present invention, further specify below in conjunction with specific embodiment.
Embodiment 1:
A. benzoated trade effluent 100g(is detected and wherein contains phenylformic acid 0.20g) join in the reactor, add the 150g methylene dichloride, stir 20-30min.Whipped state filters down, and the mechanical impurity in the system is filtered out, and collects filtrate, and filtrate is left standstill phase-splitting;
B. isolate lower floor's liquid, in supernatant liquid, add the 100g dichloromethane extraction, stir 20-30min, leave standstill phase-splitting, isolate lower floor's liquid, repeat this process three times, collect all lower floor's liquid, put into evaporative crystallizer, 40 ℃ of evaporative crystallizations, 20 ℃-25 ℃,-0.1MPa vacuum-drying, obtain coarse crystal, methylene dichloride will be collected, and is used for the next batch solvent and uses;
C. the coarse crystal that step b is obtained is dissolved in the ethanol, and coarse crystal and ethanol mass ratio are 1:5, fully stir 40-60min, filter and collect filtrate, standing separation goes out lower floor's organic phase, with isolated organic phase evaporative crystallization, 20 ℃-25 ℃ ,-0.1MPa vacuum-drying obtains the phenylformic acid crystal.Detecting purity is 96.55%, and the rate of recovery is 86.6%.
Embodiment 2:
A. benzoated mother liquor 100g(is detected and wherein contains phenylformic acid 0.25g) join in the reactor, add the 100g methylene dichloride, stir 20-30min.Whipped state filters down, and the mechanical impurity in the system is filtered out, and collects filtrate, and filtrate is left standstill phase-splitting;
B. isolate lower floor's liquid, in supernatant liquid, add the 150g ethyl acetate extraction, stir 20-30min, leave standstill phase-splitting, isolate lower floor's liquid, repeat this process four times, collect all lower floor's liquid, put into evaporative crystallizer, 60 ℃ of evaporative crystallizations, 20 ℃-25 ℃,-0.1MPa vacuum-drying, obtain coarse crystal, methylene dichloride will be collected, and is used for the next batch solvent and uses;
C. the coarse crystal that step b is obtained is dissolved in the ethanol, and coarse crystal and ethanol mass ratio are 1:10, fully stir 40-60min, filter and collect filtrate, standing separation goes out lower floor's organic phase, with isolated organic phase evaporative crystallization, 20 ℃-25 ℃ ,-0.1MPa vacuum-drying obtains the phenylformic acid crystal.Detecting purity is 96.55%, and the rate of recovery is 88.9%.
Embodiment 3:
A. benzoated mother liquor 100g(is detected and wherein contains phenylformic acid 0.32g) join in the reactor, add the 150g trichloromethane, stir 20-30min.Whipped state filters down, and the mechanical impurity in the system is filtered out, and collects filtrate, and filtrate is left standstill phase-splitting;
B. isolate lower floor's liquid, in supernatant liquid, add the 150g chloroform extraction, stir 20-30min, leave standstill phase-splitting, isolate lower floor's liquid, repeat this process five times, collect all lower floor's liquid, put into evaporative crystallizer, 60 ℃ of evaporative crystallizations, 20 ℃-25 ℃,-0.1MPa vacuum-drying, obtain coarse crystal, trichloromethane will be collected, and is used for the next batch solvent and uses;
C. the coarse crystal that step b is obtained is dissolved in the ethanol, and coarse crystal and ethanol mass ratio are 1:8, fully stir 40-60min, filter and collect filtrate, standing separation goes out lower floor's organic phase, with isolated organic phase evaporative crystallization, 20 ℃-25 ℃ ,-0.1MPa vacuum-drying obtains the phenylformic acid crystal.Detecting purity is 98.05%, and the rate of recovery is 96.45%.
Claims (9)
1. one kind is reclaimed benzoic method from mother liquor or waste liquid, it is characterized in that may further comprise the steps:
A. in containing benzoic mother liquor or waste liquid, add methylene dichloride or trichloromethane, stir standing demix;
B. isolate lower floor's liquid, add methylene dichloride or chloroform extraction in the supernatant liquid, isolate lower floor's liquid, repeat this process several times, collect all lower floor's liquid, evaporative crystallization, drying obtains coarse crystal;
C. the coarse crystal that step b is obtained is dissolved in methylene dichloride, trichloromethane, ethanol or the ethyl acetate, stirs, and isolates lower floor's liquid, and with isolated liquid evaporation crystallization, drying obtains the phenylformic acid crystal.
2. method according to claim 1 is characterized in that the volume ratio of methylene dichloride among the step a or trichloromethane and mother liquor or waste liquid is 1-1.5:1.
3. method according to claim 1 is characterized in that the mass ratio of coarse crystal and methylene dichloride, trichloromethane, ethanol or ethyl acetate is 1:5-10 among the step c.
4. method according to claim 1 is filtered earlier after it is characterized in that stirring among described step a and the step c.
5. method according to claim 1 is characterized in that adding in the supernatant liquid among the step b methylene dichloride or chloroform extraction, and methylene dichloride or trichloromethane are 1-1.5 times of supernatant liquid volume.
6. method according to claim 1 is characterized in that the evaporative crystallization temperature among step b and the step c is 20-100 ℃.
7. method according to claim 1 is characterized in that drying conditions is 20 ℃-25 ℃ among step b and the step c ,-0.1MPa.
8. method according to claim 1 is characterized in that the methylene dichloride of evaporative crystallization among recycling step b and the step c.
9. method according to claim 1 is characterized in that may further comprise the steps:
A. benzoated mother liquor 100g is joined in the reactor, add the 150g trichloromethane, stir 20-30min, whipped state filters down, and the mechanical impurity in the system is filtered out, and collects filtrate, and filtrate is left standstill phase-splitting;
B. isolate lower floor's liquid, in supernatant liquid, add the 150g chloroform extraction, stir 20-30min, leave standstill phase-splitting, isolate lower floor's liquid, repeat this process twice, collect all lower floor's liquid, put into evaporative crystallizer, 60 ℃ of evaporative crystallizations, 20 ℃-25 ℃ ,-0.1MPa vacuum-drying obtains coarse crystal;
C. the coarse crystal that step b is obtained is dissolved in the ethanol, and coarse crystal and ethanol mass ratio are 1:8, fully stir 40-60min, filter and collect filtrate, standing separation goes out lower floor's organic phase, with isolated organic phase evaporative crystallization, 20 ℃-25 ℃ ,-0.1MPa vacuum-drying obtains the phenylformic acid crystal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310153214.8A CN103224449B (en) | 2013-04-28 | 2013-04-28 | A kind of method of recovery of benzoic acid from mother liquor or waste liquid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310153214.8A CN103224449B (en) | 2013-04-28 | 2013-04-28 | A kind of method of recovery of benzoic acid from mother liquor or waste liquid |
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| Publication Number | Publication Date |
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| CN103224449A true CN103224449A (en) | 2013-07-31 |
| CN103224449B CN103224449B (en) | 2015-09-02 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105754A (en) * | 2021-12-02 | 2022-03-01 | 湖北科林博伦新材料有限公司 | Organic sodium salt treatment process and device in toluene oxidation process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6211404B1 (en) * | 1996-09-30 | 2001-04-03 | Nippon Steel Chemical Co., Ltd. | Method of refining benzoic acid |
| CN102701959A (en) * | 2012-06-05 | 2012-10-03 | 山东大学 | Novel method for extracting benzoic acid from TA (Terephthalic Acid) residues |
-
2013
- 2013-04-28 CN CN201310153214.8A patent/CN103224449B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6211404B1 (en) * | 1996-09-30 | 2001-04-03 | Nippon Steel Chemical Co., Ltd. | Method of refining benzoic acid |
| CN102701959A (en) * | 2012-06-05 | 2012-10-03 | 山东大学 | Novel method for extracting benzoic acid from TA (Terephthalic Acid) residues |
Non-Patent Citations (1)
| Title |
|---|
| 张海清等: "PTA装置废渣及废钯的回收利用", 《聚酯工业》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105754A (en) * | 2021-12-02 | 2022-03-01 | 湖北科林博伦新材料有限公司 | Organic sodium salt treatment process and device in toluene oxidation process |
| CN114105754B (en) * | 2021-12-02 | 2024-02-27 | 湖北科林博伦新材料有限公司 | Organic sodium salt treatment process and device in toluene oxidation process |
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| Publication number | Publication date |
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| CN103224449B (en) | 2015-09-02 |
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Address after: Shengquan Industrial Park 250204 Shandong city of Ji'nan province Zhangqiu City Diao Town Industrial Development Zone Applicant after: CARBOTANG LTD. Address before: Shengquan Industrial Park 250204 Shandong city of Ji'nan province Zhangqiu City Diao Town Industrial Development Zone Applicant before: JINAN KABOTANG BIOTECHNOLOGY Co.,Ltd. |
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Address after: 250204 Shengquan Industrial Park, Diaozhen Industrial Development Zone, Zhangqiu City, Shandong Province Patentee after: CARBOTANG BIOTECH CO.,LTD. Address before: 250204 Shengquan Industrial Park, Diaozhen Industrial Development Zone, Zhangqiu City, Jinan City, Shandong Province Patentee before: CARBOTANG LTD. |
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Address after: 250204 Diaozhen Street Chemical Industrial Park, Zhangqiu District, Jinan City, Shandong Province Patentee after: Jinan Carbotang Biotech Co.,Ltd. Address before: 250204 Shengquan Industrial Park, Diaozhen Industrial Development Zone, Zhangqiu City, Shandong Province Patentee before: CARBOTANG BIOTECH CO.,LTD. |