CN117362184A - Process for refining triethylamine from acidic glyphosate mother liquor - Google Patents
Process for refining triethylamine from acidic glyphosate mother liquor Download PDFInfo
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- CN117362184A CN117362184A CN202311321170.5A CN202311321170A CN117362184A CN 117362184 A CN117362184 A CN 117362184A CN 202311321170 A CN202311321170 A CN 202311321170A CN 117362184 A CN117362184 A CN 117362184A
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- Prior art keywords
- triethylamine
- solution
- glyphosate
- sodium hydroxide
- mother liquor
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 title claims abstract description 324
- 239000005562 Glyphosate Substances 0.000 title claims abstract description 82
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 82
- 229940097068 glyphosate Drugs 0.000 title claims abstract description 82
- 239000012452 mother liquor Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000007670 refining Methods 0.000 title claims abstract description 13
- 230000002378 acidificating effect Effects 0.000 title claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 117
- 239000000243 solution Substances 0.000 claims abstract description 92
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 26
- 239000012074 organic phase Substances 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 5
- 238000004064 recycling Methods 0.000 claims abstract description 5
- 230000001105 regulatory effect Effects 0.000 claims abstract description 4
- 238000004821 distillation Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 13
- 239000010413 mother solution Substances 0.000 claims description 9
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 description 14
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000005265 energy consumption Methods 0.000 description 5
- 239000012024 dehydrating agents Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000013616 tea Nutrition 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
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a process for refining triethylamine from acid glyphosate mother liquor, which belongs to the technical field of recovering triethylamine from glyphosate mother liquor, and comprises the following steps: adding sodium hydroxide solution into the acid glyphosate mother liquor, and regulating the pH value of the acid glyphosate mother liquor to 9-13; adding cyclohexane into alkaline glyphosate solution for extraction to obtain an organic phase; distilling the organic phase under normal pressure, setting the temperature to 70-82 ℃ to obtain a fraction and a triethylamine aqueous solution, wherein the fraction is cyclohexane, and collecting and recycling the cyclohexane; adding a sodium hydroxide solution with the mass fraction of 30% into a triethylamine aqueous solution, standing and layering to obtain an upper layer solution; sodium hydroxide is added into the obtained upper layer solution, and the solution is kept stand and layered for 12 hours to obtain the high-purity triethylamine.
Description
Technical Field
The invention belongs to the technical field of triethylamine recovery of glyphosate mother liquor, and particularly relates to a method for recovering triethylamine from acidic glyphosate mother liquor.
Background
Glyphosate is a non-selective and residue-free biocidal herbicide, has the characteristics of high efficiency and broad spectrum, has remarkable effect on rooting weeds for many years, is widely applied to rubber, mulberry, fruit, tea gardens and the like, and can be industrially prepared by taking a large amount of triethylamine as a catalyst to obtain glyphosate and simultaneously generate a large amount of acid glyphosate mother liquor, wherein the triethylamine exists in the acid glyphosate mother liquor in the form of triethylamine hydrochloride, and the triethylamine is expensive and has higher toxicity and is necessary to be recycled.
The current treatment process for recovering triethylamine from the acid glyphosate mother liquor mainly comprises the following steps: adding alkaline substances into acid glyphosate to convert the acid glyphosate into alkaline glyphosate solution, reacting triethylamine hydrochloride to generate triethylamine, then feeding the triethylamine into a distillation tower to distill, adding a dehydrating agent into the obtained fraction to obtain purified triethylamine, directly distilling the neutralized mother liquor, wherein the distilled water amount is large and difficult to control, the consumption of the dehydrating agent is increased when the dehydration is performed, the triethylamine is volatile, the secondary loss of the triethylamine is caused when the distillation is performed, and the energy consumption of heating steam is increased.
Therefore, providing a process for improving the recovery rate of triethylamine in glyphosate mother liquor and reducing energy consumption is a technical problem to be solved at present.
Disclosure of Invention
The invention aims to provide a refining process for recovering triethylamine from acidic glyphosate mother liquor, which solves the problems of low recovery and high energy consumption of triethylamine in the existing glyphosate mother liquor.
The aim of the invention can be achieved by the following technical scheme:
a process for refining triethylamine from acidic glyphosate mother liquor comprises the following steps:
firstly, adding a sodium hydroxide solution into an acidic glyphosate mother solution, regulating the pH value of the acidic glyphosate mother solution to be 9-13 to obtain an alkaline glyphosate solution, and simultaneously, reacting triethylamine hydrochloride in the acidic glyphosate mother solution to generate a triethylamine solution;
step two, adding cyclohexane into the alkaline glyphosate solution for extraction, adding cyclohexane for multiple times to ensure that the content of triethylamine in a water layer of the alkaline glyphosate solution is less than 1%, standing for layering, and separating to obtain an organic phase and a residual liquid;
thirdly, carrying out normal pressure distillation on the organic phase obtained in the second step to obtain a fraction and a triethylamine water solution, wherein the fraction collected at the moment is cyclohexane, and recycling the cyclohexane;
fourthly, adding 30% sodium hydroxide solution into the triethylamine aqueous solution obtained in the third step, stirring, standing for layering, and separating the upper triethylamine solution;
and fifthly, adding sodium hydroxide into the upper triethylamine solution obtained in the fourth step, stirring, standing for 12 hours, and layering to ensure that the water content in the triethylamine is 0.1% so as to obtain the high-purity triethylamine.
Further, the acidic glyphosate mother liquor is an acidic mother liquor generated when the glyphosate is prepared by a dialkyl phosphite method.
Further, in the first step, sodium hydroxide solution is added to the acidic glyphosate mother liquor in a mass fraction of 30%.
Further, the volume ratio of alkaline glyphosate solution to cyclohexane is 15:1.
Further, the temperature of the atmospheric distillation was set to 70-82 ℃.
Further, in the fourth step, the volume ratio of the triethylamine aqueous solution to the sodium hydroxide with the mass fraction of 30% is 10:3.
The invention has the beneficial effects that:
1. the acid glyphosate mother liquor contains triethylamine hydrochloride, the pH value is regulated after sodium hydroxide solution is added, so that the acid glyphosate mother liquor is converted into alkaline glyphosate solution, the triethylamine hydrochloride can react to generate triethylamine solution under the strong alkaline environment, the alkaline glyphosate solution is directly put into a distillation tower for distillation in the prior art, but the triethylamine has the characteristic of easy volatilization, a part of the triethylamine can be evaporated and lost in the air, thus triethylamine loss is caused, and the glyphosate solution has low fluidity under the alkaline state, so that the distillation time is long, the heating steam loss is increased, and the distilled water quantity is large and difficult to control; under the environment of strong alkali, the solubility of triethylamine is low, cyclohexane is added into alkaline glyphosate solution for extraction, the content of triethylamine in a water layer of the alkaline glyphosate solution is lower than 1%, after standing and layering, an organic phase containing triethylamine and cyclohexane is separated, and the boiling point of the cyclohexane is lower than that of the triethylamine, so that the cyclohexane and the triethylamine solution can be separated after the organic phase is distilled at normal pressure, the cyclohexane is collected and recycled, sodium hydroxide is added into the triethylamine solution for dehydration, high-purity triethylamine is obtained, the loss of heating steam is reduced, the evaporation of the triethylamine is effectively reduced, and the recovery rate of the triethylamine is improved.
2. According to the invention, the dehydrating agent is adopted to dehydrate after the aqueous triethylamine solution is obtained, the sodium hydroxide has water absorbability, a large amount of sodium hydroxide is consumed when the sodium hydroxide is directly used for dehydration, the aqueous triethylamine solution is firstly added with the sodium hydroxide solution to carry out coarse dehydration, the aqueous triethylamine solution is separated to obtain an upper layer of aqueous triethylamine solution after standing and layering, the sodium hydroxide is added into the upper layer of aqueous triethylamine solution, the aqueous triethylamine solution is separated to obtain the high-purity triethylamine and an alkaline water layer after standing and layering, the alkaline water layer can be recycled after being treated, the operation is simple, the input materials can be recycled, the environment is protected, and the energy consumption can be reduced.
Therefore, the process for recovering the triethylamine from the acidic glyphosate mother solution is a recovery process with high recovery rate, low energy consumption and environmental protection.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
A process for refining triethylamine from acidic glyphosate mother liquor comprises the following steps:
firstly, taking 500mL of acid glyphosate mother liquor, adding a sodium hydroxide solution with the mass fraction of 30%, stirring, adjusting the pH value of the mother liquor to 9 to obtain an alkaline glyphosate solution, and simultaneously, reacting triethylamine hydrochloride in the acid glyphosate mother liquor to generate a triethylamine solution;
adding a small amount of cyclohexane into the alkaline glyphosate solution for multiple times, extracting until the triethylamine content in the aqueous layer of the alkaline glyphosate solution is less than 1% by volume of the added cyclohexane which is 1/15 of the volume of the alkaline glyphosate solution, and separating to obtain an organic phase;
thirdly, performing normal pressure distillation on the obtained organic phase, setting the distillation temperature to be 70 ℃, and obtaining a fraction and a triethylamine water solution, wherein the fraction is cyclohexane, and the yield of the fraction is 89.3%;
fourthly, adding 90mL of 30% sodium hydroxide solution into the triethylamine aqueous solution, stirring, standing for layering, and separating the upper triethylamine solution;
and fifthly, adding 40g of sodium hydroxide into the upper triethylamine solution obtained in the fourth step, further dehydrating, standing for 12 hours, layering, wherein the upper triethylamine is high-purity triethylamine, the recovery rate is 81.1%, the purity is 98.9%, and the lower triethylamine is alkaline water, and continuing to recover and use.
Example 2
A process for refining triethylamine from acidic glyphosate mother liquor comprises the following steps:
firstly, taking 500mL of acid glyphosate mother liquor, adding a sodium hydroxide solution with the mass fraction of 30%, stirring, adjusting the pH value of the mother liquor to 11 to obtain an alkaline glyphosate solution, and simultaneously, reacting triethylamine hydrochloride in the acid glyphosate mother liquor to generate a triethylamine solution;
adding a small amount of cyclohexane into the alkaline glyphosate solution for multiple times, extracting until the triethylamine content in the aqueous layer of the alkaline glyphosate solution is less than 1% by volume of the added cyclohexane which is 1/15 of the volume of the alkaline glyphosate solution, and separating to obtain an organic phase;
thirdly, performing normal pressure distillation on the obtained organic phase, setting the distillation temperature to be 76 ℃, and obtaining a fraction and a triethylamine water solution, wherein the fraction is cyclohexane, and the yield of the fraction is 89.1%;
fourthly, adding 90mL of 30% sodium hydroxide solution into the triethylamine aqueous solution obtained in the third step, stirring, standing for layering, and separating the upper triethylamine solution;
and fifthly, adding 40g of sodium hydroxide into the upper triethylamine solution obtained in the fourth step, further dehydrating, standing for 12 hours, layering, wherein the upper triethylamine is high-purity triethylamine, the recovery rate is 80.9%, the purity is 98.6%, and the lower triethylamine is alkaline water, and continuing to recover and use.
Example 3
A process for refining triethylamine from acidic glyphosate mother liquor comprises the following steps:
firstly, taking 500mL of acid glyphosate mother solution, adding a sodium hydroxide solution with the mass fraction of 30%, stirring, adjusting the pH value of the mother solution to 13 to obtain an alkaline glyphosate solution, and simultaneously, reacting triethylamine hydrochloride in the acid glyphosate mother solution to generate a triethylamine solution;
adding a small amount of cyclohexane into the alkaline glyphosate solution for multiple times, extracting until the triethylamine content in the aqueous layer of the alkaline glyphosate solution is less than 1% of the volume of the alkaline glyphosate mother solution, and separating to obtain an organic phase;
thirdly, performing normal pressure distillation on the obtained organic phase, setting the distillation temperature to 82 ℃, and obtaining a fraction and a triethylamine water solution, wherein the fraction is cyclohexane, and the yield can reach 89.9%;
fourthly, adding 90mL of 30% sodium hydroxide solution into the triethylamine aqueous solution, stirring, standing for layering, and separating the upper triethylamine solution;
and fifthly, adding 40g of sodium hydroxide into the upper triethylamine solution obtained in the fourth step, further dehydrating, standing for 12 hours, layering, wherein the upper triethylamine is high-purity triethylamine, the recovery rate is 81.2%, the purity is 98.7%, and the lower triethylamine is alkaline water, and continuing to recover and use.
Comparative example 1
A process for recycling triethylamine from acid glyphosate mother liquor comprises the following steps:
firstly, taking 500mL of acid glyphosate mother liquor, adding a sodium hydroxide solution with the mass fraction of 30%, stirring, adjusting the pH value of the mother liquor to 9 to obtain an alkaline glyphosate solution, and simultaneously, reacting triethylamine hydrochloride in the acid glyphosate mother liquor to generate a triethylamine solution;
secondly, performing normal pressure distillation on the obtained alkaline glyphosate solution, and collecting a fraction at 94 ℃, wherein the fraction is a triethylamine aqueous solution;
thirdly, adding 90mL of 30% sodium hydroxide solution into the triethylamine aqueous solution obtained in the second step, stirring, standing for layering, and separating the upper triethylamine solution;
and fourthly, adding 40g of sodium hydroxide into the upper layer triethylamine solution obtained in the third step, further dehydrating, standing for 12 hours, layering, wherein the upper layer is triethylamine, the recovery rate is 70.6%, the purity is 97.2%, and the lower layer is alkaline water, and continuing to recover and use.
Comparative example 2
A process for recycling triethylamine from acid glyphosate mother liquor comprises the following steps:
firstly, taking 500mL of acid glyphosate mother liquor, adding a sodium hydroxide solution with the mass fraction of 30%, stirring, adjusting the pH value of the mother liquor to 11 to obtain an alkaline glyphosate solution, and simultaneously, reacting triethylamine hydrochloride in the acid glyphosate mother liquor to generate a triethylamine solution;
adding a small amount of cyclohexane into the alkaline glyphosate solution for multiple times, extracting until the triethylamine content in the aqueous layer of the alkaline glyphosate solution is less than 1% by volume of the added cyclohexane which is 1/15 of the volume of the alkaline glyphosate solution, and separating to obtain an organic phase;
thirdly, performing normal pressure distillation on the obtained organic phase, setting the distillation temperature to be 76 ℃, and obtaining a fraction and a triethylamine water solution, wherein the fraction is cyclohexane, and the yield of the fraction is 89.3%;
and fourthly, adding 75g of sodium hydroxide into the triethylamine aqueous solution obtained in the third step, dehydrating, standing for 12 hours, layering, wherein the upper layer is high-purity triethylamine, the recovery rate is 81.1%, the purity is 98.2%, and the lower layer is alkaline water, and continuously recovering and using.
Taking 1L of acid glyphosate mother liquor, respectively recovering triethylamine in the acid glyphosate mother liquor according to the processes described in examples 1-3 and comparative examples 1-2, detecting the content and purity of the recovered triethylamine, calculating the recovery rate, and recording the consumption of sodium hydroxide as a dehydrating agent, wherein the results are shown in Table 1:
TABLE 1
| Project | Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 |
| Recovery rate of triethylamine% | 81.8 | 80.6 | 81.1 | 70.7 | 81.3 |
| Triethylamine purity% | 98.6 | 98.3 | 98.4 | 97.9 | 98.2 |
| Sodium hydroxide dosageg | 80 | 80 | 80 | 80 | 150 |
As can be seen from table 1, in example 1, the addition of cyclohexane to the alkaline glyphosate solution for extraction increased the recovery of triethylamine compared to comparative example 1; in example 2, sodium hydroxide solution was added to the aqueous triethylamine solution for dehydration, and then sodium hydroxide was added thereto, so that the consumption of sodium hydroxide was reduced and the underlying alkali water was reused, as compared with comparative example 2.
It is noted that relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (5)
1. The process for refining triethylamine from the acidic glyphosate mother solution is characterized by comprising the following steps of:
firstly, adding sodium hydroxide solution into acid glyphosate mother liquor, and regulating the pH value of the acid glyphosate mother liquor to be 9-13 to obtain alkaline glyphosate solution;
step two, adding cyclohexane into the alkaline glyphosate solution for extraction, so that the content of triethylamine in a water layer of the alkaline glyphosate solution is less than 1%, standing for layering, and separating to obtain an organic phase and a residual liquid;
thirdly, carrying out normal pressure distillation on the organic phase obtained in the second step to obtain a fraction and a triethylamine water solution, wherein the fraction collected at the moment is cyclohexane, and recycling the cyclohexane;
fourthly, adding 30% sodium hydroxide solution into the triethylamine aqueous solution obtained in the third step, stirring, standing for layering, and separating the upper triethylamine solution;
and fifthly, adding sodium hydroxide into the upper triethylamine solution obtained in the fourth step, stirring, standing for 12 hours, and layering to ensure that the water content in the triethylamine is 0.1% so as to obtain the high-purity triethylamine.
2. The process for refining triethylamine according to claim 1, wherein the mass fraction of the sodium hydroxide solution in the first step is 30%.
3. The process for refining triethylamine according to claim 1, wherein the volume ratio of alkaline glyphosate solution to cyclohexane is 15:1.
4. The process for refining triethylamine according to claim 1, wherein the temperature of the atmospheric distillation is set to 70-82 ℃.
5. The process for refining triethylamine according to claim 1, wherein the volume ratio of the aqueous triethylamine solution to the sodium hydroxide with the mass fraction of 30% in the fourth step is 10:3.
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| CN202311321170.5A CN117362184A (en) | 2023-10-12 | 2023-10-12 | Process for refining triethylamine from acidic glyphosate mother liquor |
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