CN114989078A - Recovery method of imazamox key intermediate bromine quaternary ammonium salt mother liquor - Google Patents
Recovery method of imazamox key intermediate bromine quaternary ammonium salt mother liquor Download PDFInfo
- Publication number
- CN114989078A CN114989078A CN202210579432.7A CN202210579432A CN114989078A CN 114989078 A CN114989078 A CN 114989078A CN 202210579432 A CN202210579432 A CN 202210579432A CN 114989078 A CN114989078 A CN 114989078A
- Authority
- CN
- China
- Prior art keywords
- mother liquor
- ammonium salt
- imazamox
- quaternary ammonium
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000012452 mother liquor Substances 0.000 title claims abstract description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 23
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000005566 Imazamox Substances 0.000 title claims abstract description 19
- -1 bromine quaternary ammonium salt Chemical class 0.000 title claims abstract description 14
- 238000011084 recovery Methods 0.000 title claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims abstract description 22
- 239000012074 organic phase Substances 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000012071 phase Substances 0.000 claims abstract description 16
- 238000005406 washing Methods 0.000 claims abstract description 16
- 239000002131 composite material Substances 0.000 claims abstract description 12
- 238000004064 recycling Methods 0.000 claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- 239000002351 wastewater Substances 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000007256 debromination reaction Methods 0.000 claims abstract description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
- 238000011049 filling Methods 0.000 claims abstract description 5
- 239000000706 filtrate Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052745 lead Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000000047 product Substances 0.000 abstract description 8
- 150000003863 ammonium salts Chemical group 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 239000010413 mother solution Substances 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000000950 dibromo group Chemical group Br* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000003513 alkali Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 102100027328 2-hydroxyacyl-CoA lyase 2 Human genes 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical group O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- 101710103719 Acetolactate synthase large subunit Proteins 0.000 description 1
- 101710182467 Acetolactate synthase large subunit IlvB1 Proteins 0.000 description 1
- 101710171176 Acetolactate synthase large subunit IlvG Proteins 0.000 description 1
- 101710176702 Acetolactate synthase small subunit Proteins 0.000 description 1
- 101710147947 Acetolactate synthase small subunit 1, chloroplastic Proteins 0.000 description 1
- 101710095712 Acetolactate synthase, mitochondrial Proteins 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 101710196435 Probable acetolactate synthase large subunit Proteins 0.000 description 1
- 101710181764 Probable acetolactate synthase small subunit Proteins 0.000 description 1
- 101710104000 Putative acetolactate synthase small subunit Proteins 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000005693 branched-chain amino acids Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZGSOVUCMPRAGQI-UHFFFAOYSA-N dimethyl 5-(bromomethyl)pyridine-2,3-dicarboxylate Chemical compound COC(=O)C1=CC(CBr)=CN=C1C(=O)OC ZGSOVUCMPRAGQI-UHFFFAOYSA-N 0.000 description 1
- ISULOVLSEOKTOW-UHFFFAOYSA-N dimethyl 5-(dibromomethyl)pyridine-2,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(Br)Br)=CN=C1C(=O)OC ISULOVLSEOKTOW-UHFFFAOYSA-N 0.000 description 1
- MKOJTLPEGLTEFM-UHFFFAOYSA-N dimethyl 5-methylpyridine-2,3-dicarboxylate Chemical compound COC(=O)C1=CC(C)=CN=C1C(=O)OC MKOJTLPEGLTEFM-UHFFFAOYSA-N 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000005080 plant death Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D3/00—Halides of sodium, potassium or alkali metals in general
- C01D3/10—Bromides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a method for recovering a bromoquaternary ammonium salt mother solution of a key intermediate of imazamox, and belongs to the technical field of imazamox production and raw material recycling. The technical scheme is as follows: the method comprises the following steps: 1) washing centrifugal mother liquor generated in the synthesis process of the bromine quaternary ammonium salt with water, standing and layering to obtain a water phase I and an organic phase I; 2) the water phase I is sent to a wastewater pretreatment workshop for unified treatment and recovery of a byproduct sodium bromide; 3) sending the organic phase I to a hydrogenation debromination reaction kettle, filling a composite catalyst in the reaction kettle, introducing hydrogen, controlling the reaction temperature, pressure and time, washing filtrate with water, and layering to obtain a water phase II and an organic phase II; 4) the water phase II is sent to a wastewater pretreatment workshop for unified treatment and recovery of byproduct sodium bromide; 5) and transferring the organic phase to a bromine PDE synthesis section for recycling. The invention not only improves the utilization rate of raw materials, reduces the generation of three wastes, lightens the environmental protection pressure of enterprises, but also reduces the production cost of products.
Description
Technical Field
The invention relates to the technical field of imazamox production and raw material recycling, and particularly relates to a method for recycling a bromoquaternary ammonium salt mother liquor which is a key intermediate of imazamox.
Background
Imazamox is an imidazolinone herbicide variety, is absorbed and conducted by leaves and accumulated in meristems to inhibit the activity of AHAS, so that biosynthesis of branched chain amino acids, namely valine, leucine and isoleucine, is stopped, DNA synthesis, cell mitosis and plant growth are interfered, plant death is finally caused, the toxicity is low, the effect is good, the imazamox is widely applied, and the preparation process of the imazamox usually relates to treatment of a key intermediate, namely a bromine quaternary ammonium salt mother solution.
The components in the separation mother liquor of the quaternary ammonium bromide salt mainly comprise 5-methyl-2, 3-dimethyl dipicolinate (methyl PDE), -dimethyl dibromomethyl-2, 3-dimethyl dipicolinate (dibromo PDE), toluene and other impurities, and the existing treatment modes aiming at the key intermediate quaternary ammonium bromide salt mother liquor of imazamox mainly comprise two types: 1. burning hazardous waste, 2, carrying out biological treatment after high-temperature alkali neutralization, and 3, producing downstream products by utilizing the main components. Wherein, the alkali neutralization needs a large amount of alkali liquor, the biochemical treatment with high COD is difficult, the cost is higher, the incineration treatment requirement is high, the environmental pollution is indirectly caused, the separation difficulty of the product and the impurities in the process of producing downstream products is high, the product quality is difficult to guarantee, and the utilization rate of the raw materials is lower.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the method overcomes the defects of the prior art, and provides a method for recovering the bromoquaternary ammonium salt mother liquor of the key intermediate of imazamox, wherein over 98 percent of dibromo PDE in the mother liquor is converted into methyl PDE and bromo PDE, so that the utilization rate of raw materials is improved, the generation of three wastes is reduced, the environmental protection pressure of an enterprise is relieved, and the production cost of the product is reduced.
The technical scheme of the invention is as follows: a method for recovering a imazamox key intermediate bromine quaternary ammonium salt mother liquor is characterized by comprising the following steps:
1) washing centrifugal mother liquor generated in the synthesis process of the bromine quaternary ammonium salt with water, standing and layering to obtain a water phase I and an organic phase I;
2) the water phase I is sent to a wastewater pretreatment workshop for unified treatment and recovery of a byproduct sodium bromide;
3) sending the organic phase I to a hydrogenation and debromination reaction kettle, filling a composite catalyst in the reaction kettle, introducing hydrogen, controlling the reaction temperature, pressure and time, washing the filtrate with water, and layering to obtain a water phase II and an organic phase II;
4) the water phase II is sent to a wastewater pretreatment workshop for unified treatment and recovery of byproduct sodium bromide;
5) and transferring the organic phase to a bromine PDE synthesis section for recycling.
Preferably, in the step 1), the mass ratio of the centrifugal mother liquor to the washing water is 4: (2-4).
Preferably, in the step 3), the composite catalyst is Zn-Ni-Pd/C or Pb-Ni-Pd/C.
Preferably, the composite catalyst content is 0.2% Zn-0.3% Ni-0.2% Pd/C or 0.2% Pb-0.3% Ni-0.2% Pd/C.
Preferably, in the step 3), the mass ratio of the centrifugal mother liquor to the composite catalyst is 40: (0.5-1.2).
Preferably, the temperature of the hydrogenation and debromination reaction in the step 3) is 20-80 ℃, the reaction time is 0.5-2 h, and the reaction pressure is 0.05-0.3 Mpa.
Compared with the prior art, the invention has the following beneficial effects:
the invention has reasonable design and simple operation, more than 98 percent of dibromo PDE in the mother solution can be converted into methyl PDE and bromine PDE, and then the mixed raw material of the methyl PDE and the bromine PDE is obtained through the working procedures of water washing, layering, rectification and the like. The method not only improves the utilization rate of raw materials, reduces the generation of three wastes and relieves the environmental protection pressure of enterprises, but also reduces the use of noble metal Pd as much as possible and reduces the production cost of products on the premise of ensuring hydrogenation and debromination by adopting the composite catalyst Zn-Ni-Pd/C or Pb-Ni-Pd/C. The production cost can be saved by over 300 ten thousand yuan per year according to the design productivity.
Drawings
FIG. 1 is a schematic process flow diagram of the present invention.
Detailed Description
Example 1
As shown in fig. 1, this embodiment provides a method for recovering a bromoquaternary ammonium salt mother liquor as a key intermediate of imazamox, which specifically comprises the following steps:
adding 800kg of centrifugal mother liquor generated in the synthesis process of the bromine quaternary ammonium salt into a washing kettle, washing with 600kg of water for three times, standing and layering, sending water phase obtained by the three times to a wastewater pretreatment workshop for unified treatment to recover byproduct sodium bromide, hydrolyzing under alkaline conditions, filtering insoluble impurities, extracting a small amount of organic matters, concentrating to obtain byproduct sodium bromide, finally obtaining an organic phase, transferring the organic phase to a hydrodebromination reaction kettle, filling 20kg of a compound catalyst Zn-Ni-Pd/C (the content is 0.2% of Zn, 0.3% of Ni and 0.2% of Pd) into the kettle in advance, starting mechanical stirring, heating to 50 ℃, introducing hydrogen, reacting for 1 hour under the pressure of 0.2MPa, detecting the residual content of dibromo PDE in reaction liquid by using the liquid phase, and controlling the residual content of the dibromo PDE to be less than or equal to 1%. And then cooling and filtering the catalyst for recycling, after 10 times of use, supplementing and adding the catalyst according to 0.05 percent of total amount each time, washing the filtrate for three times by using 600kg of water, standing and layering, sending the obtained water phase for three times to a plant area wastewater pretreatment workshop for unified treatment and recovery of a byproduct sodium bromide, and finally obtaining an organic phase component which is 5-methyl-2, 3-pyridine dicarboxylic acid dimethyl ester (methyl PDE): 27%; dimethyl 5-bromomethyl-2, 3-pyridinedicarboxylate (bromopde): 59 percent of water; dimethyl 5-dibromomethyl-2, 3-pyridinedicarboxylate (dibromopde): 1 percent; toluene: 9 percent; and others: 4 percent, decompressing and recovering the solvent toluene, and transferring to a workshop bromine PDE synthesis working section for recycling.
Example 2
Adding 800kg of centrifugal mother liquor generated in the synthesis process of the bromine quaternary ammonium salt into a washing kettle, washing with 600kg of water for three times, standing and layering, sending water phase obtained by the three times to a wastewater pretreatment workshop for unified treatment to recover by-product sodium bromide, finally transferring an organic phase obtained by the three times to a hydrodebromination reaction kettle, filling 20kg of a composite catalyst Pb-Ni-Pd/C (with the content of 0.2% Pb, 0.3% Ni and 0.2% Pd) in the kettle in advance, starting mechanical stirring, heating to 50 ℃, introducing hydrogen, reacting for 1 hour under the pressure of 0.25MPa, and controlling the residual content of dibromo PDE to be less than or equal to 1%. And then cooling and filtering the catalyst for recycling, washing the filtrate for three times by using 600kg of water, standing and layering, uniformly treating and recycling the byproduct sodium bromide by using the obtained water phase for three times in a plant area wastewater pretreatment workshop, and finally transferring the obtained organic phase to a workshop bromine PDE synthesis section for recycling after decompressing and recycling the solvent toluene.
The invention has reasonable design and simple operation, more than 98 percent of dibromo PDE in the mother solution can be converted into methyl PDE and bromine PDE, and then the mixed raw material of the methyl PDE and the bromine PDE is obtained through the working procedures of water washing, layering, rectification and the like. The method not only improves the utilization rate of raw materials, reduces the generation of three wastes and relieves the environmental protection pressure of enterprises, but also reduces the use of noble metal Pd as much as possible and reduces the production cost of products on the premise of ensuring hydrogenation and debromination by adopting the composite catalyst Zn-Ni-Pd/C or Pb-Ni-Pd/C. The production cost can be saved by over 300 ten thousand yuan per year according to the design capacity.
Although the present invention has been described in detail in connection with the preferred embodiments with reference to the accompanying drawings, the present invention is not limited thereto. Various equivalent modifications or substitutions can be made on the embodiments of the present invention by those skilled in the art without departing from the spirit and scope of the present invention, and these modifications or substitutions are within the scope of the present invention/any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (6)
1. A recovery method of a imazamox key intermediate bromine quaternary ammonium salt mother liquor is characterized by comprising the following steps:
1) washing centrifugal mother liquor generated in the synthesis process of the bromine quaternary ammonium salt with water, standing and layering to obtain a water phase I and an organic phase I;
2) the water phase I is sent to a wastewater pretreatment workshop for unified treatment and recovery of a byproduct sodium bromide;
3) sending the organic phase I to a hydrogenation and debromination reaction kettle, filling a composite catalyst in the reaction kettle, introducing hydrogen, controlling the reaction temperature, pressure and time, washing the filtrate with water, and layering to obtain a water phase II and an organic phase II;
4) the water phase II is sent to a wastewater pretreatment workshop for unified treatment and recovery of byproduct sodium bromide;
5) and transferring the organic phase to a bromine PDE synthesis section for recycling.
2. The method for recovering the imazamox key intermediate bromine quaternary ammonium salt mother liquor as claimed in claim 1, characterized in that: in the step 1), the mass ratio of the centrifugal mother liquor to the washing water is 4: (2-4).
3. The method for recovering the imazamox key intermediate bromine quaternary ammonium salt mother liquor as claimed in claim 1, characterized in that: in the step 3), the composite catalyst is Zn-Ni-Pd/C or Pb-Ni-Pd/C.
4. The method for recovering the imazamox key intermediate bromine quaternary ammonium salt mother liquor as claimed in claim 3, characterized in that: the content of the composite catalyst is 0.2 percent of Zn, 0.3 percent of Ni, 0.2 percent of Pd/C or 0.2 percent of Pb, 0.3 percent of Ni, 0.2 percent of Pd/C.
5. The method for recovering the imazamox key intermediate bromine quaternary ammonium salt mother liquor as claimed in claim 1, characterized in that: in the step 3), the mass ratio of the centrifugal mother liquor to the composite catalyst is 40: (0.5-1.2).
6. The method for recovering imazamox key intermediate bromo-quaternary ammonium salt mother liquor as claimed in claim 1, characterized in that: in the step 3), the temperature of the hydrogenation and debromination reaction is 20-80 ℃, the reaction time is 0.5-2 h, and the reaction pressure is 0.05-0.3 Mpa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210579432.7A CN114989078A (en) | 2022-05-26 | 2022-05-26 | Recovery method of imazamox key intermediate bromine quaternary ammonium salt mother liquor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210579432.7A CN114989078A (en) | 2022-05-26 | 2022-05-26 | Recovery method of imazamox key intermediate bromine quaternary ammonium salt mother liquor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114989078A true CN114989078A (en) | 2022-09-02 |
Family
ID=83029062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210579432.7A Pending CN114989078A (en) | 2022-05-26 | 2022-05-26 | Recovery method of imazamox key intermediate bromine quaternary ammonium salt mother liquor |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114989078A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107673979A (en) * | 2017-09-06 | 2018-02-09 | 肯特催化材料股份有限公司 | The recoverying and utilizing method of halogenation short chain quaternary ammonium waste salt |
| CN109987787A (en) * | 2019-03-05 | 2019-07-09 | 天津大学 | A kind of processing method of high organic wastewater with high salt |
| CN113004197A (en) * | 2019-12-19 | 2021-06-22 | 北京颖泰嘉和生物科技股份有限公司 | Method for recovering 5-methyl-2, 3-pyridinedicarboxylic acid diester |
| CN114478477A (en) * | 2022-01-27 | 2022-05-13 | 江苏中旗科技股份有限公司 | Synthesis process of imazamox |
-
2022
- 2022-05-26 CN CN202210579432.7A patent/CN114989078A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107673979A (en) * | 2017-09-06 | 2018-02-09 | 肯特催化材料股份有限公司 | The recoverying and utilizing method of halogenation short chain quaternary ammonium waste salt |
| CN109987787A (en) * | 2019-03-05 | 2019-07-09 | 天津大学 | A kind of processing method of high organic wastewater with high salt |
| CN113004197A (en) * | 2019-12-19 | 2021-06-22 | 北京颖泰嘉和生物科技股份有限公司 | Method for recovering 5-methyl-2, 3-pyridinedicarboxylic acid diester |
| CN114478477A (en) * | 2022-01-27 | 2022-05-13 | 江苏中旗科技股份有限公司 | Synthesis process of imazamox |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101886143B (en) | Method for preparing reducing sugar by hydrolyzing biomass with super-critical/sub-critical water in two steps | |
| JP5563447B2 (en) | A one-step process for separating biomass components | |
| CN105461620A (en) | Raney nickel catalytic preparation method of 2,2'-bipyridine | |
| CN103667365A (en) | Method for preparing dihydric alcohol from crop straw | |
| CN101948400B (en) | Preparation method of methyl anthranilate | |
| CN110872259A (en) | Method for continuously producing 5-acetoacetylaminobenzimidazolone | |
| CN112250559B (en) | Recycling process of chloro pivaloyl chloride raffinate | |
| CN114989078A (en) | Recovery method of imazamox key intermediate bromine quaternary ammonium salt mother liquor | |
| CN103525880B (en) | Application of maleic anhydride waste residue in preparation of aspartic acid and method for preparing aspartic acid by using maleic anhydride waste residue | |
| CN204151265U (en) | Hexanediamine production system | |
| CN104557557A (en) | Method for preparing nitroanisole from m-nitrochlorobenzene oil | |
| CN102603514A (en) | Process for preparing sodium gluconate from crop straws | |
| CN101402552B (en) | Method for producing m-cresol with direct hydrolyzation | |
| CN102134198B (en) | Method for separating nitrochlorobenzene meta-position oil | |
| CN104829029B (en) | A kind of processing method of the industrial wastewater of synthetic allantoin | |
| CN101429130B (en) | Method for producing 2,6-dichlorine para-nitraniline | |
| CN111704538A (en) | Method for preparing p-hydroxyphenylacetic acid by using microreactor | |
| CN105349778A (en) | Clean production method for recycling yellow phosphorus, iron oxide red and precious metal from ferrophosphorus | |
| CN102392082B (en) | Method for preparing glucose by catalyzing hydrolysis of cellulose by low-solubility organic acid | |
| CN213559080U (en) | Acid leaching oxidation harmless treatment equipment for waste incineration fly ash water washing slag | |
| CN102875401A (en) | Method for producing DL-aspartic acid from waste radix asparagi | |
| CN212532804U (en) | Catalyst recovery system of PTA oxidation residue | |
| CN113582919A (en) | Method and device for synthesizing 3-aminopyridine by tubular reactor | |
| CN104910142A (en) | Method for preparing vitamin B1 intermediate (pyrimidine) | |
| CN214830198U (en) | Energy ecological recycling system for refining workshop |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |