CN116715586A - Recovery method of acid binding agent triethylamine in preparation process of 5-nonylsalicylaldehyde - Google Patents
Recovery method of acid binding agent triethylamine in preparation process of 5-nonylsalicylaldehyde Download PDFInfo
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- CN116715586A CN116715586A CN202310144591.9A CN202310144591A CN116715586A CN 116715586 A CN116715586 A CN 116715586A CN 202310144591 A CN202310144591 A CN 202310144591A CN 116715586 A CN116715586 A CN 116715586A
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- triethylamine
- nonylsalicylaldehyde
- distillation
- binding agent
- recycling
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 title claims abstract description 207
- 238000000034 method Methods 0.000 title claims abstract description 35
- JYWIGMQDJSGOMD-UHFFFAOYSA-N 2-hydroxy-5-nonylbenzaldehyde Chemical compound CCCCCCCCCC1=CC=C(O)C(C=O)=C1 JYWIGMQDJSGOMD-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000002253 acid Substances 0.000 title claims abstract description 16
- 239000011230 binding agent Substances 0.000 title claims abstract description 16
- 238000011084 recovery Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000004821 distillation Methods 0.000 claims abstract description 28
- 238000004064 recycling Methods 0.000 claims abstract description 17
- 239000003513 alkali Substances 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 8
- 238000007599 discharging Methods 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000005191 phase separation Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- FPGVILQTFULZRC-UHFFFAOYSA-N magnesium;2-nonylphenol Chemical compound [Mg].CCCCCCCCCC1=CC=CC=C1O FPGVILQTFULZRC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical group Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000004571 lime Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 abstract description 7
- 238000009776 industrial production Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- MJUVQSGLWOGIOB-UHFFFAOYSA-N 2-[(Z)-hydroxyiminomethyl]-4-nonylphenol Chemical compound OC1=C(C=N/O)C=C(C=C1)CCCCCCCCC MJUVQSGLWOGIOB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- NZYWOLRBUMDENO-UHFFFAOYSA-N 2-nonoxybenzaldehyde Chemical compound CCCCCCCCCOC1=CC=CC=C1C=O NZYWOLRBUMDENO-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NTEUNCALHORCCY-UHFFFAOYSA-N n,n-diethylethanamine;toluene Chemical compound CCN(CC)CC.CC1=CC=CC=C1 NTEUNCALHORCCY-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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 organic synthesis chemical industry, in particular to a method for recycling triethylamine as an acid binding agent in the preparation process of 5-nonylsalicylaldehyde. The method mainly aims at the problems that the recycling efficiency of triethylamine is low and the triethylamine cannot be recycled by an alkali recovery method, and the industrial production cannot be realized by synthesizing 5-nonyl salicylaldehyde by a one-pot method, and provides the following technical scheme: step one: discharging; step two: first distillation; step three: hydrolyzing; step four: separating phases; step five: adjusting the PH; step six: second distillation; step seven: and (3) removing water from the triethylamine. The invention solves the problem of low efficiency of recycling triethylamine by adding alkali once, so that the triethylamine in the process is recycled as much as possible, the industrial production of synthesizing 5-nonylsalicylaldehyde by a one-pot method is realized, the consumption of the triethylamine can be greatly reduced, the economic benefit of the product is improved, the water content of the triethylamine is lower than 0.1 percent, and the recovery rate is higher than 90 percent, thereby being mainly applied to the recycling of the triethylamine.
Description
Technical Field
The invention relates to the technical field of organic synthesis chemical industry, in particular to a method for recycling triethylamine as an acid binding agent in the preparation process of 5-nonylsalicylaldehyde.
Background
The nonyl salicylaldehyde can generate 5-nonyl salicylaldoxime through oximation, and the 5-nonyl salicylaldoxime is a high-efficiency copper extractant and can be used for wet smelting of low-grade copper ores. Triethylamine is expensive and has high toxicity, so that a byproduct triethylamine hydrochloride in the organic synthesis must be recycled. The general 5-nonylsalicylaldehyde is synthesized by adopting a multi-step process, the 5-nonylsalicylaldehyde can be synthesized by a one-pot method, triethylamine is used as an acid binding agent for one-pot reaction to participate in the reaction, and the general alkali recovery method is adopted to recover the triethylamine with low efficiency, so that the recycling of the triethylamine can not be realized, and the industrial production of the 5-nonylsalicylaldehyde synthesized by the one-pot method can not be realized; in view of the above, we particularly propose a method for recovering triethylamine as an acid binding agent in the preparation process of 5-nonylsalicylaldehyde.
Disclosure of Invention
The invention aims at solving the problems that the recovery efficiency of triethylamine by an alkali recovery method in the background technology is low, the recycling of triethylamine can not be realized, and the industrial production of 5-nonylsalicylaldehyde can not be realized by one-pot synthesis, and provides a recovery method of an acid binding agent triethylamine in the preparation process of 5-nonylsalicylaldehyde.
The technical scheme of the invention is as follows: a method for recovering triethylamine as an acid binding agent in the preparation process of 5-nonylsalicylaldehyde comprises the following treatment steps:
step one: discharging: the intermediate product of the complete reaction, namely the magnesium nonylphenol salt, is put into a reaction kettle;
step two: first distillation: heating to the boiling point of triethylamine to start distillation, and evaporating out a mixture of the triethylamine which is not salified and the solvent, wherein the recovery rate is 20-25%;
step three: hydrolysis: adding an inorganic acid solution to carry out hydrolysis reaction to generate 5-nonylsalicylaldehyde and triethylamine salt;
step four: and (3) phase separation: after standing for a certain time, phase separation is started, an oil phase is 5-nonylsalicylaldehyde and an organic solvent, a water phase is triethylamine hydrochloride solution, and the oil phase enters a rectifying system to recover a solvent purification product;
step five: adjusting the pH: adding alkaline substances into the water phase, adjusting the pH to 10-12, and dissociating triethylamine salt into free triethylamine;
step six: second distillation: after the PH is adjusted, carrying out second distillation to recover triethylamine, wherein part of water vapor is carried out in the process of distilling the triethylamine to obtain aqueous triethylamine;
step seven: and (3) removing water from triethylamine: by means of the characteristic that triethylamine is difficult to dissolve in water at a certain temperature, water phase is separated, and triethylamine meeting recycling standards is obtained through a water separator after heating.
Preferably, the solvent in the first distillation in the second step is any one of chlorobenzene, tetrachloroethylene or toluene.
Preferably, the inorganic acid solution added in the third step is any one of sulfuric acid and hydrochloric acid solution.
Preferably, the alkaline substance in the fifth step adopts liquid alkali or solid alkali, including one or more of lime, sodium hydroxide, potassium hydroxide and sodium carbonate.
Preferably, in the step seven, the temperature of the triethylamine for removing water phase is 40-70 ℃.
Preferably, the distillation temperature in the second step is 100-140 ℃, the pressure is normal pressure, and the mixture is put into a receiving tank for recycling by adopting condensation reflux.
Preferably, the distillation temperature in the second step is 100-140 ℃ and the distillation time is 2-3h.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention solves the problem of low efficiency of recycling triethylamine by adding alkali once, and provides a method for recycling triethylamine by secondary distillation, so that the triethylamine in the process is recycled as much as possible, and the industrial production of synthesizing 5-nonyl salicylaldehyde by a one-pot method is realized;
the method can greatly reduce the consumption of the triethylamine, improve the economic benefit of the product, ensure that the water content of the triethylamine is lower than 0.1 percent and ensure that the recovery rate is higher than 90 percent.
Detailed Description
The technical scheme of the invention is further described below with reference to specific embodiments.
Examples
The invention provides a recovery method of an acid binding agent triethylamine in a preparation process of 5-nonylsalicylaldehyde, which comprises the following treatment steps:
step one: discharging: the intermediate product of the complete reaction, namely the magnesium nonylphenol salt, is put into a reaction kettle;
step two: first distillation: heating to the boiling point of triethylamine (125 ℃) to start distillation, and evaporating out the mixture of the triethylamine which is not salified and the solvent, wherein the recovery rate is 20-25%; the distillation temperature in the second step is 100-140 ℃, and the distillation time is 2-3h;
step three: hydrolysis: adding an inorganic acid solution to carry out hydrolysis reaction to generate 5-nonylsalicylaldehyde and triethylamine salt;
step four: and (3) phase separation: after standing for a certain time, phase separation is started, an oil phase is 5-nonylsalicylaldehyde and an organic solvent, a water phase is triethylamine hydrochloride solution, and the oil phase enters a rectifying system to recover a solvent purification product;
step five: adjusting the pH: adding alkaline substances into the water phase, adjusting the pH to 10-12, and dissociating triethylamine salt into free triethylamine;
step six: second distillation: after the PH is adjusted, carrying out second distillation to recover triethylamine, wherein part of water vapor is carried out in the process of distilling the triethylamine to obtain aqueous triethylamine;
step seven: and (3) removing water from triethylamine: by means of the characteristic that triethylamine is difficult to dissolve in water at a certain temperature, water phase is separated, and triethylamine meeting recycling standards is obtained through a water separator after heating.
In the second step, the solvent in the first distillation is any one of chlorobenzene, tetrachloroethylene or toluene.
The inorganic acid solution added in the third step is any one of sulfuric acid and hydrochloric acid solution.
And step five, the alkaline substance adopts liquid alkali or solid alkali, and comprises one or more of lime, sodium hydroxide, potassium hydroxide and sodium carbonate.
In the seventh step, the temperature of the triethylamine for removing water phase is 40-70 ℃.
And step two, the distillation temperature is 100-140 ℃ and the pressure is normal pressure, and the mixture is put into a receiving tank for recycling by adopting condensation reflux.
The following examples are specifically presented:
the magnesium nonylphenol salt is obtained by reacting 714kg of nonylphenol, 1102kg of magnesium chloride, 3500kg of toluene, 1012kg of triethylamine and 500kg of paraformaldehyde for four hours.
The temperature was raised to 125℃and the mixture was distilled once for 2.5 hours to distill about 760kg of a triethylamine toluene mixture.
200kg of 18% hydrochloric acid solution was then added thereto, and hydrolysis reaction was carried out at 70℃for 1 hour.
After the hydrolysis reaction is completed, the reaction solution is subjected to primary phase separation, 200kg of water is added, the phase separation is carried out twice by water washing, and 600kg of sodium hydroxide is added for regulating Ph to 12 after the aqueous solution of the tertiary phase separation is collected.
The aqueous phase was distilled at 95℃for 5 hours and the distillation was stopped when no foam appeared.
The distilled water-containing triethylamine is split-phase at 50 ℃, the weight of the triethylamine is 663kg, and the comprehensive recovery rate of the two steps reaches 92.1 percent.
The above-described embodiments are merely a few preferred embodiments of the present invention, and many alternative modifications and combinations of the above-described embodiments will be apparent to those skilled in the art based on the technical solutions of the present invention and the related teachings of the above-described embodiments.
Claims (7)
1. The recovery method of the acid binding agent triethylamine in the preparation process of the 5-nonylsalicylaldehyde is characterized by comprising the following treatment steps:
step one: discharging: the intermediate product of the complete reaction, namely the magnesium nonylphenol salt, is put into a reaction kettle;
step two: first distillation: heating to the boiling point of triethylamine to start distillation, and evaporating out a mixture of the triethylamine which is not salified and the solvent, wherein the recovery rate is 20-25%;
step three: hydrolysis: adding an inorganic acid solution to carry out hydrolysis reaction to generate 5-nonylsalicylaldehyde and triethylamine salt;
step four: and (3) phase separation: after standing for a certain time, phase separation is started, an oil phase is 5-nonylsalicylaldehyde and an organic solvent, a water phase is triethylamine hydrochloride solution, and the oil phase enters a rectifying system to recover a solvent purification product;
step five: adjusting the pH: adding alkaline substances into the water phase, adjusting the pH to 10-12, and dissociating triethylamine salt into free triethylamine;
step six: second distillation: after the PH is adjusted, carrying out second distillation to recover triethylamine, wherein part of water vapor is carried out in the process of distilling the triethylamine to obtain aqueous triethylamine;
step seven: and (3) removing water from triethylamine: by means of the characteristic that triethylamine is difficult to dissolve in water at a certain temperature, water phase is separated, and triethylamine meeting recycling standards is obtained through a water separator after heating.
2. The method for recovering triethylamine as an acid binding agent in the process of preparing 5-nonylsalicylaldehyde according to claim 1, wherein the solvent in the first distillation in the second step is any one of chlorobenzene, tetrachloroethylene or toluene.
3. The method for recovering triethylamine as an acid binding agent in the process of preparing 5-nonylsalicylaldehyde according to claim 1, wherein the inorganic acid solution added in the third step is any one of sulfuric acid and hydrochloric acid solution.
4. The method for recycling triethylamine as acid-binding agent in the process of preparing 5-nonylsalicylaldehyde according to claim 1, wherein the alkaline substance in the fifth step is liquid alkali or solid alkali, and comprises one or more of lime, sodium hydroxide, potassium hydroxide and sodium carbonate.
5. The method for recovering triethylamine as an acid binding agent in the preparation process of 5-nonylsalicylaldehyde according to claim 1, wherein the water phase separation temperature of triethylamine in the step seven is 40-70 ℃.
6. The method for recycling triethylamine as acid-binding agent in the preparation process of 5-nonylsalicylaldehyde according to claim 1, wherein the distillation temperature in the second step is 100-140 ℃, the pressure is normal pressure, and the mixture is placed into a receiving tank for recycling by adopting condensation reflux.
7. The method for recovering triethylamine as an acid binding agent in the preparation process of 5-nonylsalicylaldehyde according to claim 1, wherein the distillation temperature in the second step is 100-140 ℃, and the distillation time is 2-3h.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310144591.9A CN116715586A (en) | 2023-02-21 | 2023-02-21 | Recovery method of acid binding agent triethylamine in preparation process of 5-nonylsalicylaldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310144591.9A CN116715586A (en) | 2023-02-21 | 2023-02-21 | Recovery method of acid binding agent triethylamine in preparation process of 5-nonylsalicylaldehyde |
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| CN202310144591.9A Pending CN116715586A (en) | 2023-02-21 | 2023-02-21 | Recovery method of acid binding agent triethylamine in preparation process of 5-nonylsalicylaldehyde |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5354920A (en) * | 1992-08-20 | 1994-10-11 | Zeneca Limited | Chemical process for the preparation of a 2-hydroxyarylaldehyde |
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| CN107814723A (en) * | 2017-11-14 | 2018-03-20 | 南通龙翔新材料科技股份有限公司 | The recovery method of triethylamine in a kind of permanent violet preparation process |
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| CN114478263A (en) * | 2022-03-09 | 2022-05-13 | 江苏理文化工有限公司 | Method for recovering triethylamine in vinylene carbonate production |
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-
2023
- 2023-02-21 CN CN202310144591.9A patent/CN116715586A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5354920A (en) * | 1992-08-20 | 1994-10-11 | Zeneca Limited | Chemical process for the preparation of a 2-hydroxyarylaldehyde |
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| CN115160152A (en) * | 2022-08-26 | 2022-10-11 | 开封博凯生物化工有限公司 | Process for recovering triethylamine in triethylamine-containing wastewater |
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