CN110980864A - Method for treating o-nitrophenol production wastewater - Google Patents
Method for treating o-nitrophenol production wastewater Download PDFInfo
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- CN110980864A CN110980864A CN201911355547.2A CN201911355547A CN110980864A CN 110980864 A CN110980864 A CN 110980864A CN 201911355547 A CN201911355547 A CN 201911355547A CN 110980864 A CN110980864 A CN 110980864A
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F9/00—Multistage treatment of water, waste water or sewage
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/34—Organic compounds containing oxygen
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/38—Organic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
- C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2209/00—Controlling or monitoring parameters in water treatment
- C02F2209/08—Chemical Oxygen Demand [COD]; Biological Oxygen Demand [BOD]
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/16—Regeneration of sorbents, filters
Abstract
The invention belongs to the field of chemical wastewater treatment, and particularly relates to a method for treating o-nitrophenol production wastewater. For the waste water generated after the o-nitrochlorobenzene is hydrolyzed to prepare the o-nitrophenol, the method adopts the ethanol as the desorbent, can effectively recover the valuable o-nitrophenol on the premise of utilizing the prior process equipment and basic flow, and does not need to use toxic/expensive chemical reagents, special treatment equipment or extra energy consumption. On the basis, the method can also realize the effective utilization of the recovered o-nitrophenol product, improve the overall process efficiency of preparing o-aminophenol and the recovery efficiency of byproducts such as salts and the like, and avoid the generation of secondary pollution. The invention further provides a method for producing o-aminophenol involving the aforementioned wastewater treatment method.
Description
Technical Field
The invention belongs to the field of chemical wastewater treatment, and particularly relates to a method for treating o-nitrophenol production wastewater.
Background
Ortho-aminophenol, also known as 2-aminophenol, is an organic compound widely used in the manufacture of dyes, pharmaceuticals, and plastic curing agents. The industrial synthesis of o-aminophenol is carried out by taking o-nitrochlorobenzene as initial raw material, hydrolyzing with alkali, neutralizing with acid to obtain o-nitrophenol, and hydrogenating nitro to reduce into amino.
In the whole reaction process, a large amount of chemical wastewater is generated in the production process of the o-nitrophenol serving as the intermediate, and the wastewater is characterized by high salt content, high chroma, high concentration of the nitroaromatic compound, high toxicity, complex components, poor biodegradability and great treatment difficulty (Zhangling and the like, advanced research on the treatment technology of the nitroaromatic compound-containing wastewater, environmental science and technology, 2011, 34(12H), 113). For such wastewater, it is only one aspect of the problem how to remove toxic chemicals (such as unreacted nitrochlorobenzene compounds) and reduce the COD (chemical oxygen demand) and TOC (total organic carbon) of the water body so that the treated water quality reaches the national standard for discharge. The more important factor for industrial production is that the wastewater contains a large amount of reaction aids such as NaCl, o-nitrophenol, and catalyst, which are industrial raw materials with high economic value, and the reaction aids need to be recovered from the wastewater instead of being simply decomposed or discarded. In addition, from the viewpoint of cost control of industrial production, the treatment speed of the waste water from the production of o-nitrophenol should be fast, the treatment capacity should be suitable for industrial large-scale continuous production, and no more energy consumption should be caused by the treatment of the waste water. Therefore, the treatment of the waste water from the production of o-nitrophenol has more prominent characteristics and more serious technical problems than the common domestic waste water, and even other general industrial waste water (such as waste water from paper making, textile and the like).
Various methods for treating waste water from production of o-nitrophenol have been proposed in the prior art, such as microbiological treatment, ultrasonic oxidation (Liuxinyong, research on ultrasonic degradation of low-concentration o-nitrophenol waste water, water purification, 2007, 26(6), 46; CN101462788A), physical adsorption (CN 1562790A; CN 103936207A; CN 1631805A; CN 1490255A; CN1094699A), etc., but these methods have been still in the laboratory due to low treatment efficiency, high energy consumption, or failure to recover useful compounds. Currently, only one of the methods for treating waste water from o-nitrophenol production, which can be really applied in the actual industrial production, is the resin adsorption method (Jianghua et al, research on the treatment of waste water from o-nitrophenol by resin adsorption method, ion exchange and adsorption, 2000, 16(6), 540). The method has the basic principle that the o-nitrophenol in the wastewater is adsorbed by using the adsorptive resin, and then the o-nitrophenol is eluted from the adsorptive resin, so that the o-nitrophenol is recovered. However, this method has the disadvantages that, as the background art document mentioned above, the effluent water contains methanol, so that the COD of the effluent water adsorbed by the resin is extremely high and NaCl cannot be recovered; the NaOH aqueous solution is used as a desorption agent (CN102910757A), the desorption solution needs to be acidified again to obtain o-nitrophenol (instead of the phenol sodium salt), which not only increases the input of chemical raw materials, but also further generates NaCl and other salts which cannot be recycled, and meanwhile, the o-nitrophenol is partially dissolved in the eluent, so that the overall recovery rate is reduced. Also, industrial operations using methanol instead of NaOH aqueous solution as a desorbent, although the aforementioned problems of acidification, salt production, etc. can be avoided, in order to reduce COD and TOC of wastewater, a methanol rectification device is additionally provided to separately recover methanol and o-nitrophenol, which not only increases the equipment investment cost and energy consumption cost, but also methanol as a highly toxic chemical may face problems such as raw material purchase, worker protection, plant management, etc. under increasingly strict policy and supervision, which is not always a promising alternative.
In addition, the final product of the method for treating the waste water from the production of the o-nitrophenol in the prior art can only obtain the non-pure o-nitrophenol mixture, and when the o-nitrophenol mixture is used as a raw material for hydrogenation reduction of the o-aminophenol, additional dissolving, blending and feeding operations are required, so that additional process steps are introduced.
Disclosure of Invention
In order to solve the problems in the prior art, an object of the present invention is to provide an improved method for treating wastewater from o-nitrophenol production, which can effectively recover valuable o-nitrophenol without using toxic/expensive chemical reagents, special treatment equipment or extra energy consumption, on the premise of utilizing the existing process equipment and basic flow for the wastewater generated after the hydrolysis of o-nitrochlorobenzene to prepare o-nitrophenol.
Specifically, the method for treating the o-nitrophenol production wastewater comprises the following steps:
s01, treating the waste water after hydrolysis of the o-nitrochlorobenzene, sending the waste water into resin adsorption equipment for adsorption, and discharging adsorption waste liquid;
s02, desorbing the resin by using a desorbent after the adsorption is saturated to obtain a desorption solution,
the desorbent comprises primarily ethanol.
Further, the ethanol content of the desorbent is above 90% (v/v), preferably above 95% (v/v).
Further, the desorbent is 95% (v/v) ethanol aqueous solution.
Further, the desorbent is industrial alcohol, preferably industrial alcohol having an ethanol content of 96% (v/v) or more and a methanol content of 1% (v/v) or more.
As a preferable scheme, in step S01, the treatment of the wastewater after hydrolysis of ortho-nitrochlorobenzene optionally includes acidification, temperature reduction, sedimentation, water-oil separation and filtration in sequence, and the filtrate is sent to a resin adsorption device.
Further, the resin is selected from one or more of XDA-1, Amberlite XAD-8 (manufactured by Rohm-Haas company, USA), X-5 (manufactured by chemical plant of southern Kao university), preferably XDA-1.
Further, the adsorption equipment is selected from a resin adsorption column, a resin adsorption kettle or a resin adsorption cylinder. The resin adsorption column is a columnar reactor filled with adsorption resin, and the specific form of the resin adsorption column can be determined according to actual factory conditions, for example, a separate adsorption column is adopted to manually feed wastewater/desorption liquid; or the axial two ends of the column are provided with liquid inlet and outlet ports which can be arranged in the production line of o-nitrochlorobenzene/o-nitrophenol/o-aminophenol, and waste liquid or desorption liquid is selectively introduced through a tee joint with a valve at the liquid inlet and outlet ports. The resin adsorption vessel is a reaction vessel with or without stirring equipment, and is charged with an adsorption resin, such as disclosed in CN205838635U or CN 207243516U. The resin adsorption cartridge is a barrel reactor packed with a plurality of layers of adsorption resins, as disclosed in CN208561926U, for example.
Furthermore, the temperature of the adsorption is less than or equal to 25 ℃, and the speed is 1-20BV/h, preferably 2-10 BV/h.
Further, in step S02, when the volume of the discharged adsorption waste liquid reaches 10 to 50 times, preferably 20 times, the volume of the resin, the resin is saturated by adsorption.
As a preferable mode, in the step S02, the desorption temperature is 30-70 ℃ and the desorption rate is 1-20BV/h, preferably 2-10 BV/h. The invention adopts the polar reagent mainly containing ethanol, can perform desorption at a lower temperature than that of the prior art (such as 80 ℃), can prevent the ethanol from volatilizing, and effectively reduces the energy consumption in the desorption process.
Further, in step S02, when the added volume of the desorbent reaches 0.4 to 10 times, preferably 4 times, the volume of the resin, the resin desorption is completed. The desorbed resin can be recycled.
The invention also aims to realize the effective utilization of the recovered o-nitrophenol product, improve the overall process efficiency of preparing o-aminophenol and the recovery efficiency of byproducts such as salts and the like, and avoid the generation of secondary pollution.
Specifically, the method for treating the o-nitrophenol production wastewater further comprises the following steps:
s03, adding the o-nitrophenol and the desorption solution into the analysis solution obtained in the step S02, and feeding the mixture into a hydrogenation reactor.
Further, the method for treating the waste water from the production of the o-nitrophenol comprises the following steps:
s04, after the adsorption waste liquid is oxidized and/or neutralized, evaporating the solution to recover salts.
So far, after the o-nitrophenol wastewater is adsorbed and desorbed, the desorption solution rich in o-nitrophenol is directly sent to a next reaction link (the o-aminophenol is prepared by catalytic hydrogenation), and the valuable intermediate product is utilized to the maximum extent; the adsorption waste liquid is used in distillation-condensation equipment common in industry, such as a heat exchanger, and can recover the adsorbent and salts without or with little investment in additional energy. The whole wastewater treatment process realizes the recycling of all valuable substances and does not discharge high COD and TOC.
Further, in step S03, the desorption solution is fed into the compounding kettle, and the o-nitrophenol and the desorption solution are added. The addition amount of the additional o-nitrophenol and the resolving liquid can be determined by the skilled person according to the specific requirements of the next hydrogenation reduction reaction.
It is another object of the present invention to provide an improved process for the production of an ortho-aminophenol, the process comprising the steps of:
s11, hydrolyzing and neutralizing p-o-nitrochlorobenzene to prepare o-nitrophenol;
s12, treating the wastewater generated in the step S11 by using the wastewater recovery method to recover o-nitrophenol,
s13, preparing the o-aminophenol by hydrogenation reduction using the raw material including the recovered o-nitrophenol obtained in S12.
The method adopts the desorbent containing ethanol as the desorbent in the recovery of the intermediate product, and the desorbed desorption solution can be directly used as a solvent and a raw material for the next hydrogenation reduction without secondary pollution and distillation recovery.
The method for treating the o-nitrophenol production wastewater suitable for large-scale industrial continuous production has the advantages that the method is based on the adsorption resin, utilizes common industrial reaction equipment, realizes the recycling of basically all valuable compounds, does not use toxic reagents in the treatment process, does not consume additional energy, simplifies the process steps of subsequent reaction, and has good industrial application prospect.
Detailed Description
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
In the upstream process, the o-chlorophenol is subjected to alkaline hydrolysis, and the o-nitrophenol production wastewater obtained after treatment is sent into downstream process equipment. Adding hydrochloric acid into the wastewater, adjusting the pH value to be below 3, simultaneously reducing the temperature of the wastewater to 25 ℃, and sending the wastewater into a settling kettle for settling. And (3) carrying out oil-water separation on the settled acidic wastewater, feeding the water phase into a filtering kettle for filtering, recovering filter residues, and feeding the filtrate (namely the acidic waste liquid) out of a liquid storage kettle for later use.
In that
The resin adsorption column is filled with 50mL of XDA-1 macroporous adsorption resin, and a tee joint with a valve is respectively arranged at the liquid inlet and the liquid outlet of the resin adsorption column and is connected into the whole reaction equipment. And controlling the tee joint to enable a liquid inlet hole of the resin adsorption column to be communicated with the liquid storage kettle and a liquid outlet hole to be communicated with the waste liquid kettle, then enabling 1000mL of acidic waste liquid to pass through the adsorption column at a speed of 4BV/h at 25 ℃, and sending the adsorption waste liquid into the waste liquid kettle for later use.
After adsorption, the tee joint is controlled to enable the liquid inlet hole of the resin adsorption column to be communicated with the desorbent kettle and the liquid outlet hole to be communicated with the batching kettle feeding the hydrogenation reaction kettle. The desorbent is 95% (v/v) ethanol water solution, and is injected into the resin adsorption column at 50 deg.C and 2BV/h, and the desorption solution is fed into the compounding kettle. When the volume of the added desorbent reaches 200mL, the desorption is complete and the introduction of the desorbent is stopped.
Sampling and detecting the acidic waste liquid and the analytic liquid, measuring the content of the o-nitrophenol of the acidic waste liquid and the analytic liquid, and calculating to obtain the recovery rate of the o-nitrophenol, wherein the recovery rate is 99.0%.
Example 2
On the basis of example 1, 50mL of XAD-8 adsorbent resin was used instead of XDA-1, and other conditions were unchanged.
The calculated recovery rate of the o-nitrophenol is 98.9 percent.
Example 3
In this example, industrial alcohol containing 96% (v/v) ethanol and 1% (v/v) methanol was used instead of 95% (v/v) ethanol aqueous solution in addition to example 1, and the other conditions were not changed.
The calculated recovery rate of the o-nitrophenol is 99.2 percent.
Example 4
Based on example 1, 105g of solid o-nitrophenol industrial product and 400mL of 95% (v/v) ethanol aqueous solution are added into a material preparation kettle containing desorption liquid of the o-nitrophenol industrial product, fully dissolved and uniformly stirred, and sent into a downstream hydrogenation reaction kettle to prepare the o-aminophenol.
This example saves 3g of feedstock relative to the complete use of solid o-nitrophenol as feedstock for catalytic hydrogenation.
Example 5
Based on example 1, the adsorption waste liquid in the waste liquid kettle is introduced into a heat exchanger for preheating, then the adsorption waste liquid is sent into an evaporation dryer for complete evaporation, the liquid phase is partially evaporated and then condensed to recover the adsorbent, the solid part is industrial NaCl, and the solid part is packaged and stored for other industrial purposes.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples of the present invention can be used in the practice of the present invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and the description of the present invention.
Claims (13)
1. A method for treating waste water from production of o-nitrophenol comprises the following steps:
s01, treating the waste water after hydrolysis of the o-nitrochlorobenzene, sending the waste water into resin adsorption equipment for adsorption, and discharging adsorption waste liquid;
s02, desorbing the resin by using a desorbent after the adsorption is saturated to obtain a desorption solution,
characterized in that the desorbent comprises mainly ethanol.
2. The process according to claim 1, characterized in that the ethanol content of the desorbent is above 90% (v/v), preferably above 95% (v/v).
3. The process according to claim 2, characterized in that the desorbent is a 95% (v/v) aqueous ethanol solution.
4. The process according to claim 2, characterized in that the desorbent is an industrial alcohol, preferably an industrial alcohol having an ethanol content of more than 96% (v/v) and a methanol content of more than 1% (v/v).
5. The method as claimed in any one of claims 1 to 4, wherein in step S01, the treatment of the wastewater after hydrolysis of ortho-nitrochlorobenzene comprises acidification, temperature reduction, sedimentation, water-oil separation and filtration in turn optionally, and the filtrate is taken to be sent to a resin adsorption device.
6. The method according to any one of claims 1 to 4, wherein the resin is selected from one or a combination of XDA-1, XAD-8 and X-5, preferably XDA-1.
7. The method of claim 6, wherein the adsorption device is selected from the group consisting of a resin adsorption column, a resin adsorption kettle, and a resin adsorption cartridge.
8. The process according to any one of claims 1 to 4, characterized in that the temperature of the adsorption is less than or equal to 25 ℃ and the rate is from 1 to 20BV/h, preferably from 2 to 10 BV/h.
9. The process according to any one of claims 1 to 4, wherein in step S02, the desorption temperature is 30 to 70 ℃ and the rate is 1 to 20BV/h, preferably 2 to 10 BV/h.
10. The method of claim 1, further comprising the steps of:
s03, adding the o-nitrophenol and the desorption solution into the analysis solution obtained in the step S02, and feeding the mixture into a hydrogenation reactor.
11. The method of claim 10, further comprising the steps of:
s04, after the adsorption waste liquid is oxidized and/or neutralized, evaporating the solution to recover salts.
12. The method as claimed in any one of claims 10 to 11, wherein in step S03, the desorption solution is fed into the compounding kettle, and the o-nitrophenol and the desorption solution are added.
13. The production method of o-aminophenol is characterized by comprising the following steps:
s11, hydrolyzing and neutralizing p-o-nitrochlorobenzene to prepare o-nitrophenol;
s12, treating the wastewater generated in the step S11 by using the wastewater recovery method of any one of claims 1 to 12 to recover o-nitrophenol,
s13, preparing the o-aminophenol by hydrogenation reduction using the raw material including the recovered o-nitrophenol obtained in the step S12.
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