CN112341342A - Method for recovering triethylamine in glyphosate mother liquor - Google Patents
Method for recovering triethylamine in glyphosate mother liquor Download PDFInfo
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Abstract
The invention discloses a method for recovering triethylamine in glyphosate mother liquor, which is used for recovering triethylamine in acidic mother liquor obtained when dimethyl phosphite is used for synthesizing glyphosate, and the triethylamine is recovered according to the following steps: 1) adjusting the glyphosate mother liquor or the analytic liquor to be alkaline by using alkali, and then carrying out liquid separation operation to obtain an upper organic phase and a lower water phase; 2) drying the upper organic phase after liquid separation, and recovering triethylamine; 3) adsorbing the lower-layer water phase subjected to liquid separation by using macroporous adsorption resin, adsorbing triethylamine on the resin, resolving by using acid liquor, recovering triethylamine, and returning resolving liquor to the step 1) for recycling; 4) collecting triethylamine recovered in the step 2) and the step 3); finally obtaining the triethylamine with high recovery rate and high quality. The method has reasonable process design, reduces energy consumption, discharges low indexes of COD and ammonia nitrogen of the wastewater, and can directly enter the biochemical system of a general chemical enterprise for treatment.
Description
Technical Field
The invention belongs to the technical field of environmental engineering, relates to a method for recovering and treating triethylamine with high recovery rate and high quality from glyphosate mother liquor, and particularly relates to a method for comprehensively treating triethylamine in acidic mother liquor obtained when glyphosate is synthesized from dimethyl phosphite.
Background
Glyphosate was originally developed by montage corporation of america, is an organophosphorus herbicide with high efficiency, low toxicity, low residue and broad spectrum, and has become the largest pesticide variety sold worldwide.
The production process of glyphosate mainly comprises 4 processes, namely chloroacetic acid process, iminodiacetic acid process, dialkyl phosphite process and trialkyl phosphite process. The dialkyl phosphite method is characterized in that paraformaldehyde, glycine and dialkyl phosphite are used as raw materials, triethylamine is used as a catalyst, and the raw materials are subjected to addition, condensation and acidolysis to obtain glyphosate. The process has the advantages of high yield, low cost and high product quality, and is a synthetic route adopted by domestic major manufacturers. However, the process has the disadvantages that the environmental protection problem is difficult to treat: filtering to obtain mother liquid after acidolysis crystallization. The mother liquor after glyphosate crystallization is a strong acidic liquid containing a large amount of triethylamine, hydrochloric acid and the like. Triethylamine is a catalyst which is widely used, has high price and needs to be recycled. If the water content of triethylamine is large, the consumption and the conversion rate of the materials of the glyphosate synthesis process can be influenced.
Patent documents with publication number of CN106543009A and publication date of 2017, 3 and 29 disclose an effective method for recovering triethylamine in PSI-6206 intermediate synthesis, which mainly comprises the following steps: heating triethylamine wastewater to 55-65 ℃, adjusting alkali by using sodium hydroxide, standing for layering, and adding anhydrous sodium sulfate into an organic layer for drying to obtain triethylamine; and (4) rectifying the wastewater of the water layer at normal pressure, and further recovering triethylamine. The method has the defects of high energy consumption, low triethylamine recovery rate, generation of a large amount of sodium sulfate solid waste, control of the water content of triethylamine obtained by drying and recovering sodium sulfate to be 0.2 percent and difficulty in controlling the water content of triethylamine to be about 0.05 percent.
Therefore, in order to solve the problem of recycling triethylamine at high cost and obtain triethylamine with water content of about 0.05%, an environment-friendly process which is economical, cheap, simple to operate, safe and environment-friendly and short in period is selected, so that the method has great economic value and environmental protection advantages.
Disclosure of Invention
Aiming at the prior art, the invention provides a method for recovering triethylamine in glyphosate mother liquor, which has the advantages of economy, low price, simple operation, safety, environmental protection, short period and environmental protection.
In order to solve the technical problems, the invention provides a method for recovering triethylamine in glyphosate mother liquor, which mainly recovers triethylamine in acidic mother liquor obtained when dimethyl phosphite is used for synthesizing glyphosate, and recovers the triethylamine by taking the glyphosate mother liquor as a starting raw material according to the following steps:
step 1) adjusting glyphosate mother liquor or analytic liquor to be alkaline by using alkali, and then carrying out liquid separation operation to obtain an upper organic phase and a lower water phase;
step 2) drying the upper organic phase after liquid separation, and recovering triethylamine;
step 3) adsorbing the lower-layer water phase subjected to liquid separation by using macroporous adsorption resin, adsorbing triethylamine on the resin, resolving by using acid liquor, recovering triethylamine, and returning resolving liquor to the step 1) for recycling;
step 4) collecting triethylamine recovered in the step 2) and the step 3); the recovered and treated wastewater enters a biochemical system for treatment.
Further, in the method for recovering triethylamine of the present invention:
the specific process of the step 1) is as follows: adjusting the pH value of the glyphosate mother liquor to 10-13 by using alkali at 50-70 ℃, wherein the content of triethylamine in the glyphosate mother liquor is 18% -25%; the liquid separation operation is carried out at 50-70 ℃.
The specific process of the step 2) is as follows: carrying out two drying treatments on the upper-layer organic phase obtained by liquid separation in the step 1), wherein the first drying treatment is to add alkali into the upper-layer organic phase for drying, and the weight percentage ratio of the alkali to triethylamine in the upper-layer organic phase is 10-15%; the secondary drying treatment is to add a molecular sieve into the upper organic phase after the primary drying treatment for drying, wherein the weight percentage ratio of the molecular sieve to triethylamine in the upper organic phase is 2-5%; after the two times of drying, triethylamine is recovered.
The specific process of the step 3) is as follows: adsorbing the lower-layer water phase obtained by separating in the step 1) by using a resin column bed through macroporous adsorption resin, wherein the ratio of the height to the diameter of the resin column bed is 1: 1-5: 1, the operating temperature is controlled at 10-70 ℃, triethylamine is adsorbed on the resin column bed, and the triethylamine is recovered; using a hydrochloric acid solution to analyze the resin column bed, wherein in the analysis process, the hydrochloric acid solution flows through the resin column bed by 0.5-1.0 time of the volume of the resin column bed per hour, and the dosage of the hydrochloric acid solution is 1.0-1.2 times of the mole number of triethylamine in the wastewater entering the column; the mass percent of triethylamine in the collected hydrochloric acid hydrolysis liquid is 10-15%, and the collected hydrochloric acid hydrolysis liquid is sent back to the step 1) for recycling.
In the method for recovering triethylamine according to the present invention, in step 1), the base used is any one of sodium hydroxide, potassium hydroxide, a mixture of sodium hydroxide and potassium hydroxide, an aqueous solution of sodium hydroxide, an aqueous solution of potassium hydroxide, and an aqueous solution prepared by mixing sodium hydroxide and potassium hydroxide. The preferred temperature for the separation operation is 50-55 ℃.
In the step 2), the alkali used in the primary drying treatment is sodium hydroxide or potassium hydroxide, the molecular sieve used in the secondary drying treatment is an A-type molecular sieve, and the A-type molecular sieve comprises a 3A molecular sieve, a 4A molecular sieve and a 5A molecular sieve; the operation temperature of the primary drying treatment and the secondary drying treatment is 20-70 ℃. The molecular sieve used in the secondary drying treatment is preferably a 4A molecular sieve; the operation temperature of the primary drying treatment and the secondary drying treatment is preferably 20 to 30 ℃.
In the step 3), the macroporous adsorption resin is non-polar macroporous adsorption resin, the non-polar macroporous adsorption resin is filled into a column by a wet method, the height-to-diameter ratio of a resin column bed is 2:1, and the adsorption operation temperature is 20-30 ℃. The nonpolar macroporous adsorption resin is styrene.
Compared with the prior art, the invention has the beneficial effects that:
(1) the consumption of the solid alkali is greatly reduced, and the cost is reduced;
(2) the process flow is simple, economical, cheap, safe, environment-friendly and short in period;
(3) the energy consumption is low, and high-energy-consumption unit operation such as rectification is not involved;
(4) the triethylamine with high content and very low water content can be recovered and prepared.
Drawings
FIG. 1 is a process flow of the method for recovering triethylamine according to the present invention.
Detailed Description
The invention will be further described with reference to the following figures and specific examples, which are not intended to limit the invention in any way.
As shown in fig. 1, the method for recovering triethylamine from glyphosate mother liquor provided by the present invention uses glyphosate mother liquor as a starting material, and the process is briefly described as follows:
step 1: at 50-70 ℃, sodium hydroxide or potassium hydroxide is used to adjust the glyphosate mother liquor (in each embodiment, the glyphosate mother liquor, wherein the triethylamine content is 18% -25%, the pH value is 3-5, the COD is 500-34000 mg/L, and the ammonia nitrogen 25000-34000mg/L) to the pH value of 11-13, and the liquid separation operation is carried out at 50-70 ℃;
step 2: and (3) drying the crude triethylamine obtained in the upper layer after liquid separation: adding 10-15% sodium hydroxide or potassium hydroxide equivalent to the weight of triethylamine into the upper-layer organic phase for primary drying, and then using a molecular sieve equivalent to 2-5% of the weight of triethylamine for secondary drying; and (3) carrying out drying treatment and liquid separation to obtain a lower-layer water phase, and carrying out triethylamine adsorption operation through macroporous adsorption resin. Wherein the alkali after the triethylamine is dried for the first time can be recycled to be used for adjusting pH.
And step 3: the operation temperature is 10-70 ℃, and the lower aqueous phase is absorbed by styrene macroporous absorption resin (the ratio of height to diameter is 1:1 to 5: 1). Triethylamine is adsorbed on the resin, after adsorption is finished, acid is used for resolution and recovery, hydrochloric acid solution flows through the resin column bed by 0.5-1.0 time of the volume of the resin column bed per hour for desorption, wherein the dosage of the hydrochloric acid solution is 1.0-1.2 times of the mole number of the triethylamine in the wastewater entering the column. The collected hydrochloric acid desorption solution was subjected to the procedure of step 1.
Finally obtaining the triethylamine with high recovery rate and high quality. The method has reasonable process design, reduces energy consumption, discharges low indexes of COD and ammonia nitrogen of the wastewater, and can directly enter the biochemical system of a general chemical enterprise for treatment.
Example 1 recovery of triethylamine in glyphosate mother liquor was carried out according to the following steps:
step 1: at 50 ℃, 500g of glyphosate mother liquor (the triethylamine content is 18%) is taken, 10.2g of sodium hydroxide is used for adjusting the pH value to 11, and liquid separation operation is carried out at 55 ℃;
step 2: the upper organic phase was first dried by adding 10.2g of sodium hydroxide (corresponding to 12.5% by weight of triethylamine) to obtain 81g of triethylamine (containing 2.5% water). Secondary drying was carried out using 2.5g of molecular sieve (3A molecular sieve);
and step 3: the operation of the lower aqueous phase obtained by separation was: the operation temperature is 30 ℃, and the lower aqueous phase is absorbed by styrene macroporous absorption resin (the ratio of height to diameter is 1: 1). Triethylamine is adsorbed on the resin, and hydrochloric acid solution is used for desorbing by flowing through the resin column bed by 0.5 time of the volume of the resin column bed per hour, and the dosage of the hydrochloric acid solution is 1.0 of the mole number of the triethylamine in the wastewater entering the column. The collected hydrochloric acid desorption solution was subjected to the procedure of step 1.
And (3) combining the triethylamine obtained in the step (2) and the triethylamine obtained in the step (3) to obtain 89.1g of triethylamine (the content of water is 0.05% by a Karl Fischer method, the content of the triethylamine is 99.5% by a gas chromatography method, and the total recovery rate of the triethylamine is 99%).
Example 2 recovery of triethylamine in glyphosate mother liquor was performed according to the following steps:
step 1: at 70 ℃, taking 500g of glyphosate mother liquor (the triethylamine content is 20.1%), using 13g of potassium hydroxide to adjust the pH value to 12, and carrying out liquid separation operation at 70 ℃;
step 2: the upper organic phase was added with 13g of potassium hydroxide (13% by weight based on triethylamine) and dried for the first time to obtain 90g of triethylamine (2.0% by weight aqueous solution). Secondary drying was carried out using 4.5g of molecular sieve (4A molecular sieve); .
And step 3: the operation of the lower aqueous phase obtained by separation was: the operation temperature is 50 ℃, and the lower aqueous phase is absorbed by styrene macroporous absorption resin (the ratio of height to diameter is 2: 1). Triethylamine was adsorbed on the resin and desorbed by passing a hydrochloric acid solution through the resin bed at 0.8 resin bed volumes per hour, the amount of hydrochloric acid solution being 1.1 moles of triethylamine in the wastewater entering the column. The collected hydrochloric acid desorption solution was subjected to the procedure of step 1.
And (3) combining the triethylamine obtained in the step (2) and the triethylamine obtained in the step (3) to finally obtain 99.1g of triethylamine (the content of water is 0.04% by a Karl Fischer method, the content of the triethylamine is 99.5% by a gas chromatography method, and the total recovery rate of the triethylamine is 99%).
Example 3 recovery of triethylamine in glyphosate mother liquor was performed according to the following procedure:
step 1: taking 500g of glyphosate mother liquor (the triethylamine content is 25%) at 60 ℃, adjusting the pH of the glyphosate mother liquor to 13 by using 18g of sodium hydroxide, and carrying out liquid separation operation at 60 ℃;
step 2: the upper organic phase was first dried by adding 16.8g of sodium hydroxide (corresponding to 15% by weight of triethylamine) to obtain 112.1g (containing 2.3% water) of triethylamine. Secondary drying was carried out using 5.6g of molecular sieve (5A molecular sieve);
and step 3: the operation of the lower aqueous phase obtained by separation was: the operation temperature is 30 ℃, and the lower aqueous phase is absorbed by styrene macroporous absorption resin (the ratio of height to diameter is 5: 1). Triethylamine is adsorbed on the resin, and hydrochloric acid solution is used for flowing through the resin column bed at the volume of 1.0 time of the resin column bed per hour for desorption, wherein the dosage of the hydrochloric acid solution is 1.2 times of the mole number of the triethylamine in the wastewater entering the column. The collected hydrochloric acid desorption solution was subjected to the procedure of step 1.
And (3) combining the triethylamine obtained in the step (2) and the triethylamine obtained in the step (3) to finally obtain 123.1g of triethylamine (the content of water is 0.04% by a Karl Fischer method, the content of the triethylamine is 99.4% by a gas chromatography method, and the total recovery rate of the triethylamine is 98.5%).
Example 4 recovery of triethylamine in glyphosate mother liquor was performed according to the following procedure:
step 1: at 60 ℃, taking 500g of glyphosate mother liquor (the triethylamine content is 19%), using 12.1g of potassium hydroxide to adjust the pH value to 11, and carrying out liquid separation operation at 60 ℃;
step 2: the upper organic phase was added with 12.1g of potassium hydroxide (corresponding to 15% by weight of triethylamine) and dried for the first time to obtain 85.2g (aqueous 2.6%) of triethylamine. Secondary drying was carried out using 3.5g of molecular sieve (3A molecular sieve);
and step 3: the operation of the lower aqueous phase obtained by separation was: the operation temperature is 50 ℃, and the lower aqueous phase is absorbed by styrene macroporous absorption resin (the ratio of height to diameter is 4: 1). Triethylamine is adsorbed on the resin, and hydrochloric acid solution is used for flowing through the resin column bed for desorption at the volume of 0.9 times of the resin column bed per hour, wherein the dosage of the hydrochloric acid solution is 1.1 times of the mole number of the triethylamine in the wastewater entering the column. The collected hydrochloric acid desorption solution was subjected to the procedure of step 1.
And (3) combining the triethylamine obtained in the step (2) and the triethylamine obtained in the step (3) to finally obtain 92.9g of triethylamine (the content of water is 0.05% by a Karl Fischer method, the content of the triethylamine is 99.6% by a gas chromatography method, and the total recovery rate of the triethylamine is 97.8%).
The recovery rate of triethylamine finally recovered from the glyphosate mother liquor by adopting the process of the invention is as high as 97.8-99%, so that the content of triethylamine in the recovered and treated wastewater is very low, and through detection, the content of triethylamine in the wastewater is only 0.5% of the mass percent of the wastewater (gas chromatography), the pH value is 10-13, the COD is 200-1000mg/L, and the ammonia nitrogen is 50-200mg/L, so that the triethylamine can directly enter a biochemical system of a general chemical enterprise for treatment.
In summary, the invention has the advantages that the glufosinate-ammonium mother liquor is used as the raw material, and the cost and the energy consumption of the raw material are greatly reduced through a simple process flow; and the triethylamine with high content can be obtained, the recovery rate is high, the cost is low, the process is stable, and the safety and the reliability are realized.
While the present invention has been described with reference to the accompanying drawings, the present invention is not limited to the above-described embodiments, which are illustrative only and not restrictive, and various modifications which do not depart from the spirit of the present invention and which are intended to be covered by the claims of the present invention may be made by those skilled in the art.
Claims (10)
1. A method for recovering triethylamine in glyphosate mother liquor is characterized in that triethylamine in acidic mother liquor obtained when dimethyl phosphite is synthesized into glyphosate is recovered, the glyphosate mother liquor is used as a starting raw material, and the triethylamine is recovered according to the following steps:
step 1) adjusting glyphosate mother liquor or analytic liquor to be alkaline by using alkali, and then carrying out liquid separation operation to obtain an upper organic phase and a lower water phase;
step 2) drying the upper organic phase after liquid separation, and recovering triethylamine;
step 3) adsorbing the lower-layer water phase subjected to liquid separation by using macroporous adsorption resin, adsorbing triethylamine on the resin, resolving by using acid liquor, recovering triethylamine, and returning resolving liquor to the step 1) for recycling;
step 4) collecting triethylamine recovered in the step 2) and the step 3); the recovered and treated wastewater enters a biochemical system for treatment.
2. The method for recovering triethylamine in glyphosate mother liquor according to claim 1, wherein the specific process of step 1) is as follows: adjusting the pH value of the glyphosate mother liquor to 10-13 by using alkali at 50-70 ℃, wherein the content of triethylamine in the glyphosate mother liquor is 18% -25%; the liquid separation operation is carried out at 50-70 ℃.
3. The method for recovering triethylamine in glyphosate mother liquor according to claim 1, wherein the specific process of step 2) is as follows: carrying out two drying treatments on the upper-layer organic phase obtained by liquid separation in the step 1), wherein the first drying treatment is to add alkali into the upper-layer organic phase for drying, and the weight percentage ratio of the alkali to triethylamine in the upper-layer organic phase is 10-15%; the secondary drying treatment is to add a molecular sieve into the upper organic phase after the primary drying treatment for drying, wherein the weight percentage ratio of the molecular sieve to triethylamine in the upper organic phase is 2-5%; after the two times of drying, triethylamine is recovered.
4. The method for recovering triethylamine in glyphosate mother liquor as claimed in claim 1, wherein the specific process of step 3) is as follows: adsorbing the lower-layer water phase obtained by separating in the step 1) by using a resin column bed through macroporous adsorption resin, wherein the ratio of the height to the diameter of the resin column bed is 1: 1-5: 1, the operating temperature is controlled at 10-70 ℃, triethylamine is adsorbed on the resin column bed, and the triethylamine is recovered; using a hydrochloric acid solution to analyze the resin column bed, wherein in the analysis process, the hydrochloric acid solution flows through the resin column bed by 0.5-1.0 time of the volume of the resin column bed per hour, and the dosage of the hydrochloric acid solution is 1.0-1.2 times of the mole number of triethylamine in the wastewater entering the column; the mass percent of triethylamine in the collected hydrochloric acid hydrolysis liquid is 10-15%, and the collected hydrochloric acid hydrolysis liquid is sent back to the step 1) for recycling.
5. The method for recovering triethylamine in glyphosate mother liquor according to claim 1 or 2, wherein the base used in step 1) is any one of sodium hydroxide, potassium hydroxide, a mixture of sodium hydroxide and potassium hydroxide, an aqueous solution of sodium hydroxide, an aqueous solution of potassium hydroxide, and an aqueous solution prepared by mixing sodium hydroxide and potassium hydroxide.
6. The method for recovering triethylamine in glyphosate mother liquor as claimed in claim 2, wherein the temperature for separating in step 1) is 50-55 ℃.
7. The method for recovering triethylamine in glyphosate mother liquor according to claim 3, wherein in step 2), the alkali used in the first drying treatment is sodium hydroxide or potassium hydroxide, the molecular sieve used in the second drying treatment is a type A molecular sieve, and the type A molecular sieves to be used comprise a 3A molecular sieve, a 4A molecular sieve and a 5A molecular sieve; the operation temperature of the primary drying treatment and the secondary drying treatment is 20-70 ℃.
8. The method for recovering triethylamine in glyphosate mother liquor according to claim 3, wherein in the step 2), the molecular sieve used in the secondary drying treatment is a 4A molecular sieve; the operation temperature of the primary drying treatment and the secondary drying treatment is 20-30 ℃.
9. The method for recovering triethylamine in glyphosate mother liquor according to claim 4, wherein in step 3), the macroporous adsorbent resin is nonpolar macroporous adsorbent resin, the nonpolar macroporous adsorbent resin is loaded into a column by a wet method, the ratio of the height to the diameter of a resin column bed is 2:1, and the adsorption operation temperature is 20-30 ℃.
10. The method for recovering triethylamine in glyphosate mother liquor as claimed in claim 9, wherein the nonpolar macroporous adsorbent resin is styrene type.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115784900A (en) * | 2022-11-09 | 2023-03-14 | 湖北泰盛化工有限公司 | Triethylamine purification method in glyphosate production process |
| CN115819250A (en) * | 2022-11-09 | 2023-03-21 | 湖北泰盛化工有限公司 | Method for separating and recovering organic matters from glyphosate alkali mother liquor |
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| CN101190926A (en) * | 2006-11-29 | 2008-06-04 | 浙江新安化工集团股份有限公司 | Method for treating glyphosate mother liquid |
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| CN115784900A (en) * | 2022-11-09 | 2023-03-14 | 湖北泰盛化工有限公司 | Triethylamine purification method in glyphosate production process |
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| CN115784900B (en) * | 2022-11-09 | 2024-06-14 | 湖北泰盛化工有限公司 | Triethylamine purification method in glyphosate production process |
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